From Angel To Exit

What if you could sell your company—twice? In this episode, Bruce Eckfeldt talks with Matthew Porter, founder of Contegix and now Partner & Co-Founder at EONOVA, about how he bootstrapped a data center company, scaled it through acquisition, and sold to private equity—twice. Matthew shares the behind-the-scenes of deal negotiations, what he learned from his first exit, and how a second sale tu...

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 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 o...

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...

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...

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, an...

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 aft...

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 opportunit...

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,...

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...

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 transact...

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...

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 insig...

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 T...

Serial entrepreneur Pete Martin joins the show to unpack his journey across four business exits, including a standout 12x EBITDA sale to KPMG. Drawing from both personal and professional highs and lows, Pete shares powerful lessons on building scalable, values-driven companies, designing for exit, and avoiding the common pitfalls that sabotage founder success. From crafting a cultural manifesto to...

Alan McLaren, co-founder of Strata Originals, shares his journey from corporate leadership to entrepreneurial success. In this episode, he reveals how he scaled two marketing agencies, built a powerful personal branding firm, and supports founders preparing for strategic business exits. Alan discusses M&A readiness, founder well-being, and how personal branding plays a crucial role in business...

In this episode of From Angel to Exit, host Bruce Eckfeldt sits down with Darren Mass, the founder of Mass Communications, to discuss his entrepreneurial journey from launch to acquisition. Darren shares how his early fascination with engineering led him to build a successful telecom company, the strategies he used to scale, and the key decision points that led to a $40 million exit. He also refle...

Todd Taskey, an M&A advisor and angel investor, joins Bruce Eckfeldt to discuss the nuances of business exits and private equity partnerships. Taskey explains the importance of structuring deals to optimize cash, equity, and earnouts. He highlights how founders can use a sale to accelerate growth rather than just exit, and shares real-world examples of successful second-bite opportunities. Thi...

In this episode of From Angel to Exit, Bruce Eckfeldt speaks with Suren Kapse, a seasoned advisor and coach specializing in M&A and exit strategies. Suren shares hard-earned insights on how founders can prepare for successful exits, whether selling for people, assets, scale, or client access. He also unpacks how buyers evaluate cultural fit, valuation dynamics, and when to go international. A...

Shawn Freeman, founder of a successful managed service provider (MSP), joins Bruce Eckfeldt to share his journey from launching a tech side hustle to scaling a $5M business and executing a 1.4x revenue exit. He reflects on key inflection points in leadership, recurring revenue strategy, and the emotional and operational complexities of being acquired. Shawn’s insights are essential for founder-CEO...

In this episode of From Angel to Exit, Bruce Eckfeldt speaks with serial entrepreneur Shreesha Ramdas about his journey from risk-averse engineer to founder of multiple successful startups. Shreesha shares his unique “startup fitness” framework, lessons from bootstrapping LeadFormix through to its acquisition by SAP, and his current work with Lumber, a workforce optimization platform for the const...

In this episode of From Angel to Exit, host Bruce Eckfeldt sits down with Eddie Geller, serial entrepreneur and founder of Unique World, to unpack the gritty, insightful journey from launching early web services to a high-stakes M&A exit. Geller candidly shares the highs and lows of scaling a business, from client concentration pitfalls to post-acquisition culture clashes. This episode is rich...

In this compelling episode of From Angel to Exit, Bruce Eckfeldt interviews Vlada Lotkina, founder of ClassTag, an EdTech platform that transformed parent-teacher communication. From her entrepreneurial upbringing in Ukraine to a successful exit in the U.S., Vlada shares the challenges of monetizing in the K-12 sector, navigating a failed M&A, and rethinking her strategy for venture number two...

In this sharp and candid episode of From Angel to Exit, Bruce Eckfeldt interviews Bill Snow, Managing Director at Focus Investment Banking and author of several books on M&A. With nearly two decades of experience in the middle market, Bill shares blunt truths and practical advice on what it really takes to sell a business. From valuation myths to private equity dynamics, this episode is packed...

In this episode of From Angel to Exit, Bruce Eckfeldt speaks with entrepreneur and investor Joshua Maidan, whose journey from Colombia to New York led to the creation of a high-end coffee brand with international acclaim. Maidan shares how he scaled the business using real estate savvy, aggressive strategy, and deep operational structure. The episode centers on how misaligned visions and lack of c...