> It's much more comfortable to be the person that "could be X" than to be the person that tries to actually do it.
Brilliant insight.
Reminds of me this, from Theodore Roosevelt's Citizenship in a Republic:
> It is not the critic who counts; not the man who points out how the strong man stumbles, or where the doer of deeds could have done them better. The credit belongs to the man who is actually in the arena, whose face is marred by dust and sweat and blood; who strives valiantly; who errs, who comes short again and again, because there is no effort without error and shortcoming; but who does actually strive to do the deeds; who knows great enthusiasms, the great devotions; who spends himself in a worthy cause; who at the best knows in the end the triumph of high achievement, and who at the worst, if he fails, at least fails while daring greatly, so that his place shall never be with those cold and timid souls who neither know victory nor defeat.
Expectations that we hold inside of ourselves can be a really difficult echo of identities we tried fantasizing about when growing up and as an adult. We want to do well, we want the approval, we want the validation.
The anxiety over expectations can kill you. It’s self abuse - people (investors, bosses, spouses) don’t invest in you for your anxiety driven productivity, they do it because of who you are outside of that worry. It’s hard to replace it if you consider it your motor. Let the desire to do well and good stay, but let the fear of others disappointment go, and the fantasy that we can control those outcomes by squeezing every last drop out of ourselves.
And what's interesting here (and likely in other cases) is that the expectations aren't even real. The author's investors don't even put pressure on him. Not to put too many words into the author's mouth here, but it seems like he got possessed by the "tech founder" persona. It's like he started doing things not because of his own volition but because it's the more tech foundery thing to do.
Identities shift over time whether we intend it or not. Who you were at 5, or 10 is not who you are at 20, 30, 40. We all pick up baggage, trinkets, burdens, and experiences.
One worries because it was a helpful strategy compared to not worrying, but some (like me very specifically) can get attached to that worry to the detriment of picking up other mechanisms.
It's always important to remind one's self that "who you are" is simply the story one is attached to. Things like meditation or psilocybin can help bring that to light.
It's hard being human. A lot of cognitive ability peaks before age 25[1], physical before 35[2], and to some extent it's an inexorable downward slope from there. Accumulated experience often makes up for it, but only to a point. You still won't be as good as the version of you that started earlier, or learned faster. People reach 40 and finally start exercising and eating properly and miraculously feel 25 again - there are always ways to fight it. But they'd have been even more effective with the same habits at 25.
Life is stressful. There is fear of failure, there is fear of disappointing others, and ultimately there is fear of death. And that final deadline doesn't even have the courtesy to let us know when it will come.
But many people get nothing much done without a deadline. Most get more done with some time pressure. I'm not sure how we would manage immortality. If we lived twice as long, would we work half as fast? One hopes that for a little while at least, we manage to be happy and content with what we have.
If what you value most is performing IQ tests, or competitive chess, then yes there is good data on the 25 part. If what you value is complexity and richness of thought, not so much.
Honestly if I exercised and ate perfectly from 20-29 I would've had a miserable 20s. Doing high-discipline stuff like that is way easier when you have a material reason (i.e. you've actually felt the consequences of not being fit or healthy) compared to when people just tell you "do it! you'll really thank yourself for it 20 years later!". Being in perfect physical condition at the cost of the psychological stress of forcing myself to do stuff I don't want to do every day does not sound worth it.
> Then you look around and see "startup X gets to $1M ARR a month after launch" and shit like that and I'm feeling terrible about how we're barely growing.
Comparison is the thief of joy. I fall into this trap almost weekly. Success stories are incredibly rare and we only see the splash, not the iceberg of failure just beneath the surface.
I think about my current business constantly even though on paper we are making enough to keep this thing going forever but it never feels enough.
When doing my own startup in the past, the biggest pain were: loneliness and inexplicable paranoia. Which then lead to anxiety.
This, when unchecked, can lead to self inflicted, unnecessary pressure on myself. And failure to meet the impossible deadlines, created downward spiral.
I think this is normal, everyone went through the same thing. That’s why some VCs filter for megalomaniacs, zealots, or people who have no idea what pain is, because the journey is insane arduous.
The pain magnifies if the startup is located in VHCOL. Every month a whale appears and eat a big chunk of your runway. Who wouldn’t have anxiety?
- I had no idea what / why I should use it so I looked at the demo video and it didn't seem to solve any particular use case for any particular problem, it was more a ,,config'' video instead of a demo video
- From reading the (quite interesting) article it seemed like you are focusing on pivoting instead of iteration speed. Have you tried for example to just query an LLM to build the whole project that you have done? How much time would be to vibe code it?
