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. 6d ago

    Episode 411: Think Like a Buyer Not an Owner with David Horwich

    From co-managing the Odwalla IPO at Van Kasper & Company to raising $100 million with Lehman Brothers for a Pacific Northwest workers comp captive when insurance was unavailable at any price, David Horwich shares why thinking like a buyer, understanding the three ways to grow a business, and building optionality matter more than chasing any specific exit. In this episode of the DealQuest Podcast, host Corey Kupfer sits down with David Horwich, the founder of Horwich Strategic Advisors (HSA) in Los Angeles. David spent 13 years at Van Kasper & Company before its 1999 sale, retired from banking in 2010, and spent nearly nine years at GHJ before spinning out his own firm about a year ago. Across his four decade career he has been exposed to somewhere between 5,000 and 5,500 companies. WHAT YOU'LL LEARN: Why running a market check with five investment banking firms and five private equity groups produces a real world valuation, how the three ways to grow apply to almost any company, and why selling new stuff to existing customers is by far the easiest path. David also shares how the workers comp captive he raised $100 million for is still operating today. DAVID'S JOURNEY: After economics at UC San Diego and an MBA at Berkeley, David spent five years at a transportation equipment leasing business in San Francisco. He then joined Bruce Emeluth as the first hire at Van Kasper & Company, where he stayed 13 years and chaired the firm's fairness opinion committee. Van Kasper was sold in 1999 to a bank out of Salt Lake City that Wells Fargo later acquired, making the group the first incarnation of Wells Fargo Securities in the fall of 2000. David left in 2003, retired from banking in 2010, spent nearly nine years at GHJ, and spun out Horwich Strategic Advisors about a year ago. KEY INSIGHTS: Not all revenue is created equal. Repeatable revenue beats one-off revenue. Higher margin beats lower margin. Revenue that requires no working capital beats revenue that ties it up. Most owners street fight for the next million dollars of revenue without asking whether it is good revenue or bad. There are three ways to grow a business and the second is easiest by far. Sell what you have to more customers. Sell new stuff to existing customers. Sell new stuff to new customers. David is emphatic that you should almost never attempt the third. Existing customers have already crossed the Rubicon with you, so every cost is lower. Build optionality before you build an exit plan. Before running any analysis for owners unsure what to do, David sends them to their investment advisor to get their financial goals clear first. Then he outlines every alternative. Keep it. Sell it. Recapitalize it. Gift some but not all. The toolkit is small, but choosing well requires clarity first. Perfect for privately held business owners who want to know what their company is actually worth, entrepreneurs weighing whether to buy or build, and leaders in a transition moment who need optionality before an exit. FOR MORE ON THIS EPISODE: https://www.coreykupfer.com/blog/davidhorwich FOR MORE ON DAVID HORWICH: Website: https://horwichadvisors.com LinkedIn: https://www.linkedin.com/in/david-horwich-9317b56/ 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 [00:00:00] - Introduction and overview  [00:02:42] - Chairman's bag carrier and the waste coal project in Hardin, Montana[00:06:22] - Joining Bruce Emeluth as first hire at Van Kasper & Company [00:11:52] - The Odwalla IPO at $8 a share and the E. coli tragedy [00:24:11] - Exposure to somewhere between 5,000 and 5,500 companies [00:35:26] - The market check and the four questions [00:48:00] - The $100 million workers comp captive with Lehman Brothers[00:50:41] - What freedom means to David Guest Bio David Horwich is the founder of Horwich Strategic Advisors (HSA), a Los Angeles based firm focused on maximizing the value of privately held businesses. He runs market checks that produce real world valuations, builds strategic growth plans, and helps owners think like buyers before any transaction. He has been exposed to somewhere between 5,000 and 5,500 companies across his four decade career. After economics at UC San Diego and an MBA at Berkeley, David spent five years at a transportation equipment leasing business in San Francisco before joining Bruce Emeluth as the first hire at Van Kasper & Company, where he stayed 13 years. Van Kasper was sold in 1999 and became the first incarnation of Wells Fargo Securities in the fall of 2000. David retired from banking in 2010, spent nearly nine years at GHJ, and spun out his own practice about a year ago. 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 330 - Pete Mohr: Building an exit-ready business and understanding what your company is actually worth Episode 332 - John Martinka: Exit with style, grace, and more money Episode 293 - Sunny Vanderbeck: Long horizon value creation and building businesses that deserve to last Episode 350 - Tom Dillon: Capital strategy, alternative funding sources, and when not to take venture money Social Media Follow DealQuest Podcast: LinkedIn: https://www.linkedin.com/in/coreykupfer/ Website: https://www.coreykupfer.com/ Follow David Horwich: Website: https://horwichadvisors.com LinkedIn: https://www.linkedin.com/in/david-horwich-9317b56/  Keywords/Tags investment banking, growth consulting, exit planning, market check, three ways to grow a business, think like a buyer, enterprise value, middle market M&A, Van Kasper & Company, Odwalla IPO, private equity, capital raising, business valuation, optionality, strategic growth planning, buy versus build, workers comp captive, privately held businesses, Los Angeles M&A advisor, deal-driven growth

