Fun Raising

Aaron isn't a default VC. He spent ten years as an Army helicopter pilot and a West Point grad before an MBA pulled him into startups, and in 2015 he co-founded FirstMile with Bill Miller to be the first check for founders building in non-coastal markets. He writes $400K to $800K into rounds generally below $2M and leads roughly a third to a half of them, which he frames as deliberate: a check tha...

Winfield is a four-time operator (two IPOs, two acquisitions) who spent two years as investor-in-residence at the Allen Institute for AI before launching Ascend in 2019. That background drives a blunt thesis most polished VCs won't say out loud: pre-seed money from finance-trained "quants" is dangerous, because the people writing first checks need to understand the zero-to-one journey, not underwr...

Adam's route to running a venture studio puts him in a different position than most people giving fundraising advice. He came up through investment banking at Goldman Sachs, then spent time at Eric Schmidt's family office, and then worked inside a post-quantum encryption startup before founding Roadrunner. That last stint is the one that shaped the thesis: traditional VC is a pattern-matching mach...

Bob Mason isn't a finance-first VC. He spent his career as a software engineer and CTO, building two enterprise companies from team formation through public offering, and he invests the way an operator reads a room. That shows up in how he triages: before opening a deck, the only question is whether the company maps to a pattern already in Argon's portfolio. If you're a consumer shopping app or a...

Santiago Pliego built his thesis around a specific macro claim: the last 70 to 100 years represent an anomaly characterized by globalized Pax Americana, the offshoring of physical industry, and a massive over-rotation into software and financial abstraction. His argument is that we are now exiting that anomaly and returning to hard physical things, national sovereignty, and critical supply chains....

Rishabh is a pre-seed deep tech and frontier specialist at Gaingels, a 12-year-old venture syndicate that does not lead rounds. Instead it co-invests behind a lead at roughly 10% of the round (typically 250K and up at pre-seed and seed). His background is atypical for a VC: engineer trained in India, a stint at Goldman, deploying deep tech for the Indian government in remote terrain, then an inter...

Jake Storm came to venture through an unusual route: enterprise software sales at Qualtrics and Zuora, then investment banking (including working on Zuora's IPO), before Felicis. That background shapes how he thinks about founder outreach, pitch construction, and the investor relationship in ways that are meaningfully different from investors who came up purely through finance or pure operating. H...

Kenan brings a perspective that's rare even among founder-turned-investors: he's sitting inside one of the most visible early-stage programs in venture (Speedrun sees 20,000+ applications per cohort) while being only about six months into his role at a16z. That freshness means his advice isn't abstract or ten years removed from the founder experience. He sold his first company, Halo, to Lyft, got...

Zal isn't your average seed investor. He's the solo GP behind Refactor Capital, a hard tech seed fund based in Burlingame, and he just closed his fifth $50M fund. Before going solo, he spent a decade in product at Google, Netflix, and LinkedIn, then jumped to A16Z where he helped launch the Bio Fund. Today, he writes $1-2M checks into energy, aerospace, robotics, bio, and health. The cap tables he...

This is the role-reversal episode where Mat steps out from behind the host mic and gets grilled by Ali Rohde about his own playbook. Mat invests at Harpoon Ventures (deep tech, $1M to $5M checks) and runs Black Flag, Harpoon's pre-accelerator that often writes the very first check into companies before they've even incorporated. He came up as a YC founder (Zestful, killed by COVID), pivoted into V...

Kyle's path into VC is unique and worth the listen on its own. He was a cybersecurity consultant who started the Secure Ventures podcast during COVID simply because he wanted a "How I Built This" for cyber CEOs. That podcast became his accidental entry into venture, and it informs a lot of his advice: he has literally interviewed hundreds of founders in the trenches, so his pattern matching is gro...

Jacob comes at fundraising from an unusually operator-heavy angle. Julian Capital is staffed entirely by ex-growth people (Julian himself ran growth at multiple billion-dollar companies), and they don't just write checks. They embed with portfolio companies on growth, design, branding, and storytelling. On top of that, Jacob runs DeepChecks, which the team describes as the world's largest fundrais...

