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My role as a founder-CTO: year 8

141 pointsby ridruejolast Friday at 7:43 PM113 commentsview on HN

Comments

ceberttoday at 12:25 AM

I’m a big fan of the idea of an Office of the CTO group reporting directly to the CTO that helps with prototyping greenfield projects and exploring innovative ideas. I believe a group like this would be beneficial for larger organizations, like the one I work in. There are numerous opportunities for market disruption, but it becomes increasingly challenging to make bold bets as the company expands. If I had the power to do so, I’d set this up at my company asap.

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throw03172019yesterday at 11:25 PM

I’m curious what kind of secondary sale happened? What is normal these days? Is it $5m $10m? Is that excluded from the $50m raised or comes out of that amount. Thanks!

orliesaurusyesterday at 8:48 PM

The wild part to me isn’t 9 figures is good/bad, it’s that in year 8 the company still has a single human as the default DRI for culture, zero‑to‑one work, and existential decisions. If you’re going to turn down generational wealth, the least responsible version is keeping everything psychologically and operationally coupled to you; the grown‑up move is making yourself cheap to replace and designing a succession plan you’d actually be willing to trigger on bad news, not just a term sheet

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Sparkytetoday at 6:03 AM

I kind of want to be a CTO somewhere. So much bureaucratic stuff to become one though. You usually have to be someone's friend or start a company yourself.

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ezekgyesterday at 10:23 PM

Good read. I had an offer for a mere 7 figures and that was hard enough to turn down. I couldn't imagine 9 figures! But I think I do get it, at least as much as I can get it at my level. It's hard to give up something you've poured so much of your life into -- "your baby." You lose the autonomy to continue shaping what independence looks like for yourself, or at least it felt that way to me.

IncreasePostsyesterday at 10:33 PM

Unless he's pulling a lot of cash out every year it seems unwise to not sell. He can then just go create something highly similar, bankroll it as much as he wants, but still have the back stop of vast wealth on case of failure.

fourseventyyesterday at 7:33 PM

Unless you are already worth billions if an exit would net you 9 figures its a no-brainer to sell.

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harmonic18374yesterday at 9:20 PM

I feel RevenueCat is on shaky ground, their market position can only get worse and worse as Apple and Google improve their complimentary offerings and they are forced into more A/B testing that directly competes with others. Recent StoreKit changes this year close a lot of the remaining gap. I would have sold. I wonder why they chose not to.

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throw03172019yesterday at 9:49 PM

I’d take the money, spend time with family (he mentioned toddler) and then figure out what to do next. Retiring isn’t everyone’s dream but at least having generational wealth is a big relief.

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lizknopeyesterday at 9:28 PM

I had never heard of the company RevenueCat. It looks like a system for mobile app developers to make in app purchases. A few Internet sources say that RevenueCat has about 120 employees. I'm in a completely different field so I'm not going to claim to understand all of that but I have worked for 2 startups.

The author talks about himself and his co-founder Jacob and they went back and forth on whether to sell or not.

I am very interested in what the other 118 employees thought. Did they want the co-founders to sell? What was their equity in the company? What kind of deal would they get? Accelerated vesting? Much larger than normal RSU stock grant at the acquiring company compared to a normal new hire there? Nothing?

I post this link in many threads about startups about how the normal employees often get nothing. The author says "So we decided to raise another round" and I wonder if the co-founders share the liquidation preferences and captables with the other 118 employees.

https://www.reddit.com/r/startups/comments/a8f6xz/why_didnt_...

I posted this comment in a different startup related thread last month but I really wish the CEOs of both startups would have accepted these lower offers.

I don't know what the captable was at the first startup but at the second I would have got around $300K. This would have been a large amount of money for me but the founders wanted more so they rejected the offer.

Almost every "normal" level employee thought we should have taken the deal and then we would have also gotten jobs with normal RSU grants and bonuses at the acquiring company which was a well established company.

It made me decide to never work at a startup again. I don't want a single person to be able to control my financial situation that much. I'd rather have the relatively guaranteed yearly raise, bonus, and RSU grant, and not have to drink the Kool-Aid of the founders.

> I worked at 2 startups. Both failed.

> The first had been around for about 4 years when I joined and had products that made money. They were trying to get acquired. They had partnered with 2 companies making products specifically for them. One of them offered to buy the company for $30 million but the founders thought their company was worth $300 million. They said no and then money started to run out and people started leaving. In the end the assets were sold for $2 million.

> The second startup was created by former coworkers and I joined after it had existed for 4 months. We worked like crazy for the first year and got our prototype out. We had a lot of interest but it took me a while to realize that the 3 founders already had net worths from $5 million to billionaire level. When I heard about offers in the $30 million range they just weren't interested in selling for so little. I left after 3 years and the company floundered another 2 years until they shut it down as people left.

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OGEnthusiastyesterday at 8:44 PM

Not taking a nine-figure exit is insane to me.

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adiazyctoday at 1:38 AM

[dead]

cityzenyesterday at 8:43 PM

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weslleyskahyesterday at 8:48 PM

Why this industry has such a claustrophobic atmosphere? If he was a doctor and had a calling for the profession, I would understand. I was doing an unrelated degree (Econ), but now I am doing a tech degree and I never saw such a depressive mentality towards life among peers.

It is like these people are hell bound to the work culture, diehard workaholics. They don't know anything else outside of a computer screen.

Honestly disgracefully.

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farceSpheruleyesterday at 7:35 PM

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farceSpheruleyesterday at 7:41 PM

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raw_anon_1111yesterday at 7:22 PM

Saying you want to control your company and you want to be around 10 years and then raising VC funding is either naive or dishonest.

VCs aren’t interested in a lifestyle business throwing them maybe a small dividend and a miniscule number of companies go public. Look at YC, they have invested in thousands of companies and only around 20 have gone public and only 3 have had positive returns since going public

https://medium.com/@Arakunrin/the-post-ipo-performance-of-y-...

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