From Angel To Exit

Bruce Eckfeldt
  • 5.0 (1)
  • 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. 3D AGO

    32: How Founder Complacency Kills Value—and What Scott Allison Did Differently

    What do you do when you hit “enough”—but your business still has room to grow? In this episode, Scott Allison, co-founder of Allison Marketing, shares how he scaled a boutique PR firm into a global agency with 52 offices and $100M in revenue. He dives into the challenges of founder complacency, the nuances of strategic M&A, and how he architected a smooth, 11-year earn-out. From exit readiness to post-acquisition purpose, this is a masterclass in growing and exiting with intention. Key Takeaways: “Growth is a decision”—you must consciously commit and act to scale. Founder complacency is a major threat to long-term business value. Timing specialist hires correctly is crucial for sustainable growth. Strategic M&A can be a major growth engine—if you plan early and stay methodical. A thoughtful, multi-year exit plan leads to better terms and less regret. Emotional detachment from deals is key—don’t fall in love with the transaction. Identity and purpose after exit require just as much planning as the deal itself. Smooth leadership transitions take time; gradual step-downs work best. Timestamps: 00:16 – Introduction to the episode and sponsor message 01:24 – Meet Scott Allison, co-founder of Allison Marketing 02:03 – Scott's early career and unexpected path to entrepreneurship 04:52 – Building a company from scratch and facing early challenges 06:07 – The growth of Allison Marketing to a global presence 08:07 – Key lessons learned in leadership and scaling a business 11:24 – The role of acquisitions in business growth 13:24 – Transitioning from CEO to a new chapter 15:28 – Advice for entrepreneurs considering selling their business 18:24 – Scott's future plans and passion projects Links & Resources Scott Allison Website: https://www.allisonworldwide.com/ Email: allisoncommunications@gmail.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

  2. NOV 24

    31: How to Avoid Deal Disasters: Why Founder-CEOs Need a Dedicated M&A Lawyer Before Selling

    In this episode, deal lawyer Chad Williams, Partner at Lamb McErlane, shares insider strategies for founder-CEOs preparing to exit. From why every founder needs a dedicated M&A lawyer to how to handle LOIs, earnouts, and non-competes, Chad walks through the full deal lifecycle. Learn what to do a year before selling, how to protect yourself post-sale, and how to avoid common legal traps that erode value. This conversation is packed with actionable legal insights for founders navigating the complex world of business exits. Key Takeaways Engage a deal-specific lawyer early—ideally 12+ months before selling. Build a diligence-ready data room well in advance of marketing the company. Always know your walkaway point—emotionally and financially—before starting negotiations. Earnouts are risky; structure clear terms or avoid them entirely. Get clarity on whether the deal will be structured as an asset or equity sale. Use rep and warranty insurance to minimize post-close liability. Align internal deal team and external advisors around clear objectives and must-haves. Plan early for what comes after the exit—professionally and personally. Links & Resources Chad Williams Website: www.lambmcerlane.com LinkedIn: Chad Williams on LinkedIn 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

  3. NOV 10

    30: From Broke to Multi-Exit Founder: How Solving Real Problems Built Two 7-Figure Companies

    From hustling for baseball cards as a kid to exiting multiple businesses, Travis Luther shares his extraordinary journey of entrepreneurship, reinvention, and impact. In this episode, Travis opens up about building and selling Queen Anne Pillow and Trial Line, the emotional complexities of life post-exit, and his new mission with Moso Pillow. Packed with raw insights, hard-won lessons, and founder-to-founder wisdom, this is a must-listen for any entrepreneur aiming to scale with purpose and exit with clarity.   Key Takeaways: Solving a real, painful market problem is more important than building a passion project. Choose business partners with complementary skills—not just shared interests. Know your exact cost of goods sold to price effectively and grow profitably. Valet Ads taught Travis about high-margin, scalable ideas hidden in plain sight. Queen Anne Pillow scaled fast with SEO and customer education during COVID. Selling too soon without testing the full market may leave money on the table. Life post-exit can bring emotional uncertainty if you haven’t planned what’s next. Travis’s new venture, Moso Pillow, aligns impact, purpose, and entrepreneurship. Links & Resources Travis Luther https://www.travisluther.com @travisscottluther 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

  4. NOV 3

    29: Founder Fatigue, Deal Drama & the Power of Values in a Successful Business Exit with Gregg Lederman

