Advertise on podcast: Mechanics of Money

Years at a startup do not necessarily mean years holding qualifying stock. For founders and employees with equity, that distinction can matter long before a business is sold. Brian Lamb is the founder and CEO of Promissory and a co-founder of Trust & Will. His experience planning around his own equity led him to focus on QSBS and the trust structures founders consider before a liquidity event. In this conversation with Sam Silverman, Brian explains how company eligibility, stock acquisition, and the eventual deal interact. They discuss the difference between vested options and purchased shares, the changes to QSBS rules for newer stock, LLC conversions, and why the number in an acquisition announcement may tell a founder very little about the personal outcome. They also examine the control tradeoff in Brian's approach to non-grantor trusts and the cash demands employees can face when leaving a company. In this conversation: Why Brian's own equity planning led to PromissoryHow everyday estate planning differs from pre-exit trust planningWhat QSBS means and why company eligibility is only part of the questionWhy option vesting and stock acquisition are different eventsHow acquisition dates affect holding-period and exclusion rulesWhy federal and state tax treatment can differHow company growth can affect newly issued stockWhat founders weigh when converting an LLC to a C corporationWhy acquisition consideration and deal structure matter personallyWhy Brian encourages individual counsel for foundersWhen Brian prefers to begin trust planningHow gifting shares changes ownership and controlWhy vested options can still require cash at departureWhat employees can ask about early exerciseTopics covered: QSBS, qualified small business stock, Section 1202, stock options, holding periods, founder exits, non-grantor trusts, trust stacking, LLC conversions, 83(b) elections, equity compensation Guest: Brian Lamb - Founder and CEO, Promissory; Co-founder, Trust & Will https://www.promissory.com/ https://www.linkedin.com/in/brianlambco Newsletter: https://www.mechanicsofmoney.co Website: https://silvermancapital.com Subscribe to the Mechanics of Money for weekly conversations on private markets, alternative investments, and the mechanics behind building real wealth. Eligibility and tax consequences depend on individual facts, acquisition dates, and the transaction. Federal and state treatment can differ. #qsbs #founderexits #stockoptions #estateplanning #equitycompensation #mechanicsofmoney

A startup investment can look successful long before it produces spendable cash. Adam Spector has backed more than 200 early-stage companies, and he is reducing how much of his own portfolio he wants in that world. Adam is a four-time founder and the Founder & CEO of Chore, which supports startups with back-office operations. He also hosts Entrepreneurial Excellence. His perspective combines building companies, investing alongside founders, and waiting to learn what those investments are actually worth. Sam and Adam examine a secondary sale that Adam says repaid an entire fund, the long silence that followed, and the limits of treating a strong founder network as an investing advantage. They discuss his move toward later-stage opportunities and public equities, while separating his personal choices from a universal allocation formula. The second half turns to a different balance sheet: the time, stress, and family tradeoffs that can disappear inside the pursuit of a bigger net worth. In this conversation: Why Adam regrets shutting down his first companyHow an acquisition can benefit founders and investors differentlyHow his first syndicate pooled smaller checksWhy distributions matter alongside paper valuationsHow a secondary sale repaid one fund in Adam's accountWhy investor communication changes the ownership experienceWhy he is reducing his personal early-stage allocationHow he approaches later-stage SPVs and trusted introductionsWhy business expertise does not automatically transfer to investingHow frugality can become difficult to turn offWhere spending buys useful time and reduces household frictionHow Sam and Adam weigh ambition against personal financial stressTopics covered: angel investing, startup secondaries, liquidity, venture capital, SPVs, public equities, founder finances, opportunity cost, time, sustainable entrepreneurship Guest: Adam Spector, Founder & CEO of Chore Chore: https://www.hirechore.com/ Adam on LinkedIn: https://www.linkedin.com/in/adamspector2/ Newsletter: https://www.mechanicsofmoney.co Website: https://silvermancapital.com Subscribe to Mechanics of Money for weekly conversations on private markets, alternative investments, and the decisions behind building and using wealth. #angelinvesting #venturecapital #startupinvesting #founderfinances #capitalallocation #entrepreneurship #mechanicsofmoney

