Confessions of an Implementer S2E37

When EOS Theory Meets Reality with Ned Tomasevic
Host: Ryan Hogan | Guest: Ned Tomasevic
Date: February 25, 2026

Episode Overview

This episode explores what happens when the frameworks of EOS (Entrepreneurial Operating System) and the distinct theories of entrepreneurship meet real-world, on-the-ground implementation—especially in the high-stakes world of private equity, search funds, and SMB (Small and Medium Business) turnarounds. Host Ryan Hogan sits down in person with Ned Tomasevic, a seasoned operator and search fund entrepreneur, to unpack Ned’s journey from finance to finding and buying his own business, the realities of turnaround work, and the deeper truths behind what makes leaders and cultures thrive (or struggle) after the deal is done.

Key Discussion Points and Insights

1. Ned’s Journey: From Banking to Private Equity to Search Funds

• Early Career and Banking: Ned starts in New York banking—feeling out of place in the competitive, edgy environment, he eventually finds a better fit in the Midwest.
  • “I learned really quickly I wasn't a great New Yorker…I developed the edge, but I didn't like it. I didn't want to be on edge all the time.” – Ned ([02:08])
• Consulting & Private Equity: Shifts to bankruptcy consulting in LA, learning turnaround strategies and private equity from distressed deals, including high-stakes work in Honduras.
  • “Sometimes you just make bad choices…the place where we own most of our companies was in San Pedro Sula, which was like the murder capital of the world at the time.” – Ned ([04:07])
• Family Lessons in Entrepreneurship: Though not immediately from an entrepreneurial family, Ned grew up immersed in a Serbian immigrant community surrounded by self-made business owners.
  • “I saw all these people start with nothing and…build truly the American dream in front of my eyes.” – Ned ([19:05])

2. The Myth and Reality of Private Equity

• Perception vs. Reality: PE is glamorized for its “sexy” deals, but Ned emphasizes the volume of failures and the reality of working with struggling companies.
  • “You never hear about that stuff. What are some of the things that…you saw, where it's like, oh, I had no idea?” – Ryan ([06:54])
  • “Sometimes the leadership team is doing great and they just need some support…Sometimes a PE fund sees value in a business and it might not include that leadership team…We looked at it as an asset.” – Ned ([06:54])

Notable Quotes:

• “I think private equity is…a really cool occupation because you get to use your full brain. It's not analyzing, but it's also doing so. You're in the seat with the operator.” – Ned ([08:32])
• “Over time, most BE [PE] fund returns are pretty good. But as we're seeing now, some of them aren't as good. And there's other models to approaching business.” – Ned ([13:33])

3. The Turnaround Playbook: Distress to Opportunity

• Distressed Investing: Higher risk, but PE brings resources, structure, and fresh eyes—sometimes unlocking value simply by “resetting” the scenario.
  • “It just depends on the thesis for each business. And we've got cash that the prior company didn't have. And when you restructure it, you're kind of starting with a blank slate. So that's where it gets a lot of fun.” – Ned ([11:24])
• Leadership in Crisis: PE’s edge is quick execution, directness, and an unwavering focus on results—but great teams can be bruised by arrogance or lack of listening.
  • “They don't mince words. Here's the strategy. We take feedback...and then it's execution.” – Ned ([12:36])
  • “Sometimes where they don’t [do well] is they think they’re right and…piss off the wrong customers, they’re just not open to certain types of feedback.” – Ned ([13:02])

4. What Is a Search Fund? Why Do It?

• Transition from Operator to Owner: Ned couldn’t see himself in pure startups; the search fund model appealed as a bridge between entrepreneurial creativity and the structure of established business.
  • “By trial and error, I realized that this kind of search fund thing was interesting…I just fully bet on myself.” – Ned ([26:36])
• The Search Fund Model Explained:
  • Raise ~2 years’ living costs from investors to find, acquire, and run a small business.
  • Entrepreneurs get minority equity (15-25% after vesting/outcomes), in exchange for board support and risk sharing.
  • “That felt right for me. That fit me.” – Ned ([25:37])
• Sourcing the Deal: Tremendous hustle—mixing cold outreach, brokered deals, and even help from family.
  • “I wrote hand, hand written letters. And at one point it was too much. My mom … can do this for you. So she wrote these handwritten letters for me.” – Ned ([39:08])
  • Contacted 20,000 companies, got to pre-LOI with 800, signed 20+ LOIs before making a deal. ([42:54])

Notable Quotes:

• “If that guy can crush it, I can do it, right?” – Ned on seeing relatable success among portfolio CEOs ([29:42])
• On the core motivator: “The idea that you could build something and that you could have enough money to buy yourself some freedom, freedom from want, freedom from fear…” – Ned ([31:46])