    Episode 411: Think Like a Buyer Not an Owner with David Horwich

  2. Jul 1

    Episode 410: Building Real Estate Freedom with Jens Nielsen

    From buying his first fourplex in Albuquerque for $117,000 to helping build a portfolio of more than 2,700 apartment units and 100,000 square feet of industrial real estate, Jens Nielsen shares why hiring property management on day one, picking the right investors, and getting visionary owners out of their own way matter more than chasing the next deal. In this episode of the DealQuest Podcast, host Corey Kupfer sits down with Jens Nielsen, a commercial real estate investor, operator, and business coach based in Santa Fe, New Mexico. Jens spent 27 years in IT and telecom before transitioning to full-time real estate investing, raising over $10 million in private capital across more than thirty deals. He now works with entrepreneurs across industries to improve execution, leadership, and scalability. WHAT YOU'LL LEARN: Why hiring property management before closing your first deal can save your sanity, how to spot the wrong investor before money changes hands, and why the visionary owner refusing to let go is the biggest blocker to growth in most companies. Jens also explains his pivot from multifamily to light industrial when rates climbed in 2022 and 2023. JENS' JOURNEY: After 27 years in corporate IT and telecom, his mother's passing at age 52 became the catalyst for Jens to seek freedom and disconnect his time from his income. In 2016 he bought his first commercial deal, a fourplex in Albuquerque, New Mexico for $117,000, and hired property management on day one because he lived four hours away in Colorado. His first syndication followed in 2018 with a 38-unit property and five partners. He and his partners have since built a portfolio of more than 2,700 apartment units and over 100,000 square feet of industrial real estate across multiple states. KEY INSIGHTS: Pay attention to investor temperament before money hits the account. One of Jens's first syndication partners wanted more control than he had and freaked out at every financial report. After six months, Jens bought him out so they could both sleep at night. His lesson is direct. If you have to convince someone to invest, that is not a yes. Do enough deals to let the law of large numbers work for you. One of his properties returned 350 percent. Another lost money entirely. If you put everything into one deal, you are gambling, not investing. The visionary owner not letting go is the biggest growth blocker in most companies. Jens has applied the same operational fix across gyms, property management firms, bakeries, a law firm, and an auto shop. The industries change. The bottleneck does not. Perfect for first-time real estate investors trying to avoid the second-job trap, experienced syndicators thinking through investor selection, and entrepreneurs who have hit a growth ceiling because they cannot get out of their own way. FOR MORE ON THIS EPISODE: https://www.coreykupfer.com/blog/jensnielsen FOR MORE ON JENS NIELSEN: https://www.jensnielsen.us https://www.facebook.com/coachjenshttps://www.linkedin.com/in/jenswnielsen/ 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 [00:00:00] - Introduction and overview [00:03:06] - First fourplex in Albuquerque for $117,000 [00:04:10] - Mother's passing at 52 as the catalyst [00:08:03] - Hiring property management on day one [00:10:37] - The first 38-unit syndication in 2018 [00:15:02] - Buying out a nervous investor partner [00:26:31] - The visionary owner not letting go [00:40:36] - Pivoting into light industrial and flex space [00:44:24] - What freedom means to Jens Guest Bio Jens Nielsen is a commercial real estate investor, operator, and business coach based in Santa Fe, New Mexico. After a 27-year career in IT and telecom, he transitioned to full-time real estate investing and helped build a portfolio of more than 2,700 apartment units and over 100,000 square feet of industrial real estate. He has raised over $10 million in private capital and has firsthand experience navigating acquisitions, operational scaling, investor communications, and market downturns. His focus is on what happens after the deal closes. Originally from rural Denmark, Jens moved to the United States thirty years ago. He bought his first commercial property, a fourplex in Albuquerque, New Mexico, in 2016 and built his portfolio through more than thirty per-deal syndications across multiple states. Today he works with entrepreneurs and operators across industries, including gyms, property management companies, bakeries, a law firm, and an auto shop, helping them improve execution, leadership, and scalability so growth creates freedom instead of chaos. 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 338 - Joel Miller: Real estate investing, rental property wealth, and hard money lendingEpisode 328 - Richard Manders: Free Scale Coaching and helping founders build businesses that scale beyond them Episode 336 - Devan Gonzalez: The visionary and integrator dynamic in growing entrepreneurial companies Episode 350 - Tom Dillon: Capital strategy, alternative funding sources, and when not to take venture money   Keywords/Tags:commercial real estate, real estate syndication, multifamily investing, light industrial real estate, flex space, property management, raising private capital, accredited investor strategy, IT career transition, working on the business, visionary bottleneck, EOS implementation, E-Myth, business coaching, scaling small businesses, Albuquerque real estate, Pennsylvania real estate, owner-operator real estate, real estate fundamentals, entrepreneurial freedom

