Fun Raising

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.

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.

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.

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.

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.

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.

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.

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.

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.

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.

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.

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.

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.

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.

Andrew brings a rare lens to early-stage investing. Eight years defusing bombs for the Navy, a stint at Stanford, and time embedded as interim chief of staff at a portfolio company gave him both operational instincts and a deep respect for founders who can lead under pressure. His litmus test during pitch calls is simple: "Do I want to go work for this person?" He's not looking for the most technically dense presentation. He's looking for a compelling human being who can attract exceptional people and tell a story worth following. For founders who tend to lead with jargon or stats, that's an important recalibration.The most tactical segment is a fundraising strategy Andrew picked up from a founder in the Stardex accelerator. Before formally raising, you build a list of target firms, start coffee chats, and end every conversation with: "I'm not raising right now, but when I do, do you want me to call you?" Then you score each firm's enthusiasm as a percentage, multiply it by their average check size, and keep going until the total hits 300% of your target raise. Only then do you formally kick off, starting with your highest-conviction contacts. It's a framework that turns relationship-building into a measurable, repeatable system, and the founder who used it raised from multiple tier-one firms without ever sending a pitch deck.Andrew also delivers a sharp warning about the post-raise mindset. He sees too many founders close a round and then freeze, clinging to a scarcity mentality instead of deploying capital to hire the best people, engage top-tier PR, and accelerate growth. At the same time, he flags the opposite trap: lying about commitments to manufacture urgency. VCs talk to each other constantly, and claiming you have a verbal offer that doesn't exist is what Andrew calls the number one sure way to kill a deal. The through-line across the whole conversation is that early-stage fundraising is fundamentally a people game: build real relationships, tell an honest and compelling story, and don't try to shortcut trust.

Grant brings a rare perspective to the fundraising conversation because he came up through the industrial world, not finance. He started in oil field operations, worked pipeline infrastructure across Texas, Louisiana, Pennsylvania, and beyond, then helped build out a corporate venture arm from scratch before joining 8090. That hands-on background means he's evaluating founders less on polished decks and more on what he calls "hyperfluency," the ability to talk about your technology, go-to-market, and vision at any altitude, from a fifth grader to a deep technical audience. He's explicit that domain credibility doesn't require 20 years of experience; he believes the information age has leveled the playing field for younger founders who've gone deep.One of the spicier takes in this episode is Grant's view on the TAM slide: he doesn't want to see it. He argues that in well-known industrial sectors, founders and investors both already understand the market, and the time spent making a pretty SAM/TAM/SOM chart is better spent showing how you'll dominate your beachhead. He also flags a subtle but important red flag: when the CEO isn't the one doing most of the talking in the pitch. At 8090, they don't like "regime change," so they need to see that the person in the CEO seat is the one who can carry the company from seed to IPO.Grant also offers sharp tactical advice on round construction and post-raise execution. He encourages founders to set their raise target at the minimum of their range (say $10M instead of $10-20M) to avoid the optics of an undersubscribed round. He's a strong advocate for strategic angels, arguing they're "worth their weight in gold" because their hands are less tied than institutional VCs. And post-close, his advice is clear: spend the money, hire fast, and don't develop a scarcity mindset. The capital is meant to accelerate your mission, not sit in the bank.

