OPERATORS, What is it really like to run a business?

October 15, 2025

by a searcher from Imperial College London in London, UK

There are so many searchers with excellent cv’s, but no real management experience beyond managing a handful of interns or other juniors in white collar jobs. Those who have acquired, and come from this background, can you share your experience? - Do you believe you truly understood the CEO role in a small business while searching? - What have you found most difficult? - How learnable is the skill

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Reply by a professional
from University of California, Hastings College of Law in Petaluma, California, United States

Hopefully, I'll answer this fully! Having spent the past few years working closely with Search CEOs, especially in their first 12–18 months post-acquisition (and running growth for a Search company for 5 years until we exited in Dec. 2023), I’ve seen some consistent pattern emerge. From the outside looking in, most searchers intellectually understand what the CEO role entails during diligence, and are fully capable. But once they step in, the reality hits fast: and it’s not just strategy, or playbooks or book knowledge, it’s context switching across 15 disciplines a day. As a Search CEO you’re building trust with legacy teams (people first, I always suggest), managing investor expectations, and learning how to operationalize growth, all while trying to not lose momentum. The hardest parts aren’t usually financial or structural. They often times are people, rhythm, and visibility. Getting a team to believe in a new cadence, and a new mission in the first 90 days is one of the biggest challenges I've seen. Aligning around data (or lack thereof). Making decisions without complete information is also a key challenge. The encouraging part is that most of it is learnable, but I've often seen it’s not something you learn from books or MBA frameworks. Here's my biased take: It ends up being accelerated when you surround yourself with proven operators, fractional GTM leaders, CROs, RevOps leaders, operation experts, who’ve lived through those early-stage pivots and can help you see around corners and navigate minefields. By focusing on short, outcome-driven sprints with defined exit gates, every Search CEO can move measurable value levers and build a lasting success story. Again, I'm biased because all of this is why we built my company, Five Experts: to make it easier for Search CEOs to get that kind of support on-demand, without the time and expense of hiring full-time. I’ve seen time and again that the first five years are where growth becomes real and value is truly measured, and our goal is to help every Search CEO turn that journey into a success story. Thanks for posting and happy to help in any way!

Reply by a searcher
from University of Georgia in St. Louis, MO, USA

Coming from a corporate environment, the biggest learning is that what I thought was businesss - building PPTs, running spreadsheets, meetings, etc. - is not business. It's working in corporate. SMB ownership / leadership is much more about managing team conflict, selling new clients, handling fires, and answering questions. I think there's this perception in the search community that you do this search process, find a perfect business, and then sit in the corner office. That has not been the reality that I've seen for myself or others. It's much more of a full-contact day trying to steer an organization from inside the belly of the beast. That's not to say it's bad; it's just different than what the outside perception is.

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