Advertise on podcast: DealQuest Podcast with Corey Kupfer

In her early twenties, with no capital at all, Arta Dawkins built her first business in Albania by sourcing packaging from abroad for factories that couldn't produce without it, using prepaid deals to fund the orders. Arta is an entrepreneur, luxury real estate realtor, and author based in Toronto. With RE/MAX Professionals Inc., she has earned Circle of Legends and Hall of Fame honors and previously ranked among the top one percent of Toronto real estate professionals. Her book is Add the Zeros (How to Create Value, Earn Trust, and Make Bigger Deals). WHAT YOU'LL LEARN: You'll learn how to create a deal by identifying a real need instead of starting with money, why prepaid structures can help you avoid giving up control to debt or equity partners, how one real estate listing can grow into a land development opportunity, and why confidence in negotiation comes from preparation and due diligence. ARTA'S JOURNEY: Arta grew up wanting to be an actress and writer, and her poems and articles were published in Albania, but her father steered her toward business accounting. Working in the business development office at the mayor's office, she saw factory owners stuck without packaging, quit after six months, and built an import and export business that grew to seventy-eight employees. In 1999, amid political tension in Albania, she immigrated to Canada with two small children and left that business behind. She started in Toronto real estate in 2007, sold a home that hadn't sold in three years within three weeks during her first week, and helped the owner subdivide his land into three lots, which led to larger development deals. KEY INSIGHTS: Money is not the only form of capital. Arta built her first business on prepaid deals, and she says the key is to identify a real need and create value from there. Prepayment depends on trust. Outside capital can cost you power and control over your company, but customers will only pay in advance when there is a real relationship behind the deal. Due diligence protects your biggest deals. Arta lost more than forty million dollars in pending sales when a private lender foreclosed during escrow on homes carrying a blanket mortgage she hadn't uncovered. Confidence comes from preparation. Arta says knowing what you're facing and who is on the other side gives you the confidence to ask for your value. Detachment is a strength. People can spot desperation, and she believes that if a deal isn't meant to be yours, you're worth more to another deal. Perfect for entrepreneurs without much capital, real estate professionals, and dealmakers who want to grow from single transactions into larger deals.WANT TO BE A GUEST ON DEALQUEST?Apply here: https://beaguestondealquest.com/guest FOR MORE ON THIS EPISODE: coreykupfer.com/blog/artadawkins FOR MORE ON ARTA DAWKINS:linkedin.com/in/arta-dawkins-ab5042101Website: artahomes.comBook: addthezeros.com FOR MORE ON COREY KUPFERhttps://www.linkedin.com/in/coreykupfer/ https://www.coreykupfer.com/ Corey Kupfer is an expert strategist, negotiator, and dealmaker. He has more than 35 years of professional deal-making and negotiating experience. Corey is a successful entrepreneur, attorney, consultant, author, and professional speaker. He is deeply passionate about deal-driven growth. He is also the creator and host of the DealQuest Podcast. Get deal-ready with the DealQuest Podcast with Corey Kupfer, where like-minded entrepreneurs and business leaders converge, share insights and challenges, and success stories. Equip yourself with the tools, resources, and support necessary to navigate the complex yet rewarding world of dealmaking. Dive into the world of deal-driven growth today! Episode Highlights with Timestamps 03:05 Arta's first deal, sourcing packaging for factories through prepaid orders 10:06 Leaving a seventy-eight person business in Albania and immigrating to Canada 15:12 Her first real estate deal and the one-stop-shop approach 19:29 How a blanket mortgage and a foreclosure derailed more than forty million dollars in sales 29:33 Why confidence comes from preparation and due diligence 37:19 Why deals happen in good markets and bad markets 39:59 What freedom means to Arta today Guest Bio Arta Dawkins is an entrepreneur, luxury real estate realtor, and author based in Toronto. She began her dealmaking career in Albania, where she built an import and export business without relying on personal capital by identifying demand, securing customer commitments, and structuring prepaid transactions. After immigrating to Canada, she rebuilt her career and became a recognized luxury real estate professional with RE/MAX Professionals Inc., earning Circle of Legends and Hall of Fame honors and previously ranking among the top one percent of Toronto real estate professionals. Her book, Add the Zeros (How to Create Value, Earn Trust, and Make Bigger Deals), teaches entrepreneurs and sales professionals how to recognize opportunity, create value, negotiate with confidence, and structure larger deals. Related Episodes Josh Emington on the due diligence layer that decides whether a deal is real. A natural follow-up to Arta's foreclosure lesson. Corey Kupfer and Sara Mostafa on what makes a true dealmaker. Expands on the entrepreneur versus dealmaker mindset discussed here. Jens Nielsen on building real estate freedom. Another view of real estate as a path to freedom. Keywords/Tags Arta Dawkins, Add the Zeros, Corey Kupfer, DealQuest Podcast, dealmaking, prepaid deals, bootstrapping, deals without capital, luxury real estate, Toronto real estate, land development, one-stop-shop real estate, negotiation, due diligence, detachment in negotiation, immigrant entrepreneur, cross-border business, personal branding, deal-driven growth

When the pandemic took Natasha Miller's multimillion dollar events business to zero in March 2020, she rebuilt it by doing deals with the competitors she used to bid against. One of those deals paid her company $12,000 for passing along a $650,000 project it didn't want to take on. Natasha Miller is CEO of Entire Productions, an experience design, event, and entertainment production company in San Francisco that has been on the Inc. 5000 list three years in a row. She is a classically trained violinist and jazz vocalist, a graduate of Goldman Sachs 10,000 Small Businesses, and an EO board member. WHAT YOU'LL LEARN: Corey and Natasha break down three ways to do business with competitors, including white label arrangements, strategic partnerships, and paid referrals, and when each one fits. They also cover why a joint pitch cost Natasha a bid, how partnering helps a certified women owned business compete for larger contracts, and how to staff up for strategy instead of reaction. NATASHA'S JOURNEY: Growing up in Des Moines, Iowa, Natasha only ever pictured herself as a performance artist. At 16 she went to a youth homeless shelter on Christmas Day and has lived on her own ever since, a story she tells in her book Relentless. She built her company the way she built her music career, by not turning down opportunities. Booked for multiple gigs in one night, she started bringing in other groups and managing them, which grew into an entertainment production company and then a full event production company serving clients like Salesforce, Google, Apple, LinkedIn, and Adobe. KEY INSIGHTS: Competitors can become partners. Natasha's Bay Area market is collaborative enough that companies who bid against each other also work together, which gives her extra capacity without extra overhead. White labeling keeps things simple for the client. A two company pitch felt too convoluted, so partners now work under Entire Productions' brand with an email address from her team. She stays accountable for their work, so she only white labels with partners she has known for years. Referrals turn the wrong project into revenue. Passing a $650,000 team outing to a partner earned a $12,000 check, and Natasha credits her company's reputation for getting the call at all. Partnering opens bigger doors. Some corporate buyers won't consider a company without the track record of a $15 million or $20 million business, but two partners together can credibly take on a $5 million annual project. Partners make for better hiring. With white label partners, freelancers, and contractors in place, Natasha can hire for strategic reasons instead of scrambling when big events land. Perfect for business owners rebuilding after a downturn, service firms that need flexible capacity, and diverse suppliers going after larger contracts.WANT TO BE A GUEST ON DEALQUEST?Apply here: https://beaguestondealquest.com/guest FOR MORE ON THIS EPISODE:https://www.coreykupfer.com/blog/natashamiller FOR MORE ON NATASHA MILLER:Entire Productions: entireproductions.comLinkedIn: linkedin.com/in/natashamillerInstagram: @natashamillersfBook: Relentless, available on Amazon and Audible FOR MORE ON COREY KUPFERhttps://www.linkedin.com/in/coreykupfer/ https://www.coreykupfer.com/ Corey Kupfer is an expert strategist, negotiator, and dealmaker. He has more than 35 years of professional deal-making and negotiating experience. Corey is a successful entrepreneur, attorney, consultant, author, and professional speaker. He is deeply passionate about deal-driven growth. He is also the creator and host of the DealQuest Podcast. Get deal-ready with the DealQuest Podcast with Corey Kupfer, where like-minded entrepreneurs and business leaders converge, share insights and challenges, and success stories. Equip yourself with the tools, resources, and support necessary to navigate the complex yet rewarding world of dealmaking. Dive into the world of deal-driven growth today! Episode Highlights with Timestamps [00:03:00]Natasha's first deal, getting paid to play the governor's inauguration [00:06:00]The business goes to zero in March 2020 and half the team is laid off [00:08:00]Passing a $650,000 team outing to a competitor for a $12,000 referral check [00:10:00]How white labeling works when a competitor joins your team [00:14:00]The joint pitch that confused the client and lost the bid [00:18:00]Why certified women owned businesses partner up to win larger contracts [00:32:00]The story behind Relentless, from a youth homeless shelter at 16 to entrepreneur Guest Bio Natasha Miller is the CEO of Entire Productions, an experience design, event, and entertainment production company in San Francisco that has been named to the Inc. 5000 list of fastest growing companies in America three years in a row. A classically trained violinist and jazz vocalist, she has released seven CDs. She is a graduate of Goldman Sachs 10,000 Small Businesses, has studied entrepreneurship at Harvard Business School and MIT, and is a member of the Recording Academy, ASCAP, SF Travel, and Meeting Professionals International. She is a member of EO in San Francisco, serves on its board, and is the author of Relentless. Related Episodes Episode 398 - Leah and Becca Wiser: Building a Business Partnership That Lasts Episode 420 - Corey Kupfer: The Truth About Business Partnerships Episode 351 - Corey Kupfer: There's a Deal for That, A Deep Dive into Strategic Deal Types Beyond M&A Keywords/Tags Natasha Miller, Entire Productions, partnering with competitors, white label partnerships, strategic partnerships, referral fees, event production, experience design, women owned business certification, supplier diversity, deal-driven growth, Corey Kupfer, DealQuest Podcast