    Episode 410: Building Real Estate Freedom with Jens Nielsen

  3. Jun 24

    Episode 409: The Due Diligence Layer That Decides Whether a Deal Is Real with Josh Emington

    From a childhood dream of becoming an inventor like Louis Pasteur to leading commercial due diligence for private equity funds like KKR and HIG, Josh Emington shares how his team sizes markets, calls real customers, and spots the growth opportunities other investors miss. In this episode of the DealQuest Podcast, host Corey Kupfer sits down with Josh Emington, a partner at The Martec Group, a boutique strategic consulting and market research firm. Josh leads Martec's value creation team, working with lower middle market and middle market private equity funds including KKR, HIG, Granite, Rotunda Capital, and Everglades Equity. WHAT YOU'LL LEARN How commercial due diligence tests whether a deal's growth story actually holds up, why customer concentration can erase a company overnight, and what a free pre-diligence memo can flag before a client spends real money. Josh also explains why his team still picks up the phone to call a target's real customers, and how AI has compressed Martec's research timelines from seven days to two. JOSH'S JOURNEY Josh's path into research started at a scholastic book sale, where his parents picked up a chemistry kit and a book about Louis Pasteur. He decided he wanted to be an inventor who saved lives the way Pasteur had. His first real deal came as an Eagle Scout, selling popcorn door to door to earn a trip. The professional turning point came on a customer journey project for a top manufacturer of toilet seats. When his team learned that customers had no idea who to call when a seat broke, they recommended putting the brand name on the back. Two years later Josh saw the brand on a hotel toilet seat and, as he told Corey, "just making an impact in a business like that doesn't get any better." Over the past decade Josh has executed hundreds of global research and consulting engagements at Martec, focused on commercial due diligence, M&A funnel support, target identification, and customer due diligence anchored in primary research.   KEY INSIGHTS Commercial due diligence looks at both the risks that could blow up a deal and the opportunities a buyer might be paying for without realizing it. Josh shared a southern Florida example where his team helped a client acquire a lawn care installation business alongside a separate maintenance company, turning one time jobs into recurring revenue. Skipping pre-diligence is a common mistake. At least three times a year, Josh's team will deliver a short, free memo that sometimes recommends an investor not proceed at all because a technology is about to obsolesce or a competitor is far more advanced than the marketing suggests. Customer concentration is the biggest single risk Josh's team flags. As he put it, if 10 customers or even one customer accounts for 70 percent of revenue and that relationship ends, you do not have a company anymore. Corey pushed back from his seller side perspective, arguing buyers should consider structural protections tied to retention rather than discounting valuation outright. About 10 percent of Josh's M&A work happens on the sell side through exit planning. In one engagement, his team interviewed 2,000 rug buyers for an upper middle market online rug company to give a skeptical buyer the confidence that the brand really commanded its prices. AI has also compressed Martec's research timelines from seven days to two, and Josh's team now applies a triple AI lens to every deal, assessing how AI will affect the target's market, its workforce, and its own customers. Perfect for private equity investors, business owners preparing for sale, and dealmakers who want to understand what really gets tested before a deal closes. FOR MORE ON THIS EPISODE: https://www.coreykupfer.com/blog/joshemington FOR MORE ON JOSH EMINGTON: Website: https://martecgroup.com/ LinkedIn: https://www.linkedin.com/in/joshemington/ FOR MORE ON COREY KUPFER https://www.linkedin.com/in/coreykupfer/ https://www.coreykupfer.com/ Episode Highlights with Timestamps [00:00:02] - Introduction and Josh's background at The Martec Group [00:03:21] - The toilet seat project that made Josh fall in love with research [00:09:01] - The southern Florida lawn care deal that turned one time jobs into recurring revenue [00:13:39] - The free pre-diligence memo that can stop a bad deal before it starts [00:16:04] - The last bastion of human value and how customer due diligence really works [00:23:13] - Sizing the prize and spotting customer concentration risk [00:38:46] - How AI has compressed research timelines from seven days to two [00:46:56] - What freedom means to Josh Guest Bio Josh Emington is a partner at The Martec Group, a boutique strategic consulting and market research firm serving private equity funds and Fortune 1000 leaders. Over the past decade he has led hundreds of global research and consulting engagements focused on commercial due diligence, M&A funnel support, target identification, and customer due diligence anchored in primary research. He leads Martec's value creation team, supporting clients from thesis validation through pre-LOI and into post close growth strategy. Publicly known clients include KKR, HIG, Granite, Rotunda Capital, and Everglades Equity. 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 332 - John Martinka. Financial due diligence and why messy financial statements can kill a deal or cost a seller real money on valuation. Episode 324 - Sejal Lakhani-Bhatt. Technical and cybersecurity due diligence, and how a company's IT history follows it into a sale. Episode 351 - Corey Kupfer Solocast. A breakdown of the different types of due diligence that apply across every kind of deal.   Keywords/Tags commercial due diligence, private equity due diligence, customer due diligence, voice of customer research, market sizing, TAM and SAM analysis, customer concentration risk, exit planning, M&A due diligence, value creation, buy side due diligence, sell side due diligence, AI in market research, deal thesis validation, competitive market mapping, business combination strategy, recurring revenue acquisition, pre-LOI diligence, lower middle market private equity, Martec Group

