Episode 302: Self-Directed IRAs: The Retirement Strategy Nobody Told You About with Kaaren Hall

Self-directed IRA retirement planning guide for women entrepreneurs with alternative investment strategies

Look, I'm going to be real with you. Social Security isn't going to cut it when you retire. We all know this, right? Whether you're grinding away at a traditional job or building your own business, that government check is just the baseline. It's not enough.

 

Now, before you click away because retirement talk feels boring or overwhelming, stick with me. Because what I learned from Kaaren Hall in this episode actually got me excited about retirement planning. And honestly? I didn't think that was possible.

 

Here's what most of us don't know: There's a way to have actual control over your retirement money. Not just hoping your financial advisor picks the right mutual funds. Real control. And only 4% of people are doing it.

What the Heck is a Self-Directed IRA Anyway?

Okay, so traditional retirement accounts work like this: You put money in, someone else manages it, they pick from a menu of stocks and bonds, and they take a percentage of your money for doing it. Sometimes your employer throws in matching funds (which is awesome—free money!), and everything kind of sits there growing... or not growing... depending on the market.

 

A self-directed IRA flips this whole thing on its head.

 

YOU choose where your money goes. YOU pick the investments. And instead of someone taking a percentage of your assets, you pay a flat fee—like $35 per transaction. That's it.

 

When I sat down with Kaaren Hall, CEO of UDirect IRA Services, she broke it down so simply. The custodian isn't trying to sell you anything. They're holding the account and processing transactions based on what YOU decide to invest in.

 

"We're not getting paid on your asset at all. Maybe a $35 transaction fee, but not a percentage of your assets. You open an account, fund it by moving over those retirement accounts you already have, and then invest in what you want." - Kaaren Hall

 

Mind. Blown.

Only 4% of retirement funds are in self-directed accounts. That's $40 trillion in retirement money that most people don't even know they can control.

So What Can You Actually Invest In?

Here's where it gets really interesting. Kaaren calls these "alternative assets," but honestly, she made a great point—how is real estate "alternative" when we all live in houses and work in buildings? These investments feel way more real than watching stock tickers all day.

Real Estate (In Like, So Many Ways)

Rental properties, commercial buildings, land, real estate syndications, REITs. Your IRA can literally own property that generates rental income or grows in value over time.

 

Private Lending (Yes, You Can Be the Bank)

Your IRA can make secured or unsecured loans to people or businesses. They pay you back with interest, and all that money goes straight into your retirement account. Wild, right?

 

Precious Metals

Gold, silver, other commodities. Especially popular right now with everything feeling uncertain in the economy.

 

Cryptocurrency

Bitcoin, Ethereum, whatever digital assets you believe in. They can live inside your retirement account.

Private Equity in Businesses

This one really got me. Your IRA can own part of a business—from the nail salon where you get your manicures to bigger syndicated deals.

 

Supporting Small Businesses That Need Capital

Your IRA can be a debt or equity partner in businesses trying to launch or rebuild. This is huge for supporting other women entrepreneurs in your community.

 

 

And get this—the only requirement to contribute to ANY retirement account is having active income from a job. That's literally it. Your age and income affect how much you can put in, but the barrier to entry is just... having a job. Most of us have had jobs. Most of us qualify.

Why Women Entrepreneurs Need to Know This

Can we talk about how hard it is for women to get funding? Because it's ridiculous. Less than 2% of venture capital goes to women. Two. Percent. Meanwhile, we're starting businesses at incredible rates and often doing it with way less capital than our male counterparts.

 

But here's what Kaaren told me that changed everything: Retirement accounts represent a $40 trillion pool of money. TRILLION. With a T.

 

She shared this story about a woman who had no idea she could raise capital by asking people to invest through their IRAs. Once someone explained it to her, she raised millions. The only thing holding her back was not knowing she could ask.

