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HBO and The Ringer's Bill Simmons hosts the most downloaded sports podcast of all time, with a rotating crew of celebrities, athletes, and media staples, as well as mainstays like Cousin Sal, Joe House, and a slew of other friends and family members who always happen to be suspiciously available.
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Episode Stack: https://stackl.ist/3W1QAGR
I had THE BEST conversation with Caroline Clark, Co-Founder and CEO of Arcade, about the journey from zero to building a product that's changing how teams create interactive demos.
We talked about her path from consulting to product marketing at companies like Atlassian, and what led her to start Arcade. What stood out to me was her honesty about the hard parts of building a company. The burnout, the failed launches, the moments at 4:30 AM questioning everything.
Some things that stuck with me:
• Why the best market isn't always the obvious one
• The real cost of being on the hook for marketing output (and why she built Arcade)
• How a "failed" product launch became their most successful enterprise offering
• The importance of staying close to what brings you joy when building
If you're in the early stages of building something, Caroline's advice about being passionate and not getting too attached to one-off moments is worth hearing. She's built up what she calls a "lower bar for embarrassment" over time, which feels like an underrated founder skill.
Chapters
00:46 - Introduction and Background
11:52 - Early Career and Transition to Marketing
25:21 - Joining Atlassian and Learning from Failures
34:12 - The Importance of Market Fit
45:44 - Venture Capital Insights and Growth Mindset
56:30 - Building Arcade: Challenges and Successes
1:09:18 - Future of Arcade and AI Investments
1:22:14 - Advice for Aspiring Entrepreneurs
Chapters
1. Caroline Clark - Arcade (00:00:00)
2. Introduction and Background (00:00:46)
3. Early Career and Transition to Marketing (00:11:52)
4. Joining Atlassian and Learning from Failures (00:25:21)
5. The Importance of Market Fit (00:34:12)
6. Venture Capital Insights and Growth Mindset (00:45:44)
7. Building Arcade: Challenges and Successes (00:56:30)
8. Future of Arcade and AI Investments (01:09:18)
9. Advice for Aspiring Entrepreneurs (01:22:14)
29 episodes
