The Retirement Income Guru
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NEW Why You Need a Retirement Income Specialist, Not a Generalist NEW Roth Conversions: Should You Join the Craze — or Think Twice? NEW The Healthcare Cost Misconception: What the Headlines Get Wrong NEW Will Your Money Last? Interactive Monte Carlo Charts NEW The Retiree Spending Wave™ — A New Way to Think About Retirement NEW The Math of Loss: Why Drops Are Harder to Recover From Than You Think NEW Annuities: Your Personal Pension — $434B in Sales and Counting NEW What Running a Pension Fund Taught Me About Retirement NEW Retirement Income Guardrails: Would You Drive the Golden Gate Without Them? NEW Writing Covered Calls for Income — I Use This Every Week NEW Common vs. Preferred Stock for Dividend Income
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NEW The Healthcare Cost Misconception: What the Headlines Get Wrong NEW Will Your Money Last? Interactive Monte Carlo Charts NEW The Retiree Spending Wave™ — A New Way to Think About Retirement NEW The Math of Loss: Why Drops Are Harder to Recover From Than You Think NEW Annuities: Your Personal Pension — $434B in Sales and Counting NEW What Running a Pension Fund Taught Me About Retirement NEW Retirement Income Guardrails: Would You Drive the Golden Gate Without Them? NEW Writing Covered Calls for Income — I Use This Every Week NEW Common vs. Preferred Stock for Dividend Income
🎙 Podcast Launching Soon — Subscribe to Be Notified
Your Retirement Income Education Hub

Everything you need to know
about turning savings into
lasting retirement income.

Weekly podcasts, in-depth articles, and practical guides on dividend investing, annuities, Social Security, tax strategy, and every risk standing between you and a confident retirement.

8
In-Depth
Articles
6
Income
Topics
100%
Always
Free
Episode 6 · 38 min
Is the 4% Rule Still Safe in Today's Market?
We revisit the famous 4% withdrawal rule — where it came from, why some experts now say it needs adjusting, and what withdrawal rate actually makes sense for your life.
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Also available on Spotify · Apple Podcasts · YouTube
Latest Articles
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Will Your Money Last?What the NumbersActually Say
Withdrawal Strategy
Will Your Money Last? What the Numbers Actually Say

How much can you take from your portfolio without running out? Interactive charts and historical success rate tables show exactly how the numbers play out — and what a guaranteed income stream changes.

⏱ 7 min read
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The Retiree SpendingWave™
Retirement Income Planning
The Retiree Spending Wave™

Traditional retirement projections show spending rising in a straight line. After nearly three decades working with retirees, I believe that's wrong. Real retirement spending looks like a wave — and planning around that reality changes everything.

⏱ 11 min read
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Annuities: YourPersonal Pension
Income Strategies
Annuities: Your Personal Pension

With pensions nearly extinct in the private sector, Americans are buying annuities at record levels. Here's what they actually are, the misconceptions that hold people back, and why $434 billion in sales tells its own story.

⏱ 9 min read
Read Article →
Writing Covered Callsfor Income
Income Strategies
Writing Covered Calls for Income

If you own stocks, you may be sitting on an income source you're not using. A plain-English explanation of covered calls — and why I use this strategy in my own portfolio every single week.

⏱ 10 min read
Read Article →
Common Stock vs.Preferred Stock forDividends
Dividend Investing
Common Stock vs. Preferred Stock for Dividends

Both pay dividends — but they work very differently. Here's what every retiree needs to understand before building a dividend income portfolio, including the one risk most investors miss.

⏱ 8 min read
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What Running a PensionFund Taught Me
Retirement Income Planning
What Running a Pension Fund Taught Me

I serve as volunteer chairman of a local fire and police pension board. The framework pension funds use — Asset Liability Management — applies directly to how individuals should manage their own retirement income.

⏱ 10 min read
Read Article →
Retirement IncomeGuardrails: Would YouDrive the Golden GateWithout Them?
Withdrawal Strategy
Retirement Income Guardrails: Would You Drive the Golden Gate Without Them?

One of the most talked-about retirement income strategies borrows its name from the highway. Here's what guardrails actually do, how they work, and the critical limitation that often gets overlooked.

⏱ 10 min read
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The Math of Loss: WhyMarket Drops AreHarder to Recover FromThan You Think
Retirement Risks
The Math of Loss: Why Market Drops Are Harder to Recover From Than You Think

A 20% loss takes a 25% gain to recover. A 50% loss takes 100%. Most people don't realize this — and when you add retirement withdrawals on top, the math becomes even more unforgiving. Interactive charts show exactly what the numbers look like.

