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by Patrick O’Shaughnessy

My guest today is Arianna Simpson, who has spent her career in an around the world of technology working at startups, Facebook, and now in venture capital as an investor focused on the world of cryptocurrencies. I met Arianna when I hosted a panel at a big investing conference in New York City and she was one of the panelists. On the panel, I found her style to be very straightforward and compelling. It is clear that she loves to learn and that the best manifestation of her style of learning is investing in technology.

In our conversation, we discuss broad trends in crypto that we haven’t spent much time on before: decentralized versus centralized exchanges, privacy coins, and evaluating a founder or early team. We build a framework for learning about this new asset class, discuss the importance of travel, and the value of pushing oneself outside of comfort zones.

Please enjoy our conversation


Show Notes

2:12 – (First question) – How to teach someone else to build an investing philosophy around crypto


4:00 – The major risk factors to investing in crypto


6:28 – best practices for mitigating risk


7:39 – What factors to think about when it comes to whether a token will lose all value or not


8:39 –  Taking a pulse of the investment community on crypto


11:36 – How she heard about and became interested in crypto currencies


12:34 – Are people really using crypto currency as a hedge against rampant inflation


13:52 – Investing thesis in the space


14:07 – Arianna’s systems for learning about cryptocurrencies and staying up to date on them


15:19 – Arianna’s take on the issue of increasing transactional through put


16:49 – Layer 1 solutions and making it all scalable on a blockchain


17:56 – her take on the fat protocol thesis


20:32 – Defining utility vs security tokens


21:54 – evaluating different coins


21:02 – Why cross currency swaps are important and how they work


26:17 – What are the chances of a scenario where there’s just one token and everything is built off of that one


28:02 –  Comparing centralized and decentralized exchanges


29:47 – How the traditional investing world is going to regulate transaction involving cryptocurrencies and view security around those transactions


31:54– Impact this will have on capital formation


33:44 – Evaluating teams behind crypto companies


35:48 – The importance of gut when evaluating people


38:47 – How Arianna’s global upbringing impacts her thinking on the technology


39:51 – What countries or regions have had the largest impact on Arianna’s investing philosophy


42:41 – Doing things you’re not qualified for


43:59 – Gender imbalance in crypto and what can be done to shift that


45:28 – Most recent thing that has gotten Arianna excited in the crypto space


46:15 – Explaining Zero X


47:33 – How her views on reading have evolved


48:54 – Kindest thing anyone has done for Arianna

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