I left a 6 figure engineering job to build my own startup with my wife. For the past 5 years, we spent 2/3rds of our savings on it and almost didn’t take vacation. This year we finally reached ramen profitability.
When I look at where we would be if I had kept the job, we would be homeowners, be able to buy new clothes regularly, go to restaurants and take awesome vacations a few times a year.
But the missing thing would be autonomy. The reason why I’m willing to sacrifice so much is because i fundamentally don’t like having to follow orders from a boss or manager. I’m arrogant enough to think i know better, and want to prove it by actually building my own thing.
Regardless of how silly it sounds on a financial level, the calculation makes sense once we look at the sense of ownership and autonomy over our own work. It’s worth more to me than any money I could make.
Hi, I just wanted to say congrats, your site and service looks very nice, proposition is clear, there is a spin which makes it different from other design agencies and I like the pricing tier setup, it makes sense (for me)! Made a bookmark for when this will come handy in the future.
I've been following you for quite some time now, and I really appreciate the honesty and the way you share both the ups and downs of running your own small business.
On the building side of things, the main challenge is designing all the logos, my wife designed more than 800 so far. (almost every other logo generator site use existing icon libraries)
It took a bit more than a year to have enough logos to launch, design the product and code the platform. In part because we were such perfectionists (which we aren't as much anymore).
But launching was only the beginning, and soon the real challenge presented itself: how to find customers. Had to figure out a distribution and marketing strategy which we had no experience with, all the while improving the product. And this is why it's now been 5 years.
This is really cool. I'm in the branding phase of an app on the side at the moment, and I absolutely loathe trying to pin down the name and the logo because it is dark alley after dark alley until you reach some okay-enough state to launch with.
This is exactly why we built this. Allows you to get a professional branding to start with even on low budget. Then you can go ahead and launch, validate your product, and come back to get custom work done when you need it / can budget for it.
It’s an interesting article. In my view, Non-conformists start companies. Possibly aggressive non-conformists most of all.
In my personal case, I made many questionable choices, including turning down a job at Microsoft in the nineties (would have been better financially) and leaving multiple great jobs (one of which afforded me corporate apartments in Honolulu and London) to risk everything multiple times to start multiple companies.
So there’s risk-seeking behavior there as well as a refusal to accept “good enough” even when it was almost definitely a better choice from a financial and physical health perspective.
I can still see my dad shaking his head about turning down Microsoft…
It sort of worked out. I had a good exit but nothing like kicking it at M$ for 30 years would have been.
I’m not sure we why we glamorize this. But in the end I wouldn’t change it. I did it my way. I’m now trying to do it again.
This is why I can’t play any games which require grinding (looking at you Eve) because I know it’s more fun IRL. ¯\_(ツ)_/¯
Not especially non-conformists - non-conformity is merely a symptom.
As you say, risk seeking behavior, resulting from the actual cause: "poor risk assessment" - ties right in to difficult childhood, mental health issues, and the market misjudging you (all causes or signs of trauma and being outside the norm).
I say this as someone with an appetite for trying new things, being non-conformist, and adventure sports - clearly the accuracy or the precision of my risk assessment model is significantly outside the norm!
People with excellent and accurate risk estimation and assessment work as actuaries, or accountants, certain kinds of insurance brokers, something nice and safe where you can do good work for 35 years and retire. The quintessential "brown volvo" driver.
Now, I personally think those people are rather safe and uninteresting - but then we've already established I'm probably not the person to base your decisions on!
At age 6, I was tested for my tendency towards risk aversion. I scored as high as possible in risk aversion; in other words, I was extremely risk-averse, as my parents worried. That tendency marked a better part of my life, and it brought forth/was comorbid with GAD and generalized depression. All of those things make you think that if you just had more control you would feel better, but the grasping for it only exacerbates the symptoms.
