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I've cofounded 4 different startups. All were good ideas that bled cash or time and flopped, largely due to infighting or founder differences. One cofounder of

I've cofounded 4 different startups. All were good ideas that bled cash or time and flopped, largely due to infighting or founder differences. One cofounder of one of the companies got really nasty about trying to leave with the rights to the company and we other two cofounders just let him have it. He sold the rights and it's now a successful venture-backed startup with soaring profits (two cofounders). Good for that team. Since then, I've managed my own single-founder startup. We're profitable, growing, and valued at about $2.2 million. We're implementing a lot more over the course of this year and next, and I will look to exit in early 2018, once our valuation is closer to the $10 million or $20 million range. I have a lot of other companies I want to start after. I will bring on talented people in executive roles who can complement me and make up for my own weaknesses, but I won't cofound again. I'd rather keep the smart, business-oriented people I know in masterminds where we can compare ideas and bounce thoughts off each other, than wade into business situations where our differences turn us into enemies and destroy the company. The general wisdom on picking cofounders is pick a behind-the-scenes guy if you're a visionary, or make sure you're comfortable as the behind-the-scenes guy if you're partnering with a visionary. The problem I find (and one I've seen in a lot of cofounder groups) is that most of the people who want to start startups are visionaries.

benevol 10y ago
> pick a behind-the-scenes guy if you're a visionary, or make sure you're comfortable as the behind-the-scenes guy if you're partnering with a visionary What's your take on the situation where you are both? (Where somebody is visionary, "knows business" and codes as well.)
- pyromine 10y ago
  Not OP, but I'd say consider if you really are all those things. Very few people are, even Zuckerberg isn't, he was a competent coder not a great one but a visionary for sure. Ultimately no one can have it all, learn to focus on the strengths, though if truly all of those are your strengths break forward and absolutely kill it.
- 50CNT 10y ago
  Then you don't need a co-founder. It can still be nice to have one, one guys schleps are another persons hobby. Like I'm good at analysis, but bad at dealing with third-parties. The guy I'm working with is good at dealing with third-parties but is a bit slower at dissecting problems. No worries. There's a number of different other pairings of this kind too, some areas where we have overlap, some stuff one of us needs to figure out, some both of us need to learn. And I think that's pretty cool.
  - leesalminen 10y ago
    Agreed 100%. I could have started my company alone; but then I would've been stuck doing payroll, HR, mediating employee conflict and all that nonsense. My partner is a people person, and I'm not. It works out really well and my staff are happy to not have to deal with me directly (I can be a bit brash).
- bsdpython 10y ago
  There's simply not enough time to do all those things yourself. Find someone "good enough" in one of those areas and have them take over main responsibility.
- throwaway7312 10y ago
  Depends on what your end goal is and what you're starting with. If the goal is to get big and you have funds (or funding), you can be a single founder and just look for a couple of talented people, or perhaps one right-hand man, to take over the roles you're weakest in or that slow you down the most. If your goal is to get big and you don't have funds or can't attract funding, you'll probably do best to look for a cofounder who's comfortable in the behind-the-scenes roll. If you don't have money but there're two of you, and you complementary and on the same page, you'll grow a lot faster than if you don't have money but there's one of you. The situation I ran into was not having money, and having cofounders who were not on the same page with me - that kills companies. If you don't have money but just want a lifestyle business, then it's fine to be a single founder. You'll grow slower, but have freedom, and if all it's about for you is freedom then that'll be fine.
charlesdm 10y ago
> Since then, I've managed my own single-founder startup. We're profitable, growing, and valued at about $2.2 million. We're implementing a lot more over the course of this year and next, and I will look to exit in early 2018, once our valuation is closer to the $10 million or $20 million range. Did you raise any capital on that one? Or was it bootstrapped + growing?
- throwaway7312 10y ago
