Fun Raising

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.