Andrew GazdeckiSerial Entrepreneur Driving Startup Acquisitions

The Most Expensive Part Of Selling A Startup

9 Aug 2026 · 1 min

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In this segment, the speaker explains how founders and entrepreneurs should decide whether to manage the sale of their startup themselves or enlist experienced, hands‑on support. He argues that those who have previously completed deals understand the process and can navigate it solo, whereas first‑time buyers or sellers—or anyone who hasn’t done a deal in a long time—risk costly mistakes, demoralizing failed transactions, and unnecessary friction when dealing with seasoned counterparties. The speaker highlights the tangible value of working with seasoned dealmakers: they know common pitfalls, buyer negotiation tactics, and typical deal structures, which can save time and protect large sums of money in high‑stakes transactions.

Chapters

How do I know whether I need hands-on support or if I can manage the sale myself? If you've done deals before, you already know the process, but if you haven't, that's when you're going to need some help. Because if you go through this process and you don't do a deal successfully because you haven't been through the process, it's very demoralizing whenever a deal falls out. There's just a lot of value with working with someone that's done the deals. And let's say you're a first-time buyer or a first-time seller, or let's say you've only done one deal maybe a long time ago, and let's say the buyer is very experienced, there's going to be a lot of friction Because again, there's tens of thousands, hundreds of thousands of dollars on the line of working with someone that can provide the value to make sure that they've seen it all. We know where the pitfalls are. We know how buyers negotiate. We know what the typical deal structures are. If it's a big enough deal and there's a lot of money on the line and you're busy and there's a lot of time that you can save, work with someone that's done it before, that does it all the time.