A founder can sell a business and still have important limits on how the proceeds are accessed and invested. What changes when the exit produces a promissory note instead of unrestricted cash? Brett Swarts is the Founder & CEO of Capital Gains Tax Solutions and the author of Building a Capital Gains Tax Exit Plan. His background in commercial real estate informs his work with entrepreneurs and their advisors on exit planning. In this conversation with Sam Silverman, Brett explains his Deferred Sales Trust model through a hypothetical $10 million business sale. Sam follows the money: who holds it, who approves investments, what happens if returns fall short, and how payments reach the seller. They also discuss a separate estate-planning structure, the distinction between basis and estate tax, and the investing blind spots that can follow a successful exit. In this conversation: Why an exit may require additional expertise alongside an existing CPAHow the founder’s next business or lifestyle affects the exit planHow Brett describes the seller-to-trust-to-buyer sequenceWhy the seller becomes a lender under the note structureHow investment approvals divide controlWhat happens in Brett’s example when assets underperform the note rateHow principal and interest affect the payment discussionWhy lifetime cash needs and inheritance goals can pull in different directionsWhy a basis adjustment and estate tax address different issuesHow Brett frames creditor protection and diversificationWhy entrepreneurial success does not establish investing skillHow one pair of founders kept capital available for future opportunities Topics covered: Deferred Sales Trust, business exit planning, installment sales, promissory notes, trust control, founder liquidity, estate planning, capital allocation Guest: Brett Swarts, Founder & CEO, Capital Gains Tax Solutions https://capitalgainstaxsolutions.com/ LinkedIn: https://www.linkedin.com/in/brett-swarts Book and background: https://capitalgainstaxsolutions.com/our-ceo/ Newsletter: https://www.mechanicsofmoney.co Website: https://silvermancapital.com Subscribe to Mechanics of Money for weekly conversations on private markets, alternative investments, and the decisions behind building and managing capital. #brettswarts #deferredsalestrust #businessexit #exitplanning #capitalgainstax #estateplanning #mechanicsofmoney

A franchise location and a franchise brand can participate in the same customer sale while carrying very different costs, responsibilities, and incentives. That distinction is where this conversation starts to get useful. Andy Louis-Charles is Managing Partner at Ranchos Ventures, which focuses on the franchise asset class. A former Chief Strategy Officer at Custom Ink and investment analyst at The Motley Fool, Andy has also owned multiple tax-franchise units. He brings both the capital-allocation perspective and the experience of executing inside an operating business. Sam Silverman and Andy work through the mechanics of company-owned expansion, franchisor revenue, and multi-unit franchise ownership. They explore why owners can resist growth once a business supports their lifestyle, why scale can change the buyer pool at exit, and why Andy is interested in services sold to restaurants rather than restaurant ownership itself. The conversation also examines his ownership thesis for white-collar professionals facing AI disruption, with a practical close on challenging assumptions before buying a business. In this conversation: How operating experience can inform capital allocationWhy investing after an exit can feel unfamiliarHow Andy combines broad venture exposure with active private ownershipWhat separates a franchisor investment from franchisee ownershipWhy taking cash out can compete with funding expansionHow royalties and service fees change a brand’s economicsWhat a hypothetical 100-unit expansion requires in capital and peopleHow operating scale can change a franchise portfolio’s buyer poolWhy property ownership and business ownership need separate analysisHow owner incentives and franchisee profitability interactWhy Andy sees an ownership opportunity in white-collar disruptionWhat attracts him to recurring B2B services and care businessesHow franchise comparisons and operator calls can test acquisition assumptions Topics covered: franchise investing, franchisor versus franchisee, multi-unit ownership, capital allocation, business expansion, unit economics, recurring B2B services, business acquisition, franchise due diligence Guest: Andy Louis-Charles, Managing Partner at Ranchos Ventures LinkedIn: https://www.linkedin.com/in/andylc Ranchos Ventures: https://ranchos.com/ Ranch Advisors: https://ranchadvisors.com/ Newsletter: https://www.mechanicsofmoney.co Website: https://silvermancapital.com Subscribe to the Mechanics of Money for weekly conversations on private markets, alternative investments, and the mechanics behind building real wealth. #franchising #franchiseinvesting #businessownership #capitalallocation #smallbusiness #privateinvesting #mechanicsofmoney

