An Ode to Podcasting

Lessons learned from recording 500 podcasts

As a kid, I grew up listening to interview shows: Charlie Rose. Terry Gross. Howard Stern. Marc Maron. I couldn’t get enough.

I’d watch interviews with politicians, entrepreneurs, artists, everyone. I’d watch directors discuss films I’d never seen, authors talk books I’d never read, and comedians talk about standup routines I never watched.

The interview with the creator was always more interesting than the creation itself — why they did it; what they were trying to answer, prove, and share with the world.

Interviews showed me new vistas of possibilities — I saw a peek behind the curtain of thinkers and writers and artists and comedians and entrepreneurs who inspired me, putting myself in their shoes as I imagined doing what they did.

At some point in college, after being inspired by interviews of artists in different mediums, I dreamt of creating what I called a “mixed tape”. While a “Mixtape” in hip hop is a collection of free songs, I wanted to make a “mixed tape” — a collection of art projects merging different mediums: rap, prose, poetry, standup comedy, and, of course, interviews.

Inspired by this future, I wrote a possible future review of my mixed tape idea. So here I was, 19 years old, years before I had ever interviewed anyone, writing an extensive review of my own interview show, which had yet to be started. Here’s an excerpt:

“Erik Torenberg has the most interesting, intellectual, and personal interview show on the air right now. For almost thirty years years, Erik’s show has been a salon for extended, thoughtful, and honest conversation about culture, business, technology, politics, literature, entertainment, lifestyle, education, and any other topic that Erik wishes to explore.

He has interviewed everyone, from Bill Gates to David Brooks to Lil Dicky; He sometimes gets random people to freestyle — including Margaret Thatcher, Malcolm Gladwell, and the asian kid from School of Rock.”

In the 10 years since writing this, I have not had Margaret Thatcher, Malcolm Gladwell, or Robert Tsai, who played Lawrence (“Mr. Cool”) in School of Rock. But I have had a wide variety of interesting guests: I’ve asked Tim Ferris what he thinks about friendship and Esther Perel about relationships. I’ve asked Larry Summers and Donald Rumsfeld what they would do differently if they were still in office. I’ve asked Brad Feld about depression; Terry Gross about what makes a great interviewer; Tyler Cowen about a million things; and countless other people about what they changed their mind about, what they’d tell their 25 year old selves, and what they want to be said at their funeral.* 

Just as fun were giving people their first interviews, people like Kevin Kwok, Alex Danco, Byrne Hobart, Ani Pai, Dani Grant, and Jose Luis Ricon Fernandez de la Puente.

For me, podcasting has become a medium for self-discovery. In addition to learning more about the world, I’ve also learned a lot more about myself. I’ve gotten answers to the questions I wasn’t asking, all while learning many of the questions I was asking weren’t worth answering anyway. Maybe it’s my version of therapy. ;) 

In all seriousness, podcasting has significantly improved my personal and professional lives, and it’s something I’ll do for the rest of my life. It speeds up the learning cycle like nothing else, enables you to meet all these interesting people (guests), and it also helps you find more people who resonate with how you think (listeners). 

I say this all to say, if you’re curious about starting a podcast, you should! The best part about them is that just about anyone can have one — forget the fancy guests and equipment, all you need is a computer and a conversation topic you find interesting.

If one person starts a podcast because of this piece, I’ll consider it a success.

To me, you should start a podcast if you want to: 

  • Build a strong network and/or showcase your strong network  

  • Gain expertise and/or showcase your expertise 

  • Promote a specific topic or way of thinking

  • Attempt to satisfy your insatiable curiosity 

Podcasts are an amazing tool to build and strengthen relationships, both with your guests and your listeners. Not only do they act as your opportunity to openly “pick someone’s brain” in a way that’s helpful for them too, but they also create a bat signal to find other like minded people. Further, each interview is a forcing function to learn enough about a topic to not look dumb — podcasts are an incredible way to learn about topics you wouldn’t otherwise study. 

