Rob Walling

Yeah, it's interesting, you know, in bootstrapping, let's say 10 years ago, gosh, when I did my talk, no, it must have been 20, I guess I did a talk 2017 or 18 at MicroConf where I said, I think bootstrappers are going to start raising funding. And I like hinted at it in like a five minutes section and one thing and kind of got some pushback. And then the next one, like half the talk was about it.

Yeah, it's interesting, you know, in bootstrapping, let's say 10 years ago, gosh, when I did my talk, no, it must have been 20, I guess I did a talk 2017 or 18 at MicroConf where I said, I think bootstrappers are going to start raising funding. And I like hinted at it in like a five minutes section and one thing and kind of got some pushback. And then the next one, like half the talk was about it.

And it was right as we were starting TinySeed. And some people were like, seriously pissed. They're like, what? Put in your book. Since you're doing that, you're saying people should do it. And I was like, no, people are already doing it. That's why we're starting Tiny Seed is because there's opportunity here.

And it was right as we were starting TinySeed. And some people were like, seriously pissed. They're like, what? Put in your book. Since you're doing that, you're saying people should do it. And I was like, no, people are already doing it. That's why we're starting Tiny Seed is because there's opportunity here.

Because I had already invested in, I don't know, eight, maybe eight or nine, about eight kind of bootstrapped SaaS, mostly bootstrapped SaaS that I just put my own cash into. And so the openness and frankly, the stigma of raising funding I won't say it's gone, because every once in a while I'll see an indie hacker post on Twitter about, this is why I don't raise funding, quoting some anomaly.

Because I had already invested in, I don't know, eight, maybe eight or nine, about eight kind of bootstrapped SaaS, mostly bootstrapped SaaS that I just put my own cash into. And so the openness and frankly, the stigma of raising funding I won't say it's gone, because every once in a while I'll see an indie hacker post on Twitter about, this is why I don't raise funding, quoting some anomaly.

Somebody sells for, what was it, was it FanDuel or something, sold for $500 million, and the founder got nothing. But it's like, yeah, there's more to a story than that. So there's always these exceptions.

Somebody sells for, what was it, was it FanDuel or something, sold for $500 million, and the founder got nothing. But it's like, yeah, there's more to a story than that. So there's always these exceptions.

And when we surveyed folks for the state of independent SaaS, it's somewhere around one in four, or almost one in three, like around 30% of bootstrap founders say they would at least consider raising funding.

And when we surveyed folks for the state of independent SaaS, it's somewhere around one in four, or almost one in three, like around 30% of bootstrap founders say they would at least consider raising funding.

Yeah, and it certainly makes it possible for less technical folks to do it as well because it's such a big cost, right? I was never, never anti-funding. And even in the days of Drip, considered like, man, it would be so much easier if I could raise $400,000 or $500,000. But I didn't know anybody. I didn't know how to do it. It was 2014, you know?

Yeah, and it certainly makes it possible for less technical folks to do it as well because it's such a big cost, right? I was never, never anti-funding. And even in the days of Drip, considered like, man, it would be so much easier if I could raise $400,000 or $500,000. But I didn't know anybody. I didn't know how to do it. It was 2014, you know?

It's like all the stuff that's available today wasn't out there. With all that said, with that preamble, let's talk a little bit about venture investing, what success looks like, and frankly, how many venture funds just missed the mark and don't even beat an index fund that I could buy a Vanguard index fund.

It's like all the stuff that's available today wasn't out there. With all that said, with that preamble, let's talk a little bit about venture investing, what success looks like, and frankly, how many venture funds just missed the mark and don't even beat an index fund that I could buy a Vanguard index fund.

Right.

Right.

So that means if I invested $100,000 into that fund, I got my initial $100,000 back and then an additional $210,000. No. No? You put $100,000 in and you got $216,000 back.

So that means if I invested $100,000 into that fund, I got my initial $100,000 back and then an additional $210,000. No. No? You put $100,000 in and you got $216,000 back.

And that makes sense to me. So I entertained, after I sold Drip, I had a little bit of cash on my hands and I entertained the idea of investing in a couple different venture funds. And I never did, but it wasn't because I didn't think the returns would be there. It was because I had enough people approaching me through MicroConf and this podcast where I was like, that's a legit business.

And that makes sense to me. So I entertained, after I sold Drip, I had a little bit of cash on my hands and I entertained the idea of investing in a couple different venture funds. And I never did, but it wasn't because I didn't think the returns would be there. It was because I had enough people approaching me through MicroConf and this podcast where I was like, that's a legit business.