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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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Ben Huffman built a freelance platform with NO fees. Every investor told him it was the stupidest idea they’d ever heard.
Now Contra has 1M users and a $120M run rate.
We talk about living in the pain cave (the place your ideas live before anyone believes in them), building mission-driven companies, avoiding the “marketplace commodity problem,” and why community-led growth might be the future of creative work.
Get the UX Tools Newsletter (written by me)
Join 90,000+ designers for weekly insights on creative software and the people shaping it: https://uxtools.co
CHAPTERS:
00:00 – The “pain cave” explained
01:12 – Investors called it the “worst idea ever”
04:51 – Why rejection always feels personal
07:32 – Building for the younger version of yourself
10:47 – The humanity problem with commission fees
13:41 – Early internet communities (Themeforest, torrent sites, Newegg)
15:30 – Solving the marketplace commodity problem
18:44 – Going “feed first” to foster authentic connections
20:28 – Becoming an independent discovery engine
24:08 – Partnering with creative tools like Framer
27:26 – Why open networks might win over closed platforms
30:28 – Building leverage as an independent creative
33:53 – The “Hollywood model” for creative projects
37:55 – Resumes are dead, project-based identity is the future
40:39 – Small core teams + specialist networks
43:17 – How indie communities share work and clients
46:05 – Branding yourself to get discovered
48:01 – The story of a 19-year-old making $50K/month from design
50:31 – How Contra makes money without fees
52:21 – Almost out of the pain cave
LINKS:
UX Tools Newsletter: https://uxtools.co
Follow Ben: https://x.com/_BenHQ
Try Contra: https://contra.com
FOLLOW ME:
Instagram: https://instagram.com/itsdesignertom
X / Twitter: https://x.com/designertom_
LinkedIn: https://linkedin.com/in/tommygeoco
TikTok: https://tiktok.com/@designertom
Threads: https://threads.net/itsdesignertom
NARRATIVE EPISODE:
Spotify: https://open.spotify.com/episode/2CrESEW03tMCrVGMCWlO8d?si=NVpYWxEKSVugGu5okwvh7w
Apple Podcasts: https://podcasts.apple.com/us/podcast/he-built-a-freelance-platform-with-no-fees-now-1m-use-it/id1829478829?i=1000719514305
6 episodes
