Episode summary
The Unconventional VC: Maddi Holman of Daring Ventures
Dakota Live!
· · 44 min · Hosts: Robert Morier · Guests: Maddi Holman, Joseph Alalou
Summary
The guest explains how Daring Ventures was built around a nontraditional path into venture capital and a thesis focused on pre-seed B2B vertical SaaS and applied AI. She and her co-founder came to investing from different routes, and she argues that those outsider backgrounds help them spot founders with real domain depth rather than polished narratives. The firm’s core idea is “company density”: in an age when products are easier to build, the harder thing to fake is a business with a sharp wedge, strong customer understanding, and a credible path to expansion.
A major theme is how to separate real traction from surface-level momentum at the pre-seed stage. The guest says the firm looks for proof that founders understand the buyer, the workflow, and the compliance or operational nuances of a market, especially in complex industries. She uses examples from home services, life sciences, and restaurant technology to show how point solutions can become larger platforms when they capture proprietary data or unlock adjacent workflows.
She also discusses fundraising, LP selection, and what the firm learned from raising its first fund. Daring Ventures wants to stay under $100 million and keep its model close to traditional venture, while using events, thought leadership, and market trips to source overlooked founders outside the usual network. The guest closes by discussing her podcast, Let's Be Heard, which focuses on women's health and the gaps in research, stigma, and policy that still limit adoption of better solutions.
Key takeaways
- The guest says Daring Ventures backs pre-seed B2B vertical SaaS and applied AI, with a focus on complex, regulated workflows.
- She argues that “company density” matters more as building gets easier: the best startups compress more of a future category leader into the product today.
- The guest says many strong pre-seed founders are overlooked because they do not fit traditional venture networks or backgrounds.
- She uses ServiceTitan, Practis Pro, and Hosty to show how narrow wedges can expand into larger platforms by capturing proprietary data and adjacent workflows.
- The guest says Daring Ventures wants to stay under $100 million and prove its thesis consistently across funds.
Notable quotes
“what you really have to look for is how much of that generational company is compressed into the company today”
“it was actually my junior year in college. Uh they offered us a shadowing course. Um we were right next to the Houston Med Center”
“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 highquality looking solutions”
“we went to 15 states and really focused on cities where we thought there was alignment from like an industry perspective with our our thesis”
“there's still a stigma around listen like believing women around when they say something hurts or something doesn't feel right”
How the episode opens
Welcome to the Dakota Live podcast. I'm your host, Robert Morier. The goal of this podcast is to help you better know the people behind investment decisions.
We introduce you to chief investment officers, manager research professionals, and other industry leaders to help you sell in between the lines and better understand the investment sales ecosystem. If you're not familiar with Dakota and our Dakota Live content, please visit our website at dakota.com. Before we get started, I need to read a brief disclosure.
This content is provided forformational purposes and should not be relied upon as recommendations or advice about investing in securities. All investments involve risk and may lose money. Dakota does not guarantee the accuracy of any of the information provided by the speaker who is not affiliated with Dakota.
Not a solicitation, testimonial, or an endorsement by Dakota or its affiliates. Nothing herein is intended to indicate approval, support, or recommendation of the investment adviser or its supervised persons by Dakota. Today's episode is brought to you by Dakota Marketplace.
Are you tired of constantly jumping between multiple databases and channels to find the right investment opportunities? Introducing Dakota Marketplace, the comprehensive institutional and intermediary database built by fundraisers for fundraisers. With the COD marketplace, you'll have access to all channels and asset classes in one place, saving you time and streamlining your fundraising process.
Say goodbye to the frustration of searching through multiple databases and say hello to a seamless and efficient fundraising experience. Sign up now and see the difference Dakota Marketplace can make for you. Visit dakota marketplace.com today.
Welcome back to the Dakota Live podcast. Our guest today is Mattie Holman. Mattie is co-founder and general partner of Daring Ventures.
Daring Ventures is a New York-based venture capital firm investing at the preede and seed stages.
From the episode’s captions: roughly the first two minutes, lightly cleaned. Keep watching on YouTube →
Topics
- venture capital
- pre-seed investing
- b2b vertical saas
- applied ai
- limited partners
Companies and tickers mentioned
- Daring Ventures
Watch the episode
Watch “The Unconventional VC: Maddi Holman of Daring Ventures” on YouTube
Summary, takeaways and quote selection by Octagon. Quotes are short excerpts; the full conversation is in the episode.
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Dakota Live!, this episode and its artwork belong to Robert Morier. Octagon is not affiliated with the show; this page is an independent summary.
