My role as a founder-CTO: year 8
miguelcarranza.es113 points by ridruejo 5 days ago
113 points by ridruejo 5 days ago
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.
If that group is necessary then it's a damning indictment of the product/engineering culture. The CTO's job should be to fix the broken culture, not try to side-step it.
Not every company is a product/engineering company.
A CTO is a common title at medium and larger law firms, and an office of the CTO for that org sounds like a great idea.
Shouldn't this live under the VP of Product?
That’s a good point. Perhaps where this group lives depends on your organization. Unfortunately, the innovative ideas aren’t necessarily coming from product where I work.
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!
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
That was the whole point of writing this series: to show how my role evolves and what I’ve had to give up. Trust me, if it were up to me, I’d still be having fun coding (even more so these days). There’s an entire section on delegation in this year’s post.
I’m not the single DRI for culture at all. We have many strong culture carriers, which has made scaling to 100 people much easier than scaling to 20. That said, culture is still one of the core responsibilities of founders, in my opinion.
Also, OCTO isn’t about me wanting to innovate. It’s about giving certain engineers permission to not be tied to a roadmap and to stay fluid.
That's never quite how it happens, they can't let go. You can see it in the "Office of the CTO" thing. I've seen that one many times before: when confronted with the endless complexity and depth of building a real global product, they recoil. Everything takes too long, is too uninteresting. They instead build up this parallel engineering organization that is showered with money, headcount and C-level attention to build the new moonshots, with the subtext that whenever it's "ready", it will be thrown over the wall to the actual engineering org. It's a speedrun to make your engineering talent leave.
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.
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.
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.
Unless you are already worth billions if an exit would net you 9 figures its a no-brainer to sell.
almost: just cut a deal to allow partial liquidity, ideally via a vehicle that avoids tax events, e.g. loan
Is it? So you can what? Buy exotic vehicles? Buy extra houses? Buy surgeries? Buy expensive experiences?
All you find is stuff, presented as super valuable, and people very very keen to sell it to you. They’ll do whatever you want. It attracts a certain kind of person. The people who have the means for this lifestyle seem mostly disappointed.
It’s not the situation this guy has created for himself. His life has meaning, he’s of value to his employees and customers and partners.
So that you have security for the rest of your life and your children have security for the rest of theirs. And likely their children as well.
Not everthing bought with money is superficial. Certainly a lot is less superficial than dedicating your life to “in app payments made easy”. Turning down generational wealth so you can continue to pursue your dream of being a tech CEO seems like a wildly selfish decision to me. Just start a new company!
I know from the outside this seems very simple, but it's more complicated than that. Certainly, if the objective is (merely) security for one's children, that can be secured with much (much) less money (and likely was secured in the secondary that the author makes reference to); having nine figures of wealth is not an unvarnished good, and in particular makes raising grounded, self-reliant kids pretty complicated. To appreciate this dynamic, read Graeme Wood's outstanding 2011 piece in The Atlantic, "The Secret Fears of the Super-Rich"[0].
[0] https://web.archive.org/web/20190422235813/https://www.theat...
> having nine figures of wealth is not an unvarnished good, and in particular makes raising grounded, self-reliant kids pretty complicated
Sure, but I’m pretty sure if you asked those parents if they’d rather lose all their money to make parenting easier their answer would be a resounding “no”.
Those aren't the choices. You don't understand how the poster passed on nine figures -- but if the secondary sale netted 7 figures (likely), the choice is in fact between having enough wealth to have total security for one's family versus having so much wealth that the wealth itself creates anxiety.
Then have someone manage the money away from you. Put it in a lifetime trust, whatever. The idea that you’d turn down that sum of money because of the anxiety it would cause you is simply not logical.
Correct. The secondary provides the safety net to confidently swing for the fences.
You forgot to account for the 100+ employees. The liquidity event would have helped their families as well.
I just don't understand the mentality of the author. 9 figures is generational wealth, potentially perpetually with good multi-generational money management plan. With that kind of money invested, you have beaten the game, and can literally do any side quest you want to do, forever. This is the biggest no-brainer ever. What the fuck are you waiting for?
Similarly, I don't understand why the CxOs in my current (BigTech) company still work. You're done. You can do anything you want and yet you voluntarily continue to amass more?
> Similarly, I don't understand why the CxOs in my current (BigTech) company still work. You're done. You can do anything you want
Has it occurred to you that perhaps what they want is to be the CxO of a big tech company? There’s a lot of power, prestige, and impact on society that you can’t easily have if you quit. Maybe they really enjoy the work itself too.
Because it's genuinely not about the money for them. It's hard to believe, but some people really do want to make the world better in their way, with whatever tools they have that their disposal.
Companies do not make the world better.
The Kool Aid is strong, remember this is the forum of an incubator. One has to believe to drink the whole cup.
