5 days ago

Michael Gibson | 1517

Michael Gibson likes to say he has no business being in this business. He was working on a doctorate at Oxford in moral and ancient philosophy, following a T.S. Eliot-shaped plan to be a professor who wrote on the side, then dropped out, took a job at MIT's Technology Review, and on his first day working with Peter Thiel got pulled into announcing the Thiel Fellowship. He and co-founder Danielle Strachman ran that program for nearly five years: apply at 19 and under, and drop out of college if you were enrolled. Ethereum, Figma, and later Anthropic co-founder Chris Olah came out of those years. They named 1517 after the Protestant Reformation because they think the diploma is the modern indulgence — Yale or fail — and something like 90% of their investments have at least one founder without a degree. They are a pre-seed firm that likes being first money in, writing about a $100K check when a short experiment will prove a concept and about a million when there is a team and a plan. The part founders can actually use is how he runs a first meeting. It is not a yes or no on the check. It is whether they want to go deeper. What he is listening for is a trait he calls hyperfluency: speaking forwards and backwards about the industry, why past efforts failed, why this attempt will work, then scaffolding the same explanation up to an expert and down to "the dumb Labradors." Danielle calls the other tell dog-fighting-to-get-off-a-leash energy; they want to feel urgency, and they want to be the ones who snap the leash. Do the homework. He asked a founder last week if anyone on the team had a degree, heard that everyone was getting one and thought that mattered, and asked whether the kid had even seen 1517's website. Keep the deck to company, problem, solution, and team, 15 to 20 slides, and skip the AI-polished fake-personal email. If they go deeper, more of the team plus a subject-matter expert joins, they use SAFEs, and the process is supposed to take two weeks with a clear answer. He thinks founders should ask other investors the same questions — what is your process, what is your timeline — because too many firms stay secretive while they kick the can or wait for someone else to lead. The warning is that you cannot fake the first yes. The first commitment is always the hardest, and psychological FOMO will not manufacture it; if the tell that you are manipulating someone is too strong, it is a turnoff. One team told him they were using Robert Greene's laws of power on another investor. His reaction: are you stupid? Send weekly or biweekly updates instead, including who is actually in, and only get more direct with people who are leaning yes as a real close approaches. After the round, treat check-ins like mock board meetings and do not hide what is not working. Startups, he says, are the great revealer. You will have hard conversations every day, you will be wrong every day, and the one thing you cannot do is ignore the weaknesses they expose — shore them up or delegate, or you fail.

3 Sept

Ian Rountree | Cantos

Ian came up as an operator first. He joined SoFi at about 25 people, then became founding chief of staff at Invisible Technologies, where he and the CEO pitched roughly 100 investors, took 99 nos, and got one angel yes. Only four or five of those conversations felt useful. That knocked VCs off a pedestal and sent him into a year and a half of raising Cantos I. He started the firm when hardware and the real world were uncool, against a mentor who treated the idea like a slap. Now investing out of Fund IV with partner Grant as a first-check GP, he lets entrepreneurs tell him where the future is going. At idea stage he underwrites the people, not the industry, model, or go-to-market on the deck. The tactical spine is that the warm network is the real inbound. Ian has only ever invested in one cold inbound, so a trusted founder calling someone special beats any deck. X is how you warm a cold DM: lurk, post, and show up already known. When a deck does land, he reads it backwards, Tom Perkins style, then tabs to the team page first and texts mutuals. First calls are booked at 30 minutes but they block 90. Internally they score founders on six attributes he will not name, then test for a gravity-well vision. If you want a $10 billion company in 10 years, you are creating something like $20 million of value a week, and the world has to warp around you. Intellectual answers are table stakes. After the call he wants to feel fired up enough to run through a brick wall. The warnings are as specific as the screen. Do not pitch a second idea when they pass. It reads like a trinket salesman opening the coat. If the call is asymptoting to no, end it. Do not lie, fake FOMO, or write a tier-one name on the whiteboard and pretend you forgot the last meeting. Ask for portfolio references only after they have asked to invest, and include a company that failed. When you have a choice, pick the board you can live with for twenty years over the highest valuation. After close, hiring is the work. Use the 409A strike-price window sparingly for one key hire, then run an investor onboarding session so they get put to work. Fundraising is a numbers game. When Ian complained to an entrepreneur about 100 LP meetings, the reply was, my man, you're just getting warmed up.

