DealQuest Podcast with Corey Kupfer Podcast Por Corey Kupfer arte de portada

DealQuest Podcast with Corey Kupfer

DealQuest Podcast with Corey Kupfer

De: 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!© 2026 014078 Economía Gestión y Liderazgo Liderazgo Política y Gobierno
Episodios
  • Episode 393: From Failed Investments to 70+ Startups with Andrew Ackerman

    Episode 393: From Failed Investments to 70+ Startups with Andrew Ackerman
    Mar 4 2026
    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, ...
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    48 m
  • Episode 392: How to Actually Get Your Deals Across the Finish Line with Corey Kupfer

    Episode 392: How to Actually Get Your Deals Across the Finish Line with Corey Kupfer
    Feb 25 2026
    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, ...
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    10 m
  • Episode 391: How to Maximize Your Company's Sale Value with Greg Waller

    Episode 391: How to Maximize Your Company's Sale Value with Greg Waller
    Feb 18 2026
    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 ...
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    41 m
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