13 ms·

I regret selling my startup

101 points by eastbound 3y ago

silexia 3y ago
The lesson here is to never take VC money or any other investor money if you can avoid it. You lose your dream and become the slave to someone else's ideas the moment you sell.
jongjong 3y ago
Sometimes I feel like people who sell their startup for a modest sum (hundreds of thousands to low millions) get put in a box of 'not ambitious enough' and this makes it hard to get new opportunities later as investors are seemingly all looking for unicorn founders who want to become billionaires and then achieve world domination... I feel like any signal that you are a rational human being with well-defined, limited needs is going to be a huge turn off for investors. I don't think it's rational at all but I guess that's what decades of low interest rates does to them.
- satvikpendem 3y ago
  Why do they have to take VC? The founder in this article bootstrapped their business and sold, they can always do that again.
  - jongjong 3y ago
    The odds of succeeding with a bootstrapped software startup are tiny. Though I don't know maybe it's different in the US.
    - gnicholas 3y ago
      The bar for success is much lower. VCs want a big multiple, so they want you to take risks. If the risks pay off, everyone wins big. But when you're bootstrapping, it can be a 'win' to make a couple hundred grand a year, working part-time. Most people consider that to be a pretty good gig.
    - j7ake 3y ago
      The odds of succeeding with VC is even tinier. It’s just that the media hype up the lottery winners so VC continues to have companies wanting their money.
    - satvikpendem 3y ago
      But they already did it once, which massively raises the odds the next time around, which might not be so for VC, whose odds anyway is still tinier than bootstrapping, because you can just make enough to live off of and call that successful.
- vidarh 3y ago
  You just have to frame it accordingly. If you go to a VC and boast about an exit of hundreds of thousands as if it's be a success to the., that may give a VC pause, because it's be a failure to them. Failure doesn't bother VCs so much as failure to understand that an exit that size isn't what success looks like to them. It's fine to say it was success to you at that point. But if that is what you want this time too, a VC is wrong for you. If you want a VC investment, you need them to understand you want a big exit this time. I used to work at a VC, and one of the most frequent reasons we didn't take pitches forward was founders who presented a great pitch that fit what you described. We rejected them because while it'd be entirely rational for them to want to take an exit that'd make them happy, those goals are fundamentally incompatible with a VC funds risk profile. Consider that most VC funds invest in high risk startups, and so most of their investments fail. For that reason you need a portion of the survivors to give massive returns. Then it's irrational to cap your potential upside return from the companies that become successful enough to have a shot at providing those returns. This isn't just greed, but survival: most VCs fail to raise a second fund because they either fail to even return the capital or return too low returns to be worth it. You set yourself up for failure if you put your money in a high risk startups where the founder promises you that your best possible return will be, say, 5x. And so if you as a founder want "well defined, limited", VC capital isn't for you, and that's fine. There are other investors.
  - earthling8118 3y ago
    So they choose to invest in high risk scenarios and as a result it becomes a matter of survival, and you're claiming that greed isn't involved? Is that not the reason to invest in high risk as opposed to low risk?
- gnicholas 3y ago
  Part of the reason VC's are more comfortable investing in founders who have had exits already is they know the founder will be less tempted to take a $5M acquisition offer because he already has a decent amount of cash. Founders who have already had one liquidity event are more aligned with the VC's goals: swing for the fences — don't play it safe to make sure you can pay off your house.
gnicholas 3y ago
When I see or hear advice, I try to understand what the person's context was. Here, I feel like I don't know enough about the founder's situation to know whether any of this would be relevant to me. For example, does he have a family? How old is he? Roughly how much money did he sell for? How much profit was the business generating beforehand, and what was its trajectory? Without knowing things like this, I can't really tell if his advice would be relevant at all for me.
- Subdivide8452 3y ago
  He gives reasons why it didn’t work for him. He gives 10 pillars of his personality, 4 of these pillars were standing due to his company ownership. You don’t need to have the exact same pillars, but you need to project it upon your own life and see how selling the company would effect your personality. Then consider it for yourself if it’s worth it.
chris-orgmenta 3y ago
This seems a little 'grass is greener' to me. Not sure if this is glib, but: You can build the business again from scratch (ok, maybe you have a non compete for a while...) But you can't magic the $ you just got, out of thin air. So he's been paid for the hard work he has done, and now if he so chooses he can do the same again, or different. So seems like Boris is standing on the greener grass right now, to me at least. I think the post-sale reflection is naturally something that will make people question their decisions... It may be possible for Boris to Stoically rearrange his view here. There's definitely a bright shiny alternative to regret/second-guessing.
- chris-orgmenta 3y ago
  Or to put it another way: It looks like Boris created, nurtured and sold something (to safe, loving hands), with nice closure. That to me sounds like something to be very proud of, and something that you can cherish and reflect back on with positive (not bitter-sweet) emotion, and keep in contact with the friends made along the way. And the freedom and opportunities ahead are also something that might be harnessable? That power... You can generate a 'bubbly school-holidays' emotion from something like that. Apprehension + Excitement + Unknowing + Freedom?... I don't know, 'bubbly school holiday feeling' is what I always come back to in order to describe it.
