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.
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.
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.
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.
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.
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.
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.
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.
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
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).
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"
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..."
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.
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!
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.
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?
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.
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!
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!
"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.
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.
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.
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
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.
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.
> 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.
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.
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.
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.
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.
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.
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.
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.
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
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).
OP here, 83b didn’t apply in my case as I had only stick options, referenced in chapter 11
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"
> 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?
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..."
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.
Good feedback, thanks! Will include a version of the original stream of conscience and raw note in a day or two
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!
Going to be? Already is!
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.
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?
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.
The problem I’ve heard about small deals is that the bankers want a larger percentage. Can you comment on that aspect?
Depends on who you talk to, 3-5% of total deal size plus a retainer is the norm
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!
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!
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.
What was the sales price? $100,000,000?
haha sorry this info is under NDA
In case it help others (since it wasn’t apparent to me) … this is about Pixieset acquiring Polarr
"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.
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.
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.
I enjoyed this book: https://zerotosold.com/
Any place to download as a PDF? I think this might be a timely resource
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.
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.
Thank you! This was very helpful :)
Good feedback, I’ll add one later tonight
just download with curl as html
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.
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.
It's not a single page.
This is really, really good. I can’t stop reading it. Thank you for writing this.
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.
Wow. There's some very useful information for me here. I like chapters 5,13,21. Thanks for sharing.
Glad some chapters are helpful, thanks!