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What I unlearned about startups this year

December 11, 2021

Taylor Swift has impeccable timing. First, she released “Red,” an album about heartbreak and hurt, while I was in the thick of high school. My now-retired Tumblr is still thankful. More recently, Swift took on a project to rerecord her earlier albums, reclaiming her music from her old record label — this time with her own ownership as a key difference. Her first rerecording, of “Fearless” — annotated with “(Taylor’s Version)” — came out this year.

Of course, I think there’s a pretty obvious tech angle here. Swift made a statement on artist empowerment and the importance of singer-owned music — record labels be damned — the same year that we saw tech defined by the Great Resignation, emerging entrepreneurs and distributed work. Like Swift, I think the tech scene is going through an uncomfortable period of changing their minds, questioning authority and getting closer to self-advocacy as a result.

Looking back, I unlearned a lot about startups this year, especially when it comes to due diligence, formalization and what it means to be contrarian.

Due diligence is a differentiator

When Spark Capital decided to “sever all ties” with David Dobrik’s Dispo app weeks after leading a deal in the company, I immediately thought that it would set precedent across the venture capital industry. The move was triggered by a Business Insider investigation that exposed allegations from a woman who said that a member of Dobrik’s Vlog Squad sexually assaulted her.

In some ways, I was right: Unshackled Ventures and Seven Seven Six chose to step away from the company as well, donating any profits from their respective investments to organizations focused on survivors of sexual assault. In other ways, I was not. It’s clear that there continues to be a disconnect between what happened with Dispo and the world of fast-moving due diligence.

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