Key Topics Covered:

• Why chasing money alone often leads to dissatisfaction
• Redefining success as economic independence, not net worth
• The Hawaiian Hobbit story and intentional living
• Micro-wins as the foundation of fulfillment and growth
• Why destinations without new horizons lead to regression
• The velocity of money explained through real estate
• Why traditional investments don’t multiply purchasing power
• How leverage, refinancing, and 1031 exchanges accelerate progress
• Income replacement vs. “being a millionaire”
• Portfolio refresh cycles (5–10 years) and avoiding stagnation
• Letting numbers—not emotion—drive buy, hold, and sell decisions
• Wise stewardship, tax advantages, and long-term planning
• Real estate as a vehicle for freedom, not just wealth

Memorable Takeaways:

• Success is a lifestyle that breeds fulfillment—not a checklist
• Growth is who we are; stagnation is the real enemy
• You don’t need a million dollars to live a rich life
• Freedom is the real dream behind most financial goals

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The perfect time to act—especially in real estate—is not someday, not when things feel safer, and not when the headlines calm down. The perfect time is now.

• The Power of the Present Moment
  • You can’t change the past.
  • You can’t control the future.
  • The only leverage point you have is today.
• A Life-Changing Wake-Up Call
  • A tragic, personal story that reshaped the meaning of urgency, presence, and purpose.
  • A reminder that time is not promised—and delaying what matters most comes at a real cost.
• The Three Degrees of Action
  • Inaction – Choosing comfort, avoidance, or procrastination (often rooted in fear).
  • Active Action – Lots of movement, preparation, and effort… but no meaningful results.
  • Productive Action – Focused, uncomfortable, results-driven behavior that actually creates change.
• Why Active Action Can Be More Dangerous Than Inaction
  • It creates the illusion of progress.
  • When results don’t show up, people conclude: “Action doesn’t work.”
• The “Do It Now” Philosophy
  • Inspired by W. Clement Stone, who built a billion-dollar empire one micro-win at a time.
  • Small, immediate actions compound into massive results.
• The Real Estate Application
  • The best time to buy real estate was 20 years ago.
  • The second-best time is always today.
  • Market cycles change—principles don’t.
• Market Myths, Fear, and Noise
  • Why advice from people with “teeny tiny pockets” should be filtered carefully.
  • Media fear vs. investor fundamentals.
  • The danger of waiting for perfect conditions.
• Moneyball Proof Across Every Market
  • 2008 crash
  • Post-recession recovery
  • COVID uncertainty
  • Post-pandemic normalization
  • In every cycle, principled investors who acted won.

If you’re waiting to feel ready, comfortable, or certain—you’ll be waiting forever. Progress begins when preparation turns into productive action.

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Takeaways

• Let experts do expert-level work for you.
• Investing in real estate makes you a business owner.
• Cost effectiveness should be viewed as strategic utilization.
• A successful business operates on the combined efforts of specialists.
• You can focus on what you do best.
• Trusting a team to manage your portfolio demands trust.
• Self-management often leads to higher costs in the long run.
• Property managers balance compassion and business interests.
• Managing your real estate investments is a full-time job.
• Every time you allow an expert to perform expert work, it's a micro win.