Marion Wagner posted to her blog for a year and a half with about three readers, one of them her dad. Then she committed fully to her own voice and within months reached a quarter million page views a month. In this remastered episode, she shares how mindset and strategic partnerships help online entrepreneurs grow without a large following. In this episode of the DealQuest Podcast, host Corey Kupfer sits down with Marion Wagner, a business mindset coach and former school psychologist who has built multiple six-figure businesses in two separate online industries. Using her signature Business Clarity Blueprint, she has helped hundreds of coaches, course creators, and online service providers grow businesses that generate 10K plus per month in well under a year. She also hosts the Get Out of Your Head and Grow Your Online Business Podcast. WHAT YOU'LL LEARN: You'll discover the three things a good strategic partnership does and why a small, engaged following can be worth more than a large, disengaged one. Marion explains how to pitch experts in adjacent niches and why most summit and mastermind appearances involve no money changing hands. She and Corey break down the 30 to 50 percent commissions common on affiliate launches and how lifetime client value changes that math. You'll also hear why belief has to come before tactics. MARION'S JOURNEY: As a little girl, Marion wanted to join the family business and become an attorney. Her first big deal came when Adidas approached her blog with a package, and she admits she would have said yes to five hundred bucks for the whole thing. After a year and a half of posting to almost no one, Marion had what psychologists call a lightning bolt moment and stopped trying to sound like other bloggers. Once she leaned into her own quirky voice, the growth followed. She later went back to her psychologist roots after seeing how many entrepreneurs had the strategies but not the belief. KEY INSIGHTS: Value matters more than follower count. Marion says 500 aligned followers who spend money and attention on what you talk about are worth more than five or ten thousand who could care less. An email marketer, for example, should pitch social media experts, funnel experts, or business coaches. Many partnership doors sit open and unused. Summits, masterminds, and online events build credibility and open up new audiences, yet very few people make the pitch. In Marion's words, "There's doors everywhere, but very few people actually think to walk through them." Affiliate commissions look different through a lifetime value lens. Launch affiliates usually earn 30 to 50 percent, though a twenty thousand dollar coaching platform may sit closer to 10 percent. Corey points out that affiliates are usually paid on the first sale only, while the business keeps 100 percent of later products and services. Belief is the engine. Marion would rather work with someone who believes in themselves than someone with every tool and certification but no confidence. Those who skip the inner work tend to burn out or quit, and Corey ties this to owning your value, a big theme in his book on authentic negotiating. Start relationships with genuine appreciation. Marion suggests telling someone how great their content is, which she says means a lot even to someone with a million followers. Perfect for coaches, course creators, and business owners who want to grow through strategic alliances and affiliate partnerships without first building a massive audience.WANT TO BE A GUEST ON DEALQUEST?Apply here: https://beaguestondealquest.com/guest FOR MORE ON THIS EPISODE: coreykupfer.com/blog/businesspartnerships FOR MORE ON COREY KUPFER https://www.linkedin.com/in/coreykupfer/ https://www.coreykupfer.com/ Corey Kupfer is an expert strategist, negotiator, and dealmaker. He has more than 35 years of professional deal-making and negotiating experience. Corey is a successful entrepreneur, attorney, consultant, author, and professional speaker. He is deeply passionate about deal-driven growth. He is also the creator and host of the DealQuest Podcast. Get deal-ready with the DealQuest Podcast with Corey Kupfer, where like-minded entrepreneurs and business leaders converge, share insights and challenges, and success stories. Equip yourself with the tools, resources, and support necessary to navigate the complex yet rewarding world of dealmaking. Dive into the world of deal-driven growth today! Episode Highlights with Timestamps:[00:02:16] - Introduction. Marion Wagner's background as a mindset coach for online entrepreneurs [00:06:05] - The three things a good strategic partnership does [00:11:51] - Getting featured in summits and masterminds, and how those deals are structured [00:15:08] - Affiliate launches, 30 to 50 percent commissions, and lifetime client value [00:21:39] - Two camps of entrepreneurs and why belief is the engine [00:28:10] - Money flows to vibration, and the blog breakthrough to a quarter million page views [00:38:08] - What freedom means to Marion Guest Bio: Marion Wagner is a business mindset coach who helps online entrepreneurs create a six-figure plan without a large following on social media. A former school psychologist, she has built multiple six-figure businesses in two separate online industries, starting with a blog that grew to a quarter million page views a month. She combines psychological and strategic approaches through her signature Business Clarity Blueprint and has helped hundreds of coaches, course creators, and online service providers launch and grow businesses that generate 10K plus per month in well under a year. Being her own boss allowed her to take her son out of daycare at about eight months old and work from home, much of that time as a single mom. She runs Marion Wagner Coaching, hosts the Get Out of Your Head and Grow Your Online Business Podcast, and lives in Denver, Colorado, with her husband and son. Related Episodes: Episode 420 - The Truth About Business Partnerships with Corey Kupfer. Corey's own take on business partnerships, a natural companion to Marion's online partnership playbook. Episode 398 - Building a Business Partnership That Lasts with Leah and Becca Wiser. Another angle on partnerships, focused on making one hold up over time. Keywords/Tags: strategic partnerships, strategic alliances, joint ventures, affiliate marketing, affiliate commissions, online business growth, deal-driven growth, audience growth, summits and masterminds, lifetime customer value, referral business, business mindset, owning your value, law of attraction, online entrepreneurs, coaches and course creators, digital products, growing with a small audience, partnership pitch, Marion Wagner

Standing in an airport after a meeting with a for sale by owner founder, Emily Blue called her colleague Ryan Halls to vent. When he asked which investment bank she planned to join, she realized there wasn't one she would put her name behind at every step of the process for wealth management founders. That moment led to Hue Partners. Emily Blue, CFA, is the co-founder of Hue Partners, an M&A advisory firm that guides wealth management founders through the sale of their businesses. She previously served as Head of Corporate Development at a national multi-family office and led valuation and negotiation efforts at one of the largest aggregators in the industry. WHAT YOU'LL LEARN: In this episode, Corey Kupfer and Emily explore the human side of RIA M&A, from the emotional shift founders face after a sale to the build or sell decision. They discuss why the RIA M&A cycle is still in its early innings despite headlines about lower deal counts, and why next gen talent is now central to deal value in wealth management. EMILY'S JOURNEY: Emily went to college to become a nurse, until an anatomy course showed her that path wasn't for her. Her first taste of M&A came at an asset manager that diversified beyond midstream energy through an acquisition, where she helped integrate the portfolio teams and educate the sales force on new products. That integration work shaped how she approaches deals today. After years on the buy side working with investment banks across the country, she and Ryan launched Hue Partners, a sell-side firm that works every engagement together and focuses on doing a lot for a very select few. KEY INSIGHTS: Culture and vision alignment matter as much as structure. "The money can be there, the deal can be the best structure you've ever seen," Emily said, "but if you're not gonna have fun with the people or you guys aren't aligned philosophically or from a vision perspective, it will be a rough road." Founders need to be ready to stop being the king or queen. Even with a phenomenal acquirer, emotions will come up that sellers can't anticipate at the start. As Emily put it, "even advisors need advisors." The blank sheet of paper exercise reveals the gap. Emily asks founders to draw their ideal day, then look back at the past month of their calendar for a day that matched it. Most are shell-shocked by what they find. Build or sell is a real choice. Founders don't have to sell to reclaim their time, but something has to change, whether that means investing in hires and technology or finding the right partner. M&A in a service business is a talent strategy. Emily noted that outreach to next gen advisors is "through the roof," and urged founders not to wait to take care of their people until they've reached their breaking point. Perfect for RIA founders weighing whether to build or sell, acquirers building their M&A programs, and next gen advisors thinking about their future.WANT TO BE A GUEST ON DEALQUEST?Apply here: https://beaguestondealquest.com/guest FOR MORE ON THIS EPISODE:https://www.coreykupfer.com/blog/emilyblue FOR MORE ON EMILY BLUE:https://www.linkedin.com/in/emilyblue-cfa/https://huepartners.com/ FOR MORE ON COREY KUPFERhttps://www.linkedin.com/in/coreykupfer/https://www.coreykupfer.com/ Corey Kupfer is an expert strategist, negotiator, and dealmaker. He has more than 35 years of professional deal-making and negotiating experience. Corey is a successful entrepreneur, attorney, consultant, author, and professional speaker. He is deeply passionate about deal-driven growth. He is also the creator and host of the DealQuest Podcast. Get deal-ready with the DealQuest Podcast with Corey Kupfer, where like-minded entrepreneurs and business leaders converge, share insights and challenges, and success stories. Equip yourself with the tools, resources, and support necessary to navigate the complex yet rewarding world of dealmaking. Dive into the world of deal-driven growth today! Episode Highlights with Timestamps [00:03:23] Emily's first deal and how integration work became her entry into M&A [00:10:26] Are you truly ready not to be the king or the queen anymore? [00:14:55] The blank sheet of paper exercise and the ideal day [00:24:03] The airport phone call that led to Hue Partners [00:38:10] Why the RIA M&A cycle is still in its early innings [00:50:12] Next gen talent and why M&A is a talent acquisition strategy Guest Bio Emily Blue, CFA, is the co-founder of Hue Partners, an M&A advisory firm that specializes in guiding wealth management founders through the sale of their businesses. Prior to establishing Hue, she served as Head of Corporate Development at a national multi-family office and led valuation and negotiation efforts at one of the largest aggregators in the industry. Emily lives with her husband, Harrison, and their four children, and serves as a board member for Girl Scouts of NE KS and NW MO and Big Brothers Big Sisters of Kansas City. Keywords/Tags Emily Blue, Hue Partners, RIA M&A, wealth management M&A, sell-side M&A advisory, next gen talent, succession planning, build or sell, M&A integration, founder transition, DealQuest Podcast, Corey Kupfer

