Rishabh Surendran | Gaingels

Rishabh Surendran | Gaingels

Rishabh is a pre-seed deep tech and frontier specialist at Gaingels, a 12-year-old venture syndicate that does not lead rounds. Instead it co-invests behind a lead at roughly 10% of the round (typically 250K and up at pre-seed and seed). His background is atypical for a VC: engineer trained in India, a stint at Goldman, deploying deep tech for the Indian government in remote terrain, then an internship at Draper pitching deals directly to Tim Draper before landing at Gaingels. Because his fund follows rather than leads and writes smaller checks, his view of what a founder should want from an early investor is different from the default partner-at-a-lead-fund perspective. His sharpest contrarian point is to stop obsessing over GPs and partners. The associates, senior associates, and principals actually run deal flow and respond faster, so win them and the partner conversation follows. He also argues founders wrongly write off a non-lead because it cannot cut a big check. He frames his own value as connective, making warm intros to leads he knows from Draper and elsewhere, and says that in one recent four-month stretch intros he sent by email led to over a million dollars of investment across a couple of companies (he cites checks around 750K and 350K). For cold outreach he wants the opposite of mystery: one or two plain sentences on what you build, what's next, and how much you're raising. Cryptic "cursor for defense" style one-liners are a turn-off for him. On the round itself he leans hard on transparency, because investors verify with each other. He recounts a founder who claimed a soft commit from Draper that Draper flatly denied, which cost the founder both relationships. He warns against the oversubscription trap, where a planned 2M round creeps to 3.5M and over-dilutes because saying no to money feels wrong, and against valuations with no math behind them (the "next Nvidia" claim with no TAM logic), which scare off early investors. On the deck he wants a real team slide rather than just the founder's blurb, plus one clear product slide and a short five-slide send-ahead version. And he prefers first calls that open as a conversation, with slides shared only about 15 minutes in, when the technology genuinely needs them.

Jake Storm | Felicis

Jake Storm came to venture through an unusual route: enterprise software sales at Qualtrics and Zuora, then investment banking (including working on Zuora's IPO), before Felicis. That background shapes how he thinks about founder outreach, pitch construction, and the investor relationship in ways that are meaningfully different from investors who came up purely through finance or pure operating. He treats both cold outreach and pitch structure through a sales lens, and he's skeptical of the academic approach most founders take to both. The most actionable part of the episode is Storm's framework for what he actually evaluates in a pitch. He argues that founders over-index on TAM slides, which he calls "a rudimentary approach to articulating why there will be market pull." What Felicis actually wants to see is a sharp "Why Now" construction: evidence that this is the right moment, that the founder has seen something the market hasn't yet, and that they can show it clearly within the first few minutes of a meeting. His test is blunt: if 15 to 20 minutes into a first meeting the unique insight still hasn't surfaced, it is very hard to recover. Storm also makes a pointed case for tiering your investor list by individual partner fit, not fund brand, and spending time proportionally rather than treating every name on your CRM as equally worth pursuing. One of the more useful tactical pieces Storm offers is a question he tells founders to ask investors directly: how many of the founders you work with are pinned at the top of your messaging apps? It's a simple proxy for how actively a VC actually works with their portfolio, and it reframes the pitch dynamic in a way founders often don't consider. He also makes a distinction between "conviction investors" (funds that move on their own belief) and those waiting for a signal from another investor before committing, and says founders would do well to understand which type they're talking to before investing heavily in a relationship. On post-close mistakes, his view is clear: the most common failure is over-optimizing for investor feedback during fundraising and losing the customer-obsession that should be driving the company.

