Co-Founder & Partner
First Round CapitalCheck size: $500K-$3M (seed only)
The seed-stage specialist. Invests earliest and deepest at seed — First Round was one of the firms that pioneered institutional seed investing. Built First Round into a platform that punches well above its check size — extensive founder community (~1000 active founders), expert network (First Round Network), and operational support. First Round Review (their media arm) produces some of the best tactical startup content anywhere — deeply researched guides on hiring, product, management, and go-to-market. Believes the best seed investors win by helping, not just funding. Josh's personal background as a serial entrepreneur (Half.com, Infonautics) gives him deep empathy for founders. He's lived the founding journey and knows what early-stage companies actually need. First Round's community model is a key competitive advantage — founders help each other, creating a network effect that makes the fund more valuable with every new investment. Known for being one of the most founder-friendly VCs — fast to respond, honest about passing, and genuinely helpful when invested.
First-time founders with deep domain expertise. Products solving a problem the founder has personally experienced. Strong product thinkers who build for users, not investors. Clear wedge into a large market. Founders who've talked to dozens of potential customers before building. Products with natural word-of-mouth or community dynamics. Evidence of user love even with small numbers.
Later-stage companies (seed only — don't come with a Series A ask). Companies without a clear product insight. Founders without a strong point of view on distribution. Companies that need large amounts of capital before demonstrating any traction. 'Solution looking for a problem' pitches. Founders who can't articulate why they specifically are the right person to build this.
They invest at seed — don't come with a Series A ask. Lead with the problem and your unique insight into it. They value product thinking over market analysis. Show you've talked to users — even 10 customer conversations matter. If you've experienced the problem yourself, lead with that story. Have a hypothesis about distribution. Don't overproduce your deck — substance over polish. First Round is fast — if they're interested, the process moves quickly. Read First Round Review before your meeting — it shows you understand their ecosystem and values. If you're building an AI-native product, show how AI is core to the value proposition, not just a feature.
The biggest barrier in conversion is between free and any price at all. Going from $0 to $0.01 loses more users than going from $1 to $100. This has major implications for freemium strategy, pricing psychology, and product-led growth.
First Round pioneered the 'VC as platform' model: the fund provides not just capital but a founder community, expert network, content (First Round Review), talent services, and events. The platform makes each investment more valuable and creates a network effect across the portfolio.
The most important thing at seed isn't the idea or the market — it's whether the founder has a uniquely deep understanding of the problem they're solving. Ideally, they've lived the problem personally. This gives them insight that can't be replicated by someone who discovered the problem through market research.
Even at seed, founders should have a clear hypothesis about distribution. Having the best product in the world doesn't matter if no one knows about it. Josh looks for founders who think about distribution as carefully as they think about product.
For both startups and venture firms, community is a defensible advantage. First Round's founder community creates value that pure capital can't — founders share knowledge, make introductions, hire from each other's networks, and provide emotional support during the hard times.
One of the best startup knowledge bases on the internet. Long-form, deeply tactical content on hiring, product management, engineering leadership, go-to-market strategy, fundraising, and company building. Based on interviews with experienced operators and founders. Each article is a masterclass. Examples: 'How Superhuman Built an Engine to Find Product/Market Fit', 'The Science of Speaking Up', and hundreds more.
The biggest conversion barrier isn't price — it's the gap between free and any price at all. Going from $0 to $0.01 is harder than going from $10 to $100. This has implications for pricing strategy, freemium models, and product-led growth.
Annual survey of hundreds of startup founders on fundraising, hiring, compensation, diversity, and market sentiment. Provides data-driven insights into what founders are actually experiencing.
“The biggest gap in conversion isn't from $10 to $1 — it's from $1 to free. That's the Penny Gap.”
— Blog posts and talks
“We don't just invest in companies — we invest in a community. Our founders help each other, and that network is our biggest competitive advantage.”
— Interviews about First Round's model
“The best seed investments come from founders who've experienced the problem so deeply that they can't NOT build the solution.”
— Interviews
“At seed, we're betting on people and insights, not metrics. The metrics come later. What we're looking for is a unique insight about the world that we believe is true.”
— Talks on seed investing
“I was a founder. I know what it's like to be terrified that you're going to let down your team and your investors. That empathy drives how we work with our companies.”
— Interviews
Serial entrepreneur turned seed investor. Founded Infonautics (internet search company) — IPO'd on NASDAQ. Founded Half.com (online marketplace for buying and selling at half price) — acquired by eBay for ~$350M just 6 months after launch. The Half.com story is legendary: Josh convinced Half.com, Oregon to rename itself to promote the site, generating massive press coverage. After the eBay acquisition, became Entrepreneur-in-Residence at Idealab. Co-founded First Round Capital in 2004 with Howard Morgan. Built First Round from a small seed fund into one of the most respected early-stage venture firms. Created First Round Review (firstround.com/review) — a knowledge base of long-form tactical content for startup founders, featuring deep interviews with experienced operators. Created the First Round Network (connecting founders to each other and to experts). Based in Philadelphia and New York, not San Francisco — intentionally broad geographic footprint. Known for the 'Penny Gap' concept — the biggest drop in conversion isn't from $10 to $1, it's from $1 to free. The gap between free and any price is enormous.