Michael Gilroy on Founding Marathon, the Rule of 200, and the Future of Fintech

Story as Leverage: From Glossier to Coalition w/ Ashley MayerAshley Mayer

Ashley Mayer is a Co-Founder and General Partner at Coalition, an early stage venture firm powered by active operators. Coalition invests at the Pre-Seed and Seed and is obsessed with connecting founders in their portfolio and beyond with world class operating talent. In this episode, Ashley shares her path from Box during IPO prep, to shaping narrative at Social Capital, to helping build Glossier, and ultimately starting Coalition. We discuss storytelling as a true competitive advantage, messaging versus story market fit, intentional cap table design, and why we are in a particularly sloppy era for startup storytelling. Ashley also shares advice for first-time angels and emerging managers. A grounded conversation on narrative, conviction, and building companies and funds with intention. Learn More About Nucleus: https://nucleustalent.io/ Follow Alex: https://x.com/alexklein0x  Timestamps: 00:00 - Welcome to The Rise 01:41 - Why storytelling matters 03:38 - Lessons from Box and Social Capital 07:26 - Glossier and consumer storytelling 10:11 - Founding Coalition 21:05 - Intentional cap tables 25:02 - Human energy and company building 25:58 - Messaging versus story market fit 29:35 - First-time versus repeat founders 31:17- Expertise, AI, and credibility 38:30 - The sloppy era of storytelling 40:05 - Advice for emerging managers 45:23 - One company Ashley admires 46:20 - An emerging manager to watch 47:20 - Closing #venturecapital #investing #podcast #vc #startup #tech

Michael Gilroy on Founding Marathon, the Rule of 200, and the Future of Fintech

Michael Gilroy is the Founding Partner at Marathon. In this episode, we unpack Michael’s path from Canaan to Coatue and the decision to launch Marathon alongside Gokul Rajaram. We dive deep into the Rule of 200, Michael’s framework for evaluating fintech companies, how he thinks about global fintech expansion, what it takes to build a four-pillar investment team, where he sees Marathon a decade from now, and his advice for emerging fund managers building enduring firms. Learn More About Nucleus: https://nucleustalent.io/ Follow Alex: https://x.com/alexklein0x  Timestamps: 0:00 - Welcome Michael Gilroy To The Rise 00:59 - 2025 as the year of the spinout 05:16 - Founding Marathon 10:00 - Hosting startups inside the Marathon office 12:30 - Why building in different geographies matters 13:25 - What an ideal Marathon company looks like 17:57 - Michael’s path into venture capitall 28:00 - Getting hired at Coatue 34:30 - Investing in Mercury and broader fintech trends 37:59 - The rise of angel investing among founders 40:05 - The Rule of 200 43:35 - Challenges of global expansion in fintech 46:50 - How Michael defines his investment style 49:54 - The four partners at Marathon and building the firm 56:00 - The fintech white paper 57:30 - Marathon in 10 years 01:00:16 - Rapid fire: one founder to back, one LP you’re grateful for 01:01:54 - Advice for emerging managers 1:05:20 - Which firm Michael would prioritize getting allocation in 1:07:00 - Thanks for joining, Michael #venturecapital #investing #podcast #vc #startup #tech

The Rise of Work-Bench: Inside the $375M Enterprise Fund w/ Jonathan Lehr

Jonathan Lehr is the Co-Founder and General Partner of Work-Bench, the NYC early-stage enterprise firm managing $375M across four funds with investments in companies such as Socure, Spring Health, and Cockroach Labs. In this conversation, we walk through the origin story of Work-Bench, how the team planted a flag in New York’s enterprise ecosystem, the role of community in their model, and the experience of navigating institutional LPs as an emerging manager. Jonathan also shares how Work-Bench evaluates early GTM strength, lessons from backing category-defining companies, and what is ahead as the firm raises Fund IV. Learn More About Nucleus: https://nucleustalent.io/ Follow Alex: https://x.com/alexklein0x Timestamps: 0:00 — Welcome Jonathan Lehr to The Rise 0:45 — Planting the Flag in NYC’s Enterprise Ecosystem 3:03 — The Enterprise Tech Meetup: Bridging Corporates and Startups 5:39 — Raising Fund I to $160M: The Early Grind 7:44 — How NYC’s Tech Landscape Evolved 9:58 — Institutional LPs: Navigating Process, Challenges, and Momentum 14:55 — Portfolio Deep Dive: Spring Health and Socure 24:05 — How Work-Bench Evaluates Startups & GTM Strength 26:12 — Community as a Durable Moat 31:23 — Go-to-Market Lessons From the Portfolio 33:53 — Preparing Founders for the Series A 40:16 — Raising Fund IV: What’s Changing 44:42 — Shoutouts & Emerging Managers to Watch 48:30 — Thank You Jonathan — Like & Subscribe #venturecapital #investing #podcast #vc #startup #tech

