That was the part that stood out for me as well.

I know people who have talked that talk, never dared walk it. I am happy with myself that I have walked that walk—many times. Most of the time they have not ended up how I had hoped they would in my imagination. Other times, they did. Regardless, in all cases, I am not left here now wondering what would have happened if…

Getting a game I wrote published in 1989 or so was one that worked out. Hitchhiking from Alaska back to the Lower-48 when the salmon season closed was another.

Quitting Apple to write games for the iPhone was a big fail. When I realized it though I applied and was hired back at Apple. Until that little experiment though I had been watching apps skyrocket to the top-10 while I unable to submit an app of my own (Apple policy, of course).

I had an idea for a great fantasy novel in my head for years. Only when I finally forced myself to start to write it did I realize I really didn't have an idea for a great fantasy novel. I had part of an idea for a great fantasy novel. And then there's the middle of the story you have to write, has to be interesting…

But as I say, in all cases at least I'm not stuck in Walter Mitty's [1] shoes for the rest of my life.

[1] https://en.wikipedia.org/wiki/Walter_Mitty

> It's much more comfortable to be the person that "could be X" than to be the person that tries to actually do it.

It’s much more impressive to say you have done something than to say you’re going to do it.

A friend of mine has all these failed hobbies he tells everyone he’s going to do, then gives up on. I wait a few months before telling people I’m doing something so I’m fairly confident it’s something I will carry on.

I agree, and I'll supplement with this;

>> But from now on, I'm either gonna be a successful founder, or I'm not. And if I'm not, I'll have to deal with having broken with the expectations that people had of me.

Don't worry, they expected you to fail. They hoped you'd succeed, but expected failure. Statistically most businesses fail, and failure rates are faster when your customers are VCs not users.

I say this as encouragement, not criticism. Accepting that failure is (by far) the most likely outcome is both realistic and freeing. The anxiety of failure is gone.

Frankly, your lack of marketing experience would worry me. Without the ability to reach users (much less customers) how can you do anything but fail? New businesses are not bounded by technical ability (especially in the age of AI) they are bounded by Marketing.

This kind of warrior ethos outside of fantasy books or games is a huge turn off to me, it feels so anachronistic. I don’t understand why it seems so prevalent in the US, especially as a country built on Christianity that has Jesus coming as an harmless lamb to teach compassion, humility and love. Courage, devotion, perseverance, sure. Victory or defeat? No thanks.

This!

That exact line in the OP's article reminded me of that exact quote from T.R. and it's great to see another mind had exactly the same thought to post it.

Yeah but the US presidents would say that - they typically have track records of wanton destruction that are rather easy to criticise. It is notable that Roosevelt was part of a generation of global political leadership that bungled their way into first an economic then a literal bloodbath, the magnitude of which the world has not seen before or since. And US policies had a major hand in setting up 50 years of communist ascendance across a big chunk of the globe. I think he might have nuked two cities on the way through too, don't recall if it was him [EDIT].

If those were events I was involved with, I too would be giving powerful speeches about the importance of disregarding critics. The decision makers only handled the situation well if you assume that the catastrophe of the early part of the century was a bit like weather, sort of coming form nowhere in a way no-one could foresee or really influence.

[EDIT] I checked, he set the program up but it was his successor that actually dropped the bombs. If Truman had any sense he'd also be talking about the importance of disregarding critics.

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.

Can you separate "who you are" from that worry? Seems to me it's a part of you and you wouldn't be you without it, for better and worse.

A wonderful and personally relevant thing to read.

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.

[1] https://pmc.ncbi.nlm.nih.gov/articles/PMC4441622/

[2] https://pubmed.ncbi.nlm.nih.gov/17717011/

And similarly:

  slow growth is terrible

Rapid growth feels like you're constantly plugging holes in the dike or putting out fires.

