The Great Wealth Transfer

"It will be such a great day when we don't have party politics at all and we just can elect independent American citizens to our government."

In this episode, Ali Katz talks with Brian Bengs, independent candidate for U.S. Senate in South Dakota, Navy veteran, retired Air Force JAG officer and former Wind Cave park ranger. They talk about what really happened in the C-SPAN press conference video, why he is running without a party in one of the reddest states in the country, and what a senator who caucuses with neither party could change.

In this episode:

• What happened at the press conference in the C-SPAN video, in Brian's own words

• Why he wants a pause on new AI data centers until there are federal guardrails

• Why voters stopped listening when he ran as a Democrat, and kept talking once he ran as an independent

• How an independent senator could work without caucusing with either party

• His proposal for a Medicare buy-in and a lower Medicare age

• What Ali, an estate planning lawyer, says would make people want to pay taxes

• Why he calls himself a Teddy Roosevelt Republican

Connect with Brian Bengs:

Website: https://bengsforsouthdakota.com

Substack: https://bengsforsouthdakota.substack.com

Instagram: https://www.instagram.com/brianbengs

Facebook: https://www.facebook.com/BBengs1970/

X: https://x.com/BrianBengs

Support a slate of independent candidates across the US who can win in 2026 here: independentswin.com

Resources:

Free Resource: Join Ali's next live Estate Planning Masterclass to learn how to make sure your will, trust, or estate plan truly works for you and the people you love. Register here: https://personalfamilylawyer.com/masterclass

Ali also publishes The Great Wealth Transfer Substack, with more resources linked from her website: https://alikatz.com/

Follow and subscribe to get notified of every new episode, and share this one with anyone who cares about government by and for the people.

Connect with Ali Katz:

Instagram: https://www.instagram.com/thealikatz

Facebook: https://www.facebook.com/TheAliKatz/

LinkedIn: https://www.linkedin.com/in/thealikatz/

Website: https://alikatz.com/

We inherited a two-party system, but we do not have to pass it on.

In this solo episode, Ali Katz talks about the inheritance that does not show up in a will: a two-party system she says does not represent us. She argues this is not a Republican problem or a Democrat problem, it is the same problem, and she explains what independent, corruption-free candidates could change in the midterms on November 3.

In this episode:

• Why legacy is more than what is in your will

• Why Ali says the problem is the system both parties share, not one party

• Ali's proposal for a 'corruption-free' commitment for independent candidates

• How Ali believes a small number of independents could create a powerful 'fulcrum caucus'

• What the four-minute mile has to do with independent candidates

• Why Ali says this is not about a spoiler vote

• What to look for in any candidate: transparent, accountable, participatory government

Resources

Free Resource: Join Ali's next live Estate Planning Masterclass to learn how to make sure your will, trust, or estate plan truly works for you and the people you love. Register here: https://personalfamilylawyer.com/masterclass

Ways to support independent candidates: https://independentswin.com

Ali also publishes The Great Wealth Transfer Substack, with more resources linked from her website: https://alikatz.com/

Follow and subscribe to get notified of every new episode, and share this one with someone who feels they don't have real representation.

Connect with Ali Katz:

Instagram: https://www.instagram.com/thealikatz

Facebook: https://www.facebook.com/TheAliKatz/

LinkedIn: https://www.linkedin.com/in/thealikatz/

Website: https://alikatz.com/

I know how to make money, but what happens when money doesn't matter?

In this episode, Ali Katz talks with Ryan Levesque, creator of the ASK Method and author of Return to Real. Ryan was days away from signing a $70 million deal to sell the majority of his company when Russia invaded Ukraine, interest rates spiked, and every buyer in the market walked away. What came after was a permaculture course in Vermont, one question he couldn't answer, and a family farm. Together they get into why the next decade may belong to trust instead of attention, what AI changes for lawyers and advisors, and what families with $1 million to $30 million actually need to steward what they have.

