Raising money fucked me up | Hacker News Reader

Raising money fucked me up

blog.yakkomajuri.com

391 pointsyakkomajuri142 comments

> 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.

Good luck, and go get 'em.

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.

Who needs marketing when the VC can get their entire portfolio to buy your product.

VCs are the best advertising.

Leaving aside for the moment yesterday advertising and marketing are very different functions (advertising is easy, marketing is hard);

If your target customers are "VC funded companies" then sure, getting in bed with as many VCs as possible is certainly one marketing approach (and probably a good one.)

Certainly you're are a lot of products targeted at businesses who are flush with cash and eager for kit like fancy chairs.

The important part of marketing is knowing who your potential customers are, and the best way for them to get to know you.

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.

Are you thinking of FDR? Theodore Roosevelt was long before nukes.

Oh yes, sorry. I was thinking FDR when I wrote the comment - but happily I can leave it unchanged since the same complaint applies to Theodore Roosevelt as well with only some minor tweaks. They weren't as bad as the Europeans, but the quality of the US leadership was not good given what they teed up in the early 20th century.

It is similar to the Bush family, but from an era where the internet wasn't around to let people compare notes. These political dynasties deserve criticism and should listen to it.

There's a lot of evidence to suggest FDR set up Truman, it's well documented he kept Truman in the dark until he died.

A) wrong Roosevelt

B) there's no way for the US to not get involved in WW2 other than pre emptive handover of the Philippines to Japan.

There is a lovely synthesis of A and B though - looking at the Wikipedia page for the right Roosevelt, he was involved in the Philippine–American War where they occupied the Philippines in the first place (or pacified, if you prefer, I suppose they'd probably already occupied the place in advance of the war). So if you're complaining about the Japanese conquering the Philippines you'd have to agree that Teddy Roosevelt deserved some criticism for also doing exactly that?

The criticism basically writes itself. These people are very easy to criticise, they were mostly horrible. Just saying, it is easy to see why there are speeches around about how the critics ought be discounted. The track record invites harsh criticism.

The thing with critics is that anyone can be one, it's easy, especially with hindsight.

What is difficult is being in the position of ultimate responsibility over the lives of many people, making a decision and living with it. Everyone thinks they know what is best or what they would do, I don't think so.

Criticism (IMO) should always have a response on what should have been done instead, given the information at the time. Otherwise it's just playing Monday morning quarterback.

Is supporting Philippine control of the Philippines a hard position to argue to? It is really easy to propose better strategies than almost anyone was going with in the early-mid 20th century, it is hard to overstate how badly the leadership of that era got it wrong. The US system did an amazing job of outperforming the Europeans and Asians, but it wasn't because the quality of its people was higher. The US presidents didn't suddenly become incompetent with Trump and Biden - they've consistently been not up to the task and it is just the visibility in the modern era is a lot better.

The only reason the US managed to look good coming out of the 1900s is because they were doing a much better job of limiting the government than the Europeans or Asians. Both of whom had significant authoritarian factions that managed to get embedded in the official power structures and refused to see sense for an embarrassing number of decades. Very much critics-don't-count people, the authoritarians. It is amazing looking back at the trials Europe had to go through to see out the monarchies.

"It is not the critic who counts..." was a great speech and there is a kernel of truth there, but it just so happens that there is a reason it is a US president who gave it. The reason the US does so well is it makes it as hard as possible for the president to do anything because the critics are shooting fish in a barrel when they start making legitimate, accurate and important criticisms of US president that certainly do count. It is a dream of the US presidents that the critics would stop reminding everyone that there are better options that said president should be choosing.

> 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.

> A friend of mine has all these failed hobbies he tells everyone he’s going to do

IME over years, when you're talking about doing something your actually doing it is thwarted. I've noticed that that both with myself and with others.

Keeping mum and going about it privately, then sharing it when done, seems to have much higher success rates.

I've tried to reason through it in many different ways: talking about it satisfies you and you don't seek satisfaction from the actual implementation of the idea; talking about it "dissipates the energy"; and a number of other attempts at explanation.

