Generational Gains

What if you have retirement money sitting in an old 401(k) or IRA — and you don’t even realize what you can do with it?

In Episode 50 of Generational Gains, Greg and Carson Herlean break down one of the most misunderstood areas of retirement investing: self-directed IRAs and old retirement accounts.

Greg shares the story of someone who learned years ago that he could self-direct a portion of his IRA. He eventually moved roughly $200,000 from a traditional retirement account and invested it into a storage-unit deal. Over approximately three years, that investment produced about $127,000 in gains.

The bigger lesson isn’t the individual investment — it’s understanding the options you may already have.

Millions of people change jobs and leave behind retirement accounts without ever revisiting them. Others know the account exists but assume their only option is investing in the traditional menu of stocks, mutual funds, and other publicly traded investments.

Greg and Carson explain how a self-directed IRA can allow certain investors to move some or all of eligible retirement funds into alternative investments they understand and want more control over.

In this episode:

• How to find old 401(k)s and retirement accounts
• What a self-directed IRA actually is
• How self-directed IRA custodians work
• Traditional investments vs. alternative assets
• Using retirement funds to invest in certain types of real estate
• Why you don’t have to move your entire retirement account
• Important restrictions and prohibited transactions to understand
• Why self-directed investing is NOT right for everyone
• The importance of doing your own due diligence
• How taking control of even a small percentage of your retirement assets can expand your options

Greg also explains that self-directed does not mean you can invest in absolutely anything. There are important restrictions, including rules involving disqualified persons and certain prohibited asset types.

The goal isn’t to tell everyone to abandon the stock market or move 100% of their retirement savings into alternative assets.

It’s to understand your options.

For some people, that may mean keeping most of their retirement money where it is while self-directing 5%, 10%, 25%, or another amount they’re comfortable with into investments they know and understand.

The first step may simply be asking:

Do I have an old retirement account somewhere — and am I using it the way I want to?

Subscribe to Generational Gains for conversations about money, retirement, investing, entrepreneurship, and building long-term wealth across generations.

Watch the full video episode on Greg's YouTube Channel here: https://www.youtube.com/@gregherlean

Follow and connect with Greg on IG: https://www.instagram.com/gregherlean/

Check out Greg's website here: https://www.gregherlean.com/

Carson's IG: https://www.instagram.com/c.herlean/

Carson's TikTok: https://www.tiktok.com/@carsonherlean

You can spend 30 years building your retirement nest egg and still run into serious trouble in the first few years after you stop working.

In Episode 49 of Generational Gains, Greg and Carson Herlean break down one of the most overlooked parts of retirement planning: how to turn the money you’ve accumulated into reliable income without running out.

Most retirement conversations focus on getting “up the mountain” — saving, investing, growing your net worth, and reaching a target number.

But what happens when it’s time to come back down?

Carson explains why two retirees can start with the exact same amount of money, earn similar long-term returns, and have completely different outcomes depending on when market downturns happen. One retiree may continue growing wealth, while another can deplete their assets much earlier simply because the bad years came at the wrong time.

In this episode, Greg and Carson discuss:

• Why the first few years of retirement are so important
• The difference between accumulation planning and income planning
• Why reaching your “retirement number” is only half the plan
• How market volatility can impact retirement withdrawals
• Why traditional withdrawal strategies may force retirees to take less income
• The importance of having a separate income cushion during down markets
• Carson’s four-part retirement framework: Cushion, Convert, Cash Flow, and Cover
• How retirement planning changes when you start thinking about distributions instead of just growth
• Other retirement risks including longevity, healthcare costs, taxes, and required distributions

The core idea is simple: you shouldn’t spend decades preparing to retire and then leave your retirement income up to chance.

A complete retirement plan should help you both get up the mountain and safely get back down.

Greg and Carson also announce an upcoming free retirement education series where they’ll go deeper into retirement income planning, insurance strategies, self-directed retirement accounts, and protecting your income throughout retirement.