There is more capital in private markets than most dealmakers have ever seen, and much of it has nowhere obvious to exit. In this second quarterly deals roundtable, Corey Kupfer sits down with his partners Brian Meegan and Sara Mostafa to break down what actually happened across the deal world in Q2 2026. Brian and Sara are Corey's partners on the deal side of the practice, working alongside him across mergers and acquisitions, capital raises, and complex negotiated transactions in wealth management and well beyond. WHAT YOU'LL LEARN: How record dry powder, a slowing IPO market, and the rise of continuation funds are reshaping exits, why cash at closing keeps giving way to earnouts and rollover equity, what is driving longer holds and stretched diligence timelines, what minority investors actually control, and why one founder near 450 million dollars in revenue decided not to go public. THE ROUNDTABLE'S JOURNEY: The conversation opens on the macro picture Corey brought back from the Echelon Deals and Dealmakers Summit, then moves through hard data on the collapse in private equity backed IPOs and the record surge of lower middle market deals coming to market. From there it turns human, with Brian's deal in history on the founding of US Steel, Sara's debut segment on remarkable women in business, and Corey's closing reflection on choosing a path that fits your values rather than the default one. KEY INSIGHTS: Private equity backed IPOs fell from 424 between 2017 and 2021 to 70 between 2022 and the present, according to Dealogic, and that narrowing exit window is a major reason so much capital is stuck in private markets. As dollars move down market, the lower middle market benefits. Axial reported a record 3,523 deals coming to market in Q2 2026, up roughly 4.79 percent over the same quarter last year. Longer holds are now the norm. A New York Times report put private equity's unsold portfolio companies at 33,575 as of June 30, up from about 32,500 a year earlier and roughly 15,923 a decade ago. Taking a minority investment does not mean keeping full control. Board seats, veto rights, tag along rights, and priority rights all come into play, a point Sara raised in a Family Wealth Report quote. In Echelon's post closing survey, the top reason sellers felt their expectations fell short, at 40 percent, was not deal economics or equity performance. It was autonomy and workload. Perfect for founders, business owners, and investors weighing whether, when, and how to do their next deal.WANT TO BE A GUEST ON DEALQUEST?Apply here: https://beaguestondealquest.com/guest FOR MORE ON THIS EPISODE: https://www.coreykupfer.com/blog/brianmeegansaramostafa FOR MORE ON KUPFER.https://www.kupferlaw.com FOR MORE ON COREY KUPFERhttps://www.linkedin.com/in/coreykupfer/https://www.coreykupfer.com/Corey Kupfer is an expert strategist, negotiator, and dealmaker. He has more than 35 years of professional deal-making and negotiating experience. Corey is a successful entrepreneur, attorney, consultant, author, and professional speaker. He is deeply passionate about deal-driven growth. He is also the creator and host of the DealQuest Podcast. Get deal-ready with the DealQuest Podcast with Corey Kupfer, where like-minded entrepreneurs and business leaders converge, share insights and challenges, and success stories. Equip yourself with the tools, resources, and support necessary to navigate the complex yet rewarding world of dealmaking. Dive into the world of deal-driven growth today! Episode Highlights with Timestamps 00:02 Opening the quarterly roundtable, continuation funds, dry powder, and a slowing IPO market09:15 Sara Mostafa on risk shifting to sellers through earnouts and rollover equity11:12 Brian Meegan on the collapse in private equity backed IPOs, 424 down to 7019:26 The New York Times data, 33,575 unsold private equity portfolio companies28:34 Deal in history, how a single dinner led to the founding of US Steel44:18 Remarkable women in business, the story of Estée Lauder52:37 A founder who chose not to go public, and why it mattered Guest Bio Brian Meegan has represented US and multinational clients on corporate matters for more than 25 years, primarily on M&A, business formation, contract negotiation, and real estate. Before joining Kupfer, he founded Evergent Law, listed in Best Law Firms in America (Colorado) for Corporate Law and the exclusive Colorado M&A firm in the IR Global network, and he separately founded Watson Ltd., a back-office support company serving law firms nationwide. Brian earned his B.S. and J.D. from the University of Colorado, is listed in Best Lawyers in America (Colorado), and is a self-described history nerd who powers the new Deals in History segment on the show. Sara Mostafa is a corporate attorney with nearly two decades of experience representing private companies and individuals across M&A, private equity, financing, corporate governance, employment, real estate, and outside general counsel work, with clients spanning technology, wealth management, retail, entertainment, construction, restaurants, medical practices, and fitness and nutrition. She began her practice at Cooley LLP in San Diego and later served as a Partner at Lobb & Plewe LLP before joining Kupfer. Sara earned her J.D. from UCLA School of Law and her B.A. magna cum laude from the University of Pennsylvania, completed Harvard Law School's Executive Education program in M&A in 2023, and is licensed in California and Hawaii. She speaks English, Spanish, Arabic, and French Related Episodes Episode 293, Sunny Vanderbeck, on selling without selling out and building deals aligned with your values. Episode 325, Kelly Finnell, on employee stock ownership plans and internal succession as an alternative exit path. Keywords/Tags DealQuest, quarterly roundtable, private equity, dry powder, continuation funds, IPO market, lower middle market, mergers and acquisitions, earnouts, rollover equity, minority investment, board seats, tag along rights, seller satisfaction, US Steel, Andrew Carnegie, J.P. Morgan, Estée Lauder, women in business, exit planning, capital raising, negotiation, Corey Kupfer, Brian Meegan, Sara Mostafa

