From Angel To Exit

Bruce Eckfeldt
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  • ENTREPRENEURSHIP

From Angel To Exit is a business podcast exploring the entrepreneurial journey of scaling a business from raising your first round of funding to exiting. We cover the trials and tribulations that founders face, the pitfalls and pratfalls you want to avoid, as well as the joy and impact that success can bring. Join us on our next episode, where we speak about the challenges that real leaders face growing and scaling their organizations and how they’ve overcome them to achieve success and make their mark.

  1. 6D AGO

    26: How to Sell the Same Company Twice — And Exit With More Every Time

    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 turned lessons into leverage.   Key Takeaways: You can sell your company twice—if you structure the first exit with a second in mind. Founder identity and mental health are critical in long-term exit strategy. Private equity isn’t the enemy—but you must understand their value model. Second exits offer a rare chance to fix what you missed the first time. Growth through acquisition drives both scale and valuation. Negotiate your role, not just your price, post-exit. Build with optionality: prepare for a sale, even if you’re not planning one. Fit and alignment often matter more than the highest bidder. Links & Resources Matthew Porter Email: mporter@enova.co https://www.linkedin.com/in/meporter/ Subscribe to the Podcast: Find From Angel to Exit on Apple Podcasts, Spotify, Google Podcasts, or wherever you listen. Be sure to hit “Subscribe” so you never miss an episode. Newsletter & Exclusive Content: Sign up for the free newsletter at eckfeldt.com/podcast for episode transcripts, bonus insights, frameworks, and community updates. Connect with Bruce & the Community: LinkedIn: Bruce Eckfeldt Instagram: @bruce_eckfeldt Email: podcast@eckfeldt.com bruce@eckfeldt.com

    47 min

  2. SEP 29

    25: How to Buy 24 Companies with No Cash and Sell for a 14x Multiple — John Ratliff’s Playbook

    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 for less than you're worth. Key Takeaways: You can scale through acquisitions without raising outside capital—if you master bank relationships. Know your strategic value inside the buyer’s ecosystem—it’s often worth more than your financials show. A strong exit multiple (14x) is possible when you’re the most coveted asset in a fragmented market. Bank relationships should be treated like partnerships, not vendor agreements. Your personal finances and lifestyle must be exit-ready before the deal closes. Never use your company email as your personal email—it could be gone post-exit. Build acquisition teams internally with cross-functional talent, not full-time M&A staff. Think like a buyer: reverse engineer how your capabilities create value after acquisition. Links & Resources John Ratfliff Email: Apple Podcasts, Spotify, Google Podcasts, or wherever you listen. Be sure to hit “Subscribe” so you never miss an episode. Newsletter & Exclusive Content: Sign up for the free newsletter at eckfeldt.com/podcast for episode transcripts, bonus insights, frameworks, and community updates. Connect with Bruce & the Community: LinkedIn: Bruce Eckfeldt Instagram: @bruce_eckfeldt Email: podcast@eckfeldt.com bruce@eckfeldt.com

    46 min

  3. SEP 22

    24: Think You’re Exit Ready? Neil Schaffer’s 1,000-Day Rule Will Change Your Mind

    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 the financials. If you're a founder thinking about your next move, this is your exit planning playbook. Key Takeaways: Exits require emotional readiness—ask what you want from the transaction. Strategic buyers often pay more than financial buyers—understand their value drivers. The 1,000-day exit plan ensures time for operational and financial preparation. Valuation ≠ buyability—culture and competitive advantage often seal the deal. Raising capital? Your story, not just your spreadsheet, sells the investment. Equity vs. debt: Choose based on market conditions, cash flow, and growth stage. Founders must systematize knowledge—buyers don’t pay for what's only in your head. Treat exit strategy as a quarterly strategic planning item, not a one-time event. Links & Resources Neil Schaffer Email: https://carltonadvisorsllc.com Subscribe to the Podcast: Find From Angel to Exit on Apple Podcasts, Spotify, Google Podcasts, or wherever you listen. Be sure to hit “Subscribe” so you never miss an episode. Newsletter & Exclusive Content: Sign up for the free newsletter at eckfeldt.com/podcast for episode transcripts, bonus insights, frameworks, and community updates. Connect with Bruce & the Community: LinkedIn: Bruce Eckfeldt Instagram: @bruce_eckfeldt Email: podcast@eckfeldt.com bruce@eckfeldt.com

