What is the execution risk of Gumroad's open, decentralized model, with open-sourcing and lack of full-time employees?

Guest: I think that Gumroad has an extremely high amount of momentum and they have an extremely high amount of inertia, right? Because of that base of creators who have been using them for so long. For that reason, it's unlikely they'll ever not grow. Or at least it's unlikely that the company will ever see negative growth. I don't think the company will shrink.

I think we're in the very, very, very early stages of the creator economy. I think a company that's being treated as a side project will end up performing the way you would expect a side project to perform, or at least be limited in the way that you would expect a side project to be limited.

We hear a lot from former customers of Gumroad about the slow rate of change, the slow rate of development, the bugs, etc. So I think that the way that they run their company, for a very long time, will be a very successful lifestyle business for Sahil. I think it'll continue to be a very, very successful lifestyle business.

But, I think in 10 years, when you look at the ecosystem of creator economy companies, I find it hard to believe that if they continue running the business, in that way, it'll grow at the same pace as the economy.

The reality is when your head of product works, 10 hours a week or 20 hours a week, or when your head of development works no more than 20 hours a week, I think it's very challenging to build a company that keeps pace with the market's growth.

Now, with that said, I don't know, maybe the goal is not to keep pace with the market growth. And I think there many companies that operate in a slow cadence and print money.

I think Basecamp is kind of the classic example of this, of a company that prioritizes work-life balance and has built a pretty successful company that does very well, but they're certainly not one of the top three biggest project management tools out there.

It depends on the goal. And so if the goal is to win the ecosystem, I don't think Gumroad is acting in a way that puts on pace to do that. But if their goal is to build a very successful lifestyle business, I think certainly they have what it takes.

I think it'll be interesting to see if Gumroad can maintain that growth. I think if you look at comparable companies in the space, maybe a company like ConvertKit, which grew 150% in year two, and then 50% in year three and then 27% in year four. I think something like 30% in year five, I think 40 to 60% is going to be very difficult to maintain over 10 years. Teachable year two grew 110% and then 52% and then 44%. And they have a hundred plus full-time employees working on growing this company. I think 40 - 60% growth is very ambitious for 10 years. 

I think 2020 is a perfect year to price the creator economy company. If you're looking to raise money.