In her first 90 days running corporate development for a venture-backed acquirer, Hannah Sandmeyer closed sixty million dollars in EBITDA. The company had raised a billion dollars in a single Series D and its whole model was growth by acquisition. Then it collapsed when the promised IPO never came. That experience showed her how powerful M&A can be, and it set up the question behind everything she does now, which is what that power looks like when it serves something other than speed and price. Hannah is the founder and CEO of Up and Over Advisors, the first certified B Corporation in the world dedicated exclusively to values-aligned M&A sourcing, and the founder of Steward Market, a live three-sided marketplace for ethical business transitions. She also co-hosts the Ethical Exits podcast. WHAT YOU'LL LEARN: Why mission-driven founders belong on the buy side and not only the sell side, how shared values and trust can change a deal's structure and open the door to seller financing, how employee ownership and acquisition can work together, and how Steward Market uses values as searchable infrastructure so sellers can find a buyer by mission and hold period rather than valuation alone. HANNAH'S JOURNEY: Hannah grew up in Boise, Idaho, wanting to be a civil rights lawyer for the ACLU, studied political science, and came to see M&A as social and economic justice work because an ownership transition is a redistribution of power. She spent about 18 years in go-to-market and revenue roles before being asked in 2021 to run a corporate development team, where she learned that buying a company is just a different kind of sale. After that acquirer collapsed, she started her own firm expecting to do fractional sales work for B Corps. Instead, founders kept asking her to help them buy companies, and fractional corporate development was born. When she suggested that mission-driven founders could be acquirers too, they recoiled, which led her and her partner to launch Ethical Exits to explore what mission-driven M&A actually looks like. KEY INSIGHTS: Once you see the power of inorganic growth, you cannot unsee it as a lever. The real question is not whether acquisition is good or bad, but what you point it at. Values are a real deal variable. When a buyer and seller genuinely share goals and build trust, sellers become more open to seller financing and less fixated on all cash or the highest multiple. Employee ownership and acquisition can reinforce each other. Hannah points to a social work company that converted to an ESOP, acquired other firms, and began cutting checks north of a million dollars to retiring social workers. An ethical exit is not a partisan idea. Yvon Chouinard put Patagonia's purpose into a trust, and Eddie Smith turned down offers north of four hundred million dollars for Grady White because, as he put it, the company has a soul. The two men likely sit at opposite ends of the political spectrum. Real freedom is reciprocal. Wealth and ownership expand a person's power to make consequential decisions, and for Hannah that increases obligation rather than removing it. Perfect for founders weighing a sale, would-be buyers who assume the buy side is not for them, and advisors who want the deals they work on to protect more than price.WANT TO BE A GUEST ON DEALQUEST?Apply here: https://beaguestondealquest.com/guest FOR MORE ON THIS EPISODE: https://www.coreykupfer.com/blog/hannahsandmeyer FOR MORE ON HANNAH SANDMEYER: Website: https://stewardmarket.com LinkedIn: https://www.linkedin.com/in/hannahsandmeyer Podcast: Ethical Exits, https://ethicalexits.com FOR MORE ON COREY KUPFER: https://www.linkedin.com/in/coreykupfer/ https://www.coreykupfer.com/ Corey Kupfer is an expert strategist, negotiator, and dealmaker. He has more than 35 years of professional deal-making and negotiating experience. Corey is a successful entrepreneur, attorney, consultant, author, and professional speaker. He is deeply passionate about deal-driven growth. He is also the creator and host of the DealQuest Podcast. Get deal-ready with the DealQuest Podcast with Corey Kupfer, where like-minded entrepreneurs and business leaders converge, share insights and challenges, and success stories. Equip yourself with the tools, resources, and support necessary to navigate the complex yet rewarding world of dealmaking. Dive into the world of deal-driven growth today! Episode Highlights with Timestamps [00:02] - Introduction to Hannah Sandmeyer and the intersection of M&A and mission  [05:44] - Hannah's first capital raise in fifth grade with a chess team coupon drive [12:06] - Landing in corporate development in 2021 and a billion-dollar growth-by-acquisition model[16:30] - Starting her own firm and the birth of fractional corporate development [27:32] - Patagonia and Grady White as models of the ethical exit [38:03] - The Three Legged Stool employee ownership and acquisition story [46:07] - How Steward Market works as a three-sided marketplace [01:01:11] - What freedom means to Hannah Guest Bio Hannah Sandmeyer is the founder and CEO of Up and Over Advisors, the first certified B Corporation in the world dedicated exclusively to values-aligned M&A sourcing, and the founder of Steward Market, a live marketplace for ethical business transitions. She also co-hosts Ethical Exits, a podcast exploring how ownership transitions can protect mission, workers, culture, and community. A former Peace Corps volunteer turned M&A operator, Hannah works at the intersection of ownership, capital, and moral courage. Based in Portland, Oregon, she is an avid cyclist raising a preteen and a chicken named Greta who believes she is a dog. Related Episodes Episode 325 - Kelly Finnell: How Employee Stock Ownership Plans Actually Work. A deep look at ESOPs as an exit and succession tool, and how employees become owners. Episode 293 - Sunny Vanderbeck: Building and Selling a Company Without Treating Profit and Purpose as Enemies. Conscious capitalism and value creation over short-term profit. Episode 366 - Jodi Hume: Founder Exits and the Emotional Journey Behind Major Business Decisions. The psychological weight of selling and what founders need to prepare for beyond the transaction. Keywords/Tags ethical exits, values-aligned M&A, B Corp, employee ownership, ESOP, stewardship ownership, mission-driven acquisitions, seller financing, deal structure, Steward Market, Up and Over Advisors, three-sided marketplace, buy side, legacy preservation, mission continuity, conscious capitalism

When George Dubec and his wife sold the largest singles network in South Florida in the early nineties, the buyer was another matchmaking firm looking to expand into events. What they were actually paying for was the database. "They couldn't replicate me and my wife as the face of the business," George says. Nearly forty years later, that lesson still drives how he advises business owners. George Dubec is considered one of the top business and social networking experts in the United States. He began his career as an engineer, rising to executive staff at Packard Electric, a division of General Motors, before moving to Florida in 1985 to build companies of his own. He has hosted radio and TV programs including the Internet Business Hour, has judged the Web Awards since 2006, and now serves on the advisory board of America's Real Deal, a business investment television show. WHAT YOU'LL LEARN: How business owners can access capital outside the standard fundraising path, including tax credits, tax refunds, and legal settlements that already belong to them. Why a customer database may be the most saleable asset a company owns. How fractional deals, crowdfunding platforms, and crypto-based sweeteners are reshaping who can invest and who can raise. And why a two to five minute pitch video now opens more investor doors than a polished deck. GEORGE'S JOURNEY: George grew up in Boardman, Ohio, in a town he compares to Happy Days, where he saw the first television set in the neighborhood and the phones were still party lines. He was the first person in his family to graduate from college, attending Youngstown State University. He spent roughly eighteen years at General Motors as an engineer before buying his job out and relocating to South Florida in 1985. With his wife he built the largest singles network in South Florida, running it from 1985 until about 1992, before online dating existed. After selling, he moved into the early web with a company called Webstream, hosting sites, then building them, then adding search engine optimization. He launched the Internet Business Hour radio show in 1998 and ran it for about twelve years. He technically retired from the company in 2010 and shifted into alternative funding work with business owners. KEY INSIGHTS: Data is the asset owners undervalue. The buyer of George's first company wanted the list, not the events. He now maintains a database of forty thousand clean email addresses and tells owners to build one, because it can generate revenue long before an exit and may be what a buyer is actually purchasing at the exit. There is money most owners never look for. George describes himself as an alternative funder, helping business owners recover capital through tax reimbursements, tax credits, tax refunds, and legal settlements. As he puts it, going out with a pitch deck and asking for money is really tough, and most owners stop at the one channel they already know. Widened access comes with a vetting problem. Alternative investments were once closed to all but the wealthy. Opening them up has real benefits, but George is candid that many of these platforms have two or three years of history and no track record to evaluate. "It's kind of like the wild frontier. It's like digging for gold." The pitch video is the new front door. Investors are buried in decks and one-pagers they do not have time to read. George recommends a two to five minute video of you and your principals as the thing that earns the deck a read. What investors are assessing in those minutes is whether the person pitching has the attitude, moxie, and experience to make it work. Freedom requires a system. Asked what freedom means to him, George argued that eleven superstars who each do their own thing will never win a football game. "You gotta find a system that suits you, that you can be free in the system." Perfect for business owners who have been told that bootstrapping and venture capital are the only two real options for funding growth.WANT TO BE A GUEST ON DEALQUEST?Apply here: https://beaguestondealquest.com/guest FOR MORE ON THIS EPISODE: https://www.coreykupfer.com/blog/georgedubec FOR MORE ON GEORGE DUBEC:  https://theultimatenetworker.com  https://techunfilteredagi.com  https://www.americasrealdeal.com  FOR MORE ON COREY KUPFER https://www.linkedin.com/in/coreykupfer/ https://www.coreykupfer.com/ Corey Kupfer is an expert strategist, negotiator, and dealmaker. He has more than 35 years of professional deal-making and negotiating experience. Corey is a successful entrepreneur, attorney, consultant, author, and professional speaker. He is deeply passionate about deal-driven growth. He is also the creator and host of the DealQuest Podcast. Get deal-ready with the DealQuest Podcast with Corey Kupfer, where like-minded entrepreneurs and business leaders converge, share insights and challenges, and success stories. Equip yourself with the tools, resources, and support necessary to navigate the complex yet rewarding world of dealmaking. Dive into the world of deal-driven growth today! Episode Highlights with Timestamps[02:17] Growing up in a no-tech Ohio town and seeing the neighborhood's first television set[06:36] Eighteen years at General Motors, buying his job out, and starting the largest singles network in South Florida[09:07] Selling the business and why the buyer was really after the database[13:43] Crypto coins as an investor sweetener, fractional deals, and other funding paths outside the usual channels[25:00] The four ways companies get funded on America's Real Deal, from sharks to a private stock exchange[26:23] Why a two to five minute pitch video matters more than the deck[44:27] Freedom inside a system and the football team analogy Guest Bio George Dubec is a business and social networking expert based in South Florida. After roughly eighteen years as an engineer at Packard Electric, a division of General Motors, he moved to Florida in 1985 and co-founded the largest singles network in South Florida with his wife, operating it until the early nineties. He then entered the early web industry with Webstream, working in hosting, web development, and search engine optimization, and launched the Internet Business Hour radio show in 1998, which he hosted for about twelve years. He has judged the Web Awards since 2006. Today he works with business owners on alternative funding sources, serves on the advisory board of the business investment show America's Real Deal, and hosts a new podcast called Tech Unfiltered. He is writing a book titled How to Thrive and Survive in the New High-Tech AI World. Related Episodes Episode 350 with Tom Dillon covers when not to take venture capital money and walks through alternative funding sources including private credit, SBA loans, term loans, and sale-leasebacks. It pairs directly with George's argument that most owners default to one channel and stop. Episode 370 with Gerry Hays examines democratizing access to early-stage investing through very small stakes, which speaks to the same tension George raises between widening access and protecting less experienced investors. Episode 351 is a solocast where Corey explores deal structures beyond mergers, acquisitions, and capital raising, including joint ventures, strategic alliances, and licensing agreements. A useful companion for owners looking to grow without a traditional raise. Keywords/Tags alternative business funding, tax credits for business owners, tax refunds, legal settlements, pitch video for investors, America's Real Deal, crowdfunding, Start Engine, WeFunder, fractional investing, private stock exchange, accredited investors, customer database value, business exit, authority marketing, personal branding, podcasting for business, AI agents, networking, deal-driven growth, DealQuest Podcast, Corey Kupfer, George Dubec

