DealQuest Podcast with Corey Kupfer

From experiencing an acquisition early in his career when the AT&T division he worked for was sold to a UK private equity firm, to time at $4 billion Scotts Miracle-Gro where the company created what it called the Integration Factory, Mark Sims shares 25 years of insights on why post-deal integration often determines whether M&A deals succeed or fall short, and why integration planning has to start during due diligence. In this episode of the DealQuest Podcast, host Corey Kupfer sits down with Mark Sims, managing principal of technology solutions at Consult MSG. Mark applies 25 years of experience in strategy, M&A, and information technology across consumer products, retail, manufacturing, and private equity. He has held roles as CEO, Head of Strategy, and CIO, and now leads the technology solutions practice at a firm built around helping middle market PE-backed companies transact, transition, and transform. WHAT YOU'LL LEARN: You'll discover why post-deal integration often determines whether M&A deals succeed or fall short, why integration planning needs to start during due diligence, and what founders selling to private equity should expect when they suddenly have a boss after decades of being the boss. Mark also explains why companies trying to implement AI keep wanting to start at step five before doing the foundational data work. MARK'S JOURNEY: Mark wanted to be an architect as a kid but pursued engineering instead, earning his bachelor's and master's in Industrial Engineering. He started his career in consulting working with Fortune 500 clients, then spent about 15 years at Scotts Miracle-Gro working in corporate M&A at the $4 billion company. About three years ago he moved into the PE advisory space full time. Mark also completed the Advanced Management Program at The Wharton School. THE INTEGRATION ARCHITECT: Mark has lived all three sides of the typical PE deal. Early in his career, he watched a UK private equity firm take over the small AT&T division he worked for, eventually moving headquarters from Cleveland to Houston where the new CEO lived. At Scotts Miracle-Gro, he worked on corporate M&A and was part of the team that created what it called the Integration Factory to snap acquired businesses into the mothership. Today he advises PE-backed middle market companies on building the integration capacity their acquisition pace demands.   FOR MORE ON THIS EPISODE:  https://www.coreykupfer.com/blog/marksims FOR MORE ON MARK SIMS: Website: https://consultmsg.com/ LinkedIn: https://www.linkedin.com/in/markjsims/ 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 [00:01:00] - Introduction to Mark Sims and his background  [00:05:25] - Mark's career arc across public companies, Scotts Miracle-Gro, and PE advisory [00:08:54] - The founder who gets a giant check and discovers they now have a boss [00:17:32] - Why decisive integration protects the people you actually want to keep [00:22:37] - The Integration Factory at Scotts Miracle-Gro [00:29:21] - From PE to public market readiness and the standardization push [00:33:35] - Why companies want to start AI at step five before doing steps one through four [00:40:08] - What freedom means and the ability to pursue interests Guest Bio: Mark Sims is managing principal of technology solutions at Consult MSG. He applies 25 years of experience in strategy, M&A, and information technology across consumer products, retail, manufacturing, and private equity. He has held roles as CEO, Head of Strategy, and CIO, and spent about 15 years at Scotts Miracle-Gro before moving into PE advisory three years ago. Mark holds a bachelor's and master's in Industrial Engineering and completed the Advanced Management Program at The Wharton School. Host Bio: Corey Kupfer is an expert strategist, negotiator, and dealmaker with more than 35 years of professional deal-making and negotiating experience. Corey is a successful entrepreneur, attorney, consultant, author, and professional speaker deeply passionate about deal-driven growth. He is the creator and host of the DealQuest Podcast. 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 337 - Jonathan Gardner on why M&A deals fail because of culture and IT systems Episode 324 - Sejal Lakhani-Bhatt on why tech due diligence determines what you're actually buying Episode 350 - Tom Dillon on understanding business valuation and exit planning realities Episode 366 - Jodi Hume on founder exits and the emotional journey behind major business decisions Keywords/Tags: post-deal integration, M&A integration strategy, private equity portfolio companies, Scotts Miracle-Gro integration factory, founder selling to PE, middle market M&A advisory, technology integration after acquisition, ERP implementation, integration during due diligence, culture integration M&A, PE to public market readiness, AI implementation for businesses, AI policy for companies, Consult MSG, transact transition transform, corporate development integration, people money systems, PE-backed middle market, post-acquisition integration, deal-driven growth

From sandblasting pipe yards at 17 to advising on $10-200M M&A transactions, Dr. Greg Waller shares proven strategies for maximizing business exit value, managing buyer expectations, and why the best time to prepare for sale is 3 years before you're ready. In this episode of the DealQuest Podcast, host Corey Kupfer sits down with Dr. Greg Waller, who advises clients on complex business valuation and buy-side and sell-side M&A transactions. Greg is the managing partner of Cornerstone Valuation and a partner and managing director of Transact Capital, leading a 20-person team focused on the lower middle to middle market. Given his academic and entrepreneurial background, he jokingly refers to himself as the Blue Collar Scholar. WHAT YOU'LL LEARN: In this episode, you'll discover why professional buyers and owner-operators require completely different M&A processes, how to set realistic expectations about the gap between business value and market price, and why starting exit preparation 3 years in advance dramatically impacts final sale outcomes. Greg explains how private equity-backed platforms are blurring the traditional lines between financial and strategic buyers, what makes labor-intensive businesses particularly attractive in the current market, and the cultural complexities that emerge in international transactions. You'll also learn why the most successful exits often begin as casual conversations years before any actual sale decision. GREG'S JOURNEY: Greg's path to M&A advisory started in Youngstown, Ohio at age 17. He walked into a pipe yard with a 4-inch piece of pipe, half sandblasted and coated, half rusty. He showed the crew his before-and-after demo and landed a contract to blast the entire yard over 18 months. That first deal led to years painting elevated structural steel, bridges, water tanks, and radio transmission towers. The industry changed when EPA regulations around lead-based paint removal came in. Working on a bridge one day, a coworker with cracked hands from years of painting looked at Greg and said, "Look at my hands, look at my face. What are you doing? You're a smart boy, why don't you go back to school?" That conversation took the rest of the season to sink in, but Greg eventually left the painting business and pursued his MBA at Ohio University. Faculty members encouraged him to pursue a PhD. His initial reaction was "Are you crazy? Why would I ever want to do a PhD?" But they convinced him, and he earned his PhD in finance at Purdue University. During his 20 years in academics at Ohio University and Virginia Commonwealth University (until May 2025), Greg maintained entrepreneurial ventures including valuation work as an expert witness, real estate development, buying his father's distribution company, and building a restaurant operating group. THE BLUE COLLAR SCHOLAR: Greg's unique combination of blue-collar operations experience and academic expertise gives him a perspective most M&A advisors lack. As he puts it, "I'm as comfortable talking to the janitor as I am to a board of directors, and just being able to put yourself in those shoes and having done it really gives you a different perspective." Having been under the