Episodios

  • Episode 385: 2026 Deal Outlook and Market Trends with Brian Meegan

    Episode 385: 2026 Deal Outlook and Market Trends with Brian Meegan
    Jan 7 2026
    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 ...
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    33 m
  • Episode 384: Happy Holidays DealQuest Family

    Episode 384: Happy Holidays DealQuest Family
    Dec 31 2025
    About fifteen years ago, I gave up the conversation around balance entirely. The word I use instead is integration, and in this holiday episode I share why that shift transforms how entrepreneurs experience everything from year-end deal closings to family obligations. In this holiday episode of the DealQuest Podcast, I share reflections on 2025, point to must-listen episodes, preview what's coming in 2026, and break down the integration mindset that has shaped my approach to business and life. WHAT YOU'LL LEARN: In this episode, you'll discover why the balance conversation creates unnecessary stress, the four episodes from 2025 worth revisiting, what's coming in January with my partner Brian Meegan, how designing where you live and which clients you take on become integration decisions, why great mergers have integration at their core while failed ones have integration problems, and how clarity creates filters for better decisions. MY INTEGRATION JOURNEY: Balance frames everything as separate competing demands pulling in different directions. Integration creates a lens where choices support multiple priorities simultaneously. Living in Marina del Rey serves integration. Fifteen minutes from LAX. Secure building. Walking my dog along the promenade during breaks. Cold brew moments on the patio before M&A negotiations. Every choice reduces friction. EPISODES WORTH REVISITING: Dave Hersh on Episode 381 delivered one of my favorite interviews ever, sharing hard truths about post-exit challenges through his inner board meeting framework. Bob Bush on Episode 377 told his remarkable journey from East St. Louis to founding Mutombo Coffee with the late Dikembe Mutombo. Jodi Hume on Episode 366 helps founders avoid the regrets that plague up to 85% of entrepreneurs after exits. Hikari Senju on Episode 354 offered a different lens on building AI companies through strategic bootstrapping. WHAT'S COMING IN 2026: January kicks off with my partner Brian Meegan joining to discuss what we're seeing in the deal landscape. Special series are planned diving deep into specific industries similar to our RIA aggregator coverage. KEY INSIGHTS: The great mergers and acquisitions have integration at their core. The ones that fail typically have integration problems. Choosing podcasting over a weekly column reflects integration thinking. This format feels like an extension of who I am rather than an obligation. When you have clarity about what integrates in your life, it creates a filter for decisions, just like whiteboarding sessions create filters for M&A clients. Perfect for entrepreneurs feeling pulled in too many directions, business owners heading into year-end closings, and dealmakers who want to understand how integration principles apply to M&A success. FOR MORE ON THIS EPISODE: https://www.coreykupfer.com/blog/holiday2025 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: Holiday wishes to the DealQuest community [02:00] - Episode recommendations: Four must-listen conversations from 2025 [04:00] - Dave Hersh Episode 381: Psychology behind successful exits "[05:00] - Bob Bush Episode 377: Global dealmaking and Mutombo Coffee [06:00] - Jodi Hume Episode 366: Avoiding post-exit regret [06:30] - Hikari Senju Episode 354: Strategic bootstrapping for AI companies [07:00] - What's coming in 2026 with Brian Meegan [09:00] - The integration versus balance conversation [11:00] - Designing life for integration: Marina del Rey example [14:00] - Integration in deals: Why great M&A has integration at its core [15:00] - Clarity as a filter for decisions [15:30] - Closing thoughts and gratitude Host Bio:Corey Kupfer is an expert strategist, negotiator, and dealmaker with more than 35 years of professional deal-making and negotiating experience. He is the creator and host of the DealQuest Podcast and managing partner of Kupfer PLLC. Show Description: Do you want your business to grow faster? The DealQuest Podcast reveals how successful entrepreneurs use strategic deals to accelerate growth. From mergers and acquisitions to capital raising, joint ventures, and strategic alliances, this show covers the full spectrum of deal-driven growth strategies. ...
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    17 m
  • Episode 383: Sell Your Business for a Premium with Channing Hamlet

