Looking For A Mentor? Try Gimlet Media's 'StartUp' Podcast

“Any time you feel a pit in your stomach, pull out your phone and record the moment.” That’s the request Lisa Chow, co-host of the podcast StartUp, made to the founders of the company she followed in the show’s second season.

According to Chow, StartUp “Delves deeply into people’s feelings about the ups and downs of starting, running, and managing a business.” The result is exceedingly compelling. As a business owner myself, it’s also cathartic – I call the StartUp podcast the ultimate mentor and therapy for entrepreneurs.

As they gear up for Season 5, launching April 14, here are four of my biggest takeaways from the show:

1. It made me feel less isolated.

When I first started my business, I had very few friends who were entrepreneurs, and none of them were women. The women I knew who worked for themselves didn't see themselves as entrepreneurs. They identified more as consultants, locked into the amount of money they could make based on the hours they worked.

Via StartUp, I heard entrepreneurs (male and female alike) grapple with issues of work-life balance, the roller coaster ride of cash flow and the bizarre experience of naming a business. At a time when I hadn’t yet found my network, it was deeply affirming to relate to the challenges and successes StartUp described.

2. It helped me deal with the imposter syndrome.

In Season 1 of StartUp, we follow Alex Blumberg – co-creator of Planet Money and alum of This American Life – as he starts the podcasting business that eventually becomes Gimlet Media, the podcast company that produces StartUp. (It’s very meta.)

Blumberg describes the show by saying it’s “the business story you never actually get to hear, set down before the facts can fade into sunny startup mythology. It’s the most honest and transparent account I can make of...starting a business.”

Hearing this middle-aged man whose company recently raised $6 million in venture funds struggle openly with self-doubt and apprehension felt powerfully grounding. To hear Blumberg dealing with the imposter syndrome didn’t make him less of an entrepreneur. Instead, it humanized him and, in the process, normalized those same feelings for me.

While I still have moments of self-doubt and questioning whether I’m cut out for this, I feel far more confident calling myself an entrepreneur because of this show.

3. It showcases women who are driven to attain professional success.

I still remember the first time a female entrepreneur friend told me, “I want to make a lot of money.” It almost felt transgressive to me for her to say aloud. As women we’re socialized to be concerned about others, be collaborative and never self-promote, and that can be a hard thing to override. In my circles, while we talked about women’s empowerment, it was still usually with the lens of being of service.

I’ve taken to saying, “I want to make a lot of money” myself, and it still feels a little liberating each time, particularly as someone who was taught to be of service first and think of myself second.

In Season 2 of StartUp, Dating Ring co-founders Emma Tessler and Lauren Kay strive to achieve an audacious professional goal. While I don’t recall an instance where they prioritize money as a key factor in launching the business, they’re also young professional women aspiring to a level of success that would come with considerable financial gain.

By focusing on Tessler and Kay, StartUp effectively normalizes female entrepreneurship and professional success. It’s refreshing and inspiring to hear Tessler and Kay tell their story in their own words, upspeak and all.

4. It shows how to define “success” for ourselves.

At the beginning of Season 2, we meet Tessler and Kay as they go through Y Combinator, the prestigious incubator. They’re seeking investors to fund what they envision to be a high growth company that would revolutionize the dating world, becoming “the Uber of the dating industry”.

Later in the season, we hear Tessler and Kay accept that their original vision no longer feels realistic. It was an instructive reminder that starting a business is an iterative process and that success can be a moving target.

In the moments when I change my pricing structure or adjust my own business model yet again, I remember having been a fly on the wall for Tessler and Kay’s process. I recall the ways they describe fears of failure and grappled with internal conflict, how they redefined success and embraced becoming a lifestyle brand in lieu of the high-growth startup they’d worked so hard to create. It serves as a healthy reminder that I get to define success on my terms, and that those terms can change over time.

As Chow describes it, part of entrepreneurship is constant self-promotion, which can make it difficult to have the honest conversation about what’s really under the surface – the kinds of conversations you’d want to have with a trusted mentor. StartUp created something magical in this podcast: a form of powerful validation and connection via these vulnerable, raw stories of entrepreneurs.