DealQuest Podcast with Corey Kupfer

Corey Kupfer
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Why do some companies grow by leaps and bounds while others only inch forward? Simple. They embrace Deal-Driven Growth in addition to organic growth! DealQuest is where you learn how to strategize, prepare for, find, and complete deals to grow your company faster. Listen in as host Corey Kupfer takes you behind the scenes with some of the world’s most fascinating deal-savvy business leaders. This is the one place where they can share openly the secret to deals they have done (or failed to do) and the issues, opportunities, benefits, pitfalls and lessons learned. Here you learn first-hand all about: Powerful deals that require little capital, mergers, acquisitions, and tuck-ins, Joint ventures, partnerships, and strategic alliances, licensing, raising capital and onboarding key employees, negotiating, structuring, finding, valuing, closing and integrating deals. Don’t be the one at the table who doesn’t grasp the power of Deal-Driven Growth!

  1. Episode 396: Do You Actually Want to Be a Deal Maker with Corey Kupfer

    2D AGO

    Episode 396: Do You Actually Want to Be a Deal Maker with Corey Kupfer

    From year-end deal crunches to honest conversations about risk tolerance and self-knowledge, Corey Kupfer makes the candid case for why deal making may not be for every entrepreneur, and what it actually takes if you decide it is. In this remastered DealQuest solocast, host Corey Kupfer draws from his own experience managing multiple year-end closings while stretched thin to walk through three reasons why deals may not align with every business leader's goals or temperament, and how the flip side of each reason reveals the roadmap for those who do want to pursue deals. WHAT YOU'LL LEARN In this episode, you'll discover why even experienced deal teams face periods of all-encompassing intensity, how risk tolerance shapes whether and how you pursue deals, and why some entrepreneurs are better served by doubling down on organic growth. Corey explains how the CPR tool from his Authentic Negotiating book can help you assess whether deals belong in your growth strategy, and why the distinction between born deal makers and situational deal makers matters. THE HONEST CASE FOR SELF-ASSESSMENT Corey acknowledges the counterintuitive nature of a deal-making advocate telling listeners they might not want to be deal makers. But the premise is grounded in something he returns to throughout his work. Self-knowledge matters more than ambition. The decision to pursue deal-driven growth should come from clarity about what you want, not from external pressure or assumptions. He connects this to the CPR tool from his Authentic Negotiating book, which stands for Context, Purpose, and Results. The CPR framework applies as powerfully to the question of whether deals should be part of your growth strategy as it does to any specific negotiation. Corey also previews his dealmaker retreats, which will begin with visioning work before any deal strategy is discussed. KEY INSIGHTS Deal work is periodically all-encompassing. Corey shares his experience managing multiple year-end closings while sick, with his team stretched. He walks through disclosure schedules in asset purchase deals, where sellers must provide representations and warranties covering contracts, employees, regulatory matters, and taxes. Getting these wrong risks breach and potential indemnity obligations. Risk tolerance is a prerequisite. Every successful deal maker has deals that fail or underperform. Corey shares a live example of risk-averse buyers requesting protections that could burden his client. If deals going wrong would affect your sleep or health, the personal cost may outweigh the benefit. Your highest and best use may not include deal making. Some entrepreneurs generate exceptional results through organic growth. Adding deals could dilute their greatest strength. Corey compares growth diversification to a diversified stock portfolio but notes you can hire the right team to handle deals while you focus on your strengths. Being a deal maker is not binary. There are situational deal makers who evolve into the role because the timing aligns, an opportunity appears, or their mindset shifts. The question is whether this is the right time for you. Perfect for entrepreneurs weighing whether deal-driven growth aligns with their goals, business owners considering M&A or partnerships, and anyone interested in an honest self-assessment framework before committing to a deal strategy. FOR MORE ON THIS EPISODE: https://www.coreykupfer.com/blog/beadealmarker FOR MORE ON COREY KUPFER:LinkedIn: https://www.linkedin.com/in/coreykupfer/ Website: https://www.coreykupfer.com/  Episode Highlights with Timestamps:[00:02:12] - Solocast opens with the counterintuitive premise of why you should not be a deal maker [00:04:53] - Why deal work can be all-encompassing and the demands of year-end closings[00:06:32] - Disclosure schedules in asset purchase deals and why they matter [00:10:25] - The reality of pushing through fatigue and intensity [00:11:57] - The inherent risk of deal making and why some deals will always fail [00:14:01] - Live deal example with risk-averse buyers requesting protections and guarantees[00:14:54] - Organic growth as an alternative path and when deals become a distraction [00:15:53] - Superpower and highest and best use [00:18:25] - Self-knowledge as the foundation and the CPR tool from Authentic Negotiating[00:19:00] - Dealmaker retreats and why they start with visioning [00:21:02] - What it takes to be a deal maker and the concept of situational deal makers 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 326 - Herman Dolce: How People Around You Filter Advice Through Their Own Risk Tolerance Episode 330 - Pete Mohr: Building Enterprise Value and Exit Readiness Episode 323 - Holiday Solocast: Year-End Completion and Clearing Exercise for EntrepreneursEpisode 324 - Sejal Lakhani-Bhatt: Entrepreneurial Mindset, Vulnerability, and Authentic Leadership   Keywords/Tags:deal making mindset, risk tolerance in deals, deal maker self assessment, organic growth vs acquisitions, deal-driven growth strategy, entrepreneur risk tolerance, when not to do deals, self-knowledge in business, authentic negotiating CPR tool, situational deal makers, disclosure schedules, highest and best use, deal-driven growth

