Life Wide Open with CboysTV

Episode: "From Broke to Owning 30 Million In Cars – Steve Hamilton"

Date: March 7, 2023

Episode Overview

In this energizing episode, the CboysTV crew sits down with Steve Hamilton—entrepreneur, car enthusiast, and founder of The Hamilton Collection—for an in-depth look at his journey from humble beginnings to a life surrounded by cars worth $30 million. Recorded at the impressive headquarters of The Hamilton Collection, the discussion covers Steve's business origin story, YouTube channel evolution, giving back philosophy, car culture, and lessons learned in both business and life. The episode balances practical insight and lively banter, making it valuable for both aspiring entrepreneurs and car fans.

Key Discussion Points & Insights

1. Introducing Steve Hamilton & The Hamilton Collection

• Setting the Scene (00:00–01:40):
  • The CboysTV crew arrives at The Hamilton Collection HQ, or “the car condo”, surrounded by Steve’s elite car collection.
  • Steve’s shift from being the behind-the-scenes owner of Custom Offsets, Fitment Industries, and more, to the front-facing personality on The Hamilton Collection YouTube channel.
    • “Part of that’s why we started The Hamilton Collection… and the channel’s done really well in just a year and a half.” — Steve Hamilton [01:35]

2. From Humble Beginnings to Business Success

• Early Hustle (03:06–08:43):

  • Grew up with very little money; started working at age 12, lying about his age to get his first job.
    • “I had to go. There would be field trips and I would have to show up without $5...You really learn the value of a dollar early.” — Steve Hamilton [03:06]
  • Worked a range of menial jobs: caddie, McDonald's, grocery store, while dabbling in entrepreneurial side hustles (installing radios, bike repair).
  • At 19, started drop shipping wheels and tires on eBay from his mom’s apartment—before dropshipping was trendy.
    • “Everything is about timing, right?...But yeah, I mean, I just started on ebay, drop shipping, selling wheels out of my mom's apartment.” — [05:16]

• The Beginnings of the Wheel Business (05:37–07:57):

  • Finessed his way into getting wholesale prices by pretending to be a shop.
  • Entrepreneurial passion: genuinely loved car customization, flipping cars—even if it meant (often) losing money.

3. Passion for Cars and Building a Collection

• Car Culture Mindset (07:57–14:35):

  • Lifelong car enthusiast—started with junk cars, flipping for fun, not profit.
  • Developing a network to access rare supercars and hypercars—leveraging connections to find “off-market” deals.
    • “You could really flip anything and make money if you're good enough at it...especially in the super and hypercar market...” — Steve Hamilton [11:04]
  • Discussion on cash vs. financing multimillion-dollar cars; about one-third of his fleet is financed [12:40].

• Simplifying Life and Focusing on Core Business (13:43–16:29):

  • At one point, managed ~70 different business entities; now narrowing focus to core wheel and tire businesses and seeking more family time.
  • “Part of it’s just burnout and part of it’s just like, you know, my kids are...I just really want to simplify life now.” — Steve Hamilton [13:43]

4. From Operator to Owner: Scaling and Stepping Back

• Systematizing for Success (16:29–19:15):
  • Transition from “doing $12-an-hour jobs” to scaling systems, hiring great managers, and stepping out of day-to-day operations.
  • Value of picking up “pieces from everybody” (mentorship-by-osmosis), and “learning spreadsheets” as a keystone business skill.

5. Car Life & Culture in Chicago

• Living the Car Life (19:29–21:44):

  • Drives his hypercars year-round—even in winter (“You just wash them”) [19:47].
  • Talks about online hate and car culture purists who criticize him for actually driving the cars.

• On Giving Back and Sharing Success (22:41–26:16):

  • Notably generous with his cars: lets people drive them, gives profits from the YouTube channel to charity.
    • “...Every profit and then some we give back. There’s no money that gets paid out...my wife and I go donate it.” — Steve Hamilton [02:16][22:41]
  • Talks about the impact of letting people experience these cars, receiving heartfelt letters of thanks.

6. Internet Culture, YouTube, & Viral Content

• Navigating the World of Car YouTube (27:14–35:32):
  • Stories with other creators like WhistlinDiesel, Stradman, David Dobrik.
  • Relatable YouTuber struggles: balancing content creation with the desire for real-life fun; metrics and the “pressure” of video performance.
  • Insight into YouTube algorithm: the importance of titles, thumbnails, and occasionally re-titling videos for quick performance gains.
    • “There’s a ton of little things...some of which are swapping out your titles...wait an hour, you see how the video performs, and if it doesn’t do well, you swap out...” [51:05]

7. Managing Wealth, Family, and Work-Life Balance

• Maintaining Priorities (35:42–40:10):

  • Family is central; arranges work schedule to prioritize kids and spouse, lots of family travel (especially Disney World—an obsession!).
    • “Weekends and evenings are for the family...I can schedule between, like, I pick up the kids a lot from school...” [35:56]

• Ensuring the Kids Stay Grounded (39:14–40:53):

  • Despite their wealth, wants his kids to live as “normal” as possible: “They go to public schools. I just won't put them in a private school...I want them to live a normal life as possible.” — Steve Hamilton [39:32]

8. Car Market, Investments, and Advice for the Road Ahead

• Supercar Market Analysis (45:28–47:27):

  • The used exotic car market’s crazy ride during COVID; some cars hold value (Ford GT, Porsche GT cars), others drop hard (Huracan).
    • “I think the market still has some correcting to do. It would have been a really bad time to buy it six months ago.” [45:47]

• Real Estate, Recession, and Smart Buying (56:16–66:57):

  • Real estate vs. car investing; market corrections, timing, general investment wisdom.
  • Noted the rising cost of living & rent, but observes that the average person hasn’t felt the deepest impacts of “the recession” yet [60:43–63:44].