But beyond explanations, the anecdata seems to suggest that doing much precede talking about. Even when you're developing something (say, software) in public, first you do then you talk about it in the commit message.

This seems to parallel the old dictum that ideas are easy, while working to realize them is the actually hard part. Who'd have thought.

I agree wholeheartedly. It's like the energy and motivation has to go somewhere, and talking too much is a vacuum.

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

From my experience, you have to do both otherwise someone else takes what you do, markets as his own and you get scraps. It keeps happening to me, since I don't generally like to talk about what I do. And I think fundamentally it's a big difference between European and American culture.

Might be more of a difference between what to do in your working (employee) life vs in your private life. In your private life, you can't get scraps because it's generally work on things you own, like a business, personal fitness, skills, etc. In your employee life, you're generally working on things that you don't own for recognition to get a promotion or raise. There the recognition is the entire point and people may not look too deeply into who did what, so you may need to be more overt about things.

I wrote a (shortish) book with someone once who was obviously much more attracted to the idea of being an author than actually writing a book.

I've worked for a few bosses/ceos like this. Far more interested in being seen as someone with a particular title or company and far less interested in what it takes to actually make that worth something.

I notice that if you get to the point you could be doing something any extra thought is probably counter productive but to talk about it might even end it.

The entrepreneurial spirit isn't visiting you to talk about things.

Many people like the idea of X much more than the reality of X.

>more impressive to say you have done something than to say you’re going to do it.

Even more impressive to do and not say.

>It's much more comfortable

It can be even more amazing what can be accomplished during a time when comfort is not being sought.

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.

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.

Your complaint is well warranted, yet know as one on the other inside, Americans are apathetic and dejected. It is the mob that professes these self delusions as their own. And Americans are not self aware enough to distinguish the mob heads from their own and in the heat of exchange.

The individual American goes along with the strongest voice in their head. There have been a valiant few, this is a time of self satisfying rhetoric. Sweet lies over bitter truths, on all sides.

Now, the seeds of hypocrisy long since sewn, blossom into a mass mind sickness of self identity we see today. On all sides. Every side, even those twelve sides deep you would not recognize.

Power is everyone’s burden, it may only be delegated irresponsibly for so long before it collapses upon itself.

You're missing the part in Christianity where he comes again, this time as triumphant victor who overcame all things to save the human family.

> This kind of warrior ethos [..] feels so anachronistic.

A succinct condemnation of our times.

Also a succinct condemnation of HN as a hub for strivers.

i used to shun this kind of rhetoric when i was younger, preferring to think of myself a scholar among the Simon the chipmunks of the world, but I've come to accept that humans are made to fight. i dont think its wrong to venerate the warrior - im the farthest thing from a US citizen or a Christian, but my culture still has their folk heroes. look up lieutenant adnan if you'd like a stirring of the spirit

Yeah, I’m in agreement here. I get how this mindset might be off-putting, but we’re still in a phase of human development where if you don’t fight, you’re going to lose to people who will.

Trump is an example of someone who wants to fight, and now all of us who just want to get along are now playing catch-up, trying to figure out how to respond.

Sure those are the things Jesus advocated for in society, but it's not as if a warrior ethos isn't warranted for Jesus considering the attitude towards his message at the time. Especially when you gauge it in the light of what eventually happened to him. The ultimate message in Christianity is the necessity of perseverance in pursuit of goals. The world in general isn't immediately receptive to a message that priorities acceptance over lament.

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 is always the "what if" when looking back at the opportunities that presented themselves in life that eat at you. Things that might have been were it not for the lack of courage to try.

I rarely regret the things I did that didn't work out, it is always the things I could have done but didn't do. Reducing the number of compelling yet unexplored branches in life significantly increases life satisfaction.

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.

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.

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.

Reminds me of Internal Family Systems (IFS)

That’s more about the idea that it’s helpful to think of ourselves as made of parts, as a way to describe both our various roles in life (employee, spouse, friend, learner, etc) and also how we can interact with parts that we’ve exiled away, or hold experiences we have hangups about.

What I’m mostly talking about is that transformation happens through life’s journeys! Requires much less commitment to the idea, as it’s pretty universally understood.

