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

173 points - last Wednesday at 4:56 PM

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  • gbnwl

    today at 5:35 PM

    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 one sitting.

      • collingreen

        today at 5:59 PM

        > It kind of feels like reading the world's longest LinkedIn post

        I didn't realize how poignant of a criticism this could be. Holy hell that hit hard.

        • neilk

          today at 7:04 PM

          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.

          • zhyan7109

            today at 7:35 PM

            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.

              • quamserena

                today at 7:43 PM

                You can simply ask the model to point out if there are any problems and then fix them yourself. You don't have to copy and paste its output into your book. You can also pay for an actual copyeditor to edit your book.

                  • n_u

                    today at 7:59 PM

                    You can also edit it yourself and then ask a friend, relative, or colleague to read the parts you are struggling with improving. "Does this sentence flow? Is there a better way to say this? Is this confusing?"

                    If you're going to sink time into writing a book, it's worth spending some time editing it so your message gets through clearly. But that's just my opinion, your mileage may vary.

                • Klaus23

                  today at 10:06 PM

                  Perhaps this is what you are looking for: https://www.deepl.com/en/write

                  It corrects spelling errors and improves awkward wording. You can then go and choose alternative sentences or words. Just don't expect any sort of deeper intelligence.

                  • pryelluw

                    today at 8:52 PM

                    Hiring a fairly competent editor is affordable (sometimes even cheap). Specially now that a lot of the commercial copywriting has taken a hit with the ai slop

                • Eridrus

                  today at 6:49 PM

                  I dunno how much folks should trust this as more of an account of his specific journey, given this guy apparently didn't do an 83b election and got stuck with a big tax bill (ch 11).

                    • zhyan7109

                      today at 7:31 PM

                      OP here, 83b didn’t apply in my case as I had only stick options, referenced in chapter 11

                        • Eridrus

                          today at 9:10 PM

                          Yeah, but as a founder, why did you have stock options rather than stock with a vesting agreement?

                          Even early employees can early exercise and file an 83b.

                          This chapter is just self inflicted through bad planning, where the correct advice is to vest stock and make sure you file an 83b when you start the company.

                          The advice everyone should be getting here is not "don't take out a loan", but "make sure you get stock and an 83b"

              • nubg

                today at 5:15 PM

                > Every inbound deserves respect, even if you think you’re not ready. Because the truth is, readiness in M&A isn’t a moment—it’s a mindset.

                Dear ChatGPT, please rephrase these bulletpoints into a chapter of my book: ...

                Pray tell why may we not just read the bulletpoints instead?

                Sold your own company, but unable to use your own words?

                  • HPsquared

                    today at 5:25 PM

                    When I see "it's not X, it's Y" I think of the music criticism of P. Bateman: "...it's not just about the pleasures of conformity and the importance of trends, it's also a personal statement about the band itself. Hey, Paul..."

                    • mojuba

                      today at 5:52 PM

                      So the market is going to be flooded with this type of soulless books that have no distinct character or style, just pure dry facts?

                      In a sense, "I wrote a book about it" is disingenuous and I agree the author's bullet list would probably be more interesting and would save us a lot of time.

                        • zhyan7109

                          today at 7:39 PM

                          Good feedback, thanks! Will include a version of the original stream of conscience and raw note in a day or two

                            • nubg

                              today at 7:59 PM

                              I would take back my negative feedback in that case! Am reading the book, content is interesting, but I am never sure what is actually your thought vs LLM fillers!

                          • bpicolo

                            today at 8:02 PM

                            Going to be? Already is!

                    • einarvollset

                      last Wednesday at 8:58 PM

                      Great content and perspective. I would say (and fair warning, this is obviously biased as I run one of the investment banks that specialize in B2B SaaS M&A between $2-20M ARR - Discretion Capital), this:

                      "Now should you hire a banker when there is no actionable inbound interest and you have no prior relationships? I would recommend no, as in such a case bankers would typically rely on their network of Corp Devs and present your company to a laundry list of potential companies that likely have nothing to do with your space or business or you have no interest working for."

                      ..is not how a great banker that actually does deals in the revenue size and market you're in would act. I can see how a "too large" a bank where you're small fry, would do this, but eg in my space ($2-20M ARR), the key job of your banker is to reach out to whomever would pay the most for your business, not just their corp dev buddies they happen to have existing relationships with.

                      That's not easy - there are 1000+ repeat software buyers with various portfolios and all kinds of timing constraints, and that's even before considering true strategics (in my range, the buyer mix is 70% PE or PE owned, 20% strategics and 10% other).

                      Typically, for a proper process, you'd want to see 100-150 (well sourced and properly targeted) potential acquirers. If they're just sending you to a handful of corp devs then they're not taking your business seriously and you should get another banker.

                        • Eridrus

                          today at 6:10 PM

                          What does it take to get a good outcome in the 2-20m ARR exit space?

                          When I read PE multiples in the 3-5x ARR range, it seems like a fire sale compared to valuation prices. At 3x, you might just be giving it all back in liquidation preferences.

                          Am I missing something, or is this just founders who are sick of running the business and want to do something else, or are there lots of capital efficient companies in this range where 3-5x revenue is a good deal?

                          • zhyan7109

                            today at 5:56 AM

                            Thanks for that perspective, Einar.

