New to Venture

“This is the last time you’re going to see me graduate” Molly Cantillon stated these words to her parents at her HIGH SCHOOL graduation. They weren’t amused…Years later, she dropped out of Stanford, moved into a hacker house (sharing just a mattress topper), and raised money from OpenAI.I sat down with Molly, founder of NOX, a company rethinking how humans communicate in this AI-native world. Despite being the youngest guest on my podcast, she’s got the most confidence. If you’ve ever wondered what conviction looks like in Gen Z form, this one’s worth your time.Here’s what I learned:1️⃣ Conviction beats credentials: Molly dropped out of Stanford not because she had a perfect plan, but because she had an unshakeable belief that AI was creating a once-in-a-lifetime opportunity. When ChatGPT hit, she saw it as "a complete level playing field" where time spent with the models mattered more than pedigree.2️⃣ Hire for whimsy, not resumes: Molly's first hire was a 17-year-old from Canada she found in Discord communities. She looks for people who do have a deep love for technology, which is usually evident in their early years. 3️⃣ Delayed gratification reveals character: Molly and her team share a love for running. It's not a hiring test, it's a shared value. People who can work through difficulty knowing there's something great at the end naturally gravitate toward each other. Those painfully long runs become the perfect metaphor for the startup grind.Timestamps:(00:00) - Introductions(01:08) - Dropping out of Stanford(09:48) - Molly’s first fundraise(16:30) - NOX’s many iterations(24:23) - PLG + the current and future state of communication(33:45) - Growing the team and culture(38:42) - Love for technology + delayed gratification(42:53) - Highlights(44:25) - Ceremonial Final Qs

Where do VCs get money from?Welcome to LP land. The mysterious world where people who fund VCs live. Nate Leung, Partner at Sapphire Partners and Co-Founder of OpenLP, gives us a peek into the backbone of the venture ecosystem, and it’s wilder than you think…Episode 049 is live.Here’s what I learned:1️⃣ Great investors ≠ Great fund managers. You can pick winners all day. But if you can’t deliver trust, consistency, and a narrative LPs can sell internally, you won’t survive as a fund manager.2️⃣ GP-LP fit matters. LPs represent causes, initiatives, and interests. These relationships last decades. Partner with the organizations you’re aligned with.3️⃣ Every LP has different incentives. Some allocators want access to innovation. Some want brand and prestige. Some would rather be safely wrong than boldly right. Work with people who are structurally incentivized to want your success. Ask yourself, how are folks on the LP side compensated?4️⃣ Investment decisions are often team sports. You may write the best memo in the world, but without trust and credibility, you won’t get far. Circulate opportunities and gauge appetite before decision time.Timestamps:(00:00) - Introductions(01:30) - Sci-fi novels + being a parent + time travel(07:08) - Origin stories(09:18) - Great investors vs. great fund managers(12:03) - GP-LP fit(16:03) - LP incentive structures + signaling(18:41) - Liquidity and secondaries(21:21) - Why is LP land so mysterious?(22:53) - CalSTRS + conflict of interest (28:02) - Portfolio construction(29:43) - GPs switching strategies(31:08) - Are platform teams actually valuable?(33:30) - Raising Fund I from track record and references(34:00) - Pools of capital still investing in <$50M funds(35:20) - Who/what decides fund size?(38:05) - “Value-add” LPs(39:26) - What is the biggest compliment an LP can receive?(41:02) - What’s something you learned the hard way?(44:04) - Ceremonial Final Qs

VC is a young person’s game.More time. More energy. Stronger pulse on what’s next. It’s one of the few industries where being young is actually your edge.But here’s what most young VCs get wrong: They try to think like their partners instead of developing their own taste.Chauncey Kerr Hamilton, Partner at XYZ Venture Capital, breaks it all down in episode 048 of New to Venture.Here’s what I learned:1️⃣ Time management is everything. If you like poker, host a poker night for your founder friends. If you have kids, take them on your work trip. Feed two birds with one scone. Blend personal and professional. It’s the only way to survive.2️⃣ Your job as a young VC? Understand what your firm wants AND figure out your own taste in founders/companies, then find a way to marry them together.3️⃣ Get good at explaining why you’re excited. You’ll need to convince committees, later-stage investors, and LPs. If you can’t articulate your conviction, you won’t close the deal.4️⃣ Do post-mortems on failed deals. What went wrong? What did you miss? Your blind spots will haunt you if you don’t find them early. 5️⃣ Winning deals gets easier over time. More people in your corner = more references. Chauncey’s formula: Unvarnished feedback + unwavering support + speed to conviction. Speed IS support.6️⃣ VCs will never know more than founders about their space. But they know the venture game. What gets funded? What do growth investors look for? What’s changing? A great investor should provide a birds eye view of the startup ecosystem. Young VCs have the time, energy, and ability to relate to young founders. Use that to your advantage.Episode 048 is live. Time to level up.Timestamps:(00:00) - Introductions(01:03) - Chauncey’s path to venture(04:02) - The Chief of Staff role(05:26) - Gardening! + Parallels between life and investing(09:42) - Time management(11:53) - What changes with tenure?(15:00) - Developing your taste in companies(17:35) - Missing out + winning deals(21:37) - Treating founders well(24:30) - How Chauncey wins + Providing value(27:42) - Consensus thinking(30:52) - Mentoring(36:43) - Highlights and lowlights(40:42) - Ceremonial Final Qs