    24 min
  2. Episode 395: Building Exit-Ready Businesses with Marty Fahncke

    MAR 18

    Episode 395: Building Exit-Ready Businesses with Marty Fahncke

    From grassroots soccer parks to $600 million exits, Marty M. Fahncke reveals why every dollar of EBITDA sacrificed for tax savings costs you seven on a multiple, how the build versus buy decision needs a reality check, and why a business fully prepared to sell is the best business to own. In this episode of the DealQuest Podcast, host Corey Kupfer sits down with Marty M. Fahncke, CMAA, who has helped hundreds of businesses scale to over $1 billion in combined revenue and executed nearly $500 million in M&A deals. He is the founder of Westbound Road, an M&A advisory firm specializing in digital businesses in the $5-50 million range, and author of Boomer Sells the Business: A Step-by-Step Guide to Cashing Out and Living Large. WHAT YOU'LL LEARN: In this episode, you'll discover why the build versus buy analysis fails when founders underestimate timelines and costs, and why opportunity cost is often the biggest expense that never appears in spreadsheets. Marty explains how combining marketing expertise with M&A strategy creates advantages most advisors lack, the costly trade-off between profit maximization and tax mitigation that saves twenty cents but costs seven dollars on a multiple, and why operational decisions like CRM selection or staffing structure can kill deals worth millions. You'll also learn how the Who Not How philosophy transforms into a powerful acquisition playbook, why SaaS founders who turned down $50 million in 2021 are accepting those valuations were an anomaly, and how authority marketing through podcasts generates clients who arrive ready to sign without sales conversations. MARTY'S JOURNEY: Marty grew up in the mountains of Utah wanting to be either a forest ranger or join the military. Neither path worked out, and he ended up on the entrepreneur path instead. Even as a teenager, he showed entrepreneurial instincts, selling water purifiers and vacuums and running a bicycle rehab business at age twelve. M&A was completely off his radar until he and some friends started a soccer training product company. They took a truly grassroots approach, setting up canopies at local parks every weekend where kids played soccer. Marty had his children demonstrate the product while he sold to parents. Those park sessions taught them exactly what messaging resonated. Marty used those insights to create a marketing campaign that got the product onto QVC in the United States and Japan. Just eighteen months in, they received an unsolicited $1.5 million offer from a private equity firm buying their proven QVC sales channel. His next deal flipped the approach. Instead of building from scratch, Marty and a partner combined two competing businesses, each doing $1.5-2 million in revenue. By eliminating competition and consolidating operations, they scaled from under $4 million to $30 million in two years. That company eventually became part of a $600 million exit through a reverse merger. After that exit, Marty built a personal portfolio of businesses. In 2019, he focused on M&A full-time. When 2020 hit, he saw opportunity in the chaos. He reached out to companies about selling, and economic uncertainty generated many yes responses. When businesses weren't right for his portfolio, sellers asked if he knew other buyers. He started triangulating deals, brought in partner Becky, and launched Westbound Road in 2020. They focus exclusively on digital businesses between $5 and $50 million, including e-commerce, SaaS, publishing, marketing agencies, and virtual professional services. The firm is intentionally small at five people but highly specialized. THE MARKETER'S EDGE: Marty brings a rare combination of world-class marketing expertise and deep M&A experience. Most advisors excel at one or the other, rarely both. He is a marketer at heart and applies marketing principles to M&A strategy. This matters because organic growth drives valuation multiples. Buyers pay premiums for demonstrated growth momentum, often adding an extra turn or two on exit multiples. Marty sees both sides of the equation, knowing how to build marketing systems that drive organic growth and how to structure deals that accelerate inorganic expansion. KEY INSIGHTS: The build versus buy decision requires brutal honesty. Marty sees unreasonable optimism every time founders analyze whether to build or acquire. His rule: double the timeline, triple the costs. Even then, most analyses miss opportunity cost. What revenue will you lose spending years building? What market share will competitors capture while you're distracted? These costs rarely appear in spreadsheets but are often the most expensive part of the build decision. The Who Not How philosophy becomes an acquisition playbook. When something needs to be done, don't