And while people don’t want to have “just another podcast,” I think we’re still in the early innings for podcasting. There are so many niches yet to be uncovered on which you could create the definitive podcast. The more niche the better —pick a topic where you can be the best in the world because of your unique perspective. Over 

time you can branch out, but starting a niche is the way to go in my opinion. 

Here’s some tactical advice I’ve picked up after 500 episodes: 

First, both you and the guest should prepare. I normally send out a preparation document about a week out from our recording date with questions, and ideally, you’ll have your guest write responses, if they’re up for it. Then you’ll edit the questions as needed.

Further, you should know enough about the person & topic that you can ask nuanced follow up questions — do this by asking other experts for questions as needed. Remember — a podcast is a performance; prepped is often better than improvised. 

(Speaking of performance, someone once joked to me that the reactions post-podcasts are similar to reactions post-sex — "How'd I do?" "Was that good for you?" "Did I talk too much?")

Jokes aside, you can ease any anxieties your guest may have by telling them they get final edit, your goal is to make them look great, and that, despite the prep, your conversation should be casual as if you were chatting over coffee. Also, if they’re eager to promote themselves, get it out of the way in the beginning so you have time to dive deep into the good stuff. (And you can edit it out if the promotion is too strong).

On the types of questions to ask, here are some examples of openers I like: 

  • When you look back on the arc of your career, what's the thread that ties everything together? What threads have you kept pulling? 

  • When you look forward to what you aim to achieve in the decades to come, what do you want your eventual wikipedia page to say? 

More generally though, instead of yes/no questions, ask open-ended & “double” questions. For example: “What do you believe about X and how has that evolved overtime?” is a much better question than “What do you believe about X?” (For the podcast guests reading this, view questions less as specific questions to be answered and more as prompts to say whatever's most interesting to you!)

On topics: Focus on a topic you have expertise in, no matter how niche (Remember, in building your personal moat the more niche the better!). Also, as you do more podcasts, try to invite high-signal guests that haven't done podcasts before — Byrne Hobart is a great example of this. On the other hand, if you have a famous guest, try to ask them questions they haven't answered before, like I did with Tyler Cowen here.

But aside from question format and topics, one of the best things you can do as a new podcaster is to set expectations with your listeners by being consistent: Release episodes on a regular cadence, and keep the timing of episodes the same. Reduce friction by giving your audience a clear picture of what to expect — if every episode is different, it will be hard to build a loyal following of like-minded people. 20VC’s Harry Stebbings is a master at this — he found his niche, timing, and cadence, and double & tripled down on it. Look where he is now!

Overall, don’t overthink it. You’re having a conversation with someone, the only difference is that you/they prepped, and it’s being recorded. You’re not signing up for a life time obligation to podcast, you can even start by just saying you’re doing one “season”. Announce you’re doing it on Twitter, get your first few guests, and then release them.

To that end, On Deck announced a podcast fellowship to up-level current podcasters and help new ones get started, led by Sachit Gupta who’s worked with Tim Ferriss and others. Whether you want to learn, build an audience, or build a business, the fellowship will set you up for success. It'll answer questions like: 

  • What should my angle be?

  • How do I manage the logistics?

  • How do I launch & promote it on iTunes?

  • How do I get great guests?

  • How do I grow my audience?

  • How do I monetize?

  • How do I ask better questions?

To learn more about the On Deck Podcaster Fellowship, visit our website here.

*= My first podcast, Maker Stories, was more focused on back-stories of the founders, investors, and creators. My current podcast, Venture Stories, dives more into the industries they represent.

Read of the week: The Authenticity Hoax

Listen of the week: Daniel Gross on Invest Like The Best

Watch of the week: Bitcoin is Fourth Turning Money

Cosign of the week: In addition to Sachit, Candice Ammori, who’s just launched On Deck Climate Tech and is a pioneering community builder in the climate space.

Until next week,