    Episode 409: The Due Diligence Layer That Decides Whether a Deal Is Real with Josh Emington

  4. Jun 17

    Episode 408: The Barbell Effect — What Industry Consolidation Means for Your Business

    From speaking at three major wealth management conferences in a single quarter to mapping out a pattern that's already reshaped accounting and is now creeping into law and the trades, Corey Kupfer breaks down the barbell effect and what business owners should be doing now to avoid getting caught in the middle. WHAT YOU'LL LEARN: In this episode, you'll discover what the barbell effect is and why it shows up across industries once consolidation and outside capital enter the picture, how accounting's shift from the Big Eight to the Big Four foreshadows what may be coming in wealth management, and why most deals positioned as mergers are actually acquisitions in disguise. Corey explains why firms stuck in the middle face higher overhead than small competitors and fewer resources than large ones, and how the same dynamic is showing up in the trades, from roofing to electrical. KEY INSIGHTS: The barbell effect describes what happens as an industry consolidates: large, well funded firms on one end, small boutique firms on the other, and the middle becoming the hardest place to operate, with higher overhead than small competitors and fewer resources than large ones. The accounting industry offers a preview of where wealth management may be headed. Corey points to the shift from the Big Eight to the Big Four, and to firms like Eisner and Amper merging to compete at a higher level, along with Apria's growth through acquisition. In legal, only attorneys can own law firms in most states, but Corey describes private equity entering through a managed services model similar to healthcare, where a non-legal company runs the back office while attorneys retain ownership of the practice. Corey shares a comment from his Entrepreneurs Organization lawyers group, that it is much easier to run a law firm under two million dollars or over ten million dollars in revenue than to be stuck in the middle, connecting this to the crossing the chasm dynamic of investing ahead of payoff. Drawing on NAPFA in Minneapolis, Corey notes many members are choosing not to sell to PE backed aggregators, even leaving value on the table, out of concern for fiduciary alignment, while noting he is relaying their perspective rather than judging it. He also points out most "mergers" are actually acquisitions, cites the 2026 Advisor Growth Strategies Report and DeVoe's data showing fewer buyers chasing more sellers and average seller AUM crossing a billion dollars, and closes by noting the same barbell dynamic in the trades, where consolidators and mom and pop firms both persist while the middle gets squeezed. Perfect for RIA owners weighing independence, succession, or sale, leaders of growing companies assessing their industry's consolidation cycle, and anyone navigating competition in the middle market. FOR MORE ON THIS EPISODE: https://www.coreykupfer.com/blog/barbelleffect 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 [00:00:04] - Introduction: the barbell effect and why Corey is talking about it now [00:04:23] - The NAPFA community conversation on succession and exit options aligned with values [00:08:37] - What the barbell effect is and why the middle becomes the hardest place to compete  [00:12:21] - Why it's easier to run a law firm under two million or over ten million in revenue than to be stuck in the middle  [00:16:14] - NAPFA advisors and the choice to stay independent from PE backed aggregators[00:19:55] - The barbell effect in the trades: roofing, gutters, and electrical consolidation[00:21:55] - Planning for industry evolution instead of being surprised by it 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: Building a firm positioned for acquisition and succession Episode 339 - Solocast 74: Building your G2 and creating optionality for internal successionEpisode 331 - Solocast 72: Reading macro and industry trends without letting personal views distort business decisionsEpisode 327 - Solocast 71: Using authority marketing to build relationships and deal flow   Keywords/Tags barbell effect, industry consolidation, RIA independence, private equity wealth management, mergers and acquisitions, internal succession planning, mergers of equals, middle market squeeze, fiduciary advisors, NAPFA, accounting industry consolidation, legal industry private equity, managed services organization, crossing the chasm, RIA exit planning, trades industry consolidation, deal driven growth, 2026 advisor growth strategies, business positioning strategy, exit strategy planning