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.

Imo, the opposite is true: you'll find out who you are only when you have given up all those false identities animated by you.

The closest show/cartoon for this I can think of is Rick and Morty Season 7, Episode 10 - "Fear No Mort." In that episode, Morty gets trapped in a fear-based "hole" where he's forced to confront all his deepest anxieties and insecurities. The whole point is that he can't escape by running away or pretending to be someone he's not. He has to face his fears directly and accept his true self, flaws and all. It's only when he does and accepts himself as he actually is, that he's able to break free.

That episode really got to me. Every time the screen goes dark and transitions to Morty realizing he's still trapped in the hole, something inside me freaks out too. It's like the show is forcing me to realize I'm not actually confronting these truths in my own life. I'm probably still in the hole, aren't I?

For me the question is just, do you think it's a disorder or not. Would you take a medication for it, if there is such a thing. If yes to both, Then, it's not really you. You are just who you choose to be.

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/

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.

> forcing myself to do stuff I don't want to do every day

If you make it over the initial hump of developing the habit it just becomes an expected part of your day. The dislike evaporates. Skipping it feels weird.

Maybe I'm just a baby, but I actually have done routine exercise for long periods (sometimes months, sometimes years) and stopping felt AWESOME.

Fair enough. That is most definitely not normal but I believe you that it's just how it is for you. It's the same thing with any given medication - it will work for most people most of the time but not for everyone all of the time.

The trick is to tie your sense of identity to being a badass with more than enough self control.

Most people are complete dumbasses at 25. (I include myself at 25 in that assessment) So if this is peak intellectual capabilities something does not add up.

It's the lack of experience, essentially. See this chart from the study I linked: https://i.imgur.com/zhR6NC1.jpeg

Things that rely on experience peak at a much higher age, but the pure mental stuff peaks earlier.

To me that graph seems to say that the pure "subconscious" stuff or "ML similar" stuff peaks earlier, but comprehension peaks much later. So you perfect your tools in the brain at around 25, but then it takes another 20 years to really know how to use them correclty.

That’s one way to think about it. For me personally, a single evening with even driven and dedicated 25 year olds makes any claims of a downward slope like you describe laughable. At best, they’ll know one thing sort of well at that age. Most of the interesting stuff happens when you synthesize a lot more experience, and have the appreciation for time and wisdom to utilize it well. Whats the average age of startup founders, like 45? Average age of authors first books like 36-42.

Give me a break with that hustle culture.

Your last paragraph brings to mind an insult from a fictional culture where the very wealthy and powerful can live indefinitely: "<minor villain> has grown nothing. And he has planted nothing". Such a perfect summation of the attitude of a culture with lots of time

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.

> 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.

I felt this post and appreciate the honesty.

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

And similarly:

  slow growth is terrible

Slow growth is awesome! Slow growth gives you time to address the challenges of growth, and think through sensible solutions.

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.

>low growth is awesome! Slow growth gives you time to address the challenges of growth, and think through sensible solution

Well, this is somehow incompatible with VC-MBA-bobo architecture?

This may sound weird but this was a very interesting read for me as a father of 2 small kids.

A somewhat common (yet often not followed (because it's hard)) piece of parenting advice is to not praise kids too much. Especially character judgements like "you're so smart" or "you're so creative". Reason being it makes them do things that seem smart or seem creative just to get the praise. Then it comes crashing down when they're faced with a challenge that contests the idea that they're "a smart kid".

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).

I'm not totally sure what to conclude here. I guess humans are susceptible to this kind of thing regardless of age.

> 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.

> 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.

My personal experiences taught me that things generally do no play out as one imagines neither for "startup" nor for "full-time job". There are advantages and disadvantages for each, best is to try (a bit) both and decide for yourself. Of course I get that for some this is not possible, just saying what I think it would be the ideal.

I think some discontent with one's current situation is healthy - to allow for progress - but I always find strange when people strongly project that "something else would be better" without having experience with it.

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

I believe the what the parent comment was referring to is the advice not to praise character, but instead praise hard work.