Anyone can have security by living very safely within their means, by learning how to be satisfied. What people really mean when they say what you are proposing, is “guarantee a certain future lifestyle”. But the appeal of future lifestyles depends on not obtaining them. Without an ability to be satisfied, acquisition is always disappointing. It’s why a pay raise in a job that doesn’t address your needs, loses its shine after a month or so.
As someone who has experienced family adversity in my life (health, disability) I couldn’t disagree with you more.
Things happen. Expensive things. The security to be able to afford expansive cancer care without worry, to pay for therapy and specialized schooling for your child… these are huge, huge things and they happen to you (or your children, or your children’s children) no matter what you do or don’t do. This isn’t just about being happy to be frugal.
Things happen, it’s true. And in the world there are many enterprises that spring up to present solutions as long as you fork over all your cash, and here in the USA, based on the market, that means lots and lots of cash.
That’s just a perspective on hardship, it’s not the only way. People deal with hardships with many many tools. My favorite tools are dignity, grace, courage, personal strength, and ingenuity. Money is another tool, yes, but it tends to prevent mastery of the others.
Elsewhere in the comments there was talk about legacy. You can give your kids a bank account, and the examples that you had money to pay off problems. Or you can give them something else through your example. I choose the latter.
With respect, those words feel very empty. Face the prospect of, say, chemotherapy you can’t afford or death. See how you feel about dignity and grace then.
So people who can't afford a broken system cannot afford dignity or grace? We should be ashamed we allow this kind of collective paranoia.
If he had children, the decision would have been influenced by that. So that was my first guess, he probably has no kids.
Will accept, I have no idea about his personal situation. Also feel the HN crowd may downvote my comment because it is not phrased correctly.
I’m sure there are many other more meaningful options, none of which start with the word “buy”.
> Is it? So you can what? Buy exotic vehicles? Buy extra houses? Buy surgeries? Buy expensive experiences?
Buy freedom to chose what to do with your life. I've never sold a company and netted 9 figures but i have been lucky enough to work for a hedge fund and make enough that I and my family can do what ever we want from the age of 30 onwards.
That is an incredible amount of freedom and one that I wish most people would have.
You seem to think only in materialistic ways.
But having enough money to not have to work again allows you to be a better and more available parent. To be able to provide your kids and nieces and nephews with schooling to put them apart from other kids.
Its not always about owning another home, Just knowing that my kids are set for life before they start their own lives in case something happens to me was enough for me.
Lots of us think of others before ourselves.
> Is it? So you can what? Buy exotic vehicles? Buy extra houses? Buy surgeries? Buy expensive experiences?
Regain your own time. As a former CTO who has recently exited, recovering my own time again is more valuable to me than the money (although the money means I can retain my own time going forward).
> His life has meaning, he’s of value to his employees and customers and partners.
Your work is not you and if you think that way, you're gonna be crushed when you come to retire. Even though I loved what I did for a career, it's better to do what you love for yourself, not "employees and customers and partners". Many people have other interests outside of building tech, but even if building tech is your only thing, exiting is a chance at starting something fresh and on your own terms.
You can live in the heart of San Francisco on $2k/mo, including rent. You don’t need to work 10hours a week as a software developer, to support that lifestyle.
I could fit a solar system in the gap between your two options of a) full time CTO or b) 9 figures to ‘win back your time’.
Personally I believe you’ve been operating on autopilot, and not designing your life to suit your own needs.
> Personally I believe you’ve been operating on autopilot, and not designing your life to suit your own needs.
You have no idea about me at all, so please don't insult me by thinking that you do.
Bro, what? $2k? I just double checked and everything available for less than $2k is awful if you care about, IDK, having a family, a pet, a kitchen, outdoor space, green space, not having to share everything, including peace and quiet, with a revolving cast of characters.
Not that these things are required to “live,” but I certainly am not interested in making these tradeoffs.
Nah see you live in a SRO in Chinatown and get all your meals at the Catholic mission.
Yes I exactly did that! Moved into an SRO on the edge of Chinatown. It's a nice tiny apartment, I'm on the edge of a mecca of affordable grocery stores, and I'm two blocks from my part-time job that gives me free-time to self-fund my software hustle. But there are other options. What's wrong with living with good people in a room share?
Finding good people to live with is a miracle and not a permanent one. All it took is one good roommate to decide he didn't need to take his antipsychotics anymore for me to never want a roommate again.
So enjoy your situation while the good times roll, no shade, but people have their own reasons to never consider living in an SRO besides mere materialism.
Fair point.
BTW I was originally searching for an SRO but I landed a 'micro-apartment' (I just double-checked terms), it has its own kitchen/bathroom. Had I stopped looking I wouldn't have found this great situation. Great enough that when I won a housing lottery the following month, for a nicer apartment at the same rate, I was content to give it up and let someone else receive it.
Do you have a family or people you need to take care of? Life is more than sustaining your own existence.
How are you living in SF on 2k/month? How many people sleep in the same room as you?
You must be fortunate to have a lived experience where the answer isn’t immediately (and obviously) financial security.