    Episode 408: The Barbell Effect — What Industry Consolidation Means for Your Business

  5. Jun 10

    Episode 407: Due Diligence, Tax Strategy, and Deal Structuring with Alex Lopez

    From selling candy in school as a kid in Medellin and getting robbed by his business partner, to riding the South Florida real estate boom and losing everything in the crash before he was twenty, Alex Lopez, CPA built his understanding of deals through lived experience long before he picked up an accounting textbook. Alex runs a CPA firm specializing in CFO services and tax minimization strategy, with over 12 years of experience at global accounting and consulting firms and in corporate America. He works with entrepreneurs in professional services, tech, and real estate, focused on helping them scale from six to seven to eight figures while keeping more of their profits out of the IRS's hands. His years as a financial auditor trained him to assess a business quickly, corroborate what owners claim, and identify which direction a company is actually trending. In this episode he walks through two contrasting deals: one where understanding why a buyer was willing to stretch above market multiples revealed hidden strategic value that let his client hold firm on price, and another where a single off-ratio insurance figure that nobody fully investigated masked a multi-million dollar misrepresentation that killed the deal entirely. He also shares the story of a seller whose insistence on cash over a higher leveraged offer turned out to have nothing to do with preference and everything to do with a pending white collar conviction. On tax planning, Alex is direct: by the time a deal is under letter of intent, several of the most powerful strategies are already gone. He walks through qualified small business stock, which can allow eligible founders to exit with little to zero federal tax on the capital gain from a business sale, but only if the company was structured as a C corporation and the stock held for at least five years. He described a young tech founder who called his firm last year with the deal locked and loaded to close, and paid a seven-figure tax bill because nobody had ever told him this option existed. The conversation also covers how S corporation elections that make sense for self-employment tax purposes can create complications in deals that include rollover equity, why founders who avoided C corp status to preserve early pass-through losses often give up far more in QSBS savings than they ever gained, and how structuring payouts over time can both spread the tax bill across lower-bracket years and give sellers leverage to negotiate a higher total price. For anyone building a business with any intention of eventually selling, this episode makes one thing clear: the time to think about these questions is years before you have a buyer at the table. FOR MORE ON ALEX LOPEZ, CPA: Website: AlexLopezCPA.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: Alex Lopez's background in CFO services and tax minimization [02:54] - First deal: selling candy in school and the partner who stole everything [13:48] - Using ratios and anecdotes to spot market exuberance before it corrects [21:31] - Finding hidden value and why a buyer's motivation is negotiating leverage [28:45] - Why tax planning needs to start before there is a deal on the table [32:13] - Structuring payouts over time to spread the tax bill and negotiate better terms [44:13] - The seller whose insistence on cash pointed to a white collar conviction[49:37] - What freedom means: being oneself and at peace with one's surroundings Guest Bio: Alex Lopez, CPA is passionate about helping business owners scale, increase profits, and minimize taxes. With over 12 years of experience working at global accounting and consulting firms and in corporate America, Alex runs a CPA firm specializing in CFO services and tax minimization strategy. He works primarily with entrepreneurs in professional services, tech, and real estate. Alex grew up in Medellin, Colombia and came to the United States in 1999, getting his real estate license straight out of high school before the 2008 financial crisis redirected him toward accounting. That combination of early deal experience and deep technical expertise informs how he advises clients on both the financial and structural dimensions of their transactions. Related Episodes:Episode 350 - Tom Dillon: Business Valuation and Exit Planning Realities: Understand how valuation works in practice and what drives the gap between what owners expect and what the market will pay.Episode 330 - Pete Mohr: Building Enterprise Value and Exit Readiness: Learn how operational decisions made years before a sale determine what a business is actually worth when it goes to market.Episode 339 - Solocast 74: Equitizing Key Employees and Succession Planning Strategies: Explore how entity structure and equity decisions made early shape your options when it is time to exit.

