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The Career Flipper Podcast

Hosted by Jenny Dempsey

Thinking about making a career change but have no idea where to start? You’re not alone. Welcome to The Career Flipper, the podcast for anyone wondering, "What else is out there?". I’m Jenny Dempsey—your host and a fellow career flipper.

87 episodes · publishes weekly · latest 2025-11-06

Rank

#218

Substance

23.0

/ 100

Why it scores where it does

The Career Flipper Podcast ranks #218 on The B2B Podcast Index with a substance score of 23.0 out of 100, scored across 3 recent episodes. It scores highest on guest caliber and specificity & evidence. The guest is a solo dog walker who built a modest one-person business; sincere and relevant to his niche but not an operator who has done anything at scale relevant to B2B audiences.

The five-dimension breakdown

Averaged across 3 recently scored episodes, with cited evidence.

Insight Density

3.7 / 20

The episode is a personal career-change narrative with very few transferable business insights; the rare operator-relevant nuggets (platform take rates, going direct, local marketing) are thin and surrounded by emotional reflection and platitudes.

“they were taking 40% of what you made. So the splits are insane”

“I'm going to start talking to them all. Yeah. See if they'll go off the app”

Originality

4.3 / 20

The takes are familiar self-help fare—'take small steps,' 'you won't know until you try,' 'loving something doesn't mean you should work in it'—with little contrarian or first-principles thinking for an operator.

“there is no like get-rich-quick schemes”

“You're never going to know with anything until you try it”

Guest Caliber

6.0 / 20

The guest is a solo dog walker who built a modest one-person business; sincere and relevant to his niche but not an operator who has done anything at scale relevant to B2B audiences.

“I have my own dog walking and pet sitting business here in LA”

“I'm going to take as many walks as I can myself”

Specificity & Evidence

4.7 / 20

There are a few concrete data points—$25,000 salary, 40% platform cut, 12-18 clients/day, doubling income off-app, COVID retention—but most of the conversation stays in feelings and generalities rather than hard numbers.

“I think my first year I was paid like $25,000”

“they were taking almost half of it”

Conversational Craft

4.3 / 20

The host is warm and asks open questions but engages in very long, leading, self-referential monologues and never pushes back or probes the business mechanics; it's a supportive chat rather than a challenging interview.

“thank you for believing in yourself enough to try”

“I'm so curious about this because I think a lot of us fear that moment”

Standout episodes

Rank over time

First period on the Index - history builds from here.

Episodes

3 scored on substance · 60 tracked in total.

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