Episode 416: Deal Clichés Worth Questioning with Corey Kupfer
"Give me a price, I'll give you a structure. Give me a structure, I'll give you a price." In this solocast, Corey Kupfer takes that favorite saying of his and uses it to unpack a handful of the deal world's most repeated cliches, testing which ones hold up and which ones only apply in certain situations.
Corey has spent more than 35 years structuring and negotiating deals, and in this episode he draws on that experience to walk through what's really behind a purchase price, a valuation multiple, and a few tax and entity assumptions sellers often take as gospel.
WHAT YOU'LL LEARN:
Corey breaks down what actually makes up a deal structure, from escrow and promissory notes to earnouts and rollover equity, and why "give me a price, I'll give you a structure" is the question that should come before you get excited about a top line number. He also digs into why comparing multiples without knowing what they're calculated on is misleading, when the advice to take cash up front actually applies, and why he pushes back on the idea that most businesses can't be scaled or sold.
KEY INSIGHTS:
A purchase price is never just one number. Escrow holdbacks, contingent payments tied to retention, earnouts tied to growth targets, and rollover equity can all sit inside a single deal, and each one carries different risk and different timing.
Multiples are almost never apples to apples. Most quoted multiples are calculated on adjusted EBITDA, and buyers can adjust that number differently, which means a higher multiple doesn't always mean a higher price.
Take cash up front is better advice for Main Street, owner operator deals than it is for the middle market and up, where professional buyers and PE backed firms have more reputational reasons to pay what they owe.
The S Corp regret Corey heard at an industry event traced back to a missed QSBS election, not to S Corps being universally worse. Entity structure decisions depend on industry, timing, and ownership goals, not blanket rules.
Corey doesn't believe in unscalable businesses, only businesses that haven't found their systems yet. The same logic applies to sellability, most businesses that can't sell today can become sellable with the right changes.
Perfect for entrepreneurs preparing for a sale, raising capital, or negotiating a licensing or royalty deal who want to ask sharper questions before they get anchored on a number.
FOR MORE ON THIS EPISODE:https://www.coreykupfer.com/blog/dealcliches
FOR MORE ON COREY KUPFERhttps://www.linkedin.com/in/coreykupfer/ https://www.coreykupfer.com/
Corey Kupfer is an expert strategist, negotiator, and dealmaker. He has more than 35 years of professional deal-making and negotiating experience. Corey is a successful entrepreneur, attorney, consultant, author, and professional speaker. He is deeply passionate about deal-driven growth. He is also the creator and host of the DealQuest Podcast.
Get deal-ready with the DealQuest Podcast with Corey Kupfer, where like-minded entrepreneurs and business leaders converge, share insights and challenges, and success stories. Equip yourself with the tools, resources, and support necessary to navigate the complex yet rewarding world of dealmaking.
Episode Highlights with Timestamps:01:01 - The famous deal world saying, give me a price, I'll give you a structure, and why it matters 03:45 - What's actually inside a deal structure, escrow, promissory notes, and contingent payments 06:24 - Why comparing multiples without knowing what they're calculated on is misleading 09:08 - When take cash up front is real advice, and when it isn't 13:41 - The S Corp story from an industry event and the QSBS election behind it 16:45 - Why Corey believes every business is potentially scalable and sellable
Related Episodes:Episode 328 with Richard Manders, for a deeper look at multiple arbitrage and how buyers think about valuation multiples. Episode 339 for more on purchase price structures, contingencies, and how retention and earnouts affect what a seller actually collects. Episode 325 with Kelly Finnell, for a related conversation on tax advantaged entity and ownership structures.
Keywords/Tags: deal structure, purchase price negotiation, EBITDA multiple, adjusted EBITDA, earnouts, rollover equity, escrow, QSBS, S Corp versus C Corp, business sellability, business scalability, licensing royalties, M&A negotiation, DealQuest solocast
August 5, 202650 min
Episode 415: Building a Permanent Home for Virginia Businesses with Andrew Dunlap
From a two-for-one lawn-mowing deal he negotiated with his neighbor as a kid to founding a holding company that keeps established Virginia businesses in Virginia, Andrew Dunlap shares his data-driven origin story, a fund built to avoid short-term pressure, and why he believes trust is the only currency that always matters.
