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

derekyan.com

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

#61

Post by prawn »

nubg wrote: post #15

> 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?

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.

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

#62

Post by einarvollset »

Eridrus wrote: post #24
einarvollset wrote: post #2

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 p…

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 r…

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.

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

#63

Post by einarvollset »

zhyan7109 wrote: post #3
einarvollset wrote: post #2

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 p…

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 m…

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

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

#64

Post by einarvollset »

zhyan7109 wrote: post #34
dangero wrote: post #11

Earlier quoted context omitted.

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%

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

#65

Post by Eridrus »

einarvollset wrote: post #62
Eridrus wrote: post #24

Earlier quoted context omitted.

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 r…

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 successfu…

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

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

#66

Post by greazy »

gbnwl wrote: 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…

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.

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

#67

Post by zhyan7109 »

nubg wrote: post #41
zhyan7109 wrote: post #33

Earlier quoted context omitted.

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...

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

#69

Post by swyx »

tiffanyh wrote: post #12

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.

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

#70

Post by rrr_oh_man »

greazy wrote: post #66
gbnwl wrote: 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…

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.

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