Fun Raising

Welcome to Fun Raising, the podcast where the best early-stage investors pull back the curtain on the fundraising process, one founder question at a time. If you're a pre-seed or seed-stage founder trying to figure out how to get your first check, navigate a term sheet, or just understand what VCs are actually thinking when you walk out of the room — this is the show for you. Every episode, we sit down with top early-stage investors and put them on the spot with real questions from real founders. No fluff, no recycled advice, just honest, tactical conversations about what it actually takes to raise in today's market. From crafting your pitch to closing the round, we cover the moments that make or break a fundraise. We put the "fun" in fundraising. Because someone has to.

Fun Raising is a business podcast hosted by Mat Vogels, with 52 episodes on record and a Required Pod Score of 80. PitchCentric scores this show on Booking Probability, Listen Score, and live audience signals refreshed every 24 hours.

Mat Vogels hosts Fun Raising, a business show with 52 episodes published.

Our AI reads these to draft pitches. Use them as grounding for a pitch that cites a real guest and a specific topic.

• 

  Fun Raising

  Michael Gibson | 1517

  Sep 8, 202645 min

  Michael Gibson likes to say he has no business being in this business. He was working on a doctorate at Oxford in moral and ancient philosophy, following a T.S. Eliot-shaped plan to be a professor who wrote on the side, then dropped out, took a job at MIT's Technology Review, and on his first day working with Peter Thiel got pulled into announcing the Thiel Fellowship. He and co-founder Danielle Strachman ran that program for nearly five years: apply at 19 and under, and drop out of college if you were enrolled. Ethereum, Figma, and later Anthropic co-founder Chris Olah came out of those years. They named 1517 after the Protestant Reformation because they think the diploma is the modern indulgence — Yale or fail — and something like 90% of their investments have at least one founder without a degree. They are a pre-seed firm that likes being first money in, writing about a $100K check when a short experiment will prove a concept and about a million when there is a team and a plan. The part founders can actually use is how he runs a first meeting. It is not a yes or no on the check. It is whether they want to go deeper. What he is listening for is a trait he calls hyperfluency: speaking forwards and backwards about the industry, why past efforts failed, why this attempt will work, then scaffolding the same explanation up to an expert and down to "the dumb Labradors." Danielle calls the other tell dog-fighting-to-get-off-a-leash energy; they want to feel urgency, and they want to be the ones who snap the leash. Do the homework. He asked a founder last week if anyone on the team had a degree, heard that everyone was getting one and thought that mattered, and asked whether the kid had even seen 1517's website. Keep the deck to company, problem, solution, and team, 15 to 20 slides, and skip the AI-polished fake-personal email. If they go deeper, more of the team plus a subject-matter expert joins, they use SAFEs, and the process is supposed to take two weeks with a clear answer. He thinks founders should ask other investors the same questions — what is your process, what is your timeline — because too many firms stay secretive while they kick the can or wait for someone else to lead. The warning is that you cannot fake the first yes. The first commitment is always the hardest, and psychological FOMO will not manufacture it; if the tell that you are manipulating someone is too strong, it is a turnoff. One team told him they were using Robert Greene's laws of power on another investor. His reaction: are you stupid? Send weekly or biweekly updates instead, including who is actually in, and only get more direct with people who are leaning yes as a real close approaches. After the round, treat check-ins like mock board meetings and do not hide what is not working. Startups, he says, are the great revealer. You will have hard conversations every day, you will be wrong every day, and the one thing you cannot do is ignore the weaknesses they expose — shore them up or delegate, or you fail.

  ListenShow Notes
• 

  Fun Raising

  Ian Rountree | Cantos

  Sep 3, 202648 min

  Ian came up as an operator first. He joined SoFi at about 25 people, then became founding chief of staff at Invisible Technologies, where he and the CEO pitched roughly 100 investors, took 99 nos, and got one angel yes. Only four or five of those conversations felt useful. That knocked VCs off a pedestal and sent him into a year and a half of raising Cantos I. He started the firm when hardware and the real world were uncool, against a mentor who treated the idea like a slap. Now investing out of Fund IV with partner Grant as a first-check GP, he lets entrepreneurs tell him where the future is going. At idea stage he underwrites the people, not the industry, model, or go-to-market on the deck. The tactical spine is that the warm network is the real inbound. Ian has only ever invested in one cold inbound, so a trusted founder calling someone special beats any deck. X is how you warm a cold DM: lurk, post, and show up already known. When a deck does land, he reads it backwards, Tom Perkins style, then tabs to the team page first and texts mutuals. First calls are booked at 30 minutes but they block 90. Internally they score founders on six attributes he will not name, then test for a gravity-well vision. If you want a $10 billion company in 10 years, you are creating something like $20 million of value a week, and the world has to warp around you. Intellectual answers are table stakes. After the call he wants to feel fired up enough to run through a brick wall. The warnings are as specific as the screen. Do not pitch a second idea when they pass. It reads like a trinket salesman opening the coat. If the call is asymptoting to no, end it. Do not lie, fake FOMO, or write a tier-one name on the whiteboard and pretend you forgot the last meeting. Ask for portfolio references only after they have asked to invest, and include a company that failed. When you have a choice, pick the board you can live with for twenty years over the highest valuation. After close, hiring is the work. Use the 409A strike-price window sparingly for one key hire, then run an investor onboarding session so they get put to work. Fundraising is a numbers game. When Ian complained to an entrepreneur about 100 LP meetings, the reply was, my man, you're just getting warmed up.