Andrew is the founder and CEO of Harbor, a long-term, buy-and-hold company that acquires established Virginia businesses and keeps their teams, leadership, and jobs rooted in the state. In roughly two years he has completed three deals, including a CNC machine shop and a FINRA-registered broker dealer, with an industrial services company moving toward close. He describes himself as someone who stumbled backward into this work by digging into merger and acquisition data.
WHAT YOU'LL LEARN:
You will learn why keeping a company's headquarters local changes how much of its revenue recirculates in the community, how an untimed fund with no AUM fees removes the pressure to make what Andrew calls caffeinated decisions, how Harbor structures flexible deals to become the buyer owners actually prefer, the earnout test that separates a real growth forecast from a wishful one, and why Andrew treats trust as the most durable asset in any market.
ANDREW'S JOURNEY:
Andrew grew up in Baltimore and moved to Roanoke, in Virginia's southwest, ten years ago. Coming out of a venture-backed startup in Richmond in January of 2024, he noticed how few senior roles existed in his region, then pulled the merger and acquisition databases to find out why. He discovered that 87 percent of external buyers in Roanoke, and 82 percent across Virginia, were from out of state, which meant companies and their leadership kept leaving. The research he found showed that a locally headquartered company recirculates roughly 52 to 53 cents of every revenue dollar in its community, a figure that falls to about 14 cents once the headquarters moves to a larger city. That gap became the foundation for Harbor.
TRUST AS THE ONLY CURRENCY:
Andrew closed the conversation on a theme he keeps returning to. Trust, he argued, is the one thing that holds when assets turn and revenue streams dry up, and he sees it as underdeveloped in a digital, globalized world where people invest too little in relationships.
KEY INSIGHTS:
Andrew's foundational insight is that owners care deeply about who becomes the next steward of what they built. He lays out three options for a seller, a strategic buyer, a private equity firm, or a buyer like Harbor that keeps the team in the town where it grew up, and owners consistently choose the path that protects the legacy. Harbor backs that up with flexible structures, using earnouts, seller financing, and varying equity so the deal fits the owner.
His most timely insight is that trust outlasts any single asset or revenue stream. When tungsten prices spiked because of China and hit his machine shop, Harbor could call a congressman who came to walk the shop floor. Andrew credits relationships, built in part through writing openly on LinkedIn, for access that does not show up on a balance sheet.
Perfect for owners weighing succession, investors interested in longer-hold alternatives to private equity, and anyone curious about how local ownership shapes a regional economy.
FOR MORE ON THIS EPISODE: https://www.coreykupfer.com/blog/andrewdunlap
FOR MORE ON ANDREW DUNLAP:https://harbor.capital https://www.linkedin.com/in/dunlapandrew/
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 of Harbor [00:01:48] - Andrew's first deal, a two-for-one lawn-mowing bulk rate [00:02:42] - How he stumbled backward into building Harbor [00:05:05] - The recirculation research, 52 to 53 cents local versus 14 cents once a headquarters leaves [00:13:25] - The untimed fund and avoiding caffeinated decisions [00:21:00] - The Clark Precision Machine acquisition and the owner's five-year contract[00:34:54] - The red flags that kill a deal and the earnout bluff test [00:45:32] - Why trust is the only currency that always matters [00:49:40] - The freedom question
Guest Bio
Andrew Dunlap is the founder and CEO of Harbor, a holding company that buys established Virginia businesses to keep them in the state. He grew up in Baltimore, moved to Roanoke a decade ago, and came into acquisitions after coming out of a venture-backed startup in Richmond in early 2024, where he had helped build a software company with users in 60 countries. Harbor's leadership also includes M&A and securities attorney Tad Fisher and operations leader Krista Glassburn, who previously ran a manufacturing company in Tazewell, Virginia and grew it from 15 to 190 million dollars while acquiring seven companies. In its first two years, Harbor has acquired a CNC machine shop, a FINRA-registered broker dealer, and moved toward closing on an industrial services company.
Show Description
Do you want your business to grow faster? The DealQuest Podcast with Corey Kupfer reveals how successful entrepreneurs and business leaders use strategic deals to accelerate growth. From large mergers and acquisitions to capital raising, joint ventures, strategic alliances, real estate deals, and more, this show discusses the full spectrum of deal-driven growth strategies. Get the confidence to pursue deals that will help your company scale faster.