                            I agree that good bankers are hard to come by and unfortunately most simply forward decks to a broad list, and they won’t get founders the outcome they deserve. My point was more about readiness for a sale. Having gone through it, I’ve come to believe there are certain prerequisites for even kicking off a process, primarily business fundamentals and pre-existing relationships.

                            In my experience, a banker can amplify an existing market, but they can’t create one from scratch (at least not easily).

                            For example, in our case we had roughly six serious inbound inquiries before engaging bankers. While our bankers (and they are great) ran a broad discovery process and put us in front of many potential acquirers, the eventual buyer was one that reached out to us unsolicitedly rather than being introduced through the process.

                            • dangero

                              today at 3:50 PM

                              The problem I’ve heard about small deals is that the bankers want a larger percentage. Can you comment on that aspect?

                                • zhyan7109

                                  today at 7:39 PM

                                  Depends on who you talk to, 3-5% of total deal size plus a retainer is the norm

                          • oneneptune

                            today at 8:59 PM

                            Nice, you fed bullet points into the LLM to make a book. I can stuff your book into an LLM to make bullet points. It's like a wonky non-deterministic hash for both of us to save time and give the author some feel good dopamine at the expense of tokens + authenticity!

                            • chilipepperhott

                              today at 8:36 PM

                              Frankly, it's insulting enough when someone sends me copypasta from ChatGPT in the form of an email. It's even more so when it's a whole book.

                              • jasonshen

                                today at 2:25 PM

                                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!

                                  • Eridrus

                                    today at 6:47 PM

                                    What makes you think this was a 9 figure deal?

                                    This smells more like a $10-20m deal based on what I could find about his company. I could obviously be wrong, but 100 seems like a real stretch.

                                    • pieterhg

                                      today at 4:20 PM

                                      What was the sales price? $100,000,000?

                                        • zhyan7109

                                          today at 7:40 PM

                                          haha sorry this info is under NDA

                                  • tiffanyh

                                    today at 3:58 PM

                                    In case it help others (since it wasn’t apparent to me) … this is about Pixieset acquiring Polarr

                                    • mvkel

                                      today at 8:11 PM

                                      "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.

                                      • nerdsniper

                                        today at 3:22 PM

                                        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.

                                      • jacob_rezi

                                        today at 2:01 PM

                                        Any place to download as a PDF? I think this might be a timely resource

                                          • mrskitch

                                            today at 6:40 PM

                                            I enjoyed reading the first few chapters, but wanted a PDF as well. I run browserless.io, so threw a quick script together to PDF-ify this. Gist is here: https://gist.github.com/joelgriffith/0e6a2a774317e845206ca8d....

                                            You can pretty much just create a free plan and run this in our debugger, which will compile the chapters and return PDF. Pretty fun little challenge.

                                            • sebastiennight

                                              today at 5:38 PM

                                              So... the book is released under a Creative Commons license that does not authorize sharing derived works...

                                              BUT...

                                              If you use this tool I just vibe-coded with our good friend Claude: https://onetake-ai.github.io/html-ebooks/

                                              And point it at the repository: https://github.com/yan7109/yan7109.github.io/tree/main/ma-bo...

                                              It will give you an ePub with all the chapters, including a bit of styling etc.

                                              The code is MIT licensed, so do with it as you wish.

                                                • mck-

                                                  today at 7:21 PM

                                                  Thank you! This was very helpful :)

                                              • zhyan7109

                                                today at 7:40 PM

                                                Good feedback, I’ll add one later tonight

                                                • krater23

                                                  today at 2:15 PM

                                                  just download with curl as html

                                                    • Centrino

                                                      today at 2:34 PM

                                                      This may help: https://github.com/yan7109/yan7109.github.io/tree/main/ma-bo...

                                                      Though I'd rather download a PDF or ePub.

                                                      I would say that the current format is a 'book' in content, but not a 'book' nor an 'e-book' in form, as you can't manipulate it as a single object. But I've seen a few other examples here on HN where people showed off a 'book' purely as a website.

                                                        • sebastiennight

                                                          today at 6:02 PM

                                                          As I shared in a comment above, the book is released under a Creative Commons license that does not authorize sharing derived works so only the original author can distribute you an alternative version

                                                          However I vibe-coded this tool for my personal use with our good friend Claude: https://onetake-ai.github.io/html-ebooks/

                                                          Which when pointed at a repository containing an "html book", like https://github.com/yan7109/yan7109.github.io/tree/main/ma-bo...

                                                          will give you an ePub with all the content in one place.

                                                      • foolswisdom

                                                        today at 2:34 PM

                                                        It's not a single page.

                                                • today at 3:11 PM

                                                  • DEDLINE

                                                    today at 7:45 PM

                                                    This is really, really good. I can’t stop reading it. Thank you for writing this.

                                                    • mrandish

                                                      today at 6:50 PM

                                                      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 that easily could have blown up. The difference probably came down to some good luck at the right moment, which isn't a great feeling in retrospect.

                                                      • riazrizvi

                                                        today at 5:39 PM

                                                        Wow. There's some very useful information for me here. I like chapters 5,13,21. Thanks for sharing.

                                                          • zhyan7109

                                                            today at 7:43 PM

                                                            Glad some chapters are helpful, thanks!

                                                        • tomik99

                                                          today at 5:22 PM

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