  We've taken no capital. After the experience of losing control of the cofounded businesses, the last thing I wanted was to bring in investors who'd be staring over my shoulder or telling me what to do. I'd be open to taking capital on a future project, simply because I'm experienced enough now to know what our upside is and what percentage and how much control I'd be comfortable parting with, and for how much. On this present project, I haven't even bothered to explore it, because we have our trajectory over the next 1.5 years mapped out and everything we want to do we can pay for with profits already, so there's not a lot of incentive to take months off from driving the business forward to go shopping around for investors instead.
throwaway1182 10y ago
Interesting data point. However, we're happily chugging along with 6 co-founders, bootstrapped to currently 30 mln us$ valuation and we've only just begun. Then again, your point about "visionaries" (with which you probably mean high-ego people needing a lot of approval) rings true to me. We're all pretty low-key hard-working people with a lot of self-reflection and humility - also it helps it's not the usual failing friends, family or uni buddies combo but we're really more of a casting band with a team mixed and matched from industry professionals by our main founder. In this very setup, it's actually very enjoyable with a lot of pros: Scaling is much faster and easier with invested veterans at the helm, all important departments are headed by founders, also having same-level people in the same company helps enormously with the more difficult decisions and just professional exchange, growing as leaders and 1-1 mentoring. If - and only if - the base of trust is there and continuously honed through communication, this is an amazing way to work and learn. 10/10 would do it again.
- 20yrs_no_equity 10y ago
  You admit you have a main founder. Does this main founder have sorta ultimate authority? Or does he hold the singular original vision from which everyone else's vision/mission/purpose comes from? What's the equity split like among the 6 of you? What created that base of trust you describe? Was it everyone agreeing to follow the "main founders" vision, and him being respectful and not ego driven (so that the vision became shared?)
  - throwaway1182 10y ago
    > Was it everyone agreeing to follow the "main founders" vision, and him being respectful and not ego driven (so that the vision became shared?) Pretty much exactly that plus providing the seed round. In practice, this also definitely had a lot to do with things working out well to have a center piece that's stable, predictable and a little detached, quite the opposite of a show-off. Buying into a main vision and then transferring it into a vision for tech, marketing, sales, product and operations was much easier that way. Equity split was 50:others by the way. Now you might argue this isn't a "real" as in "more equal" cofounder dynamic, but giving away 50% of your company before even starting and then treating those people as equals made a lot of difference, including an enormous buy-in at all key builders of the company. After having experienced how well it played out, I'd do it the same way.
bambax 10y ago
I have been self employed for 17 years as a 1-man consulting shop, and enjoy working alone. I have just started a product activity (making things and selling them to end-users) and can do the work by myself (I design, and then the actual making is done by factories) -- but for the first time I miss someone to talk to, someone with which to explore business ideas and options. Maybe a co-founder wouldn't help much because they would have a vested interest in the discussion, though.
- sandebert 10y ago
  It sounds like you might benefit from starting our joining a mastermind. Is that something you have considered? (I'm not sure how universal "mastermind" is, so here's a link to help explain it a bit, and how to run one: http://www.startupsfortherestofus.com/episodes/episode-167 http://www.startupsfortherestofus.com/episodes/episode-167)
  - bambax 10y ago
    Thank you; I had never heard the term mastermind in that context before. Is it a well-known concept? The second result when googling "startup mastermind" is the post you mention, and the first one is... a reddit thread pointing to that same post. But the idea is exactly what I would need, so thanks!!
    - sandebert 10y ago
      Glad to help. I've been in one for about a year or so, and can't recommend it enough. Not sure how known the concept is, but I think it is fairly well known, especially if you run a bootstrapped startup. And if you're listening to the podcast Startups For the Rest Of Us (recommended!), I'd say it's probably close to 100 percent. One way of finding people for your mastermind is to visit the MicroConf conference, run by the same people as the podcast. (It's a lot easier getting a ticket for the European conference than the US one.)
      - gregpilling 10y ago
rsp1984 10y ago
> The problem I find (and one I've seen in a lot of cofounder groups) is that most of the people who want to start startups are visionaries. It's simpler than that. Most people just prefer slacking off to working their butts off. However it's the narcissists and sociopaths that will call their slacking off being "visionary" while the good guys either just leave or start working their butts off as everybody else. Obviously you want to pick your cofounder(s) among the latter kind.