I know that HN is mostly against vibe coding, but if the project could have been created in 1-3 days and you took 3 month, that's a bigger issue than growth itself. In that case the metric that should be looked at is iteration speed instead of just growth (both are super important though!)
Genuinely curious, can I ask why this is relevant to point out? This seems like just a general blog post, about raising money for a startup and personal reflections on it. Why would a link to a github repo be an important part of that?
It's just part of both getting feedback and general sales.
For engineers it feels too pushy / not genuine, but after spending time / effort on a great non-generated interesting article, inserting a link for people who want to check it out isn't pushy.
> The thing is: it's a lot easier to live your life thinking you could have done X if you wanted to, than to "disappoint" these people that believed in you by trying and failing. You can always lean on this idea in your head of what you could have been, and how everyone believed in you so it must be true, but you just chose not to follow that path.
sometimes the best decision is the one you don't take.
Without trying to be glib about it, this post sounds like a description of second-system syndrome, applied to entrepreneurship. It happens to all of us.
Thank-you! It is great to read a honest and self-aware journal covering this.
As someone who fantasizes about running my own thing, working for a few start-ups have made me very stringent on what my requirements are for starting something (co-founders, investment, location, market). And also that these requirements have become so very risk-averse that I probably am not the personality profile to run a business! Nevermind the endless imposter syndrome.
I think everyone would seriously benefit from learning poker. I used to play professionally and the idea of looking at things as probabilistic bets, and in terms of expected value is so deeply rooted in my mind
Investments are bets. Most sane investors aren't putting it all on one thing
Startups are bets
Applying for jobs. Sales. Dating. Health. Basically everything
You risk $X money and time for a payoff of $Y that comes Z%
You can make the best decision and have a bad outcome because there are so many unknowns. This isn't chess
You can play everything wrong and still hit it out of the park
I mean this is one of the range of outcomes that could've happened. You can't declare yourself a success or failure from one project
Just keep making good decisions and don't risk it all, and you'll more than likely end up fine
I read about mathematical expectation in a poker book for the first time a long time ago and it's really an interesting way to think about the world. In real life, it's a bit different though since there are other factors than just raw percentages like poker hands. For example, you could do everything right and still fail while someone else (like a nepo hire) can do everything wrong and still succeed.
No, that's not what I meant. I meant more like you could flop a high probability draw that does get there on the river, but the nepo kid still wins even though they just had one pair.
In poker, there are rules everyone has to follow. In real life, the rules can differ from person to person. Hence, the odds are rigged.
> You risk $X money and time for a payoff of $Y that comes Z%
Unlike in poker where you know those 3 numbers if you are paying attention, in real life you know only X, and sometimes not even that. The rest is a guessing game, and that estimation is the hard part.
If you want me to ruin this for you, look up Bertrand's Paradox and The Problem Of Priors.
I recently had to deal with this, ugh, I just pick a prior or two and see what the outcome looks like. I'm not sure we can calculate probability of success, but rather use probability to find losing ideas that should never be done.
Well written. One interesting pattern in founders I've been thinking about recently is how early you encounter major blockers, and how that shapes your self worth.
Having a strong product and being unable to raise feels like shit, early users may validate you're solving a problem but it may not make sense to investors.
Having an early raise is a very positive signal, I can only imagine you're perceived trajectory coming out of that. Being unable to settle on a problem also sucks in a different way.
Regardless of what camp you're in I feel the take-away is you need to focus on reflecting inwards. Be better than you were yesterday, not better than someone's projections on LinkedIn.
Hey, author here. Totally agree on how helpful these people are. I have a psychologist and also some great mentors. This doesn't make you immune to things like I wrote about but helps you process and get over them when they happen.
As a side note, I'm in a much better mental space now, largely due to facing these things straight on. Things are good, and I'm motivated and sharp!
This is exactly why I've avoided raising so far. Not because VC money is bad - obviously it enables things that wouldn't otherwise be possible - but because I know myself well enough to recognise I'd react exactly like this.
The author nails it: "I started to actually operate in a way that is counterproductive for my startup, while thinking I was actually doing what was best." That's the dangerous part. The pressure doesn't announce itself as pressure. It masquerades as ambition, urgency, drive.
Bootstrapping has its own version of this though. Instead of investor expectations, you've got the slow burn of "am I wasting years of my life on something that needs capital to work?" The grass is always greener. At least with VC money, you can move fast and find out if you're wrong. With bootstrapping, you can spend 3 years proving out something that would have taken 6 months with proper funding.
Neither path is inherently better. But knowing which one will fuck with your head less is worth figuring out before you're in the middle of it.
If they hadn't taken the money, what would the counterfactual article have said?