 

"She said it just opened her eyes to realize she could ask. And suddenly she was raising millions of dollars. She acquired the confidence to do this." - Kaaren Hall

 

Think about that for a second. How many of us are out here feeling like we're alone in trying to fund our dreams? How many times have you thought, "Well, I can't get a bank loan, and I'm definitely not getting VC money, so I guess I'll just bootstrap forever"?

 

There's another way. And it's not just about your own business—you can help fund other women's ventures too.

Women receive less than 2% of venture capital funding. But retirement accounts hold $40 trillion. The money exists—you just need to know how to access it.

How to Actually Raise Capital Using Self-Directed IRAs

The Bigger Deals: Syndications

If you're raising larger amounts of capital, syndications are one route. Now, don't let that word scare you. Basically, you work with a syndication attorney (Kaaren knows a bunch and can make referrals) to create an SEC-approved offering. There are different types—Reg A, Reg D, and others—and they each have different rules about whether you can advertise publicly or how you can find investors.

 

Yes, you need an attorney. I know, I know—it's an expense. But Kaaren put it perfectly: "If you're going to play the game, you've got to put your big girl pants on." The money you spend on legal help upfront prevents massive problems later. Trust me on this one.

 

The SEC doesn't mess around, and you don't want to run afoul of their regulations. Get the help. It's worth it.

The Grassroots Approach for Smaller Needs

But what if you don't need millions? What if you just need help getting your business back on its feet after COVID wiped you out? Or you're that boutique owner who needs $50K to expand?

 

This is where it gets really beautiful and community-focused.

 

Remember all those empty storefronts you drove past during the pandemic? The nail salons that closed, the yoga studios that couldn't survive, the coffee shops that never reopened? Many of those owners wanted to come back—they just didn't have the capital.

 

Your IRA can help them. Seriously.

"Your IRA can be a debt or equity partner in her business. Who knew that? Who knew your IRA could do that? Nobody tells you this." - Kaaren Hall

Maybe you've been going to the same nail salon for years and you know the owner. She's trying to rebuild. Your IRA can invest in her business. Your neighbor needs a car loan but can't get one from the bank, and you know they're good for it? Your IRA can make that loan, and they pay it back to your retirement account with interest.

 

These micro-investments create real impact in your community while building your retirement. That's the kind of stuff that lights me up.

How Do You Even Get Started?

First: Educate Yourself (But Make It Easy)

Okay, so you're probably thinking, "Sarah, this sounds great, but when am I supposed to learn all this? I'm already working 12-hour days!"

 

Girl, I feel you. But here's Kaaren's genius advice: podcasts during your commute.
You're already driving, right? Your brain is in this perfect receptive state when you're driving—using both sides at once. And honestly, I've noticed this too. Whenever I listen to a podcast while driving, I remember it SO much better than if I'm listening while doing dishes or folding laundry.

 

She recommends BiggerPockets, Justin Donald's podcast, and other real estate and alternative investment shows. Pick one that doesn't make you want to fall asleep, and let it run. Over weeks and months, the information accumulates.

 

You don't need a finance degree. You need to use your drive time better than listening to the same Spotify playlist on repeat.

Connect with Real Humans

The other thing? Find local meetups. Go to Meetup.com and search for real estate investing groups in your area. Kaaren actually runs wine and cheese mixers in Orange County where investors meet people raising capital. How fun does that sound?

 

These aren't stuffy networking events. They're real people talking about deals, asking questions, learning from each other's mistakes. You can't get that kind of practical knowledge from a book.

The Actual Steps to Move Your Money

Alright, let's get tactical. Here's how you actually do this thing:

  1. Pick a self-directed IRA custodian (like UDirect IRA Services—there are others too)
  2. Open your account (there's paperwork, but it's not terrible)
  3. Roll over your existing retirement funds from old 401ks or IRAs
  4. Choose the specific investment you want
  5. Tell the custodian to make the investment from your IRA

 

Here's the important part: Do step 4 BEFORE steps 1-3. Know what you want to invest in first. Find the deal, understand the opportunity, THEN move your money into the self-directed account.