Related Episodes
Episode 328 - Richard Manders: How private equity roll-ups create value versus simply aggregating for a multiple arbitrage exit Episode 325 - Kelly Finnell: Using an ESOP as an exit that can preserve a company's independence and reward its people Episode 332 - John Martinka: Buying a business and transitioning from a corporate career into acquisition entrepreneurship
Keywords/Tags
Andrew Dunlap, Harbor, buy and hold holding company, keeping businesses local, Virginia acquisitions, mergers and acquisitions, business succession planning, alternative to private equity, earnouts, seller financing, deal structure, CNC machine shop, FINRA broker dealer, metal fabrication, economic recirculation, DealQuest Podcast, Corey Kupfer
July 29, 202651 min
Episode 414: From China to SparkVox with Sean Weisbrot
From learning Mandarin with nothing but a notebook and a pen on the streets of Wuhan to losing $650,000 of his own money before ever raising outside capital, Sean Weisbrot shares hard-won lessons on cross-cultural dealmaking, bootstrapping versus fundraising, and why LinkedIn visibility now matters for founders and their teams.
Sean is the founder of SparkVox, a tool that turns content executive teams are already creating into LinkedIn posts in their own voice, and the host of We Live to Build, a podcast with roughly 235,000 subscribers and more than 320 interviews with seven and eight figure brand owners. He has helped create over $100 million in value across his network and generated more than $15 million in revenue for his own businesses, all while living in China, Vietnam, and now Portugal.
WHAT YOU'LL LEARN:
You'll discover how a single misstep with a business card or a signing pen can cost a deal before it starts, why 320 founder interviews convinced Sean that bootstrapped founders tend to be happier than funded ones, and how a $400,000 gap between what one investor promised and delivered helped sink his last company. Sean also explains how he now runs a business on roughly $50 a month using AI, and why he believes every founder and executive needs a visible presence on LinkedIn.
SEAN'S JOURNEY:
Sean had no entrepreneurial role model growing up. What moved him was a pull to leave the US, and after missing a deadline for a teaching program in Japan, he landed in China instead and stayed for ten years, learning Mandarin street vendor by street vendor with a notebook and a pen. His first real deal came in 2016, connecting an American founder with a Chinese investor for a $150,000 raise and earning a $7,500 commission.
From there he built a $15 million consulting business helping Chinese and Western companies raise money from each other in the blockchain space. His next venture, a tech company built to compete with Slack, taught him a harder lesson. He put in $650,000 of his own money before raising a $1 million seed round, and a $400,000 shortfall from one investor became a major factor in the company's failure. COVID and a divorce followed, which is part of what led him to Portugal for a fresh start.
KEY INSIGHTS:
Deal culture varies sharply across countries, down to details like how a business card is received. Corey shared a parallel story about a 1980s deal that nearly stalled at signing over missing ceremonial pens.
Founder happiness tracks closely with how a company was funded. Across 320-plus interviews, Sean found bootstrapped founders were generally happier than those who raised capital.
A funding gap can sink a company as fast as a bad decision can, as Sean's own $400,000 shortfall proved.
AI has collapsed the cost of running a business. Sean's infrastructure now costs about $50 a month, down from roughly $1,000 a month at his last company.
Visibility has become a gatekeeper for access, with investors now expecting founders to be active on LinkedIn before they'll even take a call.
Perfect for founders weighing whether to bootstrap or raise capital, business leaders working across cultures on deals, and anyone trying to build an authentic presence on LinkedIn.
FOR MORE ON THIS EPISODE: https://www.coreykupfer.com/blog/seanweisbrot
FOR MORE ON SEAN WEISBROT: https://www.welivetobuild.com/ https://www.linkedin.com/in/seanweisbrot/
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 Sean's background [00:04:20] - Sean's first professional deal in China [00:09:13] - Cultural differences in dealmaking between the US and China[00:26:22] - The capital raising journey behind his last tech company[00:41:03] - What SparkVox does and who it serves [00:53:23] - What freedom means to Sean
Guest Bio:Sean Weisbrot is the founder of SparkVox, which turns content executive teams are already creating, sales calls, internal trainings, podcast appearances, into LinkedIn posts in their own voice. He is also the host of We Live to Build, a podcast with roughly 235,000 subscribers and more than 320 interviews with seven and eight figure brand owners. Sean has helped create over $100 million in value across his network, generated more than $15 million in revenue for his own businesses, and raised over $8 million for his businesses and clients. He has angel invested in nine companies with two exits. Fluent in Mandarin, he lived in China for ten years and Vietnam for five before settling in Portugal, where he now lives with his family.
