What's Your Deal? – Insights on Business Acquisitions and Management for Smart Investments
What's Your Deal? - Insights on Business Acquisitions and Management for Smart Investments
Podcast Description
A podcast for business buyers, sellers, and investors seeking real insights into small business acquisitions. Hosted by Matt Uhler, we break down deals, success stories, and expert strategies.
Podcast Insights
Content Themes
The podcast addresses various themes around small business acquisitions, including financing strategies, personal success stories, and the insights of industry professionals. Notable episodes cover financing basics with expert Lindsay Denton, a transition from real estate to business ownership with Luke McCarthy, and a corporate-to-entrepreneur journey with Keith Sklarsky, focusing on practical strategies for aspiring business buyers and sellers.
A podcast for business buyers, sellers, and investors seeking real insights into small business acquisitions. Hosted by Matt Uhler, we break down deals, success stories, and expert strategies.
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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