Johnny DeMaddalena straddles two worlds: service in the Army Reserves and scaling startups in the civilian sector. In this episode, we unpack his unique journey - from starting a dog treat company in high school to launching a web platform for small businesses.
Johnny shares lessons from trial-and-error ventures, his approach to time-boxing new ideas, and how being a reservist has shaped his entrepreneurial mindset.
We cover:
What it’s like to “transition” every month as a reservist
Why Guard/Reserve can be a powerful option after active duty
His time with privacy-focused voice tech, real estate ops, and Bitcoin hedge fund modeling
Launching Wirechunk to simplify web presence for small businesses
How programmatic SEO can drive local service success
Johnny’s framework for choosing what venture to pursue next
How the Army taught him to operate on short timelines and why that’s a superpower
His open offer: weekly office hours to help fellow veterans build and brainstorm
Takeaway Quote:
“If you’re getting out of the military and you’ve got 15 ideas - ask around. Someone’s already been there and can help you take the next step.”
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Connect with Johnny: https://www.linkedin.com/in/john-demaddalena/
Wirechunk: https://wirechunk.com/
Calendly Vet Office Hours: https://calendly.com/johnny-wirechunk/veteran-office-hours
-------------------------------------------------------------Connect with Griffin: https://www.linkedin.com/in/griffinbrand/
Connect with Jack: https://www.instagram.com/hawaiimortgagebroker/
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If this episode resonated with you, share it with a fellow veteran or service member navigating their transition. Your review and rating help inspire more veterans with stories like Johnny's.
And as always: Go do the thing. Make that decision. Find your next mission.