Ryan Akkina is a member of the Global Investment Team at the MIT Investment Management Company (MITIMCo), which is responsible for managing MIT's endowment and pension plans. Ryan has invested in the likes of Sequoia, Kleiner Perkins, a16z, Greenoaks and Initialized to name a few. Ryan also leads many of MITIMCo's direct co-investments including most notably into Coupang and Rippling. Prior to joining MITIMCo, Ryan was a consultant at McKinsey & Company.

1. From Engineer to LP with MIT:

• How did Ryan make his way into the world of fund investing as an LP with MIT?
• Why did he turn down the chance to be a VC early in his career?
• What does Ryan know now that he wishes he had known when he started at MIT?

2. The Manager Evaluation Process for MIT:

• What does Ryan look for most when investing in new managers?
• How important is track record when evaluating a new manager?
• What is the biggest mistake Ryan has made in picking a manager? What did he not see that he wish he had seen? How did that change his process?

3. How MIT Builds Their Portfolio:

• How does MIT construct their portfolio from private to public to everything in between?
• What are the three different types of check sizes that MIT writes when investing in new managers?
• What are the most common reasons why MIT will not re-up with a manager?
• What are the single biggest reasons why great managers turn bad?

4. MIT: The Direct Investor:

• Why does MIT see so much opportunity in direct investing?
• How does MIT approach the direct investing process? How do they approach underwriting themselves vs working with their managers in the process?
• How do MIT think about the right number of direct deals to make up their portfolio?
• How do they approach check sizing on a per-company direct investment?
• What has been Ryan's biggest direct investing mistake? How did that change his approach and mindset?

5. LP Markets Today and Where We Go From Here:

• Are LPs open for business today? What type of firms will not struggle? Which will?
• How does Ryan view liquidity windows today? When will M&A and IPO markets open?
• What would Ryan most like to change about the world of LPs?
• Why does Ryan believe the LP incentive structure in terms of compensation is broken?