Ryan Krueger, co-founder of Freedom Day Solutions and manager of the MBOX ETF, joins the discussion to reveal the shortcomings of common dividend strategies. He emphasizes the importance of prioritizing dividend growth over high yield and critiques the flawed 4% withdrawal rule. Ryan introduces 'Freedom Day,' a novel approach to retirement focused on income rather than asset accumulation. The conversation explores the necessity of a disciplined sell process and the often-overlooked factors that can elevate long-term investment success.
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insights INSIGHT
Dividend Growth Outperforms High Yield
Dividend growth outperforms high yield over time due to compounding income growth.
A 2% yield growing at 8% annually yields 5% on cost in 8 years, beating many static high yields.
volunteer_activism ADVICE
Use Yield on Cost for Behavior
Focus on dividend yield on cost to build investor confidence and encourage patience.
High yield on cost helps investors hold through volatility due to growing income streams.
volunteer_activism ADVICE
Seek Accelerating Dividend Growth
Evaluate rate of change in revenue and dividend growth to find improving companies.
Favor firms with accelerating dividend growth over slow growers to spot future winners.
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The book tells the story of the Oakland Athletics' 2002 season, where General Manager Billy Beane and his assistant Paul DePodesta used advanced statistical analysis, known as sabermetrics, to assemble a competitive team despite a limited budget. The approach, pioneered by Bill James, focused on metrics such as on-base percentage and slugging percentage rather than traditional measures like batting average and runs batted in. This data-driven strategy allowed the Athletics to compete with teams having much larger payrolls, like the New York Yankees, and achieve significant success, including a 20-game winning streak and a playoff appearance[2][3][5].
Most investors chase yield. But what if the very models they rely on — from dividend screens to the 4% rule — are fundamentally broken?
In this episode, we’re joined by Ryan Krueger, co-founder of Freedom Day Solutions and manager of the MBOX ETF, to explore the overlooked truths of dividend investing. Ryan breaks down the importance of dividend growth over yield, why most dividend strategies ignore free cash flow, and how a disciplined sell process separates long-term success from failure. He also explains the concept of “Freedom Day” — a reimagined approach to retirement that’s built on income, not asset totals.
Whether you're a dividend investor, financial advisor, or retiree planning for long-term income, this conversation offers a fresh, practical framework you won’t hear elsewhere.
We discuss:
Why dividend growth beats high yield over time
The flaws in the 4% withdrawal rule
How yield-on-cost changes investor behavior
Red flags hidden inside popular dividend ETFs
How “Freedom Day” redefines retirement planning
Ryan’s quant + discretionary investment process
The underrated power of sell discipline
Why “never add to losers” might boost your returns
Excess Returns 