5 HR AGO

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

1 DAY AGO

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

1 APR

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

1 APR

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

1 APR

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

30 MAR

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

30 MAR

Jordan Wan | CoFound

Jordan brings a go-to-market operator's lens that's genuinely rare among early-stage GPs. He ran one of the largest recruiting firms in NYC, scaling it across over a thousand startups, and that experience shapes everything about how he evaluates founders. His central investing framework is that founders and markets are mirrors of each other. He's not just looking at team pedigree or TAM slides. He wants to understand the rationality (or irrationality) of why someone started this business in the first place. A founder leaving a seven-figure salary to raise a gritty $1.5M pre-seed signals something fundamentally different than someone making a lateral career move into a well-funded seed. He also has a strong bias against what he calls "level one markets," the obvious problem spaces like recruiting or event platforms that anyone can see, and instead looks for founders with deep, earned insight into a specific industry. His approach to first calls is notably different from most VCs. He doesn't want to walk through the deck (he's already read it). Instead, he wants to riff on the founder's origin story, their worldview, and their vision for where their industry will be in five to ten years. He uses a "third inning of baseball" mental model: he wants to invest early enough that the trend hasn't fully played out, but late enough that there are real signs the founder's thesis is directionally right. Products change, features get rebuilt, pivots happen. Core beliefs are what compound. Founders who get defensive when challenged or dismiss hard questions are a major red flag for him, because if they can't handle tough questions on a Zoom call, how will they handle them from customers and employees? On the tactical side, Jordan gives founders a genuinely useful sales technique to close out investor calls: ask "What are your concerns about moving forward?" It invites honest feedback, eliminates ghosting, and gives the founder real signal on where they stand. He's also blunt about funding announcements, calling them one of the most common post-close mistakes. His argument: stealth is your greatest advantage at the early stage, and broadcasting what you're doing to the world rarely has asymmetric upside unless it's paired with a specific goal like recruiting or customer acquisition. And his biggest piece of long-term advice is to prioritize invalidating your hypothesis over validating it. If you're on the wrong track, you want to know as early as possible while you still have capital and time to pivot.

41 min

15 MAR

Mat Sherman | MatCap

Mat's model at MatCap flips the traditional VC playbook. Rather than writing large checks and picking winners, he invests at par value to get involved at the founding level, then makes introductions across his investor network to help founders close capital faster. It's closer to a high-volume accelerator than a traditional fund, and that scale gives him a unique window into what actually works in early-stage fundraising. His emphasis on "access transfer" as the core value proposition speaks directly to the structural problem he experienced firsthand: brilliant founders outside the Bay Area or traditional networks can grind for years without ever getting in front of the right people, not because their companies aren't good, but because the front door is too small. Some of the most valuable tactical advice in the episode centers on framing. Mat walks through how founders should answer the dreaded "are you raising?" and "who else is investing?" questions, explaining that the same truthful answer can be framed in ways that either build or kill momentum. He coaches founders to own their reality without sounding desperate, noting that saying "we kicked off last week, we've had ten calls, and you're among the first" is materially different from "no one's invested yet" even though both are true. He also pushes back on the common founder mistake of benchmarking their raise against Twitter success stories, reminding listeners that those overnight raises almost always have invisible backstories involving pedigree, networks, or family connections that aren't replicable. Mat is also refreshingly honest about the VC game itself. He explains that VCs often invest in more "legible" companies, not necessarily the best ones, because they need to raise their next fund, and backing something too unconventional can make that harder even if it might produce better returns. His advice to founders post-close is equally grounded: don't spend the money just because you have it, hire only when it's painful, and remember that you're not raising for 18 months of runway, you're raising for a milestone that lets you raise again. His candid admission that he made all of these mistakes himself at his first company, PubLoft, gives the advice real weight.

59 min

Fun Raising

Jason Chapman | Konvoy

Harrison Dahme | Hack VC

Larsen Jensen | Harpoon Ventures

Matias Zorrilla | Harpoon Ventures

Riley Loftus | Harpoon Ventures

John Forbes | Julian Capital & Deep Checks

Jordan Wan | CoFound

Mat Sherman | MatCap

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Fun Raising

Episodes

Jason Chapman | Konvoy

Harrison Dahme | Hack VC

Larsen Jensen | Harpoon Ventures

Matias Zorrilla | Harpoon Ventures

Riley Loftus | Harpoon Ventures

John Forbes | Julian Capital & Deep Checks

Jordan Wan | CoFound

Mat Sherman | MatCap

About

Information