“You’re so smart” leaves room for failure when they encounter something that challenges their image of being smart. Praising the amount of effort they put in is not something that is taken away or challenged regardless of the outcome.

One of my kids are particularly brilliant and what I found is that the combination works best, "you are smart therefore I have high expectations" AND "without doing the work being smart doesn't matter". Together this creates a self image of the capable doer.

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.

> As I dug deeper into these feelings, I realized I was feeling pressured. Except they're not saying this, I am.

That's a great insight.

Once you've realized that, I think the best thing to do is to talk to the person whose pressure you imagine. Then you can find out what they're really thinking. Perhaps they really are thinking that (in which case the pressure is real and you can act on it) or they aren't (hearing them say that will alleviate the pressure).

Once when freelancing I asked a customer what they liked and disliked about my work. They had previously seemed happy with me, so I was pretty sure I know what they'd say. I believed I wrote good stable software. What they actually said was they were a small company, and they had had previous developers who, when there were server problems etc., just shrugged and said they didn't know how to fix it. They felt I wasn't like that, that I'd sit there and get it fixed, call up friends if necessary, etc. So yeah, they were happy, but not for the reason I'd imagined.

So my learning was: So you always have to talk to people to find out what they think. You really can't guess.

What did they say they disliked about your work?

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 think time and again, the main thing people should realize is you should never, ever raise venture capital unless you really, really have to™.

Or at least know that your interests as a founder and the interests of those who invest in your company will not always coincide. And they do this a lot more times every single day than you do.

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

I build entertainment experiences (escape rooms, live game shows, etc.), and I find that this also applies to individual projects/products. In the early planning stages we outline the ideal contours of a project, but as we build and run into constraints we start to see the gap between our vision and execution. And, usually, it's fine. We're the only ones who can see that gap because we're the only ones who knew the original plan. Guests only see what exists. We see what almost existed, what was left on the cutting room floor.

The planning stage is the most comfortable because we don't yet have to reckon with how we have fallen short of our plan. Now, during every planning phase, there's a visceral acknowledgment that there will be a gap between vision and execution, but we make choices that attempt to make those gaps smaller or, at least, acceptable.

I used to have problems like this and then I almost died a couple of times. I no longer have problems like this.

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.

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.

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

I totally agree with that statement and it mostly explains why so many people does not go down a rabbit hole.

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’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.

Loved it, understanding and working through your vulnerabilities is super hard but ultra rewarding. Bold but very altruistic move to publish this

Some feedback from me (not a likely user though):

- 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!)

> "- 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?

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.

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.

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

> 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.

In poker you learn to strategically size $X based on your estimates of $Y, Z%, and current bankroll.

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 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.

I think the metaphor is pretty extensible to handle the things you point out.

> 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.

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.

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

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.

Nice.

What are some good books to build this sort of perspective on Probability/Randomness/Chance?

These are ~1 layer removed, but it shook me from an epistemological perspective. Basically it destroys the idea of metaphysical truth.

I'll start with the easy one that was written in native English, William James's Pragmatism. Its only 4 hours long, and teaches 1 of the 3 branches of metaphilosophy(Pragmatic). For ROI in philosophy, it doesn't get better than this. It teaches one of the 3 theories of Truth.

Next is significantly more difficult, but everyone only understands 10% of Wittgenstein. Read both early and late Wittgenstein. If I remember correctly, its ~12 hours of pain as you will barely understand him. However, it shakes foundations of math and science as you will find these are mere constructs of language. This will also teach you 1 of the 3 branches of metaphilosophy(Analytical), and teach you how language works. You really need to read both early and late. But I imagine reading early Wittgenstein will convince you to read late. Its super painful, but you should deal with the pain.

(the remaining branch of philosophy is Continental... that takes a long time to learn, but its mostly nonsensical rebuttals to Plato, take it from someone who read this for 8 years...)

Regarding that initial thought on the Problem of Priors, here is a quick youtube video: https://www.youtube.com/watch?v=xy6xXEhbGa0

William James i have read, both "Pragmatism"(not completely though) and "Talks to Teachers" (my favourite) but not much of Wittgenstein.