Now I'm 41, and am really interested in bootstrapping (I have made one small app, working on the next). In particular, I love the risk/reward calculus especially. I've gradually awoken to the amount of value I bring via programming and strategy versus the salary structure in place at a lot of companies. This year I'm focusing on amassing leverage in several forms, be that a more public voice, a more fit body, additional income streams (however small), etc. (Typical midlife stuff, yes.)
In my experience, most successful entrepreneurs are usually quite good at accurately assessing risks. They are simply more capable and willing to embrace certain risks in pursuit of greater rewards in the future.
>As you say, risk seeking behavior, resulting from the actual cause: "poor risk assessment" -
You project value judgement into places where there need not be any. Most of these people who are doing "entrepreneurial things" come out somewhat ahead over their careers. It's not like they're dying destitute. Do they (in aggregate) come out as far ahead in terms of dollars as someone who grinds leet code and job hops between BigcCo? Probably not. But that's not what they're optimizing for.
> ties right in to difficult childhood, mental health issues, and the market misjudging you (all causes or signs of trauma and being outside the norm).
Ah, yes, the ol' anyone who doesn't agree with you must have something "wrong with them" or "be damaged" line of reasoning.
>I say this as someone with an appetite for trying new things, being non-conformist, and adventure sports -
Having a hobby that might put you in a cast isn't the kind of risk being discussed here. It's misleading (to be charitable) to portray that kind of risk exposure as analogous to doing things that will have large impact on your earning potential in the short, medium and long term.
>People with excellent and accurate risk estimation and assessment work as actuaries, or accountants, certain kinds of insurance brokers, something nice and safe where you can do good work for 35 years and retire. The quintessential "brown volvo" driver.
You are conflating loss avoidance with risk assessment.
And I say this as someone who is living the exact career you are trying to stereotype in a positive light.
>
People with excellent and accurate risk estimation and assessment work as actuaries, or accountants, certain kinds of insurance brokers, something nice and safe where you can do good work for 35 years and retire. The quintessential "brown volvo" driver.
To work as an actuary, it is better if you are rather on the risk-averse side (i.e. err into this direction instead of having a tendency for excellent and accurate risk estimation) because insurance companies and regulatory authorities are very biased into this direction.
> This is why I can’t play any games which require grinding (looking at you Eve) because I know it’s more fun IRL. ¯\_(ツ)_/¯
This realization almost permanently put me off most online video games. Most team-based games are made such that one individual can't swing the game too much, because that's seen as bad. Thus only about 20-30% of games you can directly impact, thus you're mainly just burning time with limited agency for player skill. MMORPGs are timesinks first and foremost, rather than skill-based games.
I replaced them (mostly) with music. Music has an infinite skill ceiling that is apparent, it is cooperative, creative, and tends to have people that want to be there, versus people who are there because they don't have anything better to do.
Have to throw a good mention of Dark Souls here. The vibes, the story, and the themes resonate deeply with me and connect naturally with the highs and lows of entrepreneurship.
Had to chime in here RE: music. When I encounter people that wish they could play guitar/piano/etc and say "they have no time", but then I find out they play games for hours per day. Well... priorities right?
(I hardly play games anymore)
"including turning down a job at Microsoft in the nineties
I can still see my dad shaking his head about turning down Microsoft…"
That was quite a while ago... Probably should forgive and forget that one. Forgiving the disappointment makes mental space for new opportunities.
I agree non-conformists start the really visible flashy companies. A new aircraft maintenance company can make bank, but it doesn't really grab headlines.
My experience: Psychological orphans with a basic income.
"Psychological orphans" i.e. kids who had shitty parents and learned to adapt to survive. Then this behavior became a habit and a game.
"Basic income" i.e. kids from middle and upper middle class backgrounds so there was no food poverty in the family and long term thinking was possible by the kid, even in the context of the dysfunctional setting.
The above is true for me and all of the high growth tech founders I know on a very personal level (could be selection bias in who I connect deeply with though).
