A few weeks ago, our show carried a special announcement that On Deck had raised a $100 million fund to fuel the next generation of entrepreneurs. Swapstack, cofounded by Jake Singer & Jake Schonberger, is the first company to be accepted into an ODX cohort and receive a check for $125k check from the fund.

Swapstack is positioned to be the premier newsletter advertising marketplace, connecting brands with writers to help the latter be able to become full time creators. The inbox, as the Jakes claim, is an intimate space. Newsletter creators want to make sure that they choose advertisers that align with their content so as to not pester their audience and risk losing carefully cultivated trust.

This was a well timed conversation. It follows our discussion with Josh Kaplan about Creator Operators and builds off of last month’s discussion with Nathan, who runs a newsletter bundling company. We get into the nitty gritty of the newsletter business specifically. Swapstack wants to build the backbone for creator monetization and is well timed to assist a booming newsletter industry. We chat about the incentives of feed-based ads, how paywalls can lock creators into a restricting cadence, and about the metrics that matter most when writers are first getting started.

In addition to sharing a first name, both Jakes also are former On Deck employees where they were working on Swapstack as part of On Deck's creator offerings. Through that lens, we chat about intrapreneurship as both Jakes are able to lean on past innovative experiences they have had at other tech companies, including Facebook and Amazon. For more information about ODX, please visit beondeck.com/x

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