- nxzero 10y ago
  Working your butt off has zero to do with having a executable vision that creates value. Clearly shit needs to get done, but there's only so many hours in the a life of a startup and being able to see what needs to be done ultimately is more important than just getting stuff done. __ "I choose a lazy person to do a hard job. Because a lazy person will find an easy way to do it." - Bill Gates
  - amorphid 10y ago
    I do not agree. A person who doesn't work their butt off usually lacks any sort of meaningful perspective derived from hard work.
    - nxzero 10y ago
      "A shortcut is not shortcut, unless you know the way." - nxzero Finding shortcuts does not require hard work, but a willingness to be different and take risks others will not.
      - amorphid 10y ago
        "Someone else already knows the trade secret for the problem I'm trying to solve, but they won't tell me the solution, because I don't have lots of money. Even if they did tell me, I probably wouldn't understand it, because I lack the perspective of experience." -amorphid "I have no idea in which direction I need to go, so I'm gonna have to work my butt off to find the right path." -amorphid "I worked really hard, and found a solution!" -amorphid
20yrs_no_equity 10y ago
> "I will bring on talented people in executive roles who can complement me and make up for my own weaknesses, but I won't cofound again. I'd rather keep the smart, business-oriented people I know in masterminds where we can compare ideas and bounce thoughts off each other, than wade into business situations where our differences turn us into enemies and destroy the company." Absolutely. I cannot agree with this more. I don't think the issue is about visionaries vs behind-the-scenes guys. The problem is people making decisions outside their domain expertise. If you have a cofounder (eg a recent example from a company I've worked with) with no software experience his instincts are not going to serve the company well. I've seen this happen constantly, including recently with a guy who is humble, very nice, perfectly well intentioned, but has the wrong instincts and has undermined delivery of a product, probably adding 3 weeks to the development time. The people with the expertise should have authority in those domains. If your CEO/solo founder is an engineer, then the marketing and sales guys should have authority over their areas-- and be held accountable to metrics, not micro-managed. And vice versa. When you have three co-foundres you have three visions, even if they aren't visionary, and three people empowered to operate according to their vision, and it's a lot easier to just not fight over every little thing... until it blows up or you aren't executing well because you're executing at cross purposes. With a single founder you have a single authority and a single vision. And thus you can be consistent in your execution.
forgetsusername 10y ago
>We're profitable, growing, and valued at about $2.2 million. We're implementing a lot more over the course of this year and next, and I will look to exit in early 2018, once our valuation is closer to the $10 million or $20 million range If you positvely have a feature pipeline that is going to increase the value of your company ten times in less than two years, why isn't that the valuation now? Silicon Valley math gives me a headache...
- skj 10y ago
  Because no one is certain it's going to reach that valuation. The expected value (chance times possible value) is presumably what makes up the current valuation.
chenster 10y ago
> I've cofounded 4 different startups. ... Since then, I've managed my own single-founder startup." My suspicion is without the previous cofounded failed startups, unlikely you would have the success later in the game because then you know what you are doing and making up the other half by experience. Can't imagine the success rate of a first-time solofounder who makes to the other side. It's not impossible, but probably very difficult.
throwaway6565 10y ago
How long ago did you start your current one?
- throwaway7312 10y ago
  5 years. Lots of stumbling around in the dark and making dumb errors before I got serious about ramping the business up and making it a legitimate contender in its niche last year. The first 3.5 years were mostly learning the market + learning how to succeed (and how not to) in business.
mixmastamyk 10y ago
> I'd rather keep… people I know in masterminds where… What does "in masterminds" mean here?
- dhruvkar 10y ago
  not OP, but it (usually) refers to a small group of like minded individuals that bounce ideas off of each other. A more proper definition: http://www.thesuccessalliance.com/what-is-a-mastermind-group/ http://www.thesuccessalliance.com/what-is-a-mastermind-group...
raarts 10y ago
Are older single founders more likely to succeed?
- ImTalking 10y ago
  I wouldn't think so. What they gain in wisdom they lose in baggage. It's like the success rates of 2nd marriages are worse than 1st marriages. You would think that people would get smarter with their 2nd, but it's not the case.

