[HN Gopher] Show HN: It took 4 years to sell my startup. I wrote...
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Show HN: It took 4 years to sell my startup. I wrote a book about
it
Author : zhyan7109
Score : 178 points
Date : 2026-02-04 16:56 UTC (4 days ago)
(HTM) web link (derekyan.com)
(TXT) w3m dump (derekyan.com)
| einarvollset wrote:
| 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.
| zhyan7109 wrote:
| 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 wrote:
| The problem I've heard about small deals is that the bankers
| want a larger percentage. Can you comment on that aspect?
| zhyan7109 wrote:
| Depends on who you talk to, 3-5% of total deal size plus a
| retainer is the norm
| Eridrus wrote:
| 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?
| jacob_rezi wrote:
| Any place to download as a PDF? I think this might be a timely
| resource
| krater23 wrote:
| just download with curl as html
| foolswisdom wrote:
| It's not a single page.
| Centrino wrote:
| 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 wrote:
| 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.
| sebastiennight wrote:
| 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- wrote:
| Thank you! This was very helpful :)
| mrskitch wrote:
| 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/joelgriffit
| h/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.
| zhyan7109 wrote:
| Good feedback, I'll add one later tonight
| jasonshen wrote:
| 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!
| pieterhg wrote:
| What was the sales price? $100,000,000?
| zhyan7109 wrote:
| haha sorry this info is under NDA
| Eridrus wrote:
| 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.
| nerdsniper wrote:
| 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.
| dewey wrote:
| I enjoyed this book: https://zerotosold.com/
| tiffanyh wrote:
| In case it help others (since it wasn't apparent to me) ... this
| is about Pixieset acquiring Polarr
| nubg wrote:
| > 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 wrote:
| 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 wrote:
| 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 wrote:
| Good feedback, thanks! Will include a version of the original
| stream of conscience and raw note in a day or two
| nubg wrote:
| 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 wrote:
| Going to be? Already is!
| gbnwl wrote:
| 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 wrote:
| > 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.
| Eridrus wrote:
| 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 wrote:
| OP here, 83b didn't apply in my case as I had only stick
| options, referenced in chapter 11
| Eridrus wrote:
| 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"
| neilk wrote:
| 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 wrote:
| 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 wrote:
| 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 wrote:
| 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.
| pryelluw wrote:
| 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
| Klaus23 wrote:
| 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.
| malshe wrote:
| If it is only to fix grammar and improve conciseness, I find
| grammarly quite useful. AI goes way beyond these things.
| Also, while making something concise, AI might make things
| more difficult for the readers to understand. Worse, it might
| write something that is totally wrong.
| unyttigfjelltol wrote:
| The workflow is fine, the content is fine. The LLM needs to
| lean in a little harder on your voice and condensing your
| content-- focus on subtraction rather than addition.
|
| The problem is: viewed as a one-off, it's a gem. But put it
| on the AI slop conveyor many commenters here apparently are
| fed all day long, the voice is too similar, it seems like
| another chapter in _that_ anthology.
| riazrizvi wrote:
| Wow. There's some very useful information for me here. I like
| chapters 5,13,21. Thanks for sharing.
| zhyan7109 wrote:
| Glad some chapters are helpful, thanks!
| mrandish wrote:
| 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.
| DEDLINE wrote:
| This is really, really good. I can't stop reading it. Thank you
| for writing this.
| mvkel wrote:
| "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.
| chilipepperhott wrote:
| 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.
| oneneptune wrote:
| 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!
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(page generated 2026-02-08 23:00 UTC)