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• Kevin opens with a story about a magician using a penny, a toilet paper cannon, and a leaf blower to create an “impossible” trick.
• How the trick actually worked: palming the coin, using the toilet seat and TP storm as cover, and revealing the penny with initials “magically” on his tongue.
• Parallel to real estate: what looks like magic from the outside is actually hours of practice, failed attempts, and a precise formula executed consistently.
• Steve connects the idea to spiritual habits: showing up at church, praying, and keeping commitments—over half of success is simply showing up and honoring your commitments.
• How Kevin and Steve reverse-engineered their own wins and failures into the Moneyball Real Estate system and principles.
• Why single-family rentals (SFRs) are surprisingly liquid when bought in the right markets, at the right prices, with the right structure.
• Ways to access liquidity from SFRs:
  • Selling into a large buyer pool
  • Refinancing
  • Using a HELOC
  • Cash flow over time
• Introduction of the “magic number”:
  • Input = total out-of-pocket investment
  • Output = total profit on sale after 10 years (the magic number)
  • Then converting that magic number into average annual ROI.
• Key expense-side numbers in the Moneyball analysis:
  • Purchase price
  • Loan amount
  • Monthly PITI (principal, interest, taxes, insurance)
  • Property management fees
  • Vacancies and repairs
• Key income-side and growth numbers:
  • Estimated monthly rent (data-driven from in-market managers)
  • Rent growth assumptions (around ~3% annually)
  • Multiple appreciation assumptions (3.5%, 5%, and “what if it’s higher?”)
• The Average Monthly Increase (AMI) as a favorite metric: turning a 10-year profit into a monthly “magic” benefit.
• Breaking down:
  • Monthly cash flow
  • Monthly principal reduction (tenants paying down your loan)
  • Monthly depreciation/tax savings
  • Combined into Monthly Combined Cash Increase.
• Why cap rate is included but not central to Moneyball-style decision making.
• The difference between:
  • Cash-on-cash return (just cash flow)
  • Combined cash-on-cash return (cash flow + principal paydown + tax savings).
• General rule-of-thumb targets for a purchase-worthy Moneyball property:
  • Combined cash-on-cash return in the high single digits
  • AMI over $700/month
  • Annualized total return over 13%
  • Total profit on sale over $100,000 after 10 years.
• Understanding P&L vs real performance:
  • Why properties can show a loss on paper but still produce strong positive cash flow.
  • The role of depreciation and amortized costs in creating tax losses.
• How DFY uses a hybrid statement to reconcile real cash flow with tax benefits.
• Emphasis on predictable, consistent, ethical investing:
  • Buying conservatively priced SFRs
  • Focusing on win–win deals for sellers, tenants, managers, and investors
  • Using 1031 exchanges and refinances to grow instead of cashing out and killing the goose.
• Closing idea: There’s no cheat code or secret shortcut—just a clear formula anyone can follow if they’re willing to be patient, disciplined, and ethical.

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In this episode:

Steve shares the unbelievable story of his wife’s sudden heart attack during a mountain bike ride—and the surprising perspective of a young boy who noticed only the “awesome bike.”

Why perspective is a light switch you control, especially when the path toward your financial goals feels dark or overwhelming.

The conference room analogy that reframes how to approach your financial journey—with or without guidance.

How perspective directly influences market selection in real estate.

Why focusing on the right property matters more than falling in love with a geography.

A guided walk-through of the four major categories in DFY’s investment score:

Economics

Demographics

Geography

Investor Friendliness

Why fulfillment—not hustle, not comparison—is the real heartbeat of the Micro-Wins mindset.

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00:00 – 02:23 | Success is earned, not given & Kevin’s two careers
Kevin introduces Chapter 6 and the core principle: invisible moments culminate in visible results. He contrasts his complacent basketball years with his hyper-prepared speaking career to show how effort (or lack of it) shapes outcomes.

02:23 – 04:49 | The fallacy of “overnight success” & Jerry Rice’s grind
Kevin breaks down Jerry Rice’s legendary work ethic—offseason workouts, brutal conditioning, and extra reps—to show that what looks inevitable on Sundays was actually forged in private.

04:49 – 07:13 | Steph Curry: practice in private, rewarded in public
Steph Curry’s story illustrates micro wins in numbers: millions of practice shots vs. thousands of made threes in games. Kevin shows how only a tiny fraction of effort is ever seen, but all of it is required.

07:13 – 09:36 | The cost of success & DFY’s invisible work (Steve’s segment)
Steve shares his daughter’s hockey journey—sacrifice, focus, and relocating for opportunity. He ties it to DFY, explaining how years of unseen work, failed attempts, and refinement sit behind the “simple” experience clients see today.

09:36 – 11:53 | Real estate application: purchase-worthy properties vs. “good deals”
Kevin transitions the principle into real estate. Success in investing is built on continual, quiet, expert effort to find purchase-worthy properties—not on flashy “deals” or lucky breaks.

11:53 – 14:15 | Myth #1: Price alone doesn’t make a good deal
He debunks the idea that “cheap = good.” Kevin walks through low-price, high-headache properties and high-price, high-risk ones, emphasizing that stress, time, and tenant issues must be part of the equation—not just numbers on paper.

14:15 – 16:34 | Myth #2: Instant equity and the “you make your money when you buy” mantra
Kevin dismantles instant equity as a universal goal, explaining that the “discount” often shows up later as rehab costs, time, or risk. He explains why flipping is a different game and not aligned with Moneyball’s consistent singles strategy.

16:34 – 21:22 | Myth #3: Cap rate as the ultimate metric
He breaks down what cap rate really measures, how it can actually go down as values go up, and why relying on it as a be-all-end-all metric is dangerous—especially when you’re using leverage.

21:22 – 26:08 | Myth #4: Cash flow & the 1% rule in changing markets
Kevin explains the 1% rule, then shows how it was born in a very specific post-2008 context. He uses a 10-year example to illustrate how strict cash-flow rules could make investors walk right past six-figure opportunities.

