Episode 547: James Dumoulin: The Kid Who Built an 8-Figure Business By Asking Billionaires How Much They Make

Habits and Hustle

Jen Cohen

Entrepreneurship, Education, Self-improvement, Health & Fitness, Business

4.5 • 818 Ratings

🗓️ 21 April 2026

⏱️ 87 minutes

🔗️ Recording | iTunes | RSS

🧾️ Download transcript

Summary

I live by one rule that has shaped almost every good thing in my career: do the thing first and ask for forgiveness later. Not permission. Forgiveness. The people who wait for the right connection, the right introduction, the right moment, usually end up watching someone bolder walk past them into the room they were trying to get into. That is exactly why I wanted to sit down with James Dumoulin. James is the 23-year-old founder of School of Hard Knocks, the media brand you have almost certainly seen on your feed even if you never clocked the name. He is the guy who walks up to strangers in G-Wagons and Rolexes and asks them how much money they make. That one move, repeated enough times, turned into 48 billionaire interviews, 22 million followers, and an 8-figure business before most people his age have figured out what they want to do after college. In this episode, James breaks down how he actually built the empire, the business decisions that saved it, why he turned down hundreds of thousands in easy sponsorship money, and the one question he asks every wealthy person he meets. He also gets into what he thinks his own generation is getting wrong, why the gatekeepers are the reason most people never land the meeting, how he cold-emailed Mark Cuban and got a yes in three seconds, and the moment going viral almost cost him everything. If you have ever hesitated to make the ask, send the email, or walk up to the person, this conversation will change how you think about what is actually possible. What's Discussed: (02:15) How James went from working at Chick-fil-A to building School of Hard Knocks. (08:20) How he got Mark Cuban as his first big interview through a cold email. (11:05) The only metric on social media that actually matters. (14:30) What makes the first three to five seconds of a video work & why the hook is everything. (18:45) Why going viral once is not a business and how the platforms can take it all away overnight. (21:20) The moment School of Hard Knocks went from $30k a month to under $5k in a single day. (24:10) Why Facebook pays more than Instagram, TikTok, and YouTube combined. (26:30) The sponsorships James turned down to protect the brand. (31:15) How he built multiple businesses on top of the content. (36:00) What it is actually like behind the scenes trying to interview Tom Cruise. (40:20) Why the most successful people are the easiest to reach and the gatekeepers are the real bottleneck. (46:10) What James thinks his own generation is getting completely wrong about work and life. (52:30) The one piece of advice from a Goodyear executive that James has lived by ever since. (58:15) The mindset shift that separates billionaires from everyone else. (1:04:40) Why he still edits every single video himself even with 70 employees. (1:10:25) How to build a personal brand if you are starting in your 40s or 50s and not fluent in digital. (1:15:50) What is next for The School of Hard Knocks and the new channels James is building. Thank you to my sponsors!Kion: Visit getkion.com/habits for 20% off. AirDoctor: Head to AirDoctorPro.com and use promo code HUSTLE to get up to $300 off today! AirDoctor comes with a 30-day money back guarantee, plus a 3-year warranty (an $84 value) FREE! AX3®: Visit www.AX3.life to get a 20% discount on your first order with promo code HUSTLE at checkout. Magic Mind: Head over to www.magicmind.com/jen and use code JEN at checkout. Find more from Jen Cohen: Website: www.jennifercohen.com Instagram: @therealjencohen Books: www.jennifercohen.com/books Speaking: www.jennifercohen.com/speaking-engagements Find more from James Dumoulin: James’s Instagram: @realjamesdumoulin School of Hard Knocks Instagram: @theschoolofhardknockz School of Hard Knocks YouTube: @theschoolofhardknocks School of Mentors YouTube: @jointheschoolofmentors School of Mentors Community: https://www.skool.com/schoolofmentors School of Content Consulting: https://www.skool.com/schoolofcontent

Transcript

Click on a timestamp to play from that location

0:00.0	Hi, guys. It's Tony Robbins. You're listening to Habits and Hustle. Crush it.
0:07.7	Welcome to Habits and Hustle with me, Jen Cohen, where we break down the mindsets and strategies behind extraordinary success.
0:15.6	And today, I'm talking to someone you've definitely seen, even if you don't know him by name.
0:22.7	It's James DeMulian. He is the 23-year-old behind School of Hard Knocks, known for walking up to people in Rolexes and G-Wagons,
0:29.7	and asking one simple question, how much money do you make? He's interviewed 48 billionaires,
0:35.7	built a following of over 22 million, and created an eight-figure business before most people his age even have a career.
0:44.9	But what you don't see, going viral almost broke him.
0:48.5	In this episode, we get into how he built it, nearly lost it, and what he learned from the world's most successful
0:55.3	people, including the one question you should start asking today.
1:00.5	So let's dive in.
1:07.9	Okay, you guys are super, I am like a giddy school girl with you.
1:12.6	I really, it really is like, I could be your mother, but yet I'm so excited to sit here with you because you've done such a phenomenal job at building, just building a brand, building a media or on your way of building a media empire.
1:27.3	I'm sitting here with the School of Hard Knocks,
1:30.2	James Dumolin. That's it. Right? Oh, like sweating. I thought I was going to get that wrong.
1:35.4	Who I really, as you can see, I genuinely love your content. I love what you've done. I'm sure you get
1:42.6	stopped a thousand times a day. Do you get stopped a thousand times a day.
1:44.4	Do you get stopped a thousand times?
1:45.7	Yeah, it doesn't matter where we are at this point,
1:47.9	whether we're here in Los Angeles or we were at London last week, Dubai, all over.
1:52.8	It's cool to see how the international presence has really grown beyond just, like,
1:56.4	locally where we live in Austin, Texas.
1:58.3	It's amazing.
	...

Please login to see the full transcript.

Previous episode | Next episode

Disclaimer: The podcast and artwork embedded on this page are from Jen Cohen, and are the property of its owner and not affiliated with or endorsed by Tapesearch.

Generated transcripts are the property of Jen Cohen and are distributed freely under the Fair Use doctrine. Transcripts generated by Tapesearch are not guaranteed to be accurate.