What is money still supposed to do after it has already bought financial security? A larger balance sheet can expand your options, but it cannot decide which options make a life meaningful. Brian Portnoy, PhD, CFA, is the founder and CEO of Shaping Wealth, a global expert on the psychology of money, and the author of *The Geometry of Wealth*. After more than two decades across mutual funds, hedge funds, portfolio management, research, and investor education, Brian came to a blunt conclusion: investing is not only a math problem. It is a psychology problem. Sam and Brian examine "funded contentment", the ability to underwrite a meaningful life, and the four sources Brian uses to make that idea practical: connection, control, competence, and context. They discuss the moving definition of enough, what retirement can feel like when work supplied identity, and why experiences and relationships tend to outlast the pleasure of expensive objects. In this conversation: Why Brian left complex investment analysis for behavioral financeThe difference between being rich and being wealthyHow funded contentment turns meaning into a financial questionThe four C's: connection, control, competence, and contextWhy many of life's most valuable experiences carry a modest price tagRetiring from a career versus retiring toward a next chapterHow a $100 million portfolio can coexist with an empty lifeWhy the payoff from a luxury purchase often moves beyond the objectThe missing complexity premium in alternative investmentsWhy doing nothing may be the hardest part of compoundingIlliquidity as both behavioral guardrail and portfolio riskWhat volatility laundering hides in private-market reportingWhy investing outside a plan is speculationThe advisor's role as planner and behavioral coachHow social comparison turns everyone into your financial neighborTopics covered: psychology of money, behavioral finance, funded contentment, rich versus wealthy, financial planning, retirement purpose, alternative investments, complexity premium, private-market illiquidity, volatility laundering, investor behavior, wealth management Guest: Brian Portnoy, PhD, CFA, founder and CEO of Shaping Wealth - https://www.shapingwealth.com/ Newsletter: https://www.mechanicsofmoney.co   Website: https://silvermancapital.com Subscribe to Mechanics of Money for weekly conversations on private markets, alternative investments, and the mechanics behind building real wealth. #behavioralfinance #psychologyofmoney #fundedcontentment #financialplanning #alternativeinvestments #privatemarkets #wealthmanagement #investorbehavior #mechanicsofmoney

High income is not the same thing as wealth. For a revenue leader, the bigger question is whether the next five years should be spent maximizing cash compensation, or whether the next 20 should be spent building and owning an asset. Sam Jacobs is the founder and CEO of Pavilion, co-host of the Topline podcast, and author of Kind Folks Finish First. He has spent his career building and leading go-to-market organizations, from early-stage companies to global sales and customer-success teams. In this conversation, Sam Jacobs and Sam Silverman unpack the economics behind revenue leadership: the short tenure of a CRO, the value created between $1 million and $10 million in revenue, the practical limitations of employee stock options, and the lifestyle pressure that often follows a breakout year in sales. They also compare short-term cash optimization with long-term career development, outline a diligence process for evaluating sales roles, and consider what AI changes - and does not change - about complex human buying decisions. In this conversation: Why senior revenue roles become less secure as their impact growsHow operators can create enterprise value without sharing proportionately in the upsideWhy fast-growing AI companies and slower-growth software businesses face radically different valuation marketsWhy there is no separate set of unit economics for AIHow stock-option exercise costs and taxes complicate employee equityWhy lifestyle inflation can turn exceptional income into a higher break-even pointHow a large annual commission can mimic some of the discipline of a liquidity eventWhy ownership becomes more attractive as the time horizon expandsHow to diligence a sales team before accepting an offerWhy a difficult product can sometimes teach more than an easy quotaHow compensation plans change after a seller breaks themWhy AI may increase productivity without removing the human saleHow Pavilion is being built as an enduring, cash-generating institutionTopics covered: revenue leadership, sales compensation, CRO tenure, employee equity, stock options, lifestyle inflation, business ownership, entrepreneurship, B2B SaaS, unit economics, go-to-market strategy, AI and sales, career planning, wealth creation Guest: Sam Jacobs, founder and CEO of Pavilion  https://www.joinpavilion.com/ https://www.linkedin.com/in/samfjacobs/ Newsletter: https://www.mechanicsofmoney.co  Website: https://silvermancapital.com Subscribe to Mechanics of Money for weekly conversations on private markets, alternative investments, and the mechanics behind building real wealth. #salesleadership #revenueleadership #businessownership #entrepreneurship #equity #b2bsaas #futureofwork #mechanicsofmoney