hood of companies across virtually every industry through ownership and valuation work, he can get into the head of sellers in ways that matter when emotions run high and expectations need managing. KEY INSIGHTS: The M&A market divides into two buyer pools requiring vastly different processes. Professional buyers (private equity and strategics) respond to structured competitive auction processes with rigorous due diligence. Owner-operators typically engage through market-making platforms where price leads the conversation. Understanding which buyer type you're targeting shapes everything about your approach. Value and price represent fundamentally different concepts. Greg uses GameStop as his example: price went through the roof despite no fundamental change to the company, then crashed. Setting realistic expectations upfront with clients about valuation ranges prevents painful surprises when market realities emerge. The critical question: "If this thing ends up pricing at the lower end of the range, are we still good to go?" The consultative approach produces the best outcomes. Greg's most successful deals were "3 or 5 years in the making" where he identified value drivers early, helped clients clean up their operations, and positioned them properly before market entry. The best time to start thinking about hitting the market is 3 years ago. Private equity-backed platforms now dominate middle-market transactions, acting like strategics by bolting on competitors but bringing institutional capital discipline. This hybrid model has made the traditional financial versus strategic buyer distinction increasingly blurry. Labor-intensive businesses with skilled workforces are commanding premium multiples as immigration policies create labor challenges. Service providers to infrastructure industries and staffing companies are particularly hot. With massive private equity dry powder and 2024's weak M&A activity, the ingredients point toward a robust 2026 market. Perfect for business owners planning exits in the next 3-5 years, entrepreneurs considering M&A advisory relationships, and anyone interested in understanding how blue-collar operations experience combined with academic expertise creates differentiated advisory value. FOR MORE ON THIS EPISODE: https://www.coreykupfer.com/blog/gregwaller FOR MORE ON GREG WALLER:https://www.linkedin.com/in/h-gregory-waller-7193bb60/https://www.facebook.com/profile.php?id=61573615328301 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 [00:12:39] - Introduction: Greg Waller's credentials and Blue Collar Scholar background [00:16:32] - First deal at 17: Landing the pipe yard sandblasting contract [00:20:04] - The bridge painter who told him to go back to school and career transformation [00:29:05] - How blue-collar and academic backgrounds create unique M&A advisory perspective [00:30:48] - Two buyer pools: Professional buyers versus owner-operators and their different processes [00:35:57] - Value versus price conversation and the GameStop example [00:47:05] - "The best time to start thinking about hitting the market is 3 years ago" [00:48:21] - Why the line between financial and strategic buyers is increasingly blurry [00:50:15] - International deal complexities and cultural differences [00:54:19] - Market outlook for 2026: Labor challenges driving premium multiples [00:57:40] - What freedom means: Clean conscience and ability to chart your own destiny Guest Bio Dr. Greg Waller advises clients on complex business valuation and buy-side and sell-side M&A transactions. He is the managing partner of Cornerstone Valuation and a partner and managing director of Transact Capital, leading a 20-person team focused on the lower middle to middle market ($10-200M enterprise value range). His key industry verticals include human resource companies, staffing, industrials and infrastructure, healthcare, technology, and consumer products. Greg holds a PhD in finance from Purdue University and, until May 2025, was a tenured professor at Virginia Commonwealth University, where he taught courses and published research on corporate finance, mergers and acquisitions, and corporate governance. He previously taught at Ohio University. Greg is the son of a blue-collar entrepreneur and owned and operated an industrial painting company specializing in elevated structural steel infrastructure before pursuing his academic career. He has also been a partner in a real estate development firm and restaurant operating group, and now owns his family's industrial painting equipment distribution company. Given his academic and entrepreneurial background, he jokingly refers to himself as the Blue Collar Scholar. Host Bio Corey Kupfer is an expert strategist, negotiator, and dealmaker with more than 35 years of professional deal-making and negotiating experience. Corey is a successful entrepreneur, attorney, consultant, author, and professional speaker deeply passionate about deal-driven growth. He is the creator and host of the DealQuest Podcast. 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 350 - Tom Dillon: Understanding Business Valuation and Exit Planning Realities Episode 325 - Kelly Finnell: Using ESOPs in Ownership Succession Planning Episode 330 - Pete Mohr: Building Enterprise Value and Exit Readiness Episode 339 - Solocast 74: Equitizing Key Employees and Succession Planning Strategies Follow DealQuest Podcast: LinkedIn: https://www.linkedin.com/in/coreykupfer/ Website: https://www.coreykupfer.com/ Follow Greg Waller:https://www.linkedin.com/in/h-gregory-waller-7193bb60/https://www.facebook.com/profile.php?id=61573615328301 Keywords/TagsM&A advisory, business valuation, exit planning, sell-side advisory, lower middle market, professional buyers, strategic buyers, private equity, business sale preparation, enterprise value, Blue Collar Scholar, deal structuring, owner-operators, business exit strategy, middle market M&A, exit readiness, business succession planning, international M&A, cross-border transactions, 2026 market outlook

From ten years of entrepreneurial struggles to PE exit in three years, Josh Davis shares proven strategies for scaling through acquisitions, building proprietary systems, and navigating the identity shift that follows a successful exit. In this episode of the DealQuest Podcast, host Corey Kupfer sits down with Josh Davis, CEO of JL Davis Enterprises, a five-time founder, business acquirer, and turnaround expert with multiple exits including to a US private equity-backed firm. Josh built one of Canada's fastest-growing logistics startups alongside his wife Loretta, scaling it from the ground up before it was acquired by one of North America's largest transportation companies just three years after launch. WHAT YOU'LL LEARN: In this episode, you'll discover how to scale a company through strategic acquisitions without outside capital, why building proprietary software became a major competitive advantage, and what the post-sale transition really feels like when you stay on as CEO. Josh shares the visionary and integrator partnership dynamic that creates breakthrough results, why most post-exit entrepreneurs struggle with minority investments, and what freedom means when you deliberately keep your family office smaller than outside investors want. JOSH'S JOURNEY: Josh's entrepreneurial drive started early watching both grandfathers build successful businesses. On his mother's side, his grandfather ran a construction company, warehouse business, and real estate ventures. On his father's side, his grandfather was a successful mining entrepreneur who became Josh's closest mentor. But Josh also saw his parents go through financial struggles and divorce, which made him view entrepreneurship as the path to stability rather than risk. In his early twenties, Josh dropped out of business school when his grandfather became sick with cancer. He spent two years learning about business and understanding how to acquire distressed mining properties. After his grandfather passed, Josh got exposure to acquisitions, due diligence, and integration through his grandfather's connections. But for the first ten years, he didn't understand the real importance of building teams, building systems, and building a real company. THE TURNING POINT: At