Podcasting 201: Going pro with Should We

Spilling a whole new bag of beans about how we went big with our podcast, Should We

Diana Kimball Berlin
Should We

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Last June, Lisa and I published a guide to making a podcast on a budget of zero. Since then, a lot has happened. First, we raised over $10,000 on Kickstarter to make season 2. Then, we launched season 3 with the support of our Patreon backers and our season sponsor, MailChimp. Long story short, we actually tried—in a big way.

This is us! We hosted a live show at Slack HQ in May 2017.

Along the way, here’s what worked for us.

Crop from the cover of one of my favorite books circa kindergarten. It was a parenting handbook (really).

Identity

Investing in our identity is one of the best decisions we’ve made. We partnered with design studio Math Times Joy to develop a bold, colorful, and flexible visual identity for Should We. Thanks to Celeste and Rob, we’re set up with a logo, a color scheme, and a style guide that can support us going as big as we want. We recently did a short-burst project with MTJ to design enamel pins for our first live show, and were delighted by how simple it was to move fast thanks to the foundation we’d built together.

Glamour shot of enamel pins designed by Math Times Joy, straight from Should We’s Instagram.

Recording studio

We went into season 2 thinking we’d upgrade from recording on an iPhone to using a Blue Yeti mic with a foam desktop sound shield. We soon found that the sound quality still wasn’t so hot, and we suspected it had something to do with the rooms we were recording in. So, we started poking around San Francisco to see if we could find a recording studio that was in our budget. Miraculously, Faultline Studios—the first studio we tried—turned out to perfectly meet our needs for nearly a year.

In summer 2017, Faultline closed up shop, so we went on the hunt for another recording studio. We found Women’s Audio Mission, which we adore. It’s a non-profit dedicated to “changing the face of sound,” and their studio space in the heart of SOMA, San Francisco, is gorgeous. For a five-hour recording session, they charge $45 an hour.

Women’s Audio Mission in the heart of SOMA, San Francisco. Not shown: colorful guitars lining the walls.

Transcripts

For all of season 2 and most of season 3, transcripts were a key part of our production workflow. We’d go to the studio, record an hour of audio, then get the raw audio transcribed. Afterward, Lisa and I would use Quip to collaborate on a cut list that took the episode length down to about half an hour, then send that cut list to our sound engineer, who would take it from there and upload the final audio file to Dropbox. The transcripts didn’t need to be perfect—just good enough to remind us of what we said when, so that we could line up the cuts with timestamps.

For season 2, we used Rev.com—transcription done by humans, at about $1/minute with 24-hour turnaround. For season 3, we followed our friend Luisa’s recommendation and gave Trint a try. Automated transcription starting at $12/hour! It met our very basic needs, and was a real game-changer in terms of bringing down our per-episode costs.

For the second half of season 3, which we just kicked off, we decided to start sharing uncut episodes as a matter of course. Love notes from our listeners persuaded us that the realer we are, the happier they are—and part of being real is letting our conversations unfold naturally and sharing them in full. As a bonus, skipping transcripts brings our production costs down slightly. But we’d happily return to using Trint if we thought it would be helpful.

Theme music

Finding a theme song was a real challenge, particularly since we knew we’d need permission to use any we found. After digging deep into the intersection of “artists we could contact” and “songs that made sense for Should We,” we came up with exactly one—“Hey Garland,” by Canada. Fortunately, Canada’s cellist was my internship manager about a decade ago, and all the rights to the album had reverted back to the band. She was able to get her bandmates’ blessing for us to use the song as our theme music for the intro and outro of each episode.

LLC

Lisa and I decided that doing all the paperwork to set up a business was part of the whole experience. (And prudent, besides.) We did our research and set up a California LLC.

Studio space

Three things happened at once in the fall of 2016: our backer reward merch piles had become unwieldy, the list of people interested in my leadership coaching practice was growing, and I realized that having a creative space separate from my apartment was one of my fondest dreams—and worth a try. So, I found a room that we could rent by the month on a site called Pivot Desk, and we haven’t looked back. We meet with clients and collaborators there, hold our quarterly partner summits in the space, and use it for all kinds of creative work. It’s full of light and focus.

Should We’s San Francisco studio space, featured on Instagram

Software and online tools

Collaboration and asset production: Aside from Trint for transcripts, we’re deep into Quip, Slack, and Dropbox. Quip for project management, newsletter drafting, and episode cut list collaboration. Slack for maintaining dozens of chat convos with each other in parallel, each one with its own topical channel. Dropbox for episode art and audio files. I work at Quip, Lisa used to work at Dropbox, and Slack hosted our live event; we feel warmly toward all three. We also use both Adobe Illustrator and Sketch—Illustrator to tweak episode art templates created for us by Math Times Joy, Sketch to create our own artwork from scratch. (Specifically, the digital wallpaper collection for our Patreon backers.)

Funding: Having used both Kickstarter and Patreon, we can strongly recommend both. Kickstarter is great for getting going and unlocking big bang possibilities. (I also happened to have a blast interning there in the summer of 2012.) Patreon is ideal for the marathon, the long haul; I’ve loved writing each note to our patrons there.

Publishing: MailChimp has grown with us in a wonderful way, both as a sponsor—supporting us in season 2 and season 3—and as a toolkit: we started with TinyLetter and have since graduated to MailChimp proper. For our website, Math Times Joy set us up with Squarespace, which we’ve been very happy with. For hosting our audio files, we use SoundCloud—another place I once worked! And social media-wise, we’re on Twitter, Facebook, and Instagram.

Growth

Lisa and I love making Should We. It’s so gratifying to step into a recording studio, spend a chunk of time being our realest selves, then share those conversations with the world. The biggest question for us has been “how do we find even more of our people?” Our audience has steadily grown, but we haven’t yet found a silver bullet for hockey stick growth in podcast land.

An email exchange with Julie Shapiro, executive producer of Radiotopia, helped to give us some perspective here. I met Julie at an unconference held at Kickstarter last year, and I followed up with a link to Should We and some questions about the best ways to grow. She outlined a few ideas, then wrote:

I definitely think that getting involved with other makers, going to conferences, finding listening parties, why not start a listening party… all of that helps in building momentum and growing your audience. Depending on what your ambitions are with this show, all of that is super important, and definitely more fun when you’re doing it within a community.

This was our wake-up call: there’s no fast track to true (listener) love. And since true love is what we’re after, we decided to double down on what we were already doing—creating episodes, connecting with listeners, and sparking friendships by bringing people together in person, as we did at our live show at Slack HQ in May.

Next

We’re sharing our story because we want more stories like ours to exist. In Lisa’s words, “experimenting with a totally new medium (podcast) helped us (two writers who’d rather talk) develop our voices and get our message out in a way that (surprisingly) turned out to be easier and more fun than writing.” We want everyone to find their message, their medium, and their own surprising truth about speaking up. What will yours be?

Find Should We on Breaker, and rummage through the archives on our website. Beyond our podcast, Lisa and I both offer leadership coaching; you can snag a sample session with either one of us.

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Early-stage VC at Matrix Partners. Before: product at Salesforce, Quip, SoundCloud, and Microsoft. Big fan of reading and writing. https://dianaberlin.com