[orthecreedence]

> Every dollar a startup can raise is a gift. For a time I lost sight of this, and I won’t make that mistake again.

This seems like too general of advice. If you are profitable without raising, that in itself is a gift. Why take on debt if you don't need to? This might apply to fast-growth ventures that need to outpace competition to have a chance at existing, but not every company is structured like this or is in a market that requires this.

> A regulatory rug pull can and will outstrip any early traction or compliance gold stars that you think might save you.

Interestingly, this reminds me of all the apps built off Facebook's APIs in the early days. They would regularly remove one feature that was catastrophic. It's difficult to base your existence on some whale's whims, but in some ways often inevtiable too.

> A critical third-party informed us that they’d changed their mind on a key technical decision.

I'm so curious who. I got sick of dealing with Plaid's ceaseless API changes and ended up writing my own scraper for Wells Fargo transactions. I doubt they were using Plaid though XD.

Overall a really interesting writeup and I'm thankful to the author for sharing.

[sillysaurusx]

That strategy works fine till hard times come. Look up Beyond The Summit sometime. Sad story how it ended.

Raising money insulates against death by starvation of funds. Of course, the game becomes different; you need to keep growing. But those are the two alternatives, and of the two, sustained growth over 8 years seems like a better general strategy.

[ssivark]

Just to balance out your comment — OTOH, a bootstrapped might survive tough times with some tough choices, but a VC-fueled rocket might sometimes have no choice but to liquidate if they can’t carry through with the growth necessary for the next round of fundraising.

[TeMPOraL]

Selling your soul to the Devil is great strategy for the Devil. It may be for you too, at least initially. But it isn't good for the rest of the world.

[dgreensp]

In addition, if I’m reading the article correctly, the reason why it would have been better to raise money when the projections looked amazing is that they didn’t pan out, and to expect them to be accurate was greedy?

I’ve been a founder, so I know that raising money is all about telling a story about the future, and the time to raise is when your graph supports that story, or before you have a graph. If a week later, everything is different, well, that’s start-ups for you. But I think it’s good to be able to take a step back from this and recognize how bizarre it is, and that a business doesn’t have to be structured this way.

[inmygarage]

Author here. Every week was better than the last, and I didn't expect all the bank/third-party stuff to get SO bad. It felt manageable in October 2021, but for most of H1 2022, the period of our best growth, it got a lot worse. The greedy part was waiting for a "perfect" time to raise. I think this may be obvious, but no such thing exists (as you probably know).