Kenan Saleh | Andreessen Horowitz

Kenan brings a perspective that's rare even among founder-turned-investors: he's sitting inside one of the most visible early-stage programs in venture (Speedrun sees 20,000+ applications per cohort) while being only about six months into his role at a16z. That freshness means his advice isn't abstract or ten years removed from the founder experience. He sold his first company, Halo, to Lyft, got exposed to a16z through Ben Horowitz's board seat, and went back to building before eventually crossing over to the investor side. His advice is practical and grounded in what he's watching founders do right now, in real time, through the Speedrun program. One of the most counterintuitive takeaways from this conversation is Kenan's stance on pitch decks. He argues that most investors barely look at the deck before a first meeting. They're scanning the email blurb, clicking through to your LinkedIn, and making a snap judgment on whether the team and category are interesting enough to warrant a conversation. Founders, he says, should be spending far more time on how they present themselves online and how they tell their story in the room than on making a beautiful 30-slide deck. He even suggests that the best first meetings often don't use a deck at all, favoring a more conversational dynamic where the investor can ask questions and the founder can demonstrate depth and conviction in real time. The other standout advice is around process discipline. Kenan recommends founders build investor lists of 100 to 200 funds (not the 20-30 most founders default to), and he references Vinod Khosla's point that time spent preparing for a fundraise may be more important than the fundraise itself. He also has a clear framework for handling oversubscription: rather than running a bidding war on price, he advises founders to identify the best long-term partner and then ask that partner to match competing offers. It's a less adversarial approach that he believes leads to better outcomes for the company over the long run.

Zal Bilimoria | Refactor Capital

Zal isn't your average seed investor. He's the solo GP behind Refactor Capital, a hard tech seed fund based in Burlingame, and he just closed his fifth $50M fund. Before going solo, he spent a decade in product at Google, Netflix, and LinkedIn, then jumped to A16Z where he helped launch the Bio Fund. Today, he writes $1-2M checks into energy, aerospace, robotics, bio, and health. The cap tables he sits on read like a hard tech hall of fame: Solugen, Astranis, Orchid Health, YourChoice Therapeutics, Vitra Labs. And every founder he backs gets free mental health therapy through Lyra Health, on his dime. Not many seed funds do that. The first half of the episode is a masterclass in cold outreach and first meetings. Zal's mental model for a fundable founder is sharp: they need to be "magnets for customers, talent, and investors," which means being both technically and commercially gifted, and a great storyteller. He breaks down his "test pitch" approach (start with 5-10 friendly VCs before expanding to 50+), why he reads every deck on his phone (and decides in 30 to 60 seconds), and the specific tells that lose him in pitches: reading off the screen, low energy, no homework on him as an investor. He's also refreshingly direct on decks: 10 slides max for a teaser, use Claude to design it for $10 in tokens, and stop spending $50K on deck designers. Where the episode really pays off is the back half on round construction and post-close mistakes. Zal lays out his "airport layover test" for picking investors, argues hard against optimizing for the highest valuation, and explains why a "village" cap table beats a single lead. He's also blunt about the post-close trap first-time founders fall into: a six-month hiring crawl driven by second-guessing, when the real test is one or two days in office with the candidate. And he closes with what may be the most actionable advice in the episode for hard tech founders: the fastest way to make your next round easier is to get a third party (LOI, pilot, paid contract) to validate your tech so the next VC doesn't have to do de novo diligence.

Mat Vogels | Harpoon Ventures

This is the role-reversal episode where Mat steps out from behind the host mic and gets grilled by Ali Rohde about his own playbook. Mat invests at Harpoon Ventures (deep tech, $1M to $5M checks) and runs Black Flag, Harpoon's pre-accelerator that often writes the very first check into companies before they've even incorporated. He came up as a YC founder (Zestful, killed by COVID), pivoted into VC via Julian Shapiro, and treats VC itself like a product, building tools like VC Sheet and pitchrec.com [http://pitchrec.com] to make the fundraising process less opaque for first-time founders. He's bullish on cold email in a world where everyone else worships warm intros, sharing the story of how he raised his first check with an all-emoji email to Shrug Capital. He thinks pitch decks are quietly dying because firms like Harpoon now run every incoming deck through AI before a human ever opens it. And he's brutal about what he's actually looking for in the first meeting: not your idea (he's seen a dozen versions of it, including the ones you think are unique), but whether you have the energy and depth to go a thousand miles deep on this for the next decade. On closing, he lays out the most honest cap table framework I've heard in a while: roughly 60% of VCs are net zero on your company, 25 to 30% are net negative, and only 10% are net positive. The goal isn't to chase the positives, it's to avoid the negatives. He also breaks down a "wave approach" to building real FOMO without lying, and offers a counterintuitive post-raise warning: today's bigger mistake isn't spending too much, it's still acting frugal when you've raised real money and need to deploy it fast.