DealQuest Podcast with Corey Kupfer

From process consultant to helping businesses increase their enterprise value through systematization, Adi Klevit shares proven strategies for documenting operations, preparing companies for successful exits, and ensuring post-merger integrations don't fall apart. In this episode of the DealQuest Podcast, host Corey Kupfer sits down with Adi Klevit, founder of Business Success Consulting Group, wh...

From a lumpy 2025 market to building pent-up demand, M&A attorneys Corey Kupfer and Brian Meegan share their frontline perspective on deal trends and what business owners need to know heading into 2026. In this episode of the DealQuest Podcast, host Corey Kupfer sits down with his partner Brian Meegan of Kupfer. to kick off the new year with a candid conversation about the deal market. Togethe...

About fifteen years ago, I gave up the conversation around balance entirely. The word I use instead is integration, and in this holiday episode I share why that shift transforms how entrepreneurs experience everything from year-end deal closings to family obligations. In this holiday episode of the DealQuest Podcast, I share reflections on 2025, point to must-listen episodes, preview what's coming...

From closing dinner conversations that changed his career trajectory to advising on transactions up to half a billion dollars, Channing Hamlet shares proven strategies for selling businesses at premium valuations through proper preparation, understanding sector-specific value drivers, and creative deal structures. In this episode of the DealQuest Podcast, host Corey Kupfer sits down with Channing...

From chief marketing officer at the first internet bank to building the leading annuity platform for RIAs, David Lau shares proven strategies for raising capital, navigating public company challenges, and why converting commission-based revenue to fee-based can multiply your exit value by five times. In this episode of the DealQuest Podcast, host Corey Kupfer sits down with David Lau, founder and...

What if losing your life savings on your first investment at age 27 became the catalyst for understanding why 90% of startups get stuck for the same psychological reasons? That's exactly what happened to Dave Hersh, founding CEO of Jive, board partner at Andreessen Horowitz, and author of Reignition. Dave grew Jive from an open-source project to a NASDAQ IPO, bootstrapping to $12 million over five...

From jumping straight to deal structure to building repeatable acquisition programs that scale, Corey Kupfer shares the exact whiteboarding process he uses with clients to create successful deal programs across M&A, joint ventures, licensing, and any deal-driven growth strategy. In this solocast episode of the DealQuest Podcast, host Corey Kupfer walks through the five critical steps that must...

From losing his $25,000 life savings on his first startup investment to democratizing venture capital for everyday investors, Gerry Hays shares proven strategies for making early-stage investing accessible through VentureStaking while teaching founders outside traditional tech hubs how to raise capital and build sustainable businesses. In this episode of the DealQuest Podcast, host Corey Kupfer si...

From professional wakeboarder to CEO managing $250M+ in commercial real estate investments, Nick Jones shares proven strategies for building successful real estate businesses through strategic partnerships, effective capital raising, and protecting investor interests. In this episode of the DealQuest Podcast, host Corey Kupfer sits down with Nick Jones, CEO of Alakai Capital, who has underwritten...

Think making money and making impact are mutually exclusive? THINK AGAIN. Bob Bush went from working on the RJR Nabisco LBO to advising Dubai's government to co-founding a coffee company with NBA legend Dikembe Mutombo. His approach? Commerce, not charity. After 30+ years structuring deals across Wall Street, Africa, and the Middle East, Bob discovered that sustainable social impact requires...

Just wrapped my second year chairing the EO Deal Exchange Conference, and the lessons were off the charts. Here's what happens when you put hundreds of entrepreneurs in a room focused on one thing: growing through deals. Three insights that stood out: The wisdom is already in the room. We ran deal speed networking sessions where members shared their specific needs (buying companies, seeking JV par...

85% of founders have regrets about their exits. The research is clear. But here's what surprised me most about this statistic: almost none of them regret leaving money on the table. They regret the clarity work they didn't do beforehand. In my latest conversation with Jodi Hume, an advisor who works exclusively with founders and CEOs navigating acquisitions and exits, we explored what that clarity...

