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Rob Walling

๐Ÿ‘ค Speaker
3342 total appearances

Appearances Over Time

Podcast Appearances

Startups For the Rest of Us
Episode 748 | The Ins and Outs of Startup Investing

like Jordan Gall, right? With Cardhook at the time and Justin McGill with LeadFuse. And there were just these great little B2B businesses. I was like, I kind of had enough people coming my way at reasonable valuations, to be honest. No one, you know, when I went on AngelList, here was the problem. I went to AngelList because I was like, oh, I'm going to make a few bets.

Startups For the Rest of Us
Episode 748 | The Ins and Outs of Startup Investing

like Jordan Gall, right? With Cardhook at the time and Justin McGill with LeadFuse. And there were just these great little B2B businesses. I was like, I kind of had enough people coming my way at reasonable valuations, to be honest. No one, you know, when I went on AngelList, here was the problem. I went to AngelList because I was like, oh, I'm going to make a few bets.

Startups For the Rest of Us
Episode 748 | The Ins and Outs of Startup Investing

And holy mother of, I mean, the valuations for like almost no revenue were like 10 million. And I did put, I put like five grand into one of those and I put 10 grand into another. And all of them either went to zero or returned, one returned to me 11 grand. For my 10 grand investment, I was like, all right, I consider that.

Startups For the Rest of Us
Episode 748 | The Ins and Outs of Startup Investing

And holy mother of, I mean, the valuations for like almost no revenue were like 10 million. And I did put, I put like five grand into one of those and I put 10 grand into another. And all of them either went to zero or returned, one returned to me 11 grand. For my 10 grand investment, I was like, all right, I consider that.

Startups For the Rest of Us
Episode 748 | The Ins and Outs of Startup Investing

It really is. So I'm in a little bit of a unique position, right? I mean, that's the whole thing is like the deal flow is kind of coming to me.

Startups For the Rest of Us
Episode 748 | The Ins and Outs of Startup Investing

It really is. So I'm in a little bit of a unique position, right? I mean, that's the whole thing is like the deal flow is kind of coming to me.

Startups For the Rest of Us
Episode 748 | The Ins and Outs of Startup Investing

Absolutely. The minimum in my experience, and I believe every company I invested in was $25,000. And that was it. So, yeah. I mean, I'm sure friends, you can get a friend who can cut you a deal or whatever, but if you are trying to make that many investments.

Startups For the Rest of Us
Episode 748 | The Ins and Outs of Startup Investing

Absolutely. The minimum in my experience, and I believe every company I invested in was $25,000. And that was it. So, yeah. I mean, I'm sure friends, you can get a friend who can cut you a deal or whatever, but if you are trying to make that many investments.

Startups For the Rest of Us
Episode 748 | The Ins and Outs of Startup Investing

Right. And this is one reason that venture funds became content marketing machines and built brands. Do you remember? Like this is a recent phenomenon. I mean, maybe at best it was between 2005 and 10 is my memory when they started really coming out. Because in the 90s, I grew up in the Bay Area, lived there, I worked construction there, I didn't work in startups.

Startups For the Rest of Us
Episode 748 | The Ins and Outs of Startup Investing

Right. And this is one reason that venture funds became content marketing machines and built brands. Do you remember? Like this is a recent phenomenon. I mean, maybe at best it was between 2005 and 10 is my memory when they started really coming out. Because in the 90s, I grew up in the Bay Area, lived there, I worked construction there, I didn't work in startups.

Startups For the Rest of Us
Episode 748 | The Ins and Outs of Startup Investing

But there was like no, nothing published by venture funds. It was very, what do you call it? Information asymmetry is my memory of the whole thing. It was very opaque. You didn't know what term sheets, I didn't even know what terms meant, and everybody was hiding everything.

Startups For the Rest of Us
Episode 748 | The Ins and Outs of Startup Investing

But there was like no, nothing published by venture funds. It was very, what do you call it? Information asymmetry is my memory of the whole thing. It was very opaque. You didn't know what term sheets, I didn't even know what terms meant, and everybody was hiding everything.

Startups For the Rest of Us
Episode 748 | The Ins and Outs of Startup Investing

And it felt like in the early 2000s, mid-2000s, probably around the time YC, like Paul Graham and YC started coming up, the VCs started marketing themselves as the Andreessen Horowitz and the Sequoias, where they were putting out stuff. First round. First round.

Startups For the Rest of Us
Episode 748 | The Ins and Outs of Startup Investing

And it felt like in the early 2000s, mid-2000s, probably around the time YC, like Paul Graham and YC started coming up, the VCs started marketing themselves as the Andreessen Horowitz and the Sequoias, where they were putting out stuff. First round. First round.

Startups For the Rest of Us
Episode 748 | The Ins and Outs of Startup Investing

And then came 500 Startups and Techstars where it's like, here's content to help founders. Here's what a VC term sheet looks like. Here's what all these terms mean. Here's how you can get screwed by liquidation. And there's the preferred and then participating. And there's all these things that you didn't even know what they meant. Brad Feld, right? He wrote a bunch of books about it.

Startups For the Rest of Us
Episode 748 | The Ins and Outs of Startup Investing

And then came 500 Startups and Techstars where it's like, here's content to help founders. Here's what a VC term sheet looks like. Here's what all these terms mean. Here's how you can get screwed by liquidation. And there's the preferred and then participating. And there's all these things that you didn't even know what they meant. Brad Feld, right? He wrote a bunch of books about it.

Startups For the Rest of Us
Episode 748 | The Ins and Outs of Startup Investing

That was a big thing was for them to start, A, generating deal flow, but B, to get the trust, I think.

Startups For the Rest of Us
Episode 748 | The Ins and Outs of Startup Investing

That was a big thing was for them to start, A, generating deal flow, but B, to get the trust, I think.

Startups For the Rest of Us
Episode 748 | The Ins and Outs of Startup Investing

from people so they weren't come up because you were a commodity before it's kind of like if i'm gonna go borrow money for my house who's gonna give me the lowest rate we know with no prepayment penalty that's it it's commodity it's numbers and it's pricing and that's what i think venture was a little at least from my perspective was a little more like that at one point and then it became not right it became how do i get people to know me such that i do have some type of of pricing power and also a lot of inbound interest

Startups For the Rest of Us
Episode 748 | The Ins and Outs of Startup Investing

from people so they weren't come up because you were a commodity before it's kind of like if i'm gonna go borrow money for my house who's gonna give me the lowest rate we know with no prepayment penalty that's it it's commodity it's numbers and it's pricing and that's what i think venture was a little at least from my perspective was a little more like that at one point and then it became not right it became how do i get people to know me such that i do have some type of of pricing power and also a lot of inbound interest