Matt Stevens walked away from his first closing table controlling two duplexes, having put nothing down, holding a check for forty seven hundred dollars. That deal taught him that things he assumed were impossible were actually available to him, and it started a career built on reading structure before reading price. Known as The Franchise Guy, Matt has more than 30 years in the franchise industry and has sat in nearly every seat at the table. He has been a franchisee, a franchise coach, a franchisor, and now a franchise consultant. He was rookie franchisee of the year, turned around struggling divisions, and served as a board member and partner inside a two billion dollar franchise group. WHAT YOU'LL LEARN: How to evaluate a franchise opportunity beyond the investment number, why first rights of refusal have essentially disappeared from franchise agreements, how territory math changes the economics of multi-unit ownership, the behavioral due diligence most candidates never perform on themselves, and where the real growth is happening in franchising right now. MATT'S JOURNEY: Matt got into franchising by reading an advertisement on a hallway wall at Wake Forest University. He joined the business that became CertaPro Painters when there were only 67 operators across Canada, New England, and the Mid-Atlantic. The deal had a zero dollar investment to get in and a 25 percent royalty on the back end, a trade both sides made deliberately. He spent about ten years in that system, moving from operator to coach to the franchisor side. Before franchising, Matt spent nearly two decades in rental property, building to 14 units before selling his last property in 2017. Over one six year stretch in franchising, he found, recruited, signed, trained, and mentored 167 franchise owners across nine states in a single system. Today he helps candidates cut through franchise marketing using non-public research on franchisors, their development teams, and their existing owners. KEY INSIGHTS: Every piece of human behavior is driven by inputs and outcomes rather than rationale or common sense. Matt was frustrated by several franchisor decisions when he was an owner. Once he became a franchisor, those same decisions made complete sense. His advice to candidates is to assume every rule exists for a reason and to ask why. First rights of refusal on territory used to be common in franchising and are now essentially gone. Matt's read is that the only reason a franchisor offers one today is that they are desperate to sign that candidate. What replaced it is a growth schedule tied to what an operator can realistically execute. Territory secured early is what Matt calls growth insurance. One territory costs X, three cost roughly 1.6X, and five cost roughly 2.2X, and six territories can be serviced with the same phone number and van as one. In fast moving markets, what is available today will not be available later. The hardest due diligence is the kind candidates perform on themselves. Investment and territory are confirmable. What is not confirmable is whether a person will replicate the daily behavioral patterns the system requires. One of Matt's screening questions is how long a candidate can go at zero income before hitting the panic button. The least appreciated opportunity in franchising is the mundane service business. Matt's framing is that in a market with 400 competitors within 30 miles, you are not competing against 400 companies. You are competing against the two others the customer called. That is how he became the largest buyer at his Sherwin Williams store in Keene, New Hampshire by May of his first year in the painting business at age 20. Perfect for anyone weighing franchise ownership, operators planning multi-unit growth, and dealmakers who want to see how structure and price get traded against each other in a real agreement.WANT TO BE A GUEST ON DEALQUEST?Apply here: https://beaguestondealquest.com/guest FOR MORE ON THIS EPISODE: https://www.coreykupfer.com/blog/mattstevens FOR MORE ON MATT STEVENS: https://heisthefranchiseguy.com  https://podcast.heisthefranchiseguy.com/DQ FOR MORE ON COREY KUPFER https://www.linkedin.com/in/coreykupfer/ https://www.coreykupfer.com/ Corey Kupfer is an expert strategist, negotiator, and dealmaker. He has more than 35 years of professional deal-making and negotiating experience. Corey is a successful entrepreneur, attorney, consultant, author, and professional speaker. He is deeply passionate about deal-driven growth. He is also the creator and host of the DealQuest Podcast. Get deal-ready with the DealQuest Podcast with Corey Kupfer, where like-minded entrepreneurs and business leaders converge, share insights and challenges, and success stories. Equip yourself with the tools, resources, and support necessary to navigate the complex yet rewarding world of dealmaking. Dive into the world of deal-driven growth today! Episode Highlights with Timestamps [03:26] - The first deal, two duplexes controlled with nothing down and a check at closing [14:14] - Why first rights of refusal disappeared and what it means when one is offered [21:14] - The behavioral due diligence candidates skip and the four Ds [31:43] - What separates successful franchisees, including the ABS framework[47:44] - What freedom means to Matt Guest Bio Matt Stevens, known as The Franchise Guy, is a franchise consultant with more than 30 years in the industry. He has been a franchisee, a franchise coach, a franchisor, and a franchise consultant, and was named rookie franchisee of the year early in his career. He has turned around struggling divisions and served as a board member and partner inside a two billion dollar franchise group. Matt is a franchise gold and century club member, a Business First Columbus 40 under 40 honoree, and the author of a three hour course on thorough franchise review. He holds three business degrees from Florida Southern College and Wake Forest University and is a MENSA member. His process walks candidates from first conversation to confident decision using real world validation, insider questions, and practical coaching. Related Episodes Episode 329 - Cliff Nonnenmacher on master franchising and who is not a fit for the franchise model. A useful companion for understanding the layers of ownership between single unit franchisee and franchisor. Episode 333 - Greg Mohr on franchise agreements, protected territories, and how franchisors identify their ideal franchisee. Pairs directly with Matt's discussion of what franchisors assess in candidates. Episode 330 - Pete Mohr on owning and exiting multiple franchise businesses, including buying himself out of an agreement that was not working. Offers the operator's view of what happens when the fit turns out to be wrong. Episode 336 - Devan Gonzalez on building an emerging fitness franchise from the franchisor side, which connects to Matt's read on growth in health and wellness. Keywords/Tags franchise consulting, buying a franchise, franchise due diligence, franchisee validation, franchise territory rights, first right of refusal, right of first offer, franchise royalty structure, multi-unit franchising, home services franchise, health and wellness franchise, deal structure, business ownership, entrepreneurship, DealQuest Podcast, Corey Kupfer, Matt Stevens, The Franchise Guy

A business partnership is often the first deal an entrepreneur ever does, long before any M&A or capital raise. In this solocast, Corey Kupfer steps back from the usual deal categories to talk about what it actually takes to be in a partnership, drawing on his own partnerships across multiple businesses and decades of helping clients form, evolve, and separate theirs. Corey Kupfer is an attorney, dealmaker, and negotiator with more than 35 years of experience. Beyond drafting the documents for new partnerships, he has guided partners through evolution, buyouts, and separations, and he serves as a mediator for partners working to part ways well. WHAT YOU'LL LEARN: This episode covers the due diligence founders most often skip, how partnerships fall out of alignment over time, what a partnership agreement can and cannot protect, why no employee ever matches an owner's commitment, and how to separate through a negotiated exit rather than a costly fight. COREY'S PARTNERSHIP JOURNEY: Corey has been in several partnerships over the years, starting with a law firm partnership formed in the 1990s that ended over economic differences and a different view of perceived value, then reconnected warmly with those partners decades later. He also built a real estate investment partnership with his partner Dan that stayed strong through the great recession because of aligned values and superb communication. His last partnership ran from 2010 to 2015 and ended in a difficult split over vision, values, and culture. Even so, that chapter deepened his work in the RIA space and introduced him to clients and colleagues he values to this day, a reminder that even partnerships that end can create lasting good. KEY INSIGHTS: The personal and cultural due diligence matters most and gets skipped most. Even when you already know someone well, you still need an honest conversation about this specific venture, your shared vision and values, and your goals and timelines. Partnerships evolve because the business, the people, and the market all change. Following where clients and the market lead is usually smart, but that evolution can pull one partner into alignment with a new direction while leaving the other behind, even when they started out aligned. The agreement is a roadmap, not a guarantee. An operating agreement or shareholders agreement can set the methodology for a split or buyout, but whether partners actually stay together comes down to trust, respect, communication, and a willingness to evolve. Litigation is rarely the best way to separate. The damage to the business, clients, and employee retention often means everybody loses, and the opportunity cost of the distraction is something people almost never calculate. A partnership is one deal type among many. Go in eyes wide open, get as clear an agreement as possible upfront when you cannot yet know who it will affect, and keep checking whether the partnership stays in alignment and integrity for you. Perfect for entrepreneurs weighing a partnership, founders navigating a separation, and anyone who wants to structure the deal before there is anything to fight about.WANT TO BE A GUEST ON DEALQUEST?Apply here: https://beaguestondealquest.com/guest FOR MORE ON THIS EPISODE: https://www.coreykupfer.com/blog/businesspartnerships FOR MORE ON COREY KUPFER:https://www.linkedin.com/in/coreykupfer/ https://www.coreykupfer.com/  Corey Kupfer is an expert strategist, negotiator, and dealmaker. He has more than 35 years of professional deal-making and negotiating experience. Corey is a successful entrepreneur, attorney, consultant, author, and professional speaker. He is deeply passionate about deal-driven growth. He is also the creator and host of the DealQuest Podcast. Get deal-ready with the DealQuest Podcast with Corey Kupfer, where like-minded entrepreneurs and business leaders converge, share insights and challenges, and success stories. Equip yourself with the tools, resources, and support necessary to navigate the complex yet rewarding world of dealmaking. Dive into the world of deal-driven growth today! Episode Highlights with Timestamps [00:00] - Why business partnerships are often the first deal an entrepreneur ever does [03:28] - The due diligence you owe yourself, even with friends and family [07:33] - How partnerships and the people in them grow apart over time [09:20] - A PR firm buyout and an operator versus developer split, when growing apart is nobody's fault[13:44] - Corey's own partnerships, from a 1990s law firm to real estate with Dan to the 2010 to 2015 split[19:46] - Why no employee ever matches an owner's commitment, and why it can still feel good to be the only decision maker[23:32] - Building a clear agreement on decisions, economics, and the what ifs[25:57] - Separating well, opportunity cost, and the CPR process from Authentic Negotiating Host BioCorey Kupfer is an expert strategist, negotiator, and dealmaker with more than 35 years of professional deal-making and negotiating experience. He is an entrepreneur, attorney, consultant, author of Authentic Negotiating, and professional speaker whose firm helps clients structure business partnerships, joint ventures, mergers and acquisitions, and capital raises. He is the creator and host of the DealQuest Podcast. Related EpisodesEpisode 351 - Solocast 77: A solocast breaking down joint ventures, strategic alliances, and the exit provisions that work like a partnership prenup. Episode 336 - Devan Gonzalez: A real world business partnership where the partners set up a clear conversation to keep friendship and business separate. Episode 366 - Jodi Hume: The emotional dimensions of exits and the decisions founders face when it is time to move on. Keywords/Tagsbusiness partnerships, partnership due diligence, vision and values alignment, operating agreement, shareholders agreement, buyout, negotiated exit, partnership separation, opportunity cost, mediation, authentic negotiating, CPR framework, entrepreneurship, deal-driven growth, DealQuest Podcast, Corey Kupfer

