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Investors in private markets pay the fees, yet they often get the worst experience. They are demanding the streamlining of alternative investments. In this episode of Wealth Actually, I talk with Ryan Eisenman, co-founder and CEO of Arch, about why it can take thousands of clicks to manage a single fund position and what better data means for advisors, family offices and the families they serve. Alternative investments are moving well beyond the institutional world. Private equity, private credit, hedge funds and venture capital now show up in high-net-worth and even retail portfolios. The paperwork has not kept up. K-1s, capital calls, investor letters and valuations still sit in dozens of portals and PDFs. Ryan explains how Arch gathers those documents, turns them into structured data and gives investors a single view of commitments, cash flows, performance and exposure. We also cover the rules he sees good allocators follow, the gap in after-tax analysis, PPLI, valuation lag, estate-planning valuations and the next friction point Arch wants to remove: the subscription document. Key takeaways The LP pays, so the LP should come first. Ryan’s starting point is simple: the limited partner pays the fees across private markets, so the invesotr”s needs should dictate the infrastructure.. Three allocation rules. Don’t lose money, avoid adverse selection, and diversify. Ask why an opportunity reached you and source deals actively rather than waiting for whoever knocks on the door. Commitment-based assets break traditional reporting. Most performance systems were designed for stocks and bonds. Unfunded commitments, call pacing, redemption windows and wire instructions need their own data layer. Holistic advice depends on seeing held-away assets. Advisors cannot give complete advice or plan well if they cannot see the private investments a client made elsewhere. AI is already doing practical work. Arch summarizes long investor letters, captures manager-reported IRR and lets clients query their own portfolio data. After-tax thinking is still underdeveloped in alts. Investors rarely know whether a fund will generate QSBS-eligible gains or how a manager’s trading style affects their after-tax return. PPLI and trusts are a reporting gap. Policies holding insurance-dedicated funds create similar tracking burdens for trustees, trust companies and advisors. Permissioned access helps the whole advisory team. Clients can share all or part of their data with auditors, tax accountants, valuation firms and estate planners. The next frontier is the subscription document. Arch is testing a tool to automate subscription paperwork as it pushes toward a one-click experience in private markets. Episode timestamps 00:00 Preview: why advisors need to see held-away assets 00:17 Introduction and disclaimer 01:26 Who pays the fees? The problem Arch set out to solve 02:37 Lessons from large allocators for newer alternative investors 04:02 What Arch does: documents, data and dashboards 05:13 Cash management: commitments, capital calls and distributions 06:50 How RIAs, multifamily offices and banks use Arch 08:00 Working across custodians, fund administrators and portals 09:03 AI insights, IRR and investor-letter summaries 10:18 Who sees the data, and adding third-party context 11:31 Power users versus weekly digest readers 13:24 Educating the new wave of alternative investors 14:53 After-tax returns, tax-aware funds and QSBS 16:01 PPLI, insurance-dedicated funds and trustee reporting 18:12 Helping advisory firms scale as alts grow 19:36 Manager selection, partnerships and data protection 21:06 Scale: $620 billion on the platform and new data partners 22:43 Valuation lag and secondary-market marks 23:34 Estate-planning valuations and permissioned access 24:32 What’s next: automating the subscription document 25:41 Where to find Arch and closing Notable quotes “Usually when you pay for something, you get a good experience. Private markets is such where people pay for investments and pay all the fees and get an awful experience.” — Ryan Eisenman “There should be a one-click way to manage alternative investments and not the 5,500 clicks that it takes today to manage a single fund position over its 10-year life.” — Ryan Eisenman “It’s hard to avoid the bad and prioritize the good if you don’t know which is good and which is bad.” — Ryan Eisenman “Yes, the GP often hires the fund admin, but the LP pays the GP.” — Ryan Eisenman About Ryan Eisenman Ryan Eisenman is the co-founder and CEO of Arch, a technology platform for managing private market investments. He co-founded Arch in 2018 to address the fragmented, manual work of private investing, and the platform now centralizes K-1 collection, capital calls, distributions, documents and performance reporting. Before Arch, he worked at Deloitte and Techstars, among other firms. He earned his bachelor’s degree in Human and Organizational Development from Vanderbilt University. (Orion’s Standard Deviations guest profile) About Arch: Arch announced a $52 million Series B led by Oak HC/FT in September 2025. In July 2026, it reported $539 billion in private market assets on its platform, and by late September 2026 it said it served more than 650 allocators with more than $600 billion in assets. (Business Wire, September 2025; Business Wire, July 2026; InvestmentNews, September 2026) Interesting links Arch — Ryan’s company and the place to schedule a demo. Ryan Eisenman on LinkedIn Ryan Eisenman on X Arch Raises $52M Series B (Business Wire) — The 2025 funding announcement led by Oak HC/FT. Arch Surpasses $500B in Assets on Platform (Business Wire) — July 2026 update naming MUFG Innovation Partners and Franklin Templeton as Series B investors. Arch Pushes AI Portfolio Monitoring into Pre-Investment Due Diligence (InvestmentNews) — Coverage of Arch Investment Research, launched in September 2026. ‘Charles Schwab for Private Markets’ Arch Raises $52 Million (Fortune) — Background on Arch’s positioning and growth. IRS: Exclusion of Gain on Qualified Small Business Stock — The Section 1202 (QSBS) rules Ryan mentions at 15:34, in the Schedule D instructions. Private Placement Life Insurance with Jay Judas — Our related Wealth Actually episode on PPLI and insurance-dedicated funds. Frequently asked questions What does Arch do? Arch collects documents from fund portals and managers on a client’s behalf, structures the data and presents it in a dashboard. Investors and advisors can see commitments, funded and unfunded amounts, performance, K-1s, capital-call alerts and underlying exposures in one place. Who uses Arch? Ryan says the largest client segment is investment advisors, including RIAs, multifamily offices and private banks. Arch also serves individual LPs, accountants and other allocators. Why is reporting on private investments so difficult? Private investments are commitment-based rather than share-based. Capital is called over time, distributions arrive irregularly, valuations lag and every fund reports a little differently. Most traditional reporting systems were built for stocks and bonds. What rules should a newer alternative investor follow? Ryan’s three rules: don’t lose money, avoid adverse selection by asking why the opportunity reached you, and diversify. He also recommends an intentional allocation plan and active deal sourcing. How does Arch address valuation lag? Arch adjusts the value shown on the platform for capital calls and distributions and is beginning to show underlying marks, including secondary-market pricing for some private companies, ahead of the next quarterly statement. Can estate planners and valuation firms use Arch data? Yes. Clients can permission all or part of their Arch data to third parties such as auditors, tax accountants, advisors and estate planners working on valuations. Full transcript This transcript is lightly edited for readability from the episode audio (26:17). Filler words and repeated starts have been removed without changing substance. It is not a certified verbatim record; please check the audio before quoting. [00:00] Ryan Eisenman: We think that fundamentally, if you can’t see your clients’ other assets that they might have made away from you with another advisor or before they worked with you, then it’s really hard to give them true holistic advice and to help them understand which products to select or how to do planning. [00:17] Frazer Rice: Welcome back to the Wealth Actually podcast, the show that features experts, entrepreneurs and commentators that will give you the right knowledge, planning and guidance so you can preserve your assets and enjoy your wealth. Learn more and subscribe today at WealthActually.com. This podcast is for educational and entertainment purposes. It is neither investment, legal nor tax advice. It does not represent the opinions of the employers or the host or guest. [00:42] Frazer Rice: Welcome back. Alternative investments are the rage these days. There’s an insatiable demand for hedge funds, private credit, private equity, infrastructure and the like. Ryan Eisenman is the co-founder and CEO of Arch, which is a tool to help investors understand what they own and the different decisions around allocation. We’re going to find out what the future looks like in this space. Ryan, welcome aboard. [01:06] Ryan Eisenman: Thanks, Frazer. Great to be here. [01:07] Frazer Rice: Thrilled to have you on. For those of us who work in the high-net-worth and ultra-high-net-worth space, the idea of reporting and aggregating assets and getting a real fix on what people have, where it is, how it should be spent, how performance is running and all that, it seems like a never-ending cycle. With Arch, what was the problem that you guys were trying to solve? [01:31] Ryan Eisenman: Yeah.

Private Placement Life Insurance (PPLI) is a life insurance policy used as a tax-efficient wrapper for long-term investments. It works best for families who have money they will never spend, who can commit about $10 million in premium, who hold the policy in an irrevocable trust, and who are willing to give up control of investment decisions. In this episode of Wealth Actually, JAY JUDAS, CEO of Life Insurance Strategies Group, explains how PPLI works, who it fits, where it gets missold, and how compounding inside a properly built policy can reach the third, fourth, and fifth generations. https://youtu.be/fIknhINvP5I https://open.spotify.com/episode/2RuIoiYqZw16xzGXNbY8nT?si=f6G_LpwHR9WiVbWCZbWsmA Episode Overview PPLI has moved from a niche product to one of the most discussed tools in ultra-high-net-worth planning. It now shows up in my own practice and in many conversations with trust and estate lawyers. I asked Jay Judas to help sort out the opportunities from the risks. Jay runs a fee-based consultancy that does not sell insurance. Well over 60% of his firm’s work now involves PPLI. Yet he says more than half of the people who come to him believing they need PPLI should be in something else, or in nothing at all. Our discussion covers why tax-inefficient alternatives such as private credit fit inside the policy, why the policy belongs in an irrevocable trust, and Jay’s “magic has a price” rule of thumb for minimum premium. We compare insurance-dedicated funds (IDFs) with separately managed accounts (SMAs), walk through the investor control and diversification rules, and look at why the “tax-free loans” pitch misses the point. We close with a case study: $50 million, three policies, and a 40-year runway. Key Takeaways PPLI is not for everybody. More than half of the prospects Jay’s firm evaluates are better served by another solution. Use money you will never touch. Jay says the right question is not what percentage of a portfolio to commit. It is which dollars are already set aside for children and grandchildren. Magic has a price. Jay’s practical minimum is about $10 million of premium, paid in as quickly as possible. Some low-cost carriers can make $5 million work. Tax-inefficient assets benefit most. Private credit, private equity, real estate, litigation finance, life settlements, and infrastructure can face combined tax rates above 50% for New York and California residents. Own the policy in an irrevocable trust. A policy held personally pulls the death benefit into the insured’s taxable estate. IDFs and SMAs offer two routes. An IDF is an insurance-only version of a fund and usually covers a single strategy. An SMA lets a manager, often the family’s existing RIA, run a discretionary mandate under a broad investment policy statement. Investor control is the real risk. You can choose an IDF or set broad goals with an SMA manager. You cannot direct trades, pick specific deals, or arrange a plan before the policy is issued. Emails can be subpoenaed. Diversification is policed for you. Under Section 817(h), one investment cannot exceed 55% of the account, two cannot exceed 70%, three cannot exceed 80%, and four cannot exceed 90%. Carriers hire fund administrators to monitor compliance. Policy loans are a weak selling point. In PPLI, the manager must sell assets to fund a loan, which can disrupt compounding and run into lockups. In 23 years, Jay has seen no more than 10 policies tapped for a distribution. Trustees and trust protectors need periodic reviews. Jay’s firm found one 30-year-old policy whose fees were double current market levels and got them reduced. Check who is selling. Most PPLI is now issued by established carriers and requires securities-licensed professionals. Be cautious of unlicensed producers who push offshore carriers. The prize is G3 to G5. In Jay’s illustration, $50 million compounding at 9% inside a policy reaches about $1.6 billion over 40 years. The same money in a taxable California account, after federal estate tax, reaches about $159 million. Chapters 00:00 Introduction and disclaimer 00:45 Why PPLI dominates UHNW planning conversations 01:26 Life Insurance Strategies Group and why most PPLI inquiries are not a fit 02:32 Asset location: tax-inefficient alternatives and the life insurance chassis 04:45 Why the policy belongs in an irrevocable trust 05:23 The ideal client and the “magic has a price” minimum 07:07 How much to commit: money you will never touch 08:06 Retail life insurance versus PPLI 10:28 Insurance-dedicated funds (IDFs) versus separately managed accounts (SMAs) 12:02 Why RIAs are embracing the SMA route 12:52 Investor control: what you can and cannot do 14:42 Diversification rules under Section 817(h) 16:17 Single assets, Webber v. Commissioner, and prearranged plans 17:53 It takes a village: the