Jack's path into VC is anything but standard: he spent his teens and college years as a professional online poker player until the DOJ shut down online poker in 2011, did a brief hedge-fund stint, then moved to Silicon Valley in 2013 as a sales engineer at Box before building two of his own venture-backed startups. His first real SPV investment, Oats Overnight, returned 12x and hooked him on ventu...

Alex Roetter brings a rare operator's DNA to venture. Before co-leading Moxxie Ventures with his partner Katie, he ran engineering at Twitter and led an eVTOL (electric flying car) company. Moxxie writes $500K to $2M checks at the pre-seed and seed stage, and Alex's background shapes how the firm shows up for founders: concrete, in-the-trenches conversations about customer problems and go-to-marke...

Natty brings a perspective that's rare in early-stage VC: he's a founder-turned-Techstars MD-turned-fund partner, giving him an almost uniquely high volume of reps with early-stage companies. One of his most actionable frameworks is how founders should think about investor qualification. Rather than casting a wide net, Natty argues your top priority is finding the investor who already believes in...

AJ brings a genuinely distinctive lens to venture. He built defense tech at 16, opened for the Eagles on violin, and had Glenn Fry as a songwriting mentor. That creative background directly shapes how he coaches founders on storytelling: take the biggest, most complex engineering idea in the universe and get it stuck in everybody's head in the shower. It's not just a metaphor for him. It's the act...

Jason Chapman brings a distinctly technical lens to early-stage investing. Before launching Convoy in 2018, he was an engineer at IBM's artificial intelligence division, writing code 12 to 18 hours a day. That background shapes how he evaluates deals: he wants to be the most knowledgeable investor on a founder's cap table, going deeper than the typical mile-wide-inch-deep approach. Convoy writes c...

Harrison brings a rare perspective to the fundraising conversation as both a repeat founder and one of the few CTO-titled partners in venture. He's spoken to roughly 4,000 companies over the past four or five years, and his advice is grounded in seeing both sides of the table. One of his most practical suggestions is around pitch deck structure: he gravitates toward the appendix first, looking for...

Larsen offers a masterclass on the art of the initial pitch, and his core message is counterintuitive: less is more, everywhere. He argues that if you can't communicate your team, problem, and market in four sentences in your outreach email, go back to the drawing board, because longer emails don't signal thoroughness, they signal desperation. He extends this to the pitch meeting itself, noting th...

Matias brings a rare perspective to early-stage investing: he spent years at Goldman and Bank of America helping late-stage and public companies raise hundreds of millions in capital before joining Harpoon Ventures to focus on pre-seed through Series A. That background gives him a clear-eyed view on what founders get wrong about storytelling and financial positioning. His core thesis on pitch deck...

Riley brings a perspective shaped by volume. Between Harpoon's deal flow and the hundreds of applications coming through Black Flag, he's reviewing more pitch decks than most early-stage investors, which gives his feedback on what actually stands out real weight. His advice on decks is refreshingly practical: stop overbuilding TAM slides (VCs will do their own market sizing anyway), make sure some...

John brings a rare dual perspective to this conversation. On the Julian Capital side, he's evaluating deep tech deals at pre-seed and seed across hardware-intensive sectors like robotics, materials, energy, and space. On the Deep Checks side, he's built a platform specifically to solve what he calls the "matching problem" in deep tech, where unlike software, it's genuinely unclear who the right th...

Jordan brings a go-to-market operator's lens that's genuinely rare among early-stage GPs. He ran one of the largest recruiting firms in NYC, scaling it across over a thousand startups, and that experience shapes everything about how he evaluates founders. His central investing framework is that founders and markets are mirrors of each other. He's not just looking at team pedigree or TAM slides. He...

Mat's model at MatCap flips the traditional VC playbook. Rather than writing large checks and picking winners, he invests at par value to get involved at the founding level, then makes introductions across his investor network to help founders close capital faster. It's closer to a high-volume accelerator than a traditional fund, and that scale gives him a unique window into what actually works in...

Andrew brings a rare lens to early-stage investing. Eight years defusing bombs for the Navy, a stint at Stanford, and time embedded as interim chief of staff at a portfolio company gave him both operational instincts and a deep respect for founders who can lead under pressure. His litmus test during pitch calls is simple: "Do I want to go work for this person?" He's not looking for the most techni...