“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
2 Sept 2025TRANSCRIPT
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
27 Aug 2025
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
Inside a recent episode
Ep 050 - Molly Cantillon, Founder at NOX
Published 24 Oct 2025 · Transcript excerpt
[…] You talked about like what communication is going to look like in 10 years. What is Knox in 10 years, Molly? Yeah. So I wrote this memo a while back, which I called the invisible OS. And I think one of my other main strongly held beliefs is that AI is temporarily in this query response loop. It's temporarily on demand, but really it's going to be on accept. And what that means is it will be ambient and omnipresent. It will be woven into everyday apps and it will be almost indistinguishable from the OS, right? That's why I call it the invisible OS. It's built into the system. It feels like it's just an extension and something that you did no work to prepare and it predicts your next move always and offers to offload the work onto itself. […]
Pod Engine is an independent podcast discovery and analytics service and is not affiliated with or endorsed by this podcast. Artwork and show content belong to their owners. Full legal notice.
Explore this show Podcast research with Pod Engine
