Fun Raising

Mat Vogels
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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. Natty Zola | Matchstick Ventures

    3D AGO

    Natty Zola | Matchstick Ventures

    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 your thesis and has been looking for you. Your second priority is the open-minded investor you can convert into a believer. The anti-pattern is trying to convince a non-believer, which is just a waste of time. He also flips the perceived power dynamic, reminding founders that VCs literally don't have a job without entrepreneurs building companies. On the fundraising process itself, Natty emphasizes that fundraising is sales with one critical twist: unlike normal sales, you want every "customer" to close at the same time. That means running a disciplined, compressed process where you're actively speeding up some investors and slowing down others to get multiple parties near a decision simultaneously. He also prefers memos over pitch decks ("sizzle vs. steak"), gravitates first to team and competition slides, and wants founders to have three "must-airs" for every meeting, regardless of format. His advice on ending meetings is practical: always leave with a follow-up that's your responsibility, and create lots of small touchpoints rather than long updates. Perhaps the most distinctive advice comes post-close. Natty's concept of "hiring in arrears vs. hiring in advance" is a framework every seed-stage founder should internalize. His recommendation: raise the round and don't spend any money for three months. Hiring in advance means filling roles you think you need; hiring in arrears means waiting until you're drowning in a specific task, so you know exactly what success looks like in that role and you hire better for it. He ties this directly to why most startups fail: they didn't make enough progress relative to the capital they had. The ratio of progress to capital is the most important metric for a startup.

    47 min
  2. AJ Smith | Outlander VC

    5D AGO

    AJ Smith | Outlander VC

    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 actual skill he evaluates when a deck lands in his inbox. He spends about 90 seconds on a pitch deck, and if he can't understand the business by reading headline to headline across 10-15 slides, it's a pass. That "headline test" is one of the more concrete, actionable pieces of pitch deck advice we've gotten on the show so far. On process, AJ is refreshingly direct. Outlander reviews over 5,000 deals a year and invests in about 15, writing checks from $500K to $2.5M as a true pre-seed lead. Their diligence is deeply relationship-driven. They use a 20-point founder assessment framework and spend 10-15+ hours getting to know founders before committing, which AJ compares to spending at least as much time together as contestants on The Bachelor before getting married. He also pushes back on the common "tight two-week process" claim, noting that manufactured urgency is usually transparent and can backfire. Instead, he recommends honest momentum building, stating where you actually are with other investors and letting that naturally create urgency. One of the most valuable threads in this episode is AJ's take on what happens after the round closes. He warns against the post-raise "I can conquer the world" trap, where founders lose focus and try to do everything at once. But the bigger issue he flags is founders hiding problems from their investors. Outlander has helped navigate co-founder breakups, toxic early hires, and product failures, but only when founders are honest about what's going wrong. His blunt advice: save the rose-colored glasses for your customers and your grandma, and give your investors the truth.

    49 min
  3. Jason Chapman | Konvoy

    APR 8

    Jason Chapman | Konvoy

    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 concentrated $3-5M checks, doing only six to eight investments per year, and Jason has led follow-on rounds up to five times into the same company. His pitch to founders is straightforward: his personal net worth is tied up in the fund, so every check carries real weight and aligned incentives. The tactical fundraising advice throughout the episode is where founders will get the most value. Jason lays out a specific cold outreach formula: find 50+ funds by looking at who backed tangential, non-competitive companies, then craft a two-to-three sentence email with a provocative opening line. His hot take is that LinkedIn actually outperforms email because most investors have heavy spam filters that catch attachments and unknown senders. He also recommends linking to a DocSend deck rather than attaching a PDF, and shares a pre-call tactic a founder used on him that he loved: sending a prep email two days before with five key takeaways and the top two reasons other investors were passing. That kind of transparency, front-running the bad news, softened the blow and built trust immediately. Jason is also candid about the red flags that kill deals fast. Co-founder tension on a call is an instant pass, fabricating term sheets or timelines will get exposed because VCs talk to each other, and having all four co-founders on an intro call reads as a yellow flag rather than a show of strength. On the post-raise side, he warns against overhiring in engineering before revenue catches up, and encourages founders to think seriously about whether they even need more than one or two equity rounds. His closing advice gets personal: make sure your spouse is fully aligned before you start, and build a support system because building a company is incredibly lonely.