- cornel_io 3y ago
  Re: building again... For some people, they don't have the same drive once they've done it once and were successful. I've got friends who were incredible operators for their first N companies, because they were hungry, but then after a big cashout they started to suck at their N+1st attempts. They make mistakes like being unwilling to start small, feeling like they should be Respected(TM) and that getting in the way of their relationships with potential partners, not being frugal with runway, being too precious about repeating exactly what worked before, etc. I've also seen some completely unable to ever fall in love with an idea the way they did pre-exit, and just bounce around doing projects forever without ever committing to anything. On the other hand some people get better, much better, on their later tries. So YMMV, probably depending on your personality.
farmdve 3y ago
I never understood selling of the company unless you've been working in it for 20 years. Like isn't the idea to be your own boss? And why sell it, if you don't have the next idea for the next business up and running? I don't know any tech startup entrepreneurs, but I do have relatives who started their own businesses but always had backup plans and diversity.
- satvikpendem 3y ago
  The article covers this, one can just get tired of it all and want to divest. It's also better to be diverse in your investments rather than putting all your eggs in one basket and hoping it doesn't fail after 20 years, which can definitely happen. Sell, live off the money you made from selling, and take a break until you get your next few ideas.
- gnicholas 3y ago
  It all depends on the multiple. If someone is giving you 3 years of profit up-front, that's probably not worth it. If they're giving you 10 years of profit, that could make sense. You avoid having to work for that period of time, and you avoid the risk that something could go wrong (with the company, the economy, the sector) during that time. It also allows you to diversify your assets.
  - lelanthran 3y ago
    > If someone is giving you 3 years of profit up-front, that's probably not worth it. TBH, 3 years of profit upfront is probably worth it if you have no good plans to expand that profit.
    - gnicholas 3y ago
      Really? IMO 3x profit is a terrible multiplier. Depending on the business, 3x revenue could be worth it, but that's a completely different calculation. Of course, it also depends on how much work you're doing to sustain that profit. If you're working full-time to make this happen, 3x profit is a more attractive proposition than if you're just cashing the checks.
satvikpendem 3y ago
All good points here. For those reading just the title, the article asks to critically examine what values you hold and whether selling is compatible with those values. For me, I see selling as just another step to growing the hoard, as you state in the article, but I don't think it becomes draconic in practice. The key in my opinion and experience is making and selling micro projects, not banking on any one taking off. That way, you can have cash flow and a hoard. Throw the hoard into VTI and let it grow while living off the cash flow (and/or reinvesting it into the business), until the investments become enough to live off of entirely, ie the 4% rule. Pieter Levels or Daniel Vassallo are good examples of this. Just keep trying, don't be saddened by another startup failure, at least you already have one sold which is a lot more than most founders can say. I'm also in NYC, let me know if you want to chat, as you stated at the end of the post.
- Munksgaard 3y ago
  Perhaps I am unfamiliar with this usage of the word horde, but is it possible that you mean hoard?
  - satvikpendem 3y ago
    Yes, sorry, hoard, not horde.
  - redcobra762 3y ago
    Oh come on, you knew he used the wrong word… This isn’t any better, you know. Some people would see this as patronizing.
    - satvikpendem 3y ago
      I appreciate the correction, helps me learn something new.
      - redcobra762 3y ago
        You didn’t know that horde and hoard were different words?
neilv 3y ago
> What you don't know is that when you have a pile of money, you turn into a dragon. The goal becomes to sit on the pile of money and make sure it doesn't get smaller, and ideally grows on its own. Is this universal? If I had at least a several-million post-tax windfall, I think I'd buy a nice home and maybe a little beach house, put the rest in index funds, and spend my time being healthy, and building particular open source software and hardware. (Building things without résumé keywords being a consideration; it's almost unimaginable, now.)
- hiAndrewQuinn 3y ago
  I'd put it all in index funds, but I'm still fairly young and my dream has always been to be able to max out my kids' Roth IRAs from birth somehow. (I'm still working on the "how do you get a baby to have taxable income" angle.)
  - gnicholas 3y ago
    The normal path is to establish a trust fund, into which you and your spouse contribute the maximum annual exclusion amount. By the time they're grown up, they've got a tidy sum. And when they get married, you and your spouse can give the maximum gift amount to each them and their spouse every year.
    - hiAndrewQuinn 3y ago
      You're a saint, thank you
      - gnicholas 3y ago
        Not a saint, just a former tax lawyer. There are more elaborate strategies that allow people to move larger sums, particularly if they have stock in pre-IPO companies. If you find yourself in need of that kind of advice, find a 'private client' lawyer to help you understand and navigate the complex rules.
- com2kid 3y ago
colesantiago 3y ago
but you made money and got time now. other founders aren't so lucky to find a buyer. many just shut down
bhakunikaran 3y ago
