Fun Raising

Mat Vogels
  • 5.0 (2)
  • 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. 10h ago

    Alexandra Vidyuk | Beyond Earth

    Vidyuk is not a generalist software investor applying pattern-matching to hard science. She has a physics degree, three PhDs and a Nobel laureate on her team, and she writes $500K to $2M checks from pre-seed to Series B in fields most funds avoid on principle. That background changes the diligence itself: she spent 18 months studying fusion and concluded the technology is roughly 20 months from working, not the 20 years the consensus assumes, then made an unannounced investment on that call. The takeaway for founders is that a technical investor is running a different playbook, and the way to reach one is with substance, not polish. Her most useful advice reframes signals founders usually get backwards. Traction in deep tech is not revenue, it is evidence of hustle: sign 20 LOIs and she assumes 19 die, but she also knows you talked to 200 customers to get them, which she treats as the best available predictor of future sales. On positioning, she is blunt that VCs track you in PitchBook, Crunchbase, and Specter before you ever pitch, so she tells founders to audit their own database presence and check whether they would survive a sector filter. She also flags "zombie VCs" between funds and tells founders to check a firm's last investment date before spending time on a meeting. The through-line is that she wants to be the investor she needed as a founder. She describes the ideal founder as someone with a 20-year vision and three concrete tasks for next week, and she asks founders not to pitch the product first but to explain what will keep them going when the company gets hard. On closing, her guidance is patient and specific: never take the first term sheet, assemble a combination of leads by role rather than chasing the highest valuation, and reference-check investors by calling three of their portfolio companies to ask, directly, whether the investor was helpful or toxic.

    Alexandra Vidyuk | Beyond Earth

  2. 2d ago

    Paige Finn Doherty | Behind Genius Ventures

    Paige Doherty is a former engineer (Northrop Grumman, working on unmanned autonomous systems) who got into venture after writing a children's book about VC, and that background shapes a thesis most generalist seed investors don't share. She backs what she calls "technical storytellers," founders with deep domain expertise who can also communicate, and she writes $250K to $500K checks into overlooked markets with a path to billion-dollar scale. Notably, she co-invests rather than leading, but says she takes pride in having independent conviction, meaning she won't sit in a holding pattern waiting for a lead to validate a deal. For founders, that's a reminder that "we'll do it once you have a lead" is a choice some investors make and others don't, and it's worth asking early. Her most actionable material is on market sizing and outreach. She studied the last hundred-plus billion-dollar exits and found most companies were IPOing at $300M to $500M in revenue, and she expects that bar to keep rising, so she underwrites whether a founder can capture a meaningful share of a genuinely large market. Her tell: she likes when "1% of this market" is already a large dollar figure, because it shows margin of error on execution. On outreach, she's blunt that obvious AI-generated emails are a "beige flag," since communication quality is itself a signal of how the founder will handle customers and investors later. She wants brevity, a specific customer seeing ROI, and one sentence on why this founder is uniquely suited to the problem, the kind of detail "you can never AI away." The closing-phase advice is the most quotable. She frames a raise like a race: when the starting gun goes off, every conversation should start at roughly the same time so decisions cluster and momentum compounds through back-channeling. She's also specific on etiquette (BCC the person who introduced you so they drop off the thread, and send fast, well-written forwardable intros, pointing to Roy Bahat's post on the format). One honest moment worth noting: asked what mistakes founders make right after closing, she declined to give a pat answer, saying it's too early to tell that soon and easier to judge in hindsight. That refusal to manufacture a tidy lesson is itself a useful signal for founders sorting real pattern recognition from投 generic advice.

    Paige Finn Doherty | Behind Genius Ventures

  3. Jul 9

    Aaron Stachel | FirstMile Ventures

    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 that size lets him anchor a round without crowding out other investors, so he stays an ally rather than a bully for allocation. That geographic and structural position shapes everything he looks for. His most useful contrarian point is that team is not his first filter. The industry default is "we invest in people," and Aaron agrees team matters, but he evaluates the team only in light of whether the problem is big and urgent enough to justify a company. He goes further on where to hunt: obvious, hot problems (agentic guardrails, prompt injection) attract $50M seed rounds and teams spun out of the big labs, so a pre-seed founder is walking into a knife fight. He is drawn instead to offbeat, overlooked markets where a uniquely positioned founder teaches him something he'd never thought about, like an old industry still running on spreadsheets and WhatsApp. The red flag that mirrors this: founders who oversell, wave off competitors, and try to get him excited rather than taking his concerns two or three levels deep. He wants to be made comfortable with a risk, not talked out of caring about it. On process, the tactical advice is specific and worth the listen. Qualify VCs the way you qualify sales leads, and after two or three calls ask directly what's left in their process; a vague answer means they don't know what would get them to yes, and you should push or move on. Real FOMO comes from more demand than room in the round, not from fake caps or "closing Friday" deadlines that other VCs quietly fact-check with each other. And after the round closes, stop managing investors like prospects: your update should be a screenshot of the dashboard you already run the business on, shared honestly, bad news included. The weaker stretch is the "getting in the room" section, where the advice (warm intros beat cold outreach, target aligned investors) is fairly standard. Aaron's fresh wrinkle is that AI has flooded inboxes with polished cold emails, which has made warm intros and real-world relationships matter more than they did two years ago.

