This Columbia Business School Alumna Tells It Like It Is

When COVID-19 hit the UK and the country entered lockdown, Cassandra Rae Pittman was in the beta-testing phase of her new startup, Soapbox, a workplace-review site for women, by women. After making the difficult choice to pause the company’s launch, Rae Pittman was driven to find another outlet for amplifying women’s voices.

That outlet became her podcast, Tell It Like It Is, where she has candid conversations with entrepreneurs about the nuance of being a female leader in the business world.

While the podcast began as an eight-episode passion project, it has quickly gained momentum and fans, proving that listeners are hungry for open conversations with women in business.

Below, Rae Pittman explains how her project came to be, what she’s learned so far, and what’s next.

You mentioned that you don’t have a background in podcast production, so how did Tell It Like It Is come to be?

Less than a year ago, I started working on a startup called Soapbox, which was set to be the UK’s first workplace-review site for women and by women. Our goal was to empower women to make decisions about their careers using real-life insight from other women who were already working in the target organizations. We were in the beta stage and had big plans to launch this summer. Then, COVID hit, and with that came funding issues, talent issues, and market issues. At this point in time, people are rightly really grateful for their jobs, and we didn’t feel it was the right time to move forward. I was disappointed to have to shelve Soapbox, so in lockdown, I was itching to do something to advance the mission. I had this idea for a podcast, and it started with my ordering a second-hand microphone off of (from) Amazon. I planned to talk to some amazing women, to make eight episodes, and if no one listened, at least it would feel like I was doing something of interest to me. Since then, it’s taken on a life of its own.

What was missing in the content that already existed on professional women that made you want to start your own podcast?

In a word: nuance. We live in a time where if you can’t say something in a 280-character tweet, it doesn’t get said. I think that drive for oversimplification does a disservice to every topic out there. It’s alienating to see profiles that seem perfect, or that have an effortless arc of a leadership journey – “I started out, I had a problem, I overcame the problem, and now it’s wonderful.” That’s not how real life works and that can shame women. For example, the conversations about self-care, which are all the rage right now, sometimes make me feel like a failure. I don’t have time to do an hour-long yoga session; most days, I don’t have time to do 10 minutes of yoga. In lockdown with a two-year-old, I had to reinterpret what self-care meant for me at that moment.

Have any trends emerged from speaking with these women?

Yes. I started talking to people in lockdown, so I was speaking with women who were facing a unique set of challenges. I think that the work-life balance has changed for a lot of women in this time, especially if they have kids, because they’re having to juggle homeschooling and childcare on top of everything else. Not that I want to center every ‘women in business’ conversation around children – that’s totally off-putting to some people and is a trope that’s well discussed already. Nevertheless, statistics bear out that this has been a very challenging time for many women. To date, every woman I’ve interviewed is an entrepreneur of one variety or another. It’s an open question I have as to whether or not women who are still working for an employer feel free to have open, nuanced conversations about the good, the bad, and everything in between. My hypothesis so far is that the reason I’ve had mostly entrepreneurs on the podcast is that they feel free to say what they like, since they’re running their own thing. And I think that says something, because I don’t think we can really move the needle where we need to move it unless we can have a really open dialogue about our lives. I’d like to know more about that by talking to women who aren’t striking out on their own just yet.

Do you plan to continue the podcast? Where do you see it going in the future?

There’s enough media out in the world filling up space. So as long as these conversations are valuable to me and to others, I want to continue to have them. So far, I’ve been talking to women who are entrepreneurs, but I have a couple of women lined up who are more involved with politics. Women being underrepresented in business is only the half of it! Power needs democratizing in education and politics too, and I’m excited to expand the set of people I talk to in order to gain insight into this. One thing I’m obsessed with is not just promoting women in business – although that’s a really important part – but really advancing women into positions of power in every sphere, because they are underrepresented in every sphere. So I am really interested in expanding the set of people I talk to into more sectors of power. Two upcoming interviews I’m super excited about are with Diane Morales, the Democratic primary candidate for New York City mayor, and Tara Setmayer, who is one of the advisors to the Lincoln Project and a CNN political commentator. I’ve been a Democrat my entire adult life, and most people in my circle – especially in the UK, which leans further left – think pretty much like me. So I’m really interested to talk to a woman like Setmayer who has been a lifelong Republican and thinks differently than I do about a lot of critical things, but with whom I can also see a lot of shared values. It’s by having these sorts of conversations that I hope real change will happen.

Sara Cravatts is a writer, editor, and producer based in New York City. She currently writes for Columbia Business, the alumni magazine of Columbia Business School.

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