My first in-person podcast. Ever. I kept thinking about it. A LinkedIn lurker who’d never posted. A kid with a computer and too many questions about venture.Now I’m sitting across from Bryan Kim at a16z. Real conversation. Real energy. Pinch-me moment.Bryan’s invested in companies that became the fabric of our society. Partiful, how we gather. Cluely, the AI assistant everyone’s talking about. ElevenLabs, the voice of AI. BeReal, the most authentic social media platform. Tune in to hear how he did it.My key takeaways:1️⃣ In a world where AI models are changing constantly, momentum becomes the moat. Momentum = Shipping velocity + distribution. 2️⃣ Super apps haven’t been built yet because they need their core competency to be at ~99% adoption first. Messaging, payments, and social media are all too fragmented.3️⃣ Know your zone of competence. Own what you crush at, but also own what you suck at. It’s okay to not be good at everything.4️⃣ Almost everyone in venture comes from somewhere impressive. Stanford, Goldman, Mckinsey, ex-founder. So what? Be a beginner. Nothing is beneath you. Do the work and soak everything up.5️⃣ Your partners won’t always agree. If you think you know something and have done the work, have conviction. That’s why you have a seat at the table!47 episodes ago, I started with a question. Today, I’m getting answers from the people shaping our future. Sometimes you just gotta start.Timestamps:(00:00) - Introductions(01:06) - The power of “Where are you from?”(02:11) - Origin stories(03:56) - Korean venture capital + Super Apps(08:57) - Momentum is the moat(13:49) - High quality distribution(17:23) - Creating momentum(24:15) - Bryan’s zone of competence(27:46) - Highlights and lowlights(35:13) - Ceremonial Final Qs

“If you have to ask someone to be your mentor, they are not your mentor.”Meet Grace, a partner at Amplify Partners and the person that dropped that massive truth bomb. In our conversation, Grace didn’t hold back. And honestly? The VC industry needs more people willing to say the hard thing. Here are some of my favorites:1️⃣ Work-life balance in VC? No shot. To compete against the best investors, the game demands everything.2️⃣ Young VCs need exposure, not expertise: Hear 1000 pitches. Meet 1000 founders. Taste and intuition comes from volume.3️⃣ Belief compounds: ”Having someone tell you that you’re amazing 1000 times changes everything.” We drastically underestimate the compounding effect of belief. One person’s consistent faith can reshape an entire career.4️⃣ The VC investor mindset: “I don’t think to win, I think to help." The best investors don’t keep score with founders. They aim to create value and showcase their loyalty.5️⃣ The generalist VC is dying: Watch the exodus happening right now. Partners leaving mega-funds to build specialized, artisanal firms. The future belongs to those who pick a lane and own it.What broke my brain? Venture Capital is fundamentally a series of transactions. Buy equity. Sell equity. Repeat.But here’s the paradox that Grace helped me see: The LEAST transactional VCs build the BEST portfolios.Why? Because helping without keeping score creates trust. Trust compounds. In a game built on reputation and relationships, trust is the ultimate currency. Grace's Spotify playlist: Raving 101 - there is more to love than GenAI Timestamps:(00:00) - Introductions (01:58) - EDM & traveling(06:42) - Grace’s new show: Get with it(08:40) - Work-life balance and Grace’s outlook on venture friends(10:23) - Grace’s career arc + mentorship(17:06) - Specializing and being a technical investor(21:38) - Menlo Ventures → Amplify Partners(24:24) - Current state of venture(30:06) - Grace’s mindset!(32:07) - Highlights and lowlights (34:33) - Ceremonial Final QsSubscribe on YoutubeFollow on SpotifyFollow on Apple PodcastsFollow Taiki on LinkedIn