parties and their fees 19:31 The liquidity myth and the problem with policy loans 21:37 The trustee’s role and reviewing older policies 23:34 Borrowing from the policy and the last-bucket principle 26:23 Questions to ask before you buy 27:44 Case study: planning for G3, G4, and G5 30:10 Where to find Jay Judas Notable Quotes “More than half of the people who come to us thinking they should be in PPLI, it’s not appropriate for them.” (Jay Judas) “The price of PPLI magic, to make it work, is in my opinion a minimum commitment of $10 million, paid as quickly as you can into the policy.” (Jay Judas) “Pick the fund, but not what that fund is doing.” (Jay Judas) “In my 23 years of being involved in PPLI, I’ve seen no more than 10 policies ever touched for a distribution.” (Jay Judas) “The real attraction of PPLI is that I can now plan for G3, G4, and G5.” (Jay Judas) About the Guest Jay C. Judas is CEO of Life Insurance Strategies Group  (LISG), a Boston-based independent life insurance advisory firm that does not sell products. LISG advises individuals, families, advisors, and carriers on private placement life insurance, advanced estate planning, executive benefits, and cross-border planning. Jay is a former senior executive with Old Mutual, where he served as Senior Vice President and Chief Distribution Officer of Global High-Net-Worth Distribution. He also held senior roles with Sun Life Financial, Crown Global Insurance Company, and BF&M Insurance Group (Philadelphia Estate Planning Council). He co-authors the annual U.S. PPLI Market Report with Lion Street. Jay holds a JD from Rutgers University School of Law, an M.Sc. in Leadership from Northeastern University, and a BA from the University of Northern Iowa. Resources Mentioned Life Insurance Strategies Group U.S. PPLI Market Report (Lion Street and LISG) Jay Judas on LinkedIn Diversification requirements, Treas. Reg. § 1.817-5 (Cornell LII) Rev. Rul. 2003-91, IRS guidance on investor control (IRS) Frequently Asked Questions What is private placement life insurance (PPLI)? PPLI is a variable life insurance policy offered privately to accredited investors and qualified purchasers. The premium is invested through insurance-dedicated funds or a separately managed account. Investment growth inside the policy is not currently taxed, and the death benefit generally passes income-tax-free, provided the policy meets the tax definition of life insurance and the owner does not control the investments. How much money do you need for PPLI? Jay Judas recommends a minimum commitment of about $10 million in premium, paid in as quickly as possible. At that level, carrier, manager, and broker fees are small enough to avoid a meaningful drag. Some lower-cost carriers can make about $5 million work. Who is PPLI a good fit for? PPLI fits families who hold long-term, tax-inefficient investments and have wealth they will not spend during their lifetimes. The best candidates plan to pass that money to children and grandchildren through an irrevocable trust. Jay estimates that more than half of the people who explore PPLI are better served by something else. What is the difference between an IDF and an SMA in PPLI? An insurance-dedicated fund (IDF) is an insurance-only version of a fund, usually a single strategy such as private credit. A separately managed account (SMA) is a discretionary mandate run by an investment manager, often the family’s existing RIA, under a broad investment policy statement. Both must comply with investor control and diversification rules. What is the investor control doctrine? The investor control doctrine holds that if the policyholder controls the investments inside the policy, the IRS can treat the policyholder as the owner and tax the investment income currently. Policyholders may choose among available funds or set broad goals. They may not direct specific trades, select specific deals, or set up a prearranged investment plan. What are the PPLI diversification rules? Under Section 817(h) and Treasury Regulation § 1.817-5, one investment cannot exceed 55% of the separate account’s value, two cannot exceed 70%, three cannot exceed 80%, and four cannot exceed 90%. In practice, this requires at least five investments. Carriers typically hire fund administrators to monitor compliance. Can you borrow from a PPLI policy? Yes, but it is rarely a good idea. In PPLI, the carrier does not advance cash. The investment manager must sell assets to fund a loan, which can interrupt compounding and run into lockups on private investments. Jay says he has seen no more than 10 policies tapped for distributions in 23 years. Why should a PPLI policy be held in an irrevocable trust? If the insured owns the policy personally, the death benefit is included in the insured’s taxable estate. An irrevocable trust, such as an ILIT, can keep the growing policy value and death benefit outside the estate for future generations. Who are the parties in a PPLI transaction? A typical transaction involves the insurance carrier, a securit

DAVID PAKMAN — political commentator, YouTube host, and author of the new book Pay Attention — joins me to talk about Algorithms, AI, and the Attention Economy. We break down how attention became the core commodity of the modern economy, why algorithms reward outrage over nuance, and what happens when AI starts cloning creators without their consent. David walks through the real story of “The Daniel Carter Show,” a YouTube channel that used AI voice-cloning to impersonate him and was algorithmically recommended to his own audience. From there, the conversation covers why right-wing messaging has a structural advantage on algorithmic platforms, what “behavioral surplus” means and how platforms monetize it, and the media-literacy habits families should be teaching the next generation before handing over unrestricted social media access. https://youtu.be/RTy2vuw7oe8 We also discuss anonymity and accountability online, why the “calm middle” is checking out of social media, and a simple “media diet” framework for staying informed without getting consumed. https://www.amazon.com/Pay-Attention-Algorithms-Suppressing-Rewiring/dp/0063569809/ https://open.spotify.com/episode/3ti3d6FvXAmgwqX1h4pMQQ?si=x8cwV2-DQNewJJX9yM6Vpw Themes Why attention is the defining commodity of the digital economy How “rented ground” platforms (YouTube, TikTok, podcasts) shape what creators can say The real story behind an AI deepfake impersonating David Pakman “Behavioral surplus”: how platforms monetize what you don’t even realize about yourself A practical media-diet framework — and how to talk to kids and aging parents about safe media use AI’s Impact on Video Timestamped Show Notes / Chapters 00:00 — Cold open: “You just have to learn how to play the game” — David on the political right’s platform advantage 00:15 — Wealth Actually intro & disclaimer 00:40 — Introducing David Pakman and today’s topic: algorithms, attention, and responsible media consumption 00:59 — David’s new book Pay Attention: why he wrote it and the “confessional” behind-the-curtain angle 02:38 — Attention as the “lingua franca” of the modern economy 03:25 — Creating content on “rented ground”: YouTube, TikTok, and podcasting platforms as landlords with no clear lease 04:44 — How Facebook’s shift from chronological feeds to algorithmic “For You” feeds rewired the entire incentive system 06:36 — Why boring-but-important topics (like housing policy) need an emotional hook to break through 07:37 — What the political right does better on these platforms — and why it’s about style, not substance 08:01 — The COVID vaccine messaging case study: fear and scapegoating vs. accurate-but-boring nuance 10:10 — From the traditional GOP to the “Trump party”: the John McCain/POW moment as an inflection point 11:05 — The pre-Trump roots of modern right-wing messaging (AM/low-power FM religious radio, Rush Limbaugh) — and the recent press-corps ban of CNN, Politico, and MSNBC from the White House briefing room 12:08 — Why the “calm middle” checks out of social media, and how outrage drives engagement 12:40 — The trap of over-weighting vocal-minority feedback: “98% of my Twitter replies are anti-social screeds” 14:29 — Online anonymity, accountability, and Jonathan Haidt’s real-identity proposal 14:55 — David’s own experiment: requiring a real email address cut toxic messages by 95–99% 16:10 — AI and deepfakes: the danger of synthetic content built on real people’s data and personalities 16:44 — The “Daniel Carter Show”: how an AI voice clone of David was algorithmically pushed to his own audience 18:59 — “Behavioral surplus” — how platforms monetize the gap between what you say and how you actually behave 21:31 — David’s media-diet “food pyramid”: proactive, vetted sources as the staple; algorithmic scrolling as junk food 24:09 — Advising families and next generations on safer, smarter media habits 25:17 — David’s own household rules on kids, screens, and delaying unrestricted social media access 27:12 — The financial-literacy parallel: media literacy as a life skill that should be taught early 27:58 — The media-literacy pyramid — and the Pew Research finding that most Americans (across party lines) struggle to tell fact from opinion 29:10 — The AI risk multiplier: outsourcing critical thinking to algorithms 29:32 — Where to find Pay Attention and follow David Pakman 30:19 — Closing thanks Transcript [00:00] “So I actually think that from a political standpoint, if what people are trying to do is use these platforms to get the ideas they believe in out, you just have to learn how to play the game. I don’t think there really is any other solution on the political side.” — David Pakman [00:15] [Show Intro] Welcome back to the Wealth Actually podcast, the show that features experts, entrepreneurs, and commentators that will give you the right knowledge, planning, and guidance so you can preserve your assets and enjoy your wealth. Learn more and subscribe today at WealthActually.com. This podcast is for educational and entertainment purposes. It is not investment, legal, or tax advice. It does not represent the opinions of the employers of the host or guests. David Pakman has a multimillion person following and an outsized presence with his online political talk show. He knows a lot about how the algorithms work across platforms like YouTube. We’re gonna talk a lot about that and also how to responsibly consume media in this day and age [00:56] Frazer Rice: David Pakman, thanks for coming on. [00:58] David Pakman: Thank you. [00:59] Frazer Rice: You’ve got a new book out. Pay Attention. By the time this podcast launches, it will be fully out and about on Amazon and wherever else everybody gets books. Tell us a little bit, just briefly, from the book writing process, your major voice in media, and what got you writing on this topic? [01:18] David Pakman: Well, there’s a confessional aspect to the book — just kind of explaining the compromises as a content creator that I have to make. And I say “have to” in the context of, if I want this to be my full-time job, if I wanna succeed at it, there are compromises that have to be made, as is the case in most jobs. So one aspect of the book is kind of pulling back the curtain a little bit. The other aspect is about best practices at the individual level, when so much of what we come to believe is true — and sometimes isn’t — is mediated by these digital platforms that are algorithmically delivering content in a way that is not impartial. It’s so important to understand why we are fed the things we are fed rather than other things, as a starting point for having conversations about what we want the world to look like. And then I also have a political interest in this — as someone on the political left, I think the political right naturally benefits from the way these algorithms work, not because of anything special they’ve done, but from their communication style. So if the political left wants to succeed — which I think it does, at least it claims to — it has to better learn how to conduct itself on these platforms. We’ll dive into that in a second. [02:38] Frazer Rice: One thing in your book — and I think generally that you talk about — is the commodity of attention, and how that has become really the lingua franca of the modern economy. Maybe dive into that a little bit about why that has become the case. [02:55] David Pakman: Tell me from which perspective do you want me to talk about it? ‘Cause that could go in a bunch of directions. [03:00] Frazer Rice: Well, I think the main thing is to say: if people are sort of used to oil or plastics or gold being a commodity, the idea of attention really driving, in many ways, economic decisions or allocation decisions around productivity — that seems to be something that’s a little bit more nuanced in the last, certainly five years, but maybe even back the last 10 or 15. [03:25] David Pakman: Well, I think that conversation kind of starts with understanding incentives. I create content on what I describe as “rented ground” — YouTube, TikTok, podcasting platforms — all of these platforms are basically lending me space, for as long as it’s at their pleasure to do so, to publish my content. And they’re landlords that don’t really give me a clear lease that tells me what I’m allowed to do and expected to do. I kind of have to figure it out by doing it. Their incentive is to keep users on the platform as long as possible — the longer users are there, the more money the platform makes. So when we look at the content we get from these platforms, it’s not because the content is true that we’re shown it. It’s not because the content makes society better or makes us better citizens. We’re shown the content that the algorithm determines is most likely to keep us on the platform. That’s really the starting point. One of the critical changes: I don’t know how early you were on Facebook, but at the start, when I was in college, if you were friends with 20 people, your home feed was a chronological feed of what your friends posted. Very simple — if you looked on Saturday, went back Sunday and scrolled, at some point you’d hit the last thing you saw Saturday, and you were kind of done. There was a clear break point — “okay, I’m caught up, I’m getting off Facebook.” That’s a real problem for a platform that wants to keep you on there as long as possible. So eventually Facebook and Twitter switched to an algorithmically recommended feed. TikTok calls it the “For You” page, and it’s just the default. What that does is show you content not in chronological order, but based on what keeps you watching.