⏱ 10 min read
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The HealthcareCost Misconception:What the HeadlinesGet Wrong
Healthcare in Retirement
The Healthcare Cost Misconception: What the Headlines Get Wrong

Fidelity says $172,500. HealthView says nearly $1 million per couple. The numbers are real — but the context most reports leave out changes everything. Once you understand Medicare and Plan G, healthcare costs are far more predictable than you think.

⏱ 9 min read
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Roth Conversions:Should You Jointhe Craze — orThink Twice?
Tax Planning
Roth Conversions: Should You Join the Craze — or Think Twice?

Everyone is pitching Roth conversions right now. The advice isn't wrong — but it's not always right either. Learn what "burping the bracket" means, why your rate of return matters more than most advisors admit, and how to know if a conversion actually makes sense for your situation.

⏱ 12 min read
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Why You Needa RetirementIncome Specialist,Not a Generalist
Retirement Planning
You Wouldn't Let Your Family Doctor Perform Brain Surgery. Why Are You Letting a Generalist Plan Your Retirement?

Distribution planning is a completely different discipline from accumulation. The decisions you make at retirement are irreversible — and most financial advisors aren't trained for them. Here's what separates a true retirement income specialist from a generalist.

⏱ 11 min read
Read Article →
🎙 The Retirement Income Guru Podcast
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Coming Soon

Weekly conversations about retirement income — in plain English.

Each week, Kris Cowles breaks down one retirement income topic — no jargon, no sales pitch, just clear practical insight you can actually use. Episodes cover everything from Social Security timing to sequence of returns risk, dividend investing, annuities, Medicare, and more.

🎯 Weekly Episodes
⏱ 5–15 Minutes
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Be the first to know when Episode 1 drops.
Upcoming Episodes
🎙
Ep. 1: Why Retirement Income Is a Completely Different Problem
The introduction — what this podcast is all about
💰
Ep. 2: Dividend Investing for Retirement Income
Building a portfolio that actually pays you
📉
Ep. 3: Sequence of Returns Risk
Why the first 5 years of retirement are critical
🏛️
Ep. 4: Social Security at 62 vs. 70
The decision that could be worth $100,000
Retirement Income Strategies
Explore every way to generate income in retirement — with honest pros, cons, and real-world examples.
💰
Dividend Investing
Income from stocks that pay regular dividends
📜
Annuities
Guaranteed income for life or a fixed period
🏦
Bonds & Bond Ladders
Fixed income with predictable maturity dates
🏧
CDs & High-Yield Savings
FDIC-insured, low-risk fixed returns
📊
Portfolio Withdrawals
Systematic drawdown from diversified portfolios
🏛️
Social Security
Maximizing your government-guaranteed income
Kris Cowles - The Retirement Income Guru
Kris Cowles
The Retirement Income Guru
Previous Experience
Edward Jones Investments — Financial Advisor
INVESCO Funds — Retirement Plan Consultant
ING — Regional Vice President
Allianz — Regional Vice President
Current Roles
Cowles Wealth Management — Founder
Medigap Plans of America — Owner & Managing Director
Global Health Benefits — Owner & Managing Director
GreatFlorida Insurance of Juno Beach — Owner
Credentials & Designations
AWMA® Accredited Wealth Management Advisor
RICP® Retirement Income Certified Professional
CRPC™ Chartered Retirement Planning Counselor
About

Nearly Three Decades Answering the Question That Matters Most

Kris Cowles — better known as The Retirement Income Guru — has spent nearly three decades helping people answer one of life's biggest questions: "How do I turn my savings into a paycheck that lasts?"

Full disclosure — Kris hasn't retired himself (he's having too much fun for that). But since the late 1990s, he's worked almost exclusively with retirees and those on the doorstep of retirement. Along the way, he's guided thousands through the transition, helping them make sense of Social Security, navigate the maze of Medicare, and — most importantly — build retirement income strategies tailored to their lives, not someone else's spreadsheet.

Kris's approach blends real-world experience with a healthy dose of practicality. After starting his career opening an investment office with Edward Jones, he went on to leadership roles with major firms like INVESCO, ING, and Allianz. Eventually, he traded the corporate world for something better: independence, and the ability to put clients first — every time.

Today, through his various firms, Kris works with clients across the country, focusing on clear, personalized strategies designed to address the real risks retirees face — longevity, market swings, taxes, and the fear of running out of money. He's also trained hundreds of financial professionals on how to do the same.

"Retirement isn't about having the biggest pile of money — it's about having a plan that lets you actually enjoy it."

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