 

Oh, and if you're like me and you have three different retirement accounts from previous jobs sitting there doing nothing? You can consolidate all of them into one self-directed IRA. Boom—now you've got a bigger pool of money to work with.

Think in Layers (Your Capital Stack)

Kaaren talks about retirement planning like building a stack. I love this visual because it makes so much sense.

 

Your bottom layer is Social Security—the baseline we talked about. Then you've got life insurance, maybe an annuity. Your employer 401k with those matching contributions. Personal assets like your home. And finally, your self-directed retirement accounts where you have full control.

 

No single layer should be doing all the work. The whole point is that if one thing doesn't perform well or the market tanks or something unexpected happens, you've got other layers supporting you.

"It's not just the “me show” starring me trying to get this thing done. You can say, 'Hey, I'm doing this thing. Do you want to come along and have a debt or equity position in what I'm doing?'" - Kaaren Hall

This becomes extra important when the economy feels shaky. Having your money in different places—different asset types, different structures—protects your future no matter what happens.

Let's Talk About Taxes (I Promise This Won't Hurt)

Here's something your CPA will love: Contributions to retirement accounts are often tax-deductible.

 

Translation? You're paying yourself instead of paying the IRS. Every dollar you put into a retirement account is a dollar that doesn't get taxed this year. Your taxable income goes down. You keep more of your money.

 

Plus, the investments inside retirement accounts grow tax-advantaged. Traditional IRAs defer taxes until you withdraw the money. Roth IRAs let earnings grow tax-free if you follow the rules. Either way, you're way better off than investing in regular taxable accounts.

 

Kaaren wrote a whole book with BiggerPockets called The Bigger Pockets Guide to Self-Directed IRA Investing. It's not a story you read cover to cover—it's more like a guide where you flip to chapter five when you need to understand tax stuff or page twelve when you want to know contribution limits. Super practical.

The Rules You Need to Know

Okay, real talk: Self-directed IRAs have rules. The IRS isn't messing around with prohibited transactions and disqualified persons.

 

Basically, you can't use your IRA to benefit yourself or certain family members directly. So you can't live in a house your IRA owns. You can't hire yourself to manage a property your IRA bought. The investment has to stay separate from your personal stuff.

 

Working with a good custodian helps you stay on the right side of these rules. They're not just random bureaucratic nonsense—they exist to protect the tax-advantaged status of your account. Break the rules, and you could lose that status for your entire account. The penalties are no joke.

 

But here's the thing: Within those boundaries, you have SO much flexibility. You need to know where the lines are.

Why Doesn't Everyone Know About This?

If self-directed IRAs are so great, why do only 4% of people use them?

 

Simple answer: Nobody's telling us.

 

Think about it. Financial services companies make money by managing your assets and taking a percentage. They don't have a lot of incentive to say, "Hey, you could move this to a self-directed account where we make way less money off you."

 

Traditional retirement marketing is all about simplicity and professional management. Which, fair—those things are valuable for a lot of people. But it's not the only option, and most of us never hear about the alternatives.

 

Women especially get left out of these conversations. The same systems that give us 2% of venture capital also keep us in the dark about investment strategies like self-directed IRAs.

 

But you know what? That knowledge gap is also an opportunity. Learning this stuff puts you ahead of 96% of other people saving for retirement. You're accessing strategies most people will never discover.

This Is About Taking Care of Each Other

I love how Kaaren frames this. She talks about self-directed retirement planning as responsible care.

 

So many of us are caretakers—for our kids, our aging parents, our communities, our employees. Taking care of your own financial future means you won't become a burden to others later. You're not forcing your kids or your friends to step in and fill gaps you could have filled yourself.

"As women, a lot of us are caretakers, and we like to take care of ourselves. And in this way, we take care of others. When we take care of ourselves, we're not obligating others to step in and fill that gap that we didn't fill ourselves." - Kaaren Hall

That perspective shift? It's powerful. Building security for yourself isn't selfish—it's generous.