What if the smartest deal of your career was the buyout you refused to close? That is the call Brad Kugler made when a Silicon Valley firm tried to acquire his marketing platform. The original offer valued his company at roughly 19 times profit, but when the buyer cut it 20 percent late in the process, Brad ended the deal, and thirty months later he has no regrets. Brad is the CEO of Direct Mail 2.0, Who's Mailing What, and DM20.ai, and a serial entrepreneur with more than 35 years of building businesses through constant change. Brad grew a VHS distribution company from a million dollars to 25 million before streaming rode it back to zero, an experience he says taught him more on the way down than on the way up. He carried that hard-won judgment into every deal that followed, including a full acquisition process with Symphony Technology Group that he ended when the buyer used a churn recalculation to cut the offer 20 percent. For Brad, the freedom to run his own company outweighed the cash, the culture mismatch, and three years under a private equity group. But Brad is far from deal-shy. He acquired Who's Mailing What, a direct mail intelligence platform running since 1984, for 20 percent below asking price, grew its revenue by 50 percent, and used its four-decade database as the foundation for DM20.ai. That tool runs three frontier AI models against each other to predict how a direct mail campaign will perform, all for about 50 dollars. With his core market shrinking, a printer list that fell from more than 11,000 names to 3,600 in nine years, Brad now grows by acquisition and joint venture rather than fighting for share in a capped market. For any entrepreneur weighing an exit, an acquisition, or a raise, this conversation offers a grounded look at how self-awareness shapes better deal decisions at every stage of a career.WANT TO BE A GUEST ON DEALQUEST?Apply here: https://beaguestondealquest.com/guest FOR MORE ON BRAD KUGLER: Website: https://www.dm20.com LinkedIn: https://www.linkedin.com/in/bradkugler/ FOR MORE ON COREY KUPFER: https://www.linkedin.com/in/coreykupfer/ https://www.coreykupfer.com/ Corey Kupfer is an expert strategist, negotiator, and dealmaker. He has more than 35 years of professional deal-making and negotiating experience. Corey is a successful entrepreneur, attorney, consultant, author, and professional speaker. He is deeply passionate about deal-driven growth. He is also the creator and host of the DealQuest Podcast. Get deal-ready with the DealQuest Podcast with Corey Kupfer, where like-minded entrepreneurs and business leaders converge, share insights and challenges, and success stories. Equip yourself with the tools, resources, and support necessary to navigate the complex yet rewarding world of dealmaking. Dive into the world of deal-driven growth today! Episode Highlights with Timestamps [00:03] - Introduction[03:54] - A VHS business from a million to 25 million to zero [11:24] - The 19x offer and the culture red flags [13:14] - Why he walked away [17:10] - A friend's exit and what money cannot buy [27:08] - Acquiring Who's Mailing What  [38:16] - Growing by acquisition in a shrinking market [47:44] - What freedom means to Brad Guest Bio Brad Kugler is the CEO of Direct Mail 2.0, Who's Mailing What, and DM20.ai, three brands under one company dedicated to helping marketers and commercial printers get better results from direct mail. A lifelong entrepreneur and innovator with more than 35 years in business, Brad combines data, technology, and market intelligence to help businesses make smarter marketing decisions and uncover new growth opportunities. He grew a VHS distribution company from a million dollars to 25 million earlier in his career, and today he is focused on inorganic growth through acquisitions and joint ventures while building AI-driven tools for the direct mail industry.Keywords/Tags direct mail marketing, marketing technology, walking away from a deal, buy versus build, strategic acquisition, proprietary data, AI in marketing, DM20.ai, Who's Mailing What, growth by acquisition, joint ventures, shrinking market strategy, later-stage entrepreneur, exit strategy, self-awareness in business, deal-driven growth, Brad Kugler, DealQuest, Corey Kupfer

Zachary Beach bought his first house for little more than closing costs. The seller was mid-divorce and could not make the next payment, so Zach took title subject to the existing loan and later sold it on rent to own. That messy first deal came together as about a seventy thousand dollar deal and broke him into the industry. Zach went from bartending to his father in law's real estate business at twenty five and has since completed or advised on over a thousand deals. He is the CEO of Smart Real Estate Coach and a three time best selling co-author of Real Estate on Your Own Terms, The New Rules for Real Estate Investing, and Sell with Authority for Real Estate Investors. WHAT YOU'LL LEARN: How to structure creative real estate deals with no cash, no credit, and no banks, why implementation beats knowledge, how the three paydays system turns one property into three income streams, and how those same skills scale into acquiring companies. ZACHARY'S JOURNEY: Zach did not grow up around entrepreneurship or financial literacy. His first transaction was selling golf balls three for a dollar as a kid, and his real estate company is named Watch Street after the block where he picked them. After burning out on bartending, he joined his father in law's old-school, paper-heavy business and built the systems that became Smart Real Estate Coach, now a real estate investment company disguised as a coaching company with deals in more than eighty markets. KEY INSIGHTS: Creative financing is a people business first. Zach carries multiple tools, including seller financing, subject-to, and lease purchases, and matches each to the seller's problem instead of throwing away most of his leads. The three paydays system is the core model. A property sold on rent to own generates a deposit up front of three to ten percent, monthly cash flow, and a future cash-out from a built-in buyer. Rent to own only works when it is set up right. Zach would criticize ninety nine percent of rent-to-owns himself, which is why his team runs a quasi-underwriting process and credits the down payment toward the purchase price. Perfect for W-2 employees seeking a way out, burned-out investors watching the traditional model stop penciling, and operators exploring acquisition-driven growth.WANT TO BE A GUEST ON DEALQUEST?Apply here: https://beaguestondealquest.com/guest FOR MORE ON THIS EPISODE: https://www.coreykupfer.com/blog/zacharybeach FOR MORE ON ZACHARY BEACH: LinkedIn: https://www.linkedin.com/in/zacharyrbeach Facebook: https://www.facebook.com/ZRBeach/ Company: https://smartrealestatecoach.com Free books offer: https://3paydaysbooks.com/dealquest FOR MORE ON COREY KUPFER: https://www.linkedin.com/in/coreykupfer/ https://www.coreykupfer.com/ Corey Kupfer is an expert strategist, negotiator, and dealmaker. He has more than 35 years of professional deal-making and negotiating experience. Corey is a successful entrepreneur, attorney, consultant, author, and professional speaker. He is deeply passionate about deal-driven growth. He is also the creator and host of the DealQuest Podcast. Get deal-ready with the DealQuest Podcast with Corey Kupfer, where like-minded entrepreneurs and business leaders converge, share insights and challenges, and success stories. Equip yourself with the tools, resources, and support necessary to navigate the complex yet rewarding world of dealmaking. Dive into the world of deal-driven growth today! Episode Highlights with Timestamps: [00:03] - Introduction and Zach's path from bartender to real estate dealmaker [08:38] - The first real estate deal, a subject-to purchase on a roughly $180,000 property [22:55] - The biggest mistake investors make and why implementation beats knowledge [32:56] - The three paydays system and how creative financing creates three income streams [36:15] - Addressing the rent-to-own criticism and the quasi-underwriting process [43:12] - The integrity real estate roll-up and acquiring elite educators Guest Bio: Zachary Beach is the CEO of Smart Real Estate Coach and a partner in multiple seven figure businesses. He went from bartending and personal training into his family's real estate business at twenty five, and has since completed or advised on over a thousand deals using creative financing strategies including seller financing, subject-to, and lease purchases. He is a three time best selling co-author of Real Estate on Your Own Terms, The New Rules for Real Estate Investing, and Sell with Authority for Real Estate Investors, and he co-hosts the Smart Real Estate Coach and Not Just the Transaction podcasts. He mentors students across the country and is building an integrity-focused real estate coaching roll-up. Related Episodes: Episode 191 - Jack Bosch: Building a real estate education business on real deal experience. Bosch's path from investor to educator parallels how Smart Real Estate Coach teaches from actual transactions. Episode 183 - Kent Ritter: How to invest in real estate. Ritter's emphasis on consistent execution over big promises reinforces Zach's point that implementation is what separates successful investors. Episode 332 - John Martinka: Buying businesses and the dynamics of roll-ups. A useful companion for Zach's acquisition strategy and the difference between aggregating for size and adding real value. Episode 293 - Sunny Vanderbeck: Serial acquisition, roll-ups, and building a repeatable deal program. Relevant context for anyone thinking through an acquisition-driven growth model. Keywords/Tags: creative real estate financing, subject-to deals, rent to own, no money down real estate, three paydays system, seller financing, lease purchase, real estate coaching, Smart Real Estate Coach, Zachary Beach, W-2 to entrepreneur, real estate roll-up, real estate acquisitions, deal-driven growth, DealQuest Podcast