Related Episodes: Episode 337 - Jonathan Gardner: Cultural due diligence and what gets lost in translation across German, Japanese, and Chinese deals Episode 370 - Gerry Hays: Democratizing venture capital and when founders should raise versus bootstrap Episode 350 - Tom Dillon: When NOT to take venture capital money and alternative funding sources
Keywords/Tags: Cross-cultural dealmaking, bootstrapping versus venture capital, LinkedIn content strategy, AI-powered content creation, blockchain fundraising, founder visibility, personal branding, remote entrepreneurship, cultural due diligence, capital raising
July 22, 202643 min
Episode 413: Mastering the People Side of Deal-Driven Growth with Victoria Pelletier
From buying the casting agency that represented her as a teenage actor at age twenty to being involved in more than forty M&A transactions, Victoria Pelletier shares why joint ventures run their course, what six acquisitions in eighteen months taught her about integration, and why 70 percent of deal value comes down to people and process.
Victoria is a keynote speaker, published author, board director, and transformational executive with more than twenty years of leadership experience at major companies such as IBM and American Express. Her self-described nickname is the turtle, tough on the outside, a marshmallow on the inside.
WHAT YOU'LL LEARN:
You'll discover why joint ventures can end without anything going wrong, how patient trust-building saved a 250 million dollar client portfolio during an acquisition streak, why only 10 percent of AI value comes from the algorithms while 70 percent comes from people and process, and why no company Victoria has seen has truly moved past proof of concept to enterprise-level AI.
VICTORIA'S JOURNEY:
Victoria bought her first company at age twenty, paying around ten thousand dollars for the casting agency that represented her and selling it about eighteen months later. She went on to a publicly traded corporate travel company that ended a joint venture, went public, and acquired six companies in eighteen months, with Victoria involved from due diligence through integration. She has since built and sold a natural bath and body company, published four books with a fifth arriving later this year, and now focuses on speaking, AI advisory work, and executive coaching.
KEY INSIGHTS:
People drive most of the value in any deal. Victoria cites a BCG finding that only 10 percent of AI value comes from the algorithms, 20 percent from data and technology, and 70 percent from people and process, a ratio she sees play out in deals everywhere. During her acquisition streak, she spent almost a year winning the trust of a woman thirty years her senior who ran a 250 million dollar client portfolio rather than restructuring her out, and that woman became one of her biggest cheerleaders.
Due diligence is where deals most often go wrong, a lesson Victoria learned firsthand when a seller misrepresented a business and she had to sue. And someone must own the value after closing, which is why she built a value realization office at her last company. Her philosophy through it all comes down to choice. "I do not do things personally or professionally that don't bring me joy or value."
Perfect for business owners considering their first acquisition, leaders navigating post-deal integration, and anyone interested in the people side of deal-driven growth.
FOR MORE ON THIS EPISODE: https://www.coreykupfer.com/blog/victoriapelletier
FOR MORE ON VICTORIA PELLETIER:www.victoria-pelletier.comhttps://youtu.be/xFpknOCFMOg
FOR MORE ON COREY KUPFERhttps://www.linkedin.com/in/coreykupfer/ https://www.coreykupfer.com/
Corey Kupfer is an expert strategist, negotiator, and dealmaker. He has more than 35 years of professional deal-making and negotiating experience. Corey is a successful entrepreneur, attorney, consultant, author, and professional speaker. He is deeply passionate about deal-driven growth. He is also the creator and host of the DealQuest Podcast.
Get deal-ready with the DealQuest Podcast with Corey Kupfer, where like-minded entrepreneurs and business leaders converge, share insights and challenges, and success stories. Equip yourself with the tools, resources, and support necessary to navigate the complex yet rewarding world of dealmaking. Dive into the world of deal-driven growth today!
Episode Highlights with Timestamps[00:00:00] - Introduction and overview [00:02:26] - Buying the casting agency that represented her at age twenty[00:12:07] - The 250 million dollar client portfolio she almost restructured[00:21:29] - The acquisition that went poorly and ended in a lawsuit [00:39:50] - Why no one is doing AI at enterprise scale yet [00:43:08] - What freedom means to Victoria
Guest BioVictoria Pelletier is a keynote speaker, published author, board director, and transformational executive with more than twenty years of leadership experience, including roles at major companies such as IBM and American Express. She has been involved in more than forty M&A transactions along with joint ventures and her own acquisitions and exits. Known for her no excuses philosophy, she helps organizations and professionals develop stronger leadership skills, build personal brands, embrace diversity and inclusion, and create lasting professional success. Her fourth book came out earlier this year and her fifth arrives later this year, covering personal branding, leadership, culture, and career transitions.