My recipe for tech startup founder includes:
1. You were one of the smartest kids at your private school—so you’re opinionated and confident
2. You’re some kind of social misfit with a chip on your shoulder
3. Father is an Engineer, Lawyer, Banker, Doctor
4. Got some private tutoring or coaching at a young age
5. Went to a fancy big-name college
It doesn’t apply to everyone, but during a recent job search I did a little detective work on founders at jobs I was applying for, and this was the large majority of them
Wow, that's a really interesting observation and describes me perfectly. I wouldn't consider myself a "real" entrepreneur, but I've always had a side hustle and I own some rental properties.
I took me until the age of 34 and having kids of my own to realize that my childhood wasn't that great, and that a parent's role should extend beyond just feeding their kids. My upbringing made my hyper-independent, so the desire to make myself completely financially independent basically consumed by 20s. It took me a long time to realize this drive, while useful in my career, came from a very unhealthy place.
Yea, I definitely have seen this same pattern, nice description.
Though there is the "upper class" founder background that still had shitty parents and something to prove, and often they can get really far because of the $ and connections, though often have the issue that their alternative life is a bit "too easy" so they don't execute hard enough / close enough, or they just give up.
Another correlation, very unusual and interesting, is that past infection with Toxoplasmosis (a parasite that grows in cat poop) increases the chances of becoming an entrepreneur by a factor of 1.27 to 2
> they discovered that those infected with the parasite Toxoplasma gondii were, on average, 29% more likely than others to have founded a start-up, 27% more likely to have founded multiple ventures, and more than twice as likely to have founded their businesses alone
Along with an increased risk of death via car accidents, having contracted Toxoplasmosis seems to precipitate risk seeking behaviors, similar to its intended evolutionary prerogative: the infection makes rats sexually aroused by the smell of cat urine, so they seek the smell, where cats are more likely to be around, are eaten by cats, and the cycle continues.
I'm just guessing, but I think you'll find an even stronger correlations from Toxoplasmosis to the lack of traditional family obligations, and also the latter to entrepreneurship.
Working on my second startup. I have clinical depression, ADHD and OCD.
The depression is an endless battle through a muddy swamp. I have to endlessly game it with exercise, sleep, supplements. I would give anything to not be held back by that.
I somewhat envy the manic benefits of Bipolar! That sounds so much better than just regular depression! /h
But my ADHD is high functioning. My mind constantly jumps from topic to topic, every aspect of a problem, or any problem in my life, or anticipated future life. And my brain tracks all these puzzle pieces well. It is my counter-point to focusing!
And OCD works for me too. I think it is what makes my ADHD work for me. Always fixing, improving, smoothing, organizing. I can get distracted rearranging books on a shelf, but even then its like meditation, my zen, in that even small positive changes to my environment motivate me out of depression.
Also, the constant ADHD/OCD iterations over the smallest things, leads me to fluency with my projects that invariably lead to the bigger novel insights that make all the difference.
You can't run around the base of a huge mountain like a madman, testing every possible crevice, accumulating every possible strategy, practicing every kind of traversal, and acquiring every piece of equipment, without finding a way up! Even if I can't describe to anyone whether I am making any progress at all until I do!
The downside of ADHD is very real for me: "less skilled at necessary tasks like accounting and bookkeeping" is an understatement. I can keep my regular life on rails, or get work done. Unfortunately, not both.
I feel you. Depression and ADHD is what I credit for my 'independent work personality' a burnout was what made me quit the job I always wanted about 8 years ago. And 3 'companies' later my main pain in life is bookkeeping.
I am not risk seeking, but definitely a non conformist. I think the main thing that drove me to be entrepreneural is the lack of a choice, for not 99% properly working people, in the traditional working market.
"In pursuit of that subject, we’ve studied companies from around the world, across industries, and at different stages of maturation, hopping from Starbucks to Stripe, Y Combinator to Flexport, Rappi to Kaspi, and DST to TSMC."
A curious sample. Unfortunately these types of "studies" omit the bulk of entrepreneurs that keep an economy running. Small businesses, 5-50 employees, that tick on without the glory and fame that outliers capture are more interesting and more likely to be achieved. Would be curious to see more studies about the types of entrepreneurs that build them.
