Broken Models. Misleading Yields | Ryan Krueger on Avoiding the Dividend Trap

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

📈 Learn more about Ryan’s work: https://freedomdaysolutions.com