 

And right now, there's this massive wealth transfer happening toward women. Baby boomers are aging, passing assets down, and women are increasingly making the investment decisions. Understanding tools like self-directed IRAs means you can use that wealth effectively—not just for your own retirement, but for funding other women's businesses, supporting local economies, creating real community impact.

 

We need each other to be having these conversations.

Resources to Help You Learn More

Kaaren has some really helpful resources for getting started. I'm linking to all of them below because I want you to actually use them.

Free Report on Asset Classes

Download this (https://udirectira.com/free-report/) before you do anything else. It explains all the different types of alternative assets your IRA can hold. Super helpful for wrapping your head around what's even possible.

 

Grab the free report here

 

The Bigger Pockets Guide to Self-Directed IRA Investing

Find Your People Locally

 

Seriously, go to Meetup.com right now and search for real estate investment groups near you. The conversations you'll have with real investors are worth their weight in gold.

 

Start a Podcast Habit

BiggerPockets. Justin Donald. Find alternative investment educators who don't bore you to tears, and make them part of your commute. The information builds over time, I promise.

Start Today:

✓ Download the free asset class report
✓ Listen to one podcast episode on your commute
✓ Search Meetup.com for local investing groups
✓ Check what old 401ks you have sitting around
✓ Contribute to your retirement account this month

Your Next Step (Right Now)

You don't need to have everything figured out before you start.

 

If you've got old 401ks or IRAs sitting around from previous jobs, start researching self-directed IRA custodians. Download Kaaren's free report and see which asset classes interest you.

 

If you're already investing in real estate or other alternative assets with personal money, talk to someone about whether moving those into a tax-advantaged retirement account makes sense.

 

If you're trying to raise capital for your business, have a conversation with a syndication attorney about structuring an offering that lets people invest through their retirement accounts.

 

And honestly? Regardless of where you are in this journey, contribute to your retirement accounts today. Traditional or self-directed, doesn't matter—putting money away now creates security later. The tax benefits alone make it worthwhile.

Your retirement money can do more than sit in mutual funds. It can support investments you believe in. It can fund businesses that need capital. It can build community wealth while securing your own future.

 

That $40 trillion pool exists. Are you going to tap into it?

About Kaaren Hall

Kaaren Hall is the founder and CEO of uDirect IRA Services, LLC, a leading provider of self-directed IRA accounts since 2009. With over two decades of experience in real estate, mortgage lending, and property management (and especially Self-Directed IRAs), Kaaren has empowered thousands of people to take control of their retirement funds and invest in alternative assets, such as real estate, private lending, precious metals, and more.

 

Her expertise in self-directed retirement accounts has made her a sought-after speaker, and she has been a featured panelist and presenter at industry-leading conferences, including BiggerPockets' BPCON22, 23 & 24.
Kaaren is also the founder of OCREIA (Orange County Real Estate Investors Association), where she fosters a vibrant community of real estate investors through education and networking since 2012.

 

Adding to her accolades, Kaaren is now the author of the newly published Self-Directed IRA Investing: A BiggerPockets Guide, the definitive resource for investors looking to unlock the power of self-directed IRAs to build wealth. Published by BiggerPockets Publishing, this comprehensive guide combines actionable insights, real-world examples, and Kaaren's extensive industry knowledge to help investors confidently navigate the world of self-directed retirement accounts.

 

Beyond her professional achievements, Kaaren's entrepreneurial journey has enabled her to support meaningful charitable giving and inspire others to take control of their financial futures. She also serves on the Board of Directors for The Council on Aging Southern California as well as the board for RITA (the Retirement Industry Trust Association), where she continues to advocate for transparency and education in the retirement industry.

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About Sarah Walton

Sarah Walton is a business coach, podcast host, and mentor who helps women entrepreneurs build businesses they love. She's the creator of the Abundance Academy, Effortless Sales, and the Game On Girlfriend® podcast. Sarah's mission is to put more money in the hands of more women while teaching authentic, heart-centered business strategies.

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