When everyone said it was too early to invest, Manu Kumar, founder of K9 Ventures and HiHello, said it was too late. Meet the man who coined the phrase “Pre-seed.”In 2008, Manu Kumar saw something others missed. While VCs were waiting for traction, the best founders were building in garages with credit cards. So he coined a term that would reshape how we think about early-stage investing: Pre-Seed.In episode 045 of New to Venture, Manu and I dive deep into what it really takes to spot greatness before anyone else does. From his time building companies to investing at the earliest stages, his insights hit different. This conversation challenged everything I thought I knew about venture. The truth that stuck with me? “You cannot be in venture without having lowlights. The successes get amplified and the failures get swept under the rug.”My key takeaways:1️⃣ You never really learn to be a CEO. Every company and every problem is unbelievably nuanced. There’s no playbook, no shortcut. Each journey demands its own map.2️⃣ Hire only when you’re hurting: Never hire in anticipation, wait until you feel the pain. Be slow to hire, fast to fire. Working with someone reveals more than any interview ever could. Implement trial periods during your hiring process.3️⃣ Grit beats everything: Manu looks for “insane perseverance in the face of complete resistance.” Companies don’t fail because of competition or markets, they fail when founders give up.4️⃣ Incubate, then trust your gut: Taking breaks from problems lets your brain solve them subconsciously. New information may sway your perspective, but hone your relationship between instinct and action. 5️⃣ Clear commands win wars: “If you’re commanding an army, you have to give clear directions.” Being a founder is about guiding people toward a shared mission. Ambiguity kills momentum. 6️⃣ Find your investor - strategy fit:No VC strategy is inherently right or wrong. It just has to align with who you are. Manu does high-conviction, concentrated bets on people. What type of risks excite YOU?7️⃣ Job titles shape behavior: Give someone a title, they’ll do what that title entails, not whatever the company needs. Be intentional about how you label roles. 8️⃣ Same problems, different scale: Companies of vastly different sizes often face identical challenges. The scale changes, but the fundamentals remain.9️⃣ Pick your hard: Fundraising for a venture fund is 10x harder than raising for a startup. But operating a company? That’s 10x harder than running a venture fund.Timestamps:(00:00) - Introductions(01:25) - Manu’s love for dogs + How K9 Ventures got its name(03:13) - Manu’s most memorable founder story(05:18) - Origin stories(08:23) - Tough moments along Manu’s early journey(11:05) - Founder DNA(16:35) - Trusting your gut(18:05) - Founder behavior(20:35) - K9’s investing approach(24:45) - Similarities and differences between building a startups vs. investment fund(30:02) - Chief Firestarter(32:37) - HiHello(36:51) - Highlights + getting acquired(40:32) - Lowlights(41:57) - Ceremonial Final Qs

🎯 Why Specializing as a VC Is a Game Changer 🎯Natan Reddy, Principal at Ironspring Ventures, unpacks the hidden edge of being a specialist investor in industrial tech. In episode 044 of New to Venture, Natan and I get into the weeds of early VC life, from building your network from scratch to hosting high-impact events. If you’re looking to supercharge your first few years in venture, this one’s for you. Tune in!🎙️Natan and Ironspring Ventures are hosting an invite-only digital industrial breakfast for NYC Tech Week on June 3rd. If interested, apply to attend here: https://partiful.com/e/ggOlgpdXwNcjgrCraFsPMy key takeaways:1️⃣ Know how much of a software player you want to be: In industrial tech, hardware is lower margin and capital intensive. Decide how deep into software you want to go. 2️⃣ Blitzscaling rarely works in industrial: Long sales cycles and slow adoption are the norm. Don’t force consumer-style growth tactics where they don’t belong.3️⃣ Specialization attracts community: Go deep in a sector you love. Passion and expertise naturally pull in people who align.4️⃣ Master the networking flywheel: Organic connections, events, content, and pure outbound scraping, each fuels the next. Play the cycle right and your network compounds.5️⃣ It’s all about the people: We all know people make or break the job. Be kind. Be high integrity. Be a high-quality human. Surround yourself accordingly.Timestamps:(00:00) - Introductions(01:19) - Speaking at CB Insights healthcare conference(04:34) - Origin stories: Bay area vs NYC(07:59) - Origin stories: Career path(12:06) - Industrial Tech (14:10) - Challenges with investing in Industrial Tech(18:14) - Great businesses vs. venture backable companies(20:34) - Benefits of being a specialist(23:26) - Why early-stage?(24:26) - Growing and building your network(31:29) - Highlights(34:04) - NYC Tech Week Industrial Tech Breakfast!(35:39) - Ceremonial Final Qs