Everybody creates narritives and belief-systems, where causes and effects seem so clear.
Perhaps I'm far too skeptical about their self-analysis. I've met very few people where their own analysis about themselves has matched what I have read in them. So many people misread their own minds and emotional drives. So I have learnt to cynically look for excuses and rationalisations and justifications.
The article is brilliant because we too rarely hear about people's doubts and negatives.
Some people (whether successful or not) do know themselves, but it is uncommon in my experience.
I helped bootstrap a business and we were in an incubator. There I saw some of the side-effects on businesses and founders from taking investment. We were just lucky that we couldn't be bothered with doing the distracting pony-show to get an investor onboard: we would have taken investment if it weren't so costly to do so.
With boot strapping at least you can de risk with consulting/freelancing. And I think with the new generation of software development tools it’s much easier to validate the core business problems without grinding out code for weeks on end.
I have a few 1099 MBA advisors that I call Chief of Staff. I check my questions against what they think. When you get 3 MBAs with engineering, finance, or CS degrees agreeing independently, it bumps up confidence.
I think this is a case where this helps considerably. Its essentially the 'consulting' thing for small businesses.
Dont worry pal for the investors you are a bet. They have many bets and they expect most to lose and one to win big. It is wrong to think that not turning $1m into $100m or $1bn is letting someone down.
Be the bet. Do your thing and you might be right. They dont need you to make a sale tomorrow.
Nothing about this struck me as a sign that money wasn’t well-invested. From the headline, I was picturing “we raised and then I blew it in Vegas”.
Nothing wrong with admitting to uncertainty and insecurity. I mean, there are two types of people — those who suffer doubt sometimes, and those who don’t admit it. Give me the first kind any time.
Then I know they are capable of deep self-reflection. A good thing. Any founder without such thoughts and some point or another is either lying to you or will eventually fail big time.
Brilliant insight.
Reminds of me this, from Theodore Roosevelt's Citizenship in a Republic:
> It is not the critic who counts; not the man who points out how the strong man stumbles, or where the doer of deeds could have done them better. The credit belongs to the man who is actually in the arena, whose face is marred by dust and sweat and blood; who strives valiantly; who errs, who comes short again and again, because there is no effort without error and shortcoming; but who does actually strive to do the deeds; who knows great enthusiasms, the great devotions; who spends himself in a worthy cause; who at the best knows in the end the triumph of high achievement, and who at the worst, if he fails, at least fails while daring greatly, so that his place shall never be with those cold and timid souls who neither know victory nor defeat.
Good luck, and go get 'em.
The anxiety over expectations can kill you. It’s self abuse - people (investors, bosses, spouses) don’t invest in you for your anxiety driven productivity, they do it because of who you are outside of that worry. It’s hard to replace it if you consider it your motor. Let the desire to do well and good stay, but let the fear of others disappointment go, and the fantasy that we can control those outcomes by squeezing every last drop out of ourselves.
One worries because it was a helpful strategy compared to not worrying, but some (like me very specifically) can get attached to that worry to the detriment of picking up other mechanisms.
Life is stressful. There is fear of failure, there is fear of disappointing others, and ultimately there is fear of death. And that final deadline doesn't even have the courtesy to let us know when it will come.
But many people get nothing much done without a deadline. Most get more done with some time pressure. I'm not sure how we would manage immortality. If we lived twice as long, would we work half as fast? One hopes that for a little while at least, we manage to be happy and content with what we have.
[1] https://pmc.ncbi.nlm.nih.gov/articles/PMC4441622/
[2] https://pubmed.ncbi.nlm.nih.gov/17717011/
Comparison is the thief of joy. I fall into this trap almost weekly. Success stories are incredibly rare and we only see the splash, not the iceberg of failure just beneath the surface.
I think about my current business constantly even though on paper we are making enough to keep this thing going forever but it never feels enough.
I felt this post and appreciate the honesty.
-- Kahlil Gibran
This, when unchecked, can lead to self inflicted, unnecessary pressure on myself. And failure to meet the impossible deadlines, created downward spiral.
I think this is normal, everyone went through the same thing. That’s why some VCs filter for megalomaniacs, zealots, or people who have no idea what pain is, because the journey is insane arduous.
The pain magnifies if the startup is located in VHCOL. Every month a whale appears and eat a big chunk of your runway. Who wouldn’t have anxiety?
- It was easier to find a link to where you worked at than your repo (https://github.com/skaldlabs/skald?tab=readme-ov-file), you should have linked it visibly
- I had no idea what / why I should use it so I looked at the demo video and it didn't seem to solve any particular use case for any particular problem, it was more a ,,config'' video instead of a demo video
- From reading the (quite interesting) article it seemed like you are focusing on pivoting instead of iteration speed. Have you tried for example to just query an LLM to build the whole project that you have done? How much time would be to vibe code it?
