> 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.

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.

> 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.

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.

> 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.

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.

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.

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.

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!)

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

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

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

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

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.

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).

> 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.

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 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 :)

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

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

-- Kahlil Gibran

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.

[dead]

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 ...

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!