What happens to your voice, image and online accounts after you die? In this episode of Wealth Actually, I welcome back NATALIA PARKER and TATYANA THURSTON of DEXIT to discuss digital identity and estate planning in the age of AI. https://youtu.be/MdnUcekE-08 The issue is bigger than recovering a password. An executor may have to decide whether to keep a book on sale, preserve a podcast, close a social media account or respond to an AI-generated version of the person who died. Those decisions can put income, reputation and family wishes in conflict. We discuss how to build a digital-asset inventory, document instructions for online accounts, protect against deepfake scams and think through the use of your name, image, likeness and voice. The practical question: does your estate plan give the next person enough information to make these decisions? What we cover Digital estate planning: Why books, podcasts, photographs, recordings and online accounts belong in the planning conversation. Instructions, not just an inventory: What an executor needs to know about the assets, the platforms and what you want done with each account. Deepfake fraud: Why a familiar face or voice should not replace verification when money or sensitive information is involved. AI after death: The questions raised by avatars, simulated social media activity and the reuse of a person’s creative work. Fiduciary judgment: How executors and trustees may have to weigh commercial value against reputation and the emotional impact on a family. A technology component: Why Natalia and Tatyana argue that technology planning belongs alongside wealth, tax and estate planning. Episode timestamps Timestamps refer to the supplied episode audio, including the opening preview and introduction. 00:00 Preview and introduction 00:52 Why AI belongs in the estate-planning conversation 03:36 Name, image and likeness beyond celebrities 04:56 Platform access, ownership and closing accounts 06:54 Deepfake fraud and verifying money transfers 08:48 Building a digital defense strategy 10:22 Digital-asset inventories and consent to AI recreation 13:15 Facebook, posthumous posting and the ethics of AI 15:46 Avatar businesses and the digital afterlife 18:50 Robin Williams and restrictions on likeness 21:02 Executors, trustees and the emotional cost to families 23:10 Adding a technology component to the estate plan 23:53 Where to find DEXIT and closing thoughts About the guests Natalia Parker and Tatyana Thurston are the co-founders of DEXIT, a digital succession-planning business. DEXIT works with clients, wealth advisors and estate planners on plans for online assets and accounts. (DEXIT founder profile; DEXIT) Resources and related episodes DEXIT: Learn about the guests’ work at dexitplan.com. Our earlier conversation: Digital Assets Estate Planning with Natalia Parker and Tatyana Thurston covers digital inheritance, account access and planning for executors. Related Wealth Actually episode: Technology and Estate Planning explores digital tools for estate-planning work. Questions from the episode What should a digital-asset inventory include? In this conversation, we discuss online accounts, publishing platforms, books, podcasts, images, recordings and intellectual property. The emphasis is on pairing the inventory with instructions about what should be preserved, closed or considered for continued use. What should I decide about an AI version of myself? The guests suggest documenting whether you want your voice, image or recordings used to recreate you digitally after death. They also discuss the tension between those wishes, an executor’s decisions and the family’s reaction to the result. Why is this an issue for people who are not celebrities? Our discussion includes family photographs, personal accounts, recordings and unpublished creative work. Their importance may be emotional rather than commercial, which is why the conversation extends beyond celebrity estates. What is the first planning conversation to have? Start with what exists, what matters to you and what you want done with it. The next question is who will have to carry out those instructions and whether they have a usable roadmap. Clarification on the Meta discussion The opening preview and the discussion around 13:15 refer to Meta’s patent for simulating a user’s social media activity, including after death. In February 2026, a Meta spokesperson told Business Insider, “We have no plans to move forward with this example”; the report distinguishes the patent from a decision to implement the technology. (Business Insider) The transcript below preserves the conversation as recorded. This clarification is separate from the speakers’ remarks. Transcript This transcript has been lightly edited for readability, removing filler words and repeated starts while preserving the substance of the conversation. Speaker timestamps are approximate navigation aids; examples and legal or technical statements reflect the discussion, not independently verified advice. [00:00] Tatyana Thurston: Facebook in 2060, they’ll have way more deceased user accounts than live user accounts. And Facebook needs to monetize that. It takes up space in their servers, and they’ve actually recently patented the right to use the content that has been posted by deceased users. And they will be reposting as if they were still around. [00:26] Announcer: Welcome back to the Wealth Actually podcast, the show that features experts, entrepreneurs, and commentators that will give you the right knowledge, planning, and guidance so you can preserve your assets and enjoy your wealth. Learn more and subscribe today at wealthactually.com. This podcast is for educational and entertainment purposes. It is not investment, legal, nor tax advice. It does not represent the opinions of the employers of the host or the guests. [00:52] Frazer Rice: Natalia, Tatyana, welcome back. [00:54] Natalia Parker: Thank you for having us. [00:55] Tatyana Thurston: Thanks for having us. [00:56] Frazer Rice: Well, our last discussion actually engendered a lot of feedback from people who, if they were stuck in the executor role or in the trustee role, I thought it was very helpful in terms of laying out the roles and responsibilities and what you have to do to keep yourself and the estates safe. I thought we’d talk a little bit today about the intersection of technology, which hits close to home to me. I’m a big user of AI and really helped move things along for clients that way. But for me, I have a lot of IP as well. [01:29] Frazer Rice: I’ve got podcasts, I’ve got books, I’ve got all sorts of images, et cetera. And there’s an AI component to some of that as well. Maybe take us through a little bit about how you think about preparing someone who has to preside over somebody else’s IP, their name, image, likeness, and that type of thing as a broader scope of issues as they get prepared going on this journey. [01:57] Natalia Parker: Yes. First of all, yes, you do have a lot. And right now, your executors will have to know which platforms you’re using. And they have to know what you would like to do with those accounts. Do you want to keep your book open for readers and keep collecting money? Do you want your podcast to stop podcasting? Everything has to be written down somewhere. And then you have to have a plan for each one of them. We had a case where we had to close their Amazon book account. That was difficult because there were several authors. [02:37] Frazer Rice: Oh, yikes. So a lot of cooks in the kitchen, and all of them have an opinion on what they want to do with it. [02:45] Natalia Parker: Yes. So that’s where the DEXIT plan comes in. [02:52] Frazer Rice: In terms of getting your arms around what it means to have digital assets nowadays, a lot of people, we talked before about social media accounts, images, maybe even voice recordings, et cetera, that may not be commercial, but they’re personal and important to them. And as we all know, AI is using every bit of data to train their LLMs and all the other things that they have at play to make their AI agents more effective. What is the state of the art as far as either using or protecting your own digital presence if you don’t want to be a part of AI, or how do you responsibly be engaged with it? [03:36] Tatyana Thurston: I think it depends on where the name, image, and likeness is being used and in what capacity. For example, we have kids today as young as in high school, and they have a social media presence. They’re gaining followers in their teens, and maybe their goal is to be a professional football player. All those platforms hold their data and their videos and their name. And maybe they’re making money from it even at a young age. [04:07] Tatyana Thurston: So even estate planning isn’t just for folks who are older. It could even start as early as young kids because they’re on platforms. Those are platforms which are public. The public platforms is a ripe source for scammers to take your name, image, and likeness and capitalize it in another way. So there’s a source of truth that some people are trying to do, especially celebrities. A lot of celebrities now are actually creating avatars of themselves so that the true representation of themselves is on record. It’s actually really interesting, but that’s part of preserving their digital presence online. [04:56] Frazer Rice: And to circle back a little bit to what we were talking about in the previous episode, when you’re intersecting with these platforms, usually the social media platforms, the Facebooks, the Twitters, the Instagrams, et cetera. Step one, obviously, is to catalog exactly where you are, which is its own full-time job in many ways. But then what exactly do you have on there? It’s images, it’s quotes, it’s things like that. How do you intersect w

Fire the Whole Investment Team: Meb Faber on 250 Years of American Compounding and Why CalPERS Can’t Beat a 60/40 allocation https://youtu.be/9lBYkG4J2sY A dollar invested in the U.S. stock market in 1800 is worth roughly $200 million today, and Meb Faber says the giant pension funds paid to beat that kind of compounding usually can’t. In this episode of Wealth Actually, Frazer Rice talks with Meb Faber, co-founder and CIO of Cambria Investment Management and host of The Meb Faber Show, about his new coffee-table book Investing in America: The Rise of a 250-Year Bull Market, the shareholder yield thesis behind Cambria’s ETF lineup, and his long-running public campaign arguing that CalPERS and other giant institutional pools routinely fail to beat a simple, low-cost buy-and-hold portfolio. https://open.spotify.com/episode/4WmnPm3GN8jwQtJuCVV9XG?si=nLLcz8y8RSuydORA5_ZHGQ Key Takeaways America is, in Faber’s words, the greatest compounding machine in history. He puts a dollar invested in U.S. stocks in 1800 at roughly $200 million today — a number he uses to reframe how clients should think about staying invested through wars, depressions, and pandemics. The book’s origin story starts with meme stocks. Faber says COVID pulled a new generation of retail investors into the market through gamified trading apps, and he wanted to hand them a historically grounded alternative to day-trading and zero-day options. Diversification is older than the country itself. Faber traces the concept back to 15th- and 16th-century joint-stock voyages — the Mayflower and the Virginia Company among them — where spreading capital across many risky expeditions let “merchant adventurers” survive when any single ship was lost. Shareholder yield, not dividend yield, is Cambria’s core factor. Since the S&P 500’s dividend yield now sits near an all-time low of 1.04%, Faber argues the real signal is cash dividends plus net buybacks — net of the dilution from stock-based compensation that quietly erodes shareholders’ ownership every year. Faber’s CalPERS critique boils down to one line: “the returns are not bad, they’re just not good.” He’s built an entire body of work, including Cambria’s ENDW endowment-style ETF, arguing that giant pools with virtually unlimited access to managers still can’t consistently beat a disciplined global 60/40. Complexity is often the enemy, not the edge. Faber contrasts investing with almost every other field of expertise: hiring the best doctor or coach nearly always helps, but hiring the most sophisticated (and expensive) money manager frequently doesn’t. Illiquidity has a way of showing up at the worst possible time. Faber points to endowments getting caught upside down in 2008–2009 and to more recent leveraged blowups as the same lesson repeating: over-lever a portfolio and you’re out of chips at the poker table. The real accountability gap is career incentives, not investment theory. Faber contrasts Yale, which gets a pass for strong long-term results, with Harvard’s endowment, which he says has underperformed for two decades without anyone losing their job over it — a dynamic he says maps directly onto UHNW family governance. Timestamps [00:00] Cold open — CalPERS CIOs vs. UK prime ministers [00:29] Show open and disclaimer [00:54] Welcome: Meb Faber, Cambria, and the new book [02:07] The $76 price tag and the 1776 joke [03:13] Genesis of Investing in America: COVID, meme stocks, and joint-stock voyages [06:33] The most surprising find: Ben Franklin’s “Mind Your Business” motto [09:09] Argentina vs. the U.S. — what actually drove American exceptionalism [12:47] Cambria today: the shareholder yield thesis [17:46] Why politicians target buybacks instead of stock-based comp [20:54] The CalPERS critique begins [21:34] The Ivy Portfolio, the ENDW endowment ETF, and year-one results [25:45] The Nevada pension comparison and the liquidity-complexity pushback [26:56] Institutional blowups, Harvard’s endowment dysfunction, and misaligned incentives [29:36] The “anti-Switzerland of asset management” bit [31:16] Close: where to find Meb, Cambria, and the book Pull Quotes “No, no, no, no, Frazer — it is $76, in honor of 1776.” — Meb Faber “A dollar would be worth roughly $200 million today… despite wars and depressions and pandemics and everything else terrible that’s happened in the history of the world, this relentless compounding is such a fun story.” — Meb Faber “There are dividend funds in the U.S. today… whose actual dividend yield is lower than their management fee. A negative net dividend yield — an astonishing statistic in 2026.” — Meb Faber “Who’s had more turnover in the past 10 years — CalPERS CIOs or UK prime ministers? Both totally dysfunctional. I think CalPERS has a slight edge, but it’s close.” — Meb Faber “I’m the anti-Switzerland of asset management.” — Meb Faber About the Guest Meb Faber is co-founder, CEO, and Chief Investment Officer of Cambria Investment Management, an independent, privately owned advisory firm built around quantitative asset management and alternative investment strategies (BusinessWire). He hosts The Meb Faber Show, one of the most widely followed investing podcasts, and is the author of eight books, including The Ivy Portfolio, Global Asset Allocation, Global Value, Shareholder Yield, and now Investing in America: The Rise of a 250-Year Bull Market — his first coffee-table book, released to coincide with the U.S. semiquincentennial (Curzio Research). Proceeds from the book go to charities that fund investment accounts for Americans born in the country. A ninth book, The Awesome Portfolio, is slated for release on September 8, 2026 (Meb Faber on X). Contact Meb Faber & Cambria Cambria Investment Management: cambriainvestments.com Cambria Funds: cambriafunds.com Meb’s blog, podcast & research: mebfaber.com The Meb Faber Show: themebfabershow.com Twitter/X: @MebFaber Book — Investing in America: available on Amazon, Barnes & Noble, and signed via Pages bookstore in Manhattan Beach, CA (Acquirer’s Multiple) Cambria Funds Mentioned Shareholder Yield suite (SYLD, FYLD, EYLD, plus small-cap and large-cap variants) — cash dividends plus net buybacks plus net debt reduction, divided by market cap (MarketWatch) GVAL — Global Value ETF screening the cheapest quartile of roughly 45 country markets by long-term valuation (Cambria — GVAL) TAIL / FAIL — U.S. and global ex-U.S. tail-risk ETFs pairing short-term Treasuries with a rolling ladder of out-of-the-money S&P 500 puts (Cambria — TAIL) Trinity Portfolio (TRTY) — roughly half buy-and-hold, half trend-following across a basket of other Cambria funds (Cambria — Trinity Portfolio) ENDW — Cambria’s endowment-style ETF, discussed on the show as roughly $150–180 million at launch and referenced later in conversation as having grown toward roughly $5 billion in assets with more than 100,000 investors (MebFaber.com) The CalPERS Critique — Further Reading 9 Institutions Can’t Beat a Basic Buy-and-Hold Allocation — MebFaber.com How California’s $450B Pension Fund Misses the Basics of Investing — YouTube Should a Robot Be Managing CalPERS’ Portfolio? — MebFaber.com, 2015 Index Funds vs. Ivy League — MarketWatch/Barron’s Streetwise CalPERS: America’s Misled and Misleading Pension Leader — Retired Public Employees Association CalPERS Section II Performance Tables (2026) — CalPERS.ca.gov Reducing the Noise of AI Investing – FrazerRice.com Frequently Asked Questions How much would a dollar invested in the U.S. stock market in 1800 be worth today? Meb Faber says roughly $200 million, using the figure to illustrate how relentless compounding has powered through wars, depressions, and pandemics over the country’s history. It’s an illustrative, back-of-envelope estimate rather than a precise index calculation, since standardized stock indexes didn’t exist in 1800. Why is Meb Faber’s new book priced at $76? It’s a nod to 1776 and the country’s founding, timed to the U.S. semiquincentennial. All proceeds go to charities that fund investment accounts for Americans born in the country. What is shareholder yield, and how is it different from dividend yield? Shareholder yield is cash dividends plus net stock buybacks (net of new share issuance, particularly from stock-based compensation), divided by market cap. Faber argues it captures real capital return to shareholders better than dividend yield alone, especially now that the S&P 500’s dividend yield sits near an all-time low of about 1.04% and share buybacks have outpaced dividends every year since the late 1990s. What is Meb Faber’s argument against CalPERS and other large pension funds? Faber’s recurring claim is “the returns are not bad, they’re just not good” — that giant institutional pools with access to virtually any manager on the planet still fail to consistently beat a simple, low-cost, diversified buy-and-hold portfolio, once fees and complexity are accounted for. Cambria launched an endowment-style ETF (ENDW) partly to make this a live, ongoing comparison rather than a hypothetical one. What is Cambria’s endowment-style ETF and how does it compare to institutions like CalPERS? ENDW replicates a Yale/Swensen-style endowment allocation — global stocks, global bonds, and real assets like gold, TIPS, and REITs — in a low-cost ETF with an all-in expense under 25 basis points. Faber uses it as a running, real-time benchmark against actual endowment and pension performance reported each fiscal year. Why does Meb Faber say complexity is often the enemy in investing? Unlike most fields, where more resources and the best available experts reliably produce better outcomes, Faber argues that in investing, more complexity and more access to exotic managers frequently

