0:00 -- Intro.1:30 -- Start of interview.2:12 -- Barrett's "origin story".6:11 -- His start in finance. First in Stone & Youngberg then in Lehman Brothers in SF. His first secondary market transactions in private company stock (Facebook) in 2007.8:54-- His experience working at SVB (internship with wine finance team) and Lehman Brothers (business development).12:10 -- The early days of secondary market transactions for private company stock with SecondMarket, later acquired by Nasdaq in 2015 (now Nasdaq Private Market).14:25 -- His entrepreneurial stint as CEO of Juno Company, a children's educational media company.15:56 -- His VC stint as an advisor with Maveron.17:20 -- On the founding of his firm Scenic Advisement in 2013.18:12 -- History of investment banks in SF helping founders to get liquidity (the Four Horsemen of Silicon Valley’s financial community: Alex.Brown, Hambrecht & Quist, Robertson Stephens & Co. and Montgomery Securities underwrote a large number of IPO offerings, both before and during the dotcom boom.)20:36 -- The ethos and vision behind Scenic Advisement. "The opportunity was to build a bank that really was the standard bearer, establishing best practices so that [institutional investors] had a counter-party or a middleman who could speak their language and conversely, the people building great companies had a partner who they could trust, because that partner had empathy: they were ex founders, ex VCs or from the community, not some transactional banker who lives 3,000 miles away and knows nothing of the company but knows that there is a big fee to be had and a league table to be on." "Our plan was to drive hard empathy."24:17 -- On the current state of private markets. "It's been a boom marked by irrational exuberance, and then a correction, as markets do." "But I can tell you, and I do so with great thanks, that the market is thawing and we are starting to see investors come back." "I could have taken all of 2022 off, and from a stress perspective, it would have probably been beneficial, but I just didn't have a crystal ball."27:42 -- On the regulation of unicorns and private markets generally. Going dark speech by SEC Commissioner Lee (Oct 2021).33:08 -- On the Stay Private for Longer ("SPL") advice in Silicon Valley ["The worst advice" per Gurley and Rabois]. "Companies now stay private long. That's it. This is not a trend, it is a market reality at this point." "It's also totally business dependent."37:52 -- The opportunities and challenges for founders, investors and employees in private markets. "The Sequoia move to an evergreen fund structure is a brilliant idea." "The Stripe multi-billion financing was the company being really proactive to options expiry, to ensure that the most important asset at Stripe, the people, are made whole or don't loose the benefit of the bargain (that would be awful for everyone and for morale)." "We are going to see more and more of that." 39:39 -- How companies treat employees vs ex-employees on stock options: "It varies from company to company and from founder to founder. My advice typically is to be egalitarian."41:21 -- On regional differences in tech ecosystems in the US.43:47 -- The impact of the collapse of SVB and First Republic in the SF/Bay Area tech ecosytem. "I believe in diversification. I believe in selling early and often. I want to implore founders and investors to take chips off the table when you can, because you can't always and things go away. People forget that."47:40 -- Thoughts on crypto and digital assets market.49:17 -- Thoughts on Artificial Intelligence (AI) market. "It's the next major wave. Unlike crypto and digital assets, this is not a fad."51:05 --  The books that have greatly influenced his life: Everything by Philip Roth.Exodus, by Leon Uris (1958)Everything is Illuminated, by Jonathan Safran Foer (2002)51:38 -- His mentors, and what he learned from them: the most impactful mentor for him has been his mother.52:58 --  Quotes he think