One Big Bet in 2009 Changed Podcast Advertising

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Our Valentine’s animal this year is the gray wolf, a species that often mates for life. (Last year’s North American river otters sure captured some hearts.) XOXO, PM Daily

PodMov Daily: Monday, February 14

Episode 589: Your Monday Mix

One Big Bet in 2009 Changed Podcast Advertising

In 2009, Squarespace founder Anthony Casalena took a $20,000 gamble: an ad on the podcast This Week in Tech. “It was so expensive compared to anything else I had done,” he told Joel Stein of The New York Times. Podcasts paid off, many times over. Yesterday Squarespace ran an A-list celebrity ad during the Super Bowl.

The return on investment was so enormous that by 2015, the company was taking out two-and-half as many ads as its nearest competitor, Stamps.com. Stein gives a behind-the-scenes look at how the industry responded, including an internal meeting at Midroll about one brand representing a third of revenue.

Squarespace is still made fun of for its ubiquity on podcasts (popping up on “Saturday Night Live” and elsewhere), but Casalena enjoys the attention. When the $6.6 billion company went public in May, he landed $2.4 billion in stock. Today, his product strategy is based on a decentralized economy — “all side hustle, all the time.”


The Struggle to Capture Great Podcast Storytelling

For five years, Julian Shapiro wanted to start a podcast to exchange stories with great storytellers. But, he admits, “every time I recorded a test episode, I sounded lifeless like a stressed-out amateur.” If you’re concerned about the impact of your delivery behind the mic, here’s some recommended reading.

Shapiro is a writer, marketer, and developer with a passion for learning from his own failures. During his “treasure hunt” for what makes a compelling story, he did what many podcasters set out to do at the beginning. He studied masters like Neil deGrasse Tyson on YouTube — and continued to record episodes that flopped.

What finally struck gold was the concept of “blowing your own mind.” (Sounds goofy, but it’s not.) Shapiro finds that while strategy and practice are important, the key is to truly relive what we’re telling. Audiences feed off emotion in critical moments, the same ones that make a story worth repeating.

Podcast Parties: Turn Your Audience Into a Community

When podcast fans spend time together, they become more than just an audience – they form a community. Podcast Parties is a new full-service virtual event production company built just for podcasters. Whether you’re launching a new season or hosting an educational workshop, it’s the easiest way to bring your fans together.

Podcast Parties will help you design your event, promote it, sell sponsorships, and give your fans an experience unlike any other. Podcast Parties go far beyond Zoom meetings by giving your listeners a unique opportunity to mix and mingle at virtual tables.

Virtual events can open new revenue streams through ticketing, sponsorships, subscription perks, and more. Ready to see the platform in action? Schedule a demonstration to get the party started.


We are cups, constantly and quietly being filled. The trick is, knowing how to tip ourselves over and let the beautiful stuff out.

Here's what else is going on:

  • Score card: The third annual “Super Listeners” study will be presented this Wednesday by Edison Research and Ad Results Media. How have attitudes toward podcast advertising changed among the heaviest listeners (5+ hours weekly)? The webinar begins at 2:00 pm ET. Free registration.
  • Power up: This Wednesday at 1:00 pm ET, Podcast Audio Lab founder Marcus dePaula will lead “How to Get the Best Sound with the Tools You Already Have.” The webinar and Q&A from Podcasting, Seriously will cover equipment, techniques, and home recording solutions. Tickets are $33.50.
  • Flow state: “I’m sorry to interrupt…” is Andrew Warner’s favorite phrase when interviewing. The Mixergy creator suggests a few polite phrases to ‘cut in’ without derailing the other person. Guests appreciate it too: “I just want to keep our conversations focused on solving the listener's problem.”
  • Access granted: This Wednesday at 4:00 pm ET is “Reaching Out to Grant Makers” from Podcasting, Seriously. The organization’s weekly Twitter Spaces meetup features guidance from Juanita Islas, Director of Programs for the International Women's Media Foundation. No account needed.

Brennan Tapp

Brennan is the Managing Editor of Podcast Movement. As the PodMov Daily newsletter czar, she is probably reading or writing at this very moment. Her career has spanned scientific research, academia, and fashion, with clients including The Neiman Marcus Group, Belo + Company, Baylor Scott & White, and Thomson Reuters. She’s glad to have found her home in podcasting and highly recommends "The Memory Palace," which is best listened to on a night drive. She lives in Dallas with her cats, Sushi and Simon.

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