A famous startup investor had a DM fail and accidentally revealed his clever strategy for getting into super competitive funding rounds

Business Insider
  • In a self-proclaimed Twitter “DM fail” Wednesday, angel investor Jason Calacanis offered a currently unknown startup $US500,000 and time on his podcast, “This Week in Startups,” in exchange for equity.
  • Calacanis, an early Uber investor, opened up his pitch to his 301,000 Twitter followers after realising the post was public. He confirmed to Business Insider that he has received more than 30 emails and DM’s asking to take him up on his offer.
  • Calacanis is the founder of Launch.co, an early-stage venture capital firm that has previously invested in Thumbtack, Calm, and Robinhood.
  • Visit Business Insider’s homepage for more stories.

Tech investors have been known to offer all sorts of enticements and blandishments in the quest to win a deal with a hot startup. But angel investor Jason Calacanis has a unique incentive to dangle in front of startups: airtime on his podcast.

Calacanis, who rose to fame as an entrepreneur during the dotcom days, accidentally revealed his tactic on Wednesday when he tweeted what was meant to be a private entreaty to an undisclosed startup.

His pitch asked the unknown founder to reopen an oversubscribed round to allow Calacanis’ firm, Launch, to participate in the round. He wanted to invest $US500,000 in exchange for the typical equity, but also tried to sweeten the deal with the mystery entrepreneur by “guaranteeing” 1 million views from an appearance on his firm’s podcast, This Week in Startups.

Calacanis confirmed this was a “DM fail,” and decided to make the offer available to his 301,000 Twitter followers. Calacanis confirmed to Business Insider that he had received more than 30 emails and direct messages since the offer was made public Wednesday afternoon.

“My business is not underestimating anyone …. Love cold emails,” Calacanis told Business Insider, without saying whether any of the startups that reached out will be appearing on his podcast.

Calacanis’ firm focuses on early-stage investments in emerging technology companies. In addition to making an early bet on Uber, Calacanis and Launch have early investments in Thumbtack, Calm, and Robinhood. According to Launch’s site, the firm has seven companies in its portfolio that have been privately valued at or above $US1 billion.

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As for the startup that Calacanis originally offered a podcast appearance to, Calacanis won’t name the company or confirm whether or not the startup accepted his offer.

But he said “I wasn’t going to trade the podcast for the equity, that was the icing on the $US500k investment.”

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