  ListenShow Notes
• 

  Fun Raising

  Patty Wexler | Avila VC

  Aug 20, 202646 min

  Patty Wexler is not a default VC. She spent the first half of her career funding consumer internet at a $1.9B firm, then made a deliberate bet around 2015 that "so much IQ and so much capital in this little zip code" could not keep chasing the same three ideas. She now invests out of a small fund one at seed to A, across nuclear fusion, industrial automation software, magnesium, and drilling tech. That combination, a consumer-software pedigree plus an engineer's bias toward the physical world, is why her advice skips the usual talking points. Her most useful reframe is about the power dynamic in a first meeting. Founders walk in braced for a skeptical loan officer; Wexler says the opposite is true, that she is hoping to be sold and is leaning in. The practical version of that is calibrating your pitch to what the investor already knows. If you are solving nuclear energy, do not spend a slide on how big the energy market is, because everyone gets it. Save the TAM case for markets she cannot size in her head, and if you are one of a thousand teams building the same agentic tool, spend that time on why you specifically. Her read on VC attention is blunt: it is drifting toward "fruit fly level," so lead with the hook and elaborate later. A related prep tactic is to run a search on yourself before pitching, the way you would before a date, and assume any lazy investor will spend one minute doing the same. On process, she sets expectations founders rarely hear stated plainly. Investors are "an inch deep, a mile wide," so expect lateral insight and warm intros, not domain depth you already own. Her diligence ranges from a single weekend when she knows the founder and space to six or eight weeks to a term sheet plus a couple more months to close the syndicate when she is leading cold. The most actionable framework is how to sequence the raise: do a few test runs with firms that are good but not your first choice, then concentrate on your target firms, then work the rest, so a middling firm is not deep in your process when your dream firm finally engages. She also normalizes the quick no (nobody holds a grudge over a fast, clean pass) and the reminder that you are always fundraising, so you should not wake up six months from cash-out and start cold.

  ListenShow Notes
• 

  Fun Raising

  Arkady Kulik | Arkane

  Aug 13, 202640 min

  Arkady is a scientist and repeat founder who moved into venture specifically to solve a translation problem he kept watching play out: deeply technical founders who can't tell their story, meeting VCs who can't tell whether the science is real or "Theranos 2.0." That background shapes a fund that behaves differently from a default seed check. He leads first rounds, wants to be the first VC on the cap table, and screens on two questions only when he opens a deck: what have these founders understood that nobody else has, and what problem space are they in. Everything else is secondary. The tactical advice is where the episode earns its time. On outreach, he wants founders to build three or four tiers and start with a "tier zero" of friendly VCs they don't even need, purely to rehearse the pitch and burn through the rough reps before approaching the firms they actually want. On decks, he argues the competition slide is close to useless at pre-seed, because any static two-by-two is a snapshot of a moving target, and early companies die from execution, not from competitors. On process, he time-boxes hard: a non-fit founder is out inside 30 minutes, and even a serious diligence path costs no more than three and a half hours of the founder's time, run through a questionnaire, a scientific partner, and a business partner before a final call. He treats a slow, ambiguous process from other VCs as usually a soft no, not a maybe. His most contrarian material is about the money itself. He ranks capital plainly: revenue first, debt second, equity last, and calls equity the worst money a founder can raise because it loads on the most liability and the most outside expectations. He refuses to celebrate a close, and warns against "suicide rounds," raising too much at too high a valuation too early, then spending like the cash will never run out. His fix is unglamorous: park it in treasuries and behave as if you never raised. He's equally direct that manufactured FOMO is an instant pass, since reputation in this market dies in hours, and that most failures trace back to execution and founder psychology rather than the balance sheet.

  ListenShow Notes
• 

  Fun Raising

  Matt Logan | Earthshot Ventures

  Aug 6, 202643 min

  Matt Logan is a GP at Earthshot Ventures, a climate fund spun out of the nonprofit Elemental. What separates him from a default climate investor is that he doesn't lead with decarbonization. He looks for companies that win because they are cheaper, better, or faster, with the climate benefit as a byproduct of the core value prop rather than the pitch itself. His thesis, the clean intelligence stack, runs the length of the AI supply chain, from critical minerals up through data center energy, compute efficiency, AI-native applications, and physical AI, which is where he expects most of the next decade's power-law outcomes to sit. The most useful thing for a founder is his honesty about sourcing. Of seventeen investments in fund one, nine came from his own cold outbound and eight from his network. None came from a founder's cold email. His takeaway is not that founders should stop trying, but that the leverage is in becoming someone worth reaching out to: early traction, a strong team, and small checks from smart angels in your market who can refer you (he'll take a meeting off a $1K check from someone sharp). He also frames access as "legibility." The less legible you are to capital, the more you should target firms that specialize in your exact stage and sector instead of chasing multistage brand names. In meetings he weights founder intensity, clarity on business model, and unit economics above a deep technology walkthrough, and he would rather a founder name a weak unit economic openly than leave it as the elephant in the room. Two closing tips stand out. First, diligence the investor by talking not only to the references they hand you but to the founders of their portfolio companies that went under, because that is where you learn how a VC behaves when things go badly. Second, keep terms clean (standard YC SAFE docs), optimize for complementary skill sets over valuation, and remember that stated numbers are often flexible once a VC has gotten to yes. And if you are struggling to raise, his advice is blunt: go back and build, because traction relative to your resources, the inflection rather than the absolute number, is what unlocks a round. Product market fit, as he puts it, covers over almost any other sin.

  ListenShow Notes

Recent guests on Fun Raising. Study who booked and why before you pitch.

Based on semantic analysis of episode topics and host coverage, this show is a strong guest fit for executives in:

Industry fit is computed by PitchCentric using vector embeddings of the show's episode catalog.