ask how you can learn it yourself. Find someone already better at it and acquire them. Marty applied this when a bookkeeping firm asked for growth help. Instead of consulting fees, he negotiated equity, brought marketing expertise and clients, they tripled revenue, and everyone won when they sold. Profit maximization beats tax mitigation. Every dollar of EBITDA sacrificed to save taxes saves twenty cents but costs seven dollars on a multiple when you sell. When Marty shows clients this math, they immediately shift strategies. This insight often represents millions in additional exit value. Begin with the buyer in mind. Westbound Road identifies upfront who will buy your business and why, then builds the business to suit those buyers. Every decision from CRM selection to staffing structure gets evaluated through one lens: how will this impact deal viability at exit? Minor operational choices can kill deals worth millions. A client built operations entirely on offshore VAs with impressive margins, but many buyers walked away. To command their target multiple, they needed to onshore roles and add W-2 employees. Another business chose a non-standard CRM. An acquirer walked away because integrating it created too much friction. That preference cost millions. The SaaS valuation bubble is being accepted as an anomaly. In 2021-2022, founders got $50 million offers for businesses worth $12 million today. Many refused, expecting the market to stay hot. Marty shows them the charts: the market returned to historical norms, and eighteen months was a bubble. Those founders are finally accepting realistic valuations. Authority marketing creates pre-sold clients. When prospects ask questions, Marty's team sends time-coded podcast links. Prospects listen to full episodes, then more episodes, and arrive ready to sign without sales calls. His first ChatGPT client found Westbound Road via AI recommendation, watched three episodes, and asked where to sign. A business fully prepared to sell is the best business to own. The best practices for creating enterprise value that commands premium multiples are the same practices that make a business pleasurable to operate. Clean financials, reduced owner dependency, autonomous systems, and strategic structure benefit owners whether they sell or not. Perfect for business owners in the $5-50 million range planning exits, entrepreneurs considering M&A advisory relationships, and anyone interested in combining marketing expertise with deal-making to build and sell businesses. FOR MORE ON THIS EPISODE: https://www.coreykupfer.com/blog/martyfahncke FOR MORE ON MARTY FAHNCKE: Website: https://westboundroad.com LinkedIn: https://www.linkedin.com/in/martyfahncke/ FOR MORE ON COREY KUPFER https://www.linkedin.com/in/coreykupfer/ https://www.coreykupfer.com/ 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. Episode Highlights with Timestamps[00:06:48] - Introduction: Marty Fahncke's credentials and experience [00:08:38] - Childhood dream of being a forest ranger in the mountains of Utah [00:11:12] - Early entrepreneurial ventures: bike rehab business at age twelve [00:11:30] - First major deal: grassroots soccer product to QVC and $1.5 million exit[00:23:36] - Eliminating competition through collaboration instead of competing [00:23:36] - Who Not How philosophy applied to M&A and acquisition strategy [00:24:09] - Build versus buy analysis and unreasonable optimism trap [00:28:52] - Combining marketing expertise with M&A strategy as unique advantage [00:31:08] - Starting Westbound Road advisory firm during 2020 disruption [00:33:37] - Focus areas: $5-50M digital businesses, e-commerce, and SaaS [00:34:09] - Exit planning gap: helping founders understand what they have [00:47:13] - Beginning with the end in mind: identifying buyers before building [00:48:01] - Offshore VA staffing structure as deal-killer example [00:48:30] - Non-standard CRM selection costing millions in lost deal value  [00:50:36] - A business fully prepared to sell is the best business to own [00:53:23] - Freedom defined: making impact on entrepreneurs and participating in exits[00:57:32] - Authority marketing: podcast content creating pre-sold clients [01:01:00] - First ChatGPT-originated client story Guest Bio:Marty Fahncke, CMAA is a seasoned marketer and dealmaker with over 35 years of business experience and over 25 years in M&A. He has helped hundreds of businesses scale to over $1 billion in combined revenue and executed nearly $500 million in M&A deals. His first deal was selling a grassroots soccer product business for $1.5 million. His second deal combined a $2 million company with a $1.5 million company and built it to $30 million in revenue in two years. Since then, he has been involved in deals from $5 million to $600 million. He is the founder of Westbound Road, an M&A advisory firm specializing in digital businesses between $5 and $50

