Exited with two co-founders when our runway ran out. Sold our IP and assets for a modest amount to our main competitor.<p>I realised that (as CTO) the main area I couldn't contribute to was 'the business' of running a successful company. So I decided to remedy that, I joined McKinsey and left last year as an Associate Partner. I'm now the VP Engineering at a fast growing tech company (250+ people) and the impact I can have with technology is an order of magnitude greater than before because of the intervening experience
Sold last year (2 founders) to a very focused private equity fund from a weak position - We were bootstrapped and profitable but large competitors entered the space and we were slowly losing the battle.<p>From financial perspective it was personally a good deal. Now have a 3-year non-compete for a specific field. The new owner is doing well with a larger team, resources and synergies between their other investments.<p>One aspect that's not very often covered is the psychological side which was very hard for me. Soon after closing and moving forward, I absolutely felt lost, more than ever before - Kind of lost my purpose? No customers to care about, weaker connection with earlier team mates and professional friends from the industry, a lot of free time and no hecticness I used to have.<p>Started working on something new, validated and built the 1st version of the product, got very light traction but didn't find a profitable model for it. Had investment offers on table to get funded but declined as we were not confident about the business case.<p>Now investing slowly, doing the things I like more intensively (skiing & climbing) and trying to understand what would the next professional/entrepreneurial step be and what I want in life.
I sold my 10 year old company about a year ago and promoted my #2 to CEO to lead it post acquisition. Aside from the company related responsibilities I still have here's what I've been doing:<p>-Actively working to strip away the identity/persona I built up over the last decade while leading the company, in order to get back to "who I really am and/or accurately understand who I've become" outside of the context of the company and the role of CEO/Founder.<p>-Reading SO MUCH. And specifically the book "The Adult Years" has been essential for me in understanding the life stages we all go through and how to manage transition best.<p>-Going on extreme/esoteric retreats: like climbing a snowy mountain this winter in Poland in just a bathing suit. I'm trying to push myself physically in ways I've never done before.<p>-Bought a house for the first time and am learning to be a DIY god.<p>-Supporting my wife's entrepreneurial journey as much as possible (she's the founder of her own successful company).<p>-Being open again to mentoring/supporting others as much as possible.<p>-I hope to soon become a Court Appointed Advocate so I can help NYC area kids who are caught up in "the system" in some way shape or form.<p>-Oh and...lot of financial/estate planning work :)
Solo founder (with VC), sold after 15 years (last 13 highly profitable).<p>Good question. Trying to invest carefully, enjoy life and undo the damage entrepreneurship did to my friendships, hobbies... No 40+ hours/week jobs any more, thank you.
I sold my company last year and the deal came with a standard lock-up period. The company that bought us has a really bright future and I'm excited to be part of their journey so I don't mind.<p>I'm currently working hard on integrating the product into their portfolio. Since they are using our former company as a stepping stone into a new market it's a lot like running a startup again, just with much more capital and people.
First company I sold... paid off student loans, traveled around for a year.... then started a consultancy..<p>Second company I sold... invested in a friend's business (she's now my wife), self funded another business (that one failed to find a buyer).... went back to work...<p>Third company I sold... paid down mortgages, put kids into private schools, fixed up house, self funded another business ( currently a going concern, break even)...<p>What do I do now? Keep working... started a new businesses
and handed off day to day operations to my business partner,
and am now taking a new job so I can move to Europe.<p>What do I plan to do in the future... same thing, keep working, looking for interesting projects, probably start more business.
I played professional poker for 3-4 years after selling my first startup in 2007. In hindsight I should have jumped straight back into tech, but I was seriously burned out and the poker monies was good.
We sold to one of the mega tech companies a couple of years ago. I'm still at the company as an engineering manager. I haven't decided what I want to do next and there's still some time until my golden handcuffs expire.