twenty-eight, Josh made a deliberate decision to actually learn how to be an entrepreneur. He read every business book he could find, connected with mentors, and joined a private peer advisory group with seasoned entrepreneurs in their sixties, seventies, and eighties. That group has been a game-changer for thirteen years. A few years later, he married his wife Loretta. Their skills were completely opposite. Josh was the visionary with strengths in leadership and sales. Loretta brought systems, processes, and operational excellence from her commerce degree at one of Canada's top universities. The combination created the breakthrough. BUILDING THE LOGISTICS COMPANY: When Josh and Loretta launched their logistics company, they realized the Canadian transportation industry was old school with manual processes and paper systems. They couldn't find software that fit their needs, so they hired four developers and built their own. After eight months, they launched custom software that tracked gross profit per head, enabled profit-sharing structures, and attracted top talent. The second key was acquisitions. They bootstrapped with bank debt and systematically acquired distressed transportation and warehousing businesses, bringing in their own software, systems, and team members. After developing their operating system for acquisitions, each deal got easier. THE PE EXIT: The conversation about selling started when Loretta raised it. She was pregnant with their first child and knew she didn't want to run operations in a 24/7 transportation logistics business. They had also hit a capital constraint since the low-margin business required more capital every time they grew. They engaged an M&A advisor and found a well-capitalized US private equity-backed firm with Canadian roots in North American transportation. POST-SALE TRANSITION: Josh describes post-exit life as giving a child up for adoption and living in the same house. He stayed on as CEO for two years, and having financial backing from the larger entity was a huge relief. But when the transition ended, his partners were gone, his wife had been out for two years, and the company had become more corporate. The day he told the team was emotional, and when his email was finally turned off, the quiet was striking. KEY INSIGHTS: Josh's original plan post-exit was to take small equity positions and sit on boards. What he found was that he actually likes getting his hands dirty, and working with founders who weren't ready for the advice proved challenging. Some founders would realize they didn't want to do the work and would ask Josh to buy them out instead. That misalignment led JL Davis Enterprises to pivot toward full acquisitions while being highly selective about minority investments. FREEDOM AND FAMILY OFFICE: Josh and Loretta deliberately keep JL Davis Enterprises smaller than outside investors want because they prefer the freedom to choose who they invest in and which organizations they support. Without outside capital, they can make investments directly to help kids at risk and support causes they care about. Perfect for entrepreneurs considering acquisitions as a growth strategy, founders preparing for PE exits, business owners figuring out what comes after they sell, and anyone interested in how the visionary and integrator partnership creates breakthrough results. FOR MORE ON THIS EPISODE:https://www.coreykupfer.com/blog/joshdavis FOR MORE ON JOSH DAVIS: https://jldavisenterprises.com https://www.linkedin.com/in/scaling-with-josh-davis/ 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] - Introduction: Josh Davis' journey from serial entrepreneur to PE exit and family office [05:55] - First entrepreneurial experiences and the first ten years of learning [10:36] - The sailing storm that taught lessons about leadership and preparation [14:00] - The turning point at 28 and joining a private peer advisory group [19:32] - Building the logistics company from startup to PE exit [24:59] - Growth through acquisitions and developing a repeatable integration playbook [31:27] - How the PE exit conversation started and engaging an M&A advisor [36:47] - The two-year transition structure and deciding to step down [46:56] - Lessons from minority investing and pivoting to full acquisitions [50:12] - What freedom means: the ability to choose and support the next generation Guest Bio: Josh Davis is a five-time founder, business acquirer, and turnaround expert with multiple exits including to a US private equity-backed firm. Known for scaling underperforming companies fast, Josh blends grit, faith, and operational excellence to help founders grow with clarity and purpose. As Co-Founder and CEO, he built one of Canada's fastest-growing logistics startups, scaling it from the ground up before it was acquired by one of North America's largest transportation companies just three years after launch. Today he runs JL Davis Enterprises alongside his wife Loretta, acquiring businesses and consulting founders on how to scale, build high-performance teams, and prepare for exit. Grounded in faith and family values, Josh brings a no-fluff, people-first approach to business. He's been named one of Canada's Top 40 Under 40 and believes true success means building a business that serves your life, not the other way around. Host Bio: Corey Kupfer is an expert strategist, negotiator, and dealmaker with more than 35 years of professional deal-making and negotiating experience. Corey is a successful entrepreneur, attorney, consultant, author, and professional speaker deeply passionate about deal-driven growth. He is the creator and host of the DealQuest Podcast. 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 366 - Jodi Hume: Founder Exits and the Emotional Journey Behind Major Business Decisions: Explore the psychological dimensions of exits and what founders need to prepare for beyond the transaction. Episode 336 - Devan Gonzalez: Building a Franchise Empire Through Visionary-Integrator Partnership: Learn how complementary skill sets between business partners create breakthrough results. Episode 350 - Tom Dillon: When NOT to Take Venture Capital Money: Discover alternative funding sources and how to evaluate whether outside capital is right for your business model. Episode 332 - John Martinka: Acquisition Entrepreneurship and Building Companies Worth Buying: Master the fundamentals of acquiring and operating businesses for long-term success. Episode 302 - Laurie Barkman: Preparing for a Successful Exit with Business Transition Insights: Learn the practical steps for getting your business exit-ready. Social Media: LinkedIn: https://www.linkedin.com/in/coreykupfer/ Website: https://www.coreykupfer.com/ Follow Josh Davis: LinkedIn: https://www.linkedin.com/in/scaling-with-josh-davis/ Company: https://jldavisenterprises.com Keywords/Tags: PE exit, private equity acquisition, startup to exit, logistics company sale, family office investing, post-exit transition, scaling a business, turnaround expert, visionary integrator partnership, business acquisition strategy, bootstrapping, growth through acquisitions, proprietary software, integration playbook, founder identity, post-sale transition, minority investments, consulting founders, high-performance teams, entrepreneurship, dealmaking