    44 min
  3. Episode 394: Navigating Multiple Exits Across Tech's Evolution with Raj Singh

    MAR 11

    Episode 394: Navigating Multiple Exits Across Tech's Evolution with Raj Singh

    From installing network cards as a teenager to navigating four successful exits across decades of tech evolution, Raj Singh shares lessons on acquisition timing, building buyer relationships, and the emotional journey founders experience after selling. Raj Singh is VP of Product at Mozilla, leading new zero-to-one product initiatives. He joined Mozilla in 2022 via acquisition of his startup Pulse (AI meeting summarization). Previously, he co-founded Tempo AI (acquired by Salesforce 2015), All the Cooks (acquired by CookPad), and served as VP of Business Development at Skyfire (acquired by Opera). WHAT YOU'LL LEARN You'll discover why exit windows matter more than plans, how to build relationships with potential acquirers years in advance, the four emotional stages after selling, why 80-85% of acquisitions are CEO-driven, and how founder fatigue is the number two reason startups fail. RAJ'S JOURNEY Raj's entrepreneurial instincts showed up early. Before college, he installed network cards in friends' computers for students heading to dorms. Desktop computers didn't have Ethernet ports back then, so he bought cards from Fry's Electronics, installed them, set up drivers, and charged for the service. His first substantive deal came during the dot-com crash, a net-zero acquisition in the early video codec era around 2000. He's since navigated four exits across radically different market conditions: the dot-com crash, 2008 financial crisis, COVID, and today's landscape. Each taught him something different about timing, negotiation, and integration. "What worked yesterday doesn't work today." THE SERIAL EXIT OPERATOR Raj's perspective comes from exiting companies during each major market cycle, giving him pattern recognition most founders never develop. At Mozilla, he's thrived leading products like Mozilla Solo (AI website builder) and Postful (social media management), finding ways to keep learning within a larger organization. KEY INSIGHTS Exit windows exist and close. Miss one, and the next might not emerge for 3-8 years. Founder fatigue is the number two reason startups fail. The hardest question: can you push through for another five years? Build acquisition relationships years in advance. Identify your 10 most likely buyers on day one. Check in every six months with no intent to sell. Acquisitions are about timing. If your timing doesn't align with a buyer's executive off-site decision, you could be off by six months and it won't happen. The emotional journey: relief when the deal closes, regret within days, inspired to make it the best acquisition ever, then acceptance it's not your company anymore. FOR MORE ON THIS EPISODE https://www.coreykupfer.com/blog/rajsingh FOR MORE ON RAJ SINGH LinkedIn: https://www.linkedin.com/in/rajansingh/ Email: raj@rajansingh.com Twitter/X: @rajansingh Threads: @rajansingh 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:[00:06:37] - Introduction: Raj Singh's bio and background [00:08:28] - Childhood computer interest and early entrepreneurial instincts [00:08:54] - First side hustle: Installing network cards for college students [00:12:07] - First substantive deal during dot-com crash [00:13:30] - Evolution of startup ecosystem: from Chamber of Commerce books to today [00:21:24] - Journey to Mozilla via Pulse acquisition [00:24:03] - Why staying at Mozilla works: continuous learning and challenge [00:32:10] - All the Cooks exit during Y Combinator three-day decision window [00:35:53] - Tempo AI monetization struggles and Salesforce acquisition [00:39:23] - Four emotional stages after acquisition: relief, regret, inspired, acceptance [00:43:07] - Exit windows and why timing matters more than plans [00:43:32] - Founder fatigue as number two reason startups fail [00:48:19] - Building relationships with 10 potential acquirers from day one [00:50:42] - When incumbents enter your category (market acceleration) [00:51:05] - Enterprise multiple winners versus consumer winner-take-all [00:51:31] - Current work at Mozilla: Solo and Postful products [00:52:53] - What freedom means: choosing where to spend time Guest Bio: Raj Singh is VP of Product at Mozilla, leading zero-to-one product initiatives. He joined via acquisition of Pulse (AI meeting tools) in 2022. Previously: co-founder/CEO Tempo AI (acquired by Salesforce 2015), co-founder All the Cooks (acquired by CookPad), VP Business Development at Skyfire (acquired by Opera). BS in computer engineering from Cal Poly. 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 328 - Richard Manders: Serial Acquisitions and Scaling Through M&A 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 - Equitizing Key Employees and Succession Planning Strategies Social Media: Follow DealQuest Podcast: https://www.linkedin.com/in/coreykupfer/ https://www.coreykupfer.com/ Follow Raj Singh: LinkedIn: https://www.linkedin.com/in/rajansingh/ Twitter/X: @rajansingh Threads: @rajansingh Keywords/Tags:startup exits, M&A timing, acquisition strategy, multiple exits, founder fatigue, exit windows, serial entrepreneur, Salesforce acquisition, Mozilla products, Tempo AI, enterprise versus consumer, building acquisition relationships, CEO-driven acquisitions, emotional journey after exit, strategic buyer relationships, All the Cooks, CookPad acquisition, Pulse acquisition, tech evolution, startup integration, venture capital, exit readiness, founder burnout, M&A strategy, tech acquisitions