1 Sept

Taylor Sargent | Industrious Ventures

Taylor did not come to venture through a typical banker or operator path. Space was the through-line: physics undergrad, aerospace and defense consulting on NASA Goddard ground-station work, time with the Defense Threat Reduction Agency, then two and a half years at DARPA headquarters helping deploy nearly $150 million across advanced technologies. When he left government, he chased the role that felt most like DARPA without being government-facing, and that landed him in deep tech VC. At Industrious he brings that buyer-side lens to early companies chasing non-dilutive paths, while the fund's genesis in industrial-company relationships (and a model that flips the usual check-size curve toward heavy follow-on) gives later-stage founders a different kind of leverage. One unusual detail: when Industrious takes a board seat, they do not park a partner in it. They recruit industry operators who are better suited to advise the company than anyone inside the fund. The tactical spine of the episode is how to get into a sector-focused inbox without sounding like a blast. Taylor's filter is blunt: if you can swap his name and fund for another pair and the email still reads the same, he will almost certainly skip it. Specific alignment to his background or the portfolio, on the other hand, routinely clears his first-call bar - cold or warm. Once in the room, he is listening for two things: an element of uniqueness he has not already seen a dozen times in the category, and whether at least one core pillar of company-building (tech, government sales, industry relationships, or deep domain fluency) is already covered, with honest awareness of the gaps.Diligence often includes the fund's outside advisors and, when founders allow it, quiet industry feedback from relationships Industrious was literally founded around - without treating a "no" on sharing materials as a deal-killer. The sharper warnings are cultural as much as tactical. Early venting about how miserable fundraising is can be hard to look past when many more rounds still sit ahead; capital-intensive companies need fundraising resilience, not just product resilience. Equally counterintuitive for technical founders: the under-promise, over-deliver instinct that wins in the lab is often a liability when a round is pricing in growth. After the close, going dark until the next raise is one of the fastest ways to forfeit follow-on from a fund that invests by following the story. Taylor's closing frame is simple and hard: companies sometimes talk to hundreds of investors before a lead term sheet lands - it takes one, and when the process feels senseless, you have to be soldiers and keep marching.

20 Aug

Patty Wexler | Avila VC

Patty Wexler is not a default VC. She spent the first half of her career funding consumer internet at a $1.9B firm, then made a deliberate bet around 2015 that "so much IQ and so much capital in this little zip code" could not keep chasing the same three ideas. She now invests out of a small fund one at seed to A, across nuclear fusion, industrial automation software, magnesium, and drilling tech. That combination, a consumer-software pedigree plus an engineer's bias toward the physical world, is why her advice skips the usual talking points. Her most useful reframe is about the power dynamic in a first meeting. Founders walk in braced for a skeptical loan officer; Wexler says the opposite is true, that she is hoping to be sold and is leaning in. The practical version of that is calibrating your pitch to what the investor already knows. If you are solving nuclear energy, do not spend a slide on how big the energy market is, because everyone gets it. Save the TAM case for markets she cannot size in her head, and if you are one of a thousand teams building the same agentic tool, spend that time on why you specifically. Her read on VC attention is blunt: it is drifting toward "fruit fly level," so lead with the hook and elaborate later. A related prep tactic is to run a search on yourself before pitching, the way you would before a date, and assume any lazy investor will spend one minute doing the same. On process, she sets expectations founders rarely hear stated plainly. Investors are "an inch deep, a mile wide," so expect lateral insight and warm intros, not domain depth you already own. Her diligence ranges from a single weekend when she knows the founder and space to six or eight weeks to a term sheet plus a couple more months to close the syndicate when she is leading cold. The most actionable framework is how to sequence the raise: do a few test runs with firms that are good but not your first choice, then concentrate on your target firms, then work the rest, so a middling firm is not deep in your process when your dream firm finally engages. She also normalizes the quick no (nobody holds a grudge over a fast, clean pass) and the reminder that you are always fundraising, so you should not wake up six months from cash-out and start cold.