There is a lot here which jives with ancient Hindu Schools of Philosophy, specifically; Nyaya (https://en.wikipedia.org/wiki/Nyaya), Vaisheshika (https://en.wikipedia.org/wiki/Vaisheshika) and Charvaka (https://en.wikipedia.org/wiki/Charvaka).

Bayesian epistemology with priors have always been problematic since if there were no constraints on prior beliefs than anything goes. But in order to constrain the priors you need to know the distribution to calculate probabilities.

If I can recommend anything: Stay away from ancients. Western or Eastern.

Stick to contemporary people who are dead and have no marketing team to promote them.

> Stay away from ancients. Western or Eastern

This i very much disagree with. Your username already hinted at your pov ;-)

As Nassim Taleb (a good marketer of himself!) points out in his works; the ancient philosophers (western or eastern) had gotten a lot (all?) about Life right.

Read Wittgenstein and maybe finish pragmatism.

There is a reason not even Continentals use ancient thoughts anymore.

But at least read Wittgenstein.

If you want a complete destruction of ancients and pre 1800s thought, Rorty has Philosophy and the Mirror of Nature. Its incredibly boring and teaches you nothing except that these ancients having incorrect understanding of language, psychology, and metaphysics, caused them to make grave mistakes.

> these ancients having incorrect understanding of language, psychology, and metaphysics, caused them to make grave mistakes

That is absolutely and staggeringly wrong.

It maybe the case with some of the ancient Western Philosophies (objective, analytical), but certainly not the case with Eastern Philosophies (subjective, experiential). "Human Condition" has not changed but only the context in which it is experienced and expressed has changed.

Read at least the three schools of Indian Philosophy i mentioned above. S.N.Dasgupta's multi-volume A History of Indian Philosophy gives a very good non-trivial starting point for the serious reader.

See also The Book of Risk by Dan Borge.

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.

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?

This hit close to home..!

I had a startup some years ago and took angel funding from family. When we were later running out of cash and had to raise professional money to stay alive, the pressure of the expectations I thought my family had because I was on the verge of losing their money caused me debilitating panic attacks.

I still feel the effects 6 years later, but have learned to cope whenever I feel the pressure begin to build. But man did it scar.

OP if there is any advice I can give, it's that you should have a chat with your investor friends about and make sure you feel like you can always walk away.

That sort of jump always looks both incredibly brave and foolish to me. I guess it’s necessary for startups though.

I’d think more would do a ramen bootstrap to test waters on both product fit and potential for monetization though

Im a former YC founder, I recommend to NOT raise external money from anyone, unless there is literally no other choice.

Raising money has been marketed as success by VCs and they have done a great job of it. Remember, that in reality, raising money is sign that your business is not doing well.. not the other way around.

Furthermore, a lot of people hope that raising money will help them get distribution and customers' trust. Thats NOT true. We raised a decent amount of money from YC and other VCs, and despite that, the thing that helped us most for distribution was content SEO and posting on reddit + no customer ever told us that they were using our product cause we raised $X from these VCs..

People also expect that well known VCs will help you magically solve issues in your company. That's not true either.. VCs may seem very smart, but when it comes to the details of solving issues about your company, they literally can't help, cause they don't know as much as you do about your business.

Another reason people want to raise money is cause they can't afford to quit their jobs and rely on their startups. In this case, well, do not quit your job.. work on your startup as side project until it's already generating 1.5-2x your annual salary, in a stable way. Remember this way, you dont have a deadline for your startup based on your runway, which is GREAT not only from your startup's survival point of view, but also from a mental health point of view.

I would also like to talk about hiring. A lot of people just assume that raising money is needed cause that way they can hire people and grow faster. This is again, not true.. usually, hiring people means you are actually going to slow things down unless you know EXACTLY what you want to hire for, which is rare for a startup. Even if you find a great person for the job, they will take at least a few months to be full productive, and if your startup is not growing like crazy (which is true for most startups), the person will likely leave (cause they are good and will find a better company) = wasted time.