benevol 10y ago

> pick a behind-the-scenes guy if you're a visionary, or make sure you're comfortable as the behind-the-scenes guy if you're partnering with a visionary What's your take on the situation where you are both? (Where somebody is visionary, "knows business" and codes as well.)

pyromine 10y ago
Not OP, but I'd say consider if you really are all those things. Very few people are, even Zuckerberg isn't, he was a competent coder not a great one but a visionary for sure. Ultimately no one can have it all, learn to focus on the strengths, though if truly all of those are your strengths break forward and absolutely kill it.
50CNT 10y ago
Then you don't need a co-founder. It can still be nice to have one, one guys schleps are another persons hobby. Like I'm good at analysis, but bad at dealing with third-parties. The guy I'm working with is good at dealing with third-parties but is a bit slower at dissecting problems. No worries. There's a number of different other pairings of this kind too, some areas where we have overlap, some stuff one of us needs to figure out, some both of us need to learn. And I think that's pretty cool.
- leesalminen 10y ago
  Agreed 100%. I could have started my company alone; but then I would've been stuck doing payroll, HR, mediating employee conflict and all that nonsense. My partner is a people person, and I'm not. It works out really well and my staff are happy to not have to deal with me directly (I can be a bit brash).
bsdpython 10y ago
There's simply not enough time to do all those things yourself. Find someone "good enough" in one of those areas and have them take over main responsibility.
throwaway7312 10y ago
Depends on what your end goal is and what you're starting with. If the goal is to get big and you have funds (or funding), you can be a single founder and just look for a couple of talented people, or perhaps one right-hand man, to take over the roles you're weakest in or that slow you down the most. If your goal is to get big and you don't have funds or can't attract funding, you'll probably do best to look for a cofounder who's comfortable in the behind-the-scenes roll. If you don't have money but there're two of you, and you complementary and on the same page, you'll grow a lot faster than if you don't have money but there's one of you. The situation I ran into was not having money, and having cofounders who were not on the same page with me - that kills companies. If you don't have money but just want a lifestyle business, then it's fine to be a single founder. You'll grow slower, but have freedom, and if all it's about for you is freedom then that'll be fine.

charlesdm 10y ago

> Since then, I've managed my own single-founder startup. We're profitable, growing, and valued at about $2.2 million. We're implementing a lot more over the course of this year and next, and I will look to exit in early 2018, once our valuation is closer to the $10 million or $20 million range. Did you raise any capital on that one? Or was it bootstrapped + growing?

throwaway7312 10y ago
We've taken no capital. After the experience of losing control of the cofounded businesses, the last thing I wanted was to bring in investors who'd be staring over my shoulder or telling me what to do. I'd be open to taking capital on a future project, simply because I'm experienced enough now to know what our upside is and what percentage and how much control I'd be comfortable parting with, and for how much. On this present project, I haven't even bothered to explore it, because we have our trajectory over the next 1.5 years mapped out and everything we want to do we can pay for with profits already, so there's not a lot of incentive to take months off from driving the business forward to go shopping around for investors instead.