    Episode 407: Due Diligence, Tax Strategy, and Deal Structuring with Alex Lopez

  6. Jun 3

    Episode 406: How to Franchise a Skilled Trades Business with Jack Clark

    When Jack Clark talks about building 180 Water Franchising, he focuses on one core idea: creating a replicable model in an industry that has never had one. The water well business has always been built around owner-operators — small crews, no national presence, and a retiring workforce with no clear succession path. Jack saw that gap and built the first franchise in the industry to fill it. In this episode of the DealQuest Podcast, Corey Kupfer sits down with Jack Clark, founder and owner of 180 Water Franchising, to discuss what it actually takes to franchise a skilled trades business from the ground up — and why this particular market is uniquely positioned for franchise growth. Jack breaks down the full investment and fee structure for franchisees, from the approximately $250,000 startup cost covering a fully stocked service truck to the 6% gross sales royalty, 2% brand fund, and $45,000 franchise fee. He explains why the first franchisee in each new state gets that fee waived, and why suppliers are set up with 90-day terms to ease early operations. The conversation also covers the internal dynamics of running a franchise network, including Jack's weekly Thursday calls with all franchisees, why the direction of learning inside the network has shifted from franchisor to franchisees, and what he calls the "stupid rule policy" — the principle that if a rule has to exist, the underlying system needs to change. Corey and Jack also discuss the emotional and financial reality of investing ahead of growth, including the bittersweet experience of outgrowing your original banker and building an entirely new team to support the next level of the business. This episode is packed with practical insights for entrepreneurs considering franchising as a growth vehicle, skilled trades business owners wondering whether their operation has a replicable system inside it, and anyone evaluating franchise investment opportunities in industries outside the traditional food and service categories. WHAT YOU'LL LEARN Why the water well industry is structurally positioned for franchise growth right now How Jack identified the moment his business became genuinely franchisable The full investment, fee structure, and territory model for 180 Water franchisees Why most franchisees stop worrying about having enough work within their first thirty days What the "stupid rule policy" means in practice and why it matters for franchisee satisfaction How investing ahead of growth temporarily dips profits — and why that's unavoidable Why being first in an untapped industry is a competitive moat, not a warning sign   THE FIRST FRANCHISE IN THE WATER WELL INDUSTRY Jack confirmed it directly in this conversation: "No one's ever franchised the water well industry. I think a lot of guys have talked about it, but it's one of those things that until you really start to unfold it, you don't really realize how many layers there are to it." 180 Water now operates in five states with ten franchisees and is expanding nationally. When demand outpaced their Texas truck supplier, Jack didn't accept the bottleneck — he started manufacturing his own service trucks under the PumpEx Voice brand, turning a supply constraint into an entirely new business line. FOR MORE ON THIS EPISODE:  https://www.coreykupfer.com/blog/jackclark FOR MORE ON JACK CLARK Company: https://180waterfranchise.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 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 also the creator and host of the DealQuest Podcast. Get deal-ready with the DealQuest Podcast with Corey Kupfer, where entrepreneurs and business leaders share insights, challenges, and success stories around deal-driven growth strategies. The show covers mergers and acquisitions, capital raising, strategic alliances, joint ventures, franchising, and more. Episode Highlights with Timestamps [00:00:00] - Introduction: Jack Clark and 180 Water Franchising  [00:04:08] - Buying a drill rig sophomore year of college and never looking back  [00:09:24] - Running four drill rigs and thirty-five employees — and being miserable  [00:19:45] - Finding the first franchisee through Ranch World Ads  [00:21:25] - Ten franchisees across five states and manufacturing their own trucks  [00:27:37] - Why concerns about getting enough work disappear within the first thirty days[00:29:57] - Staffing ahead of growth and building a whole new team [00:46:45] - The "stupid rule policy" and why Jack would have been a terrible franchisee Guest Bio Jack Clark is the founder and owner of 180 Water Franchising, the first and only water well franchise company in the United States. After scaling the business to four drill rigs and thirty-five employees, he recognized that the pump service side of his operation had a genuinely replicable system — and launched 180 Water Franchising to bring it to the industry. 180 Water Franchising now operates in five states with ten franchisees and is expanding nationally. Jack also founded PumpEx Voice, a manufacturing company producing service trucks for the franchise network. 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. Related Episodes: Episode 333 - Greg Mohr: Franchising as a Path to Financial Freedom and Wealth Building Episode 329 - Cliff Nonnenmacher: How Franchise Brokers Evaluate Systems and Match BuyersEpisode 330 - Pete Mohr: Building Enterprise Value and Exit Readiness in a Service Business Keywords/Tags: water well franchise, 180 Water Franchising, Jack Clark, how to franchise a skilled trades business, franchising a service business, blue collar franchise opportunity, skilled trades franchise, franchise investment, franchise fee structure, water well industry, franchise model for entrepreneurs, franchisee success, service business scaling, first franchise in an industry, PumpEx Voice, franchise system design, franchise territory, home services franchise, trades business growth