🔥The Blood, Sweat & Capital Behind a VC Firm 🔥Jonathan Lehr, co-founder and General Partner at Work-Bench, brings a rare mix of enterprise GTM expertise, community-first values, and long term consistency to early-stage investing. In episode 043 of New to Venture, Jon pulls back the curtain on what it really takes to build a VC firm from scratch, from Fund I to the recent $160M Fund IV! This episode is packed with practical wisdom for anyone serious about raising their own fund. Don’t miss it! 📈My key takeaways:1️⃣ Be Intentional About Hosting: Define the goal, curate the room, and design for serendipity. Collaboration follows when the right people collide with aligned incentives. 2️⃣ Serve Your Community: The more you give, the more chemical reactions you unlock. Momentum builds from meaningful contributions to founders, investors, and LPs.3️⃣ Compounding is Key: Consistency and discipline in high visibility tasks separates the real players from the noise. It’s how you beat the masses and weed out the phonies. 4️⃣ Raising a Fund is Like Enterprise Sales: LPs are similar to long-cycle enterprise customers. It is all about building deep trust. Target 10x pipeline coverage!5️⃣ Share Your Work: Take what you’re already doing and use it to create meaningful touchpoints. Share your theses, learnings, or processes. Eventually, your ideas and impact will draw the right people to you. 6️⃣ Sizing Your Fund: Take a bottom up approach. How many checks do you want to write? What ownership targets do you have? How much follow-on capital do you need? Having clear answers here will guide you to a target fund size. Not a random market number.Timestamps:(00:00) - Introductions(01:24) - Jon’s NBA player comparison(02:38) - New York Enterprise Technology Meetups + Hosting(07:36) - Morgan Stanley to VC(13:26) - Starting a firm without any venture experience(18:30) - Naming the firm(19:41) - Raising outside institutional capital(26:54) - GP - LP fit(29:24) - Fund size strategy(34:09) - What changes and stays the same as you raise more money(39:54) - Highlights and lowlights(44:39) - Ceremonial Final Qs

🌱Lessons from a career crafted through serendipity 🌱Bo Ren, Managing Director at SVB, has truly mastered the art of serendipity! In episode 042 of New to Venture, Bo takes us through the many twists and turns of her career and the valuable lessons learned along the way. We dive deep into mentorship, curiosity, and soft power. This one’s full of heart and wisdom, don’t miss out! 📚My key takeaways:1️⃣ Embrace Seredipity: Your early career doesn’t need to follow a rigid path. Although there is comfort in having a life plan, be open to unexpected opportunities and explore widely. Take on every side quest that seems interesting.2️⃣ Bet on Yourself: Often, the safest path is the one with the least room for growth or fulfillment. Every meaningful pivot requires a touch of audacity. You won’t have all the answers, but betting on your curiosity and potential will almost always lead to a more fulfilling journey. 3️⃣ Your differences are your edge: Don’t hide what makes you unique. Your differences end up becoming your superpowers. Especially in venture. VCs are looking for people who can push against their line of thinking.4️⃣ Redefine Mentorship: We tend to overcomplicate and glamorize mentorship. A mentor isn’t someone with all the answers. A mentor is someone who has walked a few steps ahead and is willing to share what they’ve learned. Don’t look for a “perfect mentor” rather start building relationships rooted in shared ambition, vulnerability, and genuine care. As a mentee, you should be building a “goodwill bank account.” Give when you can, help where you’re able, show up as your authentic self.Timestamps:(00:00) - Introductions(02:43) - HBO series: Industry + Who do you identify with?(06:34) - Setting intentions and New Years Resolutions(10:02) - Key turning points in Bo’s career(14:18) - Parents and taking the big swing(15:53) - Falling in love with startups(20:15) - Getting vocal on social media(24:33) - Creating a personal IP and an easeful life(29:03) - Soft power and invisible power laws(38:19) - Mentorship(42:47) - Highlights and lowlights(46:51) - Ceremonial final Qs

🚀 Tips from a “full-stack” VC investor! 🚀Crissy Costa Behrens, Principal at the powerhouse Insight Partners, has done it all. From being an operator, early-stage investor, growth-stage investor, and board member, her wide-ranging experience gives her a unique edge in venture. In episode 041 of New to Venture, Crissy shares her journey and top advice for the next generation of VCs. Don’t miss this one! 🎧👇My key takeaways:1️⃣ Be smart and lazy: Optimize for actions that have asymmetric upside. Focus on the inputs that have the biggest impact.2️⃣ Scrappiness wins: There is no one right way to do venture, but there are plenty of wrong ways. Hustle, creativity, and resourcefulness can be a valid differentiator. 3️⃣ Conviction closes deals: Whether you’re at a big firm or a small one, strong belief in a deal is what ultimately gets it across the finish line. 4️⃣ Get comfortable with no control: Startup outcomes are almost completely out of your hands. From market swings to global shifts to random circumstances, there is always unlimited uncertainty. Learn to embrace it. Timestamps:(00:00) - Introductions(01:44) - Crissy’s travel through Patagonia(02:59) - Crissy’s podcast: 52 Founders(06:43) - Does having a child make you a better investor?(07:49) - Origin stories(11:25) - Key learnings from Crissy’s time at Primary(12:26) - Transitioning to growth equity(14:41) - Investing in Jasper(17:22) - Do founders treat you differently based on firm?(20:38) - How Crissy wins + having a prepared mind(25:36) - Highlights(28:25) - What does a good board meeting look like?(30:00) - Lowlights(31:43) - Ceremonial final Qs