From investment banker to crypto fund strategist, Stas Sukhinin shares insider perspectives on how credit committees really make decisions, why over-leveraged companies fail fast during downturns, and where stablecoins are creating trillion-dollar transaction opportunities. In this episode of the DealQuest Podcast, host Corey Kupfer sits down with Stas Sukhinin, a finance veteran with over 19 years of experience spanning investment banking, corporate lending, and alternative asset management. Stas began his career at internationally recognized institutions including UniCredit and Societe General, where he helped pioneer mezzanine loan products in Eastern Europe. By age 29, he had become a senior partner at one of the region's largest mezzanine lenders, managing a team of 20 finance professionals and overseeing a $450 million loan portfolio. WHAT YOU'LL LEARN: In this episode, you'll discover what really happens inside credit committees when your loan application gets reviewed and why factors unrelated to your business can determine outcomes. Stas explains how strong companies can go from healthy to restructuring in just three to four months when leverage catches up with them, and the critical difference between how first-time owners and experienced operators approach debt decisions. You'll learn the two key factors that determine how much debt your business can handle, why working capital provisions in purchase agreements deserve more attention than most buyers give them, and how sellers legally present financials in the most favorable light. The conversation also covers Stas's experience investing in the 2017 ICO boom where 90% of projects went to zero but winners returned 50x to 100x, why venture capital investors sometimes block deals that would be life-changing for founders, and where stablecoin transaction volume is already reaching trillions while most people remain unaware. STAS'S JOURNEY: Stas's path into finance started at age 14 when a classmate brought a business magazine to school. Reading about business owners selling companies for millions crystallized his direction. He knew he wanted to be in corporate lending where he could see businesses, analyze financials, and speak directly with owners while working with numbers at a bank. His first role as a junior credit analyst gave him exactly that. He progressed from working with small businesses that had no financials to mid-sized companies to large corporations. Each step taught him more about how deals really get done from inside the institutions making funding decisions. CREDIT COMMITTEE INSIGHTS: Stas pulls back the curtain on what actually happens when loan applications reach credit committees. The reality differs dramatically from what most business owners imagine. Factors affecting approval can seem completely unrelated to the specific deal. Maybe the bank already has a competitor in their portfolio. Maybe the receivable financing department has a different relationship with someone in your industry. One offhand comment from a committee member who hasn't read the full memo can change the entire trajectory of a conversation or result in higher interest rates. DEBT MANAGEMENT LESSONS: The pattern Stas has seen destroy companies in months follows predictable steps. Revenue drops or stagnates. Margins deteriorate because of increased competition and client uncertainty. Debt ratios that looked comfortable suddenly reach concerning levels. Refinancing options disappear just when needed most. Interest rates climb. Everything compounds simultaneously. The difference between experienced and first-time business owners comes down to scenario planning. Experienced operators build safety margins and stress-test assumptions. First-time owners assume conditions will continue as they are. That assumption determines survival. ALTERNATIVE INVESTMENTS: Stas joined a crypto investment fund at its inception in 2017 during the ICO boom. Out of many investments, approximately 90% went to zero. The winners returned 50x or 100x. His observation about liquidity cycles was particularly interesting. Traditional venture now averages seven-year holding periods while crypto projects can reach liquidity events in three or four years through token distributions. On stablecoins, Stas sees enormous opportunity in programmable money. Transaction volume is already in the trillions though most people in developed countries don't realize the scale. Goldman Sachs reportedly reduced bond settlement time from three days to minutes using blockchain technology. Perfect for business owners considering debt financing, entrepreneurs navigating capital raising, and anyone interested in how credit decisions really get made and where alternative investments are creating new opportunities. FOR MORE ON THIS EPISODE: https://www.coreykupfer.com/blog/stassukhinin FOR MORE ON STAS SUKHININ: https://www.thesourcer.so https://www.linkedin.com/in/stassukhinin/ 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] - Introduction: Stas Sukhinin's 19 years in finance from investment banking to crypto [03:26] - First deal experience: Structuring a real estate development loan with disbursement tied to sales  [05:47] - Hidden factors: Why deals get rejected for reasons unrelated to underwriting criteria[08:20] - Committee dynamics: How one comment from an uninvolved member changes deal trajectories [11:41] - Timing and instruments: When companies use the wrong type of capital [15:55] - Risk assumptions: The difference between first-time and experienced business owners [18:29] - Volatility factors: How income stability determines appropriate leverage levels  [21:09] - M&A implications: Structuring adjustment provisions for concentration risk  [24:09] - Liquidity advantages: Why crypto offers shorter holding periods than traditional venture[27:55] - Venture math: The story of a VC blocking a life-changing exit for 1x returns [29:27] - Due diligence limitations: Legal ways sellers present favorable financials  [32:14] - Stablecoins explained: Digital tokens designed to maintain dollar parity  [36:31] - Programmable money: Smart contracts that execute automatically on conditions  [38:00] - Financial advisory services: How Stas helps business owners understand their financials[39:14] - Freedom defined: Removing gatekeepers and accessing financial systems without barriers Guest Bio: Stas Sukhinin has over 19 years of experience in finance spanning investment banking, corporate lending, and alternative asset management. He began his career at internationally recognized institutions including UniCredit and Societe General, where he helped pioneer mezzanine loan products and shaped the market in Eastern Europe. By age 29, Stas had become a senior partner at one of the region's largest mezzanine lenders, managing a team of 20 finance professionals and overseeing a $450 million loan portfolio. He later served on boards of several private companies, deepening his expertise across credit investments and corporate governance. Recognizing early opportunities in alternative assets, Stas joined a crypto investment fund at its inception in 2017 and continues to lead its strategy and operations. He now helps business owners run more efficiently from the lens of financials through his advisory practice. Host Bio: Corey Kupfer is an expert strategist, negotiator, and dealmaker with more than 35 years of professional deal-making and negotiating experience. Corey is a successful entrepreneur, attorney, consultant, author, and professional speaker deeply passionate about deal-driven growth. He is the creator and host of the DealQuest Podcast. 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 350 - Tom Dillon: When NOT to Take Venture Capital Money: Explore alternative funding sources including private credit, SBA loans, and sale-leasebacks with a fractional CFO who works with startups on capital strategy. Episode 370 - Gerry Hays: Democratizing Venture Capital Through VentureStaking: Discover alternative approaches to early-stage investing that don't require massive checks or exclusive networks. Episode 85 - Nick Adams: Seed Stage Venture Capital Funds: Understand how traditional VCs think about early-stage deals and what metrics they evaluate from the investor perspective. Episode 351 - Solocast: Deal Structures Beyond M&A and Capital Raising: Learn about joint ventures, strategic alliances, licensing agreements, and other creative partnership models for business growth. Episode 324 - Sejal Lakhani-Bhatt: Tech Due Diligence in M&A: Explore how technology systems and cybersecurity impact business valuation and deal outcomes. Episode 330 - Pete Mohr: Preparing Your Business for Exit: Understand why sellers often cause deals to fail and how to prepare for the emotional aspects of selling a business. Follow DealQuest Podcast: LinkedIn: https://www.linkedin.com/in/coreykupfer/ Website: https://www.coreykupfer.com/ Follow Stas Sukhinin: LinkedIn: https://www.linkedin.com/in/stassukhinin/ Website: https://www.thesourcer.so Keywords/Tags: corporate lending insights, credit committee decisions, debt management for businesses, mezzanine lending, alternative asset management, crypto investment strategy, stablecoin business applications, EBITDA management, leverage risk, working capital due diligence, venture capital exits, ICO investing, blockchain finance, programmable money, business financing, capital structure, due diligence strategies, financial advisory, dealmaking, business growth strategies