5. Operating: From Day One & Core Values in Action

• First Days as an Acquirer: The announcement is a choreography meant to calm nerves and set tone.
  • “You get up there…what you want to do with it…and ideally, you're setting a tone where the team understands that you really care.” – Ned ([47:54])
• The 100-Day Plan: Meet everyone, listen, document, validate diligence, and identify what's really going on before making moves. ([48:49])
• Long-Term Commitment vs. "Flipping": Ned resists the “flip” mindset—even though most search fund models have implicit 4-6 year holds, the reality is emotional buy-in and team development matter more.
  • “I dislike the term flip because it implies lack of care. You have one person who’s putting all of their professional and a lot of their emotional eggs into that basket.” – Ned ([49:51])

6. People and Culture: Motivation, Core Values, and Letting Go

• Evolving Leadership Insights: Ned shifts away from believing incentives are the primary driver, focusing more on belonging, purpose, and values.
  • “They really, truly want to be part of something bigger than themselves…teams want to stick around when they really believe in what they're doing and they're having fun doing it.” – Ned ([54:16])
• On Letting People Go: Clear communication, humanity, and being a “good lever” are critical—for the good of both the individual and the team observing you.
  • “You can be a great version of yourself even when you have to let someone go.” – Ned ([59:30])

Notable Quotes:

• “If I’m trying to motivate you to do something that you really don’t want to do…there’s really nothing else I can do.” – Ned ([55:28])
• “All we’re really doing is taking this group of people and we’re aligning the human energy of this business to some goal. And that's it.” – Ned ([58:36])

7. Core Values in Practice: Real-World Examples

• Core Values Integration: Ryan shares how his teams (at both Hunt a Killer and Talent Harbor) live values by reciting them, discussing, and recognizing real actions every week.
  • “We recite them, and then we pick one to talk about…then we recognize somebody… specifically for an action decision…that was in line or a demonstration of a core value.” – Ryan ([66:15])
• Ned’s Experience Post-Acquisition: Discovers two clashing sets of values within his acquired company—takes years to integrate and realize the need for alignment.
  • “There was kind of two parts to the business…the founder had one set of core values and…CEO had another set of values. And on their walls were both values. It was wild.” – Ned ([61:15])

Notable Quotes & Memorable Moments

| Quote | Speaker | Timestamp | |---|---|---| | “I learned really quickly I wasn't a great New Yorker...I didn't want to be on edge all the time.” | Ned | 02:08 | | “Sometimes you just make bad choices…the place where we own most of our companies was in San Pedro Sula, which was like the murder capital of the world at the time.” | Ned | 04:07 | | “You never hear about that stuff. What are some of the things that…you saw, where it's like, oh, I had no idea?” | Ryan | 06:54 | | “If that guy can crush it, I can do it, right?” | Ned | 29:42 | | “All we’re really doing is taking this group of people and we’re aligning the human energy of this business to some goal.” | Ned | 58:36 | | “There was kind of two parts to the business…the founder had one set of core values and…CEO had another set of values. And on their walls were both values. It was wild.” | Ned | 61:15 | | “We recite them, and then we pick one to talk about…then we recognize somebody… specifically for an action decision…that was in line or a demonstration of a core value.” | Ryan | 66:15 |

Important Timestamps

• 00:44 - Ned’s early career and banking experience
• 04:07 - High-risk private equity deals in Honduras
• 06:54 - Realities behind “sexy” private equity
• 11:24 - How distressed investing really works
• 14:28 - The many faces and approaches of modern PE
• 19:05 - Ned’s entrepreneurial influences growing up
• 25:37 - Why the search fund model felt right for Ned
• 29:42 - Gaining confidence from seeing relatable leaders succeed
• 39:08 - Family support in sourcing deals (handwritten letters)
• 42:54 - The scale of outreach and persistence required in sourcing
• 47:54 - Day one as a new business owner: setting the tone
• 54:16 - Evolving beliefs about what motivates teams
• 58:36 - The necessity of leadership living core values
• 61:15 - The challenge and importance of core value alignment

Closing Thoughts

This episode offers an unusually transparent, high-energy window into what really happens after the deal closes, when theory meets reality, and frameworks like EOS must be translated into company cultures, tough leadership decisions, and long-term legacy. Ned Tomasevic’s journey from high finance to on-the-ground SMB operator is equal parts inspiring and sobering—anchored by a deep appreciation for people, process, and the ever-present messiness of organizational life.

Stay tuned for Part Two to hear more about Ned’s journey after acquisition.