20VC: The Largest Venture Backed D2C Consumer Exit; PillPack: $0-$300M Revenues in 5 Years & The Biggest Lessons Scaling the B2B Business to $300M in 2.5 Years with TJ Parker, Co-Founder @ PillPack

TJ Parker is the co-founder and former CEO of PillPack. TJ Raised over $100M in financing, grew the company to more than 1k employees, and successfully sold the business to Amazon for $1B in 2018. As of last week, TJ was announced as the newest Partner @ Matrix Partners where he will initially focus on health opportunities from concept to series A.

In Today’s Episode with TJ Parker We Discuss:

1.) From Growing Up in Pharmacies to Selling to Amazon for $1BN:

• How did TJ seeing the pharmacy industry from his parents lead him to believe there was a $BN company to be built in the space?

• What does TJ know now that he wishes he had known when he started the company?

• What does TJ believe he is running from? How does that impact his own style of parenting?

2.) The Truth About Entrepreneurship:

• Why do the best founders have to get comfortable in an environment of uncertainty? What have been some of TJ’s biggest lessons in how to do this?

• Why does TJ believe the role of the CEO is to set the vision and get out of the way? What roles can only the CEO do? How does TJ approach delegation? What have been some of his core lessons?

• Does TJ believe being naive is a superpower when starting a company? What do founders need to know vs what do they not need to know when starting a business?

3.) Speed of Execution and Decision-Making:

• How important does TJ believe speed of execution is for startups today?

• What can founders do to create a culture of rapid decision-making? What works? What does not?

• What does TJ believe are 1-2 of the single best and worst decisions he made with PillPack?

• What are some of the biggest mistakes TJ sees founders make both in speed of execution and then also in decision-making processes?

4.) The Crucible Moments: Lawsuits & Acquisitions:

• How did an incumbent come days away from shutting down PillPack?

• How did they save the company? How does TJ deal with those moments of intense stress?

• How did the Amazon acquisition come to be? Why and how did the prior acquisition fall through?

• Does TJ regret the sale to Amazon? How was life at Amazon post-acquisition?