Fun Raising

Mat Vogels
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  • Entrepreneurship

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.

  1. Jake Storm | Felicis

    5 days ago

    Jake Storm | Felicis

    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. He treats both cold outreach and pitch structure through a sales lens, and he's skeptical of the academic approach most founders take to both. The most actionable part of the episode is Storm's framework for what he actually evaluates in a pitch. He argues that founders over-index on TAM slides, which he calls "a rudimentary approach to articulating why there will be market pull." What Felicis actually wants to see is a sharp "Why Now" construction: evidence that this is the right moment, that the founder has seen something the market hasn't yet, and that they can show it clearly within the first few minutes of a meeting. His test is blunt: if 15 to 20 minutes into a first meeting the unique insight still hasn't surfaced, it is very hard to recover. Storm also makes a pointed case for tiering your investor list by individual partner fit, not fund brand, and spending time proportionally rather than treating every name on your CRM as equally worth pursuing. One of the more useful tactical pieces Storm offers is a question he tells founders to ask investors directly: how many of the founders you work with are pinned at the top of your messaging apps? It's a simple proxy for how actively a VC actually works with their portfolio, and it reframes the pitch dynamic in a way founders often don't consider. He also makes a distinction between "conviction investors" (funds that move on their own belief) and those waiting for a signal from another investor before committing, and says founders would do well to understand which type they're talking to before investing heavily in a relationship. On post-close mistakes, his view is clear: the most common failure is over-optimizing for investor feedback during fundraising and losing the customer-obsession that should be driving the company.

    43 min
  2. Kenan Saleh | Andreessen Horowitz

    19 May

    Kenan Saleh | Andreessen Horowitz

    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 exposed to a16z through Ben Horowitz's board seat, and went back to building before eventually crossing over to the investor side. His advice is practical and grounded in what he's watching founders do right now, in real time, through the Speedrun program. One of the most counterintuitive takeaways from this conversation is Kenan's stance on pitch decks. He argues that most investors barely look at the deck before a first meeting. They're scanning the email blurb, clicking through to your LinkedIn, and making a snap judgment on whether the team and category are interesting enough to warrant a conversation. Founders, he says, should be spending far more time on how they present themselves online and how they tell their story in the room than on making a beautiful 30-slide deck. He even suggests that the best first meetings often don't use a deck at all, favoring a more conversational dynamic where the investor can ask questions and the founder can demonstrate depth and conviction in real time. The other standout advice is around process discipline. Kenan recommends founders build investor lists of 100 to 200 funds (not the 20-30 most founders default to), and he references Vinod Khosla's point that time spent preparing for a fundraise may be more important than the fundraise itself. He also has a clear framework for handling oversubscription: rather than running a bidding war on price, he advises founders to identify the best long-term partner and then ask that partner to match competing offers. It's a less adversarial approach that he believes leads to better outcomes for the company over the long run.

    32 min
  3. Zal Bilimoria | Refactor Capital

    14 May

    Zal Bilimoria | Refactor Capital

    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 sits on read like a hard tech hall of fame: Solugen, Astranis, Orchid Health, YourChoice Therapeutics, Vitra Labs. And every founder he backs gets free mental health therapy through Lyra Health, on his dime. Not many seed funds do that. The first half of the episode is a masterclass in cold outreach and first meetings. Zal's mental model for a fundable founder is sharp: they need to be "magnets for customers, talent, and investors," which means being both technically and commercially gifted, and a great storyteller. He breaks down his "test pitch" approach (start with 5-10 friendly VCs before expanding to 50+), why he reads every deck on his phone (and decides in 30 to 60 seconds), and the specific tells that lose him in pitches: reading off the screen, low energy, no homework on him as an investor. He's also refreshingly direct on decks: 10 slides max for a teaser, use Claude to design it for $10 in tokens, and stop spending $50K on deck designers. Where the episode really pays off is the back half on round construction and post-close mistakes. Zal lays out his "airport layover test" for picking investors, argues hard against optimizing for the highest valuation, and explains why a "village" cap table beats a single lead. He's also blunt about the post-close trap first-time founders fall into: a six-month hiring crawl driven by second-guessing, when the real test is one or two days in office with the candidate. And he closes with what may be the most actionable advice in the episode for hard tech founders: the fastest way to make your next round easier is to get a third party (LOI, pilot, paid contract) to validate your tech so the next VC doesn't have to do de novo diligence.

    37 min
  4. Mat Vogels | Harpoon Ventures

    12 May

    Mat Vogels | Harpoon Ventures

    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 VC via Julian Shapiro, and treats VC itself like a product, building tools like VC Sheet and pitchrec.com to make the fundraising process less opaque for first-time founders. He's bullish on cold email in a world where everyone else worships warm intros, sharing the story of how he raised his first check with an all-emoji email to Shrug Capital. He thinks pitch decks are quietly dying because firms like Harpoon now run every incoming deck through AI before a human ever opens it. And he's brutal about what he's actually looking for in the first meeting: not your idea (he's seen a dozen versions of it, including the ones you think are unique), but whether you have the energy and depth to go a thousand miles deep on this for the next decade. On closing, he lays out the most honest cap table framework I've heard in a while: roughly 60% of VCs are net zero on your company, 25 to 30% are net negative, and only 10% are net positive. The goal isn't to chase the positives, it's to avoid the negatives. He also breaks down a "wave approach" to building real FOMO without lying, and offers a counterintuitive post-raise warning: today's bigger mistake isn't spending too much, it's still acting frugal when you've raised real money and need to deploy it fast.

