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I am in my early forties, and have been starting companies since I was 16. I am well into my fifth serious company now (depending on how you count). But somehow

I am in my early forties, and have been starting companies since I was 16. I am well into my fifth serious company now (depending on how you count). But somehow, I keep repeating the same mistakes, and I am running out of ideas on how to fix it, to a degree that I have just stopped doing stuff two years ago. (Fortunately(?) I am well enough now to just give up...) For some reason, I always end up with an unhappy team. Even if the company is successful on paper in terms of numbers, there is always the feeling you hurt feelings no matter what you do, there's always someone who will feel attacked by someone else's internal communication. To a point where that even leaks to customers. This sounds easy to fix, but I am really conscious about it, and tried various strategies, with less involvement from my side, more involvement, having someone else do the hiring decisions, etc. - with my latest company, six years ago, I tried to stay out of it, hired CEOs, but now the company "works, barely" but there's nobody taking any initiative, nobody is passionate about it, everyone is just doing the minimal they can. I predict will not survive more than another few years. It makes me sad sometimes because the ideas behind the companies/products/services seem to be fine, the market is there, the money flows work, even without VCs. I'm just getting tired of all the social problems. This is not something my CS degree and all the coding and later management books and training prepared me for. (Throwaway account to protect the innocent.)

jkcorrea 6y ago
Thanks for such an honest introspective to a life that I'm sure many of us here envy from the outside. This may be cliché, but I've heard a lot of successful founders talk about how they see the best and worst character traits in them manifest in the company culture, often 10x'd if left unchecked. Have you given any thought to how your own personality is affecting your babies (aka your companies)? Hiring/outsourcing the problem to someone else sounds like you're not confronting it head on - and teaching your employees that they can/should do the same. Probably reading too much into this though! Thanks for sharing.
- anon2190 6y ago
  No, that's exactly it. At the beginning of course I thought it was bad hiring decisions, but after a while it became clear that this is "haunting me", and the only conclusion I can draw is that it has something to do with me. Which is when I started really to experiment with various strategies, none of which worked (probably because I can't run away from myself.) It is a bit sad, since I was quite successful in building networks, outside of my own companies: I am surrounded by a lot of entrepreneur-type people which I consider my friends, I have friendly investors lined up to support my product ideas. And I have at least 20 more "good ideas" that could be worth pursuing, but I am very reluctant to do so. So, two years ago, I extracted myself from everything. I've read what must now be at least two dozen "therapy books", started therapy with external professionals, but it doesn't feel like anything is bringing me closer to "the problem". I've always tried to establish an open culture, flat hierarchies, openly talking about things. But I became careful about it too, since I don't want to push stuff on others if they don't see the need. If it is always only me that wants to talk about such things, and rarely anyone else has anything to say, everybody is just waiting for me to "declare" how to do things, what the priorities should be... In all these years, I can remember only a couple of situations where anyone suggested to do something different from what I suggested. Yes, very likely I am "not a good leader". I recognize this. I don't want to be. I "just" want to have teams where you do stuff together, because it is fun, because it has a purpose, because it makes money, whatever. It works a lot better in situations where everyone has their own agenda and is not hired by "my company". What I always hoped for is to end up with a "real co-founder", but that never happened. I have lots of "co-founder friends", but of course we are all passionate about our own ideas... so lately I've been thinking, I should finally join some existing effort, instead of trying again and again to get my own efforts off the ground.
  - jkcorrea 6y ago
    > Yes, very likely I am "not a good leader". I recognize this. I don't want to be. I "just" want to have teams where you do stuff together, because it is fun, because it has a purpose, because it makes money, whatever. It works a lot better in situations where everyone has their own agenda and is not hired by "my company". Ironically, this is the way the leaders I most admire also talk. Maybe you're putting to much emphasis and pressure on yourself, maybe your employees really did want to belong to "your company" and be on the same agenda as you but that was too stressful a burden to bare? Either way, after 5 lead roles for yourself, taking a supporting cast role sounds like a good idea with little risk, if you hate it well at least you'll know for sure
exmanager12 6y ago
Interesting story. My friend started multiple companies and likewise got completely fed up with “people problems.” Non-stop bickering , complaining and infighting. He decided to get out of anything involving dealing with people and focus on cryptocurrencies. Likewise, I had my run at management and saw how my best intentions and positive support for growth in others inevitably blew up in my face. Even people who “have everything” at work may have problems outside of work they bring to the job. And now those problems are YOUR problems. There is a story arc for peoples careers in a company. They can start off doing great but then everything settles into an equilibrium where people just passively hate each other or are bored. I think the only solution is to keep them busy and distracted by constantly stirring the pot and bringing in outside influence. I think honestly you might just be rediscovering what many serial entrepreneurs seem to know: Start a business and flip it and get out, move on to the next thing. Corporations are artificial tribes, and are unstable because these are people who are forced to hang out with each other because they are getting paid. Would your employees hang out if they weren’t getting paid? Probably not. There is a time limit for how long people will tolerate that. Better to sell the company and let them move on.
p0d 6y ago
Could it be you are looking for the equivalent of a family in the workplace and feel let down? I have found that disappointment can lead from unrealistic expectations. My home wasn't a very happy place when I was growing up. I spent most of my time hanging out with friends outside the home. It has taken me to get to 50 to truly understand the unrealistic expectations I still place on my friends. I carried out an experiment about 6 months ago and stopped contacting friends. Throughout that time about 25% have been in touch. I think in a healthy way I am re-thinking the mutuality of friendship. I will invest my energies more wisely going forward. So maybe you are the problem or maybe you are not. Maybe you are just hoping for a world where people are kind. Unfortunately everyone is not awesome as the modern world would have us believe. I think you should keep doing what you do well, being a business man, and not get dragged down by other people's drama. Expect hassle in the workplace and get your lift from family and friends.