Out of curiosity, how do you now view the concept of success in entrepreneurship, given your experience? Do you think there's a way for founders to prepare themselves emotionally and mentally for the possibility of selling their business?
- bberenberg 3y ago
  I think the best short answer I can give is that I’m generally aligned with the book The Infinite Game.
locallost 3y ago
I don't know why people are so negative in the comments or overthinking what the author wanted to say, when it's pretty clear. Running the company is what made him tick, made him feel alive, and ultimately made him happy. He's cashed out, but sitting around thumb twiddling and maintaining the pile of cash might be an ok life, might make some people happy, but it's not making him happy. There's nothing wrong with any of that. The advice you can get from that is, figure out what it is that makes you enjoy life. If it's feeling secure because you have a pile of cash, then you will do the same as him, but be satisfied with the decision.
- iancmceachern 3y ago
  Totally, you do you. I love the movie birdman, on the topic.
- neilv 3y ago
  I thought it was a refreshingly humble and honest-sounding post, by someone who'd done a lot of reflection. Of course, not everyone matches the writer's motivations, and he went and told the reader what those motivations are.
- bberenberg 3y ago
  Maybe this needs an update to the post. I am happy. My life is amazing in terms of health, fitness, diet, family life, where I live, travel etc. But I am also without a driving force. It gives me a new appreciation for the athletes or musician who un-retires.
  - locallost 3y ago
    I apologize, I never wanted to imply somebody I don't know is unhappy, guess it kind of came off wrong. Wish you anyway all the best and thanks for a very clear blog post.
  - csdvrx 3y ago
    > But I am also without a driving force. It gives me a new appreciation for the athletes or musician who un-retires. I have a friend who phrased that very well: the problem is "you're waiting for death" because a life without a "driving force" is just waiting for death, as it will eventually do its part. > I am happy. My life is amazing in terms of health, fitness, diet, family life, where I live, travel etc. Waiting can be happy, but it's still waiting. Also, how things are during the wait will change: fitness and health aren't perfect forever, likewise family members aren't immortals No judgement value is implied: that's what retirees do, and what most people aspire to do, so it shouldn't be so bad. Yet I believe we as human beings need things to do.
navane 3y ago
It always gets worse before it gets better.
stuaxo 3y ago
Now they are free to do a business with organic growth or anything else they like, that doesn't have the aim of being sold at the end.
outcoldman 3y ago
I am kind of, have the same flow of thoughts. I have never worked on the project for more than 4 years. Now I have a product that I have built and live on, for the last 7 years. I don't have that much passion about this product anymore. But at the same time it allows me right now to work only 4 hours a week on average, and spend 2 months a year to build new versions of the product. I am making good Google Principal Software Total compensation. Selling a company means I can probably get 4-6x of my annual income. But I am afraid to become that dragon on the pile of money. Draining money will be terrifying for me. And I am not good with managing money. At the same time, I am afraid that company can slowly disappear, customers choose alternatives. And maybe 4-6 years that is how much I can get from it. But at the same time I will have opportunity to fix things, adjust my life based on the income.
deleted 3y ago
[deleted]
brianwawok 3y ago
Why does ever seller of a business become an angel investor? And the follow up, I wonder how business seller angels perform compared to your normal angel fund...
- gnicholas 3y ago
  One cause is the tax benefits. If you're selling qualified small business stock, you can defer gains by rolling them over into new qualified small business investments, within a certain time window. That's a pretty big tax preference, and it means that even if you don't do an amazing job of angel investing, you might be better off than taking the money, paying tax on the gains, and investing it in real estate or the stock market.
- tracerbulletx 3y ago
  I'd guess because it is a way to be involved in start ups without the intense work of being a founder?
  - brianwawok 3y ago
    Ah I guess that is true. Keep some of the fun parts without the bad parts. If you are just throwing out 10-100k angel rounds, depending on how much you sold for it's pretty small. Wonder if you could do the same thing just offering to be an advisor or on the board for startups without the check?
amadeuspagel 3y ago
Power is a very fundamental motivation, maybe the most fundamental one[1], and I think a lot of people regret selling their companies because they think they want things you're supposed to want, like comfort and leisure, when they really want power. [1]: https://en.wikipedia.org/wiki/Will_to_power https://en.wikipedia.org/wiki/Will_to_power
- nprateem 3y ago
  I think it's actually a sense of purpose
- eastbound 3y ago
  Phrasing it as power makes it sound negative. As the other comment says, it could be a sense of purpose, or having respect (which is power but in its human form), or just keeping busy. If I were a millionaire, I know I’d keep my work just to be busy. I know it because I’m a millionaire. And I certainly don’t want all those negative thoughts.
  - amadeuspagel 3y ago
    That power sounds negative is the problem.
stevage 3y ago
> for me it was a personal incompatibility with parts of the business I don’t want to delve into in this post. Without this, the post was pretty abstract and not very interesting.
thrwawy995 3y ago
Great post! I've gone through a similar experience after selling a business a few years ago. I especially liked your "offense vs defense" point on cash flows. I'd never thought of it that way but its a very apt description of the change in mindset. All that said, I can't say that I regret the decision. Best of luck

