The Struggle Years That Shape Entrepreneurs: Josh Oberlander on Building Smarter, Not Faster
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The Struggle Years That Shape Entrepreneurs: Josh Oberlander on Building Smarter, Not Faster
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What does it really take to build a business from scratch when you don’t have a roadmap? For Josh Oberlander, the answer has been equal parts grit, trial and error, and the discipline to keep sharpening himself along the way.
In this episode of Maximum Octane, Kim Hickey and Jason Patel talk with Josh Oberlander, co-founder and CRO of Detect Auto, about the unconventional path that shaped him as an entrepreneur. At 24, Josh launched a tree service business with $500 and a rope. That led to a foray into manufacturing a person-tracking fan for technicians, a product that seemed promising but came with its own hard lessons.
Josh shares why building a team is harder than most people expect, why the struggle years matter more than the highlight reel, and why continuous learning is the one thing you can never outsource. He also explains how Detect Auto helps shops save time, improve communication, and empower their staff with smarter tools.
Tune in to episode 126 of Maximum Octane if you feel stuck between where you are and where you want to go. Josh’s story is proof that persistence, awareness, and a willingness to keep learning can turn setbacks into stepping stones.
3:30 How Josh went from environmental science to running a blue-collar tree service business
5:20 Why being a skilled technician doesn’t automatically make you a business owner
9:10 Why building a team is harder than anyone teaches you
10:30 The leap from services to products and the lessons of selling a person-tracking fan to technicians
15:50 Why struggle and sweat equity are still the price of growth
20:10 Why learning is hard, but staying sharp is non-negotiable
21:30 The “Clippy for auto shops” vision behind Detect Auto
25:10 What shop owners need in place before adopting AI assistants
25:50 How Detect Auto empowers even non-technical front-of-house staff
29:20 Why the path less traveled can hold the biggest business opportunities
30:55 The entrepreneurial superpower of paying attention inside your own shop
Connect with Josh Oberlander:
- Detect Auto
- Connect with Detect Auto on LinkedIn
- Follow Detect Auto on Instagram
- Follow Detect Auto on Facebook
Let's connect:
- Website
- Email: info@maximumoctane.com
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