Watch the full video episode on Greg's YouTube Channel here: https://www.youtube.com/@gregherlean

Follow and connect with Greg on IG: https://www.instagram.com/gregherlean/

Check out Greg's website here: https://www.gregherlean.com/

Carson's IG: https://www.instagram.com/c.herlean/

Carson's TikTok: https://www.tiktok.com/@carsonherlean

AI is changing the way we learn, work, build businesses, and potentially even how we define success.

In Episode 48 of Generational Gains, Greg and Carson Herlean debate what they would do if they were 20 years old today with artificial intelligence at their fingertips, and whether the traditional path of college, a career, buying a home, and building the “American Dream” still makes sense.

They explore the line between using AI as a powerful tool and using it as a shortcut. Can AI make you dramatically more productive and creative, or are people becoming dependent on it and losing the ability to think for themselves?

The conversation then turns to one of the biggest questions facing young people today: Is college still worth it?

Greg and Carson discuss why experience, relationships, real-world skills, entrepreneurship, and the ability to use AI may increasingly matter just as much, or more, than a traditional degree in many careers.

In this episode:

• How Greg is implementing AI inside his business
• Whether AI makes us smarter or lazier
• Why the people who master AI could have a massive advantage
• How AI is already changing education
• Whether spending four years in college still makes sense
• College vs. entrepreneurship and real-world experience
• Why hustle still matters even with AI
• How hiring could change in an AI-driven economy
• Whether the traditional American Dream is becoming harder to achieve
• Why every path to success still requires time, sacrifice, and failure

AI may make things faster, but Greg and Carson argue that it doesn’t eliminate the need to work, learn, take risks, and actually apply what you know. As Greg puts it, the people who combine AI with relentless execution could end up miles ahead of everyone who refuses to adapt.

Subscribe to Generational Gains for conversations about money, entrepreneurship, business, investing, family, and building wealth across generations.

Watch the full video episode on Greg's YouTube Channel here: https://www.youtube.com/@gregherlean

Follow and connect with Greg on IG: https://www.instagram.com/gregherlean/

Check out Greg's website here: https://www.gregherlean.com/

Carson's IG: https://www.instagram.com/c.herlean/

Carson's TikTok: https://www.tiktok.com/@carsonherlean

The economy has slowed, real estate investors are feeling the pressure, and many business owners are searching for ways to free up cash flow and survive the next six to twelve months.

In Episode 47 of Generational Gains, Greg and Carson Herlean discuss what they are currently seeing in the real estate market, why fix-and-flip margins have become increasingly difficult, and how strategies such as velocity banking may help some people manage debt and cash flow more efficiently.

They also explore one of the biggest decisions an entrepreneur can make: choosing a business partner.

A strong partnership can provide capital, clients, expertise, accountability, and the missing skill set needed to grow. The wrong partnership can create resentment, financial losses, and a painful business breakup.

Greg shares lessons from decades of partnerships, including why you should test a working relationship before committing, choose someone whose strengths complement your weaknesses, listen to trusted mentors and your spouse, and avoid automatically splitting a company 50/50.

This episode covers:

• What Greg and Carson are currently seeing in the economy
• Why real estate deals are taking longer and producing smaller margins
• How velocity banking may improve cash-flow flexibility
• When partnering with someone can help a struggling business
• The warning signs of a bad business partnership
• Why complementary skills matter more than friendship
• How to test a partnership before making it official
• Why taking action beats endlessly preparing

Whether you are starting a company, navigating a difficult market, managing debt, or considering bringing on a partner, this conversation offers practical lessons from two generations of entrepreneurs.

Subscribe to Generational Gains for conversations about money, business ownership, real estate, retirement, and building lasting family wealth.

Watch the full video episode on Greg's YouTube Channel here: https://www.youtube.com/@gregherlean

Follow and connect with Greg on IG: https://www.instagram.com/gregherlean/

Check out Greg's website here: https://www.gregherlean.com/

Carson's IG: https://www.instagram.com/c.herlean/

Carson's TikTok: https://www.tiktok.com/@carsonherlean

In Episode 46 of Generational Gains, Greg and Carson break down the biggest takeaways from their live webinar on retirement income planning and the strategy Carson calls the Volatility Buffer.

Most people insure their car, home, and life — but never insure their retirement income.