Brett's approach to pre-seed investing is built entirely around the founder, not the idea. At a stage where most companies have little to no traction, he goes straight to the team slide and digs for founder-market fit, how the team met, and why this specific group of people will push through when things get hard. His take on pitch meetings is equally refreshing: he doesn't want a presentation, he wants a real conversation.Founders who come in reading slides or rattling off name drops lose him fast. He's looking for emotional intelligence, self-awareness, and someone who can show their passion without slipping into sales mode.On the process itself, Brett gives some genuinely tactical advice that doesn't get talked about enough. He recommends founders have recorded customer calls and testimonials ready in their data room before diligence even starts, since reference calls are a bottleneck that can slow a round by a week or more. He also prefers investment memos over slide decks because the writing reveals the depth of a founder's thinking in a way that slides never can. And when it comes to building the cap table, he cautions against letting one large fund take the entire round, pointing out how dangerous that signal becomes if you miss your metrics and that fund walks in the next raise.Brett also doesn't shy away from what happens after the check clears. His warning to post-raise founders is one worth sitting with: once you have investors with opinions, you need a very strong filter. VCs have incentives, and those incentives don't always align with what's best for your business. The founders he most respects are the ones who move fast, stay honest, trust their gut, and filter feedback without losing conviction. His closing advice is almost provocatively simple: stop thinking about fundraising, and just build.

Josh brings a unique lens to deal sourcing that most founders simply don't understand. Rather than chasing hot sectors or famous brands, he actively looks for what others are missing, reasoning that the majority of early-stage venture capital lives in the Bay Area, and whatever that community can't or won't think about is exactly where the overlooked opportunities hide. His investment themes, ranging from population decline to human enhancement to "portal fatigue," are not random. They're the product of a systematic effort to ask where smart capital is underrepresented and where a truly zero-to-one founder could build something monopolistic. For founders, the lesson is that if your idea sounds boring or strange to Bay Area investors, that might be a feature, not a bug.On the tactical side of getting a meeting, Josh is refreshingly direct: build a curated list of 20 to 30 VCs from your own research rather than relying on generic investor databases, pursue warm intros almost exclusively, and stay completely away from multi-stage firms for your first round. He explains that with large multi-stage firms, you only get one shot, and you want that shot to be for a $10 to $20 million check, not a $3 million seed. Meanwhile, cold outreach is not dead, but it needs to feel like a real human wrote it. Any email that reads like a mail-merge will get ignored, and novelty plus founder-market fit will always outperform revenue metrics in Josh's inbox.One of the most practically useful threads of the episode is Josh's thinking on cap table dynamics after you close. He warns that the enthusiasm of your investors at the time of the initial wire is typically the highest it will ever be, which means founders need to do the work to build a genuine ongoing relationship through regular updates and honest communication. Going quiet after the raise is a red flag for everyone involved. And for founders lucky enough to be oversubscribed, Josh's advice is to prioritize investors who have strong relationships with the firms you plan to target in your next one to two rounds, treating the current cap table as a strategic lever for future fundraising rather than just a source of cash.

Philip Carson brings a refreshingly contrarian perspective to fundraising from the jump: most startups shouldn't be raising venture capital in the first place. Rather than treating VC as the default path, he pushes founders to honestly assess whether they actually need outside capital or whether they're chasing the idea of being a venture-backed founder. This framing sets the tone for an episode full of honest, un-hype-y advice that's rare to hear from the investor side of the table.One of the most practically useful angles Philip covers is how Cubit actually evaluates founders. He doesn't start with market size slides or traction numbers when reviewing a pitch deck. He's looking for the origin story: did this founder live the problem they're solving? That lived experience, in his view, is a strong predictor of whether someone has the grit to actually build the solution. He pairs this with a somewhat counterintuitive quality he looks for: founders who balance confidence with genuine humility, specifically the kind that makes them coachable without being a pushover.Philip also pulls back the curtain on Cubit's diligence process in a way that's genuinely useful for founders to hear. Their standard process includes a four-hour internal deep dive with a founder call right in the middle of it, followed by in-person visits and customer reference checks before any check is written. He's candid that this process takes weeks, not days, and that timelines vary wildly. His advice to founders navigating the "messy middle" of closing a round is simple but often overlooked: pick investors you actually enjoy talking to, not just the ones with the biggest fund names, because those relationships will outlast almost every other variable.