From a lumpy 2025 market to building pent-up demand, M&A attorneys Corey Kupfer and Brian Meegan share their frontline perspective on deal trends and what business owners need to know heading into 2026. In this episode of the DealQuest Podcast, host Corey Kupfer sits down with his partner Brian Meegan of Kupfer. to kick off the new year with a candid conversation about the deal market. Together, they've handled dozens of deals totaling hundreds of millions of dollars in purchase price and enterprise value across wealth management, tech, and trade industries nationwide. WHAT YOU'LL LEARN: In this episode, you'll discover why the 2025 M&A market has been "lumpy" with strong activity in certain sectors while others slowed, and how markets normalize uncertainty when clarity takes too long. Corey and Brian discuss tax legislation certainty versus tariff uncertainty pending Supreme Court review, why pent-up demand builds pressure that eventually releases, and how massive PE dry powder creates deployment urgency. You'll learn why equitizing Generation 2 leadership years before an exit improves options and valuation, how trade industries remain attractive due to AI resistance, and what regional differences mean for deal opportunities. DEAL MARKET REALITY: The end of 2024 was intense, and momentum carried into 2025. Yet conversations with colleagues revealed uneven activity nationwide. Wealth management stayed robust while other sectors slowed. Weaker earnings combined with elevated prices created buyer-seller disconnects. CERTAINTY AND UNCERTAINTY: Markets crave predictability. Recent tax legislation provided clarity around R&D credits and SALT deductions. Tariff policy remains uncertain with potential Supreme Court review, creating productivity costs as companies refigure supply chains. PENT-UP DEMAND: When natural deal flow gets suppressed, it builds pressure rather than disappearing. PE firms sit on enormous capital with fund timeline pressures. Money isn't the constraint. Finding opportunities and having clarity to proceed are the real bottlenecks. THE GEN 2 IMPERATIVE: Equitizing key executives years before a potential exit creates tax-efficient structures, makes companies more attractive to buyers, and gives acquirers confidence. Waiting until deal time limits options and hurts valuation. REGIONAL DIFFERENCES: Brian's Denver practice serves different markets than Corey's coastal work. Colorado features strong tech sectors and alternative energy with California migration. Heavy manufacturing concentrates in Arizona and Nevada. TRADE CONSOLIDATION: Professionalization of trades including plumbing, electrical, and HVAC continues after more than a decade. These industries resist AI disruption, making them attractive for stable revenue and consistent fundamentals. Perfect for business owners considering exits, entrepreneurs evaluating opportunities, and anyone wanting frontline perspective on current M&A conditions. FOR MORE ON THIS EPISODE: https://www.coreykupfer.com/blog/brianmeegan2026 FOR MORE ON BRIAN MEEGAN: https://www.kupferlaw.com/ https://www.linkedin.com/in/brian-meegan/ 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] - Introduction: Kicking off 2026 with partner Brian Meegan [02:00] - Why the M&A market has been "lumpy" across sectors [04:00] - Tax policy certainty after major legislation passed [08:00] - 2026 outlook and pent-up demand building pressure  [13:00] - Appreciation for DealQuest listeners and clients [16:00] - The importance of equitizing Generation 2 leadership [18:00] - Tax efficiency and planning equity participation early [22:00] - Heavy manufacturing trends in Arizona and Nevada[28:00] - Optimism for 2026 and where opportunities exist Guest Bio:Brian Meegan is a partner at Kupfer., bringing extensive transactional experience from his Denver-based practice. Brian specializes in M&A transactions and complex deal structures across tech, natural resources, and professional services. His Colorado practice provides unique perspective on regional market dynamics outside traditional coastal centers. Host Bio:Corey Kupfer is an expert strategist, negotiator, and dealmaker with more than 35 years of professional deal-making and negotiating experience. Corey is a successful entrepreneur, attorney, consultant, author, and professional speaker deeply passionate about deal-driven growth. He is the creator and host of the DealQuest Podcast. 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. Related Episodes: Episode 331 - M&A Market Outlook for 2025 with Corey Kupfer: Predictions and survey data about M&A activity expectations. Episode 339 - Why Your Gen 2 Matters in M&A with Corey Kupfer: Succession planning and how next-generation leadership affects deal value. Episode 350 - Building Wealth Through Rental Properties with Tom Dillon: The "sweaty startups" concept and trade industry consolidation. Episode 335 - Sovereign Wealth Funds and the Future of Investment Advisory Deals with Corey Kupfer: New capital sources entering wealth management M&A. Episode 330 - From Operator to Owner with Pete Mohr: Business freedom and reducing owner involvement while maintaining value. Episode 206 - Should Uncertainties in the Market Impact Your Deal-Making? with Corey Kupfer: How external factors should influence deal decisions. Social Media: Follow DealQuest Podcast: LinkedIn: https://www.linkedin.com/in/coreykupfer/ Website: https://www.coreykupfer.com/ Follow Brian Meegan: https://www.kupferlaw.com/ Keywords/Tags: M&A market outlook 2026, deal trends, private equity dry powder, pent-up demand, tariff uncertainty, trade consolidation, equitizing employees, succession planning, wealth management M&A, Gen 2 leadership, tax policy certainty, interest rates, regional deal markets, Colorado tech sector, entrepreneurship, business growth strategies, dealmaking, exit planning, capital deployment, fund timelines

From closing dinner conversations that changed his career trajectory to advising on transactions up to half a billion dollars, Channing Hamlet shares proven strategies for selling businesses at premium valuations through proper preparation, understanding sector-specific value drivers, and creative deal structures. In this episode of the DealQuest Podcast, host Corey Kupfer sits down with Channing Hamlet, Managing Director at Objective Investment Banking and Valuation, who has over 30 years of experience advising business owners on management issues, transaction execution, and business valuation. Channing's firm specializes in lower middle market transactions, typically ranging from $10-25 million up to $100-150 million in value. WHAT YOU'LL LEARN: In this episode, you'll discover how buyer expectations have dramatically shifted over 25 years and why preparation requirements for premium valuations have intensified. Channing explains why clean accounting is no longer optional, how financial projections can make or break your valuation, and the three key value drivers beyond revenue and EBITDA. You'll also learn creative deal structures that can save transactions when traditional financing becomes challenging. CHANNING'S JOURNEY: Channing's path into dealmaking started at the family dinner table, where his father frequently hosted business visitors for dinner conversations about deals and transactions. His pivotal moment came while working at Legg Mason doing M&A, when a patriarch from a third-generation family business pulled him aside at a closing dinner and shared how much the work had changed his family's life. That moment hooked him on helping entrepreneurs and family businesses navigate successful exits. KEY INSIGHTS: In the mid-1990s, private equity firms paid four to six times EBITDA. Today, good companies sell for 10 to 14 times EBITDA, but buyers expect sellers to show up polished and prepared. Channing identifies three major value drivers beyond EBITDA. First, understanding what drives value in your specific sector. Second, building predictability through recurring revenue and systematized operations. Third, clearly articulating