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Reflecting on My Failure to Build a Billion-Dollar Company

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Re: Reflecting on My Failure to Build a Billion-Dollar Company

#361
post #188

Earlier quoted context omitted.

Patreon and Gumroad were different businesses for most of their histories. Gumroad was always a place to sell stuff and launch subscription services. Patreon is trying to pivot that way now with all their talk of membership businesses, but no one who uses it seems to see it that way. That's why everyone was up in arms about the fee change in 2017. People tossing $1 here and there to people they liked were the foundat…

Any examples of other business that do what you mention at the end? Just curious what the "better" options are. I like to keep abreast of the underdogs.

Gumroad is the only one I've used. Others popped up over the years, but I didn't think to keep notes.

Re: Reflecting on My Failure to Build a Billion-Dollar Company

#363

Earlier quoted context omitted.

>at the end of that time there are two metrics, the number of people you helped and the amount of wealth you amassed and held on to, which number is a better representative of 'success'? But of course those are highly correlated - it's easier to help a lot of people if you have plenty of surplus wealth and time to share out. I'd imagine that Warren Buffet will end up helping more people that almost anyone else in the…

I couldn't possibly disagree more. For starters, I think the majority of those who accumulate massive wealth do so at the expense of countless others. Buffet is an excellent example, actually. As probably the premier monopolist of the late 20th and 21st centuries, he has played a huge role in consolidating industries and destroying US wage growth. That's probably the single most detrimental macro trend in terms of qu…

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Re: Reflecting on My Failure to Build a Billion-Dollar Company

#364
post #138

Earlier quoted context omitted.

so s/determine most/constrain/

Precisely this. Seems like a small change, but I think it's a significant one.

Fair enough. I think I'd make this change if I could go back in time!

Re: Reflecting on My Failure to Build a Billion-Dollar Company

#365

Earlier quoted context omitted.

I wonder if an entrepreneur with less connections and not a part of YC would get that $1 buyout deal. I would think the default would be ousting the founder and selling the assets. Then the founder would be left with nothing. They'd have no lifestyle business, even though they could have had one if they never took VC.

If he only did a series A, I doubt he gave up enough control to get ousted.

Looking back, I’m glad we didn’t hit those numbers. If we doubled down, raised more money, and appeared in the headlines again, there was a very real possibility it would only lead to a more spectacular failure.

Hmmm, reading between the lines, you seem to have a point...

Re: Reflecting on My Failure to Build a Billion-Dollar Company

#366
post #300

Earlier quoted context omitted.

1 basis point of $10b is $1m. It's pretty easy to see someone paying him well over that to buy GumRoad at some point.

I will guess that as employee #2, he had more than 1 basis point.

Yeah, I think employee #2 would be in the range of 50 - 300 basis points. (0.5% - 3%)

Re: Reflecting on My Failure to Build a Billion-Dollar Company

#368

My experience with Kongregate was different, but I did feel some of the same things. We became a vehicle for many indie game creators to make a living, which I'm very proud of. In our case we also had a sale that was very profitable for the founders and early employees, and also profitable for our investors. But the weird thing is that if our VC investors had known at the outset that they would have a 3x return on th…

> I’m an angel now You actually label yourself that vs. an investor?

I think it’s common usage that investor is implied? I invest in tech companies at the seed stage.

Re: Reflecting on My Failure to Build a Billion-Dollar Company

#369

My experience with Kongregate was different, but I did feel some of the same things. We became a vehicle for many indie game creators to make a living, which I'm very proud of. In our case we also had a sale that was very profitable for the founders and early employees, and also profitable for our investors. But the weird thing is that if our VC investors had known at the outset that they would have a 3x return on th…

> if our VC investors had known at the outset that they would have a 3x return on their money in three years, they probably wouldn't have made the investment. Of course they would have made an investment. Any guaranteed return above bank interest rate -- is appealing for investors. Guaranteed return of 50%/year is an amazing investment opportunity. What you probably meant is that if investors knew that the return can…

Look at it this way. A VC fund has a finite number of investments to make. Typically a partner gets to say yes once or twice a year. They usually take a board seat and spend lots of time helping the company.

Knowing that many of those investments will be worthless, they want to maximize the number of shots they get towards a billion dollar company.

If 1/3 of their companies are a 3x return, and the rest become worthless, the fund has failed. They’re all aiming for the one company that will deliver the big returns that offset all the failures (and the high fees they charge LPs.)

Seed stage investors are different. YC, for instance, spends much less time with each company, and therefore can take lots of shots.

Growth stage venture is different too. They aim to invest a few years before a company goes public, and are fine with a 3x-5x return. They are taking much less risk.

The VC model also creates a fundamental tension with the founder. Founders get one shot at a time. $50M exits represent life-changing money for them (as long as they didn’t raise too much money.) VCs pressure them to take greater risks than are rational for the founder. This is why you want to look for VCs that will truly put the founder first. Or keep control of your board.

Joel Spolsky explained this well 15 years ago, so we knew about it going in and chose a founder-first VC firm.

Here’s that post: https://www.joelonsoftware.com/2003/06/03/fixing-venture-cap...

Thoughtful VCs will do what’s right for the founder. It’s rational because their reputation matters so much when competing for investments. This has changed for the better since Joel’s post.

Re: Reflecting on My Failure to Build a Billion-Dollar Company

#370
post #189
post #66

Earlier quoted context omitted.

> at the end of that time there are two metrics, the number of people you helped and the amount of wealth you amassed and held on to, which number is a better representative of 'success'? Let's not forget personal satisfaction. I'm a little leery of putting the entire assessment of my life onto other people (even though if I was going to, I could do a lot worse than number of people helped). Hopefully helping other p…

Personal satisfaction doesn't matter once you're dead. Those other things do. And your entire assessment of your life at that point will be put onto other people. With that said, optimizing for after you're dead might be selfish and reasonably desirable, but there's a lot to be said for optimizing for tomorrow instead. Life would be pretty pointless if none of us were supposed to optimize for some enjoyment while we'…

“Nothing matters once you’re dead” seems inescapable until you realize that it’s based on the rather flimsy presupposition that presentism is true and eternalism is false.
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