    Episode 383: Sell Your Business for a Premium with Channing Hamlet
    Dec 24 2025
    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 ...
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    44 m
  • Episode 382: Building Enterprise Value Through Fee-Based Transitions with David Lau

    Episode 382: Building Enterprise Value Through Fee-Based Transitions with David Lau
    Dec 17 2025
    From chief marketing officer at the first internet bank to building the leading annuity platform for RIAs, David Lau shares proven strategies for raising capital, navigating public company challenges, and why converting commission-based revenue to fee-based can multiply your exit value by five times. In this episode of the DealQuest Podcast, host Corey Kupfer sits down with David Lau, founder and CEO of DPL Financial Partners, who has raised over $500 million across multiple ventures and built DPL into a platform serving more than 10,000 advisors at over 3,500 RIA firms. WHAT YOU'LL LEARN: In this episode, you'll discover why organic growth matters far more than market growth when acquirers evaluate your business, how converting commission-based annuity business to fee-based can multiply both your revenue and your exit multiple, the real tradeoffs of taking institutional capital and signing up for aggressive growth, the critical difference between venture capitalist optimism and private equity scrutiny, and how recognizing when your business has "run its course" can open the door to building something bigger. DAVID'S JOURNEY: David's career began as chief marketing officer of Telebank, the first internet bank, where he helped raise over $500 million. When preparing to go public, the stock jumped from $17 to $150 in weeks before Goldman Sachs stabilized pricing at $105. He later built Jefferson National, an insurance carrier he sold to Nationwide. That experience taught him the valuable part was distribution, not the capital-intensive balance sheet, leading directly to founding DPL in 2018. KEY INSIGHTS: A billionaire David met admitted he "mistook a bull market for brilliance." Acquirers only pay premium multiples for organic growth. If you did nothing different over the last decade as an RIA, you're making twice as much just from market performance. Buyers know this. Converting from commission to fee-based transforms exit potential with three times the revenue and five times the multiple, while expanding your buyer pool. DPL's technology reviews 2,500 policies per hour, and a significant portion of DPL's $4 billion in annuity sales were M&A related. When launching DPL, David planned to bootstrap until meeting Todd Boehly. Taking institutional capital means signing up for aggressive growth where some team members won't make it to the next stage. Venture capitalists are optimists who see your vision. Private equity investors see everything that can go wrong. Perfect for RIA owners considering M&A, hybrid advisors evaluating fee-based transitions, and entrepreneurs weighing capital raising decisions. FOR MORE ON THIS EPISODE: https://www.coreykupfer.com/blog/davidlau FOR MORE ON DAVID LAU: https://www.dplfp.com https://www.linkedin.com/in/david-lau-b6449b7/ https://x.com/dpl_fp 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: David Lau's journey to building DPL Financial Partners [04:00] - Capital raising at Telebank: $500 million raised, stock jumping from $17 to $150 [08:00] - The tradeoffs of taking institutional capital and signing up for aggressive growth [12:00] - Venture capitalists as optimists versus private equity investors who see downside [16:00] - Why choosing the right capital partners matters more than just getting funded [20:00] - How DPL solved the RIA insurance problem with commission-free products [24:00] - Converting to fee-based: Three times the revenue and five times the multiple [28:00] - Why organic growth matters more than market growth in valuations [33:00] - The future of RIA consolidation and when to sell a business [40:00] - Freedom: Working with Russian defectors and gaining perspective Guest Bio David Lau is founder and CEO of DPL Financial Partners, the leading annuity platform for RIAs. Since 2018, DPL has worked with 20 insurance carriers and built an advisor base of more than 10,000 advisors from over 3,500 RIA firms. Before founding DPL, David was COO of Jefferson National, which he helped build and sell to Nationwide. Earlier, he served as chief marketing officer at Telebank, the first internet bank, where he helped raise over $500 million. His work has been covered in The Wall ...
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    42 m
  • Episode 381: The Psychology Behind Successful Exits with Dave Hersh

    Episode 381: The Psychology Behind Successful Exits with Dave Hersh
    Dec 10 2025
    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 ...
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    43 m
  • Episode 380: Build a Winning Deal Program with Strategic Planning

