The Dart Board with Daniel Dart

Meet Matt Kraning, Partner at Menlo Ventures.Matt's path to venture started accidentally through a stopover in Afghanistan. He was mid-PhD at Stanford when he stopped out to join DARPA, the Department of Defense's advanced research arm, and spent two years as their data scientist on the first operational DARPA program since Vietnam. When he came home, he co-founded Expanse with the people he'd met on that program, bootstrapped it on DARPA contracts, before eventually raising a seed round from Peter Thiel. He would go on to build Expanse into a category-defining business and exit for $1.25 billion to Palo Alto NetworksIn this episode, we get into what that time in Afghanistan actually taught him about surviving startup hell, why he thinks founders need to be right rather than popular, how he tests for the ability to learn fast instead of a chip on the shoulder, and why he believes most VCs are a commodity and only a few actually earn the check they write.

Meet Keri Findley, founder of Tacora Capital, one of the most exciting new specialty finance investment firms in the world today.Keri started Tacora five and a half years ago with backing from Peter Thiel, after spending the back half of her career at Third Point cutting credit deals with some of the world's biggest new fintech companies like SoFi, Upstart, and Lending Club. But long before she made her mark on Wall St, she was building discipline as a competitive figure skater training at 5 am. In this episode, we dig into all of it, from the difference between lending against assets and buying them, why she thinks "follow your passion" is bad advice, and what a decade of compounding hard work actually looks like in practice.

Meet Ted Schlein, executive chairman and general partner of Ballistic Ventures, and general partner at Kleiner Perkins since 1996.Ted has been in the cybersecurity industry really since it began, helping build one of the first major companies in the sector, Symantec. He then joined Kleiner Perkins, where he has been involved for over three decades, during which he founded another cybersecurity darling, Fortify Software. And if that wasn't enough, he recently founded another venture firm, Ballistic Ventures. Very few people have had the staying power and success of Ted, and in this episode we dig into a bit of everything spanning his generational run - which is still going on today. We close by learning a bit about the stories that shape him and the best advice he picked up along the way.

Meet Joanne Chen, General Partner at Foundation Capital.Foundation has been investing for over three decades, focused on seed and Series A, backing companies before product-market fit around two mega trends: AI and blockchain. The firm has had 35 IPOs, including Cerebras, which it incubated in its own offices. Joanne joined almost twelve years ago after being introduced to the firm by co-founder Kathryn Gould. Before venture, she was an engineer, a banker, and even spent a few years on the placement agent side before making the jump to investing.In this episode, we get into how Foundation turns customer conversations into investment ideas, what she found interviewing companies for what she calls The Great Reorg, why raising more capital doesn't mean returning more capital, why she got less attached to outcomes and more attached to growth, and why she thinks venture is a human psychology exercise rather than a pattern-matching one.

Meet Howard Morgan, Chair and General Partner of B Capital and one of the true pioneers of venture capital. Prior to B Capital, Howard co-founded First Round Capital with Josh Kopelman, served as founding president of Renaissance Technologies with Jim Simons, and was machine 50 on the ARPANET back in 1973. He spent more than a decade as a professor before going full-time into investing, and over the past 50 years, he has backed some of the world's biggest companies, including Uber, Roblox, and Square.In this episode, we go all the way back to the early internet and why he saw email coming before almost anyone, then into building Renaissance and the decision to split venture from quant. Howard tells the story of how First Round started as essentially two full-time people and returned roughly 50x on its second fund, including the blank check that became Uber and the eight-year-old who pitched the team on Roblox.We also get into why he joined B Capital, why he asks for the bad news first, and the best advice he ever received standing in a computer center in 1965.

Micah Rosenbloom is a General Partner at Founder Collective, one of the original true seed funds, founded in 2009 before seed was even a recognized category.Before he was a VC, Micah co-founded three companies, including Brontes Technologies, which was acquired by 3M. He then spent four years inside 3M running the acquired business, which gave him something most investors don't have: a real operator's view of what a startup looks like after it lands inside a 65,000-person company. Founder Collective has backed Uber, The Trade Desk, WHOOP, Shield AI, Verkada, Suno, and Airtable across five intentionally small funds.In this episode, we cover why fund size drives every strategic decision that follows, the shift from cottage industry to firm-building and what operators-turned-VCs get right that others are still learning, why the best investments in the portfolio were always that way in the early days and what that means now, the founder psychology required to survive hardware's valley of death, and what staying small when everyone else scaled actually costs, and why Micah would do it again.

Meet Paul Klein, founder and CEO of Browserbase.Paul started his career at Twilio, where he saw firsthand what it looked like to make something programmable that wasn't designed to be. He spent time at Mux building headless browser infrastructure before founding Browserbase himself and taking it from zero to Series B in under 18 months. The company is backed by Kleiner Perkins, CRV, and Notable Capital, with customers including Ramp, Stripe, Vanta, and Vercel using Browserbase to power their agents across the web.In this episode, we get into why the web wasn't built for agents and what Browserbase does about it, the better lesson, and why rebuilding the internet for AI is probably a temporary hack, what solo founding at Series B actually looks like, why he hires for agency and judgment over credentials, and why optionality is a curse.

Meet Caroline Duffy, Partner at Cowboy Ventures. From flying to Guatemala to observe call center workers alongside Andrew Ng in the early days of AI, to watching it come full circle and now investing in the companies that used to just be ideas, she has gotten to work alongside some of the best AI researchers in the world and now invests alongside icons like Aileen Lee at Cowboy.In this episode we get into her labor shortage economy thesis and why the real AI opportunity in critical sectors is not about replacing workers but finding them, why she thinks defense is overhyped and overrun with tourist investors, her take on humanoids, why overfunding at seed is one of the fastest ways to kill a company, and the best advice her dad ever gave her.

Meet Sheel Mohnot, co-founder and GP at Better Tomorrow Ventures.Born and raised in Pittsburgh, before entering venture, Sheel lived on $1 a day in India doing microfinance work, built and sold two companies, and co-founded Thistle, a healthy food delivery business now generating north of $100M in revenue. He started investing out of his own pocket before raising a proof-of-concept fund in 2017, then launched BTV and is now on their third fund.In this episode, we get into why the contrarian and right trope only tells half the story of how venture actually works, how Sheel thinks about portfolio construction after going from 80 companies to 30, why specialization lets you win deals you have no business winning on price alone, what 2021 did to emerging markets and whether it ever comes back, and the mentor who told him that doing hard things and writing about them might just be the greatest hack in the game.