How I Invest with David Weisburd
Hosted by David Weisburd
Written by a model from the transcript; not yet reviewed.
This episode explores how long-term relationships, community building, and contrarian thinking built a venture capital firm to $3.6 billion in assets under management. The guest explains how early investments in companies like Shopify, Airbnb, and Riot Games relied on trusting exceptional founders against consensus opinion, and details the firm's network effect strategies known as guilds. The conversation covers the importance of giving before getting, navigating economic downturns during difficult fundraises, and the rising cultural trend of real-life human connection.
The episode opens with a discussion on how relationships, rather than capital or brand, are the most powerful driver of long‑term success in venture investing.
David explains how First Mark built a tight network of early New York entrepreneurs and later expanded it into guilds that provide specialized expertise across industries.
David and the host discuss how niche, high‑signal information from a focused network fuels better investment theses and faster decision‑making.
The conversation shifts to how First Mark’s network helps founders quickly solve operational problems, illustrating the power of real‑time, peer‑to‑peer advice.
The episode explores the philosophy of giving value first, maintaining authenticity, and nurturing long‑term ties to create a self‑reinforcing network.
David shares stories of early, contrarian bets—Airbnb, Pinterest, DraftKings—and how a willingness to back great founders with unconventional ideas led to outsized returns.
The discussion turns to the inevitable setbacks startups face, how First Mark supports them, and the importance of resilience and learning from failure.
The conversation explores how AI‑native founders and emerging mega trends shape First Mark’s investment strategy, emphasizing the need to stay ahead of technological shifts.
David reflects on raising funds during the 2008 crisis, the lessons from his entrepreneurial past, and the mindset required to persevere through market downturns.
The episode concludes with final reflections on the power of relationships, the importance of giving, and the enduring value of a well‑maintained network in venture investing.
Explores techniques for asking powerful questions to uncover honest feedback and improve personal strengths.
Discusses using hypothetical scenarios to challenge leaders and foster open-mindedness.
Starting in New York Venturestory
The guest recalls launching First Mark in 2005 when New York was the seventh biggest venture market, fitting the entire local ecosystem into a small office.
Bionic Networks Through Guildsstrategy
First Mark built specialized professional guilds numbering over 80,000 members where operators can solve niche problems without direct firm involvement.
The Rule of Giving Firstinsight
Relationships fail to compound when individuals expect immediate returns instead of approaching interactions from a position of abundance and generosity.
Contrarian Shopify Investmentstory
Shopify challenged existing enterprise e-commerce infrastructure by offering website creation as a service, empowering everyday entrepreneurs, and using an app ecosystem.
Founders with Zero Direct Reportsdata
Many CEOs who eventually scale to run companies with tens of thousands of employees had exactly zero direct reports in their careers prior to starting.
Raising Fund Two During the Crisisstory
The firm spent 20 months raising their second fund during the global financial crisis, facing doors slammed in their face before reaching their target.
“Clearly, relationships, because the world seems to get smaller every day, especially here in New York City, where you have the ability to start very small, but the same people keep showing up again and again as investors, as entrepreneurs, as operators, and as friends.”
“You have to give before you get. And that's often hard, especially when you're starting out. So you have to give before you get early on, even if you don't have that much to give.”
“The bigger the network, the more you could slice it, right? So you can have finance people that are Series B and C companies in New York. And maybe there's 22 people in that guild, but that's enough.”
“The more specific the vertical, the less people know the right answer to questions. And the more niche, the more the community matters.”
“You try to be crisp. You try to be able to answer the question and you try to be very factual.”
“I think relationships are scalable. You can build a bigger, broader network.”
“I have a great LP that's been with us since the beginning, small, but a great Philly sports fan, and I'm from Philly.”
Consumer startups may grab the headlines, but some of the most valuable companies are built by solving mission-critical problems for businesses. David sits down with Rick Heitzmann, Managing Director at FirstMark Capital, to discuss how he identifies high-growth technology-enabled business services, why sectors like data infrastructure, compliance, marketing technology, and information services continue to generate outsized opportunities, and what separates enduring enterprise businesses from short-lived trends.
11,348 words · 2 speakers
Speaker names marked are inferred from speaking time and the show’s known hosts — they are not voice-verified.
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