Two Hosts. Zero in Common.
Ten Questions That Get Real.
Ten Questions That Get Real.
Entrepreneurial Odd Couple is the podcast where an introvert and an extrovert sit down with business owners who’ve actually built something — and ask the questions that get past the highlight reel.
Every episode, we sit down with a business owner and ask the same ten questions — the ones that cut through the “hustle culture” highlight reel and get to what actually happened. How they started. What broke them. What they’d do differently. What they’re genuinely proud of.
One of us will ask the quiet, thoughtful follow-up. The other will say the thing everyone’s thinking. Somewhere in the middle, you get an hour that’s honest, a little unpredictable, and packed with ideas you can actually use.
Why Listen
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Unscripted, not chaotic.
Every episode follows the same 10 questions — but the answers never go where you expect.
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Built for people building things.
Founders, freelancers, side-hustlers — if you’re figuring it out as you go, this is for you.
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Golden nuggets, not platitudes.
We push past “work hard and believe in yourself” to the specific habit, decision, or mistake that actually moved the needle.
Never miss an episode. Entrepreneurial Odd Couple drops new on
YouTube, Spotify, and Apple Podcasts.
Know a business owner
with a story worth ten questions?
with a story worth ten questions?
Nominate a guest or pitch yourself — we’re always
looking for the next honest conversation.
looking for the next honest conversation.