13 Aug

Arkady Kulik | Arkane

Arkady is a scientist and repeat founder who moved into venture specifically to solve a translation problem he kept watching play out: deeply technical founders who can't tell their story, meeting VCs who can't tell whether the science is real or "Theranos 2.0." That background shapes a fund that behaves differently from a default seed check. He leads first rounds, wants to be the first VC on the cap table, and screens on two questions only when he opens a deck: what have these founders understood that nobody else has, and what problem space are they in. Everything else is secondary. The tactical advice is where the episode earns its time. On outreach, he wants founders to build three or four tiers and start with a "tier zero" of friendly VCs they don't even need, purely to rehearse the pitch and burn through the rough reps before approaching the firms they actually want. On decks, he argues the competition slide is close to useless at pre-seed, because any static two-by-two is a snapshot of a moving target, and early companies die from execution, not from competitors. On process, he time-boxes hard: a non-fit founder is out inside 30 minutes, and even a serious diligence path costs no more than three and a half hours of the founder's time, run through a questionnaire, a scientific partner, and a business partner before a final call. He treats a slow, ambiguous process from other VCs as usually a soft no, not a maybe. His most contrarian material is about the money itself. He ranks capital plainly: revenue first, debt second, equity last, and calls equity the worst money a founder can raise because it loads on the most liability and the most outside expectations. He refuses to celebrate a close, and warns against "suicide rounds," raising too much at too high a valuation too early, then spending like the cash will never run out. His fix is unglamorous: park it in treasuries and behave as if you never raised. He's equally direct that manufactured FOMO is an instant pass, since reputation in this market dies in hours, and that most failures trace back to execution and founder psychology rather than the balance sheet.

6 Aug

Matt Logan | Earthshot Ventures

Matt Logan is a GP at Earthshot Ventures, a climate fund spun out of the nonprofit Elemental. What separates him from a default climate investor is that he doesn't lead with decarbonization. He looks for companies that win because they are cheaper, better, or faster, with the climate benefit as a byproduct of the core value prop rather than the pitch itself. His thesis, the clean intelligence stack, runs the length of the AI supply chain, from critical minerals up through data center energy, compute efficiency, AI-native applications, and physical AI, which is where he expects most of the next decade's power-law outcomes to sit. The most useful thing for a founder is his honesty about sourcing. Of seventeen investments in fund one, nine came from his own cold outbound and eight from his network. None came from a founder's cold email. His takeaway is not that founders should stop trying, but that the leverage is in becoming someone worth reaching out to: early traction, a strong team, and small checks from smart angels in your market who can refer you (he'll take a meeting off a $1K check from someone sharp). He also frames access as "legibility." The less legible you are to capital, the more you should target firms that specialize in your exact stage and sector instead of chasing multistage brand names. In meetings he weights founder intensity, clarity on business model, and unit economics above a deep technology walkthrough, and he would rather a founder name a weak unit economic openly than leave it as the elephant in the room. Two closing tips stand out. First, diligence the investor by talking not only to the references they hand you but to the founders of their portfolio companies that went under, because that is where you learn how a VC behaves when things go badly. Second, keep terms clean (standard YC SAFE docs), optimize for complementary skill sets over valuation, and remember that stated numbers are often flexible once a VC has gotten to yes. And if you are struggling to raise, his advice is blunt: go back and build, because traction relative to your resources, the inflection rather than the absolute number, is what unlocks a round. Product market fit, as he puts it, covers over almost any other sin.

