Just a quick professional update.
After 3.5 years of a crash course in venture-backed startups, I’m moving away to do new things.
I’ve personally built 4-5 products (depending on how you count it) at Flyflow over the past year. No hard feelings on my end and wishing the team well. The most likely outcome is that we stay friends in some way, people I’ve known for years. Just wasn’t the right fit for me. I left (wasn’t fired). I think they’re going to keep going without me, and I’m a small equity holder. Bopped around and experimented with joining another startup, before realizing that right now for me that path isn’t the right thing. Left both things in a way that was clean and respectful to both founders and investors - one thing that is often hard but I’ve learned to do decently.
If you do startups enough, you’ll realize they’re intense, not even with work hours etc, but with also how emotionally involved you get. I have actually slept in the office (not a ton, but a bit) and worked every weekend and night for the past three years. It wasn’t for money, I just love it. Also when you go the venture backed route you are essentially taking the highest-risk path. I don’t think I’m in a place to make that level of emotional investment again (at least in the short term), so I’m moving onto new and bigger things.
What’s Next
First thing I had to do was just emotionally decompress from the past month or so - there was some intensity. I’ve taken a couple of weeks just to chill, drove to Colorado and have been hanging with friends and family.
Now I’m thinking about what’s next. It’s part of my personality to be actively writing code and shipping. It’s probably not a good thing for me to stay away from that for too long. I can be thoughtful about how I do it though, not going to jump into something super committal right away.
Just for first time readers / people that don’t know me super well. I’m a staff / senior staff (in big company terms) level engineer. I have a lot of startup experience. Built many at-scale products (serving 100m+ users and moving $1T+ / yr in both crypto and fiat, no exaggeration). Have been CEO and CTO of various venture-backed things. Raised $5m+ (did all of the fundraising myself). I’ve worked at several venture funds and funds of funds including Coinbase Ventures where I was one of the core investment team members. Managed small teams up to 10 engineers and non technical folks. Seen companies from the earliest stages through scaleup through IPO. I’m a YC founder (lower acceptance rate than Harvard). I actively angel invest and have done about 30 deals over the past three years. I’m someone who is capable of notching massive wins, and I have also lived through some pretty big losses too. I think through all of the life experience I have gotten quite good at handling messy situations and navigating them towards positive outcomes. Most of all, I just love building.
The first thing I’m doing is starting a consultancy / holding company.
For the consulting piece I plan on offering high-end engineering consulting services to many growth stage companies. Probably starting lighter workload while I’m on a bit of a break, but being able to flex it up. Depends on the company stage (will flex earlier stage if necessary), but will take a mix of cash and equity. Doing it through an LLC for tax advantages and ability to scale it.
The holding company part is split into two parts: wrapping my angel investments into an entity and a portfolio of software projects that are not meant to be venture backed but I can scale and sell as necessary.
Second, slowly and opportunistically I’m looking at more full-time opportunities. I have had a few startups reach out (including some very well funded ones). Unless something *insanely* good comes along, I’m probably looking more at an engineering leadership role at a very well funded and growing scaleup. I don’t want to go to a public company because I don’t see the personal growth opportunities as the same. I’m engaging with recruiters (a few have reached out already). I think a “fair“ leveling of my skills is probably somewhere between staff and senior staff. I’d like to take the IC track. I’m a good manager, but don’t think it’s my zone of genius (although I still love the mentorship and leadership component of IC work). Goal would be a director level person in 2-3 years. If this is your company or a company you recruit for, you can drop me a line at carl@carlcortright.com .