Group 1: Startup Investing Insights - The high-risk nature of startup investing can be appealing to high-net-worth investors with diversified portfolios, but average investors may benefit more from guaranteed returns and low-risk options [1] - The commonly cited statistic that 90% of startups fail is likely exaggerated; Harvard Business School estimates the actual figure is closer to 75% [2] - Mark Cuban, known for his role on Shark Tank, has invested in at least 85 startup ideas, but his overall investment deals on the show resulted in a net loss [5] Group 2: Investment Strategies and Lessons - Cuban's investment success rate is not unusual compared to the general performance of the startup asset class [2] - Key lessons for everyday investors include starting small to test risk tolerance, diversifying investments across various sectors, and focusing on established businesses with strong track records [11][15] - Cuban's portfolio includes a wide range of investments beyond startups, which contributes to his continued wealth despite failures [15] Group 3: Real Estate and Alternative Investments - Real estate remains a robust market for investors, with platforms offering fractional ownership in properties, allowing for monthly rental income and appreciation without significant upfront costs [17][19] - Commercial real estate is also gaining interest, with a Deloitte survey indicating that nearly 75% of leaders in the sector plan to increase investments due to its inflation-hedging benefits [21] - Gold is highlighted as a safe haven investment, providing stability during market downturns, and can be included in retirement portfolios through gold IRAs [24][25] Group 4: Art as an Investment - Fine art is presented as a low-correlation asset class that can diversify portfolios, with historical performance showing strong rebound potential [27][28] - Masterworks allows investors to own fractional shares of high-value artworks, yielding significant annualized returns [29]

(btw I've also angel invested in Ethereum, Bitcoin, Celestia, Near, Hyperliquid and other ecosystems in the past 3 years. Crazy!!!!) ...

I had fantasized about going to Stanford business school for ages. I was very unhappy at Princeton. That's where I went as an undergrad.I felt like I made a big mistake. Stanford was the other one I wanted to go to, but for a for a bunch of reasons, I decided not to do it. And so when this thing came up with Mike Maples, I thought, well, why don't I take what I would have spent on tuition, 120k for 2 years, something like that.And that would have been some cost. I pay out of pocket. And what's the hope with ...

You've been doing some angel investing. Yes. I saw that you called it dolphin tank as opposed to Shark Tank.Well, I love Shark Tank, by the way. Don't get me wrong. I love watching that show.I just wanted to approach it with friendly water. Yeah. What's the bigger strategy.Like, are you looking at AI or biotech or ecommerce or AI. Man, I aren't you a little bit scared by AI. Just a little.I mean, we have to make peace with it. The the world is changing. Our lives are changing.So there's certain things that ...

People are VERY aware that early stage venture isn’t guaranteed wins anymore.Prominent angel investors are in group chats saying "I'm not doing angel investing right now" & VCs are being far more picky.What are the second and third order effects of this??? ...