New to Venture

Ep 050 - Molly Cantillon, Founder at NOX

“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

Ep 049 - Nate Leung, Partner at Sapphire Partners

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

Ep 048 - Chauncey Kerr Hamilton, Partner at XYZ Venture Capital

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

Ep 047 - Bryan "BK" Kim, Partner at a16z

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

Ep 046 - Grace Ge, Partner at Amplify Partners

“If you have to ask someone to be your mentor, they are not your mentor.” Meet Grace [https://www.linkedin.com/in/gracewenge/], a partner at Amplify Partners [https://www.amplifypartners.com/] 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 [https://open.spotify.com/playlist/6Bt6uicPPEo98ONJIf2KlR?si=tcWEn3wXTSuJ81in-qJVuQ&pi=R5J5WlksSbOUy&nd=1&dlsi=dd196650ce534fba] - 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 Qs Subscribe on Youtube [https://www.youtube.com/@NewtoVenture] Follow on Spotify [https://open.spotify.com/show/50xMxGuDaMjMLzsLzGTzXo] Follow on Apple Podcasts [https://podcasts.apple.com/us/podcast/new-to-venture/id1711344638] Follow Taiki on LinkedIn [https://www.linkedin.com/in/taikichung/]