Jason and Jeff discuss the lessons they've learned from years of investing, recount their early financial missteps, and explore what they would do differently if they had to start their investment journeys from scratch today.

00:36 Starting from Scratch: A New Investor's Journey

01:33 Reflecting on Past Mistakes and Learning

02:37 Investing in Your Early Twenties vs. Now

03:19 Adapting Investment Strategies Over Time

16:04 The Importance of Automating Savings

23:30 Earnings Growth and Financial Success

30:50 Understanding Compounding and Inflation

32:58 Teaching Financial Literacy to Kids

34:09 Reflecting on Investment Strategies

35:07 The Role of Humility in Investing

38:58 Starting Over: Portfolio Strategies

42:10 Rolling Over Retirement Accounts

49:25 Aligning Finances with Values

52:53 Frameworks vs. Rules in Financial Planning

Companies mentioned: AAPL, CRWD, KNSL

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