Raising money fucked me up

(blog.yakkomajuri.com)

200 points | by yakkomajuri 11 hours ago

23 comments

  • Esophagus4 5 hours ago
    > 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.

    • bruce511 2 hours ago
      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.

      • what 2 hours ago
        Who needs marketing when the VC can get their entire portfolio to buy your product.
  • taurath 8 hours ago
    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.

    • resonious 3 hours ago
      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.
    • teiferer 8 hours ago
      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.
      • taurath 7 hours ago
        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.

        • Obscurity4340 2 hours ago
          Reminds me of Internal Family Systems (IFS)
          • taurath 1 hour ago
            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.

      • vlan0 6 hours ago
        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.
      • akomtu 1 hour ago
        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.
        • csomar 44 minutes ago
          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?

    • arathis 8 hours ago
      A wonderful and personally relevant thing to read.
    • Nition 3 hours ago
      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/

      • cannonpr 3 hours ago
        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.
      • resonious 3 hours ago
        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.
        • fc417fc802 1 hour ago
          > 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.

      • taurath 1 hour ago
        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.

      • ekianjo 2 hours ago
        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.
  • qudat 6 hours ago
    > 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.

    • StellarScience 30 minutes ago
      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.

    • asdev 1 hour ago
      they're also all mostly lying/fudging the numbers. you can't believe what you see online anymore
  • resonious 3 hours ago
    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.

    • sibeliuss 2 hours ago
      It's less about praising your children, vs being honest with them! Don't give them false praise, and they'll be fine.
    • Aurornis 2 hours ago
      > 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.

  • mcny 2 hours ago
    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.

  • didip 7 hours ago
    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?

  • xiphias2 4 hours ago
    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!)

    • nickjantz 4 hours ago
      > "- 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?

      • xiphias2 4 hours ago
        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.

  • tptacek 8 hours ago
    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.
  • jackfranklyn 6 hours ago
    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.

    • qingcharles 2 hours ago
      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.

    • robocat 5 hours ago
      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.

    • himeexcelanta 6 hours ago
      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.
  • soorya3 4 hours ago
    > 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.

  • quantumgarbage 8 hours ago
    Loved it, understanding and working through your vulnerabilities is super hard but ultra rewarding. Bold but very altruistic move to publish this
  • AstroBen 8 hours ago
    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

    • ericdykstra 34 minutes ago
      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.

    • altmanaltman 8 hours ago
      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.

      • diab0lic 6 hours ago
        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.

        • altmanaltman 3 hours ago
          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.

    • mhogers 7 hours ago
      One of my favorite star trek scenes: https://www.youtube.com/watch?v=t4A-Ml8YHyM
    • PlatoIsADisease 6 hours ago
      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.

      • rramadass 2 hours ago
        Nice.

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

    • teiferer 8 hours ago
      > 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.

      • foltik 7 hours ago
        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.

    • rramadass 2 hours ago
      See also The Book of Risk by Dan Borge.
  • debo_ 4 hours ago
    I used to have problems like this and then I almost died a couple of times. I no longer have problems like this.
  • geooff_ 5 hours ago
    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.

    • Joel_Mckay 1 hour ago
      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

  • Aeolun 5 hours ago
    I think this is why I unconciously hold back from ever asking money for any of the stuff I build. Much more comfortable.
  • neumann 7 hours ago
    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.

  • PlatoIsADisease 6 hours ago
    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.

  • jbs789 8 hours ago
    Finding the right psychologist/coach/founder to chat this over with will probably do you and the company wonders.
    • yakkomajuri 8 hours ago
      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!

      • jbs789 8 hours ago
        Awesome to hear. Best of luck!
  • user3939382 49 minutes ago
    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.
  • danield9tqh 5 hours ago
    I really liked this, thank you
  • hahahahhaah 5 hours ago
    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.

  • rramadass 3 hours ago
    There is a space between man’s imagination and man’s attainment that may only be traversed by his longing.

    -- Kahlil Gibran

  • moralestapia 8 hours ago
    Imagine betting on someone and xe writes this ...
    • allenrb 7 hours ago
      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.

    • globalnode 8 hours ago
      if i bet on someone and they wrote this id know my money was spent well
    • teiferer 8 hours ago
      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.