I don't know the specifics of your company so I can't give you valuation advice, but I'd just like to add that, in my experience, I've seen lots of C-level teams and Directors refuse to sell even when a great offer was on the table because they believed they were worth more. In numerous cases, it turns out they were wrong and the company either fizzled out or sold to a different buyer a year or two later for much less than they could have gotten.
I'm talking refusing a $3.5 billion offer because you think you're worth $4B, only to sell for $2B later.
Not every deal is a good deal, but remember as an insider who's built the company you're also likely somewhat biased. There's nothing morally wrong about selling if it is quote-unquote "the right price".
I can't really name names in public, but email is in profile if you ever want to chat
Check out the earlier posts in the series. They’re probably more relevant for that stage. What I’ve learned over the years is that the CTO role varies a lot depending on the company and personal context. I just tried to share my journey.
Thanks for your message and point of view. You’re probably the only person here who has been presented with a similar scenario, and this is exactly how I felt.
I won’t disclose details out of respect for the other party, but no, not necessarily. As I wrote, it was a good deal for the founders and some investors, but not for everyone, including employees. There are many ways to structure a sale, and unfortunately not all of them split the cake equally.
Hard disagree. Culture isn’t the problem, org structure is. You can call it an experiment or even a hack. Every team is already innovating within their scope, and splitting becomes easier as that scope grows.
What is too much is asking an Engineering Manager to start a completely independent product line that may go nowhere. It’s far more effective to rely on senior, staff+ engineers who don’t need management and have experience taking things from 0 to 1. They can build an MVP quick. Once we see real signals of PMF, we can then build a team around it (or drop it)
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.
2. Confiding with your spouse with clear concerns about current levels of stress and time commitment.
3. We can resolve a lot of the stress and sustainability problems by (among other things) raising another funding round!?
I did a double take…isn’t that just inviting more stress, more pressure from investors, more expectation to grow and exit?
I find it hard to relate to this C-suite life and logic, it seems so hyper-capitalist and backwards. There are so many oddly revealing bits of this piece that are like a window into the world of an alien being compared to my perspective.
It’s like Star Trek where there’s an alien race for every personality type and/or representation of a dominant emotion. The C-suite aliens would build their society around building products, meeting customers, finding takeaways, making org changes, etc. Societal
enjoyment comes from work accomplishments, and the family decides that stress and time apart is worth it because work is “your baby.” Not really quite like the Ferengi because the Ferengi would have taken the 9 figure exit and dumped it into the next scheme.
Meanwhile the viewer is most familiar with the even-keeled baseline of the Federation where they used their technology to end capitalism and spend their time exploring the galaxy and prioritizing their family and friends. You end the episode with “I’m glad I kept an open mind but I still wouldn’t want to be the C-suite aliens, I like hanging out with the Federation.”
Maybe we are wired differently, but as I wrote in the final part, I’m actually more motivated and see myself going much longer (which is what investors want, as long as there’s growth). It’s linked in the post, but a big part of the round was secondary, which helped reduce financial stress for founders and early employees.
Yes, wired very differently. I think that’s why I used the Star Trek analogy.
This motivation is like a strange curiosity to me. This pursuit of product is so foreign to me, and from the outside it doesn’t seem healthy. But I guess if the Klingon like going into glorious battles to the death better than chilling at home with their family, who am I to question their motivation?
I build stuff at work because it’s a financial obligation, because it’s better than cleaning bathrooms or waiting tables for a living. If I had some kind of better option for paying my bills with less labor involved I’d take it in a heartbeat.
I felt the same as you - turned down several acquisition offers, the company was my baby, etc.
Year ten, my partner turned around and stuck a knife in my back, and I found myself railroaded out and battered into submission by lawyers. Exited with token equity, and a small cash payment to get me to fuck off so they could gut the company.
Retrospectively, I should have quit while I was ahead, and I should have realised that while I cared about the company, it did not care about me.
Also, cofounders… you never find out who they actually are until one night you hear the click of the hammer of the gun against your head cocking.
raising the round is them selling part of the company. enough of the company that they no longer ever have to worry about money again. yeah that removes a lot of potential stress. the company can fail now and it won't ruin him. gives him more freedom to keep building.
This is the disconnect to me. This phrase has tech industry cult vibes to me.
I don’t see “freedom” and “building” as words that mesh together.
I see “building” as something I’m obligated to do to pay my bills. I do it because it’s preferable to other forms of labor. As soon as I have the financial means to stop doing it, I’m out.
Hardly a cult. So you don't like building things. Fine. Nothing wrong with that. Plenty of folks, however, do love building things. When I dream of freedom unlocked by money I love the idea of building things still; the difference is building what I want, how I want it, without being trapped.
There’s a big difference between “building things for fun and accomplishment” and taking on the intense obligations of continuing to be a CTO when a major exit is on the table.
I totally understand that there are people who relish in the challenge, feeling needed and important to their team, and the prestige and visibility, but I don’t really understand what their brains are doing and what.
OP talked about the luxury of being able to fly out the grandparents to help out taking care of the kids when things get busy at work. That doesn’t sound like freedom to me.
Agreed on having the flexibility. I think that's the key, the self awareness and ability to adapt. I don't think having CEO/CTO/CMO for founders is a bad idea though. Even at Cloudflare, CEO and COO were co-founders. I am more curious about what it takes to grow from a founder CTO to a public company CTO, same way than other founder roles can. Or maybe it's just too hard.
Anyway, I am flexible John! Totally onboard to give up my title if you are interested to come over and help us RevenueCat go public ;)
Hi! I could tell you that we were visionaries and we knew a pandemic was going to come, so we were super prepared, but that would not be true.
In the early days, Jacob and I discussed a lot whether we wanted to be a remote company or not. We were very attracted to the idea, and firmly believed it was the future. But as you mentioned, we were concerned about the ability to move fast and setting the culture. The first employees we hired from our network were actually based in SF, so it was not a problem.
One of the early employees wanted to move back to his hometown, and we started to move to a more remote first environment (eg more async comms, everyone using their own cam for meetings even if they were in the office, etc). We hired our first engineer remotely (who we had the pleasure to work with in the past) and we never looked back.
It's been challenging (communication, compliance,...). But overall, we are super happy. I have a strong network in Spain and the UK, and we have access to world class talent that do not necessarily want/can live in the Bay Area. Also no immigration issues!
Even Jacob, my co-founder and CEO left the Bay Area. Being prepared was extremely helpful when the pandemic hit, since most processes were already in place.
Important note, we DID NOT do it for financial reasons. We pay same salary (based on SF) no matter where you live in the world.