I know that HN is mostly against vibe coding, but if the project could have been created in 1-3 days and you took 3 month, that's a bigger issue than growth itself. In that case the metric that should be looked at is iteration speed instead of just growth (both are super important though!)
Genuinely curious, can I ask why this is relevant to point out? This seems like just a general blog post, about raising money for a startup and personal reflections on it. Why would a link to a github repo be an important part of that?
For engineers it feels too pushy / not genuine, but after spending time / effort on a great non-generated interesting article, inserting a link for people who want to check it out isn't pushy.
sometimes the best decision is the one you don't take.
As someone who fantasizes about running my own thing, working for a few start-ups have made me very stringent on what my requirements are for starting something (co-founders, investment, location, market). And also that these requirements have become so very risk-averse that I probably am not the personality profile to run a business! Nevermind the endless imposter syndrome.
Investments are bets. Most sane investors aren't putting it all on one thing
Startups are bets
Applying for jobs. Sales. Dating. Health. Basically everything
You risk $X money and time for a payoff of $Y that comes Z%
You can make the best decision and have a bad outcome because there are so many unknowns. This isn't chess
You can play everything wrong and still hit it out of the park
I mean this is one of the range of outcomes that could've happened. You can't declare yourself a success or failure from one project
Just keep making good decisions and don't risk it all, and you'll more than likely end up fine
Life's odds are rigged.
> you could do everything right and still fail
Sometimes even a high probability draw doesn't get there on the river.
> while someone else (like a nepo hire) can do everything wrong and still succeed
Some people always start with pairs, Axs, or suited connectors.
In poker, there are rules everyone has to follow. In real life, the rules can differ from person to person. Hence, the odds are rigged.
Unlike in poker where you know those 3 numbers if you are paying attention, in real life you know only X, and sometimes not even that. The rest is a guessing game, and that estimation is the hard part.
Even if your estimates have large error bars, it can still be a good bet if you believe it’s +EV and have a large enough bankroll.
I recently had to deal with this, ugh, I just pick a prior or two and see what the outcome looks like. I'm not sure we can calculate probability of success, but rather use probability to find losing ideas that should never be done.
Having a strong product and being unable to raise feels like shit, early users may validate you're solving a problem but it may not make sense to investors.
Having an early raise is a very positive signal, I can only imagine you're perceived trajectory coming out of that. Being unable to settle on a problem also sucks in a different way.
Regardless of what camp you're in I feel the take-away is you need to focus on reflecting inwards. Be better than you were yesterday, not better than someone's projections on LinkedIn.
As a side note, I'm in a much better mental space now, largely due to facing these things straight on. Things are good, and I'm motivated and sharp!
The author nails it: "I started to actually operate in a way that is counterproductive for my startup, while thinking I was actually doing what was best." That's the dangerous part. The pressure doesn't announce itself as pressure. It masquerades as ambition, urgency, drive.
Bootstrapping has its own version of this though. Instead of investor expectations, you've got the slow burn of "am I wasting years of my life on something that needs capital to work?" The grass is always greener. At least with VC money, you can move fast and find out if you're wrong. With bootstrapping, you can spend 3 years proving out something that would have taken 6 months with proper funding.
Neither path is inherently better. But knowing which one will fuck with your head less is worth figuring out before you're in the middle of it.
If they hadn't taken the money, what would the counterfactual article have said?
Everybody creates narritives and belief-systems, where causes and effects seem so clear.
Perhaps I'm far too skeptical about their self-analysis. I've met very few people where their own analysis about themselves has matched what I have read in them. So many people misread their own minds and emotional drives. So I have learnt to cynically look for excuses and rationalisations and justifications.
The article is brilliant because we too rarely hear about people's doubts and negatives.
Some people (whether successful or not) do know themselves, but it is uncommon in my experience.
I helped bootstrap a business and we were in an incubator. There I saw some of the side-effects on businesses and founders from taking investment. We were just lucky that we couldn't be bothered with doing the distracting pony-show to get an investor onboard: we would have taken investment if it weren't so costly to do so.
Money and ownership causes weird pressures.
I think this is a case where this helps considerably. Its essentially the 'consulting' thing for small businesses.
Be the bet. Do your thing and you might be right. They dont need you to make a sale tomorrow.
Nothing wrong with admitting to uncertainty and insecurity. I mean, there are two types of people — those who suffer doubt sometimes, and those who don’t admit it. Give me the first kind any time.