Raising money fucked me up

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.

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).

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

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

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

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

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

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

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

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

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

> 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.