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

    2D AGO

    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
  2. 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
  3. 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
  4. 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
  5. 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
  6. Episode 388: Navigate International Deals Successfully with Corey Kupfer

    JAN 28

    Episode 388: Navigate International Deals Successfully with Corey Kupfer

    In this remastered DealQuest solocast, Corey Kupfer shares insights from over 35 years of cross-border deal-making experience. Originally recorded when the podcast was still called Fueling Deals, this episode remains highly relevant for entrepreneurs considering international expansion or partnerships with foreign companies. WHAT YOU'LL LEARN Why international deals offer significant growth opportunities in less saturated markets The critical importance of finding trusted local partners who understand culture, laws, and how business actually gets done in foreign jurisdictions How employment laws, IP protections, and disclosure requirements vary dramatically across countries and why this matters for your deals Cultural considerations that can make or break international transactions, including business card etiquette, relationship building timelines, and signing ceremony customs Why due diligence processes must be adapted for each jurisdiction's available information and verification methods How foreign companies entering your market could become partners, joint venture collaborators, or even buyers rather than competitors CROSS-REFERENCED EPISODES Episode 173 with Wendy Pease covers international deal lessons in depth Episode 337 with Jonathan Gardner discusses cultural integration in M&A transactions Episode 175 with Natasha Miller explores strategic partnerships with competitors ABOUT THIS EPISODE This remastered episode was selected from the DealQuest archives because the advice and frameworks remain timeless. Corey discusses why globalization will continue despite disruptions, how to approach market entry in foreign jurisdictions, and the opportunity to turn potential foreign competitors into strategic partners. CONNECT WITH COREY LinkedIn: linkedin.com/in/coreykupfer Website: coreykupfer.com ABOUT COREY KUPFER Corey Kupfer is an expert strategist, negotiator, and dealmaker with more than 35 years of professional deal-making and negotiating experience. He is a successful entrepreneur, attorney, consultant, author, and professional speaker who is deeply passionate about deal-driven growth. Corey is the creator and host of the DealQuest Podcast.

    22 min
  7. Episode 387: Mastering Debt Decisions and Alternative Investments with Stas Sukhinin

    JAN 21

    Episode 387: Mastering Debt Decisions and Alternative Investments with Stas Sukhinin

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

    41 min
  8. Episode 386: The $12 Million Lesson Hiding in Your Head with Adi Klevit

