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Show HN: It took 4 years to sell my startup. I wrote a book about it

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Re: Show HN: It took 4 years to sell my startup. I wrote a book about it

#51
post #29
post #18

I really enjoy the actual content of the few chapters I read so far, but the styling is 100% LLM, and it's so hard to get through multiple pages of the same exact mannerisms repeated over and over and over. It kind of feels like reading the world's longest LinkedIn post. I really wish this wasn't the case because I really want to take in the story and lessons, but it's literally too fatiguing to get through much in o…

Yeah this is a bit sad. I think maybe this person actually had some real lived experience and wrote bullet points and then generated the book. I don’t even want to think about the possibility that the whole thing, including anecdotes, might be generated. I skimmed the content (it has no immediate relevance to my life) but even the chapter headings are sloppadocious.

>lived experience

Not to derail your comment, but what is the purpose of prepending the word "lived" to the word "experience"? Is there experience that's not lived? It's strange to me to imply that knowledge gained from others telling you about something can be called "experience". I've seen the term pop up in particular circumstances in the last several years and it smacks to me of a dog whistle.

Re: Show HN: It took 4 years to sell my startup. I wrote a book about it

#52
We've gone full circle. I asked Gemini what is the sale price and I got this answer:

"Within the tech community (such as discussions on Hacker News), estimates have varied wildly. While some speculate on a "9-figure" deal (over $100 million), others suggest a more modest range of $10–$20 million based on Polarr's estimated revenue and team size at the time of the sale."

Re: Show HN: It took 4 years to sell my startup. I wrote a book about it

#53
post #29

Earlier quoted context omitted.

Yeah this is a bit sad. I think maybe this person actually had some real lived experience and wrote bullet points and then generated the book. I don’t even want to think about the possibility that the whole thing, including anecdotes, might be generated. I skimmed the content (it has no immediate relevance to my life) but even the chapter headings are sloppadocious.

>lived experience Not to derail your comment, but what is the purpose of prepending the word "lived" to the word "experience"? Is there experience that's not lived? It's strange to me to imply that knowledge gained from others telling you about something can be called "experience". I've seen the term pop up in particular circumstances in the last several years and it smacks to me of a dog whistle.

You can experience things second hand. I wouldn’t object to someone saying ‘my experience with chemo’ when talking about their spouse’s disease. They can tell you not just the symptoms but what their insurance company did etc.

Still while watching a loved one deal with cancer is an intense experience and gives you way more insight than you had before you didn’t have the lived experience of having cancer, thus the distinction.

Re: Show HN: It took 4 years to sell my startup. I wrote a book about it

#54
post #29

Earlier quoted context omitted.

Yeah this is a bit sad. I think maybe this person actually had some real lived experience and wrote bullet points and then generated the book. I don’t even want to think about the possibility that the whole thing, including anecdotes, might be generated. I skimmed the content (it has no immediate relevance to my life) but even the chapter headings are sloppadocious.

>lived experience Not to derail your comment, but what is the purpose of prepending the word "lived" to the word "experience"? Is there experience that's not lived? It's strange to me to imply that knowledge gained from others telling you about something can be called "experience". I've seen the term pop up in particular circumstances in the last several years and it smacks to me of a dog whistle.

It’s a form of contrastive reduplication. Used to emphasize the realness of the experience, versus like second hand experience like interviewing those who have the actual experience.

Also consider a phrase like “work work” versus “school work”. For someone who both works a paid job and goes to school, clarifying that they need to do “work work” makes sense.

Re: Show HN: It took 4 years to sell my startup. I wrote a book about it

#55

Really appreciate the deep dive here. M&A is the final boss of startups and so rarely do we get any credible, detailed information about how things go down from the founder's perspective, especially at the 9+ figure deal size. Having written a book about pivots, I know how hard it can be to then distill a grueling experience into something digestible. Thank you Derek!

thanks jason, really appreciate the perspective, will checkout your book!

Re: Show HN: It took 4 years to sell my startup. I wrote a book about it

#57

As a founder fortunate enough to get to and through a positive acquisition, just reading the chapter outline and clicking into a few I can see there's useful perspective here I wish I'd had. Since the situation is pretty rare there's not a lot of info for founders from founders. As it was I had to figure it out as it happened. I managed to thread the needle while avoiding any major pitfalls but it was a close thing t…

Congrats on your exit! Your note reminded me something Ezra Roizen wrote in Magic Box Paradigm. Paraphrasing here, he said that M&A outcomes often feel miraculous, but then again, babies are miracles too, and they happen every day :)

Re: Show HN: It took 4 years to sell my startup. I wrote a book about it

#58

Does anyone know of any other resources like this for new founders to understand the experiences of experienced founders? This seemed very candid and earnest - it's rare that these don't sound like personal branding pieces. I'd love to build a collection. This one was superb.

Here are all the materials/books that were useful while I was in the thick of it: Bilal who sold his startup to Amplitude: https://bilalmahmood.medium.com/how-to-sell-your-startup-744... Touraj who is the COO of Serve Robotics and previously did a couple M&As and was leading Corp Dev at GoDaddy: https://www.amazon.com/Exit-Path-How-Startup-Game/dp/1264703... Ezra's book on Magic Box Paradigm: https://www.amazon.com/Magic-Box-Paradigm-Framework-Acquisit...

Re: Show HN: It took 4 years to sell my startup. I wrote a book about it

#59
post #43

"Built to Sell" is a better book, starting with the premise that your company needs to be positioned to be bought, not sold. If you are reaching out to someone to buy you, you are effectively accepting an 80% price cut.

Good call out! This book was definitely useful in terms of thinking about specialization before testing the market. There was even a sequel to it I believe.

However, the general audience for "Built to Sell" is for SMBs and does not cater towards the venture-backed technology startups here in the valley (who hope for a strategic acquisition instead of a ebidta multiple).

Re: Show HN: It took 4 years to sell my startup. I wrote a book about it

#60
post #18

I really enjoy the actual content of the few chapters I read so far, but the styling is 100% LLM, and it's so hard to get through multiple pages of the same exact mannerisms repeated over and over and over. It kind of feels like reading the world's longest LinkedIn post. I really wish this wasn't the case because I really want to take in the story and lessons, but it's literally too fatiguing to get through much in o…

OP here, thanks for this feedback, my workflow was to first have a draft and then feed it into a LLM to fix grammar and improve conciseness. Wished there was a tool (I think folks are already working on) that is similar to what a book editor does which suggests changes as opposed to changing the styling.

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