When the Title Changes but the Authority Doesn’t: Family Business Succession with Paul Edelman Most family business succession plans fail not because the legal structure is wrong, but because authority never actually moves. In this episode of Wealth Actually, Frazer Rice talks with Paul Edelman, PhD of Edelman & Associates about how to tell the difference between a real handoff and a cosmetic one. Edelman unbundles succession into six separate questions, explains the three behavioral tells that reveal who is really in charge, draws a hard line between a legitimate safeguard and an open-ended veto, and makes the case that agreement from a family is not the same thing as ownership of a decision. https://youtu.be/p2KCsftvM74 Key Takeaways Succession is not one decision — it is at least six. Who gets the economic benefit of ownership, who votes the shares, who appoints and removes directors, who runs operations, who receives what information, and who retains informal influence after formal authority ends. Watch behavior, not titles. Compensation changes and org charts are easy to read and easy to fake. How decisions actually get made — and whether they get reversed — is the real signal. Three tells that authority hasn’t moved: the next management layer still routes real decisions to the founder; the successor has never had a disputed call stand; and in a genuine crisis, the founder is the one who walks into the room. Speed is not the test. A five-year transition can be disciplined development; a six-month transition can be denial with a deadline. The test is whether milestones and readiness criteria are observable and stable, or whether the goalposts keep moving. “Not ready” is not a concern — it is a placeholder. If a founder cannot restate it in specific, testable terms, the obstacle is emotional rather than substantive, and it needs a different path. Advisor impatience often masquerades as clarity. When you catch yourself thinking “why can’t they just do this,” ask whose timeline is actually being served — the family’s, or your need to close the file. A safeguard is bounded; a veto is not. Reserve specific extraordinary decisions with defined scope, thresholds, triggers, evidence, and duration. “The successor is in charge unless the founder feels uncomfortable” is an undefined operational veto. Agreement is not ownership. A family can be outvoted and formally agree while owning nothing. Ownership comes from having weighed the trade-offs and the implications of each option in the room. Timestamps [00:00] Cold open — why “he’s just not ready” is untestable [01:05] Welcome: founders at the sell-or-transfer crossroads [01:48] Unbundling succession into six separate questions [02:23] Running a diagnostic on where the founder actually is [03:00] Watch behavior, not titles — and what the CFO tells you [04:00] Decision reversals and the second-guessing test [05:00] The crisis test: who owns the emergency [05:36] Fast handoff vs. staged succession and prolonged ambiguity [06:10] Milestones that show it’s working — and goalposts that keep moving [08:00] Inside vs. outside successors and family dynamics [08:54] Competing heirs and the outside CEO as bridge or avoidance [09:47] Reading resistance: making “not ready” addressable [11:10] The advisory ecosystem’s frustration with stalled progress [12:16] Whose timeline is being served? [13:31] Push, pause, or reframe — the art and science of advising [15:00] When to change the forum, the decision rights, or bring in a facilitator [15:36] Safeguards vs. vetoes and the trap doors founders build [17:37] Board composition: independence vs. familiarity [20:00] Restructuring boards to create seats for new expertise [20:54] Income-dependent family members vs. growth-minded owners [21:34] Agreement is not ownership: dividends vs. reinvestment [23:31] Matching complexity to the outcomes you need [25:00] Communicating decisions to people who weren’t in the room [25:26] How to reach Paul Edelman [25:46] The Edelman–Shenkman trilogy for estate planning attorneys [29:19] Close Pull Quotes “If the CFO briefs the new successor CEO and then confirms things with Dad, then the org chart is not telling the real story.” — Paul Edelman “To have authority when things are going well is fine. But the person who owns the crisis is the one who’s really owning the leadership.” — Paul Edelman “A safeguard should be limited, explicit, and connected to some extraordinary risk. A veto is an ongoing ability to stop or reverse any old ordinary decision.” — Paul Edelman “Just because there’s an agreement in name doesn’t mean there’s ownership of the decision.” — Paul Edelman About the Guest Paul Edelman, PhD is a coach, facilitator, and mentor at Edelman & Associates, where he works with family enterprise and family office leaders on decisions that cannot be delegated. He holds a PhD in developmental psychology from Harvard University and a BS in physics from MIT, and serves as faculty at The UHNW Institute and the Bertarelli Institute for Family Entrepreneurship at Babson College. Contact Paul Edelman Email: [email protected] Website: edelmancoaching.com (contact form on site) LinkedIn: linkedin.com/in/pauledelman The Edelman & Shenkman Trilogy Paul and Martin M. “Marty” Shenkman, CPA, MBA, JD, PFS, AEP (Distinguished), of Shenkman Tietz, have written a three-part series aimed at estate planning attorneys: Simplicity and its trade-offs — When Clients Ask for a Simple Estate Plan, WealthManagement.com / Trusts & Estates, July 8, 2026. The language of estate planning conversations — published in Steve Leimberg’s LISI Estate Planning Newsletter (subscriber archive). Beneficiary education — forthcoming October 2026, expected in Estate Planning. Paul’s running author archive: wealthmanagement.com/author/paul-edelman More from Paul Edelman Approval Is Not Ownership: Helping Family Office Investment Decisions Hold Under Pressure — Family Wealth Report, July 1, 2026 How Families Can Override Emotions to Make Better Judgments — Family Business Magazine, April 9, 2026 Lessons For Families And Their Advisors From A Hit TV Series — Family Wealth Report, February 24, 2026 Stronger Family Bonds and Better Strategic Decisions — FFI Practitioner, January 20, 2026 Frequently Asked Questions What are the six questions a family business succession decision should be broken into? Who receives the economic benefit of ownership; who votes the shares; who appoints and removes directors; who runs the company operationally; who receives what information; and who continues to hold influence after formal authority ends. Bundling these into a single “handoff” decision is what creates ambiguity. How can you tell whether authority has really transferred to a successor? Watch three behaviors. First, where the next management layer goes for real decisions — employees are excellent at reading where power actually lives. Second, whether the successor has ever made a call the founder disagreed with and had it stand. Third, the crisis test: when a covenant breaks or a key employee leaves, who walks into the room and who gets briefed afterward. Is a fast succession better than a gradual one? Speed itself is not the test. A five-year transition can represent disciplined development, and a six-month transition can be avoidance followed by an arbitrary deadline. What matters is whether responsibility moves against observable milestones, whether the successor learns from outcomes instead of being rescued, and whether readiness criteria stay fixed rather than shifting each time the successor advances. What is the difference between a safeguard and a veto? A safeguard is limited, explicit, and tied to extraordinary risk — selling the company, debt above a threshold, issuing new equity, changing core strategy, or related-party transactions — with defined scope, thresholds, process, duration, trigger, evidence, and who decides. A veto is an ongoing ability to stop or reverse ordinary decisions. If the founder can intervene whenever they feel uncomfortable, that is an undefined operational veto. How should advisors handle their own frustration with a stalled family? Notice that impatience often feels like clarity. When you think “I see exactly what they need to do, why can’t they just do it,” that is often the moment to slow down and ask whose timeline is being served — whether the ambiguity is genuinely damaging the company, or whether the recommendation mainly closes the case and relieves the advisor’s discomfort with uncertainty. What makes an independent director genuinely independent in a family company? The ability to exercise business judgment and fiduciary duty free from undue family influence or loyalty to a particular branch. A director who is the founder’s golfing buddy or tied to one family faction will struggle to deliver the value independence is supposed to provide. Why isn’t agreement good enough? Because agreement in name is not ownership. A family branch can be outvoted, formally accept the outcome, and still feel no responsibility for it. Ownership comes from working through the trade-offs — what each option makes better and worse — so participants can say they helped weigh the considerations even if the result was not their first choice. Full Transcript [00:00] Paul Edelman: The resistance often takes the form of some sort of concern that is stated like, for example, the most general concern that people will say is, well, he or she, the likely successor, is just not ready. But that phrase “not ready” is at a very high level of generality. It’s not specific enough to be testable or to be capable of being satisfied. So the challenge is to work with the founder to help them expres

Choosing a Trustee: Why Naming Your Kid May Be a Mistake — Marguerite Lorenz Short answer: Naming your child as trustee, executor, or agent under your power of attorney is the default choice for most American families — and it is frequently the wrong one. In this episode of Wealth Actually, host Frazer Rice talks with California Licensed Professional Fiduciary and Master Certified Independent Trustee Marguerite Lorenz about why roughly two-thirds of American adults still have no estate plan, why the job of a trustee is far more intimate and technical than families expect, and how to decide between a family trustee, a bank or trust company, and an independent professional trustee. https://youtu.be/56bzuORe8YI Episode Overview: Who Will Actually Run Your Plan? Most estate planning conversations stop at the documents. Marguerite Lorenz argues the documents are the easy part. The hard part is staffing — deciding who steps in when you can no longer make new decisions, and whether that person can absorb the technical, financial, and emotional weight of the job. Lorenz has served as trustee, executor, agent under power of attorney for finance, and agent for health care for hundreds of families since 2003. She is the author of three books — Luck or Control? The Life-Improving Power of Estate Planning, How to Be a Successful 90-Year-Old, and the newly updated Ethics for Trustees 2.0 — and she is Vice-Chair of the Independent Trustee Alliance. Her framing line, and the one that should stick with every listener: “If you don’t get your estate plan done, you’re suing your family. You’re making them go to court. And who would want to make anyone else go to court?” — Marguerite Lorenz This is the second time Marguerite has joined the show. Her first appearance covered the mechanics of individual trusteeship: EP.75 — Individual Trusteeship with Marguerite Lorenz. Key Takeaways •Only about a third of American adults have any written estate plan — and Lorenz argues half of those plans would not actually function when needed. •Professionals are barely better than the public. When Lorenz polls rooms of attorneys, CPAs, and financial advisors, roughly one-third raise their hands for a complete, up-to-date, ready-to-go plan. •The trustee role is intimate, not administrative. A trustee sees your paperwork, your bills, your medications, and your bedroom. “Who is going to be the first person in your bedroom when you are no longer able to make new decisions?” •Incapacity, not death, is the long tail. Many people live for five or six years unable to make new decisions. The trustee’s job often runs during your lifetime, not just after it. •A professional trustee can be temporary. Lorenz recounts stepping in for a client during cancer treatment, providing a full accounting, and stepping back down when he recovered — then serving again after his death. Would your child step back down? •Estate planning is about preferences, not predictions. “Our power in estate planning is not prediction, it’s setting our preferences” — and preferences can only be set while you are competent. •Quality of life belongs in the plan. Not just tax, legal, and financial terms — but how you want to live, where you want to live, and what small things matter (for Lorenz, an international selection of dark chocolate). •Digital assets are now a core trustee problem. Phones, social accounts, and daily transactions all require someone with access and authority. •A will does nothing while you are alive. “The will doesn’t operate at all if you go to the hospital and you haven’t granted authority to anyone.” •Cost is usually overestimated. Both an estate plan and an independent professional trustee typically cost far less than probate court. •Revisit every five years. Calendar a five-year check-in with your attorney to review law changes, marriages, divorces, births, and deaths. Chapters and Timestamps •[00:00] Cold open: “If you don’t get your estate plan done, you’re suing your family.” •[00:32] Welcome back — introducing Marguerite Lorenz, California trustee and author •[01:14] Luck or Control? — why fear keeps families from finishing an estate plan •[02:22] What a full-time trustee actually sees: trustee, executor, agent for finance, agent for health care •[03:49] Why families default to naming a child — and where that breaks down •[05:00] The skill set nobody screens for: negotiation, calm, empathy, and grief •[05:40] Case study: serving as temporary trustee through a client’s cancer treatment — and stepping back down •[07:51] Why even attorneys need their own attorney: nobody is objective about their own circumstances •[09:09] The five-year estate plan check-in as a life milestone •[09:39] How to Be a Successful 90-Year-Old — living well to the very end •[10:20] The “black box” problem: privacy, dignity, and care in your own home •[11:54] Preferences over predictions — planning for your future vulnerable self •[13:40] Rewriting an advance health care directive after hundreds of hospital bedsides •[16:13] The statistics: only a third of adults — and only a third of professionals — are actually ready •[17:47] Frazer’s challenge to advisors: you can’t advise well if you aren’t practicing what you preach •[18:22] The first question in Luck or Control?: “Hey professional, do you have your estate plan done?” •[19:21] Ethics for Trustees 2.0 — what’s new in the updated audio and PDF edition •[20:27] Family trustee vs. bank trustee vs. independent professional trustee •[21:52] The looming crisis: the great wealth transfer, incapacity, and digital assets •[24:54] Documenting the “why” behind hard trustee decisions •[25:23] Probate courts overrun, bioethics committees, and next-of-kin defaults •[26:54] Where to find the books, the podcast, and the Independent Trustee Alliance directory About the Guest: Marguerite Lorenz, MCIT, CLPF Marguerite Lorenz is a California Licensed Professional Fiduciary (CLPF #319) and a Master Certified Independent Trustee (MCIT). She has served as Trustee, Executor, Agent for Finance, and Agent for Health Care for more than 200 families since 2003 as managing partner of Lorenz Private Trustees. Marguerite is Vice-Chair of the Board of the Independent Trustee Alliance, past Chair of the California Professional Fiduciaries Bureau Advisory Committee, and host of the Plan For This podcast. She is the author of Luck or Control? The Life-Improving Power of Estate Planning, How to Be a Successful 90-Year-Old, and