    44 min
  4. Episode 393: From Failed Investments to 70+ Startups with Andrew Ackerman

    MAR 4

    Episode 393: From Failed Investments to 70+ Startups with Andrew Ackerman

    From losing his entire $25,000 life savings on his first investment to backing over 70 startups, Andrew Ackerman shares proven strategies for evaluating founders, testing assumptions cheaply, and why the best entrepreneurs see deals where others see nothing. In this episode of the DealQuest Podcast, host Corey Kupfer sits down with Andrew Ackerman, a serial entrepreneur turned early-stage investor and innovation expert. Andrew is currently a strategic advisor and head of Reach Labs at Second Century Ventures, consults on corporate innovation strategies and venture studios, and serves as an adjunct professor of entrepreneurship. He previously served as managing director at DreamIt Adventures, one of the top five accelerator programs in the world. He has invested in over 70 startups and written over 60 published articles for Forbes, Fortune, and other major publications. WHAT YOU'LL LEARN: In this episode, you'll discover why Andrew looks for the instinct to hustle for deals rather than focusing on the idea itself, how accelerators fill the gap between friends and family money and proper VC rounds, and why testing assumptions with a five-dollar pack of index cards can save months of development time. Andrew explains the real difference between SAFE notes and convertible notes, what makes lawyers often terrible startup advisors, and the SeatGeek origin story that proves early testing can turn a failing startup into a billion-dollar company. ANDREW'S JOURNEY: Andrew's path started with both grandfathers as entrepreneurs, one running candy shops and the other creating insurance products. Coming out of University of Chicago in the 90s when startups weren't a thing, he chose consulting before realizing the startup world had caught up. His first venture Bunk One provided internet services for summer camps and exited successfully. His second startup taught harder lessons through founder drama and failure. Angel investing came accidentally through a pharma deal he admits he had no business making, but getting lucky early hooked him. Eventually he joined DreamIt Adventures, running their New York office. KEY INSIGHTS: When evaluating founders, Andrew looks for the instinct to hustle. He shared an example of a founder who rented pencils in fifth grade for a nickel a day. Not sold. Rented. That entrepreneurial DNA shows up early and separates successful founders from everyone else. The SeatGeek story proves early testing works. A startup in his accelerator tested conversion rates early instead of waiting, discovered they were completely off, pivoted in seven weeks, and built a billion-dollar company. Lawyers often make terrible startup advisors because their incentive structure is backwards. Billing by the hour doesn't reward speed, and careers focused on avoiding mistakes rather than making deals happen. Perfect for founders thinking about raising capital, anyone curious about how accelerators work, aspiring angel investors wondering how to evaluate founders, and entrepreneurs who want practical frameworks for testing assumptions. FOR MORE ON THIS EPISODE: https://www.coreykupfer.com/blog/andrewackerman FOR MORE ON ANDREW ACKERMAN:https://www.andrewbackerman.comhttps://www.amazon.com/Entrepreneurs-Odyssey-Approach-Startup-Success/dp/1032883545/ref=tmm_pap_swatch_0http://www.linkedin.com/in/andrewbackermanhttps://x.com/andrewackermanhttps://www.instagram.com/andrewbackerman/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! Guest Bio Andrew Ackerman is a serial entrepreneur turned early-stage investor who has invested in over 70 startups. He heads Reach Labs at Second Century Ventures, previously ran DreamIt Adventures' New York office, and teaches entrepreneurship. He has written over 60 articles for Forbes and Fortune and authored The Entrepreneur's Odyssey, written as a novel because stories stick better than frameworks. Related Episodes Episode 370 - Gerry Hays: Democratizing Venture Capital Through VentureStaking Episode 350 - Tom Dillon: Understanding Business Valuation and Exit Planning Realities Episode 89 - Sherisse Hawkins: Capital Raising Journey and Funding Realities Keywords/Tags angel investing, accelerator programs, startup evaluation, founder assessment, SAFE notes, convertible notes, early stage investing, venture capital, startup testing, lean startup, DreamIt Adventures, Second Century Ventures, startup validation, startup pivots, SeatGeek

