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Libsyn’s Acquisition of AdvertiseCast: The Tell-All

In 2016 Trevr Smithlin and Dave Hanley founded AdvertiseCast, a marketplace connecting podcasters with advertisers. The company experienced tremendous growth, doubling revenue year-over-year until 2020.

That’s when the uncertainty triggered by the COVID-19 pandemic caused Smithlin and Hanley to consider their strategic options.

In March 2021, Smithlin and Hanley signed an acquisition agreement from Libsyn for $30 million.

In this episode, you’ll learn how to:

  • Build a strong relationship with your co-founder.

  • Retain top talent using a counterintuitive approach.

  • Ensure your business can thrive without you.

  • Utilize an unconventional sales strategy to establish trust with a prospect.

  • Employ a crafty negotiation tactic to increase an acquirer’s offer.

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More About Trevr Smithlin and Dave Hanley

Trevr – Former CEO & Co-Founder of AdvertiseCast acquired by Libsyn (stock symbol LSYN) 2021. Now Head of Podcast Partnerships and Chief Innovation Officer at Libsyn.

Dave – As a member of three founding teams, Dave has been instrumental in building three bootstrapped technology companies into sustainable, profitable industry leaders. Former Co-Founder of AdvertiseCast, currently Chief Revenue Officer at AdvertiseCast.


Earn-out: Earnout or earn-out refers to a pricing structure in mergers and acquisitions where the sellers must “earn” part of the purchase price based on the performance of the business following the acquisition. Source.

Due-Diligence: Due diligence is an investigation, audit, or review performed to confirm facts or details of a matter under consideration. In the financial world, due diligence requires an examination of financial records before entering into a proposed transaction with another party. Source.

Letter of Intent (LOI): A letter of intent (LOI) is a document declaring the preliminary commitment of one party to do business with another. The letter outlines the chief terms of a prospective deal. Commonly used in major business transactions, LOIs are similar in content to term sheets. One major difference between the two, though, is that LOIs are presented in letter formats, while term sheets are listicle in nature. Source.

Preferred Preference: Preferred Preference means that amount equal to the sum of the Preferred Preference Per Share for all shares of Company Preferred Stock (including any rights convertible into, or exercisable or exchangeable for, shares of Company Preferred Stock on an as-converted, exercised, or exchanged basis) issued and outstanding immediately prior to the Effective Time, rounded to the nearest one hundredth (0.01) (with amounts 0.005 and above rounded up). Source.

Waterfall: A distribution waterfall describes the method by which capital is distributed to a fund’s various investors as underlying investments are sold for gains. Essentially, the total capital gains earned are distributed according to a cascading structure made up of sequential tiers, hence the reference to a waterfall. Source.

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