Podcast To Listen To in 2019: For Entrepreneurs, Founders, Solopreneurs and Bosses

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One of the most-asked questions I get from the tech and start-up community is about podcasts: which ones to listen to and what episodes to start with. As someone with a lengthy commute, I accumulated a list of go-to shows about all things entrepreneurial, techy, and start-up-centric. In no particular order:

How I Built This

Hosted by Guy Raz, HIBT is a show about the stories behind some of the world’s biggest companies. Each episode is a stand alone interview, so you can jump around. HIBT is great because you get a true sense of how much time and work goes into building these huge household names, and an even better sense of how close some of them came to failure. My favorite episodes are the interview with Richard Branson, founder of Virgin Group and the interview with Sara Blakely, the founder of Spanx (Sara also has a killer Instagram feed, she is hilarious if you want to check that out).

Skimm’d From The Couch

The latest offering from TheSkimm empire, is Skimm’d From The Couch, hosted by the co-CEOs and Co-Founders Carly Zakin and Danielle Weisberg. Together, they interview inspirational leaders and do a full career shakedown - from the best days to the absolute worst and dissect their path to success. Like HIBT, each episode is an interview so you can pick and choose episodes without getting lost. Occasionally they sub in episodes called “Founder Chat”, where the host answers questions, to mix things up. I love tuning into this podcast because it’s so real and relateable (even if you’ve never founded a company). They have a strict no BS policy and it leads to some interesting conversations. My favorite episode was their Founder Chat on turning your side hustle into a business.

The Pitch

The Pitch takes you deep into start-up land with Josh Muccio from Gimlet Media. This show is basically the podcast version of Shark Tank, with a little extra. Each episode a CEO pitches to a panel of investors with the hopes of exchanging some equity for a check. Anyone who has ever pitched themselves, their company or a product can relate to these episodes.

I like this show (even the cringey bits) because 1) listening to other people pitch makes you better at pitching, 2) you hear ALL THE QUESTIONS investors ask, and maybe catch one you hadn’t thought of before and 3) you get to hear about all the startups and tech that not quite on the market yet. Josh follows up with the start-ups after the pitch (sometimes months after) to see how things turned out. My favorite episode so far is Sophia Dominguez’s pitch for SVRF. Sophia and I did an accelerator together and her episode keeps you guessing until the end.

StartUp

Another Gimlet Media podcast, actually the original Gimlet media show, StartUp, follows nascent companies through their early days at that pivotal time when they either get traction and “make it” or fizzle out. Each season StartUp follows a new company, so you really need to listen to episodes in order, although you can start with any season. This show is so good because you get to hear all the conversations you would never normally hear: between co-founders, between the founders and investors, equity negotiations, deciding on a name, the 2am phone calls about quitting and moving to Guam. You know, all the good stuff. If you’re thinking of founding a company, give it a listen you can learn a lot. If you’ve already founded a company, give it a listen, you’ll say “omg, this totally happened to us,” at least once an episode. My favorite season is season one, which is about the founding of Gimlet Media itself (very meta), hosted by Alex Blumberg.

GaryVee Audio Experience

You will either love this show, or completely despise it. It actually took me three tries before I got into this one. Gary Vaynerchuck, the CEO of VaynerMedia churns out an unbelievable amount of content about branding, marketing, culture and a touch of the motivational/inspo rhetoric. Each episode stands alone, so you can skip, scroll, and jump around. Episode range from hour-long interviews (usually titled “Ask GaryVee”), to five minute airplane rants, to 90-minute keynotes, and the occasional compilation.

This show has great guests, and as someone who is not particular dialed in on pop culture, it makes me feel like I have some sense of what going on in art, music and social media. VaynerMedia is also a pioneer in digital-first marketing and branding and anyone who needs to marketing a company or themselves can get tangible takeaways from this show. There are so many episodes, I don’t really have a favorite so the most recent on is embedded below.

BoostVC Podcast

The Boost VC podcast, hosted by the founder of Boost VC, Adam Draper, is a show about sci-fi tech, in real life. They interview founders (often from the Boost VC portfolio) on topics like cryptocurrency, startup strategy, virtual reality, AI, JET PACKS, exoskeletons, drones, and space. Each episode is an interview, so you can listen in any order. This show is great because you can learn about all the emerging, sci-fi adjacent technologies, from the founders themselves, and see how they are all interacting. Did I mention they have jet packs? My favorite episode was the interview with Esteban Ordano, founder of Decentraland, where Esteban explains how cryptocurrency can help solve problems in VR.

a16z

The a16z Podcast is produced by Andreessen Horowitz (aka “a16z”), a massive Silicon Valley venture capital firm that has backed many of the companies you know and love. Hosted by an a16z operating partner (Frank Chen in the episode below), each episode discusses tech trends, start-up news, and the future. Each episode is an interview, usually with a panel of experts, industry leaders, thought leaders and founders, so you can download episodes in any order. The multiple guests can get confusing, but overall doesn’t detriment the takeaways from each show.

a16z is like the Associated Press of tech podcasts. It may not be the most entertaining show you’ve ever heard, but you walk away feeling informed and knowledgeable (which is a bit of a theme here). My favorite was one recently on tech trends.

Freakonomics

One of the first podcasts I ever listened to, Freakonomics is still a mainstay on my podcast app. Hosted by Stephen J. Dubner, he sets out to “Discover the hidden side of everything”. Each episode is a reported piece where Stephen interviews entrepreneurs, academics, laureates, authors…and various other people with impressive CVs. They occasionally do series (see below), but generally you can listen in any order. Going from the title, you might not peg this one for an entrepreneur/tech show, but anyone who is in the business of problem solving (i.e. anyone who has turned an idea into a product), will appreciate the, often hidden, economics of, well, everything, from politics to creativity. My favorite episodes were the one in “The Secret Life of a C.E.O.” series

Women In Business & Technology

Started at Microsoft WIBT and host by Colleen O’Brian and Sonia Dara, this podcast showcases prominent leaders, movers and shakers and game changer in business and tech roles. They also cover workplace inclusion programs.

Each show is broken up into segments. There is usually one in-depth interview, a news pieces and some shorter, snappier interviews. You can listen to shows in any order. This podcast is great for finding leaders and role models to follow as well as gleaming some concrete strategies for building a career in the tech industry, no matter what stage you are at. My favorite episode is #32, WorkPartying with Create & Cultivate. *My company, Future Sight AR, has a tiny shout out on the episode, so I’m a bit biased; HOWEVER, it is still a great episode and Create & Cultivate Founder Jaclyn Johnson has a great start-up story that she shares.

Have a show I should add to the list? Let me know!