Putting capital to work can feel productive. But when a private deal locks that capital away for five years - and possibly ten - patience may be the more active decision. Jeremy Roll is President of Roll Investment Group and a full-time passive investor who began moving his savings from public markets into cash-flowing private investments in 2002. He has participated in more than 200 LLCs over that period and remains invested in more than 60 today. Jeremy joins Sam Silverman to explain why he has become more defensive despite decades of experience in real estate syndications and alternative investments. Their conversation moves from Jeremy's path out of Disney and Toyota into full-time LP investing to the practical questions investors should ask about liquidity, cycle timing, sponsor history, leverage, fees, and alignment. Jeremy also explains his personal thesis on AI spending and the next market reset, while repeatedly distinguishing his approach from financial advice. In this conversation: How cash-flowing investments allowed Jeremy to leave the corporate worldWhy he would not recommend his original 100% illiquid allocationHow technology and public solicitation changed private real estate investingWhy a business exit can create pressure to reinvest too quicklyHow Treasury liquidity changes the opportunity-cost calculationWhy private-market returns must compensate investors for illiquidityWhat Jeremy wants to see before redeploying capitalWhy a downturn can give LP capital more negotiating powerHow a sponsor's foreclosure can affect future borrowing costsWhat conservative underwriting and underpromising look like in practiceHow acquisition fees, AUM fees, and deal volume can weaken alignmentWhich real estate sectors Jeremy finds more predictableWhy new LPs should learn one asset class before diversifyingWhy Jeremy would rather enter a real estate recovery late than catch a falling knife earlyTopics covered: passive investing, real estate syndications, limited partners, alternative investments, market cycles, liquidity, Treasury bills, sponsor due diligence, underwriting, illiquidity premium, syndication fees, AI infrastructure, defensive investing Guest: Jeremy Roll, President of Roll Investment Group - https://www.linkedin.com/in/jeremy-roll-655107/ Newsletter: https://www.mechanicsofmoney.co Website: https://silvermancapital.com This conversation is for educational purposes only and does not constitute investment advice. Subscribe to Mechanics of Money for weekly conversations about private markets, alternative investments, and the mechanics behind building real wealth. #passiveinvesting #realestateinvesting #syndications #alternatives #privatemarkets #marketcycles #limitedpartners #mechanicsofmoney