23:44 – 28:34 | Rethinking negative cash flow as retirement funding
He reframes a small monthly shortfall as an intentional contribution to a long-term wealth-building vehicle. Negative cash flow becomes a strategic “retirement payment” into an appreciating, debt-paydown asset.

26:08 – 30:57 | The Moneyball approach: purchase-worthy > “good deal”
Kevin introduces Moneyball Real Estate’s core lens: focus on high-demand, middle-class neighborhoods and properties that are easy to own and manage. He defines “purchase-worthy” properties and explains why market value, not just appraised value, matters.

30:57 – 33:21 | The ideal Moneyball property & tenant profile
He outlines the target property type (3–4 beds, 2 baths, 2-car garage, middle-income areas near amenities) and why property managers love this sweet spot. It attracts stable tenants and keeps headaches low—key to long-term success.

33:21 – End | Idea summary & micro-win action steps
Kevin recaps the chapter’s core ideas and offers three micro-win challenges: recognize your own invisible progress, upgrade how you define a “good deal,” and start identifying high-demand, low-supply opportunities that align with the Moneyball mindset.

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00:00 – Success Mapping & The Principle
“Always start where you are.” Success as process, not destination.

01:00 – Viktor Frankl’s Lens
Don’t aim at success; let it ensue from dedication to a cause greater than yourself.

02:23 – Define Your Why
Family security, legacy, contribution—let purpose drive consistent action.

03:30 – Start Where You Stand
Your path begins precisely at your current baseline.

04:47 – Braxton & Defense Wins Games
Find your unfair advantage; play to your strengths → micro-win momentum.

06:20 – The Three-Step Loop

Identify where you are; 2) Set one small, winnable goal; 3) Repeat.

07:11 – Breaking Big Into Small (Parenting & Pressure)
Deconstruct problems → manageable victories.

08:05 – Steve’s Boston Marathon Blueprint
Reverse-engineer pace, elevation, fueling, mindset—plan the course.

09:31 – The Iron Cowboy Formula
“One step at a time.” Move the mountain: one shovel of dirt today.

11:54 – Moneyball Mapping in Real Estate
Four singles to score a run; avoid scoreboard obsession and instant gratification.

13:30 – The $30K/Month Trap
Lofty goals are fine—timelines must be realistic and resourced.

14:09 – Reality Check: Equipment, Practice, Time
No bat? No reps? No home run. Build skill and capital the right way.

16:36 – Use Good Data, Not Pretty Data
How “cherry-picked” pro formas mislead; match financing method to math.

18:56 – Numbers Tell Stories
Same stat, different spin—context and intent are everything.

20:10 – Your Game Plan: The Bridge from Here to There
Pre-approval, cash flow modeling, risk plan, annual reviews.

21:19 – Four Common Game Plans

Just Starting Out; 2) Transitioning a Portfolio; 3) Improving Retirement; 4) First Few Micro-Wins.

22:10 – Kevin’s First Leap (House Hack + Rental)
One move changed cash flow, equity growth, and trajectory.

23:42 – Funding the First Deal
HELOCs, cash-out refi, 401(k) redeploy (with pros’ guidance): seed vs. harvest analogy.

26:04 – From 1 to 10 Properties (Over Time)
Refi, 1031, snowball principal paydowns → independence.

28:24 – Transitioning Example: Cynthia & Brent
Hands-on to done-for-you; commercial to residential—cash flow & effort improved.

30:45 – Retirement Boost Case
$2.80 bank interest vs. $300/mo cash flow—breathing room matters.

31:40 – Your First Seven Base Hits
Save down payment, get approved, assemble team, write offers, close, lease, profit.

33:07 – Chapter Wrap & Micro-Wins Checklist
Align plan to stage, use honest numbers, stack wins, repeat.

Key Takeaways (3)

Purpose first, profit follows. When our actions align with a cause bigger than us, success “ensues,” not because we chase it, but because we’re faithful to the right work done consistently.

Reverse-engineer reality. Start where you are, define where you’re headed, break the distance into daily micro-wins, and repeat—just like marathon pacing or the Iron Cowboy’s “one step at a time.”

Use math that matches the method. Don’t mix cash-buy cash flow with leveraged ROI. Honest numbers, clear context, and annual reviews keep you on a true Moneyball path.

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Learn more about DFY’s done-for-you investing approach at dfy-realestate.com

00:00 – Partnering with Momentum
Baseball analogy: aim for singles, harness the pitcher’s energy; leverage as momentum you can use.

02:23 – Leverage in Everyday Life
Employers, parents, and tech tools—how we already partner with existing assets to amplify outcomes.

