20VC: Kevin Weil on The Biggest Lessons from Leading Product at Instagram and Twitter | How Working With Kevin Systrom Impacted His Approach To Product | 3 Things Instagram Did To Make Stories So Successful and Why Investing Makes Operators Better at Their Day Job and Why More Should Do It

Kevin Weil is President of Product and Business @ Planet and Operator in Residence @ Scribble Ventures. In the past, Kevin has been Head of Product at Twitter, Instagram, and Novi (the digital currency effort within Facebook). During his seven years at Twitter, he helped the company scale from 40 to 4000 people and from $0 to $2B in revenue. He then moved to Instagram in 2016 to lead the product and data teams and led through an inflection point as Instagram grew from 400M to over 1B users, including launching Instagram Stories. Kevin then co-founded Diem (formerly known as Libra) and Novi and built both for three years before moving to Planet in 2021. If that was not enough, Kevin is also on the board of Strava, the Nature Conservancy, and the Black Product Managers Network.

In Today’s Episode with Kevin Weil We Discuss:

1.) Lessons From Leading Product for Instagram and Twitter:

• What does Kevin believe makes Instagram so inherently good at product? How did leading product for Instagram change the way Kevin thinks and operates?

• What are 1-2 of Kevin’s biggest lessons from working with Kevin Systrom, Instagram’s Founder?

• What are the biggest takeaways for Kevin from leading product at Twitter?

2.) Launching Products, Customer Discovery and Product Sessions:

• What were Kevin’s biggest learnings from launching Instagram stories? How did Kevin’s conviction impact the product building and success of Instagram stories?

• How does Kevin advise founders on the best way to approach customer discovery? What are the best questions to ask to reveal the truth?

• How does Kevin approach product testing today? Why does Kevin not like softly softly testing new products?

3.) Kevin Weil: Leadership 101

• What are some of the biggest leadership mistakes that Kevin made in his time at Twitter?

• How does Kevin approach decision-making frameworks? How does one balance the speed vs the quality of the decision?

• What makes a great product strategy? Where do so many go wrong in their product strategy?

• How do the best leaders communicate with their team? How does this change over time?

• What is Kevin’s preferred medium and style of communication with his teams?

4.) Kevin Weil: The Athlete, Father and Husband:

• Kevin is an ultra-marathon runner, what does his training routine look like?

• What 1-2 changes has Kevin made that have had the biggest impact on performance?

• How does Kevin manage, investing, advising, training and being a father and husband?