Related EpisodesEpisode 293 - Sunny Vanderbeck: Long horizon value creation and building businesses that deserve to last Episode 330 - Pete Mohr: Building an exit-ready business and understanding what your company is actually worth Episode 366 - Jodi Hume: Founder decision-making and the emotional journey behind major business decisions
Keywords/TagsM&A integration, joint ventures, due diligence, post-merger integration, people and process, value realization office, corporate travel company acquisitions, personal branding, leadership, no excuses philosophy, women in leadership, executive coaching, AI adoption, enterprise AI, transformational executive, deal-driven growth
July 15, 202636 min
Episode 412: The DealQuest Quarterly Roundtable With Brian Meegan And Sara Mostafa
After more than 400 episodes across eight years, Corey Kupfer launches a new quarterly roundtable with his law firm partners Brian Meegan and Sara Mostafa (together representing roughly 90 years of combined deal experience) to unpack why the projected 2026 M&A boom has not fully arrived, revisit the negotiation tactics behind the 1951 Korean War armistice, and share parting wisdom for business owners in a slower market.
In this episode of the DealQuest Podcast, host Corey Kupfer launches a new quarterly roundtable format with his law firm partners, Brian Meegan and Sara Mostafa. Brian has been a partner for several years. Sara joined this year as the newest partner. Together the three represent about 90 years of combined deal experience across M&A, capital raises, cross-border transactions, and wealth management.
WHAT YOU'LL LEARN
You'll discover why the pent-up M&A demand projected for 2026 has not materialized as expected, how a Virginia-focused fund is challenging the assumption that acquisitions drain leadership talent out of state, and why wealth management continues to run counter to the broader slowdown. Brian and Sara explain what a $60 billion all-stock transaction involving AnySphere signals about AI M&A, what the 1951 Korean War armistice negotiations still teach modern dealmakers, and how a post-Soviet Russian deal turned on cultural understanding rather than a legal provision.
THE FIRM'S JOURNEY TO A QUARTERLY ROUNDTABLE
The DealQuest Podcast has run for eight years and passed 400 episodes with a rhythm of three guest interviews followed by a solocast. Brian Meegan joined the firm a few years ago as a partner and has appeared on the show as a guest a couple of times. Sara Mostafa joined this year as the newest partner and has also appeared as a guest since coming on board. With three partners now representing roughly 90 years of combined deal experience, Corey launched this quarterly roundtable to talk deals openly, share what each partner is seeing across their practice areas, and introduce a new Deals in History segment.
DEALS IN HISTORY
Brian opened the first installment of Deals in History with the 1951 Korean War armistice negotiations, which contained nearly every classic tactic anyone has ever written about. The North Koreans picked up the UN delegation in cars carrying white flags, used higher chairs to gain physical advantage, and pushed multi-meeting standoffs over table shape and flag size. At one point both sides sat in complete silence for over two hours, refusing to move on a single boundary point. The full negotiation spanned roughly 160 meetings across two and a half years, and the document that resulted is not a peace treaty. It is a ceasefire that has held since the end of the war.
KEY INSIGHTS
The pent-up 2026 M&A demand has not arrived. Energy price disruption, interest rate uncertainty, and other macro conditions have kept the big bump from showing up. Deal flow remains active, but both Brian and Sara noted a less frenetic pace toward closing.
Wealth management remains a meaningful exception, with private equity capital and succession pressure keeping RIA deal flow robust. Outside wealth management, Sara is seeing active smaller and mid-market activity, especially for targets that have successfully integrated AI into operations.
Andrew Dunlap's Virginia-focused fund is a useful counterweight to the standard acquisition narrative. He shared with Corey that 82 percent of Virginia acquisition buyers were from out of state, and top leadership talent tends to relocate with the new HQ. His commitment is to keep businesses local, in a mini Berkshire Hathaway style approach.
Cultural understanding often matters more than a specific legal provision. Corey shared a story from the early 1990s, just after the Soviet Union fell, when a Russian counterparty refused to sign a standard non-circumvention agreement as a matter of deeply held belief. Corey structured around it by locking up non-circumvention agreements with the US suppliers directly, and closed the deal.