your differentiation and unique value proposition. Financial projections matter because selling takes approximately nine months, meaning buyers pay based on projected results, not historical performance. A last-minute budget won't stand up to scrutiny. Channing also shares a creative deal structure where seller financing at 10% interest saved a transaction when traditional bank financing fell through. Perfect for business owners considering an exit in the next 3-5 years, M&A advisors working with lower middle market companies, and anyone wanting to understand what truly drives premium valuations. FOR MORE ON THIS EPISODE: https://www.coreykupfer.com/blog/channinghamlet FOR MORE ON CHANNING HAMLET: https://objectivecp.com https://www.linkedin.com/in/channing-hamlet/ 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] - Introduction: Channing Hamlet's journey from family dinner table conversations to investment banking [02:17] - Growing up around business deal discussions and choosing the outdoor life [03:45] - The closing dinner moment that changed everything at Legg Mason [08:19] - How the M&A landscape has transformed over 25 years [10:26] - Why buyer expectations and preparation requirements have increased   [18:52] - Understanding sector-specific value drivers through the printing industry example  [23:39] - Market outlook for 2023 and beyond [31:43] - The three legs of Objective's valuation practice[40:03] - Finding Objective Capital Partners and getting in touch Guest Bio Channing Hamlet is a Managing Director at Objective Investment Banking and Valuation, focused on leading the firm's valuation advisory service practice and transaction execution for its investment banking services practice. He is a results-driven executive with 30+ years of experience advising owners on management issues, transaction execution, and business valuation. Channing draws on a diverse background that includes direct management experience, strategy consulting, private equity investing, investment banking, and business appraisal experience to advise his clients. He is actively involved in the LA and San Diego business communities and has spoken at numerous organizations including EO. He was chosen as the Investment Banking Visionary for 2022 and 2021 in Banking and Finance magazine. Host Bio Corey Kupfer is an expert strategist, negotiator, and dealmaker with more than 35 years of professional deal-making and negotiating experience. Corey is a successful entrepreneur, attorney, consultant, author, and professional speaker deeply passionate about deal-driven growth. He is the creator and host of the DealQuest Podcast. 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 350 - Tom Dillon: When NOT to Take Venture Capital Money: Explore valuation considerations and preparing for exit from a fractional CFO perspective. Episode 330 - Pete Mohr: Building Exit-Ready Businesses: Discover how to build a business that commands premium multiples through systematization and predictability. Episode 332 - John Martinka: Exit with Style, Grace, and More Money: Learn practical strategies for maximizing value when selling your business. Episode 339 - Solocast 74: Exit and Succession Planning: Corey's insights on preparing for successful business transitions and the importance of advance planning. Episode 88 - Internal Succession Deals: Explore options for transitioning business ownership to next-generation leadership.   Keywords/Tags business valuation, selling a business, M&A preparation, EBITDA multiples, exit strategy, investment banking, lower middle market transactions, sell-side advisory, company valuation, premium valuation, buyer expectations, financial projections, value drivers, private equity, business sale preparation, transaction execution, family business sale, entrepreneurship, dealmaking, business growth strategies

What if losing your life savings on your first investment at age 27 became the catalyst for understanding why 90% of startups get stuck for the same psychological reasons? That's exactly what happened to Dave Hersh, founding CEO of Jive, board partner at Andreessen Horowitz, and author of Reignition. Dave grew Jive from an open-source project to a NASDAQ IPO, bootstrapping to $12 million over five years before raising venture capital. But when he watched Atlassian, a comparison company that started at the same time, stay on their original trajectory and become worth over $20 billion while Jive eventually died on the public markets, he realized fear and insecurity had driven his capital decision rather than genuine strategy. That painful lesson shaped everything Dave now teaches as an executive coach and General Partner at Metamorph Partners. After working with hundreds of stuck companies, he discovered that 90% of failures trace back to the same psychological patterns. Not cash. Not product market fit. Not competition. Subconscious patterns driving decisions without founders knowing. The statistics are sobering. Between 80 to 95% of founders suffer mental health issues while running their companies. Even successful founders have an 85% chance of experiencing depression or struggles for up to 10 years post-exit. Only 15% are truly thriving after they sell. Dave introduces his inner board meeting framework, which helps founders identify the internal parts driving major decisions. The child wanting safety. The hero wanting to save everyone. The warrior that cannot let go. When you understand these patterns, you can work toward compromises that break through stalemates. The conversation covers when and why to raise capital versus bootstrap, the transition process between identities that most founders skip, and the human-first competitive moats that will define success in the AI era. For founders navigating capital decisions, stuck companies, or the complex terrain after exit, this episode offers a different lens on what actually determines outcomes. FOR MORE ON THIS EPISODE: https://www.coreykupfer.com/blog/davehersh FOR MORE ON DAVE HERSH:https://www.linkedin.com/in/davehersh/https://one-in-ten-thousand.beehiiv.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 [00:00] - Introduction: Dave Hersh's journey from dot-com era to executive coaching [02:30] - Growing up in Newport, Rhode Island with no entrepreneurial modeling [05:15] - First entrepreneurial experience: selling ninja weapons to neighborhood kids [07:45] - Arriving in New York on September 10th, 2001 and founding Jive [12:00] - Bootstrapping to $12 million over five years without outside capital [16:30] - The Facebook moment and decision to raise venture capital in 2006 [21:00] - Why founders equate raising money with success and the 10% reality [25:45] - The Atlassian comparison and what could have been a $20 billion outcome [30:15] - Mental health statistics: 80-95% of founders suffer while running companies [34:00] - Post-exit malaise: 85% of successful founders struggle for up to 10 years [43:00] - Identifying internal parts: the child, hero, warrior, and insecure parts [51:30] - Human-first moats in the AI era Guest Bio Dave Hersh is an executive coach, speaker, and investor based in San Francisco with over 30 years of experience in strategy, startups, and conscious leadership. He was the founding CEO of Jive, which he grew from an open-source project to a NASDAQ IPO. He also spent two years as a Board Partner (investor) at the venture capital firm Andreessen Horowitz. He is the author of Reignition, a playbook for helping startups get unstuck and find their breakthrough, and is working on a new book about enlightened leadership in the era of AI. Dave currently serves as General Partner at Metamorph Partners. Host Bio Corey Kupfer is an expert strategist, negotiator, and dealmaker with more than 35 years of professional deal-making and negotiating experience. Corey is a successful entrepreneur, attorney, consultant, author, and professional speaker deeply passionate about deal-driven growth. He is the creator and host of the DealQuest Podcast. 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 366 - Jodi Hume: Founder Exits and the Emotional Journey Behind Major Business Decisions: Explore the psychological dimensions of exits and what founders need to prepare for beyond the transaction. Episode 350 - Tom Dillon: When NOT to Take Venture Capital Money: Discover alternative funding sources and how to evaluate whether VC is right for your business model. Episode 302 - Laurie Barkman: Preparing for a Successful Exit with Business Transition Insights: Learn the practical steps for getting your business exit-ready. Episode 328 - Richard Manders: Post-Exit Transitions and Finding Purpose After Selling Your Company: Understand how successful founders navigate identity after major exits. Social Media Follow DealQuest Podcast:LinkedIn: https://www.linkedin.com/in/coreykupfer/Website: https://www.coreykupfer.com/ Follow Dave HershLinkedIn: https://www.linkedin.com/in/davehersh/ Newsletter: https://one-in-ten-thousand.beehiiv.com/ Keywords/Tags founder mental health, post-exit depression, startup psychology, venture capital decision, inner work for CEOs, executive coaching entrepreneurs, identity after exit, bootstrap versus venture capital, founder burnout, stuck companies, inner board meeting, conscious leadership, Jive Software, Andreessen Horowitz, Reignition book, founder transitions, ego in business, capital raising psychology, entrepreneurial mental health, exit preparation, business identity, human-first leadership, AI era leadership

