20VC: Notion's Founder on "Founder Mode": When it Works & When it Doesn't | Why The Way Startups Fundraise & Construct Boards is Broken | Raising at a $10BN Valuation in Peak Bubble Times and How Notion Has More Money Than Ever Before with Akshay Kothari

Akshay Kothari is Co-Founder at Notion, one of the fastest-growing companies of the last decade. Akshay has run every function in the company from sales, to marketing to finance and even led their fundraising efforts raising $340M+ from Sequoia, Index and Coatue with the latest round pricing them at $10BN. Before Notion, Akshay was VP Product at Linkedin for 5+ years, leading all of their content efforts. He joined LinkedIn when his previous company, Pulse, was acquired by LinkedIn in 2013.

In Today's Episode with Akshay Kothari We Discuss:

1. Founder Mode, Veto Powers and Focus:

• Does Akshay agree with "founder mode"? What are the biggest downsides to founder mode that not enough people are discussing?
• Why does Akshay believe that the single greatest power of a founder is their "veto power"?
• What is the biggest opportunity that Notion jumped on that they should not have done?
• What is the biggest opportunity that Notion did not jump on that they should have jumped on?

2. Raising $50M @ $2BN Valuation:

• Why did Ivan and Akshay decide to do this raise when they did not even need the money?
• How did the fundraising process for this round go? Why did they choose Coatue and Index?
• Why did Sequoia say no to this round?
• With the benefit of hindsight, what does Akshay wish that they had done differently?

3. Raising $270M @ $10BN Valuation:

• How did Sequoia come back into the frame with this round? Why did they say yes here when they did not before?
• Why does Akshay believe that of all the investor brands, Sequoia is the most powerful? In what way does having Sequoia as an investor change the trajectory of the company?
• Is Akshay concerned about how he will be able to scale into the $10BN valuation?
• How does Akshay address the challenge of bringing new team members in with stock options priced at $10BN? How much of a blocker is that?

4. Boards and Social Media are F*******:

• How is the way in which boards are constructed broken?
• How does Akshay believe that boards should be constructed?
• What roles should founders hire for in their board members?
• Why is Akshay most concerned about the "Tiktokification of everything"?
• Why does Akshay believe that social media has never been more concerning?