Like you I've had brief moments of jealously seeing a company that started after mine and grew faster. But when I think rationally, I just wish them well, and realize I'm happy with any pace of growth that's not negative.

they're also all mostly lying/fudging the numbers. you can't believe what you see online anymore

It's less about praising your children, vs being honest with them! Don't give them false praise, and they'll be fine.

Genuine praise on the attempt, rather than the result.

Even if it's a failure but a lot of effort and learning along the way, it is still a success.

> It kind of looks like this is happening to the author. He became a founder, and started doing things that seem like what a founder would do, then got hit hard when he was unable to fulfill the "founder" role (i.e. didn't grow fast enough).

This happens a lot in the startup world: It’s really common for someone to be among the top in their classes from a young age, be praised by all their family members and friends, and be called the next Bill Gated / Jeff Bezos / Elon Musk (adjust for age) for the first quarter of their life.

So they enter the startup world believing that they were destined for this. They may think success is inevitable, they just need to get that first investment round to hire a couple engineers and then start telling everyone what to do.

I don’t think this author is an extreme example of this because they’re actually talented and successful at many things. However I could see this mindset leading them down a path that seemed like the right thing to do but wasn’t actually a good fit for their personal style. The article talks about how they’re doing better now, but it’s filled with so many admissions that they think a full-time job would have been a better path in general that it’s hard to unsee it. I wish them the best and I appreciate the honesty, but I feel like I’ve seen this movie many times before in the local startup world.

What did they say they disliked about your work?

If you can bootstrap, bootstrap. That's my advice.

You might be able to move faster with VC money, depends on your product. But getting that VC money can break you. And now you're on the hook and you've lost full control.

It's a hard call to name root causes.

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.

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’ve made my career in startups (early employee of a success startup, founder of a failed startup, and now CTO of an early stage startup). Seems like the “cost” of starting something new is basically zero these days. You can “start” 5 different companies in an afternoon. The big differentiator is audience - if no one knows who you are, it’s so much harder to reach potential customers. I’d focus on building an audience first (LinkedIn/twitter), which will make things so much easier for you. You also don’t really need cofounders, it’s much faster building alone when you’re starting from zero.

> "- 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"

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?

Its not. If you have a resume, send it out. A startup is a business and if it doesnt make money, fuck it and do something else. Sometimes you have to throw the baby out with the bathwater before that baby destroys you.

I studied poker a lot in high school, and it still influences how I think today.

Probabilistic thinking about the EV of your decisions is a good framework, but "Just keep making good decisions" is the hard part. Same as in poker, though, the hard part about making a decision in life isn't the middle-school level probability math, but about making the right estimates about payoff potential and success rate based on incomplete information.

Analyzing things as they are rather than how you wish they were, being able to separate useful information from noise, and taking a step back to look at second-order effects are all useful skills that will help you make better decisions the more you develop them.

One of my favorite star trek scenes: https://www.youtube.com/watch?v=t4A-Ml8YHyM

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.

Life's odds are rigged.

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.

> 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.

It gets messy when the other poker players are your mentors and family whom you love and respect, when the money is real, when the amounts to you feel enormous (whether they matter to the investor is a different story), and when losing carries unpredictable emotional and social consequences. And when mentors and family do it you are probably their only bet. It feels like betting other people's money and I totally get how that's a psychological hangup to feel that it is wrong.

I am not being sarcastic or flippant in this, it limits me to not be willing to take advantage of the risk/reward system, but it's somehow deeply tied into my ethics in ways I didn't even really notice until my second startup. And I'm okay with that limitation, but I'll work through it sooner or later and regain my appetite for risk.

Aside from that, many people despise thinking this way about their work. Like me, even though I'm willing to do it. I've met founders who loved negotiation. Like I swear they must have been nightmare children. I hate negotiation, I want people to treat each other fairly and will stick with a good human that does so forever. I suspect those people don't mind ripping off family and friends, much less strangers. It is harsh, and I've seen things, but anecdotes aren't statistics, and that's a huge obvious red flag to me. If the leaders like to do internal negotiation games I just want out. It's just painful to have to deal with being around when you just want to make stuff work.