Ethics for Trustees 2.0. About the Host: Frazer Rice Frazer Rice is the author of Wealth, Actually: Intelligent Decision-Making for the 1% and host of the Wealth Actually podcast, where he interviews experts, entrepreneurs, and commentators on preserving assets and enjoying wealth. Resources and Links Mentioned •PlanForThis.com — Marguerite’s books, the Plan For This podcast, and a free First Steps toolkit. Ethics for Trustees 2.0 is now exclusive to this site (audio + PDF bundled with purchase). •TrusteeAlliance.com — the Independent Trustee Alliance directory for locating certified independent trustees by state. •Marguerite Lorenz on LinkedIn •California Professional Fiduciaries Bureau — state licensing for professional fiduciaries •Related episode: EP.75 — Individual Trusteeship with Marguerite Lorenz •Related episode: What If You Are Named in a Will or Trust? Frequently Asked Questions Should I name my child as trustee? Not automatically. A child understands the family but may lack the technical skill to handle tax, legal, financial, and medical decisions — and may be grieving or in conflict with siblings at the exact moment judgment is required. Marguerite Lorenz notes that a trustee must be a good negotiator, stay calm under pressure, set aside personal feelings, and enforce rules the grantor set. She also raises a test most families never consider: if you recover, would your child voluntarily step back down and hand you a full accounting? What is the difference between a family trustee, a corporate trustee, and an independent trustee? A family trustee is a relative or friend serving in a personal capacity, usually unpaid and untrained. A corporate trustee is a bank or trust company with institutional infrastructure, minimum account sizes, and staff turnover. An independent professional trustee is a licensed or certified individual — like a California Licensed Professional Fiduciary — who serves full-time, carries a succession plan, and can often be engaged at a lower cost than families expect. The Independent Trustee Alliance maintains a national directory of independent trustees. What does a trustee actually do while I am still alive? A trustee acting during incapacity manages assets, accounts for every dollar, handles taxation, pays bills, coordinates care, and increasingly manages digital assets such as phone-based transactions and social media accounts. Lorenz emphasizes that many people live for five or six years unable to make new decisions, so the trustee’s lifetime role is often longer and more demanding than the post-death administration. How often should I update my estate plan? Roughly every five years, or sooner after a major life event such as marriage, divorce, birth, death, a liquidity event, or a change in tax law. Lorenz recommends putting a five-year reminder in your phone to call your attorney and ask what has changed in the law and in your life. What happens if I go to the hospital without an estate plan? The hospital and its bioethics committee will do the best they can and will look for next of kin to make decisions for you — potentially people with whom you have never discussed your personal

“Reducing the Noise of AI Investing”: In this Wealth Actually episode, Frazer Rice speaks with KEVIN SHEA, Senior Equity Analyst at BNY Wealth, about AI Investing and how investors should think about artificial intelligence as an investment theme rather than just a headline-driven trend. They discuss the difference between hype and durable fundamentals, how to segment AI opportunities across infrastructure, software, and end-user adoption, and why free cash flow still matters when evaluating companies tied to AI. https://open.spotify.com/episode/1NGM8j2KqdiUFWSLguBMEH?si=YmB4s0OVSqyy6U3Mpg7OaA https://youtu.be/Wnlub-HoiUo The conversation also explores circular financing risk, the role of management vision in fast-moving markets, which industries may be disrupted or strengthened by AI, and how large institutions are using AI internally to improve productivity, analysis, and client service. Chapters 00:00 – Intro and episode setup Frazer Rice introduces the episode, frames AI as a dominant investment theme, and welcomes Kevin Shea to help unpack AI Investing for the audience. 01:00 – Hype versus disciplined investing Kevin explains that disciplined investing is what allows investors to separate hype from durable opportunity, and argues that AI adoption, spending, and earnings revisions point to real underlying fundamentals. 03:00 – How to bucket AI investment themes The discussion turns to how investors can organize AI exposure, including beneficiaries versus disrupted companies, technology bottlenecks such as GPUs and networking, and industry adoption themes across sectors. 05:30 – Valuation, momentum, and free cash flow Kevin discusses why free cash flow per share growth remains one of the most important drivers of stock performance and why parts of the semiconductor ecosystem may deserve a valuation re-rating. 08:15 – Circular financing and risk in the AI ecosystem Fraser asks about the growing concern that AI companies are financing one another, and Kevin outlines both the bullish “escape velocity” case and the downside risk if business models do not become independently profitable fast enough. 11:45 – Infrastructure buildout and competitive uncertainty Using analogies like railroads and golf courses, the conversation highlights the risk that early builders may not be the ultimate winners, especially in a market with heavy spending and rapid leapfrogging among competitors. 13:00 – AI Investing: Public versus private market exposure They examine whether owning public companies such as Alphabet offers meaningful AI exposure, versus gaining more direct but harder-to-access exposure through private investment vehicles. 15:45 – What strong AI management teams look like Kevin emphasizes that in an environment with no clear historical playbook, vision, execution, and the ability to identify durable differentiation are critical traits in management teams. 19:15 – Adaptability and strategic pivots Fraser adds that thoughtful adaptation matters, and Kevin notes that sometimes acquisition activity can signal whether a company is innovating ahead of the curve or scrambling to catch up. 20:45 – Which industries are most exposed to disruption The conversation shifts to sectors under pressure, especially parts of software and IT services, while stressing that disruption does not necessarily mean extinction. 24:45 – Why law and accounting may evolve, not disappear Fraser offers a contrarian view that AI may make strong legal and accounting professionals more valuable, and Kevin compares that to earlier fears that Excel would eliminate accountants. 26:15 – How Kevin uses AI in practice Kevin describes how AI has made his team materially more productive, especially in data aggregation, scenario analysis, industry research, and portfolio risk work, while also helping BNY operationally across onboarding, security, and client communication. 29:10 – Where to find Kevin and closing remarks The episode closes with Kevin sharing where listeners can connect with him and Fraser noting how quickly the AI landscape continues to change. Links KEVIN SHEA on Linkedin RICK FERRI on BRING SIMPLICITY BACK TO INVESTING Transcript of AI INVESTING Frazer (00:01) Welcome aboard, Kevin. Kevin Shea (00:03) Yeah, thanks for having me. Appreciate it, Frazer. Frazer (00:06) We’re going to tackle two words that have basically taken over the investment world for the last six months: artificial intelligence. Before we do that, whether it’s AI or crypto or tulips or anything with a lot of hype or buzz around it, how do you think about delineating between investing based on hype and doing it within the confines of a disciplined approach? Kevin Shea (00:32) They really do go hand in hand. You need a disciplined approach in order to recognize whether it’s hype or not. The reality is that it’s pretty impressive, the adoption we’re seeing with AI: the amount of spend, the companies that are participating in and benefiting from AI. There was some concern with the stock movements that many of these companies have seen about whether the market was getting ahead of itself. Yet we have seen significant estimate increases throughout the year. If you take a look at some of the networking companies, their earnings expectations for 2027 are up almost 50% versus where they were just six months ago. The same is true with memory, GPUs, and CPUs. Fundamentally, we’re seeing a lot of these companies have expansion in revenue growth and earnings growth, which is quite supportive of a durable trend. What’s also very important is that adoption of AI is increasing. You can look at enterprise adoption: nearly two‑thirds of enterprises pay for an AI service. You can look at token usage — that’s how much companies are using AI — and that has been parabolic as well. Look at the revenue generation of these AI models. Right now, they are some of the largest, fastest‑growing companies that have ever existed. So we don’t really see this as a tulip scenario, or even comparable to the internet bubble. We find it very different. We think there are fundamental drivers to this trade, and we’re seeing that through earnings growth. Frazer (02:37) Cool. AI to me is a term that encompasses a lot of different things, and in some ways it’s become like real estate or water — it’s starting to touch a lot of different industries. It’s not just a thing unto itself, but something that’s becoming integrated into a lot of other types of things. How do you define and bucket the investment themes so that it’s digestible for the investor, and it’s not just, “I’m investing in Anthropic or Google,” but people can parse out where it fits within a portfolio? Kevin Shea (03:14) It’s a great question and probably one of the most important ones. Part of our overarching thesis is that for AI to fulfill its promise, it has to be in every geography, in every industry, at every company, and at almost every employee layer. We’re seeing that when you look at the business units that are adopting AI: customer service, product development, marketing — basically divisions that almost every single company in every geography has. You phrased it as water, how it touches everything, and we’re seeing that. So how do you segment it? There are a number of different ways: First, you can break it into: who are the AI beneficiaries, and who are those that will be disrupted by AI? Second, you can break it down into different bottlenecks. That’s a way I frequently use within the technology landscape: GPUs, CPUs, memory, networking, storage, data centers. Then you look at that framework and see which companies are most exposed to those bottlenecks. Third, you can ask: which industries will benefit from adoption? Is that biotech, transportation, warehousing? Which companies could be more negatively influenced — maybe that’s software? That’s how we try to create an AI Investing framework for where we should focus our investment efforts and determine the allocation that our clients can benefit from. Frazer (05:17) As we dive a little bit into how you’ve bucketed these themes across different areas, there’s the concept of benefiting from momentum or valuation versus maybe the cash flow and fundamentals of these different investments. I could imagine that, with the hype and mania around the space, there’s a lot of interest. How do you temper that valuation play versus analyzing what the cash flows look like? Kevin Shea (05:49) One of the most highly correlated metrics to stock outperformance is free cash flow per share growth. That’s often the most important metric, and we watch that heavily. What’s incredible — and we talked about this earlier with estimate revisions — is that many within the AI ecosystem are generating extremely healthy free cash flow growth and margins. A lot of that is in AI infrastructure. They’re being paid to supply all the equipment and semiconductors. There’s also this concept that valuation multiples shift to where there’s value creation. I’ll give an example: The SOX, the semiconductor index, used to trade at parity with the S&P. But there’s been a paradigm shift. A lot of the intelligence that’s being created through these models is powered by semiconductors, networking, packaging, and hardware. You’ve seen semiconductors go from trading at parity to trading at almost a 50% premium. At the same time, the market is intelligent; it’s shifted its view of software. Software used to trade at a 70% premium, and we think the intelligence layer has moved just one layer above where software applications normally sit. As a result, you’ve seen valuation compression for the IGV, the software index, from that 70% premium down to about 20%. Some people might look at the semiconductor index and say it’s more expensive than where it historically tr

For many, college success seems pre-ordained and the rightful outcome of a thoughtful next generation development plan, But, we all know this isn’t always the case. One of the great fears for many families is a child stumbling with their first taste of independence and outside accountability. LAURIE DHUE shares insights on preparing young adults for college, focusing on the four S’s: sex, substances, self-esteem, and scholastics. This episode offers practical advice for parents and students to navigate independence responsibly and confidently and set those students up for college success. In recovery for 19 years and with a career in broadcast journalism at the highest levels, Laurie is one of the foremost experts in the field and armed with real world, personal experience. https://youtu.be/8JN2iM8gxWA Key Topics The four S’s framework: Sex, Substances, Self-esteem, Scholastics Importance of consent and online safety Managing peer pressure and peer influence Building self-esteem in the age of social media Practical safety tips for college students The role of family communication and support Long-term decision making and goal setting in college Recognizing signs of substance abuse and mental health issues Guest Name: Laurie Dhue Titles The 4 S’s of College Success: Sex, Substances, Self-Esteem, and Scholastics How to Prepare Your Kid for College: Essential Tips from Laurie Dhue College Success Sound Bites “Consent is the most important thing to discuss.” “Social media creates so much pressure on young people.” “One bad decision can lead to a tough time.” Chapters 00:00 Introduction to Recovery and Wellness 03:06 The Four S’s: Preparing for College Life 06:05 Navigating Consent and Relationships 08:50 Substance Awareness and Safety 11:58 Building Self-Esteem in College 15:42 Academic Success and Responsibility 28:49 Financial Literacy and Practical Majors 33:47 Final Thoughts and Key Takeaways Resources Family Wellness First Program – https://familyofficegrowth.com Laurie Dhue on LinkedIn – https://www.linkedin.com/in/lauriedhue/ Laurie Dhue on Instagram – https://www.instagram.com/lauriedhue/ Family Office Growth Partners – https://familyofficegrowth.com College Success Guest Links LinkedIn – https://www.linkedin.com/in/lauriedhue/ Instagram – https://www.instagram.com/lauriedhue/ The Citizen Heir Concept Transcript Preparing Kids for College: The Four S’s Framework Featuring Laurie Dhue | Hosted by Frazer Frazer: Welcome aboard, Laurie. Laurie Dhue: Great to see you. Thank you so much for having me on, Frazer. Frazer: It’s a pleasure to have you. Today we’re diving into an important topic: preparing kids for the transition to college and setting them up for success. You’ve had a remarkable career in broadcast journalism, and you’ve also been open about your personal journey with sobriety. Can you share a bit about your background? Laurie’s Background and Mission Laurie Dhue: I’m always grateful to talk about recovery and how sobriety can positively impact individuals, families, and communities. I’ve been sober since March 2007—so 19 years now. Sobriety has given me everything back, plus entirely new purpose and additional careers beyond television news. For the past year, I’ve been focused on building health and wellness resources for individuals and families—covering physical, mental, emotional, and spiritual health. Through my work with Family Office Growth Partners, we created a program called Family Wellness First, which provides high-level resources to help families maintain purpose, preserve legacy, and operate at their best. The College Transition Challenge Frazer: We talked beforehand about how this work applies to many areas, but one that deserves more attention is preparing kids for college. You’ve framed this around the “Four S’s.” Walk us through that. The Four S’s Overview Laurie Dhue: The Four S’s are: Sex Substances Self-esteem Scholastics College brings freedom, independence, and opportunity—but also risk. For many students, it’s the first time making decisions without parental oversight while navigating relationships, substances, schedules, and academics. 