Why this powerhouse VC chose a ‘Bachelor’ to co-host her podcast for women

Jesse Draper and Ben Higgins have launched a podcast to help and highlight female founders called “Lady Bosses (and Ben).”

Jesse Draper is a venture capitalist legacy. Her father is Tim Draper, a partner at Draper Fisher Jurvetson, and her grandfather, as well as her great-grandfather, were also in the business. But don’t think she is riding on anyone’s coattails. Her family may have sparked her interested in investing in industry disruptors, but she has turned it into something incredible with Halogen Ventures, a VC firm primarily focused on female founders. Her portfolio includes The Skimm, Carbon38, Sugarfina, and Finery and in December of last year, they closed their first fund at $10.4 million.

But in addition to giving them the funding to bring their companies to new levels, she also wants to highlight these women and give them a voice. That is why she decided to start a podcast primarily focused on women founders. Draper is a lover of podcasts but found there wasn’t one program out there doing this.

“There’s not a lot of women in business opportunities on podcasts. There’s a lot of technology-oriented ones with a lot of men and I just wanted a great place to feature women in business,” she told Ladders. “There’s a couple I listen to but none that were giving me what I wanted.”

It has been widely reported that female entrepreneurs struggle much more than men when it comes to raising money. Investment rounds in startups with all-male founders in 2017 outnumbered female-led companies by a ratio of more than 18 to 1, according to data PitchBook Data Inc.

So clearly a show like this has a need and an important purpose. But who to select for a co-host was the main question? Perhaps another female VC or entrepreneur but Draper decided to go in a different direction. One that was towards everyone’s favorite guilty pleasure: The Bachelor. Ben Higgins, who was featured on ABC’s The Bachelor in 2016, did date upwards of 30+ plus women at the same time, take romantic helicopter, horseback and other various romantic animal and automobile rides, and broke many a heart at a rose ceremony, but he also is the co-founder and President of his social enterprise Generous Coffee.

Generous is a  “for-purpose” business which means it uses profits to fund operational expenses of nonprofits or social enterprises that are doing sustainable, helpful work all over the world. In other words, he is not just living off his television fame and selling things on Instagram. He is trying to make a difference.

And he is all about women, which is why Draper was drawn to him to help her launch this project.

“Who better to do it with then someone many women love? He is very social and enterprise focused. We come from very different backgrounds and have very different perspectives on the world but we are both looking to elevate women so I’m really excited to do this with him. There’s no way you could love him more now!” Draper said.

The podcast is called “Lady Bosses (and Ben)”, and is produced and distributed through iHeartRadio. Each week, they’ll sit down with a different CEO, entrepreneur, or business mogul and learn how they achieved their goals, what challenges they face building a company, and the tips they can share with the next generation of business leaders. Upcoming guests include Brooklyn Decker, founder of Finery, and Alli Webb, the founder of Dry Bar. “You will hear a lot about women in business and women just juggling it all,” said Draper, who is a mother of two young children. “It’s really hard, How do you make it work? It’s a real business show.”

She recalls talking to Decker about the experience of fundraising while pregnant. “Those are real conversations that are cool and different to think about,” she said.

Meredith Lepore|is the Deputy Editor of Ladders and can be reached at mlepore@theladders.com.