20VC: Why The CEO Should Make As Few Decisions As Possible, The Trade-Off Between Freedom and Raising Big From VCs & Why Our Jobs Are Not As Hard As We Think and How To Assess Talent and Potential As a Result with Tristan Handy, Founder & CEO @ dbt Labs

Tristan Handy is the Founder and CEO @ dbt Labs, a data transformation tool that enables data analysts and engineers to transform, test and document data in the cloud data warehouse. To date, Tristan has raised over $400M from the likes of Sequoia, Altimeter, Coatue, ICONIQ and GV with the latest funding round valuing the company at $4.2BN. Prior to founding dbt Labs, Tristan was the VP Marketing @ RJ Metrics and got his break in the world of startups through former 20VC guest, Anthony Casalena with a Director of Operations role at Squarespace.

In Today’s Episode with Tristan Handy:

1.) Entry into Startups:

• How did Tristan make his way into the world of startups with his first role at Squarespace?

• How did Tristan’s time with Squarespace impact how he builds dbt Labs today?

• What does Tristan know now that he wishes he had known when he founded dbt Labs?

2.) Our Jobs Are Not That Hard:

• Why does Tristan believe that our jobs are not that hard?

• If going down this line, how does Tristan hire? What does he look for? How does he test for it?

• When does experience matter? When does it not matter?

3.) dbt Labs: The Company

• Why does Tristan believe that remote work does not work?

• What financial packages have dbt put in place to allow their employees this physical interaction?

• What does Tristan believe is the hardest element of building a hybrid company? When does everything start to break?

• What are the biggest lessons Tristan and dbt have taken from Gitlab?

4.) Tristan: The Leader

• How does Tristan conduct and execute on the best performance reviews?

• How does Tristan create an environment of safety where people feel they can be honest and transparent?

• What are the elements that you cannot be transparent on? Where does transparency break down?

5.) Trading Freedom for Scale:

• dbt Labs could have been a small and super profitable company, why did Tristan decide to trade off the freedom and raise big from VCs?

• How did Tristan raise over $414M without ever talking about an efficiency metric?

• Is Tristan concerned about living into the $4.2BN valuation in what is a very different time?

• With the benefit of hindsight, is Tristan pleased he went big and raised venture?