throwaway1182 10y ago

Interesting data point. However, we're happily chugging along with 6 co-founders, bootstrapped to currently 30 mln us$ valuation and we've only just begun. Then again, your point about "visionaries" (with which you probably mean high-ego people needing a lot of approval) rings true to me. We're all pretty low-key hard-working people with a lot of self-reflection and humility - also it helps it's not the usual failing friends, family or uni buddies combo but we're really more of a casting band with a team mixed and matched from industry professionals by our main founder. In this very setup, it's actually very enjoyable with a lot of pros: Scaling is much faster and easier with invested veterans at the helm, all important departments are headed by founders, also having same-level people in the same company helps enormously with the more difficult decisions and just professional exchange, growing as leaders and 1-1 mentoring. If - and only if - the base of trust is there and continuously honed through communication, this is an amazing way to work and learn. 10/10 would do it again.

20yrs_no_equity 10y ago
You admit you have a main founder. Does this main founder have sorta ultimate authority? Or does he hold the singular original vision from which everyone else's vision/mission/purpose comes from? What's the equity split like among the 6 of you? What created that base of trust you describe? Was it everyone agreeing to follow the "main founders" vision, and him being respectful and not ego driven (so that the vision became shared?)
- throwaway1182 10y ago
  > Was it everyone agreeing to follow the "main founders" vision, and him being respectful and not ego driven (so that the vision became shared?) Pretty much exactly that plus providing the seed round. In practice, this also definitely had a lot to do with things working out well to have a center piece that's stable, predictable and a little detached, quite the opposite of a show-off. Buying into a main vision and then transferring it into a vision for tech, marketing, sales, product and operations was much easier that way. Equity split was 50:others by the way. Now you might argue this isn't a "real" as in "more equal" cofounder dynamic, but giving away 50% of your company before even starting and then treating those people as equals made a lot of difference, including an enormous buy-in at all key builders of the company. After having experienced how well it played out, I'd do it the same way.

bambax 10y ago

I have been self employed for 17 years as a 1-man consulting shop, and enjoy working alone. I have just started a product activity (making things and selling them to end-users) and can do the work by myself (I design, and then the actual making is done by factories) -- but for the first time I miss someone to talk to, someone with which to explore business ideas and options. Maybe a co-founder wouldn't help much because they would have a vested interest in the discussion, though.

sandebert 10y ago
It sounds like you might benefit from starting our joining a mastermind. Is that something you have considered? (I'm not sure how universal "mastermind" is, so here's a link to help explain it a bit, and how to run one: http://www.startupsfortherestofus.com/episodes/episode-167 http://www.startupsfortherestofus.com/episodes/episode-167)
- bambax 10y ago
  Thank you; I had never heard the term mastermind in that context before. Is it a well-known concept? The second result when googling "startup mastermind" is the post you mention, and the first one is... a reddit thread pointing to that same post. But the idea is exactly what I would need, so thanks!!
  - sandebert 10y ago
    Glad to help. I've been in one for about a year or so, and can't recommend it enough. Not sure how known the concept is, but I think it is fairly well known, especially if you run a bootstrapped startup. And if you're listening to the podcast Startups For the Rest Of Us (recommended!), I'd say it's probably close to 100 percent. One way of finding people for your mastermind is to visit the MicroConf conference, run by the same people as the podcast. (It's a lot easier getting a ticket for the European conference than the US one.)
    - gregpilling 10y ago

rsp1984 10y ago

> The problem I find (and one I've seen in a lot of cofounder groups) is that most of the people who want to start startups are visionaries. It's simpler than that. Most people just prefer slacking off to working their butts off. However it's the narcissists and sociopaths that will call their slacking off being "visionary" while the good guys either just leave or start working their butts off as everybody else. Obviously you want to pick your cofounder(s) among the latter kind.