It might be the actual research is more diverse, but they plucked out examples that were more likely to get people interested. Bob's Extruding in Elbow, Alabama might be a key plastic component supplier for the global economy, but nobody's heard of it.
No, you can look at all their briefings here: https://www.generalist.com/briefings. They don't really branch out beyond software startups and big businesses, and don't seem to be interested in smaller-scale entrepreneurship.
Well naturally since all these papers are focused on lottery wining tickets. Running a small to medium sized business is far more relevant to most of us.
The nice thing about this article is it blows some ageist assumptions out of the water. I wasn’t expecting the average founders age to be over 40 in SV.
I learned that a couple months ago and was shocked as well. It could also be a symptom of ageism in the industry: as it becomes harder for those not attracted by the corporate ladder to be hired, they start a business.
I am almost here. Similar age and in a company planing 2nd round of layoffs. I really have no delusions that somebody will want to hire me again. Universities are pumping out thousands of cheaper and better looking graduates. I never saw big corp hiring (in Germany) a graybeard like me for developer role. All the graybeards were so called consultants hired over specific agency. 40 is the magic number I guess.
On the other hand 40 is about the right time, because body and mind is still functional. The network is available and the people skills should be developed even in worst outcasts (there are exceptions). People often have some business ideas and the worthy ones are developed a bit as a hobby. Being fired is the so much needed kick to get started for real.
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When I look at where we would be if I had kept the job, we would be homeowners, be able to buy new clothes regularly, go to restaurants and take awesome vacations a few times a year.
But the missing thing would be autonomy. The reason why I’m willing to sacrifice so much is because i fundamentally don’t like having to follow orders from a boss or manager. I’m arrogant enough to think i know better, and want to prove it by actually building my own thing.
Regardless of how silly it sounds on a financial level, the calculation makes sense once we look at the sense of ownership and autonomy over our own work. It’s worth more to me than any money I could make.
Ps: if you’re curious, the startup is logology.co
I find it very interesting that you value 'any startup' more than owning your own flat for example
It took a bit more than a year to have enough logos to launch, design the product and code the platform. In part because we were such perfectionists (which we aren't as much anymore).
But launching was only the beginning, and soon the real challenge presented itself: how to find customers. Had to figure out a distribution and marketing strategy which we had no experience with, all the while improving the product. And this is why it's now been 5 years.
Because making is not selling.
This is why I do it as well, at least in part. The other part is that I get to control what projects I get to work on.
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Took us 6 years, we are revenue positive.
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In my personal case, I made many questionable choices, including turning down a job at Microsoft in the nineties (would have been better financially) and leaving multiple great jobs (one of which afforded me corporate apartments in Honolulu and London) to risk everything multiple times to start multiple companies.
So there’s risk-seeking behavior there as well as a refusal to accept “good enough” even when it was almost definitely a better choice from a financial and physical health perspective.
I can still see my dad shaking his head about turning down Microsoft…
It sort of worked out. I had a good exit but nothing like kicking it at M$ for 30 years would have been.
I’m not sure we why we glamorize this. But in the end I wouldn’t change it. I did it my way. I’m now trying to do it again.
This is why I can’t play any games which require grinding (looking at you Eve) because I know it’s more fun IRL. ¯\_(ツ)_/¯
As you say, risk seeking behavior, resulting from the actual cause: "poor risk assessment" - ties right in to difficult childhood, mental health issues, and the market misjudging you (all causes or signs of trauma and being outside the norm).
I say this as someone with an appetite for trying new things, being non-conformist, and adventure sports - clearly the accuracy or the precision of my risk assessment model is significantly outside the norm!
People with excellent and accurate risk estimation and assessment work as actuaries, or accountants, certain kinds of insurance brokers, something nice and safe where you can do good work for 35 years and retire. The quintessential "brown volvo" driver.