101 points by eastbound 3y ago

The lesson here is to never take VC money or any other investor money if you can avoid it. You lose your dream and become the slave to someone else's ideas the moment you sell.

jongjong 3y ago

Sometimes I feel like people who sell their startup for a modest sum (hundreds of thousands to low millions) get put in a box of 'not ambitious enough' and this makes it hard to get new opportunities later as investors are seemingly all looking for unicorn founders who want to become billionaires and then achieve world domination... I feel like any signal that you are a rational human being with well-defined, limited needs is going to be a huge turn off for investors. I don't think it's rational at all but I guess that's what decades of low interest rates does to them.

satvikpendem 3y ago
Why do they have to take VC? The founder in this article bootstrapped their business and sold, they can always do that again.
- jongjong 3y ago
  The odds of succeeding with a bootstrapped software startup are tiny. Though I don't know maybe it's different in the US.
  - gnicholas 3y ago
    The bar for success is much lower. VCs want a big multiple, so they want you to take risks. If the risks pay off, everyone wins big. But when you're bootstrapping, it can be a 'win' to make a couple hundred grand a year, working part-time. Most people consider that to be a pretty good gig.
  - j7ake 3y ago
    The odds of succeeding with VC is even tinier. It’s just that the media hype up the lottery winners so VC continues to have companies wanting their money.
  - satvikpendem 3y ago
    But they already did it once, which massively raises the odds the next time around, which might not be so for VC, whose odds anyway is still tinier than bootstrapping, because you can just make enough to live off of and call that successful.
vidarh 3y ago
You just have to frame it accordingly. If you go to a VC and boast about an exit of hundreds of thousands as if it's be a success to the., that may give a VC pause, because it's be a failure to them. Failure doesn't bother VCs so much as failure to understand that an exit that size isn't what success looks like to them. It's fine to say it was success to you at that point. But if that is what you want this time too, a VC is wrong for you. If you want a VC investment, you need them to understand you want a big exit this time. I used to work at a VC, and one of the most frequent reasons we didn't take pitches forward was founders who presented a great pitch that fit what you described. We rejected them because while it'd be entirely rational for them to want to take an exit that'd make them happy, those goals are fundamentally incompatible with a VC funds risk profile. Consider that most VC funds invest in high risk startups, and so most of their investments fail. For that reason you need a portion of the survivors to give massive returns. Then it's irrational to cap your potential upside return from the companies that become successful enough to have a shot at providing those returns. This isn't just greed, but survival: most VCs fail to raise a second fund because they either fail to even return the capital or return too low returns to be worth it. You set yourself up for failure if you put your money in a high risk startups where the founder promises you that your best possible return will be, say, 5x. And so if you as a founder want "well defined, limited", VC capital isn't for you, and that's fine. There are other investors.
- earthling8118 3y ago
  So they choose to invest in high risk scenarios and as a result it becomes a matter of survival, and you're claiming that greed isn't involved? Is that not the reason to invest in high risk as opposed to low risk?
gnicholas 3y ago
Part of the reason VC's are more comfortable investing in founders who have had exits already is they know the founder will be less tempted to take a $5M acquisition offer because he already has a decent amount of cash. Founders who have already had one liquidity event are more aligned with the VC's goals: swing for the fences — don't play it safe to make sure you can pay off your house.

