Fun Raising

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...

Grant brings a rare perspective to the fundraising conversation because he came up through the industrial world, not finance. He started in oil field operations, worked pipeline infrastructure across Texas, Louisiana, Pennsylvania, and beyond, then helped build out a corporate venture arm from scratch before joining 8090. That hands-on background means he's evaluating founders less on polished dec...

Brett's approach to pre-seed investing is built entirely around the founder, not the idea. At a stage where most companies have little to no traction, he goes straight to the team slide and digs for founder-market fit, how the team met, and why this specific group of people will push through when things get hard. His take on pitch meetings is equally refreshing: he doesn't want a presentation, he...

Josh brings a unique lens to deal sourcing that most founders simply don't understand. Rather than chasing hot sectors or famous brands, he actively looks for what others are missing, reasoning that the majority of early-stage venture capital lives in the Bay Area, and whatever that community can't or won't think about is exactly where the overlooked opportunities hide. His investment themes, rang...

Philip Carson brings a refreshingly contrarian perspective to fundraising from the jump: most startups shouldn't be raising venture capital in the first place. Rather than treating VC as the default path, he pushes founders to honestly assess whether they actually need outside capital or whether they're chasing the idea of being a venture-backed founder. This framing sets the tone for an episode f...

Arthur's most distinctive contribution in this episode is his "campaign plan" framework, borrowed directly from his Marine Corps background. Rather than just pitching a product vision, he wants founders to show a sequenced, interdependent plan where each milestone unlocks the next. He shares a real example of a three-month-old defense startup that already had a mapped path to their first program o...

Brandes brings a refreshingly candid perspective on what early-stage investors actually care about, and it might surprise you. When she opens a pitch deck, she scrolls straight to the team slide and almost nothing else. Not the market size, not the financials, not the roadmap. Just the team. For a fund like Also Capital that writes concentrated inception-stage checks, they are making a bet on a pe...

Ethan brings a rare dual lens to this conversation: he spent years as a founder who couldn't get a meeting, then became a managing director at Techstars, where he reviewed thousands of pitches. That combination gives him a clear-eyed view of what actually moves the needle versus what founders obsess over that doesn't matter. His most counterintuitive point: the pitch deck is mostly a red herring....

Eric brings a refreshingly practical framing to fundraising: it is a process, not a pitch. He emphasizes that founders should treat every phase, from outreach to diligence to closing, as a structured workflow. That means building a list of 50 to 100 firms, drilling down to the right individual at each fund (not just the fund itself), and staying on top of communications with a simple tracking syst...

Adam's biggest throughline is that how a VC behaves during the fundraising process is exactly how they will behave as a partner for the next decade. He is unusually direct about this, encouraging founders to treat the diligence phase as a mutual interview and to do back-channel reference checks on investors just as VCs do on founders. He gives a sharp breakdown of the VC landscape too, suggesting...

Jakob brings a refreshingly practical, no-nonsense perspective to early-stage investing, shaped by building his own community-based fund in El Segundo, the hardware and defense-tech hub that grew out of SpaceX's roots in LA. Unlike most VCs, Discipulus runs a physical two-week residency that front-loads the relationship-building, network access, and demo day prep that most founders spend 6-12 mont...