Also: plenty of meaning outside of running a SaaS. Hell, undergraduate research assistants probably contribute more to societal at large.
You're right, financial freedom is completely unfulfilling, instead it's really meaningful and impactful to be involved in a tech economy whose primary value has been in undermining democracy and social systems!
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.
The secondary provided that relief. Continuing to work on the company makes perfect sense if you enjoy it, which he clearly does (with the inescapable ups and downs of every start up of course).
I dunno man. A useful psychological trick in this scenario is to imagine you were on the other side of the transaction.
Say you have nine figures in your account. Would you push it all into this company to be able to have a fun job? Seems completely insane to me.
F You Money means you can spin up whatever projects you want for the rest of your life. Even if your dream job is worth $100m to you, is the delta between this job and your realistic best alternative really worth that much?
Speaking as a co-founder CTO, I believe there is a very insidious kind of attachment that forms when you’re dancing with burnout, and working on a successful company that you’ve built from the ground up.
“I want to leave a dent in the universe” I told myself. After 3 months in a hammock decompressing, I very quickly realized that there is more to life than work, and it’s really easy to find fulfillment building things if you get bored. But this viewpoint is really hard to hold onto when you’re buried in the day to day excitement of the job.
> Even if your dream job is worth $100m to you, is the delta between this job and your realistic best alternative really worth that much?
At least for me, regular financial decision making breaks down once the numbers are above a certain amount.
E.g. You won’t feel 10x better about a $100m windfall vs. a $10m windfall.
The best case scenario for a lot of founders is to do a secondary, cash out / de-risk, and keep on building.
That’s the route I took. Paired with obsessive focus on work/life balance, I don’t regret taking this route.
you can take the money... and then continue to work. Nothing says you have to retire- I would have taken the money and figured out what's next! Not to mention that hopefully you've given shared ownership with your other early employees, who can also then at least have the opportunity for their own liquidity event.
Honestly, I respect the commitment. It's almost certainly a bad decision, but a founder that can turn down a 9 figure exit at the tail end of a tech bubble he's right in the middle of, has a good chance at having the right mindset to build a great company and survive the collapse. There's a good chance he regrets this for the rest of his life, but you can't argue that he wasn't a true believer or is a sellout.
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.
Startups (businesses in general) are a game and the employees are resources.
Don’t take it so personally. I did once too.
If the employees think they know better, there’s nothing stopping them from starting their own businesses and destroying their boss.
> Don’t take it so personally. I did once too.
This is easier said than done.
The founders of many startups are extremely charismatic. They can get you to sacrifice your personal / family life and work long hours by dangling the big pay day in front of you.
The second startup I worked at let the first 8 employees buy into the company for Class A shares. These in theory were worth more than the Class B shares I was given. This later led to some marital issues when one guy invested $100K into the startup based on the founder taking everyone out to dinner and assuring the wives it was a great idea. Then 3 years later they have turned down 2 possible sales, no exit plan in site, and that $100K would have been useful for the children's tuition who are about to go to college.
I write these posts are warnings to people who get excited about the appeal of working for a startup.
So I would really love to hear the author talk about what his employees thought about turning down the deal and how much money they would have got.
Yeah, just don’t get emotionally invested in a chance of paying off your mortgage immediately. Don’t get your hopes up about materially bringing down your retirement age.
It isn’t reasonable to expect the founders to do an employee’s bidding when it comes to selling a company, but it is reasonable for the employees to feel emotionally invested.
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-...
The problem with that analysis is it ignores all the companies that exited through an acquisition rather than public markets.
If anything, it's an endorsement of M&A.
My “analysis” was the idea of a private company that seems to want to stay independent and control their own destrone like the author of the submission wants. There are only two ways to stay independent - stay private forever or go public.
Once you take outside funding, you really have no choice but an acquisition or go public. VCs don’t want to get tiny dividend checks. Even public shareholders will insist on a sale at the right price
Going public doesn't keep you independent, though, unless you were already the kind of unicorn that has enough pull to own a massive amount of shares and/or a special class of them
Isn’t that what I just said?
> Even public shareholders will insist on a sale at the right price
Yes, but that isn't all you said and it isn't even right.
Public shareholders generally don't insist on anything as they are dispersed. They may elect directors to the board, but that question gets into all sorts of dynamics about who actually really votes when annual meetings come around, board independence, activist shareholders and whatnot.
Put all of that aside and assume for a second that directors are a perfect representation of shareholder interests. Boards do not "insist on a sale". Instead, they may have the _fiduciary duty_ to consider bona fide acquisition offers and take the decision that maximizes shareholder value, triggered upon certain conditions (cf Revlon Duties)
How many times have the board refused a sell for the right amount of money.
That is not "insisting on a sale". Selling for the right amount of money is literally the right decision to make!
The entire submission is about someone who doesn’t want to be acquired even at “the right price”. You don’t have that option when you take outside investors.