jkcorrea 6y ago

Thanks for such an honest introspective to a life that I'm sure many of us here envy from the outside. This may be cliché, but I've heard a lot of successful founders talk about how they see the best and worst character traits in them manifest in the company culture, often 10x'd if left unchecked. Have you given any thought to how your own personality is affecting your babies (aka your companies)? Hiring/outsourcing the problem to someone else sounds like you're not confronting it head on - and teaching your employees that they can/should do the same. Probably reading too much into this though! Thanks for sharing.

anon2190 6y ago
No, that's exactly it. At the beginning of course I thought it was bad hiring decisions, but after a while it became clear that this is "haunting me", and the only conclusion I can draw is that it has something to do with me. Which is when I started really to experiment with various strategies, none of which worked (probably because I can't run away from myself.) It is a bit sad, since I was quite successful in building networks, outside of my own companies: I am surrounded by a lot of entrepreneur-type people which I consider my friends, I have friendly investors lined up to support my product ideas. And I have at least 20 more "good ideas" that could be worth pursuing, but I am very reluctant to do so. So, two years ago, I extracted myself from everything. I've read what must now be at least two dozen "therapy books", started therapy with external professionals, but it doesn't feel like anything is bringing me closer to "the problem". I've always tried to establish an open culture, flat hierarchies, openly talking about things. But I became careful about it too, since I don't want to push stuff on others if they don't see the need. If it is always only me that wants to talk about such things, and rarely anyone else has anything to say, everybody is just waiting for me to "declare" how to do things, what the priorities should be... In all these years, I can remember only a couple of situations where anyone suggested to do something different from what I suggested. Yes, very likely I am "not a good leader". I recognize this. I don't want to be. I "just" want to have teams where you do stuff together, because it is fun, because it has a purpose, because it makes money, whatever. It works a lot better in situations where everyone has their own agenda and is not hired by "my company". What I always hoped for is to end up with a "real co-founder", but that never happened. I have lots of "co-founder friends", but of course we are all passionate about our own ideas... so lately I've been thinking, I should finally join some existing effort, instead of trying again and again to get my own efforts off the ground.
- jkcorrea 6y ago
  > Yes, very likely I am "not a good leader". I recognize this. I don't want to be. I "just" want to have teams where you do stuff together, because it is fun, because it has a purpose, because it makes money, whatever. It works a lot better in situations where everyone has their own agenda and is not hired by "my company". Ironically, this is the way the leaders I most admire also talk. Maybe you're putting to much emphasis and pressure on yourself, maybe your employees really did want to belong to "your company" and be on the same agenda as you but that was too stressful a burden to bare? Either way, after 5 lead roles for yourself, taking a supporting cast role sounds like a good idea with little risk, if you hate it well at least you'll know for sure

exmanager12 6y ago

Interesting story. My friend started multiple companies and likewise got completely fed up with “people problems.” Non-stop bickering , complaining and infighting. He decided to get out of anything involving dealing with people and focus on cryptocurrencies. Likewise, I had my run at management and saw how my best intentions and positive support for growth in others inevitably blew up in my face. Even people who “have everything” at work may have problems outside of work they bring to the job. And now those problems are YOUR problems. There is a story arc for peoples careers in a company. They can start off doing great but then everything settles into an equilibrium where people just passively hate each other or are bored. I think the only solution is to keep them busy and distracted by constantly stirring the pot and bringing in outside influence. I think honestly you might just be rediscovering what many serial entrepreneurs seem to know: Start a business and flip it and get out, move on to the next thing. Corporations are artificial tribes, and are unstable because these are people who are forced to hang out with each other because they are getting paid. Would your employees hang out if they weren’t getting paid? Probably not. There is a time limit for how long people will tolerate that. Better to sell the company and let them move on.

p0d 6y ago

Could it be you are looking for the equivalent of a family in the workplace and feel let down? I have found that disappointment can lead from unrealistic expectations. My home wasn't a very happy place when I was growing up. I spent most of my time hanging out with friends outside the home. It has taken me to get to 50 to truly understand the unrealistic expectations I still place on my friends. I carried out an experiment about 6 months ago and stopped contacting friends. Throughout that time about 25% have been in touch. I think in a healthy way I am re-thinking the mutuality of friendship. I will invest my energies more wisely going forward. So maybe you are the problem or maybe you are not. Maybe you are just hoping for a world where people are kind. Unfortunately everyone is not awesome as the modern world would have us believe. I think you should keep doing what you do well, being a business man, and not get dragged down by other people's drama. Expect hassle in the workplace and get your lift from family and friends.