    48 min
  5. Episode 392: How to Actually Get Your Deals Across the Finish Line with Corey Kupfer

    FEB 25

    Episode 392: How to Actually Get Your Deals Across the Finish Line with Corey Kupfer

    After 35+ years of closing deals across industries, Corey Kupfer shares the practical strategies that separate deals that close from deals that die in the final stretch. This remastered solocast from the early days of DealQuest delivers timeless advice on getting deals across the finish line. In this solocast episode of the DealQuest Podcast, host Corey Kupfer breaks down the critical factors that determine whether your deal actually closes or falls apart at the last minute. Drawing from decades of experience as an M&A attorney, entrepreneur, and dealmaker, Corey addresses the mental traps, preparation gaps, and emotional triggers that derail otherwise successful transactions. WHAT YOU'LL LEARN: In this episode, you'll discover why mentally closing a deal before it actually closes is the biggest mistake dealmakers make, and how "spending the money in your mind" sabotages your focus and negotiating position. Corey explains the concept of pre-due diligence and why preparation before the LOI stage prevents deals from falling apart during buyer scrutiny. You'll learn how to identify your true bottom line and get total clarity on what's acceptable and what's not. The episode covers how ego and emotional attachment blow deals that would otherwise succeed, the strategic balance of bringing in key stakeholders while maintaining confidentiality, and how to keep deal momentum alive through consistent engagement with your professional team. WHY DEALS DIE: Most deals don't fall apart because of bad terms or major due diligence discoveries. They fall apart because someone mentally checked out too early. The moment you sign the LOI and start treating the deal as done, you stop focusing on the critical work still required. You stop keeping your due diligence clean. You stop maintaining pace. You stop staying hungry for the close. The other side senses this shift, issues arise that could have been managed, and momentum dies. PRE-DUE DILIGENCE PREPARATION: One of the best ways to ensure deals close is preparation that happens before negotiations even heat up. If you're selling your company, experienced advisors know what buyers will examine. If you're raising capital, they know what investors will scrutinize. The goal is to be fully prepared and looking great before their team starts asking questions. Many deals fall apart during due diligence because sellers haven't done this preparation work. When there's smoke, buyers think there's fire. One issue makes them worry about ten others they haven't found yet. TRUE BOTTOM LINE CLARITY: This connects to a fundamental negotiating principle from Corey's Authentic Negotiating book. You need total clarity on exactly what's acceptable and what's not acceptable to you. When things shift unexpectedly, whether the economy changes, due diligence reveals issues, a key employee leaves, or you lose a major client, that foundation of clarity determines whether you navigate the disruption or let it derail everything. If you don't know your true bottom line, these disruptions can easily prevent you from ever reaching closing. MANAGING EGO AND ATTACHMENT: As deals progress, watch for ego and emotional attachment on both sides. When the other party raises issues close to closing, you need clarity to analyze whether those issues actually matter versus reacting because you feel triggered. Sometimes people blow deals not because the terms became unacceptable, but because they got tired, frustrated, or insulted. Don't let triggering emotions destroy a deal that could be very good or lucrative for you. STAKEHOLDER ALIGNMENT: Deals can fail at the last minute because the principals assume alignment that doesn't exist. They go to key employees, minority owners, or investors expecting buy-in and discover it isn't there. The balance between confidentiality and getting necessary stakeholder alignment requires strategic thinking. Especially if you're selling your company, you have to weigh not being seen as "in play" on the marketplace and not having employees get spooked against the risk of bringing key folks in too late. MAINTAINING MOMENTUM: Work closely with your team and professionals to keep the pace of the deal moving forward. Deals die when people lose interest or momentum simply fades. Consistent engagement, timely responses to information requests, and staying available to work through inevitable issues keeps deals on track. Perfect for business owners preparing to sell, executives pursuing acquisitions, entrepreneurs raising capital, and anyone involved in transactions who wants to understand why deals succeed or fail in the final stretch. FOR MORE ON THIS EPISODE: https://www.coreykupfer.com/blog/how-to-close-deals 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 to the remastered episode series and podcast growth [01:30] - Setting up the solocast on how to close deals [02:00] - The biggest mistake: mentally closing deals before they're actually closed [03:15] - Why "spending the money in your mind" sabotages your deal [04:00] - The deal is not closed until it is closed: maintaining focus through closing [04:45] - Pre-due diligence preparation as your secret weapon [05:30] - How preparation upfront prevents deals from falling apart [06:15] - The true bottom line concept from Authentic Negotiating [06:45] - Why clarity on objectives helps navigate unexpected disruptions [07:15] - Watching your ego and attachment as deals progress [08:00] - Recognizing when you're triggered versus making clear-headed decisions [08:45] - Making sure stakeholders are aligned before closing [09:15] - Balancing confidentiality with getting necessary buy-in [09:45] - Maintaining deal momentum through engagement with your team 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 on Exit Planning and Founder Clarity Episode 330 - Pete Mohr on Business Transitions and Stakeholder Alignment Episode 337 - Jonathan Gardner on Cross-Cultural Deals and Due Diligence Episode 324 - Sejal Lakhani-Bhatt on Tech Due Diligence in M&A Episode 332 - John Martinka on Financial Due Diligence Best Practices Follow DealQuest Podcast: LinkedIn: https://www.linkedin.com/in/coreykupfer/ Website: https://www.coreykupfer.com/ Keywords/Tags: how to close deals, deal closing strategies, M&A closing process, due diligence preparation, letter of intent, deal negotiation, business acquisition, deal momentum, stakeholder alignment, pre-due diligence, authentic negotiating, true bottom line, deal mindset, transaction management, merger and acquisition, capital raising, joint ventures, business sale preparation, negotiation strategy, dealmaking