    42 min

  4. SEP 15

    23: How Robert Heil Doubled Growth by Rebuilding Strategy Around Client Value Creation

    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 higher education’s complex ecosystem.   Key Takeaways: Track leading indicators, not just lagging metrics, to create sustainable business value. Successful M&A starts with understanding customer concentration and growth drivers. Post-deal integration planning should begin before the ink is dry—especially around culture. Private equity partners want growth, but strategic balance across stakeholders is key. Use strategic planning frameworks like Metronomics to align internal teams and exit readiness. Value creation for clients naturally leads to shareholder and team success. The first 30 days post-acquisition are critical—have a plan, even if it’s not perfect. Customer feedback often reveals the true cultural DNA of an acquisition target. Links & Resources Robert Heil https://www.robert-heil.com/ https://www.linkedin.com/in/robert-heil-88966623/ Subscribe to the Podcast: Find From Angel to Exit on Apple Podcasts, Spotify, Google Podcasts, or wherever you listen. Be sure to hit “Subscribe” so you never miss an episode. Newsletter & Exclusive Content: Sign up for the free newsletter at eckfeldt.com/podcast for episode transcripts, bonus insights, frameworks, and community updates. Connect with Bruce & the Community: LinkedIn: Bruce Eckfeldt Instagram: @bruce_eckfeldt Email: podcast@eckfeldt.com bruce@eckfeldt.com

    44 min

  5. SEP 8

    22: How Bootstrapping With $1,500 and Cold Calls Built a Multi-Million Dollar Ad Business

    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. Key Takeaways Starting with constraints forces creativity and sharpens focus. Bootstrapping helps you stay lean—but can limit scale if you resist outside capital. Partner alignment is critical; buyouts can get messy without strong communication. Abdicating leadership too early can trigger chaos; train successors with care. Walking away from a subpar offer can bring stronger, unexpected buyers. Your investment banker works for the deal—stay in control of your own vision. Financial freedom doesn’t guarantee peace—post-sale fallout can be brutal. Think beyond the exit: what kind of life and legacy do you really want?   Links & Resources Matthew Diteljan LinkedIn: https://www.linkedin.com/in/diteljan/ Instagram: https://www.instagram.com/mattditeljan/ Subscribe to the Podcast: Find From Angel to Exit on Apple Podcasts, Spotify, Google Podcasts, or wherever you listen. Be sure to hit “Subscribe” so you never miss an episode. Newsletter & Exclusive Content: Sign up for the free newsletter at eckfeldt.com/podcast for episode transcripts, bonus insights, frameworks, and community updates. Connect with Bruce & the Community: LinkedIn: Bruce Eckfeldt Instagram: @bruce_eckfeldt Email: podcast@eckfeldt.com bruce@eckfeldt.com

    48 min

  6. SEP 1

    21: Facing a Runway Crisis? How Employee Deferrals Secured Roy Vella a Successful Acquisition

    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 shaped the acquisition and his later career at PayPal and beyond. Founders will learn hard-earned lessons about resilience, deal-making, and preparing companies to thrive even when markets collapse. Key Takeaways Crises demand creativity: salary deferral saved months of runway and impressed acquirers. Transparency builds trust and accelerates deal-making during tough markets. Employee commitment and culture directly affect perceived acquisition value. Founders must embrace external visibility—storytelling is as critical as strategy. Integration-friendly businesses (API mindset) are far more attractive to buyers. Co-opetition often unlocks unexpected deal opportunities. Post-exit transitions can be jarring; expect emotional and cultural shifts. Strategic investor targeting includes competitors’ backers—who often want diversification. Links & Resources Roy Vella LinkedIn: linkedin.com/in/royvella Subscribe to the Podcast: Find From Angel to Exit on Apple Podcasts, Spotify, Google Podcasts, or wherever you listen. Be sure to hit “Subscribe” so you never miss an episode. Newsletter & Exclusive Content: Sign up for the free newsletter at eckfeldt.com/podcast for episode transcripts, bonus insights, frameworks, and community updates. Connect with Bruce & the Community: LinkedIn: Bruce Eckfeldt Instagram: @bruce_eckfeldt Email: podcast@eckfeldt.com bruce@eckfeldt.com

