Andrew GazdeckiSerial Entrepreneur Driving Startup Acquisitions

How 5 Questions Can Make or Break a Deal

2 Oct 2026 · 1 min

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In this segment, the speaker outlines a practical deal‑evaluation approach that starts with asking five to ten targeted questions. These initial questions are designed to surface major red flags and clarify critical deal terms, especially whether the seller is willing to provide seller financing. The speaker emphasizes that the answers often determine a go or no‑go decision. He shares a personal anecdote: after identifying a promising opportunity, he reached out to the seller, who responded quickly but refused seller financing, leading the speaker to walk away because he could not fund the purchase in cash.

Chapters

So usually it's 5 to 10 questions. And in many cases, the answers to those questions will kind of be the go or no-go for me. Now, my initial questions will generally deal with any major potential red flags or something that isn't clear to me. Also, I want to know if they're open to seller financing, if I know that I won't be able to finance the deal all in cash. I saw a deal that seemed very interesting, and that's what I did. And I wrote the seller, he got back to me very quickly, but, and then he said, no, we can't do seller financing. So I'm like, okay, it's done. Like I can move on because it was a big deal and there was no way I could have, you know, get the cash to do the whole deal.