Monetizing Podcasts and Newsletters – Chris Best of Substack and Jonathan Gill of Backtracks

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Chris Best is the cofounder and CEO of Substack. Substack makes it simple for a writer to start a paid newsletter. They were in the Winter 2018 batch of YC.

Jonathan Gill is the cofounder and CEO of Backtracks. Backtracks is a podcast analytics and hosting platform. You can check them out at

The YC podcast is hosted by Craig Cannon.

Y Combinator invests a small amount of money ($150k) in a large number of startups (recently 200), twice a year.

Learn more about YC and apply for funding here:



00:00 – Intros

00:25 – Paid vs advertising in podcasting

2:55 – Are advertisers overpaying for podcast ads?

5:35 – What percent of the market will ultimately be paid content?

7:35 – Payment mechanisms

9:10 – Price anchoring

11:50 – Individual creators vs brands

16:45 – Deplatforming

18:15 – Spotify

19:45 – Discovery and growth in newsletters

22:05 – Public and private feeds

24:45 – Apple’s role

26:00 – Will education be the driver of paid content?

29:45 – Educational podcasters in China

31:45 – How are their newsletter and podcast customers growing?

35:40 – Jack Ryder asks – In 5 years time, are personal newsletters going to replace social networks like Facebook?

37:35 – Debdut Mukherjee asks – Do podcasts actually work? If so, how do startups calculate the ROI & the CAC?

43:00 – Measurement

44:45 – Best practices for new podcasters and newsletter creators

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