The Unconventional VC: Maddi Holman of Daring Ventures

Yeah, it definitely takes longer than you think.

And I think a big piece is figuring out how to qualify LPs faster.

I think a big piece of going into it was assuming that everyone that had a family office online that was going to be interested in venture, that's not always the case.

A lot of them don't actually invest in venture and are in different alternative assets.

So really figuring that out and... being able to see, is this an opportunity for now or is this building a relationship for fun two or fun three? And so that was a big piece that we learned and being very clear on our thesis as well.

Like you've got to be able to pitch it and then to understand it in two sentences.

So in two sentences, you teed me up.

So in two sentences, if you wouldn't mind discussing the thesis with us.

So if somebody's hearing about Daring Ventures for the first time, we very briefly touched on the company density thesis in the beginning.

But if you wouldn't mind, tell us who is Daring and what are the types of companies that you're looking to target?

For Daring, we really are targeting companies, as you mentioned, with the density piece.

So when you look at company building now, it's so easy to build very polished, high-quality-looking solutions.

And so it's harder to distinguish projects from generational companies.

And what you really have to look for is how much of that generational company is compressed into the company today.

A lot of times that's through a initial wedge that a company is building against a specific workflow in complex work usually, and they're solving an initial pain point for their ICP that then can lead to a larger workflow.

And so a lot of times that may look like a feature, it may look like a point solution at first, but if you can see the path for it to grow, and that's something that Joe's really good at, that is where we see companies that compound and grow versus others that may spend time trying to figure out who the actual customer is or the right product.

So that's really how we think about it.

But all B2B, vertical SaaS, applied AI, we really like industries that are complex, long procurement cycles, regulated.

Because there's, I think, from your lived experience and people who are in those industries, there's nuances to it.

So you understand what is the problem and who's the buyer and how do you approach them.

Yeah, it definitely takes longer than you think.

And I think a big piece is figuring out how to qualify LPs faster.

I think a big piece of going into it was assuming that everyone that had a family office online that was going to be interested in venture, that's not always the case.

A lot of them don't actually invest in venture and are in different alternative assets.

So really figuring that out and... being able to see, is this an opportunity for now or is this building a relationship for fun two or fun three? And so that was a big piece that we learned and being very clear on our thesis as well.

Like you've got to be able to pitch it and then to understand it in two sentences.

So in two sentences, you teed me up.

So in two sentences, if you wouldn't mind discussing the thesis with us.

So if somebody's hearing about Daring Ventures for the first time, we very briefly touched on the company density thesis in the beginning.

But if you wouldn't mind, tell us who is Daring and what are the types of companies that you're looking to target?

For Daring, we really are targeting companies, as you mentioned, with the density piece.

So when you look at company building now, it's so easy to build very polished, high-quality-looking solutions.

And so it's harder to distinguish projects from generational companies.

And what you really have to look for is how much of that generational company is compressed into the company today.

A lot of times that's through a initial wedge that a company is building against a specific workflow in complex work usually, and they're solving an initial pain point for their ICP that then can lead to a larger workflow.

And so a lot of times that may look like a feature, it may look like a point solution at first, but if you can see the path for it to grow, and that's something that Joe's really good at, that is where we see companies that compound and grow versus others that may spend time trying to figure out who the actual customer is or the right product.

So that's really how we think about it.

But all B2B, vertical SaaS, applied AI, we really like industries that are complex, long procurement cycles, regulated.

Because there's, I think, from your lived experience and people who are in those industries, there's nuances to it.

So you understand what is the problem and who's the buyer and how do you approach them.