    Episode 380: Build a Winning Deal Program with Strategic Planning
    Dec 3 2025
    From jumping straight to deal structure to building repeatable acquisition programs that scale, Corey Kupfer shares the exact whiteboarding process he uses with clients to create successful deal programs across M&A, joint ventures, licensing, and any deal-driven growth strategy. In this solocast episode of the DealQuest Podcast, host Corey Kupfer walks through the five critical steps that must come before deal structure when building a repeatable deal program. Drawing on 35+ years of deal-making experience and countless whiteboarding sessions that have helped create platforms completing dozens of transactions, Corey reveals why most attorneys start in the wrong place and how proper planning separates successful programs from expensive mistakes. WHAT YOU'LL LEARN: In this episode, you'll discover why deal structure should be the sixth step in your process, not the first, and how to identify your personal and business motivations before pursuing any deal program. Corey shares the five whys technique from Honda's former CEO to uncover your real drivers, how to define your ideal target or partner profile to avoid wasting time on opportunities that don't fit your strategic criteria, and why your value proposition must differentiate you from competitors who may have more capital. You'll learn how to assemble the right deal team with both internal and external expertise, why building a repeatable model before doing individual deals prevents cap table nightmares and integration problems, and the power of having template documents ready to demonstrate you're a serious player. The framework applies whether you're pursuing acquisitions, joint ventures, licensing deals, franchising, or any other deal-driven growth approach. THE WHITEBOARDING PROCESS: Most clients come to Corey asking about deal structure. What should the terms be? Should they pay cash or offer equity? What about earnouts? These are important questions, but they're not where you should start. After doing whiteboarding sessions with countless clients over 35 years, Corey can say with complete confidence that every single one has gotten significant value from the process. The firms that skip these steps end up with inconsistent deal structures, cap table problems, and integration nightmares. The companies that do this right create efficient, repeatable processes that let them scale their deal programs. THE INTERNAL JOURNEY: Corey often talks about things other lawyers don't discuss. He focuses on the internal journey, making sure business leaders and executives move forward on deals from the right place. When you get to wherever you think you want to go, you should actually be happy and satisfied, and it should help you achieve your objectives and goals. Too many entrepreneurs pursue growth strategies based on external pressures or assumptions about what they think they should be doing, based on entrepreneurial wisdom out there. They grow and do things in ways that don't actually end up making them happy and satisfied and aren't necessarily best for their business. STEP ONE: START WITH YOUR WHY: The first question in every whiteboarding session is why. Not just the corporate why, although that matters. Corey wants to know your personal why as the founder or executive driving this strategy. If your why is geographic expansion because your clients need services in other markets, that's legitimate. If your why is adding capabilities that will create a better integrated client experience, that works too. If your why is increasing enterprise value before an exit in five or ten years, there's no judgment about that. You just need to be clear on what drives you, because that clarity will shape every subsequent decision. Corey uses the five whys technique, which comes from the former CEO or chairman of Honda. You ask why five times, going deeper with each question. Why do you want to grow? To get bigger. Why do you want to get bigger? To serve clients better. Why will that serve clients better? Because they have needs we currently send elsewhere, and integration would improve their experience. Why does that matter to you? Because I genuinely care about my clients and believe this will make them happier while helping our company grow. That depth of understanding separates deal programs that succeed from those that become expensive distractions. STEP TWO: DEFINE YOUR TARGET PROFILE: Once you know your why, you can determine who you should be targeting. This is where many firms waste tremendous time and energy. Doing deals is a distraction from running your business, especially if you don't have a dedicated corporate development team with finance people, legal resources, and integration specialists. You need to be surgical about who you pursue. Think about the wealth management space, which Corey works in extensively. There are huge numbers of buyers right now. The market is incredibly competitive. If you're trying to compete with private equity backed ...
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    27 m
  • Episode 379: Democratizing Venture Capital Through VentureStaking with Gerry Hays

    Episode 379: Democratizing Venture Capital Through VentureStaking with Gerry Hays
    Nov 26 2025
    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 ...
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    42 m
  • Episode 378: Building Commercial Real Estate Success Through Strategic Partnerships with Nick Jones