4 Aug

Sarah Kunst | Cleo Capital

Sarah Kunst is a sole GP who has been on both sides of the table: operator roles at companies like Chanel, Red Bull, and Apple, a founder whose own startup wound down, and a Sequoia scout before raising a roughly $3M first fund in 2018. That combination shows up in how she sources. She invests pre-seed through Series B, and unusually says she prefers the two ends (pre-seed and Series B) over seed and A, because seed and A often mean paying a markup for someone else's de-risking, and "you can only lose your money once." She also frames her sector interests as a map of her own anxieties: consumer cybersecurity, next-gen fertilizer, and next-gen energy. Her most useful contrarian take is on access. Most guests tell founders to chase warm intros; Kunst says that at the earliest stage that hunt is "so silly," because no third party can move her to write a million-dollar check. She treats sourcing as a shots-on-goal, top-of-funnel game, and backs it up with volume: she claims to have read every YC and Techstars deck since roughly 2020 and over 10,000 inbound pitches through her site, which she reads personally on weekends. The counterintuitive part is what that inbound feeds into. She takes almost no meetings, and says her meeting-to-investment conversion is high precisely because she meets so rarely. In a typical week she'll read 300 pitches and take zero meetings. So the leverage for a founder is in the written materials, not in landing time on her calendar: a teaser deck (she points to Guy Kawasaki's 10-slide format), a clear path from a multi-billion-dollar market to real revenue, relevant comps, and enough narrative control that she doesn't wander off and form her own wrong opinion. On judgment calls, she is specific. Optimizing for the highest valuation over the best terms is a vanity move, and clean, standard docs (Cooley GO, YC boilerplate) protect you no matter who ends up holding the paper after you sign. On the cap table, redundancy beats prestige: ten Silicon Valley CTOs who all know each other give you one network, not ten, so trade some of them for a differentiated skill set or geography. On founders themselves, she is wary of the "MBA in search of a problem" and weighs three kinds of relevant experience (lived, educational, work). Her recurring red flag is rigidity: founders who can't talk through a plan B when a dependency breaks, what she calls the "airport problem." And her blunt filter for whether someone should start at all: if the goal is just money, the odds are better in prediction markets, so you have to actually love the process.

30 Jul

Jason Gray | Pioneer Fund

Jason is an operator before he was an investor. He ran a division at SunEdison up to roughly $250M in revenue, went through YC in 2015 as a founder, and built Pioneer Fund out of the alumni network he kept gravitating back to. The structural difference from a default seed fund is the 500 YC alumni who serve as venture partners and LPs. When Pioneer takes an investment call, Jason pulls in three or four of them who are operators in that exact space, so diligence on "is this team actually moving fast" comes from people calibrated to that domain rather than from a generalist partner. He frames the whole firm as the process he wished he'd had as a founder. The most actionable material is about running the process, not selling the story. Pioneer commits to a decision within 48 hours, usually 24, tells founders upfront who will be on the call and when they'll hear back, and treats a second meeting as evidence its own process failed. Jason is openly anti-deck: the deck's only job is to win the meeting, and once you're in the room he wants it put away so you can actually talk. On outreach, he cites the YC line that conciseness correlates with how well you understand your own business, and prefers a tight email with the unique insight and traction over a half-memo. On constructing the round, he lays out three buckets (strategic angels, smaller or emerging funds, and big funds) and makes the case that small "base hit" checks of $50K to $200K compound into the momentum that forces fence-sitters to move. The counterintuitive takes are where founders should lean in. He warns hard against manufacturing fake FOMO, because his side has run the pattern hundreds of times and the founder's dataset is a single fundraise. When you do have options, he says carve out a day or two, decide, and execute, because flailing costs you allocation when handshakes elsewhere expire. He tells founders to back-channel the specific partner, not just the firm, especially with mega-funds where pre-seed and seed attention is thin. And on why companies die, he puts co-founder misalignment and treating raised capital like revenue well ahead of competition. None of this is generic "build a great product" advice; it's a working investor describing his own mechanics.

Fun Raising

Michael Gibson | 1517

Ian Rountree | Cantos

Taylor Sargent | Industrious Ventures

Patty Wexler | Avila VC

Arkady Kulik | Arkane

Matt Logan | Earthshot Ventures

Sarah Kunst | Cleo Capital

Jason Gray | Pioneer Fund

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Fun Raising

Episodes

Michael Gibson | 1517

Ian Rountree | Cantos

Taylor Sargent | Industrious Ventures

Patty Wexler | Avila VC

Arkady Kulik | Arkane

Matt Logan | Earthshot Ventures

Sarah Kunst | Cleo Capital

Jason Gray | Pioneer Fund

About

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