From losing his $25,000 life savings on his first startup investment to democratizing venture capital for everyday investors, Gerry Hays shares proven strategies for making early-stage investing accessible through VentureStaking while teaching founders outside traditional tech hubs how to raise capital and build sustainable businesses. In this episode of the DealQuest Podcast, host Corey Kupfer sits down with Gerry Hays, founder and CEO of Doriot and Senior Lecturer at Indiana University's Kelley School of Business. Gerry has made 75+ startup investments, taught venture capital for 20 years, and built multiple companies from zero to exit, including HomeYeah.com and Charlie Biggs Food Company. His current mission focuses on expanding venture capital access beyond coastal hubs through innovative funding models. WHAT YOU'LL LEARN: In this episode, you'll discover how to participate in early-stage startup investing with as little as $10 through the VentureStaking model, why the right to invest later in winning companies proves more valuable than over-investing today, and how collapsing startup costs are fundamentally changing capital requirements for founders. Gerry shares strategies for avoiding what he calls "the fool's tax" when making your first investments, the critical importance of backing founders over ideas, and why venture investing resembles poker more than roulette. You'll also learn about building venture ecosystems within universities where students and alumni can collaborate on funding and growth, navigating the decision between raising capital versus bootstrapping your business, and the difference between venture-appropriate businesses versus lifestyle companies. The conversation explores tokenization's potential to create an ownership economy, why cultivation mindset beats consumption thinking for long-term wealth building, and what freedom from scarcity truly means in both dealmaking and life. GERRY'S JOURNEY: Gerry's path into venture capital came through painful education. After leaving law practice after just six months, he made his first investment at age 27, putting his entire life savings of $25,000 into a hazardous waste processing technology. He knew the space intimately from running lobbying for Indiana's Department of Environmental Management. The technology made sense. The market opportunity was clear. But the founder couldn't execute, and Gerry lost everything. That lesson kept him away from startup investing for a decade. Instead, he became a founder himself, launching HomeYeah.com during the dot-com boom. He acquired a small Indianapolis company with 25 lawn signs and built it into the 11th largest real estate company in Indianapolis by transactions, growing from zero to $1.8 million in revenue in just 20 to 24 months. The company sold to Help-U-Sell Real Estate in 2003, but not before Gerry experienced the challenge of raising capital outside traditional tech hubs. After the HomeYeah.com exit, Indiana University invited him to teach a new venture capital course. He's been there since 2004, creating what he calls a bridge between academic theory and real-world startup practice. Meanwhile, he co-founded Charlie Biggs Food Company, scaling it from zero to $10 million in revenue with distribution in over 1,000 retail locations before exiting through a private equity deal. FIRST INVESTMENT LESSONS: That initial $25,000 loss taught Gerry what he calls "avoiding the fool's tax." The fundamental insight was simple but profound. When you invest, you're really investing in founders more than ideas. He was simply a bad picker of founders at that point. The technology expertise didn't matter. Market knowledge didn't matter. What mattered was identifying founders who could execute through inevitable obstacles and pivots. This lesson shaped everything that followed. Gerry wouldn't touch startup investing again for ten years after that loss. When he did return, his approach centered on cultivating relationships with founders over time, watching how they respond to challenges, and building diversified portfolios that acknowledge most investments will fail. VENTURESTAKING MODEL: The VentureStaking approach emerged from Gerry's years of teaching and investing. The model allows investors to participate with as little as $10 in early-stage founders. Instead of writing large checks for immediate equity, venture stakers provide small grants to founders just getting started. If those founders break out and raise a real equity round, the stakers get invited to invest at 10 times their initial stake. The math works elegantly. Out of 25 investments of $10 each totaling $250, you might only see three worth backing in a real round. But when winners emerge, you've earned the right to participate in meaningful equity rounds without the traditional barriers to entry. This democratizes access while maintaining sophisticated portfolio construction principles. Gerry likens venture investing to poker rather than roulette. You play many hands with small amounts. You fold most of them. But when you spot real winners, you bet heavy. This is cultivation versus consumption, a long-term wealth-building game that Warren Buffett exemplifies, having created 99% of his wealth after age 65. THE COLLAPSING COST OF STARTING: One of the most profound shifts Gerry identifies is how startup costs have collapsed. What required $5 million to build ten years ago can now be created in a day for $50 thanks to AI agents, no-code platforms, and cloud services. This changes everything about capital requirements and who can be a founder. This trend combines with tokenization to create what Gerry calls an ownership economy. Instead of owning a few stocks generating passive income, people could hold tokens in 150 companies, each generating small amounts of passive income without traditional barriers to entry. The infrastructure for this future is being built now through blockchain technology and regulatory evolution. UNIVERSITY VENTURE ECOSYSTEMS: Gerry's work brings the VentureStaking model to universities, creating ecosystems where students, alumni, and faculty can participate in funding and building the next generation of startups. Indiana University has 70,000 students and 800,000 alumni. Imagine creating an arena where students pitch ideas, alumni back them with small stakes, and the community participates in the upside when founders succeed. Shared information, shared risk, shared prosperity. This approach captures innovation traditional VCs miss entirely. Founders outside coastal hubs gain access to capital. Alumni gain access to investment opportunities typically reserved for accredited investors with six-figure minimums. Students learn by doing rather than just studying theory. The model scales to any university willing to build the infrastructure. KEY INSIGHTS: Geographic location shouldn't determine access to capital. Gerry experienced this firsthand with HomeYeah.com in Indianapolis. He wasn't in California. He didn't have the right connections. That challenge drives