    56 min
  4. Harrison Dahme | Hack VC

    APR 7

    Harrison Dahme | Hack VC

    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 deep technical detail that reduces the number of follow-up meetings needed. For founders building anything with a technical edge, he recommends investing in that appendix section to answer the first round of questions proactively, rather than sticking to the standard seven-to-ten slide formula. His most memorable framing is around the cap table itself. Harrison pushes back hard on founders who optimize for ownership percentage at the expense of strategic composition. He frames it as "growing the pie" versus "getting a larger share of the pie," and encourages founders to think about what each investor on the cap table uniquely brings, whether that's distribution, technical support, or something else. He also warns that the end of a fundraise is where founders most often reveal character flaws. He's walked deals where a founder suddenly became difficult once they had leverage, which is a red flag for a relationship that's supposed to last years. On the process side, Harrison is candid about the constraints VCs operate under. He schedules 30-minute calls with 30-minute breaks to clean up notes, and he's explicit that founders who drag their feet on follow-up materials will lose priority fast. He talks to around 20 companies a week, so responsiveness matters. He also flags a specific credibility killer: claiming you're closing by end of month when you have no commits. He says you only get to play the FOMO card once, and burning it on a bluff can end the relationship entirely.

    32 min
  5. Larsen Jensen | Harpoon Ventures

    APR 1

    Larsen Jensen | Harpoon Ventures

    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 that experienced VCs essentially know their interest level within the first five to ten minutes, meaning the rest of the call is just validating or invalidating that initial gut reaction. This reframes the entire first meeting: it's not a 30-minute presentation, it's a five-minute audition followed by a conversation. His advice on warm intros is blunt and specific. Introductions through existing portfolio founders are the number one path in, by a wide margin, with everything else a distant second. He explicitly warns against cold outreach and even cautions founders about coming in through other VC firms that passed on the deal, because the first question any investor will ask is "why didn't they invest?" For founders without a warm network, Larsen draws from his SEAL background: do the ground game months ahead of time through conferences, relationship building, and earning trust from other founders in your space, before you ever need to fundraise. Perhaps the most distinctive thread is Larsen's framing of the diligence and closing phases as a prioritization battle. He reminds founders that they're not just competing against other deals for a VC's capital; they're competing against every other obligation on that investor's calendar, from troubled portfolio companies to their own fundraising. The practical takeaway: create a compressed, competitive process that forces urgency, and learn to read engagement signals like a courtship. If a VC is calling, texting, and digging into the data room, they're interested. If it's radio silence, take the hint. And when it comes time to pick investors, optimize for partner quality over valuation every time. As Larsen puts it, optimizing for price at the early stage is almost an indictment on your own confidence in how big the outcome can be.