In this episode, they discuss why market volatility can destroy retirement income, how whole life insurance can be structured as a protected income buffer, why the traditional “just invest and withdraw” model may not be enough, and how this strategy can work alongside self-directed IRAs, real estate, and other assets.

If you’re preparing for retirement or want more control over your income, this episode is for you.

Watch the full video episode on Greg's YouTube Channel here: https://www.youtube.com/@gregherlean

Follow and connect with Greg on IG: https://www.instagram.com/gregherlean/

Check out Greg's website here: https://www.gregherlean.com/

Carson's IG: https://www.instagram.com/c.herlean/

Carson's TikTok: https://www.tiktok.com/@carsonherlean

In this episode of Generational Gains, Greg and Carson break down their biggest takeaways from a recent Boardroom mastermind with over 250 business owners from around the country.

From real estate and lending to entrepreneurship, AI, profitability, and the economy, this conversation dives into what successful people are actually seeing behind the scenes right now.

In this episode, we talk about:

• Why profitability is harder than most people think
• What business owners are really dealing with in today’s economy
• Why many successful people are still feeling pressure
• How tighter lending is affecting deals and growth
• Why some investors are preparing for major buying opportunities
• What AI is already doing inside businesses right now
• Why learning AI may become one of the most important career moves you can make
• The importance of faith, values, and community during hard seasons
• Why talking to your kids about money early matters more than ever

One of the biggest takeaways from this episode is simple:

Even successful people are being forced to adapt.

The market is changing. Lending is tighter. Profit is harder. And the people who win will be the ones who stay grounded, stay creative, and keep learning.

If you’re a business owner, investor, entrepreneur, or someone trying to better understand where things are headed, this episode will give you real-world perspective from people in the trenches.

Share this with someone building a business or trying to make smarter moves in this economy.

Watch the full video episode on Greg's YouTube Channel here: https://www.youtube.com/@gregherlean

Follow and connect with Greg on IG: https://www.instagram.com/gregherlean/

Check out Greg's website here: https://www.gregherlean.com/

Carson's IG: https://www.instagram.com/c.herlean/

Carson's TikTok: https://www.tiktok.com/@carsonherlean

In this episode of Generational Gains, Carson and Greg break down real conversations with clients this week — and the biggest investing mistake they see over and over again:

Going ALL-IN on one strategy

Whether it’s stocks, crypto, real estate, or even alternative assets… most people swing too hard in one direction — and pay for it later.

In this episode, we dive into:

• A real client with $800K in the stock market questioning what to do next
• Why going “all-in” (even on good investments) is risky
• Who self-directed investing is actually for (and who it’s NOT for yet)
• The ideal investment allocation strategy most people miss
• How to balance:
  • Stocks
  • Real estate / alternative assets
  • Safe, guaranteed assets (like life insurance)
• Why your strategy should change with your stage of life
• The difference between accumulation vs protection vs income planning

Key takeaway:

Wealth isn’t built by picking the “perfect investment”…

It’s built by creating the right mix of investments that can survive any market.

Who this is for:

• You have $75K–$500K+ saved and want to invest smarter
• You’re nervous about the market but don’t know what to do
• You’ve been told to “just stay in the market” but it doesn’t feel right
• You want more control, diversification, and protection

Want help building your own plan?

Reach out and we can walk through your numbers and show you exactly how this could look for you.

Watch the full video episode on Greg's YouTube Channel here: https://www.youtube.com/@gregherlean

Follow and connect with Greg on IG: https://www.instagram.com/gregherlean/

Check out Greg's website here: https://www.gregherlean.com/

Carson's IG: https://www.instagram.com/c.herlean/

Carson's TikTok: https://www.tiktok.com/@carsonherlean

In Episode 43 of Generational Gains, Greg and Carson break down one of the most overlooked parts of retirement planning:

Most advisors help you climb the mountain (accumulation)…

but almost nobody teaches you how to get back down safely (distribution).

That’s where the SAFE Method comes in — a strategy that uses a volatility buffer so you can keep income steady in retirement without being forced to sell assets when the market is down.