    10 min
  6. Episode 391: How to Maximize Your Company's Sale Value with Greg Waller

    FEB 18

    Episode 391: How to Maximize Your Company's Sale Value with Greg Waller

    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:htt

    41 min
  7. Episode 390: Tax-Smart Exit Planning with David Flores Wilson

    FEB 11

    Episode 390: Tax-Smart Exit Planning with David Flores Wilson

    From Olympic sprinter to trusted advisor helping entrepreneurs save millions in taxes, David Flores Wilson shares proven strategies for QSBS planning, equity compensation design, and preparing business owners for successful exits both financially and personally. In this episode of the DealQuest Podcast, host Corey Kupfer sits down with David Flores Wilson, CFA, CFP, Managing Partner at Sinceres, who advises entrepreneurs and business owners in New York City on personal financial planning from formation to exit and beyond. David is a multiple Investopedia Top 100 Financial Advisor whose guidance has appeared in CNBC, Yahoo Finance, the New York Times, US News and World Report, and Investment News. WHAT YOU'LL LEARN: In this episode, you'll discover how QSBS planning can potentially exclude $10 million to $70 million or more in capital gains from taxes when structured correctly, why LLC to C Corp conversion timing creates dramatic differences in tax outcomes, and how QSBS stacking through non-grantor trusts multiplies exclusions. David shares why equity compensation plans often fail to motivate the specific people they target and what questions to ask before choosing a vehicle. You'll also learn about the personal readiness component of exit planning that determines whether entrepreneurs thrive or struggle after selling their businesses. DAVID'S JOURNEY: David's path to financial planning started with entrepreneurial instincts in an unexpected place. Growing up in Guam, he ran a comic book arbitrage business as a kid, discovering price differences between local stores and mainland mail-order catalogs. His father was a CPA with a home office, and despite wanting nothing to do with accounting, David absorbed financial concepts through osmosis that would later prove invaluable. After college at UC Berkeley, David joined Lehman Brothers and worked through the financial crisis. During that time, colleagues started coming to him with financial planning questions, and he realized helping people with their money was his true passion. He sat on that realization for years before eventually transitioning to financial planning. When Covid hit in 2020, David and his partner Dan Ryan launched Sinceres, and the firm has been growing since. OLYMPICS LESSON: David represented Guam in track and field at the 1996 Atlanta Olympics, competing in the 200 and 400 meters. The experience taught him something crucial about career selection. Unlike running, where pushing harder brings diminishing returns and constant injury risk, financial planning offers the opportunity to improve incrementally every single day. That compounding knowledge approach now drives how he serves clients. KEY INSIGHTS: QSBS planning stands out as potentially the most powerful tax planning tool for qualifying entrepreneurs. C Corps meeting holding period and active business requirements can exclude $10 million in gains, or 10 times basis for older shares, with new legislation increasing that to $15 million. The planning becomes even more powerful with LLC conversions where market value at conversion becomes the QSBS basis. The biggest mistake with equity compensation involves choosing vehicles based on what owners like rather than what motivates specific employees. "Equity" can mean participation in profits, upside potential, a seat at the table, or financial disclosure. Different people value these differently, and the best planning starts with understanding objectives before selecting tools. Exit planning involves three components that David implements from the first meeting with business owners. Getting personally ready addresses what provides purpose after selling. Getting financially ready ensures the numbers work. Getting business ready covers everything from customer concentration to management team development. The recent One Big Beautiful Bill Act has changed QSBS holding periods, SALT deductions, and AMT