His first business idea sold one unit on eBay, for 99 cents.
Eight years later, a product he admits he’s not even proud of has done over $100 million in sales. It’s soap. Little hotel-style soap and shampoo kits.
Steve Rolle served as a US Army officer, took a corporate job he lasted six months in, and went on to build businesses that have generated over $100M in combined sales. But the money isn’t what stuck with me after this conversation. It was the question he asks everyone he meets: are you living the life you chose, or the one you inherited?
In this episode we get into:
- How Steve was earning three times his army salary from his side business, and still had to take a day job. The reason will annoy every business owner listening.
- The idea that failed twice before it worked, and the small shift that made it sell out on Amazon without spending a penny on ads.
- Why he walked away from a $6.2M offer from a public company and did something very different instead.
- Why he thinks the “just buy a boring business” advice on social media is getting people into trouble.
- The point where he was making $300 a day and wanted to quit, and what that taught him about himself.
- How to step back from your business without it falling apart.
- Why he believes your “safe” job might be the riskiest thing you have.
- His biggest regret, and the insecurity he kept from other founders for years.
- If you’ve ever felt stuck in a path someone else picked for you, give this one a listen.
TIMESTAMPS
0:00 Intro
1:00 From army officer to a corporate job he never wanted
4:23 Is your job really secure?
10:42 The failed ideas behind a $100M business
15:50 Why boring businesses are overhyped
19:12 Low-stress reps and why they matter
23:35 The merger and turning down $6.2M
31:00 Founders getting out of their own way
34:00 Fixing founder dependency
41:54 Building a personal brand over ten years
47:00 Steve’s book, The Future You Choose
50:22 Why being a control freak is a good thing
54:23 Quickfire questions
What was your biggest takeaway? Let me know in the comments.
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