Turner Novak: Building Banana Capital and a Following That Compounds

Turner Novak is the founder and solo GP of Banana Capital and the host of The Peel Pod, with guests spanning from Benchmark’s Eric Vishria and Cendana’s Mike Kim to Weekend Fund’s Ryan Hoover and Sweetgreen’s founder and CEO, Jonathan Neman. From his beginnings in Winnipeg to building Banana Capital out of Ann Arbor, Turner has become one of the most recognizable and trusted voices in venture, known for pairing curiosity and humor with real conviction. He’s built a following of hundreds of thousands and a portfolio that includes BeReal, ScienceIO, Bee, Chainguard, and more. On this episode of The Rise, Turner unpacks the origin of Banana, the flywheel behind his personal brand, and how he’s built a reputation for speed, transparency, and founder trust. Learn More About Nucleus: https://nucleustalent.io/ Follow Alex: https://x.com/alexklein0x  Timestamps: 0:00 [https://x.com/alexklein0x/status/1988280876262912136?t=0] – welcome turner novak to the rise 0:48 [https://x.com/alexklein0x/status/1988280876262912136?t=48] – from winnipeg to venture 2:15 [https://x.com/alexklein0x/status/1988280876262912136?t=135] – building banana capital from scratch 5:32 [https://x.com/alexklein0x/status/1988280876262912136?t=332] – discovering the power of social 9:41 [https://x.com/alexklein0x/status/1988280876262912136?t=581] – creating the peel pod and landing top guests 13:50 [https://x.com/alexklein0x/status/1988280876262912136?t=830] – portfolio wins: bereal, scienceio, bee, chainguard, and more 17:22 [https://x.com/alexklein0x/status/1988280876262912136?t=1042] – the art of moving fast and earning trust 21:03 [https://x.com/alexklein0x/status/1988280876262912136?t=1263] – raising institutional capital and lessons learned 25:26 [https://x.com/alexklein0x/status/1988280876262912136?t=1526] – how social compounds into deal flow 29:17 [https://x.com/alexklein0x/status/1988280876262912136?t=1757] – what founders really want from investors 33:08 [https://x.com/alexklein0x/status/1988280876262912136?t=1988] – what’s next for banana capital #venturecapital #investing #podcast #vc #startup #tech

Inside Also Capital: Mike Annunziata on Conviction, Builders, and the Future of Hard Tech

At Also Capital, Mike Annunziata partners with founders solving the hardest problems in space, energy, and advanced manufacturing. His portfolio includes Radiant Nuclear, Northwood Space, and Varda Space Industries where he serves on the board. We talk about the mindset behind conviction investing, the role of trust in early partnerships, and and what it means to be the first call for frontier builders. Learn More About Nucleus: https://nucleustalent.io/ Follow Alex: https://x.com/alexklein0x  Timestamps: 0:00 – Welcome Mike Annunziata to The Rise 0:45 – Early influences and what shaped his mindset as an investor 2:20 – From Soros Fund Management to founding Also Capital 6:05 – Backing the next generation of Hard Tech founders 10:12 – Inside the portfolios of Varda Space, Radiant, K2 Space, Northwood, and ConductorAI 14:18 – Serving on the board at Varda Space and staying close to the build 18:07 – Conviction before consensus: how Mike makes early calls 23:26 – The role of trust and partnership in company building 28:35 – Building Also Capital as a firm with long-term gravity 33:42 – Lessons from operating and investing in frontier sectors 39:50 – How the next era of Hard Tech will be built 44:55 – Rapid-fire questions 47:30 – Closing reflections and advice for emerging managers #venturecapital #investing #podcast #vc #startup #tech