When meeting founders for Series A investments, it’s a pretty high bar. We see companies with extraordinary vision, ambition and speed of growth. And we want every new investment to be better than the last, so competition is huge. My focus is always first and foremost on the founder and I ask myself:

• Do they have an amazing scale to their thinking?
• Can they articulate their thinking in a compelling?
• Do they have a fire burning inside or a chip on their shoulder ?
• Are they compelled to prove a lot of people wrong?
• Do they have a balance of conviction and coachability?

You can read more about this here. You can also listen to the full podcast here:

Beyond the characteristics of the founder I look at many other aspects.

1. Obsess with product: Beyond seed, I also obsess about the product. I like to see founders thinking about their product in a very customer centric way, always thinking about and talking to the customers. Founders should obsess about the details as well as the big picture.
2. Hit a plan: As you get to the later stages, one thing that often gets overlooked is the ability to hit a plan. It’s interesting to keep the investment from the last time they pitched you, or to see previous plans and board packs and then compare performance. Because, as a company grows, this ability to deliver on a plan is critical for success.
3. Build a strong team: Demonstrate your ability to build a really strong team, so the founder doesn’t have such a strong ego. With a strong team, not all roads have to lead the founder, and it means they won’t be taking on more than they should be or are able to.. I like to see founders with the self awareness to let go and build a team, and give people the freedom to express themselves, allowing people to take risks.

From 1,000 investment discussions, I’ve made approximately 30 investments - 15 personally and 15 with Notion.

I’ve invested in less than 3% of the companies who’ve pitched me, and a few stand out.

A seed investment: Brynne Kennedy at Topia had lived through the pain of being moved around the world by her employers and experiencing a very painful process. Brynne’s idea to build a digital platform to move employees around the world was compelling to me,it felt like a new frontier for tech. That took hold of me quite early.

A Series A investment: In the summer of 2018 I invested in a business called Futrli, a bootstrapped business with an amazing founder,Hannah Dawson. Hannah and Futrli had achieved significant revenues and were profitable, which says a lot about Hannah and the team she’d built. It felt like a business that could be turbo-charged with funding. Their vision is to take backward-looking financial data and use it to make better decisions about the company’s future.