    Episode 378: Building Commercial Real Estate Success Through Strategic Partnerships with Nick Jones
    Nov 19 2025
    From professional wakeboarder to CEO managing $250M+ in commercial real estate investments, Nick Jones shares proven strategies for building successful real estate businesses through strategic partnerships, effective capital raising, and protecting investor interests. In this episode of the DealQuest Podcast, host Corey Kupfer sits down with Nick Jones, CEO of Alakai Capital, who has underwritten and acquired over 70 commercial investments and developments representing more than $250 million in value. Nick currently oversees 800,000+ square feet of industrial, retail, office, and medical assets across multiple states. WHAT YOU'LL LEARN: In this episode, you'll discover how to raise outside capital for your first commercial real estate deal while protecting downside risk, why syndication can work better than funds when you can close deals quickly with trusted investors, and the surprising truth about "off-market" deals versus listed properties in today's transparent market. Nick shares how to build broker relationships that generate consistent deal flow without constantly hunting for opportunities, due diligence strategies when high-credit tenants won't share financial information, and why Covid flipped conventional wisdom about credit tenants versus mom and pop operators. You'll also learn about the strategic value of balancing consistent real estate returns with selective angel investments, how to navigate market trends including drive-through retail and efficiency-focused opportunities, and what freedom means beyond just financial independence. NICK'S JOURNEY: Nick's path wasn't linear. Growing up near Microsoft and Nintendo in Redmond, Washington, he found real estate "incredibly boring" until witnessing how it connected to fascinating industries. After his father and grandfather passed away during his senior year of high school, Nick moved to Florida to pursue professional wakeboarding, eventually earning a podium finish at the World Championships in 2011 while graduating summa cum laude from the University of Central Florida. The dean of UCF's real estate program, whose son was also a professional athlete, reignited Nick's interest in commercial real estate investment and development. Nick started in land brokerage during 2011-2012 when Florida land was worth less than the buildings next to it, learning through challenging cold calls to developers. FIRST DEAL LESSONS: Nick's entry into investing came through a vacant Taco Bell property. Working with a broker partner, they secured the building, signed a 10-year lease with a new tenant, and only had to replace the HVAC and roof. The timing proved fortunate - securing 80% loan to value at 2% interest on an interest-only basis during the post-financial crisis recovery. That first deal taught valuable lessons about protecting downside risk and building tenant relationships while delivering one of his strongest returns ever. CAPITAL RAISING EVOLUTION: For his first capital raise, Nick bought an old bank branch all cash with plans to tear it down and build a quick service restaurant. To protect downside risk as a new sponsor, he structured it with no debt and two years of interest and tax reserves. After approaching friends' parents, fellow brokers, and creating a detailed investment memorandum, a tenant approached wanting to lease the existing building as-is with a 10-year lease. Nick refinanced at 50% LTV, pulled equity out, and used those proceeds to buy a second deal. That snowball effect has grown to approximately 100 investors making about 500 investments with his company. KEY INSIGHTS: Nick continues syndicating individual deals instead of raising funds because his deals follow similar patterns with consistent return theses. This approach gives investors freedom to select which markets and property types align with their preferences while maintaining speed to close. Managing investor capital creates heightened responsibility that sharpens every aspect of deal execution. Nick approaches it similarly to personally guaranteeing loans - while losing your own capital is unfortunate, losing someone else's carries profound implications for relationships and reputation. The biggest lesson from deals that didn't go as planned: contracts matter, but people matter just as much. When tenants respond unusually quickly to lease documents without redlines for 10-15 year commitments, it raises red flags. During Covid, high-credit tenants had attorneys advising them to stop paying rent while small bay industrial mom and pop tenants maintained perfect payment records. BROKER RELATIONSHIPS: The majority of Nick's deals come through brokers he's built long-term relationships with over years. These relationships prove valuable because brokers trust Nick will maintain confidentiality, move quickly through underwriting, and they understand his investment criteria. After years of exchanging deals and feedback, brokers know which opportunities match his thesis. MARKET ...
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