From Angel To Exit

In this episode, Bruce Eckfeldt sits down with John Ratliff, founder of Appletree Answers and now a partner at Align5 and advisor at STS Capital Partners. John shares the behind-the-scenes story of growing a call center business through 24 acquisitions—all without outside capital—and selling at a 14x EBITDA multiple. He also reveals how founders get taken advantage of by sophisticated buyers, and what you must do to avoid selling f...

What does it really take to exit a business successfully—and profitably? In this episode, Bruce Eckfeldt interviews Neil Schaffer, CEO of Carlton Advisors, on his experience scaling companies through M&A, raising over $40 million in strategic capital, and executing billion-dollar exits. Neil shares the real metrics buyers care about, the dangers of founder burnout, and why the emotional side of selling is just as critical as th...

Robert Heil, CEO of Financial Aid Services, reveals lessons from scaling EdTech ventures, leading M&A deals, and transitioning into the CEO seat post-founder exit. With experience on both sides of the table, Robert dives into how customer drivers, leading indicators, and cultural integration can make or break a deal. Learn how he doubled growth and aligned mission with private equity goals—all while navigating the challenges of...

Matthew Diteljan co-founded a startup with just $1,500 and scaled it into a national advertising platform targeting high schools. After a partner buyout and burnout, he exited the company—but not without hard lessons. In this raw, honest conversation, Matthew shares how his dream exit turned into unexpected post-sale turmoil, what he’d do differently, and what every founder should consider before pulling the trigger on a deal.

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What do you do when the dot-com bust kills your $15M funding round just two weeks before closing? In this episode, Bruce Eckfeldt speaks with Roy Vella, co-founder of NetAbacus (later Rivio), who faced a sudden capital crisis in 2000. Instead of folding, he created an employee salary deferral program that extended runway and impressed potential buyers. Roy shares how transparency, co-opetition, and integratable business models shap...

What happens after you sell your company for millions and walk away with no earnout? In this episode, Bruce Eckfeldt sits down with Thomas Michael, a former SAP consultant turned founder who scaled an online training company and exited with a clean deal. Thomas shares how he transformed his business into a subscription model, prepared for acquisition with precision, and what surprised him most after the sale. A must-listen for foun...

Frank Williamson, CEO of Oaklyn Consulting, joins Bruce Eckfeldt to explore what happens when a business stagnates—performing decently, but not meeting growth or exit expectations. He shares real-world insights on managing misaligned cap tables, preparing for strategic exits, and dealing with investor pressure. Frank offers clear tactics to transform underperforming assets into saleable opportunities, making this episode a must-lis...

In this episode of From Angel to Exit, serial entrepreneur Sam Arman shares how he built and sold multiple companies—sometimes under pressure, sometimes for massive wins. From his first computer assembly business disrupted by Dell to a 10X private equity-backed exit during COVID, Sam reveals the emotional and strategic pitfalls founders face in M&A. He dives into how to choose the right buyer, protect your team’s morale, and le...

In this episode, Lysle Wickersham shares his journey from creative director to scaling a $170M agency and navigating multiple exits. As founder and CEO, he emphasizes the power of brand equity in driving enterprise value and achieving successful exits. Lysle breaks down how early-stage businesses can align positioning, brand strategy, and operations to create sustainable growth and higher transaction multiples. His insights bridge ...

David Turner, CEO of Velocity Now and former CRO at IHS, joins the show to unpack what truly drives successful business exits. With firsthand experience leading 47 acquisitions and scaling IHS from $320M to $1.8B, David offers rare insight into the buyer’s mindset. Founders will gain actionable strategies to prepare for sale, avoid common missteps, and understand how to position their company for maximum value.

Key Takeaways

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In this episode, Leslie Kraatz Adams shares the remarkable journey of scaling and exiting Federal Metals, a third-generation scrap metal business. Starting with deep family roots and evolving industry dynamics, Leslie transformed the company from a local scrapyard into a major regional player in Western Canada. She candidly discusses leadership challenges, navigating family dynamics, preparing for sale, and her pivot into health an...

From washing cars as a teen to selling a business with over $290M in sales, Calvin Johnson’s entrepreneurial journey is nothing short of remarkable. In this episode, Calvin shares how he built and exited Lykki, an office supply and coffee delivery company, and the key lessons he learned around culture, technology, and timing. Founders looking to scale smart and exit well will gain real-world insights into M&A strategy, deal pre...

In this episode, Bruce Eckfeldt interviews Jordan Youkilis, founding partner of Key Investment Partners, to explore how cannabis investing offers unique challenges and opportunities for founders. Jordan shares his journey from traditional finance to cannabis private equity, highlighting lessons in capital deployment, deal structuring, and scaling businesses in tightly regulated environments.

Key Takeaways

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