nxzero 10y ago
Working your butt off has zero to do with having a executable vision that creates value. Clearly shit needs to get done, but there's only so many hours in the a life of a startup and being able to see what needs to be done ultimately is more important than just getting stuff done. __ "I choose a lazy person to do a hard job. Because a lazy person will find an easy way to do it." - Bill Gates
- amorphid 10y ago
  I do not agree. A person who doesn't work their butt off usually lacks any sort of meaningful perspective derived from hard work.
  - nxzero 10y ago
    "A shortcut is not shortcut, unless you know the way." - nxzero Finding shortcuts does not require hard work, but a willingness to be different and take risks others will not.
    - amorphid 10y ago
      "Someone else already knows the trade secret for the problem I'm trying to solve, but they won't tell me the solution, because I don't have lots of money. Even if they did tell me, I probably wouldn't understand it, because I lack the perspective of experience." -amorphid "I have no idea in which direction I need to go, so I'm gonna have to work my butt off to find the right path." -amorphid "I worked really hard, and found a solution!" -amorphid

20yrs_no_equity 10y ago

> "I will bring on talented people in executive roles who can complement me and make up for my own weaknesses, but I won't cofound again. I'd rather keep the smart, business-oriented people I know in masterminds where we can compare ideas and bounce thoughts off each other, than wade into business situations where our differences turn us into enemies and destroy the company." Absolutely. I cannot agree with this more. I don't think the issue is about visionaries vs behind-the-scenes guys. The problem is people making decisions outside their domain expertise. If you have a cofounder (eg a recent example from a company I've worked with) with no software experience his instincts are not going to serve the company well. I've seen this happen constantly, including recently with a guy who is humble, very nice, perfectly well intentioned, but has the wrong instincts and has undermined delivery of a product, probably adding 3 weeks to the development time. The people with the expertise should have authority in those domains. If your CEO/solo founder is an engineer, then the marketing and sales guys should have authority over their areas-- and be held accountable to metrics, not micro-managed. And vice versa. When you have three co-foundres you have three visions, even if they aren't visionary, and three people empowered to operate according to their vision, and it's a lot easier to just not fight over every little thing... until it blows up or you aren't executing well because you're executing at cross purposes. With a single founder you have a single authority and a single vision. And thus you can be consistent in your execution.

forgetsusername 10y ago

>We're profitable, growing, and valued at about $2.2 million. We're implementing a lot more over the course of this year and next, and I will look to exit in early 2018, once our valuation is closer to the $10 million or $20 million range If you positvely have a feature pipeline that is going to increase the value of your company ten times in less than two years, why isn't that the valuation now? Silicon Valley math gives me a headache...

skj 10y ago
Because no one is certain it's going to reach that valuation. The expected value (chance times possible value) is presumably what makes up the current valuation.

chenster 10y ago

> I've cofounded 4 different startups. ... Since then, I've managed my own single-founder startup." My suspicion is without the previous cofounded failed startups, unlikely you would have the success later in the game because then you know what you are doing and making up the other half by experience. Can't imagine the success rate of a first-time solofounder who makes to the other side. It's not impossible, but probably very difficult.

throwaway6565 10y ago

How long ago did you start your current one?

throwaway7312 10y ago
5 years. Lots of stumbling around in the dark and making dumb errors before I got serious about ramping the business up and making it a legitimate contender in its niche last year. The first 3.5 years were mostly learning the market + learning how to succeed (and how not to) in business.

mixmastamyk 10y ago

> I'd rather keep… people I know in masterminds where… What does "in masterminds" mean here?

dhruvkar 10y ago
not OP, but it (usually) refers to a small group of like minded individuals that bounce ideas off of each other. A more proper definition: http://www.thesuccessalliance.com/what-is-a-mastermind-group/ http://www.thesuccessalliance.com/what-is-a-mastermind-group...

raarts 10y ago

Are older single founders more likely to succeed?

ImTalking 10y ago
I wouldn't think so. What they gain in wisdom they lose in baggage. It's like the success rates of 2nd marriages are worse than 1st marriages. You would think that people would get smarter with their 2nd, but it's not the case.