I would like to say that money you raise for your company is NOT your personal money. You can't just spend it on buying stuff for yourself. In fact, even taking a decent salary from that money is looked down upon, unless your startup is doing really well already.

Finally, VCs play a numbers game. They invest in 100s of companies hoping one of them will give out a massive return and cover the losses for everyone else + make a huge profit. You are, statistically, in the ones that won't make it, and you will be written off.. at this point, you will have an entity, owing a large part of your company who literally doesn't care about you.

All of the being said, here are the reasons of why you SHOULD raise money: - Your business model only works at scale. - Your initial investment costs are very high: This is usually never true for software companies. - You are trying to impress your partner and / or friends in the short term and give them the illusion that you are successful already (lol).

> 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.

> 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".

The thing is, we did raise money, and we still go the same questions, and we replied saying these are the VCs that have funded us, and we still lost those kinds of deals. The deals we won, were mainly cause we solved some burning pain point of that specific user, who really didn't care about our funding status.

> 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.

Agreed. But for most startups, people raise cause they need more money to survive.

> 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.

Agreed. It's not ideal, however if you are solving a big enough pain point for the user, I'm willing to bet they won't mind it.

> 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.

Yup, I agree here as well. But, the best external feedback is not from your investors, but from your (potential) customers!!

> 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.

Finding the right psychologist/coach/founder to chat this over with will probably do you and the company wonders.

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!

Awesome to hear. Best of luck!

I think this is why I unconciously hold back from ever asking money for any of the stuff I build. Much more comfortable.

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.

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

The author felt pressure to build an explosive startup with tons of early funding. For those feeling similar pressure, look into the concept of “slow burn startups.” These are startups that stick around and make long-term impact.

If you can innovate do it and you’ll be profitable. If you can’t then hope you have good relationships and can peddle marketing nonsense with a smile. These VC guys are shoebutton Edisons looking for Teslas.

what a great article. I've started a daily blog this year a la nik.art, but its really easy to write about surface level stuff like what my projects are or how i enjoyed a piece of media. today, i skipped the blog post, telling myself it was just a rest day because sundays, but in reality i just went through some upsetting shit and didnt really want to write what was on my mind. this post really made me realize that's kind of the point of writing though. thanks for sharing :)

There is a space between man’s imagination and man’s attainment that may only be traversed by his longing.

-- Kahlil Gibran

Yeah, startupping is a hard path to take. If you have a nice job - stick to it and live below your means.

I really liked this, thank you

thanks for sharing your thoughts. I'm about to go down this journey and this is extremely useful to keep in mind.

That was such a good read. Thank you!

you might be early to market with something like Skald

Never regretted not striking out on my own, but I suspect people who have the cojones to try, would utterly hate not having tried.

It's not symmetric.

Dude: we’re provably (not probably) in a recession.

It’s just really, really hard to get someone to pay you money. This AI boom has made earning money optional for some companies, but for the long tail of AI-adjacent companies you need revenue. Convincing someone to pay you is just simply so so hard. No one really gets it until they have to actually make revenue. It’s sooooo hardddd

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.

You lost me at girlfriend, pal. But seriously, it's the living dichotomy between master and slave morality. There is a different system to live by when you're in the higher echelons of performance.

Imagine betting on someone and xe writes this ...

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.

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

Good. Send xir some cash!

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.

This is absurd! The author raised money without a concrete execution plan, treating capital as permission to “think,” and then panicked when thinking alone didn’t magically turn into value. The post implies there was no wedge, no market insight, not even a search strategy... just the weird hypothesis that people say 'I fit the founder profile, therefore I should found something' It frames the absence of structure as a psychological tragedy, but irl this was a self-inflicted governance failure. The author clearly had no personal theory of value creation before taking investor money, and the money simply magnified that undefinedness. Paying yourself to think is ridiculous unless you’re running a consultancy otherwise it’s just accountability theater... Cinema being what this post is!

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.

What's wrong to stay in the middle class? Furthermore in the UK - you cannot "promote" yourself to upper class, have to be born in it.

I mean it was more about wanting to better your financial condition. Thats what I meant. By upper class I meant financially not like aristocracy.

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.

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).

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