What if the traditional retirement planning model is broken — and dividend growth investing holds the key to a better path? In this episode, we sit down with Ryan Krueger, co-founder of Freedom Day Solutions and manager of the MBOX ETF, to explore how his dividend-focused strategy reframes investing and retirement. Ryan shares hard-earned insights from decades of experience, diving deep into what dividend growth really signals about business quality, why most dividend strategies fall short, and how investors can create more resilient portfolios with the right mindset and math.
Topics Covered:
Why dividend growth outperforms — and what it really signals about a business
What most investors get wrong about dividend yield and “safe” stocks
How Freedom Day redefines retirement around income, not asset size
The key behavioral advantage of yield-on-cost for long-term investors
Why dividend ETFs like aristocrats may be hiding major red flags
How to measure dividend quality using free cash flow and payout ratios
The role of sell discipline — and how pros fail by ignoring it
Why Ryan believes a simple quant + momentum filter beats most managers
How to build a 50-stock portfolio that balances growth, value, and quality
What mailbox math reveals about income and peace of mind
The underrated role of work and lifestyle choice in retirement planning
Timestamps:
00:00 – Dividend growers vs. high yielders
01:00 – Welcome back Ryan Krueger & MBOX ETF update
02:30 – The origin of “Freedom Day” and redefining retirement
05:00 – Why Krueger launched an ETF after years of SMA success
08:45 – ETFs vs. SMAs: transparency, behavior, and tax efficiency
09:45 – The case for dividend growth over high dividend yield
11:00 – Yogi Berra math: compounding and yield on cost
13:00 – Dividend growth as a quality signal
15:00 – Stakeholder yield: dividends + buybacks + debt paydown
17:00 – Problems with aristocrats and traditional dividend indices
19:00 – Starting yield vs. total return framework
21:00 – Momentum and technicals as supplemental signals
22:00 – How dividend growth performs in market downturns
23:30 – The behavioral power of yield on cost
26:00 – Humility, curiosity, and behavioral edge
27:00 – Active vs. passive dividend strategies
28:30 – Expanding moats vs. big, leaking ones
30:00 – Krueger’s stock selection process: operating advantage
33:00 – Measuring dividend quality and sustainability
34:45 – Krueger’s “stock tournaments” by sector
36:00 – Portfolio construction and valuation mindset
38:00 – Why 50 stocks? Balancing concentration and diversification
41:00 – Sell discipline and pre-defined exit criteria
44:00 – Tech stocks behaving like staples
46:00 – Why the 4% rule may be outdated
49:00 – Mailbox math and financial peace of mind
52:00 – "Am I going to be OK?" and the power of simple questions
55:00 – Lessons from launching an ETF as a small issuer
57:00 – What most professionals get wrong: no sell discipline
58:00 – The importance of skin in the game
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