    52 min
  5. Kyle McNulty | In-Q-Tel

    5 May

    Kyle McNulty | In-Q-Tel

    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 grounded in what works, not just what pitches well. The In-Q-Tel model itself is something most founders have never had explained clearly. Kyle walks through both check types: a standard ~$250K equity check designed to build early relationships, and a larger $1 to $3M check that comes bundled with a paid design partnership and statement of work between the startup and one or more federal agencies. That second structure means In-Q-Tel's diligence is genuinely different from a typical VC, often closing between rounds rather than on a round, and requires building internal champions on the agency side. For any founder whose technology could serve national security, this is a playbook you rarely hear articulated. On the fundraising mechanics, Kyle is refreshingly blunt about things founders get wrong. He pushes back on seed founders who only chase tier-one logos, warns that VCs absolutely do text each other to verify claims about your process, calls out how a six-minute self-intro reads as insecurity, and shares why being cagey about revenue or hiding behind NDAs is an instant red flag. He also offers a sharp framing on FOMO: the real buzz isn't created by pushing hard on any single investor, it's created when three different investors independently mention your company to each other in the same week.

    40 min
  6. Jacob Jackson | Julian Capital

    30 Apr

    Jacob Jackson | Julian Capital

    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 fundraising platform for deep tech, built to match founders with the specific investors who actually fund their sub-sector and stage. That gives him a rare dual perspective: he sees both the supply side (thousands of founder pitches) and the demand side (the full universe of deep tech VCs) of the market. The throughline of his advice is that fundraising should look more like a sprint than a marathon. He pushes founders to "measure twice, cut once" by building a full investor list, prioritizing it, getting practice reps with lower-priority funds first, and then running a tightly time-boxed process (2 to 3 weeks if you're experienced, a couple of months max for first-timers). He's blunt about why a six-month raise is a yellow flag, why every email and deck gets unconsciously graded as a proxy for how well you'll run the company, and why "velocity" (speed plus direction) matters more than raw effort. He also reframes the first investor call: by the time you're on the call, the idea has already passed. The investor is now evaluating whether you're the right founder for that idea. The episode gets especially tactical in the back half. Jacob lays out a concrete tranching strategy where the first million comes in at a lower valuation, the next at a higher one, and so on, rewarding early conviction and avoiding the "land the plane" problem of trying to close everyone at one cap. He's refreshingly direct about why founders over-index on valuation, what to do with the cash the day it lands (pre-plan your hires, use grants and financing for equipment, don't burn equity dollars on things you could rent), and why monthly investor updates with a consistent template often turn into next-round preempts. It's a useful playbook for any deep tech founder thinking about how to prep, run, and survive after a round.

    44 min
  7. Jack Dreifuss | Impatient Ventures

    28 Apr

    Jack Dreifuss | Impatient Ventures

    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 venture. Now on Fund 2 of Impatient VC, he runs a thematic strategy across deep tech (defense, reshoring, manufacturing) and consumer AI, framing both as national-security bets on "saving the West." He writes $1–3M early-stage checks and $10M+ growth checks, and calls his core craft "serendipity maximization." The thread that runs through the entire episode is what Jack calls "relentless authenticity." He's convinced founders consistently underestimate how much investors are reading them, not the deck, and that most rejections are actually about the founder. His single favorite screening question is: "If this startup crashes and burns, what are you going to do next?" Any answer that smells like a concocted Plan B is a red flag. He wants founders willing to commit an entire life to the mission, not just grind to the next milestone, and he leans heavily on a Viktor Frankl line: "who has a why will find a how." On the mechanics of fundraising, Jack is refreshingly blunt. He has responded to exactly two cold emails in three years of investing; warm intros (especially from his LPs and portfolio founders) drive almost everything. Decks should explain the business in the first slide, full stop. He feeds confusing decks into AI and asks for a "12-year-old explanation," and he calls out jargon-heavy pitches as "LARPing." His framework for what a VC actually delivers is tight: capital (a commodity), perspective, and access. And when a VC passes, he says, stop rationalizing it as "they didn't get the business." They got it. They just passed on you. Let it go, move on, and keep being relentlessly yourself.

    50 min
  8. Alex Roetter | Moxxie Ventures

    21 Apr

    Alex Roetter | Moxxie Ventures

    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-market strategy rather than board decks and process theater. The through-line of the episode is Alex's full rejection of what he calls "finance bro culture" — the posturing, the middle-school-dating negotiation tactics, the manufactured urgency. He has strong, contrarian takes on how founders should approach their outreach list, what actually matters in a first meeting, and why a lot of the "strategy" founders obsess over is a waste of the one resource they can't get back. His advice on evaluating VCs, in particular, reframes the decision in a way most founders don't think about until it's too late. The most valuable segments, and the ones most likely to be uncomfortable, are on fund dynamics, tier-one dynamics, and dilution. Alex draws a hard line between "great companies" and "great venture investments," and is blunt about the traps founders fall into when they raise more than they need at terms the market will reward in the short term but punish later. He closes with what might be the most honest framing of the whole conversation: a successful fundraise isn't success. It's just the bar being raised.

    36 min
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About

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.

Information

  • Creator
    Mat Vogels
  • Years Active
    2k
  • Episodes
    35
  • Rating
    Explicit
  • Copyright
    © 2026 Mat Vogels
  • Show Website
    Fun Raising

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