    In this raw and powerful episode, Gregg Lederman shares how he scaled his values-driven SaaS company, Brand Integrity, from consulting to licensing—and ultimately sold it to a global buyer. He reveals the emotional toll, deal setbacks, and ethical challenges he faced, and how staying true to his core values helped him through. Gregg now leads “A Great Life Now,” helping leaders find purpose and self-awareness. This episode is a must-listen for founders navigating growth, burnout, and business exits.   Key Takeaways: A values-based culture helped Brand Integrity stand out in a crowded market. Hiring people better than yourself is critical to scaling a founder-led business. M&A processes often lack integrity—be prepared emotionally and ethically. Not raising capital allowed control but limited speed—tradeoffs matter. Founders should define personal values before engaging in an exit. “Retrading” in M&A is real—expect late-stage changes in deal terms. Staying aligned with company culture should outweigh the highest valuation. Therapy and self-awareness can be survival tools during exit stress. Links & Resources Gregg Lederman  greg@gregglederman.com gregglederman.com hello@agreatlifenow.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

    46 min

  5. OCT 23

    28: Burned by Broad Services? How Specialization Scaled Pedestal Search to a Successful Exit

    Aaron Levenstadt, founder of Pedestal Search, shares how he went from early days at Google to building and exiting a successful SEO-focused agency. In this episode, he breaks down the power of narrowing services, mastering buyer psychology, and awakening sleeping leads through smart systems. His story offers actionable insights for founder-CEOs navigating growth, productization, and business exits. If you're scaling an agency or considering your own exit strategy, this episode is a goldmine.   Key Takeaways Specializing in one core service enabled true scalability and efficiency. Buyer psychology is essential—structure sales conversations like a landing page. Systematized warm outreach turned dormant leads into high-conversion pipelines. Saying no to work outside your niche builds stronger client trust and delivery results. Reframing sales and post-sale language unifies team efforts and drives clarity. Presenting "reasons not to buy" in M&A builds credibility and smooths diligence. Productization creates repeatability without losing personalization. Planning for exit early enables more favorable deal structures and post-sale freedom. Chapters: 00:00 Introduction to Aaron Levenstadt and Pedestal Search 02:25 Aaron's Journey: From Google to Entrepreneurship 05:07 The Birth of Pedestal Search 08:17 Sales Psychology and Effective Communication 11:24 Refining the Business Model and Focus 14:16 Identifying Ideal Clients and Scalability 17:03 Key Inflection Points in Growth 19:18 Navigating Challenges and Client Conversations 20:38 The Importance of Strategic Guidance 22:46 Awakening Sleeping Leads 25:01 Navigating the Exit Strategy 28:45 Structuring the Deal 31:19 Lessons Learned from the Deal 34:49 Building Trust in Negotiations 40:04 Post-Exit Ventures and Future Plans 42:31 Introduction to the Conversation 42:32 Exploring Key Themes and Insights Links & Resources Aaron Levenstadt LinkedIn: Aaron Levenstadt Email: aaron@joinagencyalliance.com Website: joinagencyalliance.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

    43 min

  6. OCT 13

    27: Struggling With Niching? How Erik Olson Used SEO and Structure to Scale 3 Agencies

    From civil engineer to multi-agency founder, Erik J. Olson shares how he built Array Digital, Rival Digital, and Crush Digital by focusing on niche verticals, systematization, and recurring revenue. In this episode, he breaks down how he de-risks niching, structures scalable operations, and preps for a $100M exit by building a PE-ready platform brand. Founders looking to scale with structure—or build something worth acquiring—will find playbook-worthy insights throughout. Key Takeaways Pivoted from software development to digital marketing after discovering greater long-term value in recurring services. Built three niche-focused agencies with distinct brands to balance risk and maximize focus. Developed a repeatable playbook to launch new agencies: leader + niche + first customer. 91% of current revenue is recurring—key for private equity interest. Created Proxa Brands as the platform-level entity to unify and eventually exit the portfolio. Plans to grow via both organic launches and targeted acquisitions of $500K–$1M agencies. Implemented strong process automation (e.g., Asana templates, Zapier) to streamline onboarding and operations. Culture and post-sale leadership retention are essential in structuring for a PE-ready business. Links & Resources Erik Olson Email: erik@proxabrands.com Instagram: @erik.j.olson 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

    50 min

  7. OCT 6

    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

  8. 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
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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
    33
  • Rating
    Clean
  • Copyright
    © Copyright 2025 All rights reserved.
  • Show Website
    From Angel To Exit