What happens when your net worth reaches $500 million, but exists almost entirely on paper? For Martin Tobias, watching that concentrated position fall roughly 90% became a lasting lesson about liquidity, risk, and the difference between appearing wealthy and possessing durable wealth. Martin is the founder and managing partner of Incisive Ventures, a pre-seed venture capital firm focused on B2B software companies that reduce friction at scale. A three-time venture-backed CEO, Martin raised more than $500 million across his companies and completed two IPOs. His career also includes Accenture, Microsoft, and a venture partner role at Ignition Partners. He has since invested in eight companies that reached unicorn status. In this conversation, Martin joins Sam Silverman to trace his progression from corporate employee to founder, angel investor, and professional venture manager. He explains how early Microsoft equity created life-changing wealth, why delaying that opportunity carried an enormous cost, and how his experience with concentrated IPO stock shaped the way he protects capital today. Martin and Sam also examine the power-law economics of venture capital. They discuss why most early-stage investments may fail, why a 10x outcome may still be insufficient within a diversified fund, and how a small number of 100x outliers can determine the performance of an entire portfolio. In this conversation: How Microsoft equity created founder-level wealth for a corporate employeeWhy delaying Microsoft’s offer by one year carried a $20 million opportunity costWhy a $500 million paper net worth was not the same as accessible cashHow IPO lockups and concentrated stock complicate personal liquidityWhy Martin placed most of a major win into conservative, cash-flowing assetsHow AI is changing entry-level careers and traditional training groundsWhy Martin focuses on capital-efficient, pre-seed B2B softwareWhat he looks for in founding teams and their distribution advantagesWhy his angel portfolio underperformed his professionally managed venture portfolioHow deal flow, selection bias, and adequate runway affect investment outcomesWhy venture funds depend on extreme outliers rather than consistent moderate winsHow aspiring venture managers can build credibility before raising a blind poolTopics covered: Martin Tobias, Incisive Ventures, venture capital, pre-seed investing, B2B software, startup equity, founder liquidity, concentrated stock positions, angel investing, power-law returns, portfolio construction, wealth preservation, AI and careers Guest: Martin Tobias, founder and managing partner of Incisive Ventures https://incisive.vc/ Newsletter: https://www.mechanicsofmoney.co Website: https://silvermancapital.com Follow the Mechanics of Money for weekly conversations on private markets, alternative investments, and the mechanics behind building real wealth. #venturecapital #preseed #startupinvesting #b2bsoftware #angelinvesting #wealthstrategy #privateinvestments #mechanicsofmoney

How much of your financial life have you never said out loud to another person, and what is that silence actually costing you? Sam sits down with Dr. Megan McCoy, the first Certified Financial Therapist and Acting Chair of the Personal Financial Planning program at Kansas State University. Megan knew she wanted to be a therapist as a kid. She was midway through a doctorate in family therapy when the Great Recession hit, and her faculty started cross-training marriage and family therapists alongside financial planning students. Sitting next to a financial planner while treating clients changed her practice permanently, and she never stopped taking the finance coursework. She now runs the financial planning program at K-State, co-edits the Financial Planning Review, and researches the intersection most financial plans ignore entirely: money and well-being. In this conversation: What a financial therapist actually is, and how the discipline came out of the Great RecessionWhy the emotional case for a paid-off mortgage can beat the math on paperThe shame that followed 2008, and why self-forgiveness is a financial stepHow retirement takes your identity along with your title, and who it hits hardestWhy your ten-year dream stays vague, and the questions that force it into focusThe quarterly lottery ticket date she runs with her husbandThe $20 experiment proving giving beats spending, even when people are forced into itWhy 70% of people have not talked to a living soul about money in a yearFinancial infidelity, and why it damages a marriage close to the level of actual infidelityThe prenup reframe that takes money off the table instead of putting it onWhy charitable giving is one of the biggest fights couples have about moneyHow spenders and savers slowly push each other to opposite extremesThe money story parents pass to their kids without ever saying it out loudMaking a 12-year-old earn a $400 bat, and where enabling actually comes fromWhether college still makes sense, and the two-plus-two path she recommendsTopics covered: financial therapy, money psychology, behavioral finance, money and marriage, financial infidelity, joint accounts, prenuptial agreements, divorce planning, spending and happiness, charitable giving, financial socialization, raising kids with wealth, enabling adult children, retirement identity, college ROI, one income households, wealth psychology Guest: Megan McCoy, Ph.D., Acting Chair of Personal Financial Planning, Kansas State University | https://www.linkedin.com/in/megan-mccoy-phd Newsletter: https://www.mechanicsofmoney.co Website: https://silvermancapital.com Subscribe for weekly conversations on private markets, alternative investments, and the mechanics behind building real wealth. #financialtherapy #moneyandmarriage #wealthpsychology #behavioralfinance #financialinfidelity #moneymindset #raisingwealthykids #privatemarkets #personalfinance #mechanicsofmoney

