285. Non-Dilutive Financing Options, Fintech is Eating the World, Digital Asset Aggregation, and Quants Investing in VC (Billy Libby)

Billy Libby of Upper90 joins Nick to discuss Non-Dilutive Financing Options, Fintech is Eating the World, Digital Asset Aggregation, and Quants Investing in VC. In this episode, we cover:

• Walk us through your background and path to VC.
• What’s the thesis at Upper90?
• On the website, it says "We are not looking to finance major technology disruptors but rather the derivative businesses being created around them." Can you explain what you mean by that?
• How do you underwrite and assess the risk of some of these platform-dependent technologies (channel choke)? If you build businesses that are dependent on top of Facebook, for instance, or on top of Slack, or businesses related to the Amazon ecosystem, like Thrasio, how do you think about the risk of the platform deciding they no longer want to play nice with you?
• What is the split of your fund - the equity versus the debt component?
• And the terms of the debt, are there multiple different forms and different terms, or have you standardized that?
• Do you do some debt in non-dilutive financing options for non-portfolio companies? Or is it always an investment plus the credit?
• Do you include rights in some of those agreements to convert into equity should you choose?
• We've seen a lot of players, sort of FinTech startup-ish players, springing up providing access to capital for working capital needs and credit needs. Like Pipe and Lighter cap and CapChase and all these players. How are you similar and different from them? And how do you think about that?
• Is there ever a conflict, you know, when you're making an equity investment, but you also have debt in these companies? If they get in a tight situation? potential for conflicts?
• You said that you'll enter at seed. Are there certain metrics or revenue levels that you're looking for other structural dynamics, whether it be collateral or SAS subscription revenue? What's too early would be another question.
• There are a number of market makers here in Chicago that have entered sort of the VC asset class, what skills or strategies from your experience in your background? What do you think lends well, no pun intended, to driving top returns in venture?
• Can we get your thoughts on big drivers and opportunities in FinTech over, let's say the coming three years.
• What do you know, you need to get better at?