1. Sex: Consent and Boundaries Laurie Dhue: Consent is the most important concept. It must be clear, ongoing, and voluntary. It can be withdrawn at any time. Young men need to understand responsibility for ensuring mutual comfort. Young women need to understand that attention or kindness does not create obligation. Alcohol complicates this significantly by lowering inhibitions and increasing risk. It’s also important to understand that sex is not a reliable source of validation or self-worth. Practical guidance includes: Use protection Communicate plans with friends Stay aware of surroundings Know campus resources (health center, security, emergency services) 2. Substances: Risk Management and Awareness Laurie Dhue: Substances can derail judgment, safety, relationships, and academic performance—especially early in the first semester. Key guidance: No pills, no powders (due to fentanyl risk) Be cautious with alcohol; it impairs decision-making Never accept drinks you didn’t see prepared Warning signs of a problem include: Obsessing over the next opportunity to drink or use Repeated negative consequences with no behavior change Missing classes or experiencing memory gaps Friends expressing concern Students should have prepared ways to say no and understand that not everyone is engaging in heavy substance use. 3. Self-Esteem: Identity and External Pressure Laurie Dhue: Social media has intensified comparison and pressure around appearance, lifestyle, and status. Ways to build self-esteem: Attend class consistently Tell the truth Leave uncomfortable situations Treat others with respect Make decisions you can live with the next day Support systems are critical: Friends Extended family (aunts, uncles, mentors) Counselors and campus resources Asking for help is a sign of strength, not weakness. 4. Scholastics: Discipline and Structure Laurie Dhue: Freedom in college requires discipline. No one is managing your schedule, so students must build structure early—especially in the first semester. Key habits: Prioritize sleep, nutrition, and exercise Review notes regularly Start assignments early Use planners or digital calendars Seek tutoring when needed Discipline is a form of self-respect. Financial and Academic Practicality Frazer: Students should balance curiosity with practicality—developing skills that translate into career opportunities. Avoid unnecessary debt and understand basic financial concepts like compounding. Even small financial decisions can have long-term consequences. Laurie Dhue: Agreed. Use debit cards where possible, avoid unnecessary credit, and think carefully about major purchases. Practical majors today include: Nursing Accounting Engineering Computer science Finance Supply chain and operations Information systems Students don’t need to decide immediately, but they should move toward a viable path. Final Takeaways Laurie Dhue: One poor decision can have lasting consequences Small decisions compound over time Asking for help is a sign of maturity College is about learning to manage freedom—not proving independence through risk-taking Trust your instincts—if something feels off, it likely is Where to Find Laurie Laurie Dhue: LinkedIn: Laurie Dhue (Family Office Growth Partners) Instagram: @LaurieDhue Facebook: Laurie Dhue I’m always happy to connect and help families navigate mental health and substance use challenges. Frazer: Terrific. Thanks for being on. Laurie Dhue: Thanks, Frazer. Keywords college prep, young adults, self-esteem, substances, consent, college safety, mental health, family wellness https://www.amazon.com/Wealth-Actually-Intelligent-Decision-Making-1-ebook/dp/B07FPQJJQT/

Citizen Heir: How Engaged Citizenship Helps Solve The Three Generation Rule Destroying Most Wealthy Families https://youtu.be/yyt4d271lSU Citizen Heir Successful families right now are struggling mightily to raise their kids to be productive, moral people in an Instagram me‑first world. The question I keep hearing from parents who are serious about it is, where do you turn when achievement gets measured in dollars and likes? The stories of ruined generations are as old as time itself. There’s even a phrase for it: “shirt sleeves to shirt sleeves in three generations.” Every culture has a version of that saying, and they all mean the same thing. The question I keep coming back to is, why do some families break that pattern when so many others don’t? The ones who do almost always took seriously something harder than drafting a good estate plan. They took seriously the job of raising a good heir. And today, I want to share a concept that comes back constantly in those conversations I have with clients. I call it the “citizen heir.” Citizenship has been on my mind a lot lately with America’s 250th birthday coming up. We live in divided times, and the discourse around civic responsibility has suffered for it. Many people feel the core ideas and institutions are no longer worthy of their trust. We’ve become loose from our moorings. That might sound like a political observation, but it’s actually a family one. Because when you strip away the noise, what families with significant wealth are really doing is trying to transmit values alongside resources. And that’s exactly where most of them run into trouble. They get very close to the money, and sometimes in the process, they forget the values part. Here’s the connection I keep making. A good citizen and a good heir are operating under the same moral logic. A good citizen doesn’t treat rights as pure entitlement. They understand they’ve received something they didn’t fully build. It could be a society, a tradition, a set of institutions, yet they’re responsible for what they do with it. A good heir works exactly the same way. Wealth isn’t a possession, it’s actually a trust. In Jewish, Christian, and Islamic traditions, this idea is ancient. Wealth is treated as something given for service, not self‑indulgence. A faithful person uses what they receive with humility, with charity, and with accountability. The good heir honors the giver by using the inheritance wisely. Both are tests of whether a person can handle a gift without becoming enslaved by it. Politically, a good citizen sustains the republic, not just by obeying laws, but by defending institutions and resisting the pull toward passive entitlement. A good heir does something analogous within a family. They preserve capital and avoid waste. They use resources in ways that strengthen something larger than themselves over time. In both cases, the person is a custodian of an order that predates them and should outlast them. Citizenship without duty is just a passport. Inherited wealth without responsibility is just a balance. Both require something from the person holding them, or they stop meaning anything at all. Neither the citizen nor the heir chose the structure they were born into, but both are answerable for what they do with it. The good citizen and the good heir each prove something to themselves by converting privilege into obligation, and obligation into something durable. A family’s educational efforts have to acknowledge that reality. Preparing an heir isn’t a side project. It deserves as much attention as any other part of the plan. https://www.amazon.com/Wealth-Actually-Intelligent-Decision-Making-1-ebook/dp/B07FPQJJQT/ https://frazerrice.com/10-family-office-myths-exposed/ https://www.jamesehughes.com

The New CEO Social Media Playbook: Communications Strategies in the Digital Age for the Modern CEO. In this episode, TED MERZ from Principals Media discusses the seismic shifts in corporate communications, exploring how CEOs can build authentic visibility in a rapidly evolving digital landscape, and the future of traditional media. https://open.spotify.com/episode/6MLjRILrkeCPhlG6ItXaMC?si=uQP9CdYORpmr89iL4dfMvg https://youtu.be/clHzhrOZAps Key Topics The decline of traditional PR channels like CNBC and The Wall Street Journal and the rise of direct content creation for thought leadership. The importance of authenticity and transparency in CEO messaging, with real-world examples such as McDonald's CEO controversy and insights into crisis management. Strategies for leveraging social media platforms—LinkedIn, X (Twitter), YouTube, and emerging tools—for building personal and corporate reputation. The evolving role of AI in shaping search results and online identities, emphasizing the need for content influence. The significance of visibility across multiple channels and the concept of the “public record” for professional branding. Balancing platform choice with audience targeting and the importance of integrated content strategies. The future of content formats: long-form videos, short clips, point-of-view storytelling, and the normalization of CEO participation in digital media. Traditional media’s ongoing role in establishing credibility within a pyramid of influence, from legacy outlets to influencer-generated and user content. Timestamps: 00:00 - Introduction to CEO communications in the digital era02:00 - The decline of traditional media outlets for corporate messaging05:00 - Case study: McDonald's Big Arches video controversy and lessons learned07:30 - Why engagement in digital platforms is no longer optional for CEOs09:00 - Platform strategies for business communication and audience targeting11:00 - The future role of CEOs on YouTube and social video content13:00 - Authenticity and AI’s impact on content credibility15:00 - Cross-platform content distribution and emerging channels like Substack16:00 - Measuring success: from vanity metrics to real business impact17:00 - The complexity of linking social media efforts to sales and hiring outcomes19:00 - Building visibility to enhance reputation and company valuation20:30 - The importance of a balanced media approach—traditional and digital22:00 - Influencer dynamics, user-generated content, and organic reach24:00 - The societal shift towards individual visibility and personal brand26:00 - The relevance and future of traditional media in a digital-first world28:00 - Strategies for influencing AI-driven search and online biography management29:30 - How organizations can foster authentic employee advocacy30:50 - Resources to connect with Ted Merz and his ongoing projects Resources & Links: Principals Media Pricing Culture — The Bloomberg for Collectible Data LinkedIn X (Twitter) YouTube Substack Connect with Ted Merz: LinkedIn Twitter Insights: CEOs should view digital visibility as a fundamental communication muscle. The importance of integrating long-form content, short clips, and authentic storytelling. The shifting landscape where legacy media remains valuable for credibility, but influence is increasingly driven by digital presence and influencer narratives. BRAM WEINSTEIN ON "BREAKING THROUGH DIGITALLY" https://youtube.com/shorts/Ia_X8A_WhG4?feature=share Transcript Why CEO Communication Is Changing Frazer Rice:Welcome back to the Wealth Actually Podcast. Apologies in advance for the head cold. I’m joined today by Ted Merz of Principals Media. We’re discussing how CEOs are navigating communications, the role of social media, and whether traditional media is still relevant. Frazer Rice:Ted, welcome. Ted Merz:Great to be here. Thanks for having me. Frazer Rice:We met at a dinner in New York, and I was struck by your perspective on the shift happening in PR. You advise CEOs on communications—what are you seeing? Ted Merz:We’re in the middle of a major structural shift. Traditionally, companies relied on PR firms to secure placements in outlets like CNBC or The Wall Street Journal. That’s becoming less effective—those platforms are more competitive, often paywalled, and in some cases shrinking. Ted Merz:At the same time, more people want access to that exposure. So companies are going direct—creating their own content through social media, podcasts, video, and written thought leadership. It allows them to bypass traditional gatekeepers and control their narrative. Risks, Authenticity, and the Learning Curve Frazer Rice:It also gives you more room to develop your ideas. But we’ve seen cases—Sam Altman, for example—where messaging goes sideways. Is that inexperience or the format? Ted Merz:It’s not the format. There’s always risk in speaking publicly—people can react negatively. Sometimes it’s inexperience, but more broadly, this shift is inevitable. Ted Merz:If you want to reach younger audiences—late millennials and Gen Z—they’re not watching CNBC or reading newspapers. They’re on YouTube and Instagram. So participation in digital media isn’t optional. Ted Merz:That said, there’s a learning curve. Executives aren’t always comfortable, and mistakes will happen. Frazer Rice:Just look at the reaction to a poorly thought-out tweet—it can spiral quickly. Ted Merz:Exactly. But opting out is the bigger risk. If you’re not visible, you’re not part of the conversation. Choosing Platforms: LinkedIn, X, YouTube, Substack Frazer Rice:I’ve leaned into that with this podcast and more activity on LinkedIn and Twitter. But there’s a tension—should you focus on one platform or meet clients wherever they are? Ted Merz:It’s not about the platform—it’s about communication. You’re either writing or creating video. Ted Merz:For most businesses, LinkedIn is the best starting point. It’s professional, relatively forgiving, and widely accepted. But platforms are evolving quickly. Ted Merz:For example, X (Twitter) is now supporting long-form content—5,000+ word essays—and has become a hub for thought leadership in finance and tech. It’s more intense and less forgiving than LinkedIn, but that may be where your audience is. Frazer Rice:That’s part of why I moved my podcast to YouTube. If you’re not on YouTube, you’re invisible to Google. But not everyone is comfortable on video—how do you handle that? Why Video and YouTube Matter for CEOs Ted Merz:I tell them to get comfortable. Ted Merz:YouTube is the new television. It’s where attention is going, and it rewards creators financially. Companies need to develop video capability. Ted Merz:Written content conveys ideas well, but video builds trust and familiarity. That’s critical today. Ted Merz:Historically, CEOs didn’t communicate this way. But now you see leaders like Mark Zuckerberg, Jamie Dimon, and Jon Gray using video regularly. That legitimizes it. Within a few years, this will be standard. Frazer Rice:There’s also a push for authenticity. Overproduced or AI-generated content feels hollow, especially with growing fatigue around corporate messaging. Ted Merz:That’s right. But authenticity doesn’t mean abandoning standards. You can still communicate clearly and thoughtfully. Ted Merz:Also, content is increasingly distributed across platforms—LinkedIn, X, YouTube, Substack. Substack, in particular, is emerging as a strong platform for serious thought leadership. Ted Merz:Importantly, in business, the goal isn’t to go viral. It’s to create a credible public record—so when someone looks you up, they see someone thoughtful and worth engaging. Measuring Impact: Beyond Vanity Metrics Frazer Rice:That raises the question of metrics. How do you connect social media activity to actual business results? Ted Merz:It’s difficult. Social media behaves more like brand advertising than direct response marketing. Ted Merz:Vanity metrics—likes, shares—can be misleading or manipulated. The connection to revenue is often indirect. Ted Merz:But you can see impact anecdotally. One client told me they couldn’t tie posts directly to sales, but they were attracting better job candidates who already understood and trusted the firm. That’s real value. Frazer Rice:And what about search? It used to be about controlling Google results. Now with AI-driven search, that’s changing. Ted Merz:Exactly. Large language models now shape how people are perceived online. You can’t fully control that, but you can influence it by consistently publishing clear, factual content. Ted Merz:If you don’t, the narrative will be created without you. Personal Brand, Corporate Brand, and Goodwill Frazer Rice:I think of this as building personal and corporate goodwill—like managing the name on the back of the jersey as well as the front. Ted Merz:That’s a great way to put it. Ted Merz:We’ve also seen a cultural shift. In the past, companies emphasized the collective—“there’s no I in team.” Today, we’re in an attention economy where people connect with individuals more than institutions. Ted Merz:That’s why CEOs are becoming more visible. It helps the brand, and it reflects how audiences engage. Ted Merz:Companies are also trying to involve employees, but that’s tricky—you can’t fully control messaging and still have authenticity. Frazer Rice:Which brings us back to the core tension: authenticity versus control. Ted Merz:Exactly. Is Traditional Media Dead? Frazer Rice:So is traditional media dead? Ted Merz:No—but its role has changed. Ted Merz:Think of it