You're sitting on a pile of credit card points and no real idea what they're worth. What if the same balance that gets you a $600 hotel room could get you an $1,800-a-night suite instead? And what if the reason you can never find award availability has nothing to do with your points at all? Sam sits down with Colin Stroud, founder of Go Somewhere, a credit card rewards consultancy for high-spending business owners and people sitting on large point balances. Colin got into points out of necessity: he'd taken a low-paying job, had a wife and a baby, and realized the only vacation his family could afford was a $400 Airbnb in the woods in rural Ohio. He went down the rabbit hole from a boring corporate desk, started booking trips for friends, and turned it into a full-time business in 2023. He's since helped 500+ families take trips they assumed were out of reach, from transatlantic business class for a family of nine to $30k+ luxury Caribbean stays during peak dates. In this conversation: How Colin went from no travel budget to consulting on points full timeWhy flexible bank points beat co-branded airline and hotel cards for most travelersThe $6,000 flight to Italy Sam booked for 70,000 points, and what that works out to per dollar spentHow to match a card strategy to where your business actually spends, even when your categories earn no bonusWhy airline status is close to worthless if you were already going to fly up frontWhich hotel statuses you can buy and which you can't: Marriott Ambassador vs. Hilton vs. HyattThe $30,000 Christmas week in St. Kitts a client got for points and nothing out of pocketMarriott's fifth-night-free rule and why points only redeem well at the top endThe $10-a-month tool that hunts premium cabin deals for you in plain EnglishRepositioning flights: paying $200 to reach a hub and unlocking thousands in award valueThe planning reframe that turns "there's never availability" into a $1,700-a-night room for 30,000 pointsTopics covered: credit card points, travel rewards, points and miles, business class, award travel, flexible points, transfer partners, airline status, hotel status, Marriott, Hyatt, Amex, Chase, Capital One, seats.aero, luxury travel, business owners, high spenders, travel hacking Guest: Colin Stroud, Founder, Go Somewhere | https://www.gosomewhere.world Newsletter: https://www.mechanicsofmoney.co Website: https://silvermancapital.com Subscribe for weekly conversations on private markets, alternative investments, and the mechanics behind building real wealth. #creditcardpoints #pointsandmiles #travelrewards #awardtravel #businessclass #luxurytravel #travelhacking #mechanicsofmoney #businessowners #smartmoney

What happens when you sell your company, deposit more money than you've ever had, and immediately feel worse than before? Sam sits down with Jerome Myers, Certified Exit Planning Advisor, founder of Exit to Excellence, and author of Your N.E.X.T.: Finding Fulfillment After Your Exit. Jerome built a $20 million division from zero in a single year inside a Fortune 550 company, walked away on principle, then later discovered what he calls the Founder's Exit Paradox: founders who win on paper and quietly fall apart afterward.  He now coaches founders through what comes after the transaction: the identity loss, the relationship collapse, and the spending paralysis that no advisor prepares them for. In this conversation: Jerome's origin story and the $2B founder who said he still hasn't beaten his crisisWhy 60% of the people you spend the most time with vanish after an exitThe Transaction Illusion and why money only solves two levels of Maslow's hierarchyThe mountain metaphor: ascent, summit, and the descent nobody talks aboutWhy $15M in cash can feel smaller than $3M a year in incomeWhat happens when operators become capital allocators overnightJerome's Five Scars of Success and the $44M client who wouldn't take a vacationWhy Die with Zero changed how his clients think about spendingThe scholarship text on Mother's Day and what fulfilled founders actually spend onThe purpose formula founders already know but forget to apply to themselves Topics covered: exit planning, founder psychology, post-exit depression, identity crisis, transaction illusion, hedonic treadmill, capital allocation, Maslow's hierarchy, private equity, founder fulfillment, giving policy, buy box, accredited investors, wealth management, entrepreneurship Guest: Jerome Myers, CEPA, MBA, Founder, Exit to Excellence | https://www.linkedin.com/in/jeromemyers Newsletter: https://www.mechanicsofmoney.co Website: https://silvermancapital.com Subscribe for weekly conversations on private markets, alternative investments, and the mechanics behind building real wealth. #exitplanning #founderpsychology #postexitlife #transactionillusion #mechanicsofmoney #wealthmanagement #privatemarkets #entrepreneurship #founderexit #capitalallocation

