Fun Raising
Claim This Podcastby Mat Vogels
Podcast Overview
<p>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.<br /><br />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.<br /><br />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.<br /><br />We put the "fun" in fundraising. Because someone has to.</p>
Language
🇺🇲
Publishing Since
3/7/2026
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Recent Episodes
June 16, 2026
Santiago Pliego | Vashon
<p>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. This isn't a generic "deep tech is hot" take. Vashon was deliberately designed to be capital that is native to this new paradigm, modeled on the merchant banks and trading companies of the 16th to 18th centuries that financed expeditions, secured supply lines, and took equity in the outcomes. The practical upshot is that Vashon operates in the same mountains and oceans as the founders it backs, front-running the upstream material and logistics bottlenecks those founders will eventually hit, and actively taking portfolio technology into regions where the geopolitical leverage is asymmetric. If you are building in mining, maritime, modular power, or anything that unlocks physical infrastructure, Vashon is not writing a check from behind a screen and waiting for a markup.</p><p></p><p>On pitch materials, Santiago makes a case that most early-stage founders should write a memo rather than a deck, or at minimum alongside one. The argument is operational: a memo removes the crutch of visual design and forces the founder to articulate the narrow problem sliver they have actually identified. His framing is that the most compelling pitch is not a large TAM but a demonstration that there is one specific cost curve or bottleneck hiding in plain sight across an entire value chain, one that nobody has identified, that if inverted would create a company worth $100 billion in that lane alone. He uses Durin Mining as a live example, noting that the materials Ted Feldman sent at the pre-seed stage were essentially a one-and-a-half page memo. For TAM, his take is dismissive: if the industry is well-understood (mining, maritime), you do not need a slide proving it is big. A TAM slide is only useful when the market itself is hidden, and even then, undershooting with a $1B number hurts more than it helps.</p><p></p><p>For the first meeting, Santiago is looking for what he calls the "beam them back a thousand years" test: would this founder be the one leading a group into battle, scaling a wall, conquering a city? He acknowledges this reads as abstract but is emphatic that it's the most predictive heuristic at inception stage, and that it manifests in observable ways, even in a first call. The single most common mistake he sees from technical teams is spending the meeting on component-level engineering depth rather than on company vision. The way he describes it internally: it feels like talking to a good engineering team inside Boeing or Lockheed, not a fast-moving startup. He extends this into post-close behavior: founders who immediately spin up a media and podcast circuit after closing a round are, in his view, signaling that what they wanted was the status of having raised, not the company itself. The FOMO that closes a competitive round should come through private group chats and word-of-mouth among the right people, not performative Twitter activity.</p>
June 9, 2026
Rishabh Surendran | Gaingels
<p>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 internship at Draper pitching deals directly to Tim Draper before landing at Gaingels. Because his fund follows rather than leads and writes smaller checks, his view of what a founder should want from an early investor is different from the default partner-at-a-lead-fund perspective.</p><p></p><p>His sharpest contrarian point is to stop obsessing over GPs and partners. The associates, senior associates, and principals actually run deal flow and respond faster, so win them and the partner conversation follows. He also argues founders wrongly write off a non-lead because it cannot cut a big check. He frames his own value as connective, making warm intros to leads he knows from Draper and elsewhere, and says that in one recent four-month stretch intros he sent by email led to over a million dollars of investment across a couple of companies (he cites checks around 750K and 350K). For cold outreach he wants the opposite of mystery: one or two plain sentences on what you build, what's next, and how much you're raising. Cryptic "cursor for defense" style one-liners are a turn-off for him.</p><p></p><p>On the round itself he leans hard on transparency, because investors verify with each other. He recounts a founder who claimed a soft commit from Draper that Draper flatly denied, which cost the founder both relationships. He warns against the oversubscription trap, where a planned 2M round creeps to 3.5M and over-dilutes because saying no to money feels wrong, and against valuations with no math behind them (the "next Nvidia" claim with no TAM logic), which scare off early investors. On the deck he wants a real team slide rather than just the founder's blurb, plus one clear product slide and a short five-slide send-ahead version. And he prefers first calls that open as a conversation, with slides shared only about 15 minutes in, when the technology genuinely needs them.</p>
May 26, 2026
Jake Storm | Felicis
<p>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.</p><p></p><p>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.</p><p></p><p>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.</p>
37 total episodes available
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Frequently asked questions
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- What is Fun Raising?
<p>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.<br /><br />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.<br /><br />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.<br /><br />We put the "fun" in fundraising. Because someone has to.</p> - How often does this podcast release new episodes?
This podcast updates daily.
- Where can I listen to this podcast?
This podcast is available on 4 platforms including Apple Podcasts, Spotify, and more. You can also use the RSS feed directly.
- Does this podcast accept guests?
Information about guest appearances is not available.
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