04:29 – The Waterslide Analogy
Riding on engineers, builders, pumps, and physics; American business runs on leverage too.

06:47 – Debt vs. Leverage
Why consumer debt is harmful but asset-backed leverage can be beneficial; nuance beats slogans.

09:10 – The 30-Year Fixed Superpower
U.S. mortgage structure, amortization, stability; Dave & Holly’s portfolio growth via refis/sales.

11:29 – The Math of Multiplication
$250K all-cash (20% total ROI) vs. five financed properties (100% total ROI) over 5 years at 5% appreciation.

13:48 – Growth Phase vs. Payoff Phase
Use leverage to build, then de-leverage later; younger investors can accelerate timelines.

16:11 – Easier Entry: Your First Home
FHA example from Steve; equity stair-steps over decades; house hacking with a basement/ADU.

18:33 – Interest Rates: Use, Don’t Fear
Rates reflect risk; fixed vs. variable, 1980s context, and why we stick to fixed terms.

20:52 – Is Your Primary Residence an Investment?
Equity you never deploy is a locked safe; turn it into an investment by putting equity to work.

23:19 – The Worst “Investment” Framed
Thought experiment: why passive, locked-up home equity underperforms as a “savings plan.”

25:37 – Creative On-Ramps
Live-in flips (with caveats), duplex/ADU, family co-ventures; Lisa’s casita deal structure.

28:01 – The ROI Refi
Reframe refi costs as an investment; example of a 20% annual return via monthly payment savings.

30:15 – Principle-Based Leverage
Data > emotion; cash flow, cash-on-cash, reserves; when (rarely) a small negative can make sense.

32:41 – Micro-Wins & Action Items
Identify leverage you already use, find a positive leverage step, and reframe your primary residence.

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00:00 – Kevin vs. the “Hank Smith Jr. effect”: when imitation ruins authenticity—and what fixed it

02:24 – Seek the quiet applause of heaven; measuring progress, not people

04:47 – A recipe for despair: external validation and risky, look-at-me goals

07:04 – The Gap and the Gain: why measuring backward fuels momentum

09:27 – Ditch the scoreboard, grab a map: progress > points

11:48 – The net worth illusion: why income replacement is the real flex

14:11 – Steve’s Harley story: let real estate buy the toys

16:38 – It’s a Wonderful Life: getting out of the gap and into gratitude

19:00 – Client “Rand”: doors obsession → setback → sustainable singles

21:13 – Cash flow isn’t everything: mini profit centers and smarter tradeoffs

23:35 – John & Judy: 10-year journey, $2M equity, and a purpose-aligned plan

25:55 – Designing income with 1031s, refis, and right-sequenced moves

28:09 – Start now: micro-wins to economic independence

30:20 – The orchard model: seeds, seasons, and compounding growth

32:46 – Chapter recap + reflection prompts to reframe your progress

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(00:00) – The Principle: Achievement is a journey worth celebrating—not a destination.
(00:40) – Steve’s First Business Story: From a beat-up truck and borrowed tools to a 12-year painting company.
(02:15) – Micro-Wins in Action: Buying the truck, getting supplies on credit, selling jeans for gas—all small victories that built momentum.
(03:30) – The Art of Sacrifice: What are you willing to trade—time, energy, comfort—to reach your goals?
(04:45) – Movie Moment – Rudy: How one tackle defined years of determination and why small wins matter more than the highlight reel.
(06:50) – Celebrate Progress: Why you should recognize micro-wins daily to rewire your brain for success.
(08:15) – Kevin’s Gratitude Connection: How tactical gratitude and celebrating micro-wins transformed his life and inspired FLIP the Gratitude Switch.
(10:45) – Quiet Wins vs. Loud Validation: The story of the ten lepers and how real celebration happens in gratitude, not performance.
(13:30) – Applying It to Real Estate: Why every step—from pre-approval to your first rent check—is a win worth celebrating.
(15:00) – The Seven Profit Centers:

1. Cash Flow
2. Appreciation
3. Leverage
4. Tenant-Paid Principal
5. Inflation Hedge
6. Tax Benefits
7. Infinite Returns

(22:00) – Reframing “Negative Cash Flow”: How, in rare cases, it can act as a strategic monthly retirement contribution.
(24:15) – The Marathon Mindset: Real estate wealth is built through consistent, celebrated progress—not perfection or luck.
(25:30) – Key Takeaway: Don’t delay your happiness. Celebrate every base hit, every micro-win, and every small sign of progress toward economic independence.

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Learn more about DFY’s done-for-you investing approach at dfy-realestate.com