Arthur's most distinctive contribution in this episode is his "campaign plan" framework, borrowed directly from his Marine Corps background. Rather than just pitching a product vision, he wants founders to show a sequenced, interdependent plan where each milestone unlocks the next. He shares a real example of a three-month-old defense startup that already had a mapped path to their first program of record. For founders, this is a concrete way to stand out: don't just show goals, show the logic chain that connects them.One of the more refreshing moments in this episode is Arthur's take on pitch deck design. He reframes the question entirely, arguing that clarity of thought is what matters, not graphic design. A plain black-and-white deck that clearly answers who, what, where, when, why, and how will outperform a polished but vague one every time. He also pushes back on the obsession with TAM slides, suggesting that the ability to dominate a small, specific market is often a better signal than a flashy market sizing exercise.Arthur closes with two pieces of advice that are easy to overlook. First, treat the fundraising process itself like a campaign, knowing which investors lead vs. follow, where they are in their fund cycle, and timing outreach accordingly. Second, and perhaps most urgently, don't slow down after you close. He argues that post-close momentum is a unique and fleeting asset, and founders who treat closing as a finish line rather than a starting gun are making a costly mistake. He also makes a compelling case for building investor relationships well before you even have a company, noting that a warm intro before founding is worth more than almost anything else.

Brandes brings a refreshingly candid perspective on what early-stage investors actually care about, and it might surprise you. When she opens a pitch deck, she scrolls straight to the team slide and almost nothing else. Not the market size, not the financials, not the roadmap. Just the team. For a fund like Also Capital that writes concentrated inception-stage checks, they are making a bet on a person before there is much else to bet on, and Brandes is clear that this is not just a cliche. She wants to be able to guess roughly what a company does just by reading the backgrounds on that slide.On the fundraising process itself, Brandes drops one of the more honest reframes you will hear: you are never done fundraising. The mindset of "close this round so I can get back to building" is, in her view, a misunderstanding of how early-stage venture works entirely. Fundraising is a game of momentum, and if you stop, you start from scratch. The CEO's job, at its core, is to sell the vision, iterate, and sell it again. If that sounds exhausting to you, she says, it might be worth asking whether the founder path is the right one.She also offers practical advice that does not get talked about enough: founders should be doing reference checks on investors too, not just the other way around. Talk to portfolio founders. Ask VCs how they pitch themselves to their own LPs. Find out who their LPs are. The investor-founder relationship is a 10-year commitment at minimum, and Brandes argues you owe it to yourself to vet that relationship just as rigorously as they are vetting you. That reciprocity, she says, is actually a green flag for funds like Also.

Ethan brings a rare dual lens to this conversation: he spent years as a founder who couldn't get a meeting, then became a managing director at Techstars, where he reviewed thousands of pitches. That combination gives him a clear-eyed view of what actually moves the needle versus what founders obsess over that doesn't matter. His most counterintuitive point: the pitch deck is mostly a red herring. What separates winning rounds from losing ones is process and momentum, not narrative polish. Stacking your investor meetings into a tight three-to-four day window, having your data room ready before anyone asks, and recording customer calls in advance to close the "believability gap" are the kinds of mechanical advantages that compound quickly and that most founders simply don't know to do.Ethan is also unusually direct about what it means to pick your investors well, not just get picked by them. His framework for evaluating funds at the pre-seed and seed level cuts through a lot of brand chasing: unless it is a true tier-one name, the halo effect is minimal, and the more important question is how hard this person is going to work for you. He goes further and pushes founders to ask about fund size alignment early, since a $100M exit is life-changing for a founder but irrelevant to a large fund. That misalignment, he argues, causes more downstream friction than most founders anticipate.On the post-close relationship, Ethan offers something most VCs never say out loud: the most active period of support typically runs 18 to 24 months, and after that, a natural taper is built into the math of portfolio management. His advice is to move to text messaging as quickly as possible to collapse the power dynamic, send investor updates on a consistent clock (because the squeaky wheel genuinely does get more attention), and hold a state-of-the-union call with all investors right after close to reset expectations against what was pitched. Almost no one does any of these things, which is exactly why he recommends them.