gnicholas 3y ago

When I see or hear advice, I try to understand what the person's context was. Here, I feel like I don't know enough about the founder's situation to know whether any of this would be relevant to me. For example, does he have a family? How old is he? Roughly how much money did he sell for? How much profit was the business generating beforehand, and what was its trajectory? Without knowing things like this, I can't really tell if his advice would be relevant at all for me.

Subdivide8452 3y ago
He gives reasons why it didn’t work for him. He gives 10 pillars of his personality, 4 of these pillars were standing due to his company ownership. You don’t need to have the exact same pillars, but you need to project it upon your own life and see how selling the company would effect your personality. Then consider it for yourself if it’s worth it.

chris-orgmenta 3y ago

This seems a little 'grass is greener' to me. Not sure if this is glib, but: You can build the business again from scratch (ok, maybe you have a non compete for a while...) But you can't magic the $ you just got, out of thin air. So he's been paid for the hard work he has done, and now if he so chooses he can do the same again, or different. So seems like Boris is standing on the greener grass right now, to me at least. I think the post-sale reflection is naturally something that will make people question their decisions... It may be possible for Boris to Stoically rearrange his view here. There's definitely a bright shiny alternative to regret/second-guessing.

chris-orgmenta 3y ago
Or to put it another way: It looks like Boris created, nurtured and sold something (to safe, loving hands), with nice closure. That to me sounds like something to be very proud of, and something that you can cherish and reflect back on with positive (not bitter-sweet) emotion, and keep in contact with the friends made along the way. And the freedom and opportunities ahead are also something that might be harnessable? That power... You can generate a 'bubbly school-holidays' emotion from something like that. Apprehension + Excitement + Unknowing + Freedom?... I don't know, 'bubbly school holiday feeling' is what I always come back to in order to describe it.
cornel_io 3y ago
Re: building again... For some people, they don't have the same drive once they've done it once and were successful. I've got friends who were incredible operators for their first N companies, because they were hungry, but then after a big cashout they started to suck at their N+1st attempts. They make mistakes like being unwilling to start small, feeling like they should be Respected(TM) and that getting in the way of their relationships with potential partners, not being frugal with runway, being too precious about repeating exactly what worked before, etc. I've also seen some completely unable to ever fall in love with an idea the way they did pre-exit, and just bounce around doing projects forever without ever committing to anything. On the other hand some people get better, much better, on their later tries. So YMMV, probably depending on your personality.

farmdve 3y ago

I never understood selling of the company unless you've been working in it for 20 years. Like isn't the idea to be your own boss? And why sell it, if you don't have the next idea for the next business up and running? I don't know any tech startup entrepreneurs, but I do have relatives who started their own businesses but always had backup plans and diversity.