    Aaron Stachel | FirstMile Ventures

  4. Jul 7

    Kirby Winfield | Ascend

    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 underwrite growth. He frames his own value as narrow and purpose-built for the first check, and tells founders that if they don't want to take his call again after the first meeting, they shouldn't take his money. His sharpest point is counterintuitive: traction can be a negative signal at pre-seed. He wants to bet before a founder has quit their job or built a deck, because the strongest founders won't still be raising six months later. So $200K in revenue eighteen months in reads as evidence the company lacks exponential upside, not as de-risking. Pair this with his view on talent: founders should optimize for one extreme spike rather than being uniformly good. He diagnoses his own founder career as B-plus at everything and insanely good at nothing, which is why his companies sold but never went parabolic. He credits Jake Storm at Felicis for the "spikes" language. On mechanics he gets specific. The forwardable email should lead with a LinkedIn link, because most investors check your credibility there before reading a word of your blurb, and a stale profile can sink you before the pitch starts. The deck is a leave-behind, not a performance: send it ahead, keep it near 12 slides, and never read it aloud (he says he has never once gotten excited to invest after a founder walked him through slides). On closing, he endorses tranching as the most effective catalyst short of a tier-one term sheet, and dismisses the worry that early investors resent later, higher-priced ones, calling time-based valuation fairness a fiction.

    Kirby Winfield | Ascend

  5. Jul 2

    Adam Hammer | Roadrunner Capital

    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 machine, and the patterns it uses do not map well onto technically sophisticated founders coming out of national labs or university research programs. In his framing, those founders are not underfunded because they are weak; they are "mispriced" because the standard tools investors use to evaluate risk were not built for them. Roadrunner's pitch to founders flows directly from that diagnosis: the studio provides engineering staff, executive search, non-dilutive funding access, and capital syndication alongside its own check, and Hammer is explicit that capital should be "the least valuable thing we provide." The most practical framework in the episode comes from how Hammer thinks about the problem section of a deep tech pitch. He describes the most common failure mode as "a technology looking for a market," and he uses a vivid test to force the issue: who is the customer so desperate for your solution that they would sprint across a desert to reach it? He attributes the framing to a colleague named Steve Weinstein, but applies it himself to every pitch he reviews. The point is not about market size slides. It is about urgency, not opportunity. Hammer pairs this with sharp advice on investor selection that most founders never apply symmetrically: look for domain fluency over enthusiasm, and specifically ask whether a prospective investor has worked with technical founders before and whether their return timeline actually accommodates a decade-long build. His line on the alternative is worth writing down: "fast exit money is a slow motion problem." The least obvious advice in the episode arrives after the term sheet is signed. Hammer argues that founders trained by the fundraising process to obsess over capital efficiency need to make a hard switch the moment they close. His framing is that you are no longer "up against capital," you are "up against time." He sees technical founders in particular defaulting to a grant-funded research mentality, rationing resources rather than sprinting, and losing competitive ground to other teams who are moving faster. He also pushes back on the fear many first-time founders have about early cap table decisions. His view is that cap tables evolve across multiple rounds, and founders who spend too much energy negotiating marginal valuation terms during a seed raise are sending a bad signal while solving for the wrong variable.

    Adam Hammer | Roadrunner Capital

  6. Jun 25

    Bob Mason | Argon Ventures

    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 therapeutics company pitching a deep-tech fund, the warm intro won't save you, and he says so bluntly. His advice to founders building a target list is to rank investors by genuine portfolio alignment rather than blasting the top funds on a public sheet. The most useful material is his honesty about the asymmetry founders are walking into. He states plainly that a VC has no real incentive to tell you the true reason they passed, because they want to preserve optionality and avoid burning the relationship. He pairs that with a reps argument: VCs run hundreds of deals over a career while a founder runs a handful, so the only fix is building your own peer network to close the experience gap. On the deck itself, he pushes founders off the slide they tend to overbuild. Market sizing is table stakes that everyone games, so the leverage is in articulating competitive dynamics and a defensible technical moat instead. His first-meeting framework is concrete. He opens with "why this, why now, why this team," and he's listening for what he calls religious fervor, then storytelling ability, then a long-term technical moat. A founder who won't spar intellectually about their own product is a soft no, because at pre-seed he expects the first product to be wrong and is betting on learning speed. On closing, his repeated warning is against overplaying your hand: founders who manufacture false scarcity get caught, and the credibility hit is silent but real. When a round is oversubscribed, his frame is that the dollars are fungible, so choose the lead who can show you specifically how they've carried founders through the worst moments.

    Bob Mason | Argon Ventures

  7. Jun 16

    Santiago Pliego | Vashon

    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. 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. 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.

    Santiago Pliego | Vashon

  8. Jun 9

    Rishabh Surendran | Gaingels

    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. 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. 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.

    Rishabh Surendran | Gaingels
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Ratings & Reviews

5
out of 5
2 Ratings

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
    2026
  • Episodes
    43
  • Rating
    Explicit
  • Copyright
    © 2026 Mat Vogels
  • Show Website
    Fun Raising

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