Eric brings a refreshingly practical framing to fundraising: it is a process, not a pitch. He emphasizes that founders should treat every phase, from outreach to diligence to closing, as a structured workflow. That means building a list of 50 to 100 firms, drilling down to the right individual at each fund (not just the fund itself), and staying on top of communications with a simple tracking system. He also pulls back the curtain on why VCs pass, and his answer might surprise founders who take rejections personally. Fund deployment cycles, internal team dynamics, and unfamiliarity with a market often have far more to do with a "no" than the quality of the company or founder.One of the more counterintuitive takes Eric shares is around the team slide in a pitch deck. Rather than over-investing in it, he warns that a poorly constructed team slide, packed with advisors who aren't writing checks or can't take a reference call, can actually hurt a founder's chances. His advice is to focus the deck on the problem and the solution, and let everything else be a secondary data point that he can go gather on his own. It is a useful reminder that less can be more when it comes to what you put in front of investors.Eric also makes a strong case that founders should be running their own diligence on investors, not just the other way around. He recommends asking the fund to introduce you to portfolio CEOs, and then specifically seeking out ones who have struggled, not just the success stories. Back-channeling through your own network is equally important. And when it comes to building the cap table, he breaks down the three types of investors worth having: those who provide immediate tactical help, those who bring the right strategic network for later, and the true believers who will grind with you no matter what. His bottom line is that building a cap table deserves the same care and intention as building the product itself.

Adam's biggest throughline is that how a VC behaves during the fundraising process is exactly how they will behave as a partner for the next decade. He is unusually direct about this, encouraging founders to treat the diligence phase as a mutual interview and to do back-channel reference checks on investors just as VCs do on founders. He gives a sharp breakdown of the VC landscape too, suggesting that roughly 20% of VCs are genuinely valuable, 20% are actually harmful to your company, and 60% do little more than write a check. Knowing which bucket your investor falls into before you close is one of the most important decisions a first-time founder can make.On the pitch deck and first meeting front, Adam cuts through a lot of noise. He goes straight to the team slide, not to see a big roster, but to understand whether the people behind the company have the relevant experience and obsession to go the distance. He warns against hiding weak metrics, arguing that VCs will always assume the worst about the numbers you don't show. His advice: own your narrative, get out in front of your objections, and never let a VC discover a weakness before you do.Perhaps the most grounding piece of advice Adam gives is for founders who have just closed their round. He pushes back on the imposter syndrome that causes many founders to avoid asking their investors for help, reminding them that investors want to hear bad news early, there are no dumb questions, and it is the founder's job to put their investors to work. He closes with a candid note that might be the most memorable line of the episode: he would not invest in himself, because great founders are outliers who take moonshots, and that is genuinely rare.

Jakob brings a refreshingly practical, no-nonsense perspective to early-stage investing, shaped by building his own community-based fund in El Segundo, the hardware and defense-tech hub that grew out of SpaceX's roots in LA. Unlike most VCs, Discipulus runs a physical two-week residency that front-loads the relationship-building, network access, and demo day prep that most founders spend 6-12 months scraping together on their own. For founders who are technical, mission-driven, and relatively early in their career, Jakob makes a compelling case that plugging into the right ecosystem early is one of the highest-leverage moves they can make.On the fundraising process itself, Jakob offers a strategy that many first-time founders overlook: start with angels who genuinely like you as a person, use those early commitments to build social proof and momentum, then work your way up to the bigger funds. His reasoning cuts to the heart of how most VCs actually operate: FOMO. He's candid that the majority of pre-seed and seed investors are driven by "if I don't invest today, I'll pay more tomorrow," which means founders need to manufacture real momentum, not fake it.Jakob is also direct about some of the biggest mistakes founders make as they near the finish line: over-representing investor interest, setting fake deadlines they can't enforce, and playing up FOMO in ways that feel manufactured. His advice is straightforward: the hard-tech and defense space is a small, tight-knit world where investors talk constantly, and a bad reputation travels fast. Be kind, be honest, and build real urgency through real progress.