    51 min
  6. Matias Zorrilla | Harpoon Ventures

    APR 1

    Matias Zorrilla | Harpoon Ventures

    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 decks is refreshingly simple: he cares about founders and market, and almost nothing else at the early stage. He actively discourages founders from including detailed revenue projections or elaborate TAM slides, arguing that speculative financials can actually work against you because investors will anchor to those numbers later. Instead, he wants to see a narrative arc: what's the problem, why hasn't anyone solved it, and what makes your technology the unlock. One of his most practical insights is about team slides, which he says are one of the most commonly botched elements of a pitch deck. The mistake he sees constantly is founders listing their name, title, and a few company logos with zero context. He points out that without a brief explanation of what you actually did at those companies, investors will fill in the blanks themselves, and usually not in your favor. He'd rather see a first-time founder with no brand-name experience write two honest sentences about their connection to the problem than see a wall of impressive logos with no substance behind them. Matias also offers sharp advice on the late stages of fundraising. When a round gets oversubscribed and founders have to make hard choices about their cap table, he urges radical transparency: email each investor individually, explain the situation honestly, and ask if they'd be willing to adjust their check to make room. He warns against the temptation to over-optimize for ownership percentages or valuation at the earliest stages, pointing to the Silicon Valley joke about a founder wishing he'd taken a lower valuation. His parting advice is equally grounded: think of each fundraise not as an isolated event but as one leg of a lifelong capital-raising journey, and give yourself real margin for error on how much money you'll need to hit your next milestone, especially if you're building hardware.

    57 min
  7. Riley Loftus | Harpoon Ventures

    APR 1

    Riley Loftus | Harpoon Ventures

    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 someone can understand what your product actually does within the first few pages, and don't waste money on a fancy design agency. He points to MatX's deck, which was literally black text on white slides, as proof that substance wins. For technical founders, his rule of thumb is to explain your product like you're talking to your middle school cousin, then go deeper in subsequent slides. On the meeting and diligence side, Riley emphasizes something founders often underestimate: the personal and conversational dimension. He actually prefers no-deck intro calls where the conversation flows naturally, and he's a fan of founders who spend the first five or ten minutes on personal connection rather than diving straight into the pitch. The energy and passion a founder brings in the first few minutes tells him more than most slides ever could. His biggest red flag? Founders who seem frustrated when asked to simplify their explanation, or who talk over your head rather than meeting you where you are. He also shares a smart tactical tip: ask the VC upfront whether they're actually deploying capital right now, and how long their diligence process typically takes, so you don't waste a month only to learn the fund is between vehicles. Perhaps the most distinctive advice comes around post-close discipline and the broader fundraising mindset. Riley warns against the classic early-stage trap of over-hiring and over-spending right after closing, and he stresses treating your next ten hires almost like co-founders. On valuation, he pushes back on the temptation to take the highest number offered at the seed stage, arguing that an inflated early valuation can set you up for a painful Series A if you can't justify the step-up. And his closing advice ties it all together: the best founders are the ones willing to adapt, whether that means pivoting the business, adjusting the raise size, or accepting a lower valuation to get the right investors around the table.

    42 min
  8. John Forbes | Julian Capital & Deep Checks

    MAR 30

    John Forbes | Julian Capital & Deep Checks

    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 thesis-fit investor is for any given company, and even investors' own sector preferences shift quarter to quarter. That combination means John sees the funnel from both ends: the founder trying to get in front of the right people, and the infrastructure trying to make that connection happen at scale. His most actionable insight might be around how deep tech founders need to think about market pull differently than software founders. Because switching costs in physical industries can involve retooling manufacturing lines or changing entire supply chains, the bar for demonstrating that customers genuinely want your product is significantly higher. John zeros in on the problem and solution slides as the most important in any deck: is this a severe bottleneck for the customer's business, and is your solution an order of magnitude better than what exists? He's less interested in top-down market sizing (he'll ask for bottom-up math anyway) and more interested in whether the pain is real enough that buyers will endure months of integration friction to adopt. The episode is also packed with tactical advice on running the fundraising process itself. John recommends treating it like a sales funnel of 100 to 200 funds, using well-written cold emails with calendar links (no need for heavy customization beyond a first name), and ending every investor call by asking "how close is this to your wheelhouse and what are your main concerns?" That last move, he says, catches the investor while they're fresh and gets you real-time objection handling before they move on to 10 other meetings. He also cautions against over-promising on round momentum, noting that VCs talk to each other and dishonesty erodes trust fast.

    44 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
    27
  • Rating
    Explicit
  • Copyright
    © 2026 Mat Vogels
  • Show Website
    Fun Raising