Now, I personally think those people are rather safe and uninteresting - but then we've already established I'm probably not the person to base your decisions on!
If people are interested, there are good psychological tests for risk assessment skills - https://en.wikipedia.org/wiki/Impulsivity#Assessment_of_impu...
At age 6, I was tested for my tendency towards risk aversion. I scored as high as possible in risk aversion; in other words, I was extremely risk-averse, as my parents worried. That tendency marked a better part of my life, and it brought forth/was comorbid with GAD and generalized depression. All of those things make you think that if you just had more control you would feel better, but the grasping for it only exacerbates the symptoms.
Now I'm 41, and am really interested in bootstrapping (I have made one small app, working on the next). In particular, I love the risk/reward calculus especially. I've gradually awoken to the amount of value I bring via programming and strategy versus the salary structure in place at a lot of companies. This year I'm focusing on amassing leverage in several forms, be that a more public voice, a more fit body, additional income streams (however small), etc. (Typical midlife stuff, yes.)
You project value judgement into places where there need not be any. Most of these people who are doing "entrepreneurial things" come out somewhat ahead over their careers. It's not like they're dying destitute. Do they (in aggregate) come out as far ahead in terms of dollars as someone who grinds leet code and job hops between BigcCo? Probably not. But that's not what they're optimizing for.
> ties right in to difficult childhood, mental health issues, and the market misjudging you (all causes or signs of trauma and being outside the norm).
Ah, yes, the ol' anyone who doesn't agree with you must have something "wrong with them" or "be damaged" line of reasoning.
>I say this as someone with an appetite for trying new things, being non-conformist, and adventure sports -
Having a hobby that might put you in a cast isn't the kind of risk being discussed here. It's misleading (to be charitable) to portray that kind of risk exposure as analogous to doing things that will have large impact on your earning potential in the short, medium and long term.
>People with excellent and accurate risk estimation and assessment work as actuaries, or accountants, certain kinds of insurance brokers, something nice and safe where you can do good work for 35 years and retire. The quintessential "brown volvo" driver.
You are conflating loss avoidance with risk assessment.
And I say this as someone who is living the exact career you are trying to stereotype in a positive light.
To work as an actuary, it is better if you are rather on the risk-averse side (i.e. err into this direction instead of having a tendency for excellent and accurate risk estimation) because insurance companies and regulatory authorities are very biased into this direction.
This realization almost permanently put me off most online video games. Most team-based games are made such that one individual can't swing the game too much, because that's seen as bad. Thus only about 20-30% of games you can directly impact, thus you're mainly just burning time with limited agency for player skill. MMORPGs are timesinks first and foremost, rather than skill-based games.
I replaced them (mostly) with music. Music has an infinite skill ceiling that is apparent, it is cooperative, creative, and tends to have people that want to be there, versus people who are there because they don't have anything better to do.
Have to throw a good mention of Dark Souls here. The vibes, the story, and the themes resonate deeply with me and connect naturally with the highs and lows of entrepreneurship.
That was quite a while ago... Probably should forgive and forget that one. Forgiving the disappointment makes mental space for new opportunities.
I agree non-conformists start the really visible flashy companies. A new aircraft maintenance company can make bank, but it doesn't really grab headlines.
Eve actually broke my desire to play a lot of games for this exact reason.
At least I have idle games and I'm also working on one which will probably end up in nothing.
"Psychological orphans" i.e. kids who had shitty parents and learned to adapt to survive. Then this behavior became a habit and a game.
"Basic income" i.e. kids from middle and upper middle class backgrounds so there was no food poverty in the family and long term thinking was possible by the kid, even in the context of the dysfunctional setting.
The above is true for me and all of the high growth tech founders I know on a very personal level (could be selection bias in who I connect deeply with though).