    JAN 14

    Episode 386: The $12 Million Lesson Hiding in Your Head with Adi Klevit

    From process consultant to helping businesses increase their enterprise value through systematization, Adi Klevit shares proven strategies for documenting operations, preparing companies for successful exits, and ensuring post-merger integrations don't fall apart. In this episode of the DealQuest Podcast, host Corey Kupfer sits down with Adi Klevit, founder of Business Success Consulting Group, who has spent over 30 years helping entrepreneurs bring order to their operations. Adi hosts the Systems Simplified podcast and contributes articles to Inc.com. WHAT YOU'LL LEARN: In this episode, you'll discover how documented processes dramatically increase enterprise value when selling a business, why buyers light up when they realize they're purchasing a system rather than just a company, and the concept of "unconscious competence" that keeps valuable knowledge trapped in entrepreneurs' heads. Adi shares how to extract hidden systems behind your natural talents, why entrepreneurs resist systematization even though it creates freedom, and how to get teams to actually follow documented processes. You'll also learn how process documentation complements entrepreneurial operating systems like EOS and Scaling Up, what breaks down in post-merger integration when documentation doesn't exist, and why AI is a powerful tool but cannot replace human judgment. ADI'S JOURNEY: Adi started a tutoring business in 9th grade that grew entirely through referrals, teaching her early lessons about balancing promotion with delivery. After working as VP of Marketing at an international consulting company, she launched her own firm when partnership wasn't available. As a general business consultant, she kept telling clients they needed documented processes, and nothing would happen. Finally, she offered to do it for them, and a niche was born. KEY INSIGHTS: A painting company owner documented all their processes with Adi's help. When he went to sell, the buyer's eyes lit up because he realized he wasn't just buying a painting company. He was buying a complete system and operation. On the flip side, Adi recently got a call from someone who bought a company with 60 employees and nothing documented. If everyone quit tomorrow, he would have no idea how to run what he just purchased. EOS implementers are Adi's biggest referral source because operating systems tell you that you need documented processes but don't create them for you. Adi's firm serves as a fractional process team that does the implementation work entrepreneurs keep pushing off. Too many people think deals are done when documents are signed. Adi works with companies that grow through acquisition, helping them bring new employees up to speed on unified systems. Even when both companies have good systems independently, those systems differ. Integration work determines whether the combined entity functions as one or remains two disconnected operations. For Adi, freedom means the ability to create. The systems she builds generate the freedom she values. Perfect for business owners preparing for exits, entrepreneurs struggling to extract knowledge from their heads, and acquirers concerned about post-merger integration. FOR MORE ON THIS EPISODE: https://www.coreykupfer.com/blog/adiklevit FOR MORE ON ADI KLEVIT: https://www.bizsuccesscg.com https://www.linkedin.com/in/adiklevit/ https://www.successreplicator.com  FOR MORE ON COREY KUPFER https://www.linkedin.com/in/coreykupfer/ https://www.coreykupfer.com/ Corey Kupfer is an expert strategist, negotiator, and dealmaker. He has more than 35 years of professional deal-making and negotiating experience. Corey is a successful entrepreneur, attorney, consultant, author, and professional speaker. He is deeply passionate about deal-driven growth. He is also the creator and host of the DealQuest Podcast. Get deal-ready with the DealQuest Podcast with Corey Kupfer, where like-minded entrepreneurs and business leaders converge, share insights and challenges, and success stories. Equip yourself with the tools, resources, and support necessary to navigate the complex yet rewarding world of dealmaking. Dive into the world of deal-driven growth today! Episode Highlights with Timestamps: [00:00] - Introduction: Adi Klevit's journey from childhood entrepreneur to process consultant [09:13] - Starting a tutoring business in 9th grade and learning about business cycles [15:22] - How passion for systematization developed through frustration with clients [18:31] - The painting company story: Buyers purchasing systems, not just businesses [22:04] - Corey's business development system he didn't know he had  [26:37] - Getting teams to actually follow documented processes [34:05] - How process documentation complements EOS and other operating systems  [38:56] - Post-merger integration: Where good deals go to die  [46:26] - Which business areas prove most problematic in integration [51:03] - Why AI cannot replace human judgment in process work [52:56] - Freedom as the ability to create through systems Guest Bio: Adi Klevit is passionate about helping businesses bring order to their operations. With over 30 years of experience as a process consultant, executive, and entrepreneur, she is an expert at making the complex simple. Adi founded Business Success Consulting Group after recognizing that entrepreneurs needed someone to actually do the documentation work they kept putting off. She has been featured on numerous podcasts and delivered many webinars and live workshops sharing her insights on systemizing a business. She hosts the Systems Simplified podcast and publishes a weekly blog, with articles appearing in Inc.com. Known for turning what some see as a dry topic into something fun and practical, Adi shows audiences how to document, implement, and maintain systems that really work. Host Bio: Corey Kupfer is an expert strategist, negotiator, and dealmaker with more than 35 years of professional deal-making and negotiating experience. Corey is a successful entrepreneur, attorney, consultant, author, and professional speaker deeply passionate about deal-driven growth. He is the creator and host of the DealQuest Podcast. Show Description: Do you want your business to grow faster? The DealQuest Podcast with Corey Kupfer reveals how successful entrepreneurs and business leaders use strategic deals to accelerate growth. From large mergers and acquisitions to capital raising, joint ventures, strategic alliances, real estate deals, and more, this show discusses the full spectrum of deal-driven growth strategies. Get the confidence to pursue deals that will help your company scale faster. Related Episodes: Episode 337 - Mastering Post-Merger Integration with Jonathan Gardner: Explore how integration teams need authority and cross-functional participation to succeed after deals close. Episode 330 - From Operator to Owner: Business Freedom with Pete Mohr: Discover why being exit-ready creates freedom whether or not you plan to sell. Episode 341 - Avoid Major Scaling Mistakes with Robert Levin: Learn how sustainable growth strategies prevent the chaos that makes systematization essential. Episode 325 - ESOPs as Exit Strategy with Kelly Finnell: Understand alternative exit structures that preserve company culture and employee relationships. Episode 332 - The Art of Lucrative Exits and Business Growth with John Martinka: Master the fundamentals of preparing businesses for successful exits. Episode 333 - How to Franchise Your Business the Right Way with Greg Mohr: Learn how documented systems enable business replication and growth. Follow DealQuest Podcast: LinkedIn: https://www.linkedin.com/in/coreykupfer/ Website: https://www.coreykupfer.com/ Follow Adi Klevit: LinkedIn: https://www.linkedin.com/in/adiklevit/ Company: https://www.bizsuccesscg.com E-Book: https://www.successreplicator.com Keywords/Tags: business systematization, process documentation, enterprise value, exit preparation, post-merger integration, unconscious competence, scaling businesses, EOS implementation, operational systems, business processes, M&A integration, due diligence, business valuation, entrepreneur freedom, knowledge transfer, team training, business operations, deal readiness, exit strategy, business consulting

    42 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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