What if the job you almost didn't get became the foundation for building two public companies? That's exactly what happened to Babu Sivadasan, who was rejected by nine firms before landing his first job out of college, a job he still calls the best deal he ever made. Babu is a serial entrepreneur and engineer who co-founded stamps.com and later co-founded Envestnet, two category-defining platforms in commerce and wealth management technology. He's now the founder of Jiffy AI, applying artificial intelligence to how software gets created and deployed. In this episode, Babu traces a 1990s patent that became stamps.com, a demo computer damaged in his suitcase before a make-or-break Postal Service pitch, and an accidental pivot into wealth management that led to Envestnet. He also shares why he believes natural language will replace traditional programming, and how that belief now drives Jiffy AI. Whether you're weighing whether to raise capital or curious how AI is reshaping wealth management technology, this conversation offers a rare, three-decade view of how founders build through very different technology eras.WANT TO BE A GUEST ON DEALQUEST?Apply here: https://beaguestondealquest.com/guest FOR MORE ON BABU SIVADASAN: https://www.jiffy.ai  FOR MORE ON COREY KUPFER: https://www.linkedin.com/in/coreykupfer/ https://www.coreykupfer.com/ Corey Kupfer is an expert strategist, negotiator, and dealmaker. He has more than 35 years of professional deal-making and negotiating experience. Corey is a successful entrepreneur, attorney, consultant, author, and professional speaker. He is deeply passionate about deal-driven growth. He is also the creator and host of the DealQuest Podcast. Get deal-ready with the DealQuest Podcast with Corey Kupfer, where like-minded entrepreneurs and business leaders converge, share insights and challenges, and success stories. Equip yourself with the tools, resources, and support necessary to navigate the complex yet rewarding world of dealmaking. Dive into the world of deal-driven growth today! Episode Highlights with Timestamps [02:20] - Rejected by nine firms before landing his first job [05:17] - The 1990s patent that became stamps.com [13:19] - A damaged demo computer and a make-or-break Postal Service pitch[25:15] - The accidental pivot into wealth management [32:41] - Unifying a fragmented advisor tech stack at Envestnet [54:06] - Jiffy AI today: Series B funded, $61 million raised Guest Bio Babu Sivadasan is a serial entrepreneur with deep experience building and scaling public companies backed by a strong engineering foundation. He co-founded stamps.com and later co-founded Envestnet, helping shape category-defining platforms in commerce and financial services. He is now the founder of Jiffy AI, applying natural language AI technology to how software is created and deployed for the wealth management industry. Babu is also an active angel investor and mentor, supporting startups across Silicon Valley and India. Related Episodes Episode 328 - Richard Manders: a fellow engineer-turned-founder whose curiosity about how things work led him from an early career in automation to building and scaling multiple companies with private equity backing. Episode 370 - Gerry Hays: explores how collapsing startup costs and artificial intelligence are reshaping who can raise capital and become a founder, a theme that runs through Babu's own move from the cloud era into the AI era. Episode 350 - Tom Dillon: examines when founders should look beyond venture capital for funding, a question Babu faced directly in the cash-strapped early days of stamps.com.

"Give me a price, I'll give you a structure. Give me a structure, I'll give you a price." In this solocast, Corey Kupfer takes that favorite saying of his and uses it to unpack a handful of the deal world's most repeated cliches, testing which ones hold up and which ones only apply in certain situations. Corey has spent more than 35 years structuring and negotiating deals, and in this episode he draws on that experience to walk through what's really behind a purchase price, a valuation multiple, and a few tax and entity assumptions sellers often take as gospel. WHAT YOU'LL LEARN: Corey breaks down what actually makes up a deal structure, from escrow and promissory notes to earnouts and rollover equity, and why "give me a price, I'll give you a structure" is the question that should come before you get excited about a top line number. He also digs into why comparing multiples without knowing what they're calculated on is misleading, when the advice to take cash up front actually applies, and why he pushes back on the idea that most businesses can't be scaled or sold. KEY INSIGHTS: A purchase price is never just one number. Escrow holdbacks, contingent payments tied to retention, earnouts tied to growth targets, and rollover equity can all sit inside a single deal, and each one carries different risk and different timing. Multiples are almost never apples to apples. Most quoted multiples are calculated on adjusted EBITDA, and buyers can adjust that number differently, which means a higher multiple doesn't always mean a higher price. Take cash up front is better advice for Main Street, owner operator deals than it is for the middle market and up, where professional buyers and PE backed firms have more reputational reasons to pay what they owe. The S Corp regret Corey heard at an industry event traced back to a missed QSBS election, not to S Corps being universally worse. Entity structure decisions depend on industry, timing, and ownership goals, not blanket rules. Corey doesn't believe in unscalable businesses, only businesses that haven't found their systems yet. The same logic applies to sellability, most businesses that can't sell today can become sellable with the right changes. Perfect for entrepreneurs preparing for a sale, raising capital, or negotiating a licensing or royalty deal who want to ask sharper questions before they get anchored on a number. WANT TO BE A GUEST ON DEALQUEST?Apply here: https://beaguestondealquest.com/guest FOR MORE ON THIS EPISODE:https://www.coreykupfer.com/blog/dealcliches FOR MORE ON COREY KUPFERhttps://www.linkedin.com/in/coreykupfer/ https://www.coreykupfer.com/ Corey Kupfer is an expert strategist, negotiator, and dealmaker. He has more than 35 years of professional deal-making and negotiating experience. Corey is a successful entrepreneur, attorney, consultant, author, and professional speaker. He is deeply passionate about deal-driven growth. He is also the creator and host of the DealQuest Podcast. Get deal-ready with the DealQuest Podcast with Corey Kupfer, where like-minded entrepreneurs and business leaders converge, share insights and challenges, and success stories. Equip yourself with the tools, resources, and support necessary to navigate the complex yet rewarding world of dealmaking. Episode Highlights with Timestamps:01:01 - The famous deal world saying, give me a price, I'll give you a structure, and why it matters 03:45 - What's actually inside a deal structure, escrow, promissory notes, and contingent payments 06:24 - Why comparing multiples without knowing what they're calculated on is misleading 09:08 - When take cash up front is real advice, and when it isn't 13:41 - The S Corp story from an industry event and the QSBS election behind it 16:45 - Why Corey believes every business is potentially scalable and sellable Related Episodes:Episode 328 with Richard Manders, for a deeper look at multiple arbitrage and how buyers think about valuation multiples. Episode 339 for more on purchase price structures, contingencies, and how retention and earnouts affect what a seller actually collects. Episode 325 with Kelly Finnell, for a related conversation on tax advantaged entity and ownership structures. Keywords/Tags: deal structure, purchase price negotiation, EBITDA multiple, adjusted EBITDA, earnouts, rollover equity, escrow, QSBS, S Corp versus C Corp, business sellability, business scalability, licensing royalties, M&A negotiation, DealQuest solocast

