Search is often described as a path to entrepreneurship. What’s talked about less is the weight that comes with it.
In this episode of The Transaction Abstract Podcast, Redpath’s Joe Hellman sat down with Rob Cherun, founder and managing partner of Legate Partners, to talk about what happens after the search. They dig into what truly happens when the deal closes, the responsibility sets in, and ownership becomes real.
Rob has lived the full arc. He’s raised a search fund, operated and scaled a business to nearly 2,000 employees across five countries, exited to a strategic buyer, and today he invests in and supports the next generation of searchers. What he shared in this episode of the podcast is a grounded, honest look at what separates success from struggle in the search ecosystem.
Search Is a Long-Term Commitment, Not a Shortcut
After exiting his business, Rob Cherun did what many founders are told to do: he took a break. He surfed. He skied. He started learning Italian. At the same time, Rob stepped back long enough to ask a harder question: “What’s the next mountain worth climbing?”
The answer pulled him back to search, because for him, search was meaningful. Search gave Rob early exposure to ownership, accountability, and real operating responsibility. It forced him into leadership sooner than almost any other path would have. Now, returning as an investor, this next stage in his journey isn’t about deploying capital.
As Rob shared, “The most meaningful way for me to get back wasn't just writing checks or becoming another operator. It was bringing my perspective to searchers who are about to step into one of the hardest jobs they'll ever have. So now, I get to invest in searchers, sit on boards, help with diligence, capital allocation, hiring, and frankly, just being a sounding board when things get tough.”
What Investors Actually Look for in Searchers
In this role today, Rob and his team speak with more than 200 searchers a year and invest in roughly 15. The narrowing comes down to traits, not pedigree or resumes.
What consistently matters most:
As Rob unpacked who they’re looking to partner with, “People have to be comfortable with ambiguity and perfect information and being very coachable and humble. What we look for is kind of someone who's been successful with whatever they've done. We're betting on intellectual horsepower over experience in a lot of ways. We’re asking how you have been successful throughout life and where you have driven impact and results.”
Intellectual horsepower matters, but experience alone isn’t the differentiator. Rob has seen great assets fail under the wrong operator… and average businesses thrive under the right one. Search isn’t about looking good on paper. It’s about grit when things get hard.
Ownership Changes Everything
One of the most practical parts of the conversation centered on responsibility. Running a business isn’t just about strategy and capital allocation. That reality includes broken trucks, missed installs, tired employees, and customers who need answers now, not later. Rob described ownership as carrying responsibility for every stakeholder involved: employees, lenders, customers, suppliers, and investors. This is when leadership shifts from theoretical to visible for everyone involved.
Too often, it’s thought that culture lives in mission statements. In reality, culture is built in the day-to-day through how leaders show up, make decisions, and stay close to the work. Owners who want teams to think like owners have to model it themselves, from cost discipline to being present in the field. This kind of leadership is hands-on, visible, and earned.
The Business Matters, But the Operator Matters More
Legate Partners focuses on what Rob Cherun calls “boring” businesses:
Across sectors, the entrepreneur matters as much as the asset. Some searchers come in with deep industry knowledge. Others are still shaping their direction. Rob looks less at the resume and more at how candidates think, evaluate tradeoffs, and adapt when assumptions break. Versatility, judgment, and integrity carry more weight than a perfect thesis.
Why “Near-Peer” Investors Create Real Value
When asked what differentiates Legate Partners from other investors, Rob didn’t point to check size or structure. He talked about proximity. As a former operator who isn’t far removed from the search journey, Rob described himself as a “near peer”—close enough in age and experience to relate deeply, and early enough in his own career to grow alongside the entrepreneurs he backs.
“I think what differentiates us is having a lot of experience, but still being pretty early in our careers and having done it before. Specific to the search fund side, we look to meet people who are hardworking and have high personal integrity – those are the two recipes for success.”
Supporting that path to success shows up in how Rob engages:
The Throughline: Trust, Grit, and Relationships
As the conversation wrapped, Rob offered advice that applies far beyond search:
“Be honest about what you want. Search is not a shortcut. It’s a long-term commitment to operating a business. When it comes to investors, don't just optimize for capital. Optimize for alignment and experience. The model works best when there's trust, transparency, and real partnership on both sides of the table.”
Search works best when relationships are real, expectations are clear, and everyone is prepared for the long road that ownership requires. Listen to the full episode of The Transaction Abstract Podcast to hear Rob Cherun and Joe Hellman dive deeper into search, ownership, investing, and what it really takes to build and sustain a great business.