satvikpendem 3y ago
The article covers this, one can just get tired of it all and want to divest. It's also better to be diverse in your investments rather than putting all your eggs in one basket and hoping it doesn't fail after 20 years, which can definitely happen. Sell, live off the money you made from selling, and take a break until you get your next few ideas.
gnicholas 3y ago
It all depends on the multiple. If someone is giving you 3 years of profit up-front, that's probably not worth it. If they're giving you 10 years of profit, that could make sense. You avoid having to work for that period of time, and you avoid the risk that something could go wrong (with the company, the economy, the sector) during that time. It also allows you to diversify your assets.
- lelanthran 3y ago
  > If someone is giving you 3 years of profit up-front, that's probably not worth it. TBH, 3 years of profit upfront is probably worth it if you have no good plans to expand that profit.
  - gnicholas 3y ago
    Really? IMO 3x profit is a terrible multiplier. Depending on the business, 3x revenue could be worth it, but that's a completely different calculation. Of course, it also depends on how much work you're doing to sustain that profit. If you're working full-time to make this happen, 3x profit is a more attractive proposition than if you're just cashing the checks.

satvikpendem 3y ago

All good points here. For those reading just the title, the article asks to critically examine what values you hold and whether selling is compatible with those values. For me, I see selling as just another step to growing the hoard, as you state in the article, but I don't think it becomes draconic in practice. The key in my opinion and experience is making and selling micro projects, not banking on any one taking off. That way, you can have cash flow and a hoard. Throw the hoard into VTI and let it grow while living off the cash flow (and/or reinvesting it into the business), until the investments become enough to live off of entirely, ie the 4% rule. Pieter Levels or Daniel Vassallo are good examples of this. Just keep trying, don't be saddened by another startup failure, at least you already have one sold which is a lot more than most founders can say. I'm also in NYC, let me know if you want to chat, as you stated at the end of the post.

Munksgaard 3y ago
Perhaps I am unfamiliar with this usage of the word horde, but is it possible that you mean hoard?
- satvikpendem 3y ago
  Yes, sorry, hoard, not horde.
- redcobra762 3y ago
  Oh come on, you knew he used the wrong word… This isn’t any better, you know. Some people would see this as patronizing.
  - satvikpendem 3y ago
    I appreciate the correction, helps me learn something new.
    - redcobra762 3y ago
      You didn’t know that horde and hoard were different words?

neilv 3y ago

> What you don't know is that when you have a pile of money, you turn into a dragon. The goal becomes to sit on the pile of money and make sure it doesn't get smaller, and ideally grows on its own. Is this universal? If I had at least a several-million post-tax windfall, I think I'd buy a nice home and maybe a little beach house, put the rest in index funds, and spend my time being healthy, and building particular open source software and hardware. (Building things without résumé keywords being a consideration; it's almost unimaginable, now.)

hiAndrewQuinn 3y ago
I'd put it all in index funds, but I'm still fairly young and my dream has always been to be able to max out my kids' Roth IRAs from birth somehow. (I'm still working on the "how do you get a baby to have taxable income" angle.)
- gnicholas 3y ago
  The normal path is to establish a trust fund, into which you and your spouse contribute the maximum annual exclusion amount. By the time they're grown up, they've got a tidy sum. And when they get married, you and your spouse can give the maximum gift amount to each them and their spouse every year.
  - hiAndrewQuinn 3y ago
    You're a saint, thank you
    - gnicholas 3y ago
      Not a saint, just a former tax lawyer. There are more elaborate strategies that allow people to move larger sums, particularly if they have stock in pre-IPO companies. If you find yourself in need of that kind of advice, find a 'private client' lawyer to help you understand and navigate the complex rules.
com2kid 3y ago

colesantiago 3y ago

but you made money and got time now. other founders aren't so lucky to find a buyer. many just shut down

bhakunikaran 3y ago

Out of curiosity, how do you now view the concept of success in entrepreneurship, given your experience? Do you think there's a way for founders to prepare themselves emotionally and mentally for the possibility of selling their business?

bberenberg 3y ago
I think the best short answer I can give is that I’m generally aligned with the book The Infinite Game.

locallost 3y ago

I don't know why people are so negative in the comments or overthinking what the author wanted to say, when it's pretty clear. Running the company is what made him tick, made him feel alive, and ultimately made him happy. He's cashed out, but sitting around thumb twiddling and maintaining the pile of cash might be an ok life, might make some people happy, but it's not making him happy. There's nothing wrong with any of that. The advice you can get from that is, figure out what it is that makes you enjoy life. If it's feeling secure because you have a pile of cash, then you will do the same as him, but be satisfied with the decision.

