Skip to content
Lady Bosses (and Ben) podcast artwork

PODCAST · tv

Lady Bosses (and Ben)

by iHeartPodcasts

Ben Higgins has come a long way since his “Perfect Ben” days on The Bachelor, and now he wants to take you along as he explores being an entrepreneur! He’s enlisted the help of venture capitalist Jesse Draper, whose firm has helped with early stage investing in female founded startups, like Carbon 38 and Sugarfina. She combines her background in comedy and entertainment with her vast business experience to provide an accessible and relatable approach to the board room. Each week, they’ll sit down with a different CEO or entrepreneur, and learn how they achieved their goals, what challenges they face, and the tips they can share with the next generation.

Publisher-supplied feed metadata · PodParley refreshed Apr 12, 2026 · Source feed

Episodes

  1. Defining Success with Nicole Lapin

    What does the word “success” mean to you? Ben and Jesse attempt to define that elusive term by talking to “Boss Bitch” author and financial expert Nicole Lapin. She saw that people aren’t getting enough financial education, so she started her own school to help people become smarter with money.…

    more
  2. Poppin Bottles

    Adam Callinan, founder of BottleKeeper is here to tell us all about what it was like growing a business on Shark Tank, how to take a rough prototype and turn it into a successful product, and the importance of listening to customer feedback. Plus Jamie Geffen from Geffen Events is hanging out…

    more
  3. Baking Your Business

    Who doesn’t love cupcakes?? But with so many places to get cupcakes, you may wonder what separates one from the rest. To answer that question, Jesse and Ben talk to Melissa Ben-Ishay of “Baked By Melissa”. She lets us in on how she sets herself apart from the other cupcake bakeries, and we hear…

    more
  4. From a Housewife to a Lady Boss with Tanya Sam

    Ben Higgins and Jesse Draper sit down with Tanya Sam from The Real Housewives of Atlanta to talk about her expertise with investing in tech, and what it’s like working with her husband on business ventures. Tanya and Ben bond over their similar experiences in business and being on reality TV. And...

  5. Donuts & Blowouts

    How do you start a successful business from just blowouts? Allie Webb from DryBar is here to answer that question with Ben and Jesse. She offers some advice about how to pick out a physical location for your business, and she talks about the pros and cons of working with your spouse. Then we hear...

  6. Ham Ice Cream & Alison Sweeney

    You may think you know Ben Higgins from The Bachelor, but he’s here to explore a different side of him that you didn’t see on TV. His co-host, Jesse Draper, kicks off this episode with some background into her personal and professional life, and she reveals how she picks a company to invest in....

  7. Brooklyn Decker

    Jesse and Ben talk to supermodel and entrepreneur Brooklyn Decker about how to take an idea to the next step, and what it was like to start a business during a pregnancy. Learn more about your ad-choices at https://www.iheartpodcastnetwork.com See omnystudio.com/listener for privacy information.

  8. Teaser

    Here's a taste of Lady Bosses (and Ben)! Get to know entrepreneur Jesse Draper, and see a different side of Ben Higgins than what we've seen on The Bachelor. Learn more about your ad-choices at https://www.iheartpodcastnetwork.com See omnystudio.com/listener for privacy information.

Type above to search every episode's transcript for a word or phrase. Matches are scoped to this podcast.

Searching…

We're indexing this podcast's transcripts for the first time — this can take a minute or two. We'll show results as soon as they're ready.

No matches for "" in this podcast's transcripts.

Showing of matches

No topics indexed yet for this podcast.

Loading reviews...

ABOUT THIS SHOW

Ben Higgins has come a long way since his “Perfect Ben” days on The Bachelor, and now he wants to take you along as he explores being an entrepreneur! He’s enlisted the help of venture capitalist Jesse Draper, whose firm has helped with early stage investing in female founded startups, like Carbon 38 and Sugarfina. She combines her background in comedy and entertainment with her vast business experience to provide an accessible and relatable approach to the board room. Each week, they’ll sit down with a different CEO or entrepreneur, and learn how they achieved their goals, what challenges they face, and the tips they can share with the next generation.

HOSTED BY

iHeartPodcasts

CATEGORIES

Frequently Asked Questions

How many episodes does Lady Bosses (and Ben) have?

Lady Bosses (and Ben) currently has 8 episodes available on PodParley. New episodes are automatically indexed when they're published to the podcast feed.

What is Lady Bosses (and Ben) about?

Ben Higgins has come a long way since his “Perfect Ben” days on The Bachelor, and now he wants to take you along as he explores being an entrepreneur! He’s enlisted the help of venture capitalist Jesse Draper, whose firm has helped with early stage investing in female founded startups, like Carbon...

How often does Lady Bosses (and Ben) release new episodes?

Lady Bosses (and Ben) has 8 episodes. Check the episode list to see recent publication dates and frequency.

Where can I listen to Lady Bosses (and Ben)?

You can listen to Lady Bosses (and Ben) on PodParley by clicking any episode. We provide an embedded audio player for direct listening, and you can also subscribe via your preferred podcast app using the RSS feed.

Who hosts Lady Bosses (and Ben)?

Lady Bosses (and Ben) is created and hosted by iHeartPodcasts.
URL copied to clipboard!