ALEXANDRIA SEYDEL from Ripples Edge Advisors shares expert strategies on "getting the business ready to sell." We focus on exit planning and getting the most value out of the transaction. Discover how early planning, owner mindset, and strategic positioning can lead to successful exits and satisfied owners. https://youtu.be/8OwhCRCBZl4 https://open.spotify.com/episode/2qawd64OYzljBvU9xqS8df?si=1Xvv2OUFSbeBtUDeJGTMXg KEY TOPICS Early exit planning and owner mindset,Getting the business ready for sale and transfer.Risk assessment and deal readiness.Owner satisfaction and post-sale happiness.Capital raising and growth strategies. SOUND BITES for "GETTING THE BUSINESS READY TO SELL" "Getting clear on owner success is crucial.""Start exit planning 2-5 years in advance.""Family dynamics can be deal breakers." Chapters 00:00 Navigating Business Exits: An Introduction.02:57 Understanding Owner Satisfaction Post-Sale..05:55 Preparing for Sale: The Importance of Readiness.09:00 Building a Succession Plan for Business Continuity.11:49 Assessing Business Value: The Exit Readiness Assessment.15:08 Evaluating Growth Opportunities and Capital Needs.17:58 Cash vs. Equity: Making Informed Decisions.21:03 Finding the Right Buyers: The Role of Advisors.24:08 Addressing Family Dynamics in Business Sales.26:59 Checklist for Business Owners Considering Sale. RESOURCES Ripples Edge Advisors - https://ripplesedgeadvisors.com/ GUEST LINKS LinkedIn - https://www.linkedin.com/in/alexandriaseydel/ QSBS For Founders - https://frazerrice.com/qsbs-for-founders/ TRANSCRIPT Frazer RiceWelcome aboard, Alex. Alexandria SeydelHi Frazer, so nice to be here. Thank you for having me. Frazer RiceThank you for being on. We're at a time now with the economy where it feels like it's roaring. Valuations on things are going up, up, up. And people who have founded businesses are exploring their options. That's kind of where you step in with your firm Ripple's Edge Advisors. Talk to us about what you do to help founders get ready. Not only in understanding what they have in their own business. How to go through the daunting process of exploring their options. Getting their business bulletproof for when people start looking under the hood. Alexandria SeydelAbsolutely. My background is as an M&A attorney, so I came from the deal side. My co-founder is an operator — she actually knows how to run the businesses. It's a very good duo. I think like a buyer, first and foremost. That's how I was trained. So how we help business owners now is we jump in two to five years before exit. We're trying to solve a problem still being missed by most of the industry. Brokers and bankers know how to get deals done, create auctions, create demand, and sell for high prices. That's all great. But the gap I was seeing was the need to jump in with the owner before that process. Getting clear on what's a win for them. There are some startling stats about owner dissatisfaction post-sale. Some surveys show 70 to 80% of owners are dissatisfied after selling. I'd argue that's not because they sold — it's because they sold to the wrong person in the wrong way. So it's the who and the how. Jumping in with them earlier. Before we go to market, Before we start talking multiples and financials. Getting with the owner and doing the work on what a win looks like for them. What do they care about in the process? When they think about their life through this deal and post-deal, what do they want to feel and see? How do they want to operate on an average Tuesday. Yes, after all the cool vacations with all the freedom and the new chapter. After that, what do you want to be doing? And when you look back at that beautiful business you built and then sold, what do you want to see in it? Is it that client service remains the same? Is it that the ethos of the company remains the same? Or is it simply: "Alex, I'm satisfied with the biggest wire at closing we can get, and I'll be a happy camper moving on to the next phase of life." Really getting with that owner earlier to get clear on that — what's a win for them and what's a win for their business — that's where we start. Then we begin implementing and helping them build those exit strategies from there. We believe that foundational vision and values work is really going to help bring down that dissatisfaction number. So now we're building an exit that feels right for the owner, right for the business, and helps them feel good about that transaction. Frazer RiceFrom the estate planning and tax planning side of things, I totally agree that the earlier you start, the more tools you have at your disposal and the better it turns out. I did a piece on pre-exit planning — really engineering what your calendar is going to look like a year after the sale. And I see a lot of dissatisfaction with people who sell and then lose purpose, or aren't quite equipped to deal with their lower participation in the thing they built, the baby they helped give birth to. They end up unmoored, and that's part of the depression they sometimes feel if they haven't really gamed it out and thought through how to replace the structure and the drive it took to build something. It sounds like we're saying the same thing from slightly different angles. Alexandria SeydelTotally, absolutely. On your side, you're such a critical part of the team when we start this process. One of the first two questions we ask every client is: who's your wealth advisor, and who is your tax strategist? Hopefully they're already in communication, but if they aren't — you're looking at the personal side, focused on what the family structure looks like financially, the tax strategies and planning that we know has to happen. And because you're doing this work — which not all advisors do — you're getting really clear on the personal side. I'm coming at it from the business balance sheet and business trajectory; you're coming from the personal side. They work well together. I like to jump in early with the other advisors working with these owners to get really clear, because not only do we know there are structural and strategic things we need to put in place years in advance, but we also need to get clear on what's a win for them personally and business-wise. Frazer RiceOne of the things you mentioned is the idea of getting the business ready to be sold. I'm fast-forwarding to the concept of getting it Sarbanes-Oxley ready in case a public company wants to buy it — so it can slot neatly into a balance sheet. But that's really shorthand for saying things are professionally managed: bookkeeping, process, accounts receivable, accounts payable — all formally documented. So that when a buyer starts looking under the hood, they don't start applying discounts for things they'll have to fix later. Is that part of what you do? Alexandria SeydelExactly. Being trained as a lawyer on the buy side, my goal — usually at the 11th hour — was to advise my client, the buyer, on risk. And to assess whether the purchase price offered in the letter of intent actually held up once we looked under the hood. The best part of my job now — and way more fun — is that instead of just identifying risk and applying discounts (because almost every deal goes through some form of repricing), I'm jumping in with the sellers and owners hopefully a year or two in advance. We find things a buyer is going to see as a risk, things that would prompt a reprice, and we now have the opportunity to make those things shinier. So that when the buyer looks under the hood, the high end of the multiple range is validated. It's not just the financials the purchase price is based on — it's all the other things buyers care about: the people, the processes. Is this a truly transferable asset they can step into, run, and grow? Another big thing we work on is owner dependence. Most owners think the business doesn't depend on them, but there are often significant opportunities to continue reducing that dependence — so that a buyer sees this as a true transferable asset they can step into and grow. Frazer RiceI imagine there are a couple of come-to-Jesus discussions where you have to tell the owner their revenue is too dependent on them personally. On one end of the spectrum, think of a law firm where business comes in because people think you're a great lawyer — that doesn't transfer cleanly. You want the recurring revenue to come from somewhere else. That's one issue I'm sure you have to sit someone down and address. The five-year runway is helpful there — it gives you time to build in a succession plan, not just for the sale, but operationally, so that value still sits in the business whether you're there or not. The second thing I find interesting is where you sit somebody down and say: this would look a lot better if you took less money out of the business. If we can put that back into EBITDA, then when a buyer starts applying multiples, they're multiplying against something bigger rather than against a number deflated by, say, buying a boat. Do you get into that conversation? Alexandria SeydelYes, we do, and we take a cursory look at that fairly quickly. Then we bring in support if needed — whether that's on the accounting side, how money flows through the business to affect the bottom line and create the story. Every buyer wants at least three years of financials; we want that growth story to look strong, and we want to start building it now. If we need to bring in a fractional controller or a fractional CFO depending on the size and sophistication of the business, that's something we pull in right away. On your first point — we actually have an architect client right now at exactly that phase. He has a right-hand woman architect who's been with him for over ten years, and he wants her to have the opp

In a world of noise and distraction, there is a trend in "Bringing Simplicity Back To Investing." RICK FERRI and I talk about why it's important for investments and why it's important for individuals. You're going to leave here understanding a new framework for looking at your investment portfolio and hopefully bring some peace of mind as you go forward. https://youtu.be/8EFnt_UTjEA Rick Ferri has been a good friend to the podcast. He shares his insights on simple investing, emphasizing the importance of clarity, discipline, and understanding the core principles of investing. He discusses the pitfalls of complexity, the value of index funds, and how to maintain a disciplined approach amidst market noise. https://open.spotify.com/episode/743dxOLLgZjUzKszZo4Owy?si=57mqK1ZmQ0a7LPdcwVoQ-g Keywords investing, index funds, simplicity, portfolio management, financial planning, discipline, asset allocation, tax efficiency, global growth, investment philosophy Key topics The philosophy of simple investingThe stages of investor learning: darkness, enlightenment, and simplicityThe importance of cash flow and intrinsic value in investmentsAsset allocation based on liabilities and time horizonTax-efficient investing strategies for taxable and retirement accountsRisks of alternative investments and private equity in retirement plansDiscipline and automation in maintaining investment strategies Chapters of "Bringing Simplicity Back to Investing" 00:00 The Philosophy of Simple Investing07:03 Stages of Investment Understanding11:19 Financial Planning and Purpose17:57 Implementing a Simple Portfolio23:01 Discipline in Investing30:46 Navigating Complexity in Wealth Management Resources Rick Ferri's Website - https://rickferri.comBogleheads.org - https://bogleheads.orgIndex Fund Book by Rick Ferri - https://www.amazon.com/s?k=Rick+Ferri&ref=nb_sb_noss_2 Website - https://rickferri.comTwitter - https://twitter.com/RickFerri Skeptic's Guide to Investing Outline: "Bringing Simplicity Back To Investing" Introduction: Three parts to simple investing: Philosophy, Strategy, Discipline Part 1: Philosophy: Overview: Embrace Simplicity - the Education of an Index Investor - 4 stages 1: Born in Darkness (who you ask, chasing returns, naive research) 2: Finding Enlightenment (measure, compare, enlightened) 3: Complexity Traps (slice’n dice, factors, the fallacy of perfection) 4: Embrace Simplicity (global equity, specific fixed-income as needed) Part 2: Portfolio Strategy Overview: Making the Philosophy Work for You 5: Setting Goals (family - culture, career – taxes, risk tolerance) 6: Managing Risk (three ways to allocate assets: required return, risk avoidance, cash-flow) 7: Tax Management (three account types, asset class tax, tax avoidance) 8: Investment Selection (ETF vs fund, balanced funds & TDFs) Part 3: Discipline: Overview: Implement, automate, stay the course 9: Implement fully (consolidate, tax issues, lump sum vs DCA) 10: Maintain regulatory (automate new, rollovers, TLH) 11: Adjust as goals change (accumulation vs distribution, tax situations, legacy) 12: Stay the Course (recommit occasionally, continue ed., conferences) Transcript of "Bringing Simplicity Back to Investing" Frazer Rice (00:00.962)Welcome aboard, Rick. Rick Ferri (00:02.3)Well, thank you for having me. Frazer Rice (00:04.258)Well, thank you. First of all, want to thank you for a kindness you showed me way back in time and having me on the Boggleheads podcast. It was probably worth at least 25 % of my book sales and it was a lot of fun to do and never forgot it. So it took a while, but here we are back on my podcast. And what I want to do is go through a little bit about really the three parts to simple investing, which I think is something, especially now with the proliferation of alternatives, a lot of noise with crypto. That sometimes we kind of lose sort of the forest for the trees as far as what's the right things to be thinking about in terms of an overall investing philosophy sort of embrace. And so maybe let's start with that. How do you think about the parts to a good investing thesis and what is your overall worldview on that? Rick Ferri (00:55.804)So I've been in the investment advisory industry now for 40 years. And what I have learned is that the simpler you can make investing and the simpler you can make the portfolio, the better for you, the better for your family, the better for those who will inherit your portfolio. Don't make it complicated. Complexity is just job security for those people who are selling you things and trying to manage your money. And in the end, you don't benefit from that. They do in the form of fees. And if you just had a simple portfolio of a few good index funds and maybe some individual securities, you'll be much better off and your family will be better off in the long term. And that's the philosophy of simple investing. Frazer Rice (01:50.947)Mm-hmm. Rick Ferri (01:53.208)The second part is a strategy. How do you go about doing this, particularly if you've had a complex portfolio? And the third thing is discipline, which is how do you stick with simplicity as an investment philosophy? Frazer Rice (02:06.318)Sure. and without the second two, it's great to have high-minded thoughts and so on, but if you can't do it, it's all for naught, and then if you can't stick with it, then the best laid plans just kind of go asunder here. So let's go back to the philosophy for a second here, and as you think about, it's almost like the life cycle of discovery and learning about how these things work. How do you think about that from an ARC perspective? Rick Ferri (02:12.561)Ha ha. Rick Ferri (02:36.05)So generally when you're new to investing, you're going to ask other people for advice. I where you get that from, might be a friend or family member, maybe a professional advisor, might be coworkers, maybe you'll just get on the internet and start searching. I don't know, but 99.9 % of the time you're gonna run into advice that is not very good. And the advice will be, you should put your money here, you should put your money there. Use these 10 different funds. It's just a lot of confusion, quite frankly. I call this stage darkness because you don't, you you're just investing in the dark. You don't know. And a lot of the advice is going to be very short based upon short-term performance. So recency biased people are going to be recommending, but you know, growth stocks because the Magnificent Seven has done well in the past. Or buy crypto because crypto went up a lot in the past and so therefore you should buy it now. And so most of the advice you'll get in darkness is going to be recent based upon recent performance and rather than looking at it over say how should you be investing over 10, 20, 30 years and that will end up being quite different. So darkness is where we all begin. And most people stay in darkness. They never get out of darkness because they don't put the brain cells to work to look at how am I doing? I mean, how has that done for me? What seems to be happening in my portfolio? Really? Do I really know what's going on? And then the ones who are very fortunate start asking questions about, what if I just Frazer Rice (04:06.125)You Rick Ferri (04:31.334)bought the market and bought an index fund and just got the return of say the US stock market or the international stock market and that's all I ever did. Would I be better off? And the answer to that 98 % of the time is yes, you would be better off if that's all that you did. And if you come to this realization, I call it the second stage, which is enlightenment, where you now realize that, okay, all the stuff I've been doing may have been okay. I've been moving in and out of things, but now I need to start looking at just buying the market and holding it for the longterm. And that's enlightenment. But for some people, it doesn't stop there. And they start to dig into this idea of indexing. When you start doing that, it's good that you're learning, but you'll start running into a whole lot of noise. That is alternative indexes, enhanced indexes uh… explore strategies all of these things that you're going to take this nice simple concept called indexing and make it complicated again. So you start adding all these things to your portfolio because it has the word index in it or maybe the word passive in it and uh… advisors are notorious for doing this it's called complexity for job security Frazer Rice (05:39.148)Right. Rick Ferri (05:54.066)Basically, are, you know, you take the idea of indexing and you just add a lot of things all around the edges of it and you make a simple portfolio complicated. So the third stage of this process of simplicity is complexity. In other words, you've made something simple complex. Okay, so the last stage is Frazer Rice (05:54.221)You Rick Ferri (06:18.544)Simplicity. That is that you realize this is going on. You realize that all the stuff that you're adding to your portfolio is just making it all complicated again. And that the people who are benefiting from this are not you, but the people that are selling you all this stuff. And you say, that's it, I'm done. I'm going back to my second epiphany, if you will, which is simplicity. I'm just going to go back to a simple portfolio of a few broad index funds, US stock market index fund. An international stock market index fund that covers the whole market and a couple of bond funds, municipal bond fund and maybe corporate bond funds or treasury bond funds. And you could use index funds for those as well. And it's a really low cost, very tax efficient and very simple. Frazer Rice (07:05.953)A couple of quick asides here. The first one is for people who are coming into this in and they're in the darkness,.