I'll do a throwaway for this. Company had an exit that was about $120m personally for me about 3 years ago. It was a hard slog of about 14 years during which time me and my cofounders got sick of each other, most relationships that I came in with blew up and so on.<p>It is so very strange to not work. First off, everyone all the time is lightly nagging you to work. I don't want to work! I already did that. Surprisingly it is my retired parents who nag the least since they understand retirement the best. It's everyone else my own age (35) that is weird. People who lightly know you ask 100 questions and you sort of have to lie or carefully select truths when you first meet someone because it goes badly saying what you really think most days. Some variation on "Don't you get bored?" constantly coming up. Answer is - no!<p>After a few years of this lifestyle I am settled in quite nicely and almost don't remember working except as a distant other life. I work out, I see friends, I go drinking, I get up at 7am, I read Hacker News, I do a hobby here and there. Any time I throw myself into a hobby I typically find it fills 2-3 hours a day that is just about enough time in a day to be busy for me nowadays.<p>One thing that definitely differentiates is I can travel and do the hobbies of a rich person. I rarely get to throw around numbers with strangers so almost weird to even type but I am spending $2.4m this year just on my little pet projects. Not businesses - just stuff I wanna do for fun with no real purpose.<p>I am very serious about managing my money and I'm a wealth manager's worst nightmare. I meet with everyone, talk endlessly about what is possible, read a lot on investment, and very very rarely give people my business. They are welcome to pitch but after meeting with a ton of folks I ended up making it my part time job and I always know more than the back slapping sales guys they send to try and get 1% fees out of me.<p>You end up finding other people in similar situations. I have a good friend from my startup days in a similar boat with a slightly lower number who made $8m on crypto this year purely out of boredom. He made $10m the year before on a startup he cofounded for 18 months again out of boredom. We get together every week or two, talk about the struggle to keep busy but not too busy. Ha it sounds like we are complaining! It's just a balance as we navigate having fun with projects but not getting stuck in a decade long slog again.<p>I guess I like the idea of being 'rich uncle' or 'grandpa' to a startup, having a flexible amount of involvement. Perhaps daily for 6 months, 4 days a week for a year more, and then 1 day a week from there. In the real world I just worry I'd be so involved it would accidentally be me killing myself and stressing out for 7 years to build a $20m company when my investments make me $7 a year living my life with freedom.<p>Dating is a bit funny when you don't work; you sort of self-select the people for whom it is an issue. People see my house at some point in the dating cycle and there's no hiding the situation. I have on a whim with 24 hours notice taken a girl I was attracted to across the world, had a great week, and then basically that was it. But by and large dating is just normal go around have dinner get a drink stuff, no helicopter sunset champagne yacht adventures. I feel a little bad I'm doing it wrong. Very few gold diggers in my life, surprisingly. I kind of was hoping at one point my friends would have to tear me off of some model. Ah well. I watch TV shows like Ballers and their idea of what rich people are like is really funny to me; I do normal things and date normal people. I suspect based on dating history I'm going to become a stay at home dad to a career minded woman. I suspect it is rewarding to raise the kids?
Congratulations on your success!. Just wondering - How old were you when you started your company,what would you do differently when starting another company and the market that you were in, was a large one or a niche?
The startup nearly killed me but I cashed out ~$3M after taxes. It’s all invested in a portfolio of index funds.<p>I moved to a ski town in Colorado and ski 3x per week and volunteer teach fitness classes 4x per week.<p>My wife and I have plenty of time and money so we “live sexy” - basically we’re swingers. We try to hook up with others for a threesome our foursome once a month or so. It is insanely fun but only works because we have a super strong relationship.<p>Hooking up with others has been great motivation to stay healthy. I live close to the main street in our town and walk to the grocery store most days for lunch. I’m in the best physical shape of my life.<p>I sleep on average 9 hours a night. If I ever feel at all in a negative mood I take a nap and feel great again.<p>I stay lightly in the entrepreneurial game but don’t do anything that demands much of my time. Working ~20 hours a week I’ll do ~$100k in profits.<p>My wife and I talk a lot about how we’re basically cheating at life because money isn’t supposed to buy happiness but in our case it definitely has!
I haven't succeeded in that area yet. But here's what I would do:
I'd get a job for about 20h/week as a developer because I like developing. I'd charge a rather low pay and make sure already in the interview that the boss knows I can leave any time if he pisses me off too much. Reason being that without a regular main task and daily interaction with the same people even the biggest loner feels lonely and useless.<p>Then I would spend a lot of time travelling, prepping travels, honing my hobbies, and probably I would also make investing more of a hobby. I expect it's good to see the effort and ambition of other people succeeding, even if one is only passively involved in what they are doing.<p>Last but not least: I hope you ask this question before you succeeded financially. In the big topics in life one should have at least a broad idea what one wants to do before huge failures or huge successes are incoming.