Concentration beats diversification. One stock. That's all Jaden Sterling bought during the 1990s. It tripled, became capital for 125 real estate deals, and eventually funded Sterling Stock Picker, a stock-picking platform now serving 3,000 investors. What most financial advisors don't tell you: diversification is what you do when you don't know what you're doing. When Jaden's clients at Merrill L...

I just had an incredible conversation with Jon Wells on the DealQuest Podcast about a real estate niche that most investors have never even considered. After 25 years in Denver real estate, Jon discovered something remarkable: group homes for mental health and sobriety programs that generate 6%+ cap rates with almost zero landlord responsibilities. Here's what struck me most from our discussion: J...

Warren Buffett called it one of his biggest investment mistakes. The 2015 Kraft Heinz merger destroyed $63 billion in shareholder value while the broader market doubled. Key lessons for M&A professionals: • Consumer behavior trend analysis is critical for food industry due diligence • Aggressive cost reduction can eliminate innovation capacity in consumer products • Post-merger integration str...

Think great communication in deals is about having the right words or perfect hand gestures? After 35 years of negotiating deals, I can tell you this: all the tactical training in the world won't help if you haven't done the internal work to understand who you are and what you bring to the table. In this episode, Dia Bondi breaks down why your leadership voice matters more than any communication s...

"Every time I get off the phone with you, I feel better... but I don't call because I don't want to pay the billable hour." Alexandria Seydel heard this from clients constantly when she was practicing M&A law. So she made a simple offer: "What about once a month you buy me lunch and we go for 90 minutes and you get my brain." Those lunch conversations changed everything. Alexandria realized sh...

Think investors who don't re-up for your next round are doing you a favor? Not the case! Most entrepreneurs see this as rejection. But here's what Sahil Patel discovered after 11 years building and selling ER Express: Sometimes the BEST thing that can happen is getting misaligned investors out of your cap table. His family office investors knew service businesses. But SaaS? Different game entirely...

JP Morgan's latest M&A report reveals something fascinating: despite ongoing uncertainty, global deal volumes hit $2.2 trillion (up 27% year-over-year). Here's what caught my attention: - Mega deals increased 57% because bigger players can thrive when smaller competitors freeze up. - Cross-border activity actually grew 24% despite rising protectionism as companies use M&A to position aroun...

Ever wonder how great dealmakers got their start? Some began with childhood lemonade stands. Others learned through necessity when family circumstances required quick business education. A few discovered their talents through door-to-door sales or car flipping as teenagers. But here's what's fascinating: every successful dealmaker has an origin story that reveals the early development of skills th...

Most people think private equity means gutting companies and squeezing margins. Neal Cobb is proving them wrong. After raising over $20 million and scaling his delivery startup to 100,000 drivers before selling to 7-Eleven, Neal could have retired. Instead, he's building something that challenges everything we think we know about private equity. At Equity X, they're acquiring legacy businesses and...

 Eighty percent of business owners have eighty percent of their net worth locked in their business. But only twenty percent of businesses survive to see their tenth birthday. This conversation will change how you think about building enterprise value forever. Scott Beebe didn't just build a successful consulting practice... He proved that the secret to enterprise value isn't your product, you...

Most business leaders believe they need significant capital to pursue growth deals. This assumption limits their strategic options. The reality is that dozens of deal structures are available to businesses of every size, yet most entrepreneurs only explore a fraction of what's possible. From acqui-hires that appear to be acquisitions but are actually strategic hiring initiatives, to licensing agre...

Hikari Senju did something different. While everyone else was chasing VCs, he built Omneky to millions in revenue first. After seeing AI generate art at MIT, this Harvard CS grad knew the future. But when investors didn't bite in 2018 ("AI is vaporware," "advertising is too competitive"), he didn't give up. He bootstrapped. Two years. Living hand-to-mouth. Building real revenue. His philosophy: "B...

Most real estate developers think they need institutional investors or private equity to scale their projects. Ryan Andrews proved you can raise millions locally while building stronger community connections. Here's what makes this approach powerful: His $8 million fund is 80% local investors who show up to city council meetings advocating for his projects. These aren't just silent money partners....