What's the difference between the entrepreneur who pays full capital gains tax on a $20M exit and the one who pays almost none? Usually, it's not income. It's whether anyone on their team was hired to plan ahead. Sam sits down with Noah Rosenfarb, a third-generation CPA who's spent his career inside the financial lives of the ultra wealthy. Noah started as an expert witness in high-net-worth divorce cases, built and sold a family office for affluent divorced women, syndicated close to $1B in real estate, and watched much of that portfolio get crushed when rates doubled.  Today he leads Wealthrive, a tax strategy firm for entrepreneurs with seven-figure incomes and eight-figure exits, built on a simple thesis: your tax preparer files history, but a strategist plans the future. In this conversation: From forensic accountant to expert witness in divorce court, and why acrimony paid the billsThe $100M family that skipped the prenup on purpose, and what the wife discovered in the divorceWhy the ultra wealthy own nothing but control everythingWhat exit tax planning is worth: typically 10-30% of the purchase priceThe proprietary structure that turns $2M invested into a $20M paper lossWhat tax "risk" actually means: audit odds by income bracket, case law, and opinion lettersPhantom gains, partnership allocations, and depreciation arbitrageNoah's real estate arc: a decade of 27% IRRs, then deals returning 40 cents, 20 cents, or zeroLosing tens of millions of investor capital, and rebuilding with gratitudeWhy his new capital only goes into his operating business and public marketsHis advice for founders years before an exit: hire a tax strategist, not just a preparer Topics covered: tax strategy, tax planning, capital gains tax, exit planning, selling a business, family office, trusts, asset protection, prenuptial agreements, IRS audits, real estate syndication, depreciation, cost segregation, phantom gains, partnership structures, high net worth, private markets, entrepreneurship, wealth building Guest: Noah Rosenfarb, CPA, Founder, Wealthrive | https://www.linkedin.com/in/noahrosenfarb Newsletter: https://www.mechanicsofmoney.co Website: https://silvermancapital.com Subscribe for weekly conversations on private markets, alternative investments, and the mechanics behind building real wealth. #taxstrategy #taxplanning #exitplanning #wealthbuilding #familyoffice #privatemarkets #mechanicsofmoney #entrepreneurship #capitalgains #realestateinvesting

How do you run a US real estate fund, SEC-regulated, entirely US-based investors, from a surf town in Costa Rica, and still turn down most of the deals you're offered? Sam sits down with Sarah Miskelly, founder and fund manager of Hylee Capital, a firm that helps accredited investors access carefully selected US real estate and alternative investments. Sarah grew up in her family's real estate business in Toronto, built a multi-six-figure brokerage, and then walked away from it at its peak, burned out and planning an exit from the start. She'd been quietly investing as an LP on the side, so she shut the brokerage down, moved her family to Costa Rica, and rebuilt as a fund manager she can run from her laptop. To date, Hylee Capital has deployed over $16M alongside roughly 100 investors. In this conversation: The full origin story, from managing family multifamily properties to running a fundWhy she walked away from a multi-six-figure brokerage business at its peakWhat relocating a family abroad actually costs, and why "it's cheaper" is a mythWhether managing capital remotely helps or hurts credibility with investorsDiversifying across verticals and the capital stack, not just asset classesMatching deals to an investor's actual buy box and stage of lifeWhy fund-manager compensation weighted toward exit keeps interests alignedWhat real due diligence looks like: underwriting, whisper networks, background checksThe large-name sponsor deal she passed on, and what the capital stack gave awayWhy she turns down almost everything sent to her inboundHer one piece of advice for relocating and for breaking into the space: bet on yourselfTopics covered: real estate, fund management, private real estate, due diligence, capital stack, preferred equity, common equity, LP investing, portfolio diversification, alternative investments, accredited investors, real estate syndication, passive income, relocating abroad, Costa Rica, expat life, lifestyle design, women in finance, private markets Guest: Sarah Miskelly, Founder & Fund Manager, Hylee Capital | https://hyleecapital.com Newsletter: https://www.mechanicsofmoney.co Website: https://silvermancapital.com Subscribe for weekly conversations on private markets, alternative investments, and the mechanics behind building real wealth. #realestateinvesting #fundmanagement #privatemarkets #alternativeinvestments #duediligence #accreditedinvestor #mechanicsofmoney #lifebydesign #passiveincome #wealthbuilding