9. Lightning Round: Memorable Stories

• Insurance Nightmares (22:41–25:12):

  • Wrecked his McLaren Senna letting others drive it, resulting in his entire collection losing insurance renewal.
    • “Country Financial decided to not renew my insurance. So I have to figure that out now.” — Steve Hamilton [23:03]

• On Speed and Growing Up (42:14–44:42):

  • “There’s a right place and a wrong place to speed...” and how growing older changes risk appetite [42:28].
  • “I used to get a ticket, two to three tickets a year. I've had well over 35, 40 tickets. I've had none in the last three years...” — [42:39]

• Disney World Obsession (36:46, 70:12–73:30):

  • “I'm huge on Disney World...I know all the secrets, like, don't flex like that.” — Steve Hamilton [71:48]

Notable Quotes & Moments (with Timestamps)

• Business Beginnings:

  • “Everything is about timing, right?...I was just selling wheels out of my mom's apartment.” — Steve Hamilton [05:16]
  • “19-year-old Steve thought it’d be a great corporate name. Real catchy one. Steve’s Discount Wheels.” [17:28]

• Generosity Philosophy:

  • “Every profit and then some we give back. There’s no money that gets paid out...my wife and I go donate it.” — Steve Hamilton [02:16][22:41]

• Car Culture:

  • “You could really flip anything and make money if you're good enough at it.” — Steve Hamilton [11:04]
  • “Always into wheels and automotive customization.” [07:07]
  • “That’s the thing—you just drive more conservative. Then [the Tesla] has autopilot. I’m like, well, I’m lazy. I’m just going to throw autopilot on and let this thing drive me at the speed limit.” — [45:08]

• On Risk & Insurance:

  • “Country Financial decided to not renew my insurance. So I have to figure that out now.” — [23:03]

• On Sharing Success:

  • “We become...numb to them...But someone will come in here for the first time and see a 765 LT or the Porsche 918...Three years later, they’ll remember that.” — Steve Hamilton [25:32]

• On Creating Content:

  • “For every one video that's work, there's two that are fun...opportunities to meet people like you guys...my son gets to meet these people, just knowing that I'm giving people access to these guys that they could have never met...” — Steve Hamilton [31:28–32:03]

• On Work-Life Balance:

  • “Weekends and evenings are for the family...That's kind of the core schedule.” — Steve Hamilton [35:56]

• Advice:

  • “There's so many more opportunities to make money [once you have some]...The rich get richer, the poor get poorer.” — Steve Hamilton [58:33]
  • “To start something without money...it's about giving up some equity and partnering with someone that can build it...” [58:33–60:23]

Important Segment Timestamps

• Steve’s Early Life and Hustle: 03:06–08:43
• Getting into Wheels & Tires: 05:37–07:57
• Building Car Network/Collection: 07:57–14:35
• Balancing Wealth and Simplicity: 13:43–16:29
• Business Systems, Early Names: 16:29–19:15
• Car Culture in Chicago: 19:29–21:44
• Insurance Trouble & Generosity: 22:41–25:12
• Driving Cars for Content: 31:28–35:32
• Family Life & Parenting Philosophy: 35:42–40:10
• Supercar Market Talk: 45:28–47:27
• On Business vs. YouTube Difficulty: 56:16–57:08
• Advice for Broke 21-Year-Olds: 58:15–60:23
• Economic/Real Estate Insights: 60:43–66:57
• Disney World Passions: 70:12–73:30

Tone & Dynamic

The tone remains upbeat, honest, and peppered with humor (especially Steve’s frequent “that’s what she said” callbacks). The camaraderie between the hosts and their guest creates a relaxed atmosphere where both fun and practical insight shine through.

Takeaways for Listeners

• Hard Work and Hustle: Steve’s trajectory underscores the importance of grit, resourcefulness, and learning as you go—especially in the absence of mentors.
• Giving Back: Success is multiplied by sharing; Steve’s philanthropic approach stands out in the YouTube automotive world.
• Enjoy the Ride: Cars are meant to be used and enjoyed, not just displayed.
• Strategic Simplicity: As you grow, consciously simplify life to focus on what matters.
• Content & Business are Both Marathons: Both require relentless effort, constant learning, and adaptation.
• It’s Never Too Late to Start: Whether it’s business, content, or family priorities—action trumps perfection.

Final words from Steve:

“You got 13 years to catch up.” [74:33]
“Thanks for having me, gentlemen. Appreciate you guys.” [74:51]

Episode Recommendation:
Check out The Hamilton Collection on YouTube for more content, and tune into Life Wide Open every Tuesday for more stories at the intersection of lifestyle, business, and adventure.