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
I applied to a then nascent part of McKinsey (that is now very mature) called Digital McKinsey, as someone who could help clients build and transform engineering and product organisations. To be a CTO/VP Eng for hire, almost. Then I slowly moved more and more into the non-tech topics.
I was there for almost exactly four years. Learned all kinds of things, but most importantly how to communicate and structure my thinking in a way that works with people senior people from non-tech backgrounds.
* Empathy with the folks who's thinking was alien to me previously. I learned through doing their job. I could communicate with them and work in their context in a way that allows me much more leverage and ability to have impact with engineering.
* I learned the semantics and pragmatics of running a large organisation which gave me the lexicon and confidence to be taken seriously doing it (therefore more leverage) and taught me lots of small but important tactical lessons (e.g. how to manage difficult shareholders)
* How to communicate complex technical subjects to people who either don't/can't/won't understand them.
* A HUGE network
I went back because I missed it. I wanted to do consulting as a way of getting better at being an engineering leader, not leaving it forever. I was offered a few things at VC/PE firms, or in typical 'business' roles, but none of them really appealed. Not my passion.
I had never thought of the big 3 as possible route post-sale.
Sale is not on the radar atm so back to my daily operational duties in my small yet thriving company :-)
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.
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.
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.
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 understand you can find new areas to work in, but I imagine you'd think back to previous work and be tempted to make connections to that field, or use some of what you built previously in the new context.
Is it difficult, or is it just a completely separate problem space?
-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.
-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.
-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.
-Bought a house for the first time and am learning to be a DIY god.
-Supporting my wife's entrepreneurial journey as much as possible (she's the founder of her own successful company).
-Being open again to mentoring/supporting others as much as possible.
-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.
-Oh and...lot of financial/estate planning work :)
I don't know how tall or remote was this mountain, but a guy I know nearly died (well, technically he was dead for a bit while they reanimated him on the rescue helicopter) running in Polish mountains last winter without a proper clothing.
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.
You dont have to be an entrepreneur to be super busy. Some part of the world expect you to work at at least 80 hours a week. So i guess this is good for everyone to know.
*As you grew older, you came to realise how little money actually means.
Lost time is lost, but you can get in touch with old friends, apologise to people you ignored because you were busy, find new hobbies, travel... At least that's what I'm trying to do. I also lost 2 close family members during that time and deeply regret not having spent more time with them, but that's just how it is.
> As you grew older, you came to realise how little money actually means.
I'd still disagree, it means a lot and makes life so much easier. It's just something you tend to take for granted when you have it and other things you don't naturally become more important.
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.
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...
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)...
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.
What do I plan to do in the future... same thing, keep working, looking for interesting projects, probably start more business.
Would you mind sharing round figures? I've always wondered how much pro poker players that don't have endorsements etc. actually manage to scrape away from the game after rake, travel expenses, leaks (pit games), etc.
i'm in the uk and gambling is allowed.
I think it should be illegal in practice because people get into massive downward spirals. Now, that does not mean we need no ban ultra low stakes poker, just the kind of games that cause people to go broke. Aka, someone that loses 200$ a month on poker is not a big deal. Someone that's losing 20,000+$ / month is likely a different story.
I have similar issues with the App Store and feel Apple / Google should limit in app purchases per month.
I live in Ohio, and I'm still unhappy with the fact that we voted to change our state constitution a few years back to allow casinos to be built.
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!
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.
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.
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.
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.
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.
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?
What was the company specializing in that you co-founded?
I've been working on a network of student-led coding clubs. We just finished our 4th semester and are already in 1% of US high schools. With the right support, I think we could make it to 20% by 2020.
firstname.lastname@example.org is my email if at all interested.
Have you written about it anywhere, or want to share it here, maybe?
I moved to a ski town in Colorado and ski 3x per week and volunteer teach fitness classes 4x per week.
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.
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.
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.
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.
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’ll do a few productive benders a year where I shut myself in for a week or two at a time, but invariably I start feeling crappy and need to get back on a healthy schedule.
I think OP’s Hedonism is a perfectly reasonable way to stay happy.
Contrary to religious beliefs, having regular, consistent, and healthy sex is good for the mind and body.
Even your Kama Sutra is a guide to a virtuous and gracious living that discusses the nature of love, family life, and other aspects pertaining to pleasure-oriented faculties of human life.
Stoicism and Hedonism would have been my personal approach to life.
Regular and consistent sex is very healthy, important, and normal. Don’t forget about it while you go along your creative journey.
I love my wife too much to swing. Couldn't and don't want to imagine someone else having sex with my wife.
I like to see her happy. She likes to see me happy. The dynamic obviously isn’t for everyone but it works for us.
Independend of my wifes choice of doing ffm, i will not do this until i'm compftable with fmm and i'm not. I don't even care for ffm or fmm very much anyway but fmm is the deal breaker for ffm.
Anecdote - one of my ex was talked into a threesome with another girl by her ex, thinking how refreshing it would be (and she is not a typical nice girl with a good heart to start with). She couldn't handle it at all, and it contributed to their breakup quite effectively.
Nothing for me, I prefer quality rather than quantity (maybe not the best comparison, but I lack better in this case).
I grew up in a glorified shed on a small fishing island hours off the coast of Australia so the simple life in beautiful nature is something I miss. However I imagine it would be so boring not being able to work or socialise with similar people (tech minded.)
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.
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.