How he built the future for 1M freelancers

28/07/2025 16 min
How he built the future for 1M freelancers

Listen "How he built the future for 1M freelancers"

Episode Synopsis


Ben Huffman built a company everyone called stupid. Until more than 1M people were using it.In this episode of State of Play, the Contra's design founder shares how he went from college dropout to building a new path for creative independence.We get real about the pain cave: that brutal, lonely gap between your vision and the world’s doubt, and how to keep going when no one believes in you.If you’re building something and feel like no one gets it, this one’s for you.Get the UX Tools NewsletterJoin 100,000+ designers for weekly insights on creative software and the people shaping it: https://uxtools.coCHAPTERS:00:00 - Why investors laughed02:04 - Getting your first client03:03 - Trust issues with platforms04:32 - Building with 0% commission05:40 - The sting of rejection07:36 - Near burnout and losing it all08:57 - How Contra makes money10:02 - A 20-year-old earns $50k12:24 - $50k/month playbook13:40 - Why it’s a great time to be creative14:25 - The “Hollywood model” shiftSPECIAL THANKS:- Sam Chapman: https://x.com/editedbysam- Mapal Berenson: https://www.youtube.com/@mapal- Bernabe Bolanos: https://www.youtube.com/@BernabeBolanos- Adam Stewart: https://www.instagram.com/adnastu/- Tom Fox: https://catalog.tomfox.site/ABOUT TOMMY GEOCOI spent 15+ years in tech and design. Former military. Father of five. Now building Internet Enjoyers, a weird little media + product studio rediscovering soul in creative tech. This show is how I stay sane and spotlight the outsiders reshaping how we enjoy the internet.ABOUT STATE OF PLAYA narrative podcast about building things that matter told through deep conversations with designers and builders. LINKSUX Tools Newsletter: https://uxtools.coFollow Ben: https://x.com/_BenHQCheck out Contra: https://contra.com