In this episode, we cover:

• The 2 phases of retirement: Accumulation vs Distribution
• Why market volatility is the real retirement killer
• The truth behind the 4% rule (and why it’s not as “safe” as people think)
• How newer research pushes that withdrawal rate closer to ~2.8–3%
• Why sequence-of-returns risk matters more than average returns
• How a SAFE account can let your growth assets recover during down years
• Why whole life insurance can be used as a non-correlated, liquid, guaranteed buffer
• A simple example of how the SAFE Method can improve outcomes with the same savings

The goal isn’t to “invest more.” It’s to allocate smarter — so your retirement income isn’t at the mercy of market timing.

If you want to see what this looks like with your numbers, we can run the math and show you how a SAFE plan could fit into your retirement picture.

Reach out to Carson to walk through it using your actual savings, timeline, and goals.

Watch the full video episode on Greg's YouTube Channel here: https://www.youtube.com/@gregherlean

Follow and connect with Greg on IG: https://www.instagram.com/gregherlean/

Check out Greg's website here: https://www.gregherlean.com/

Carson's IG: https://www.instagram.com/c.herlean/

Carson's TikTok: https://www.tiktok.com/@carsonherlean

In Episode 42 of Generational Gains, Carson walks through a real client’s Infinite Banking policy — showing exactly how it looks 3 years in, how it was originally illustrated, and how it’s actually performing today.

This is the part most people never see.

Instead of theory or sales language, this episode breaks down:

• What a whole life policy looks like after the early years
• Why Infinite Banking feels confusing in years 1–2
• What actually changes in Year 3 and beyond
• How paid-up additions (PUAs) create liquidity
• Why policy cash value begins growing faster than contributions
• The difference between guaranteed vs non-guaranteed values
• How dividends, cash value, and death benefit really work together
• Why Infinite Banking is a savings and banking system, not an investment

You’ll also see:

• Projected vs actual cash value and death benefit
• Why conservative illustrations often under-promise
• How this policy is already outperforming expectations
• Why banks fail — and insurance companies don’t
• How to use policy loans without interrupting growth

💡 Key Insight: Once a policy matures past the early years, every new dollar you put in becomes immediately usable — while still compounding for life.

This episode is especially valuable if:

• You already have a policy and want a refresher
• You’re 1–3 years in and questioning the process
• You want to see real numbers, not marketing slides
• You’re considering Infinite Banking but want proof

Watch the full video episode on Greg's YouTube Channel here: https://www.youtube.com/@gregherlean

Follow and connect with Greg on IG: https://www.instagram.com/gregherlean/

Check out Greg's website here: https://www.gregherlean.com/

Carson's IG: https://www.instagram.com/c.herlean/

Carson's TikTok: https://www.tiktok.com/@carsonherlean

In Episode 41 of Generational Gains, Carson shares his full personal story — how he went from a middle-class upbringing, losing money in the stock market, and questioning the traditional path… to building a repeatable wealth system centered around business ownership, Infinite Banking, and real estate.

This episode isn’t theory. It’s real life.

You’ll hear:
• Why Carson stopped investing in the stock market at 18
• How mentors like Chris Naugle and Justin Colby shaped his thinking
• Why he dropped out of college to pursue financial education
• How Infinite Banking became the foundation of his wealth strategy
• Why life insurance is his primary capital reservoir
• How he uses policy cash value to buy real estate
• How this system creates tax efficiency, liquidity, and control
• Why wealth is built through systems, not single investments

This episode is meant to be a case study — proof that these strategies aren’t abstract ideas, but real tools used by real people building real lives.

Core Lesson:
Wealth isn’t built overnight. It’s built by creating a system that produces income, stores capital safely, and reinvests it intentionally over time.

Have questions about Infinite Banking, starting a business, or building your own system?

Reach out to Carson, he is happy to connect.

Watch the full video episode on Greg's YouTube Channel here: https://www.youtube.com/@gregherlean

Follow and connect with Greg on IG: https://www.instagram.com/gregherlean/

Check out Greg's website here: https://www.gregherlean.com/

Carson's IG: https://www.instagram.com/c.herlean/

Carson's TikTok: https://www.tiktok.com/@carsonherlean