his current work at Doriot, focused on democratizing venture capital for founders and investors outside traditional hubs. The Sam Altman example illustrates how network effects compound. Altman invested $15,000 in Stripe in 2009, now worth $650 million. That wealth creates access to more deals. Those deals create more wealth. The rich get richer not because they're smarter but because they have access. VentureStaking aims to expand that access. Contracts matter, but people matter just as much. Gerry's experience shows that when something seems too easy, like tenants responding unusually quickly to lease documents without redlines for 10-15 year commitments, it raises red flags. You can have perfect legal documents but still face challenges if you're working with the wrong people. THE SHARK TANK STORY: Gerry shares his Shark Tank experience where his former student pitched a business and received a $250,000 offer from Mark Cuban for 35% equity. Gerry advised him that existing SAFEs would push him below 50% ownership. The founder turned down Cuban's offer. That "no" to Mark Cuban kicked off Season 4 of Shark Tank and generated publicity that proved more valuable than the deal itself. The company continued growing without the investment. CULTIVATION VERSUS CONSUMPTION: One of Gerry's most powerful insights addresses how society trains people for consumption rather than cultivation. We've made sports betting legal. Prediction markets are booming. We're training young people about fast-moving money and dopamine hits. But venture investing is a cultivation game. You're dropping seeds into the ground and watching what the universe brings back. He gave a student $5,000 who wanted to build something in the travel industry. The founder pivoted to AI and Shopify and just raised $8 million at a $55 million valuation. That $5,000 investment is now worth over $200,000. The bet wasn't on the idea. It was on a founder who wouldn't quit. That's something you discover by playing the game, getting yourself into wealth-building activities where you're patient, watching, and learning. FREEDOM FROM SCARCITY: When asked about freedom, Gerry's answer cut to something fundamental. Being free from a scarcity mindset is profoundly important. Everything around us reinforces scarcity. But when you let go of that and realize how abundant things really are, it changes how you see opportunities. You can afford to be patient. You can take calculated risks. You can help others succeed knowing there's enough to go around. This mindset applies to venture capital, to dealmaking, to entrepreneurship, and to life. When you operate from abundance rather than scarcity, you see opportunities differently. Capital formation is evolving. The question is whether that evolution will democratize opportunity or concentrate it further. Gerry's betting on democratization. Perfect for investors curious about venture capital but feeling locked out of traditional opportunities, founders outside coastal tech hubs seeking capital, university administrators exploring venture ecosystem development, and anyone interested in how capital formation is evolving to become more accessible while maintaining sophisticated portfolio construction principles. FOR MORE ON THIS EPISODE: https://www.coreykupfer.com/blog/gerryhays FOR MORE ON GERRY HAYS:https://www.linkedin.com/in/gerryhays/ https://doriot.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 [00:00] - Introduction to Gerry Hays and the VentureStaking model [02:15] - Growing up around real estate and finding it boring initially [04:30] - The $25,000 first investment loss and avoiding the fool's tax [07:45] - Launching HomeYeah.com during the dot-com boom and growing to $1.8 million [10:20] - Capital raising challenges outside traditional tech hubs [12:30] - Selling HomeYeah.com to Help-U-Sell Real Estate in 2003 [14:15] - Teaching venture capital at Indiana University since 2004 [16:45] - Building Charlie Biggs Food Company from zero to $10 million in revenue [19:30] - The VentureStaking model explained with $10 minimum investments [22:15] - Why venture investing is poker, not roulette [25:00] - The collapsing cost of starting companies from millions to dollars [27:30] - Tokenization and the ownership economy vision [30:45] - The $5,000 investment now worth $200,000 after founder pivoted to AI [33:20] - Sam Altman's $15,000 Stripe investment now worth $650 million [36:00] - Building venture ecosystems within universities [39:15] - The Shark Tank story where student turned down Mark Cuban [42:00] - Cultivation versus consumption mindset for wealth building [44:30] - Warren Buffett creating 99% of wealth after age 65 [46:45] - Freedom from scarcity mindset in dealmaking and life Guest Bio Gerry Hays is the founder and CEO of Doriot, a platform focused on democratizing venture capital by expanding access for entrepreneurs outside traditional coastal hubs. He is also a Senior Lecturer at Indiana University's Kelley School of Business, where he has taught Venture Capital and Entrepreneurial Finance since 2004. Gerry began his career in politics and law before founding HomeYeah.com, an online real estate platform that grew from zero to $1.8 million in revenue in 20-24 months and became the 11th largest real estate company in Indianapolis by transactions. The company was acquired by the private equity firm behind Help-U-Sell Real Estate in 2003. He co-founded Charlie Biggs Food Company, growing it to over $10 million in annual revenue with distribution in over 1,000 retail locations before exiting through a private equity deal. He also co-founded Apparel Media Group, later acquired by Custom Ink. An active investor, Gerry has backed 75+ early-stage companies, several of which have raised over $20 million or achieved profitability. He has been investing in Bitcoin and Bitcoin Layer 2 infrastructure since 2013. Gerry is the author of The First-Time Founders Equity Bible and has led student venture immersion trips to Asia for over a decade.  Host Bio Corey Kupfer is an expert strategist, negotiator, and dealmaker with more than 35 years of professional deal-making and negotiating experience. Corey is a successful entrepreneur, attorney, consultant, author, and professional speaker deeply passionate about deal-driven growth. He is the creator and host of the DealQuest Podcast. 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 350 - Tom Dillon on Fractional CFOs and Alternative Funding Sources: Learn how fractional CFO services help companies explore diverse funding options beyond traditional venture capital. Episode 351 - Solocast on Deal Structures Beyond M&A and Capital Raising: Explore joint ventures, strategic alliances, licensing agreements, and other creative partnership models that expand growth options. Episode 89 - Sherisse Hawkins on the Capital Raising Journey: Discover the practical realities of securing investment as a founder and navigating the funding landscape. Episode 85 - Nick Adams on Seed Stage Venture Capital Funds: Understand how traditional VCs evaluate early-stage deals and what metrics matter most to institutional investors. Episode 175 - Natasha Miller on Developing Strategic Partnerships: Master the concepts of shared risk, shared resources, and creative collaboration structures that bring communities together. Episode 185 - Maximilian Rast on How to Raise Capital for Your Company: Build the fundamentals of capital raising that apply across venture, real estate, and business growth strategies. Social Media Follow DealQuest Podcast:LinkedIn: https://www.linkedin.com/in/coreykupfer/Website: https://www.coreykupfer.com/ Follow Gerry Hays: LinkedIn: https://www.linkedin.com/in/gerryhays/ Company: https://doriot.com  Twitter: @gerryhays Keywords/Tags venture capital democratization, VentureStaking model, early stage investing, startup funding alternatives, university venture ecosystems, tokenization investing, accredited investor alternatives, cultivation mindset wealth building, venture capital accessibility, startup investment diversification, capital raising strategies, founder backing strategies, angel investing, entrepreneurship education, blockchain tokenization, ownership economy, portfolio diversification, founder selection strategies, dealmaking strategies