rules. Business owners should review their planning with advisors rather than assuming previous strategies still apply. Perfect for entrepreneurs considering entity structure decisions, business owners thinking about exit planning, and anyone interested in tax-efficient wealth building strategies. FOR MORE ON THIS EPISODE: https://www.coreykupfer.com/blog/davidfloreswilson FOR MORE ON DAVID FLORES WILSON: https://www.planningtowealth.com https://www.linkedin.com/in/davidfloreswilson/ 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 Flores Wilson's credentials and areas of expertise [02:55] - Growing up in Guam with a comic book arbitrage business and CPA father [07:58] - Representing Guam at the 1996 Atlanta Olympics and career lessons from athletics [09:28] - QSBS fundamentals: Exclusions, holding periods, and qualifying business requirements [10:45] - LLC to C Corp conversions and the basis multiplication strategy [11:40] - QSBS stacking through non-grantor trusts and family gifting [19:40] - Equity compensation design: Why attraction, retention, and incentive vehicles often miss the mark[28:37] - Journey from Lehman Brothers through the financial crisis to launching Sinceres [31:59] - Exit planning framework: Personal, financial, and business readiness [41:27] - Recent tax law changes from the One Big Beautiful Bill Act [44:09] - What freedom means: Making impact through continuous improvement Guest Bio David Flores Wilson, CFA, CFP, is Managing Partner at Sinceres, advising entrepreneurs and business owners in New York City on personal financial planning from formation to exit and beyond. His areas of expertise include qualified small business stock planning, business exit planning, and equity compensation planning. David is a multiple Investopedia Top 100 Financial Advisor whose guidance has appeared in CNBC, Yahoo Finance, the New York Times, US News and World Report, and Investment News. He represented Guam in the 1996 Atlanta Olympic Games and sits on the Board of Directors as treasurer of the Lower East Side Girls Club. David is active in Entrepreneurs Organization, the Estate Planning Council of New York City, Advisors in Philanthropy, and the Exit Planning Institute. 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 325 - Kelly Finnell: Using ESOPs in Ownership Succession Planning Episode 350 - Tom Dillon: Understanding Business Valuation and Exit Planning Realities Episode 328 - Richard Manders: Post-Exit Transitions and What Comes After Selling Your Business 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 David Flores Wilson: Website: https://www.planningtowealth.com Keywords/Tags QSBS planning, qualified small business stock, business exit planning, equity compensation, entrepreneur tax strategy, LLC vs C Corp, financial planning for business owners, exit planning institute, tax-efficient wealth building, business succession planning, capital gains exclusion, non-grantor trusts, C corporation conversion, equity incentive plans, entrepreneur financial advisor

    46 min
  8. Episode 389: From Startup to PE Exit in Three Years with Josh Davis

    FEB 4

    Episode 389: From Startup to PE Exit in Three Years with Josh Davis

    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 suc

    53 min
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Why do some companies grow by leaps and bounds while others only inch forward? Simple. They embrace Deal-Driven Growth in addition to organic growth! DealQuest is where you learn how to strategize, prepare for, find, and complete deals to grow your company faster. Listen in as host Corey Kupfer takes you behind the scenes with some of the world’s most fascinating deal-savvy business leaders. This is the one place where they can share openly the secret to deals they have done (or failed to do) and the issues, opportunities, benefits, pitfalls and lessons learned. Here you learn first-hand all about: Powerful deals that require little capital, mergers, acquisitions, and tuck-ins, Joint ventures, partnerships, and strategic alliances, licensing, raising capital and onboarding key employees, negotiating, structuring, finding, valuing, closing and integrating deals. Don’t be the one at the table who doesn’t grasp the power of Deal-Driven Growth!

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