There is a deal for almost any business frustration, challenge, or opportunity. Corey's parting wisdom points to acquihires, joint ventures, strategic alliances, and white labeling as underused options. Brian added Jim Collins' 2009 line to never waste a good recession. Sara closed with practical guidance for women-owned and minority-owned business owners to seek community and specialized funds beyond the SBA.
Perfect for entrepreneurs weighing M&A moves right now, wealth management and RIA professionals tracking deal flow, and anyone interested in how experienced deal lawyers read the market quarter to quarter.
FOR MORE ON THIS EPISODE https://www.coreykupfer.com/blog/quarterly-roundtable-brian-meegan-sara-mostafa
FOR MORE ON KUPFER.https://www.kupferlaw.com
FOR MORE ON COREY KUPFERhttps://www.linkedin.com/in/coreykupfer/ https://www.coreykupfer.com/
Corey Kupfer is an expert strategist, negotiator, and dealmaker. He has more than 35 years of professional deal-making and negotiating experience. Corey is a successful entrepreneur, attorney, consultant, author, and professional speaker. He is deeply passionate about deal-driven growth. He is also the creator and host of the DealQuest Podcast.
Get deal-ready with the DealQuest Podcast with Corey Kupfer, where like-minded entrepreneurs and business leaders converge, share insights and challenges, and success stories. Equip yourself with the tools, resources, and support necessary to navigate the complex yet rewarding world of dealmaking. Dive into the world of deal-driven growth today!
Episode Highlights with Timestamps
[00:00:00] - Launching the new quarterly roundtable format with Brian Meegan and Sara Mostafa[00:05:13] - Sara on smaller and mid-market deal activity, especially where AI is integrated[00:09:18] - Andrew Dunlap's Virginia fund and the 82 percent out-of-state buyer statistic[00:11:24] - Space industry multiples running hot alongside AI [00:14:09] - The $60 billion all-stock transaction involving AnySphere and Cursor[00:15:04] - Deals in History debut, the 1951 Korean War armistice negotiations[00:20:26] - Walking the Abraham Path with William Ury in 2017 [00:23:32] - Corey's post-Soviet Russian deal and the non-circumvention agreement story [00:28:17] - Cross-border capital flow from the Middle East, India, and China [00:36:22] - Parting Shots from Sara, Brian, and Corey
Guest Bios:
Brian Meegan has represented US and multinational clients on corporate matters for more than 25 years, primarily on M&A, business formation, contract negotiation, and real estate. Before joining Kupfer, he founded Evergent Law, listed in Best Law Firms in America (Colorado) for Corporate Law and the exclusive Colorado M&A firm in the IR Global network, and he separately founded Watson Ltd., a back-office support company serving law firms nationwide. Brian earned his B.S. and J.D. from the University of Colorado, is listed in Best Lawyers in America (Colorado), and is a self-described history nerd who powers the new Deals in History segment on the show.
Sara Mostafa is a corporate attorney with nearly two decades of experience representing private companies and individuals across M&A, private equity, financing, corporate governance, employment, real estate, and outside general counsel work, with clients spanning technology, wealth management, retail, entertainment, construction, restaurants, medical practices, and fitness and nutrition. She began her practice at Cooley LLP in San Diego and later served as a Partner at Lobb & Plewe LLP before joining Kupfer. Sara earned her J.D. from UCLA School of Law and her B.A. magna cum laude from the University of Pennsylvania, completed Harvard Law School's Executive Education program in M&A in 2023, and is licensed in California and Hawaii. She speaks English, Spanish, Arabic, and French
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 351 - There's a Deal for That Episode 331 - M&A Market Outlook and Deal Predictions Episode 293 - Sunny Vanderbeck, Selling Without Selling Out
Keywords/Tags:
DealQuest quarterly roundtable, Brian Meegan, Sara Mostafa, Corey Kupfer, 2026 M&A market, wealth management M&A, RIA deal flow, AI acquisitions, AnySphere Cursor, mid-market deals, cross-border transactions, Korean War armistice negotiation, William Ury, post-Soviet dealmaking, Andrew Dunlap Virginia fund, mini Berkshire Hathaway, non-circumvention agreement, deal-driven growth, Kupfer Associates, private equity M&A
July 8, 202644 min
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
July 1, 202641 min
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
June 24, 202649 min
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
June 17, 202622 min
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
June 10, 202644 min
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.
Is this your show?
Claim this listing to keep it up to date, reach guests who want to pitch you, and manage bookings with Guestify.
