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. Kyle McNulty | In-Q-Tel

    1 DAY AGO

    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
  2. Jacob Jackson | Julian Capital

    6 DAYS AGO

    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
  3. 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
  4. 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
  5. Natty Zola | Matchstick Ventures

    16 APR

    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
  6. AJ Smith | Outlander VC

    14 APR

    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
  7. Jason Chapman | Konvoy

    8 APR

    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
  8. Harrison Dahme | Hack VC

    7 APR

    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
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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
    31
  • Rating
    Explicit
  • Copyright
    © 2026 Mat Vogels
  • Show Website
    Fun Raising