My recipe for tech startup founder includes: 1. You were one of the smartest kids at your private school—so you’re opinionated and confident 2. You’re some kind of social misfit with a chip on your shoulder 3. Father is an Engineer, Lawyer, Banker, Doctor 4. Got some private tutoring or coaching at a young age 5. Went to a fancy big-name college
It doesn’t apply to everyone, but during a recent job search I did a little detective work on founders at jobs I was applying for, and this was the large majority of them
I took me until the age of 34 and having kids of my own to realize that my childhood wasn't that great, and that a parent's role should extend beyond just feeding their kids. My upbringing made my hyper-independent, so the desire to make myself completely financially independent basically consumed by 20s. It took me a long time to realize this drive, while useful in my career, came from a very unhealthy place.
Though there is the "upper class" founder background that still had shitty parents and something to prove, and often they can get really far because of the $ and connections, though often have the issue that their alternative life is a bit "too easy" so they don't execute hard enough / close enough, or they just give up.
https://hbr.org/2022/07/a-common-parasite-can-make-people-mo...
> they discovered that those infected with the parasite Toxoplasma gondii were, on average, 29% more likely than others to have founded a start-up, 27% more likely to have founded multiple ventures, and more than twice as likely to have founded their businesses alone
Along with an increased risk of death via car accidents, having contracted Toxoplasmosis seems to precipitate risk seeking behaviors, similar to its intended evolutionary prerogative: the infection makes rats sexually aroused by the smell of cat urine, so they seek the smell, where cats are more likely to be around, are eaten by cats, and the cycle continues.
Toxoplasma affects dopamine metabolism - body starts to produce more of it.
Dopamine is also released with alcohol intake, notice that alcohol also makes everyone more confident, attractive and, well, prone to car accidents.
I guess the "rough childhood" also has something to do with alcohol or other drugs somehow, that means dopamine metabolism is also affected.
Dopamine is a powerful thing.
The depression is an endless battle through a muddy swamp. I have to endlessly game it with exercise, sleep, supplements. I would give anything to not be held back by that.
I somewhat envy the manic benefits of Bipolar! That sounds so much better than just regular depression! /h
But my ADHD is high functioning. My mind constantly jumps from topic to topic, every aspect of a problem, or any problem in my life, or anticipated future life. And my brain tracks all these puzzle pieces well. It is my counter-point to focusing!
And OCD works for me too. I think it is what makes my ADHD work for me. Always fixing, improving, smoothing, organizing. I can get distracted rearranging books on a shelf, but even then its like meditation, my zen, in that even small positive changes to my environment motivate me out of depression.
Also, the constant ADHD/OCD iterations over the smallest things, leads me to fluency with my projects that invariably lead to the bigger novel insights that make all the difference.
You can't run around the base of a huge mountain like a madman, testing every possible crevice, accumulating every possible strategy, practicing every kind of traversal, and acquiring every piece of equipment, without finding a way up! Even if I can't describe to anyone whether I am making any progress at all until I do!
The downside of ADHD is very real for me: "less skilled at necessary tasks like accounting and bookkeeping" is an understatement. I can keep my regular life on rails, or get work done. Unfortunately, not both.
I am not risk seeking, but definitely a non conformist. I think the main thing that drove me to be entrepreneural is the lack of a choice, for not 99% properly working people, in the traditional working market.
A curious sample. Unfortunately these types of "studies" omit the bulk of entrepreneurs that keep an economy running. Small businesses, 5-50 employees, that tick on without the glory and fame that outliers capture are more interesting and more likely to be achieved. Would be curious to see more studies about the types of entrepreneurs that build them.
Well naturally since all these papers are focused on lottery wining tickets. Running a small to medium sized business is far more relevant to most of us.
There are many folks with side businesses that compliment their incomes, but primarily it is a tax strategy driven investment decision process.
I think most successful "entrepreneurs" clue into the pejorative connotation of the word sooner. =)
On the other hand 40 is about the right time, because body and mind is still functional. The network is available and the people skills should be developed even in worst outcasts (there are exceptions). People often have some business ideas and the worthy ones are developed a bit as a hobby. Being fired is the so much needed kick to get started for real.
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