A few lessons learned (taking a break from searching)

searcher profile

March 24, 2026

by a searcher from DePaul University in Chicago, IL, USA

After getting five LOIs of increasing revenue and SDE signed over time, and going almost to the finish line for the fifth one after working my way through the SBA loan process last month in the midst of government shutdown drama, I decided to take a break. A few of the lessons I've learned, some of which I already knew. But as they say, experience is the best teacher: - Deals really can fall apart at any time. In my case, seller trustworthiness quickly fell apart for my last deal during my onsite visit while shadowing the seller's phone calls. Once I heard them, other pieces of the puzzle came together. I definitely dodged a bullet. - Don't succumb to the sunk cost fallacy. I stretched my comfort level a bit too far during my last deal. While I'm a data guy who doesn't like to over-rely on my gut, my gut ended up being correct. It was hard to pull out, but in retrospect I'm glad I did. - Financials really are just a small part of the equation. I don't know how many times I heard, "But Erik, the financials are so great." Working through P&L statements and tax returns was initially challenging for me as an inexperienced searcher, but no longer. Operational / commercial due diligence is the hard part. - That the individual lender can matter more than the bank itself is completely true. For my SBA loan, I worked with two lenders. Unfortunately, the lender that explained everything in depth and with whom I'd like to work again is also the one who got a delayed start on my deal, so I went with the other lender but didn't learn anything from them. Fortunately, I ended up working my way through the SBA loan process in a timely manner with one and got some tools for my toolbox for future deals from the other. - The search process is a roller coaster. The highs can definitely get high, and the lows can definitely get low. I've definitely gotten ahead of myself on too many occasions. But I've gotten much better about this over time.
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commentor profile
Reply by a lender
in Falmouth, MA, USA
Nice breakdown, Erik. No deal is better than a bad deal. For all searchers out there, financials matter and deserve your time, but ask yourself what it takes for the business to keep earning these profits, assuming they are correctly stated and not misrepresented. The individual lender’s credibility matters a lot, but as deals get more complex, additional support is often needed to ensure the buyer is seen as a serious counterparty, especially since the buyer is typically underrepresented relative to the seller. A good debt advisor can help bridge that gap through structuring, positioning, and anticipating issues early. Enjoy the break now. redacted
commentor profile
Reply by a searcher
from University of Illinois at Chicago in Chicago, IL, USA
Can you provide some insight around your take on operational / commercial due diligence when reviewing a deal .
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