    Episode 406: How to Franchise a Skilled Trades Business with Jack Clark

  7. May 27

    Episode 405: Reducing Lifetime Tax Drag for Business Owners with Omar Morillo

    When Omar Morillo talks about wealth management for entrepreneurs, he focuses on one core idea: reducing lifetime tax drag across income, investments, business operations, and eventual liquidity events. The earlier owners start planning, the more options they have. In this episode of the DealQuest Podcast, Corey Kupfer sits down with Omar Morillo, founder of Imperio Wealth Advisors, to discuss what sophisticated pre-exit planning actually looks like for business owners preparing for major liquidity events. Omar breaks down the three levels of tax-aware investing, from simple ETF investing to direct indexing and long-short strategies designed to generate capital loss carryforwards for future gains. He explains why many of the best planning opportunities disappear once an LOI is on the table and why advanced preparation matters. The conversation also explores estate planning, donor advised funds, PPLI structures, and the risks of “flavor-of-the-month” tax strategies that are often oversold to entrepreneurs. Corey and Omar also discuss the emotional side of exits, including why many founders struggle with identity and anxiety after selling the business that defined their lives for years. This episode is packed with practical insights for entrepreneurs thinking about exits, recapitalizations, succession planning, or long-term wealth strategy. WHAT YOU'LL LEARN Why reducing lifetime tax drag requires planning years before an exit The differences between ETF investing, direct indexing, and long-short strategies How carry-forward capital losses may help offset future gains Why estate planning and liquidity planning matter before a sale The risks and realities of structures like PPLI and QSBS Why founders often struggle emotionally after successful exits OMAR'S JOURNEY Omar Morillo originally planned to become an airline pilot before eventually finding his way into wealth management. Today, he is the founder of Imperio Wealth Advisors, where he advises entrepreneurs and families on tax strategy, liquidity planning, investments, and long-term wealth management. He approaches advisory work through what he calls an “agnostic lens,” focusing on the right strategy for the client rather than attachment to any single product or structure. FOR MORE ON THIS EPISODE https://www.coreykupfer.com/blog/omarmorillo FOR MORE ON OMAR MORILLO LinkedIn: https://www.linkedin.com/in/omarmorillo/ Company: https://www.imperiowealthadvisors.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 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 also the creator and host of the DealQuest Podcast. Get deal-ready with the DealQuest Podcast with Corey Kupfer, where entrepreneurs and business leaders share insights, challenges, and success stories around deal-driven growth strategies. The show covers mergers and acquisitions, capital raising, strategic alliances, joint ventures, succession planning, and more. Episode Highlights with Timestamps [00:03:00] - Omar's background and accidental entry into wealth management [00:09:15] - The four layers of lifetime tax drag [00:16:40] - Why pre-exit planning must begin years before an LOI [00:22:10] - The three levels of tax-aware investing [00:30:45] - Direct indexing versus long-short strategies [00:38:20] - PPLI structures and investor control concerns [00:45:50] - The Miami Dolphins estate planning example [00:50:15] - Donor advised funds and charitable planning [01:02:00] - Omar's definition of freedom and legacy Guest Bio Omar Morillo is the founder of Imperio Wealth Advisors, a boutique wealth management firm serving entrepreneurs, business owners, and families navigating liquidity events, tax strategy, investment management, and long-term financial planning. He is a Certified Financial Planner (CFP), Accredited Investment Fiduciary (AIF), and Chartered Financial Consultant (ChFC). Omar specializes in helping clients reduce lifetime tax drag through coordinated strategies involving portfolio management, estate planning, charitable planning, and pre-exit structuring. His clients are typically entrepreneurs and business owners with substantial wealth concentration and upcoming liquidity events. 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.Related Episodes Dave Hersh: Founder Identity and the Emotional Impact of Exits DealQuest Wealth Management Series with RIA Industry Acquirers Tom Dillon: Understanding Business Valuation and Exit Planning Realities Keywords/Tags pre-exit tax planning, wealth management for entrepreneurs, direct indexing, long-short investing, PPLI, private placement life insurance, donor advised funds, estate planning, liquidity event planning, tax-aware investing, founder psychology, business exits, capital gains planning, ILIT, QSBS, entrepreneur wealth strategy