Turner Novak is one of the most unique voices you'll hear in early-stage VC. As a solo GP at Banana Capital writing $100K-$250K checks, he operates more like a founder than a traditional fund partner, and that perspective shapes everything he says. He's built an audience of nearly 200,000 followers across social platforms, and he actively uses that distribution to help portfolio founders get in front of customers, recruits, and co-investors. His advice throughout this episode has a practical, ground-level quality that's rare when VCs talk about fundraising.On the process of getting in the room, Turner is clear-eyed: VCs aren't ignoring cold outreach because they dislike founders, they're ignoring it because they simply can't process everything that comes in. His advice is to stop thinking about warm intros as a "nice to have" and start thinking about them as table stakes. The best intro you can get, he explains, is from a former boss who is already putting their own money into your round and vouching for you personally. Everything else is competing against that benchmark, and founders should build their outreach strategy accordingly.Perhaps the most useful part of the episode comes when Turner breaks down what happens after you think a VC is interested. He's direct about the 1% conversion rate reality, the signals that tell you someone is truly out (like a refusal to book a follow-up call on the spot), and how to keep momentum alive between meetings by sharing real updates rather than vague "just checking in" messages. He also covers what investors actually need to see during diligence, what post-close relationships should realistically look like, and the single biggest mistake founders make after the money hits the bank.

Emily Lindberg brings a genuinely rare perspective to the VC world -- a PhD in biomechanics from UC Berkeley who transitioned into venture through Nucleate, a student-run VC focused on bio companies. That scientific background shapes everything about how Undeterred evaluates deals, and Emily is refreshingly candid about what that means in practice. She emphasizes that even when a fund loves your technology, it has to fit the financial structure of the fund and its return requirements -- a reality many first-time founders overlook entirely.On the question of what gets a founder into the room, Emily reinforces something that often gets lost: cold outreach can genuinely work, but only if it's targeted and concise. Undeterred reviews everything, but founders need to respect how little time is actually spent on each deck. The clarity of your story matters more than polish or design -- and interestingly, Emily notes that a scrappy-looking deck can sometimes work in a founder's favor if it means they've been overlooked by others.Where Emily really shines is in her advice around the later stages of a raise. She pushes founders hard on the idea that choosing an investor is a decade-long partnership, not just a transaction. Optimizing for valuation over fit is one of the most common and costly mistakes she sees. And once the round closes, she flags a pattern she sees repeatedly: founders going heads-down on tech and losing touch with customers -- the very people whose urgency and engagement will determine whether the company survives.

Leo brings a rare combination to the table: technical depth as a mechanical engineer with a PhD from MIT, operator experience as a former founder, and the analytical rigor of a McKinsey diligence background. That blend makes his fundraising advice unusually grounded. Where many investors speak in generalities, Leo is specific. He walks founders through how to build their investor CRM, explaining why identifying who leads versus who follows is the most important filter. He also breaks down what he actually looks at first in a pitch deck, including the ask slide, the why now, unit economics, and team, giving founders a clear hierarchy to design around rather than guessing.One of the more tactical and under-appreciated pieces of advice Leo shares is around calendar density. He argues that talking to too few investors is itself a strategic mistake, not just a numbers game. Without enough conversations happening simultaneously, founders lose negotiating leverage, struggle to build syndicate followers, and can't generate the quiet momentum that nudges VCs to move faster. He also introduces a clever tip around using an FAQ inside a Docsend data room to gauge which VCs are actually doing their homework, a small but revealing signal founders can use to prioritize their time.Leo closes with a sharp framework for the three phases of fundraising: getting the first meeting, moving VCs through diligence, and landing the first term sheet. He is direct that the first term sheet is the domino that makes everything else fall, and that the art of getting it is about subtly conveying momentum, such as mentioning upcoming site visits from other investors, without overselling. For first-time founders who have never navigated that third phase, this episode is one of the clearest explanations of how that game actually works.

