Oct 6, 2026 · 55 min · 14 segments
Send us Fan Mail What if you stopped thinking like an insurance salesperson and started building an insurance agency that could scale, operate…
David DenningHost
Elle DenningHostI think this is a great opportunity for them to learn how to start, scale, exit, repeat and think of their business in a different way.

It's going to be such a valuable conversation and it's a really good time to be having it.

I mean, I don't, I think in previous history, a comparative now, there's not a better time for especially like M&A or scaling and growing exiting businesses in the insurance space.

especially like medicare pnc there's a lot of pe that wants to acquire businesses here there's a lot of opportunity to build and scale and insurance isn't going anywhere it's been here since the dawn of time and uh it's still rocking and rolling so um I would love to start, maybe don't have to go back to the birth story, but we can go back to what was that first business you built and what really hooked you on entrepreneurship? Was it a growing up, hey, I'm entrepreneurial.
But where would you like me to start? Selling puppy dogs at the flea market, newspaper routes, a
stand after I graduated from college, flogging vegetables from the family farm, and then moving into technology.
It went public, became the second fastest, third fastest growing company in Canada.
And then after that, we did a domain extension dot club, like an alternative to dot com dot net dot org.
I think this is a great opportunity for them to learn how to start, scale, exit, repeat and think of their business in a different way.

It's going to be such a valuable conversation and it's a really good time to be having it.

I mean, I don't, I think in previous history, a comparative now, there's not a better time for especially like M&A or scaling and growing exiting businesses in the insurance space.

especially like medicare pnc there's a lot of pe that wants to acquire businesses here there's a lot of opportunity to build and scale and insurance isn't going anywhere it's been here since the dawn of time and uh it's still rocking and rolling so um I would love to start, maybe don't have to go back to the birth story, but we can go back to what was that first business you built and what really hooked you on entrepreneurship? Was it a growing up, hey, I'm entrepreneurial.
But where would you like me to start? Selling puppy dogs at the flea market, newspaper routes, a
stand after I graduated from college, flogging vegetables from the family farm, and then moving into technology.
It went public, became the second fastest, third fastest growing company in Canada.
And then after that, we did a domain extension dot club, like an alternative to dot com dot net dot org.
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