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In the mid-1990s, a group of MIT students stunned casinos by winning extraordinary amounts of money playing Blackjack. These students, utilizing a data-driven card counting strategy, gained notoriety and became the subject of acclaimed books and films such as Bringing Down the House and 21.

One of the team members, Jeff Ma, went on to become a 4x founder and an executive at Twitter before joining Microsoft as VP of Startups. Jeff joined hosts Scott and Andrei to describe his key learnings from building and exiting several successful companies. The conversation covers misconceptions around funding as an end goal, aligning perspectives between enterprises and startups, and the most exciting areas in tech.

Here are some quick takeaways:

  • Aligning perspectives to avoid friction should be the first consideration when entering a partnership.
  • When partnering with an enterprise, startup founders often underestimate the sheer scale that they are dealing with- fully utilizing their resources is not a trivial task.
  • The size of large enterprises can hinder the rapid implementation of initiatives; however, it also makes accomplishments more rewarding.
  • Starting a company with the hope of being acquired is the wrong mindset.
Andrei Newman

Written by Andrei Newman

Andrei Newman leads Product Marketing at Troops.