This interview explores the critical importance of managing digital assets in estate planning, highlighting the challenges of digital inheritance, account access, and cybersecurity risks. TATYANA THURSTON and NATALIA PARKER share insights on creating effective digital estate plans, tools, and best practices. https://youtu.be/2N56L51cD6Q https://open.spotify.com/episode/01ScInrdux6UOQ0G1kPzNF?si=uiCizZbOTEisa9PJ_D_S5g KEYWORDS: Digital assets, estate planning, digital inheritance, cybersecurity, online accounts, digital executor, wills, estate law, digital legacy, digital estate management KEY TOPICS Digital assets definition and scope Challenges in digital inheritance and estate planning Tools and strategies for digital asset management Legal and cybersecurity risks in digital estate planning Guest Name Tatiana Thurston and Natalia Parker Sound Bites "Biometric security doesn't work after death." "Planning ahead saves hundreds of hours and pain." "Domain name issues can take months to resolve." Chapters 00:00 Introduction to Digital Assets 01:28 Understanding Digital Assets and Their Importance 04:14 Challenges in Estate Planning for Digital Assets 09:17 Navigating Access and Security Risks 13:22 Creating an Inventory of Digital Assets 18:21 Preparing Executors for Digital Asset Management 24:40 Resources and Tools for Digital Asset Planning GUEST RESOURCES DEXITPLAN TRANSCRIPT Frazer Rice (00:01.146)Tatiana and Natalia, welcome aboard. Natalia Parker (00:04.206)Thank you. Tatyana Thurston I Dexit (00:04.211)Hi, thank you for having me. Frazer Rice (00:05.966)We are, this is a new frontier for wealth actually. You are the first two person interview I've done so far. So it looks like the technical issues seem to have gone away. That's great. But we're gonna talk about something that I think is the driver for your new company and something that's important to me because when I'm advising people around a lot of different topics, either estate planning wise or wealth management wise, the digital asset question comes up and. You've formed this new company. Tell us a little bit about that and more importantly tell us the problem that you're trying to solve around digital assets Tatyana Thurston I Dexit (00:40.83)Okay, so I'll first start with what is a digital asset because there's a lot of different definitions out there and a lot of people have different concepts of what it might mean. of all, because crypto is in the news quite a bit, it is not just about crypto. Everybody has digital assets because basically if you are logging into an account and it is storing data, you have an account that has assets online and it could be monetized. It could be social media, which means that the information that's there is very personal to you. It could be that you have reward points you've accumulated. There's all sorts of types of assets that are out there and there is a pain point problem. Let's die down. Natalia Parker (01:28.462)Yes, and we started actually, it was interesting, Tatiana just went through the process of writing a will and she will tell about it. I went through a divorce where we had online business and it was really, really hard to trace all those online accounts because I had no understanding how many we had and what to do with them and how even to find them. And Tatiana wrote a will. Frazer Rice (01:54.67)Yeah, no. so just to put a finer point on that, it's not only the monetary assets and the social media accounts and everything that basically requires a password to get into it probably in this day and age. Natalia Parker (02:10.252)Yes, and I can tell you more than I lost pictures of my family from my daughter's birth to age seven because I didn't think that the iCloud password and iCloud identity gone through a divorce. Yes. Tatyana Thurston I Dexit (02:10.336)That's all. Tatyana Thurston I Dexit (02:26.88)So she can resell for it. Yeah. Frazer Rice (02:26.992)Yeah, and a very painful thing to go through. so, Tatiana, as we sort of look at that example and make the definition a little bit even more in depth, how else do you sort of think about that in terms of the roles that are played from a Will's perspective? Tatyana Thurston I Dexit (02:49.366)So from a will perspective, you have two kinds of entities. You have things where business owners have created online accounts where their business is running off of certain platforms. And you also have a personal side aspect. And it may be an influencer, it may just be your personal account. The thing is that we're dealing with a problem of immortality. And this means that these accounts remain open, active and online, ready for hackers and ready for now, today, AI to continue the trajectory of that account because they're making money off of the data that we've put online. So we actually have two things to look at. One is from the business perspective and how do you transfer a business over? Because maybe you've built a platform for 10 years on Facebook, right? You have a following which is important to your base. Maybe you're just a mom and you've put all your baby pictures on there, like Natalia, and then what is the loss? What is the impact of that loss? And both are really difficult on families. So estate planning means that we actually need to be looking at these accounts, we actually need to be planning for these accounts, because down the line, it's gonna be a heavy impact, whether it's sociological, emotional, or monetary. Frazer Rice (04:14.552)So as we think about this little bit further, the concept that these accounts are going to live on beyond the life of someone who created them. Maybe dive into that a little bit, because I imagine you not only have points of risk, certainly during the lifetime, and someone hacking in and pillaging your bank account or otherwise maybe blocking access or something like that, but what happens when someone passes away? How do those risks translate to the people who are inheriting these properties? Natalia Parker (04:45.258)Okay, let's talk about it. We have those certain pain points. The first one, when somebody dies, the executor or administrator, they don't know what is existence. They don't know what kind of accounts the person had, what they wanted to do with those accounts. That's a first problem because they don't know even what banking, where the life insurance, did they have Venmo because they don't have access to phone. The second one, didn't know what the person wanted to do with that account. Did they want to close, transfer, memorize it? They have no clue. The other one is authority as an executor doesn't mean that you will get automatic access to the account. Many people think that yes, it is. No, for Google it doesn't matter. Unless you were appointed as inactive account manager. The same for Apple. Frazer Rice (05:48.68)I was going to say those annoying terms of services agreements that no one reads and you click so that you get, you move on with life and get into your accounts, that's where some of these details are buried. And the intersection between that and maybe what we call estate law and how an executor works, that's where the friction takes place. Natalia Parker (06:09.43)Yes, I agree and many people don't even know that that feature exists like legacy contact for Meta and Apple or inactive account manager. Otherwise, when you look at the hierarchy online tool, we call it Castonian tool, outweighs everything what you have in wheel. If the online tool wasn't enabled, then it goes what kind of language you had in wheel. if you appointed some digital executor and if that executor was authorized to have access to all your accounts. The third one, it always default to terms of service. Terms of service for basically 99 % of each company says do not give access. Frazer Rice (06:56.09)So if you were stuck and you didn't do anything and you relied on the terms of service, you could be in a really deep set of troubles. They might delete your account, they may not allow access, or they may make it otherwise very difficult in order to access and do it. You think that the person who died with it wanted to have done. Tatyana Thurston I Dexit (07:16.246)That's right. Natalia Parker (07:16.598)Absolutely. Tatyana Thurston I Dexit (07:17.504)That's why some of these really large companies have a custodial tool. You do have to go to certain settings within the device or within the account. And you can enable these tools so that you can either add what could be a legacy contact. It may not have the term beneficiary on it, but it's important to be able to enact that so that these settings will allow certain access down the line. A lot of the companies are very particular about that the larger ones have it and then a lot of them don't so Knowing which company has the most value to you and those terms of service is really important Frazer Rice (08:01.84).For someone who has an account that lives beyond them, there are identity and financial risks to having that. I can imagine, you know, when you put a credit card on file and, it's auto-debated or you have information lurking out there that that's a problem. Maybe talk a little bit about how bad that can get. Tatyana Thurston I Dexit (08:21.517).So I think there's a few issues on that. We all know that there are scammers and hackers. The really important stories that have come out in the past is where AI is enabling recopying your name, image, and likeness posing as you live on a video stream or live on a phone call asking for money or data or information. And this is becoming really prevalent. This is where families, if they want to save and secure their reputational legacy. But also perhaps crypto, perhaps their banking accounts, it's really important that they understand that t

BRADY WELLER discusses the intricacies of QSBS rollovers, including eligibility, timing, and strategic planning for founders and investors. The goal is to help the listener maximize tax benefits and navigate the legal complexities of this powerful tool. https://youtu.be/gvQ0ZskvWVI QSBS, tax exemption, startup founders, rollover, legal structuring, investment strategy, tax planning, startup exit, C corporation, Key Topics QSBS eligibility and benefits Challenges in executing rollovers Legal and tax considerations for founders Timing and risk management in rollovers Strategic structuring for maximum benefit "QSBS ROLLOVERS" Sound Bites "60 days is a very short window for founders." "Rollover continues your holding period clock." "Partial rollovers are common for founders." Chapters 00:00 Understanding QSBS and Its Benefits 03:07 Challenges for Founders in QSBS Compliance 05:54 Advising Founders on QSBS Rollovers 08:57 Structuring New Ventures for QSBS Eligibility 12:00 Navigating QSBS for Tech and Non-Tech Founders 14:54 Investor Considerations in QSBS Transactions 17:46 State-Specific QSBS Regulations and Planning 20:57 Future of QSBS and Strategic Planning Resources Brady Weller on LinkedIn qsbsrollover.com qsbsreference.com Frazer Rice and Michael Arlein discuss the nuts and bolts of 1202 QSBS Features for Founders Guest links LinkedIn Transcript Frazer Rice (00:01.314)Welcome aboard, Brady. Brady Weller (QSBS Rollover) (00:03.043)Hey, Frazer, thanks for having me. Frazer Rice (00:04.738)Well, you are the nice compliment to a piece I just did with Michael Arlene on QSBS. We covered some of the nuts and bolts around 1202. You come at it from a little bit different angle. It's usually where people, founders especially, have issues sort of complying with things like the three and five year rule. And otherwise really maximizing the capability of the rollover and the tax significance for it. Tell us a little bit about who benefits and what you do here. Brady Weller (QSBS Rollover) (00:35.107)Yeah, QSBS is. by far the biggest tax exemption available to individual taxpayers in the U.S. So it's been something that hasn't been up. I should say there's not a massive advisory network around it. So it's not something that's been taken advantage of, I think, to its full scope. Michael, who you had on recently, is a top trust and estate planner for founders of companies around QSBS. The specific problem that QSBS rollover solve is for a shareholder of an early stage company. Most often founders or very early investors, say, maybe series A or earlier shareholders. It's an incentive to basically hold your stock for a quote unquote long time. In this sense, that means, you know, now under some new rules, basically three to five plus years. It's a tax exemption available to folks who hold their stock for at least five years. Then they can exclude from federal income tax now up to $15 million of gains when they sell that stock. So you have to be a shareholder in an early stage C corporation, early stage company. Frazer Rice (01:50.616).Those founders before three to five years are trying to figure out how to use this tool. What are the challenges in making sure they don't blow up the transaction by transferring something poorly. Or having their company grow too large or have too much cash or those types of things? Maybe list out a little bit some of the challenges that are out there that that a founder needs to be aware of. Brady Weller (QSBS Rollover) (02:22.509).Yeah. So we don't have to constantly caveat. I'll mainly talk as though we're speaking about the pre July 5th, 2025 rules for QSPS. Anything, any stock issued after that date, middle of last year. is under a slightly different set of rules. They are more expanded rules, but I'll speak to this sort of from those old rules. And so the old rules state that you have to hold your stock for at least five years. And if you do, you can exclude a large portion from federal income tax, usually $10 million for founders. But if you don't hold the stock for five years, your only option is to take the cash from that sale. For example, say you sell stock at year three or year four, and purchase new QSBS eligible stock with that cash within 60 days. So it's sort of like the 1031 exchange. Folks maybe are more familiar with real estate property exchanges. Its sort of like a 1031 exchange for stock. So you take the cash and you purchase a like kind quote unquote asset with it. Now the challenge with that is 60 days is not a very long time. And when you're a founder of a company who just went through liquidity. You just got your deal done and the whirlwind that that is. Now you're dealing maybe in a post liquidity world. You're maybe running another team at the acquirer or you're otherwise involved. 60 days is not a long time to be able to find and diligence a new opportunity. . It's just not feasible. Especially for founders to use that cash to say buy stock in someone else's company. It just doesn't make sense. Like risk adjusted, I suppose. Frazer Rice (04:05.579)No, it's a miracle that your company did great. Now you have to go and find another miracle and make it work within 60 days. It's crazy. Brady Weller (QSBS Rollover) (04:10.143).That that's the biggest that's probably the biggest barrier to executing them. For the longest time there just weren't a lot of people. They hadn't come alongside founders to help advise them on structured ways that they could do these rollovers. Yeah, the options are risky. It's like take your money and invest it in Dave's startup in San Francisco. He's going to lose your money. So that may be what you want to do with that money. To keep your risk profile sort of moving. But that's not tax planning in any way. Right. To make that decision just to save on federal income tax might not be the best way to use your rollover. So we've seen it much more for angel investors, something that they might use. People who want to maybe have a lot of deal flow. A lot of investment opportunities in front of them. But they want to keep that risk profile moving. I'd say timing and risk are the two biggest challenges when you're trying to execute a rollover. Frazer Rice (05:13.805).As a detail on that, you've got your company. You've got $10 million coming to you. Hopefully tax free, similar to a 1031. You don't have to go into one company, you could go into a basket of companies. Brady Weller (QSBS Rollover) (05:28.579).Yeah, you could take the cash, say you make $10 million from a sale. You could pay taxes on $3 million of it, assuming you haven't hit your five year requirement. Then, you could roll over the other seven in various other deals. You could put it all into one new company. What the rollover actually does is it continues your holding period clock from the last stock. So if you held for three years in your original company stock, You sell. You're able to reinvest those proceeds within 60 days. It continues your holding period. Once you're beyond a combined five the next liquidity event in the second company. Now you have proper seasoning on your shares, for lack of a better word, and then you can sell them under the QSPS exemption. Frazer Rice (06:17.143)So, this gets to what you do on a day-to-day basis. So a founder comes to you and says, all right, I've got this situation I think that's coming. And I need some advice. You're sort of letting them know what's happening here. How do you advise them, in a sense, whether it's through your company or even as a general matter? Do you have a suite of other founders and companies that are out there? And then… Maybe also similar to a 1031, is there sort of an intermediary function that needs to happen in order for the asset or the cash to go into sort of a, for lack of word, like an escrow account to then be deployed correctly into the eligible next company so that you keep that period going. Brady Weller (QSBS Rollover) (06:50.713)Boom. Brady Weller (QSBS Rollover) (07:05.839)That's a good question. It's not as formalized as the, you know, in terms of the 1031 world where there's sort of a designated intermediary and that's sort of required step in the process. This is very much the wire goes into your checking account for the sale of company A stock. Frazer Rice (07:11.703)Mm-hmm. Brady Weller (QSBS Rollover) (07:22.281)You send a wire back out to purchase stock in company B. When someone comes to us and is looking for guidance on how to do a rollover, sometimes they've talked to tax or trust in state attorneys already, or maybe they're CPA. And there are maybe 50 folks in the US who have, I'd say, Frazer Rice (07:37.463)Sure. Brady Weller (QSBS Rollover) (07:45.07)I call it advanced QSPS planning knowledge, which is they have the trust planning strategies, rollover knowledge, all of these things that sort of at their disposal that they can speak to, but it's a very small network. so our firm is actually the only non-CPA non-law firm in the country that deals directly with founders on these. And so we ended up kind of playing quarterback, connecting them with the right attorneys, maybe the right CPA, if they don't have one to make sure that the team is sort of assembled. You know, because the risk profile of taking your money and investing in someone else's company typically doesn't align with most founders' interests at that time, the service that we provide is helping them to roll that money into a new startup of their own. We think these founder-led rollovers where the founder or the shareholder who sold their original stock can now direct the proceeds into a new entity that they own and control. It's a really great way to execute this. It gives the shareholder, the founder the optimal amount of flexibility and