Advice for an unconventional searcher
February 08, 2026
by a searcher in Cleveland, OH, USA
Looking for perspective from experienced searchers, operators & investors.
I’m 35 and early in my search journey. I do not have a college degree and my background is broad rather than deep: construction trades, commercial real estate brokerage, short-term rentals, and property management. I’ve built and managed things, but I wouldn’t claim to be a master of any single industry. Maybe hospitality since people tend to like me.
My initial focus was on acquiring a smaller business that I could purchase without outside investors, roughly $200k–$300k in SDE at a 2.5–3.2x multiple. After spending time in this community, I’m starting to better understand the added risks at that level: thin margins for error, key-person risk, limited growth levers, and the reality that many of these deals can turn into buying a demanding job rather than a scalable business.
That brings me to a crossroads.
Option one is continuing to pursue smaller acquisitions that I can self fund, accepting the higher operational risk in exchange for autonomy and speed.
Option two is targeting a larger business, say $1M+ in SDE, which likely means bringing on investors. My concern there is credibility. Without a degree or a traditional operating background, I’m unsure how realistic it is to raise capital, even with relevant hands-on experience and strong motivation.
So my question is less about a specific deal and more about strategy. For someone in my position, what tends to be the most realistic path forward?
Is it worth investing time into formal credentials or certifications to improve investor confidence? Is the small-deal route a reasonable proving ground despite the risks? Or is it better to focus on a higher-quality search and work backward into an investor-backed structure?
I’m not looking for shortcuts, just trying to choose the path that gives me the best odds over the next five to ten years. Appreciate any honest perspectives
from University of California, Santa Barbara in Santa Barbara, CA, USA
from Princeton University in New York, New York, USA