It's important to talk about ahead of time, and get in writing, but that's also something easily overlooked among family and friends who do not do this kind of thing much. And the downsides need to be honest and clear to avoid mistrust.

Now, after working at two startups and starting three, my third is a consulting company that exclusively does things hourly except in very special circumstances. It's never going to grow fast because it scales as my hours of labor. But I am way more able to pick a price for my labor than decide how to price something that I haven't done yet. I could figure it out, I just kinda don't want to. For now?

See also The Book of Risk by Dan Borge.

> We raised a decent amount of money from YC and other VCs, and despite that, the thing that helped us most for distribution

When one does not raise money you get questions like "how do we know you will be here in 6 months, how are you funded?". I doubt people will tell you directly "oh, we have seen you are funded we decided to give you a chance".

> raising money is sign that your business is not doing well

You can raise money to execute (a part of) a larger plans. There are various fields that have barriers to entry in terms of regulation and/or compliance. This can still be couple of FTE + costs before you can sign any deal.

> work on your startup as side project until it's already generating 1.5-2x your annual salary, in a stable way

This highly depends on the type of business. If you are for example in B2B you can't tell your customer "sorry I can meet only after 19:00 because of my other job" not to mention how you can be perceived.

I would add to reasons why you should raise money: make sure the startup has external feedback that you listen to. All founders are quite stubborn - which is good and necessary - and is hard to convince them they need to adjust/pivot/rethink things. Investors can do that, but best is to have some previous experience with the field, otherwise they can be just noise.

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!

The best business plans:

1. do not require secrecy

2. do not require external funding to enter a profit mode

3. do not quire some fancy specialized team labor skills

4. do not operate like they have a $10B market cap with financial and legal teams

5. produce products that are unique, have actual utility, and have perceived scarcity in the market

One often will keep more money with a smaller firm in a niche, than competing with irrational groups with practically unlimited hype investment capital. Most truly successful people I know do not hang out on social media goading competitors and cons. =3

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.

if i bet on someone and they wrote this id know my money was spent well

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.

Hey, author here. I was working part-time for months, we had a live product with customers, a thesis, and an execution plan. This part was maybe lost in the post.

We raised, continued down the same path, and only then realized it didn't make sense. I was being honest about my motivations in hindsight here, realizing after the fact that the product we had at the time wasn't the idea of my life and that I really wanted to go out on my own (and took the chance that appeared).

I dont want to dump on the founder here. I appreciate their guts for saying the uncomfy part out loud and being so honest, open and aware of their own thoughts. Major kudos in my book. But dont quit without a quit criteria - a problem, customer conversations, recurring problem insight. Fuck the VCs that say just do it, its advice for rich kids not people who worry about finances running out. Given that this author worked at Posthog, it probably means they lived in London and got paid a decent salary but not a good one. eg Posthog lists their comp at 120k pounds with equity (that thing doesnt have liquidity yet). Thats not a top of the line offer in London where Meta / Goog and others would beat it. Once you have say 100k pounds saved up and mortgage for the next 2 years, maybe then you can think of bootstrapping without an insight. Until then, Leetcode, promotions, better offers are your ticket out of a middle class life. VCs wont show up with more money if and when you're hungry.

Starting with the desire to be a founder then searching for a problem is something I’ve only recently discovered is a common occurrence. And i find it a sort of odd reason to become a founder.

Has it this always been common or if it’s a characteristic of a vc-hype cycle?

Why devote yourself so long to creating solutions for a problem of solving it isn’t more gratifying than money?

But after almost decade of working in GTM for B2B startups, I’m starting to realize I find it totally unfulfilling and having begun moving back into the arts world i came from. So maybe I’m just cut from a different mold. Not better, just different.