iancmceachern 3y ago
Totally, you do you. I love the movie birdman, on the topic.
neilv 3y ago
I thought it was a refreshingly humble and honest-sounding post, by someone who'd done a lot of reflection. Of course, not everyone matches the writer's motivations, and he went and told the reader what those motivations are.
bberenberg 3y ago
Maybe this needs an update to the post. I am happy. My life is amazing in terms of health, fitness, diet, family life, where I live, travel etc. But I am also without a driving force. It gives me a new appreciation for the athletes or musician who un-retires.
- locallost 3y ago
  I apologize, I never wanted to imply somebody I don't know is unhappy, guess it kind of came off wrong. Wish you anyway all the best and thanks for a very clear blog post.
- csdvrx 3y ago
  > But I am also without a driving force. It gives me a new appreciation for the athletes or musician who un-retires. I have a friend who phrased that very well: the problem is "you're waiting for death" because a life without a "driving force" is just waiting for death, as it will eventually do its part. > I am happy. My life is amazing in terms of health, fitness, diet, family life, where I live, travel etc. Waiting can be happy, but it's still waiting. Also, how things are during the wait will change: fitness and health aren't perfect forever, likewise family members aren't immortals No judgement value is implied: that's what retirees do, and what most people aspire to do, so it shouldn't be so bad. Yet I believe we as human beings need things to do.

navane 3y ago

It always gets worse before it gets better.

stuaxo 3y ago

Now they are free to do a business with organic growth or anything else they like, that doesn't have the aim of being sold at the end.

outcoldman 3y ago

I am kind of, have the same flow of thoughts. I have never worked on the project for more than 4 years. Now I have a product that I have built and live on, for the last 7 years. I don't have that much passion about this product anymore. But at the same time it allows me right now to work only 4 hours a week on average, and spend 2 months a year to build new versions of the product. I am making good Google Principal Software Total compensation. Selling a company means I can probably get 4-6x of my annual income. But I am afraid to become that dragon on the pile of money. Draining money will be terrifying for me. And I am not good with managing money. At the same time, I am afraid that company can slowly disappear, customers choose alternatives. And maybe 4-6 years that is how much I can get from it. But at the same time I will have opportunity to fix things, adjust my life based on the income.

deleted 3y ago

[deleted]

brianwawok 3y ago

Why does ever seller of a business become an angel investor? And the follow up, I wonder how business seller angels perform compared to your normal angel fund...

gnicholas 3y ago
One cause is the tax benefits. If you're selling qualified small business stock, you can defer gains by rolling them over into new qualified small business investments, within a certain time window. That's a pretty big tax preference, and it means that even if you don't do an amazing job of angel investing, you might be better off than taking the money, paying tax on the gains, and investing it in real estate or the stock market.
tracerbulletx 3y ago
I'd guess because it is a way to be involved in start ups without the intense work of being a founder?
- brianwawok 3y ago
  Ah I guess that is true. Keep some of the fun parts without the bad parts. If you are just throwing out 10-100k angel rounds, depending on how much you sold for it's pretty small. Wonder if you could do the same thing just offering to be an advisor or on the board for startups without the check?

amadeuspagel 3y ago

Power is a very fundamental motivation, maybe the most fundamental one[1], and I think a lot of people regret selling their companies because they think they want things you're supposed to want, like comfort and leisure, when they really want power. [1]: https://en.wikipedia.org/wiki/Will_to_power https://en.wikipedia.org/wiki/Will_to_power

nprateem 3y ago
I think it's actually a sense of purpose
eastbound 3y ago
Phrasing it as power makes it sound negative. As the other comment says, it could be a sense of purpose, or having respect (which is power but in its human form), or just keeping busy. If I were a millionaire, I know I’d keep my work just to be busy. I know it because I’m a millionaire. And I certainly don’t want all those negative thoughts.
- amadeuspagel 3y ago
  That power sounds negative is the problem.

stevage 3y ago

> for me it was a personal incompatibility with parts of the business I don’t want to delve into in this post. Without this, the post was pretty abstract and not very interesting.

thrwawy995 3y ago

Great post! I've gone through a similar experience after selling a business a few years ago. I especially liked your "offense vs defense" point on cash flows. I'd never thought of it that way but its a very apt description of the change in mindset. All that said, I can't say that I regret the decision. Best of luck