How did a COVID-era face mask business become the launchpad for an 8-figure service company, and a life built entirely by design? Sam sits down with Arman Taheri, co-founder and CEO of TalentPop, a talent solutions company serving over 750 e-commerce brands with customer service management, executive assistants, and marketing support. Arman started in e-commerce, pivoted to face masks during COVID, scaled to eight figures in under a year, and used that momentum to build TalentPop into a multi-eight-figure platform, all while deliberately designing his life around the business rather than the other way around. In this conversation: The full origin story, from medical scrubs to face masks to discovering the CX staffing gapWhy mastering one core solution before diversifying was the catalyst for scaleThe "water faucets" framework for predictable, repeatable growthHow picking the wrong market size can quietly kill your ambitionsIncome tiers from $10K/month survival to generational wealth, and what changes at each levelMapping out what your dream lifestyle actually costs, then reverse engineering toward itWhy Arman chose a strategic partner over private equity, and what an 18-month search process looks likePersonal capital allocation: real estate, alternatives, managed wealth, and letting money compoundWhy investing in your primary residence might be the single best lifestyle investmentThe case against grind culture, and how to build ambitiously without burning outTopics covered: e-commerce, customer service, service business, scaling, COVID pivot, entrepreneurship, life by design, income tiers, generational wealth, strategic partnerships, private equity, personal finance, capital allocation, alternative investments, real estate, Dubai, lifestyle design, anti-grind culture Guest: Arman Taheri, Co-Founder & CEO, TalentPop | https://www.talentpop.co Newsletter: https://www.mechanicsofmoney.co Website: https://silvermancapital.com Subscribe for weekly conversations on private markets, alternative investments, and the mechanics behind building real wealth. #entrepreneurship #ecommerce #servicesbusiness #wealthbuilding #lifebydesign #privatemarkets #mechanicsofmoney #capitalallocation #alternativeinvestments #generationalwealth

What do 8,000 millionaires actually do with their money, and what can you learn from the patterns? Sam sits down with Tad Fallows, co-founder of Long Angle, a community of over 8,000 high- and ultra-high-net-worth members focused on managing wealth without anyone trying to sell them something. Tad bootstrapped a SaaS company to ~100 employees and a successful exit, then built Long Angle from a few dozen friends into one of the largest private wealth communities around, and he's been benchmarking how its members invest, spend, and think for years. In this conversation: Why most companies shouldn't raise venture capital — and the quiet power of bootstrappingThe net-worth tiers where life actually changes, and where it surprisingly doesn'tHow the wealthy really spend: buying back time vs. flexing, travel, and quiet wealthRent vs. buy, 2.5% mortgages, and why the housing market is frozenHow members allocate: roughly half public equities, a third in PE and alternatives, the rest in home equity, bonds, and cashWhat makes a great fund manager — investing alongside institutions, GP skin in the game, fees, and specializationThe ladder for emerging managers, from friends-and-family capital to institutional checksWhere Tad sees opportunity now: co-investments, secondaries, and upstream oil & gasWhy being a smart, educated client beats handing it all to a manager Topics covered: high net worth, wealth management, bootstrapping, SaaS exit, venture capital, private equity, asset allocation, alternative investments, secondaries, oil and gas, real estate, rent vs buy, estate planning, family offices, emerging fund managers, fundraising, roll-ups, financial independence Guest: Tad Fallows, Founder, Long Angle | https://www.longangle.com Newsletter: https://www.mechanicsofmoney.co Website: https://silvermancapital.com Subscribe for weekly conversations on private markets, alternative investments, and the mechanics behind building real wealth. #highnetworth #wealthmanagement #investing #privateequity #alternativeinvestments #privatemarkets #mechanicsofmoney #financialindependence