From Microsoft to Military Decals: How Tim Built Freedom Through Buying Businesses - Tim Lewis
Description
What happens when a former Microsoft exec trades the corporate fast track for small business ownership? In this episode of What’s Your Deal?, Matt sits down with long-time friend and client Tim Lewis to explore his journey from tech giant to serial entrepreneur.
Tim shares how he left a thriving career at Microsoft, launched a consulting firm, built and scaled a web design agency using international talent, and ultimately found financial freedom by acquiring a niche e-commerce business serving veterans and military families.
Timestamps:
02:10 – Early career at Microsoft and discovering business ownership
05:00 – Leaving corporate life for Arizona and small business consulting
05:50 – Launching a web design agency without knowing how to code
08:15 – Scaling using offshore talent and building a global team
11:30 – Acquiring a business to grow fast
13:00 – Burnout, customer service issues, and quality-of-life tradeoffs
16:00 – Selling the web company and taking time off
17:00 – Evaluating businesses and what made him say no
19:30 – Buying the military decal business and scaling it
21:00 – Why reviews and customer service mattered more than tech
24:10 – Using automation and AI to streamline production
25:44 – Starting vs. buying a business: which is better?
27:50 – Advice on higher education and surviving AI’s impact
30:00 – Work-life balance, flexible hours, and redefining success
34:40 – Who helped him most in his career
38:00 – His #1 rule for success: say yes and figure it out later
Resources & Links
Military Grapics - https://militarygraphics.com
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