The $100M FOUNDER (Ex-Goldman): One Pivot Saved Us, Execution Built Us, Bad Hires Nearly Broke Us

Dylan Robbins shares how one strategic pivot scaled Lucra to $100M+, why second-time founders have an edge and why flawless execution still trumps big ideas.

Dylan Robbins is the Founder and CEO of Lucra Sports, a gamification technology company valued at over $100M. Lucra powers competitive experiences across consumer and B2B platforms. Before founding Lucra, Dylan worked at Goldman Sachs and AQR Capital Management. He previously co-founded Lifetime Vintage (acquired in 2023) and Verre Vert. He holds a B.S. in Economics from Duke University and an MBA from Stanford Graduate School of Business.

In this episode, Dylan reveals:
◽️ Why startups are "10% idea, 90% execution" (and his 1,500-idea testing system)
◽️ Why second-time founders have an edge (even after failed ventures)
◽️ How Duke/Stanford shaped his journey (and why peers over coursework)
◽️ His "life is short" philosophy with daily phone reminders
◽️ Why company culture beats profits: "If my team loves work, we've won"

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⏱ Timestamps
00:00 - Intro  
00:50 - Dylan’s background: Duke, Stanford, Goldman  
03:15 - How Lifetime Vintage started  
04:24 - Writing down one idea every day  
06:02 - Working with his wife  
07:38 - What separates successful founders  
08:40 - How COVID boosted the business  
10:15 - Life after selling his company  
11:42 - Staying motivated as a founder  
15:00 - Who shouldn’t be an entrepreneur  
16:57 - What Lucra started as  
18:30 - Realizing the bigger opportunity  
20:26 - The pivot to B2B  
21:57 - Bootstrapping vs raising VC  
23:59 - Focusing vs constantly changing  
25:04 - Balancing innovation with execution  
28:39 - Managing ambition and life balance  
30:04 - Second-time founder advantage  
31:12 - How to build credibility  
33:20 - What success means to Dylan  
35:01 - Creating a great startup culture  
38:33 - Rapid-fire Q&A starts  
38:33 - Best advice he’s received  
38:53 - A question he’s never asked  
39:14 - What he loves about startups  
39:45 - What happiness means to him  
40:23 - His personal philosophy  
41:14 - Compartmentalizing stress  
42:19 - Handling uncertainty  
42:55 - Lessons from entrepreneurship  
44:14 - A day he’d relive  
45:35 - Knicks vs baby debate  
46:10 - What’s next for Dylan  
47:00 - How he wants to be remembered  
47:42 - One takeaway for listeners  
48:22 - Host’s closing thoughts  
49:00 - Final thanks  
49:18 - Outro  


📌 Resources
Dylan Robbins
◽️ Linkedin: https://www.linkedin.com/in/dylan-robbins-56338b63/

Harvey Bracken-Smith:
◽️ Website: www.personable.media
◽️ Email: ADD COMPANY EMAIL
◽️ LinkedIn: linkedin.com/in/harveybracken-smith
◽️ Instagram: instagram.com/harveybsmith
◽️ X (Twitter): x.com/harveybsmith_

Personable Podcast:
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◽️ Apple Podcasts: podcasts.apple.com/us/podcast/personable/id1671640111

Additional:
◽️ The Draft (Sign up): thedraft.io
◽️ Fundraising: justgiving.com/crowdfunding/LouLouRacefoiundation?utm_term=PvByaxmdn

Personable is a podcast dedicated to helping listeners become the best they can be by learning from the world’s best in their respective fields. This mission is inspired by my mother, Louise, who encouraged me to become the best version of myself before she passed away from cancer in 2023.