From a two-for-one lawn-mowing deal he negotiated with his neighbor as a kid to founding a holding company that keeps established Virginia businesses in Virginia, Andrew Dunlap shares his data-driven origin story, a fund built to avoid short-term pressure, and why he believes trust is the only currency that always matters. Andrew is the founder and CEO of Harbor, a long-term, buy-and-hold company that acquires established Virginia businesses and keeps their teams, leadership, and jobs rooted in the state. In roughly two years he has completed three deals, including a CNC machine shop and a FINRA-registered broker dealer, with an industrial services company moving toward close. He describes himself as someone who stumbled backward into this work by digging into merger and acquisition data. WHAT YOU'LL LEARN: You will learn why keeping a company's headquarters local changes how much of its revenue recirculates in the community, how an untimed fund with no AUM fees removes the pressure to make what Andrew calls caffeinated decisions, how Harbor structures flexible deals to become the buyer owners actually prefer, the earnout test that separates a real growth forecast from a wishful one, and why Andrew treats trust as the most durable asset in any market. ANDREW'S JOURNEY: Andrew grew up in Baltimore and moved to Roanoke, in Virginia's southwest, ten years ago. Coming out of a venture-backed startup in Richmond in January of 2024, he noticed how few senior roles existed in his region, then pulled the merger and acquisition databases to find out why. He discovered that 87 percent of external buyers in Roanoke, and 82 percent across Virginia, were from out of state, which meant companies and their leadership kept leaving. The research he found showed that a locally headquartered company recirculates roughly 52 to 53 cents of every revenue dollar in its community, a figure that falls to about 14 cents once the headquarters moves to a larger city. That gap became the foundation for Harbor. TRUST AS THE ONLY CURRENCY: Andrew closed the conversation on a theme he keeps returning to. Trust, he argued, is the one thing that holds when assets turn and revenue streams dry up, and he sees it as underdeveloped in a digital, globalized world where people invest too little in relationships. KEY INSIGHTS: Andrew's foundational insight is that owners care deeply about who becomes the next steward of what they built. He lays out three options for a seller, a strategic buyer, a private equity firm, or a buyer like Harbor that keeps the team in the town where it grew up, and owners consistently choose the path that protects the legacy. Harbor backs that up with flexible structures, using earnouts, seller financing, and varying equity so the deal fits the owner. His most timely insight is that trust outlasts any single asset or revenue stream. When tungsten prices spiked because of China and hit his machine shop, Harbor could call a congressman who came to walk the shop floor. Andrew credits relationships, built in part through writing openly on LinkedIn, for access that does not show up on a balance sheet. Perfect for owners weighing succession, investors interested in longer-hold alternatives to private equity, and anyone curious about how local ownership shapes a regional economy.WANT TO BE A GUEST ON DEALQUEST?Apply here: https://beaguestondealquest.com/guest FOR MORE ON THIS EPISODE: https://www.coreykupfer.com/blog/andrewdunlap FOR MORE ON ANDREW DUNLAP:https://harbor.capital https://www.linkedin.com/in/dunlapandrew/ FOR MORE ON COREY KUPFER https://www.linkedin.com/in/coreykupfer/ https://www.coreykupfer.com/ Corey Kupfer is an expert strategist, negotiator, and dealmaker. He has more than 35 years of professional deal-making and negotiating experience. Corey is a successful entrepreneur, attorney, consultant, author, and professional speaker. He is deeply passionate about deal-driven growth. He is also the creator and host of the DealQuest Podcast. Get deal-ready with the DealQuest Podcast with Corey Kupfer, where like-minded entrepreneurs and business leaders converge, share insights and challenges, and success stories. Equip yourself with the tools, resources, and support necessary to navigate the complex yet rewarding world of dealmaking. Dive into the world of deal-driven growth today! Episode Highlights with Timestamps [00:00:00] - Introduction and overview of Harbor [00:01:48] - Andrew's first deal, a two-for-one lawn-mowing bulk rate [00:02:42] - How he stumbled backward into building Harbor [00:05:05] - The recirculation research, 52 to 53 cents local versus 14 cents once a headquarters leaves [00:13:25] - The untimed fund and avoiding caffeinated decisions [00:21:00] - The Clark Precision Machine acquisition and the owner's five-year contract[00:34:54] - The red flags that kill a deal and the earnout bluff test [00:45:32] - Why trust is the only currency that always matters [00:49:40] - The freedom question Guest Bio Andrew Dunlap is the founder and CEO of Harbor, a holding company that buys established Virginia businesses to keep them in the state. He grew up in Baltimore, moved to Roanoke a decade ago, and came into acquisitions after coming out of a venture-backed startup in Richmond in early 2024, where he had helped build a software company with users in 60 countries. Harbor's leadership also includes M&A and securities attorney Tad Fisher and operations leader Krista Glassburn, who previously ran a manufacturing company in Tazewell, Virginia and grew it from 15 to 190 million dollars while acquiring seven companies. In its first two years, Harbor has acquired a CNC machine shop, a FINRA-registered broker dealer, and moved toward closing on an industrial services company.   Show Description Do you want your business to grow faster? The DealQuest Podcast with Corey Kupfer reveals how successful entrepreneurs and business leaders use strategic deals to accelerate growth. From large mergers and acquisitions to capital raising, joint ventures, strategic alliances, real estate deals, and more, this show discusses the full spectrum of deal-driven growth strategies. Get the confidence to pursue deals that will help your company scale faster. Related Episodes Episode 328 - Richard Manders: How private equity roll-ups create value versus simply aggregating for a multiple arbitrage exit Episode 325 - Kelly Finnell: Using an ESOP as an exit that can preserve a company's independence and reward its people Episode 332 - John Martinka: Buying a business and transitioning from a corporate career into acquisition entrepreneurship   Keywords/Tags Andrew Dunlap, Harbor, buy and hold holding company, keeping businesses local, Virginia acquisitions, mergers and acquisitions, business succession planning, alternative to private equity, earnouts, seller financing, deal structure, CNC machine shop, FINRA broker dealer, metal fabrication, economic recirculation, DealQuest Podcast, Corey Kupfer

From learning Mandarin with nothing but a notebook and a pen on the streets of Wuhan to losing $650,000 of his own money before ever raising outside capital, Sean Weisbrot shares hard-won lessons on cross-cultural dealmaking, bootstrapping versus fundraising, and why LinkedIn visibility now matters for founders and their teams. Sean is the founder of SparkVox, a tool that turns content executive teams are already creating into LinkedIn posts in their own voice, and the host of We Live to Build, a podcast with roughly 235,000 subscribers and more than 320 interviews with seven and eight figure brand owners. He has helped create over $100 million in value across his network and generated more than $15 million in revenue for his own businesses, all while living in China, Vietnam, and now Portugal. WHAT YOU'LL LEARN: You'll discover how a single misstep with a business card or a signing pen can cost a deal before it starts, why 320 founder interviews convinced Sean that bootstrapped founders tend to be happier than funded ones, and how a $400,000 gap between what one investor promised and delivered helped sink his last company. Sean also explains how he now runs a business on roughly $50 a month using AI, and why he believes every founder and executive needs a visible presence on LinkedIn. SEAN'S JOURNEY: Sean had no entrepreneurial role model growing up. What moved him was a pull to leave the US, and after missing a deadline for a teaching program in Japan, he landed in China instead and stayed for ten years, learning Mandarin street vendor by street vendor with a notebook and a pen. His first real deal came in 2016, connecting an American founder with a Chinese investor for a $150,000 raise and earning a $7,500 commission. From there he built a $15 million consulting business helping Chinese and Western companies raise money from each other in the blockchain space. His next venture, a tech company built to compete with Slack, taught him a harder lesson. He put in $650,000 of his own money before raising a $1 million seed round, and a $400,000 shortfall from one investor became a major factor in the company's failure. COVID and a divorce followed, which is part of what led him to Portugal for a fresh start. KEY INSIGHTS: Deal culture varies sharply across countries, down to details like how a business card is received. Corey shared a parallel story about a 1980s deal that nearly stalled at signing over missing ceremonial pens. Founder happiness tracks closely with how a company was funded. Across 320-plus interviews, Sean found bootstrapped founders were generally happier than those who raised capital. A funding gap can sink a company as fast as a bad decision can, as Sean's own $400,000 shortfall proved. AI has collapsed the cost of running a business. Sean's infrastructure now costs about $50 a month, down from roughly $1,000 a month at his last company. Visibility has become a gatekeeper for access, with investors now expecting founders to be active on LinkedIn before they'll even take a call. Perfect for founders weighing whether to bootstrap or raise capital, business leaders working across cultures on deals, and anyone trying to build an authentic presence on LinkedIn.WANT TO BE A GUEST ON DEALQUEST?Apply here: https://beaguestondealquest.com/guest FOR MORE ON THIS EPISODE: https://www.coreykupfer.com/blog/seanweisbrot FOR MORE ON SEAN WEISBROT: https://www.welivetobuild.com/ https://www.linkedin.com/in/seanweisbrot/ FOR MORE ON COREY KUPFER https://www.linkedin.com/in/coreykupfer/ https://www.coreykupfer.com/ Corey Kupfer is an expert strategist, negotiator, and dealmaker. He has more than 35 years of professional deal-making and negotiating experience. Corey is a successful entrepreneur, attorney, consultant, author, and professional speaker. He is deeply passionate about deal-driven growth. He is also the creator and host of the DealQuest Podcast. Get deal-ready with the DealQuest Podcast with Corey Kupfer, where like-minded entrepreneurs and business leaders converge, share insights and challenges, and success stories. Equip yourself with the tools, resources, and support necessary to navigate the complex yet rewarding world of dealmaking. Dive into the world of deal-driven growth today! Episode Highlights with Timestamps:[00:00:00] - Introduction and Sean's background [00:04:20] - Sean's first professional deal in China [00:09:13] - Cultural differences in dealmaking between the US and China[00:26:22] - The capital raising journey behind his last tech company[00:41:03] - What SparkVox does and who it serves [00:53:23] - What freedom means to Sean Guest Bio:Sean Weisbrot is the founder of SparkVox, which turns content executive teams are already creating, sales calls, internal trainings, podcast appearances, into LinkedIn posts in their own voice. He is also the host of We Live to Build, a podcast with roughly 235,000 subscribers and more than 320 interviews with seven and eight figure brand owners. Sean has helped create over $100 million in value across his network, generated more than $15 million in revenue for his own businesses, and raised over $8 million for his businesses and clients. He has angel invested in nine companies with two exits. Fluent in Mandarin, he lived in China for ten years and Vietnam for five before settling in Portugal, where he now lives with his family. Related Episodes: Episode 337 - Jonathan Gardner: Cultural due diligence and what gets lost in translation across German, Japanese, and Chinese deals Episode 370 - Gerry Hays: Democratizing venture capital and when founders should raise versus bootstrap Episode 350 - Tom Dillon: When NOT to take venture capital money and alternative funding sources Keywords/Tags: Cross-cultural dealmaking, bootstrapping versus venture capital, LinkedIn content strategy, AI-powered content creation, blockchain fundraising, founder visibility, personal branding, remote entrepreneurship, cultural due diligence, capital raising