Leo brings a rare dual perspective to fundraising advice: he thinks like an engineer and communicates like an investor. One of the most useful threads throughout the episode is his emphasis on respecting a VC's time and attention. With 50 to 100 cold emails landing in his inbox every week, Leo makes it clear that founders who stand out do so not by explaining everything upfront, but by treating their outreach more like a movie trailer than a plot summary. Two or three genuinely compelling data points, delivered concisely, will outperform a five-paragraph essay every time.Leo is also refreshingly honest about what happens during the diligence phase and what kills momentum. His take on chasing disengaged investors is one of the sharpest pieces of advice in the episode: if a VC isn't visibly excited after your first meeting, no amount of follow-up is going to move them into the top 1% of their deal flow. The time you spend trying to convert a skeptic is time you are not spending with someone who is already leaning in. This is a mindset shift many first-time founders need to hear.Finally, Leo makes a strong case for stage-appropriate, seed-specific funds over multi-stage giants when building out a cap table. He backs it up with his own data, noting that at Humba, roughly 65 to 70 percent of portfolio companies graduate to a Series A, but in only about 15 percent of cases does the multi-stage fund that wrote the seed check end up leading that next round. Taking money from a big name fund does not guarantee easier future fundraising, and if that fund passes on your A, it can actively hurt you by sending a bad signal to the market.

Mike Steadman is not your typical VC. A former Marine infantry officer, three-time national boxing champion, and self-described "underdog and misfit," Mike came up through bootstrapping businesses before landing at Context VC as a venture partner -- a path that gives him a sharp eye for what separates founders who get funded from those who don't. His advice throughout this episode is grounded, tactical, and refreshingly honest.What makes this episode worth your time is how Mike frames fundraising as a second product that founders have to build and sell in parallel with their actual business -- and most founders are wildly underprepared for it. He walks through everything from how to build a hyper-targeted VC list using your "unfair advantages," to why your LinkedIn profile matters more than your pitch deck at the pre-seed stage, to how to behave in a GP meeting when a term sheet offer might land in real time. He also doesn't shy away from the harder truths: that you need to be talking to far more investors than you think, that warm reputation checks are a real part of diligence, and that closing the round is just the start of the hard work.

Jesse brings a rare dual perspective to this episode. Having built and sold his own company before becoming a VC, he speaks to founders as someone who has genuinely sat on both sides of the table. One of the most refreshing threads throughout the conversation is his honesty about what VCs actually go off of at the pre-seed stage: almost nothing. With data rooms described as "ghost towns," Jesse explains that social proof and momentum matter disproportionately, not because VCs are lazy, but because there is simply very little else to evaluate. This reframes the fundraising process less as a merit contest and more as a momentum-building exercise, with strategic meeting sequencing playing a bigger role than most founders realize.Jesse also gives unusually direct feedback on pitch decks, pushing back on some of the most common slides founders spend hours perfecting. The TAM/SAM/SOM slide, the hockey stick revenue projection, and the bloated advisory board are all called out as doing more harm than good in most cases. Instead, he wants to see a team slide with punchy, concrete achievements, early evidence of traction, and a go-to-market rooted in a specific ICP rather than a list of channels. His two-by-two framework of "conviction versus coachability" is a memorable and genuinely useful lens for founders thinking about how they come across in that critical first meeting.Perhaps the most underrated part of this episode is Jesse's advice on what to look for in a VC. He pushes founders hard to actually interview their investors, asking about reserve strategy, deployment cycle, and how they show up when things go sideways. He also makes a pointed case for matching fund size to your ambitions, noting that smaller funds have many more "paths to victory" and can generate strong returns without needing a unicorn outcome from every bet. For first-time founders who default to chasing the biggest name brand funds, this is a perspective worth sitting with.