6 ms·

Raising money fucked me up

391 points by yakkomajuri 9mo ago

moralestapia 9mo ago
Imagine betting on someone and xe writes this ...
- teiferer 9mo 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.
- globalnode 9mo ago
  if i bet on someone and they wrote this id know my money was spent well
  - moralestapia 9mo ago
    Good. Send xir some cash!
- allenrb 9mo 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.
jbs789 9mo ago
Finding the right psychologist/coach/founder to chat this over with will probably do you and the company wonders.
- yakkomajuri 9mo 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 9mo ago
    Awesome to hear. Best of luck!
quantumgarbage 9mo ago
Loved it, understanding and working through your vulnerabilities is super hard but ultra rewarding. Bold but very altruistic move to publish this
AstroBen 9mo 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
- teiferer 9mo 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 9mo 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.
- altmanaltman 9mo 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 9mo ago
taurath 9mo 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.
- teiferer 9mo 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 9mo 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 9mo ago
      Reminds me of Internal Family Systems (IFS)
      - taurath 9mo 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.
tptacek 9mo 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.
didip 9mo 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?
neumann 9mo 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.
- xenospn 9mo ago
  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.
PlatoIsADisease 9mo 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.
jackfranklyn 9mo ago
[flagged]
- himeexcelanta 9mo 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.
- robocat 9mo 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.
- qingcharles 9mo 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.
qudat 9mo 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.
- asdev 9mo ago
  they're also all mostly lying/fudging the numbers. you can't believe what you see online anymore
- StellarScience 9mo 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.
  - KellyCriterion 9mo ago
    >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?
Aeolun 9mo ago
I think this is why I unconciously hold back from ever asking money for any of the stuff I build. Much more comfortable.
danield9tqh 9mo ago
I really liked this, thank you
Esophagus4 9mo 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 9mo 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 9mo ago
    Who needs marketing when the VC can get their entire portfolio to buy your product.
    - ipaddr 9mo ago
      VCs are the best advertising.
hahahahhaah 9mo 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.
geooff_ 9mo 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 9mo 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
xiphias2 9mo 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 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 9mo 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 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 9mo 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.
debo_ 9mo ago
I used to have problems like this and then I almost died a couple of times. I no longer have problems like this.
soorya3 9mo 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.
rramadass 9mo ago
There is a space between man’s imagination and man’s attainment that may only be traversed by his longing. -- Kahlil Gibran
resonious 9mo 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.
- Aurornis 9mo 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.
  - vladms 9mo ago
    > 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.
mcny 9mo 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.
user3939382 9mo 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.
DANmode 9mo ago
Dude: we’re provably (not probably) in a recession.
monero-xmr 9mo ago
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
- another_twist 9mo ago
  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.
saint-evan 9mo ago
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!
- deleted 9mo ago
  [deleted]
- another_twist 9mo ago
  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.
  - MrJobbo 9mo ago
    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.
ggm 9mo ago
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.
adrianmsmith 9mo ago
> 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.
- tucnak 9mo ago
  What did they say they disliked about your work?
saxelsen 9mo ago
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.
rishabhpoddar 9mo ago
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).
QuiCasseRien 9mo 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 I totally agree with that statement and it mostly explains why so many people does not go down a rabbit hole.
Havoc 9mo ago
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
stephenlf 9mo ago
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.
olucas 9mo ago
That was such a good read. Thank you!
rrvsh 9mo ago
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 :)
alexissantos 9mo ago
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.
arikrahman 9mo ago
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.
sweetrabh 9mo ago
thanks for sharing your thoughts. I'm about to go down this journey and this is extremely useful to keep in mind.
timmy-tu 9mo ago
[dead]
MrJobbo 9mo ago
Yeah, startupping is a hard path to take. If you have a nice job - stick to it and live below your means.
thisisidiotic 9mo ago
you might be early to market with something like Skald

391 points by yakkomajuri 9mo ago

moralestapia 9mo ago

Imagine betting on someone and xe writes this ...

teiferer 9mo 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.
globalnode 9mo ago
if i bet on someone and they wrote this id know my money was spent well
- moralestapia 9mo ago
  Good. Send xir some cash!
allenrb 9mo 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.

jbs789 9mo ago

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

yakkomajuri 9mo 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 9mo ago
  Awesome to hear. Best of luck!

quantumgarbage 9mo ago

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

AstroBen 9mo 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

teiferer 9mo 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 9mo 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.
altmanaltman 9mo 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 9mo ago

taurath 9mo 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.

teiferer 9mo 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 9mo 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 9mo ago
    Reminds me of Internal Family Systems (IFS)
    - taurath 9mo 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.

tptacek 9mo 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.

didip 9mo 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?

neumann 9mo 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.

xenospn 9mo ago
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.

PlatoIsADisease 9mo 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.

jackfranklyn 9mo ago

[flagged]

himeexcelanta 9mo 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.
robocat 9mo 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.
qingcharles 9mo 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.

qudat 9mo 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.

asdev 9mo ago
they're also all mostly lying/fudging the numbers. you can't believe what you see online anymore
StellarScience 9mo 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.
- KellyCriterion 9mo ago
  >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?

Aeolun 9mo ago

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

danield9tqh 9mo ago

I really liked this, thank you

Esophagus4 9mo 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 9mo 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 9mo ago
  Who needs marketing when the VC can get their entire portfolio to buy your product.
  - ipaddr 9mo ago
    VCs are the best advertising.

hahahahhaah 9mo 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.

geooff_ 9mo 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 9mo 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

xiphias2 9mo 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 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 9mo 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 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 9mo 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.

debo_ 9mo ago

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

soorya3 9mo 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.

rramadass 9mo ago

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

resonious 9mo 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.

Aurornis 9mo 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.
- vladms 9mo ago
  > 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.

mcny 9mo 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.

user3939382 9mo 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.

DANmode 9mo ago

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

monero-xmr 9mo ago

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

another_twist 9mo ago
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.

saint-evan 9mo ago

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!

deleted 9mo ago
[deleted]
another_twist 9mo ago
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.
- MrJobbo 9mo ago
  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.

ggm 9mo ago

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.

adrianmsmith 9mo ago

> 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.

tucnak 9mo ago
What did they say they disliked about your work?

saxelsen 9mo ago

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.

rishabhpoddar 9mo ago

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).

QuiCasseRien 9mo 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 I totally agree with that statement and it mostly explains why so many people does not go down a rabbit hole.

Havoc 9mo ago

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

stephenlf 9mo ago

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.

olucas 9mo ago

That was such a good read. Thank you!

rrvsh 9mo ago

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 :)

alexissantos 9mo ago

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.

arikrahman 9mo ago

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.

sweetrabh 9mo ago

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

timmy-tu 9mo ago

[dead]

MrJobbo 9mo ago

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

thisisidiotic 9mo ago

you might be early to market with something like Skald