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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.

>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.

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.

LLM writing reads like shitty blogs turned into books. I'm not sure what this is called, but when the chapter can be summed up in a sentence or two, but fleshed out to cover 3 or four pages, with multiple anecdotes conveying the same concept.

> I'm not sure what this is called, but when the chapter can be summed up in a sentence or two, but fleshed out to cover 3 or four pages, with multiple anecdotes conveying the same concept.

This is how I felt when I read Tony Robbins. Or a modern business book.

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.

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.

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.

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.

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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..."

Writer: AI, please flesh out these bullet points into a business book.

Reader: AI, please summarise this business book into a set of quick-to-read bullet points.

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!

raw manuscript text here: https://derekyan.com/manuscript/Obsolete%20-%20The%20Secrets...

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?

So transaction multiples for us tend to be 5-8x (higher over $10M ARR), with outliers to 15-20x+

But the bigger issue is what you’re alluding to - lots of founders don’t really understand what doors they’re closing when raising a shit ton of cash. If you’ve raised $100M and are worth $50M, not a lot of good outcomes come easily (though I have helped a couple of founders navigate those waters too. Not always successfully)

Fact is - there are many more $50-200M outcomes than $1bn outcomes and if you’ve raised yourself into a corner where you don’t make any money unless you hit $1bn, well then better hope you took some secondary during fundraising.

The disconnect between these and venture multiples is still kinda crazy. Selling secondaries looks quite attractive in comparison.

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.

Yep couldn’t agree more that prep is important. And yeah often someone coming inbound is the most keen (though they still need managing to get the biggest outcome in my experience).

I’m actually working on a “Definitive Guide to M&A to B2B SaaS between $2-20M ARR” (first few chapters on discretioncapital.com/guide), would love your feedback on the draft of the rest given your experience. Email me if you want to take a look: einar@discretioncapital.com

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

Yep. More the smaller the deal. Sub $1M ARR, it can be 10-20%

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.

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

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

saved you a claude:

Polarr's Mission: For over a decade, Polarr has provided photographers with intelligent, intuitive AI-powered tools for photo and video editing, culling, and workflow automation. The company pioneered web and mobile photo editing apps and powered photo enhancements on hundreds of millions of devices through edge AI SDKs. Pixieset is a Vancouver-based all-in-one SaaS platform serving over 600,000 photographers with client galleries, websites, and online stores. Polarr is a San Jose-based startup that has built a community of creators with AI-powered editing tools and a catalog of over 1 million filters generated monthly. 1

Founding & Early Years

Polarr was founded in 2014 by Stanford graduate Borui Wang and Derek Yan. The company launched its online photo editor in February 2015. The app achieved remarkable early traction, receiving 250,000 downloads in its first 48 hours.

Product Evolution

• June 2015: First mobile version of Polarr Photo Editor released

• Fall 2015: Launched Polarr Photo Editors for Windows 10 and macOS

Polarr was named Apple's Best of the App Store for 2015 and 2016.

• December 2017: Released Album+, an app using on-device AI to organize photos

• March 2019: Announced $11.5M Series A funding round led by Threshold Ventures. Other Investors: Threshold Ventures, Cota Capital, Pear VC, StartX, and ZhenFund

• April 2022: Launched Polarr 24FPS app for video editing with Polarr filters

• January 2023: Launched Polarr Next, an AI web app that learns user style for automatic photo updates

• 2023: Introduced Polarr AI Copilots (beta) for transforming text into photos, videos, and designs

Public revenue figures for Polarr are not disclosed. However, the company demonstrated strong early traction: • 4 million Monthly Active Users (MAUs) as of 2019, with only 30% based in the US • Enterprise partnerships with major OEMs including Samsung, LG, Oppo, and Lenovo, whose native camera apps integrated Polarr's technology • Enterprise value estimated at $46–69M as of recent valuation data

The company operates a freemium model with premium subscription tiers ($2.39/month for filter storage and premium filters, $4.79/month for all features), but specific ARR or annual revenue figures have not been publicly released.

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...

I enjoyed this book: https://zerotosold.com/

"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).

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."

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

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 :)

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.

Good feedback, I’ll add one later tonight

pdf link added at the bottom of the page

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.

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.

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 :)

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!

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

thanks for support!

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.

4 years thats a lot

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