    42 min

  7. AUG 25

    20: Struggling to Scale Your Expertise? How Thomas Michael Turned SAP Training into a 7-Figure SaaS Exit

    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 founders planning their own exits. Key Takeaways: Switching to SaaS doubled the exit multiple through recurring revenue. Preparing for an exit can take 1–2 years—start early and organize everything. Making yourself unimportant in the business is key to a clean transition. Culture by design significantly improves team morale and buyer appeal. A good advisory board can add millions in value pre-exit. Many buyers will lowball; knowing industry multiples is essential. Post-exit identity loss is real—plan ahead for your next chapter. Don't underestimate the power of financial and operational clarity in due diligence. Links & Resources Thomas Michael Website: thomasmichaellive.com LinkedIn: https://www.linkedin.com/in/thomasmichael1/ Subscribe to the Podcast: Find From Angel to Exit on Apple Podcasts, Spotify, Google Podcasts, or wherever you listen. Be sure to hit “Subscribe” so you never miss an episode. Newsletter & Exclusive Content: Sign up for the free newsletter at eckfeldt.com/podcast for episode transcripts, bonus insights, frameworks, and community updates. Connect with Bruce & the Community: LinkedIn: Bruce Eckfeldt Instagram: @bruce_eckfeldt Email: podcast@eckfeldt.com bruce@eckfeldt.com

    38 min

  8. AUG 18

    19: Managing Mid-Performer Assets: A Tactic for Founders Facing M&A Stagnation

    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-listen for founder-CEOs navigating the murky middle of the M&A landscape. Key Takeaways: If your business can't run without you for two weeks, it's likely not a saleable asset. Separate the "owner" and "operator" roles early to prepare for a successful exit. Mid-performing companies need strategic storytelling and market testing to attract buyers. Investor pressure often stems from their own fund timelines—not just company performance. Framing early buyer outreach as partnerships creates rapport without prematurely signaling a sale. Distinguish between VC (growth-focused) and PE (buyout-focused) when planning capital strategy. A full sales funnel—multiple potential acquirers—is key to creating leverage in dealmaking. Founders must proactively lead the narrative around exit timing, valuation, and deal structure. Links & Resources Frank Williamson LinkedIn: https://www.linkedin.com/in/fwilliamson/ Website: https://oaklynconsulting.com/ Subscribe to the Podcast: Find From Angel to Exit on Apple Podcasts, Spotify, Google Podcasts, or wherever you listen. Be sure to hit “Subscribe” so you never miss an episode. Newsletter & Exclusive Content: Sign up for the free newsletter at eckfeldt.com/podcast for episode transcripts, bonus insights, frameworks, and community updates. Connect with Bruce & the Community: LinkedIn: Bruce Eckfeldt Instagram: @bruce_eckfeldt Email: podcast@eckfeldt.com bruce@eckfeldt.com

    39 min
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From Angel To Exit is a business podcast exploring the entrepreneurial journey of scaling a business from raising your first round of funding to exiting. We cover the trials and tribulations that founders face, the pitfalls and pratfalls you want to avoid, as well as the joy and impact that success can bring. Join us on our next episode, where we speak about the challenges that real leaders face growing and scaling their organizations and how they’ve overcome them to achieve success and make their mark.

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  • Creator
    Bruce Eckfeldt
  • Years Active
    2K
  • Episodes
    27
  • Rating
    Clean
  • Copyright
    © Copyright 2025 All rights reserved.
  • Show Website
    From Angel To Exit