    Episode 405: Reducing Lifetime Tax Drag for Business Owners with Omar Morillo

  8. May 20

    Episode 404: What Makes a True Dealmaker with Sara Mostafa

    From sketching fashion designs as a kid to leading complex M&A and private equity deals, Sara Mostafa shares what separates true dealmaking attorneys from ordinary transactional lawyers, why minority investment deals are like marriages with prenups, and what founders should understand before bringing in growth capital. In this episode of the DealQuest Podcast, host Corey Kupfer sits down with Sara Mostafa, the newest partner at Kupfer. Sara has spent more than two decades representing private companies and entrepreneurs across M&A, financing, private equity, governance, employment, real estate, and outside general counsel matters. Like Corey, she came out of big law and built a relationship-first practice that supports clients from inception through exit. WHAT YOU'LL LEARN: In this episode, Sara explains what separates a true dealmaking attorney from an ordinary transactional lawyer, why minority investment deals require “eyes wide open,” and how experienced attorneys balance legal risk against business upside without over-lawyering. She also discusses why AI-related transactions are dominating parts of the California M&A market, why dental and medical practices are commanding strong multiples, what the 2008 recession taught her about resilience and pivoting, and how long-term client relationships often evolve into serving the next generation of entrepreneurs. GUEST'S JOURNEY: Sara originally wanted to be a fashion designer, inspired by her aunt and her childhood love of sketching clothes. While studying at the University of Pennsylvania, she unexpectedly completed her degree requirements early and took a paralegal role at Drinker Biddle & Reath in Philadelphia, which inspired her to pursue law school. She began her legal career at Cooley in San Diego, working on biotech M&A deals before deciding big law was not the long-term fit she wanted. During the 2008 Great Recession, she pivoted to immigration law and nonprofit work in Hawaii before returning full-time to business transactions. She remains licensed in both California and Hawaii. THE DESIGNER DEALMAKER: Outside of law, Sara continues to pursue creative work. Last year she bought a sewing machine and now spends much of her free time designing and making clothes, including garments she is exhibiting at the San Diego County Fair. Like others at Kupfer, she believes building a successful legal career does not require abandoning personal passions or entrepreneurial pursuits. KEY INSIGHTS: A true dealmaking attorney focuses on helping both sides move forward rather than over-lawyering every issue. Business-mindedness, perspective, and the ability to negotiate practical middle ground matter as much as technical legal skill. Minority investment deals can dramatically change how founders operate. Investors often require approval rights over major decisions and expect a future exit, which means founders need to fully understand both the growth opportunity and the downside risk. Sara believes lawyers must balance risk against opportunity. Businesses cannot grow without taking risks, and experienced attorneys help clients evaluate likelihood and impact rather than simply redlining every possible issue. She also explains that curiosity and adaptability matter more than narrow industry specialization in most transactional work. Over her career, she has represented clients across industries ranging from restaurants and fitness centers to technology, healthcare, entertainment, and construction. Perfect for founders considering outside capital, business owners planning an exit, and entrepreneurs evaluating whether their attorney is truly helping get deals done or simply executing documents. FOR MORE ON THIS EPISODE: https://www.coreykupfer.com/blog/saramostafa FOR MORE ON SARA MOSTAFA:https://www.kupferlaw.com/ https://www.linkedin.com/in/sara-mostafa-02404211/ 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:[00:00:03] Introduction: Sara Mostafa's two decades of transactional experience and her arrival as the newest partner at Kupfer [00:03:28] The sewing machine bought last September and exhibiting garments at the San Diego County Fair [00:08:12] Why transactional work appealed and the value of staying with clients through the full business life cycle [00:17:45] The 2008 Great Recession as the only real slowdown and pivoting to Hawaii [00:23:46] Minority investment deals as marriages with prenups [00:29:41] What separates a real dealmaker from a transactional attorney  [00:38:43] What client trust really means to Sara [00:43:11] The children of exited clients calling her for their own ventures [00:45:28] What freedom means: peace of mind Guest Bio:Sara Mostafa is a partner at Kupfer with over two decades of experience representing private companies and individuals across a wide range of transactional matters. Her practice encompasses contract negotiation, entity formation, corporate governance, mergers and acquisitions, private equity transactions, financing transactions, employment matters, real estate transactions, and outside general counsel services. She has represented companies in technology, wealth management, retail, entertainment, wholesale, construction, restaurants, medical practices, marketing, fitness, and nutrition, among others. 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.Related Episodes:Episode 293 - Sunny Vanderbeck: Building Relationships and Selling With Purpose Episode 350 - Tom Dillon: Understanding Business Valuation and Exit Planning Realities Episode 366 - Jodi Hume: Founder Exits and the Emotional Journey Behind Major DecisionsKeywords/Tags:M&A counsel, transactional attorney, dealmaking attorney, minority investment deals, private equity transactions, outside general counsel, California M&A market, AI valuations, dental practice multiples, medical practice multiples, Kupfer Law partner, big law transition, exit preparation, business life cycle counsel, relationship-driven dealmaking, risk versus upside, over-lawyering, corporate governance, entity formation, capital raising, next generation clients, peace of mind freedom

    Episode 404: What Makes a True Dealmaker with Sara Mostafa
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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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