In this episode:

• The question Ryan asked himself after a $70 million deal fell through, and why the answer was a farm

• What a $50-a-week grocery budget taught him about the fear of losing it all

• Why Ryan believes the next decade belongs to oxytocin, not dopamine

• The "double craving": why what you're starving for is the same thing your market wants

• Why AI makes the legal document cheap and real counsel more valuable

• Why families with $1 million to $30 million end up with advice that falls apart when they need it

• How to start the end-of-life conversation with your parents while there's still time

Connect with Ryan Levesque:

Return to Real (special hardcover edition): https://returntorealbook.com

The Digital Contrarian newsletter: https://thedigitalcontrarian.substack.com

Instagram: https://www.instagram.com/askryanlevesque/

LinkedIn: https://www.linkedin.com/in/ryanlevesque/

Website: https://ryanlevesque.net

Free Resource: Join Ali's next live Estate Planning Masterclass to learn how to make sure your will, trust, or estate plan truly works for you and the people you love. Register here: https://personalfamilylawyer.com/masterclass

Ali also publishes The Great Wealth Transfer Substack, with more resources linked from her website: https://alikatz.com/

Follow and subscribe to get notified of every new episode, and share this one with your parents or your adult kids to start the conversation.

Connect with Ali Katz:

Instagram: https://www.instagram.com/thealikatz

Facebook: https://www.facebook.com/TheAliKatz/

LinkedIn: https://www.linkedin.com/in/thealikatz/

Website: https://alikatz.com/

You've been trying to have the inheritance conversation with your parents, and it's not going well. Or you're afraid it won't.

In this solo episode, Ali Katz breaks down why that conversation keeps stalling or backfiring, and lays out the three things that actually rebuild trust: commitment, curiosity, and collaboration. She gets personal about the resentment and judgment she had to work through with her own mother before she could commit to caring for her, and walks through a real example from her podcast conversation with Keith and his dad, where getting curious about why he "liked worrying" changed the entire tone of the conversation. She closes with why this work matters right now, in the middle of what she calls a meta crisis, and how staying in connection with her own mom, even when fear or protectiveness still shows up, has built the best relationship they've ever had.

In this episode:

• Why the inheritance conversation with your parents keeps stalling or backfiring

• The three-part trust framework: commitment, curiosity, collaboration

• What real commitment to your parents actually requires

• How to bring curiosity instead of assumption into the conversation

• Why collaboration means giving your parents the partnership you wished you'd had as a teenager

• What Ali's own relationship with her mom teaches about staying in connection

Free Resource: Join Ali's next live Estate Planning Masterclass to learn how to make sure your will, trust, or estate plan truly works for you and the people you love. Register here: https://personalfamilylawyer.com/masterclass

Ali also publishes The Great Wealth Transfer Substack, with more resources linked from her website: https://alikatz.com/

For Lawyers: Curious about building or growing an estate planning practice you actually love? Explore this training for attorneys and hear how lawyers are creating more predictable, relationship-centered practices through the Personal Family Lawyer® model. Register here: https://go.newlawbusinessmodel.com/event-w-2026-09-08?hsCtaAttrib=218711726217

Follow and subscribe to get notified of every new episode, and feel free to share this one with a sibling, a friend, or even a parent, to let them know you're showing up.

Connect with Ali Katz:

Instagram: https://www.instagram.com/thealikatz

Facebook: https://www.facebook.com/TheAliKatz/

LinkedIn: https://www.linkedin.com/in/thealikatz/

Website: https://alikatz.com/

I was featured on a hater website for nearly ten years. Not a single post, not a single comment. A full website.

In this solo episode, Ali Katz gets personal in a way she hasn't in years. She goes back to 2011, when she discovered an entire website dedicated to attacking her, calling her a scammer, a bad mom, a slut, and tracks how it shaped her, her daughter, and the years she spent staying quiet about the vulnerable parts of her story. She shares what she learned about telling the difference between criticism that's actually true and criticism that's just noise, what it cost her teenage daughter to have friends' parents already forming opinions about her mother, and why she's choosing now to bring all of herself forward again, even though it's scary.

In this episode:

• Why a decade on a hater website became one of the biggest lessons of her life

• How to tell the difference between criticism that's true and criticism that's just noise

• What it cost her daughter when the internet already "knew" her mother before meeting her

• Why she went quiet about the vulnerable parts of her story for years

• The real reason she's choosing to bring all of herself forward again

Free Resource: Join Ali's next live Estate Planning Masterclass to learn how to make sure your will, trust, or estate plan truly works for you and the people you love. Register here: https://personalfamilylawyer.com/masterclass

Ali also publishes The Great Wealth Transfer Substack, with more resources linked from her website: https://alikatz.com/

For Lawyers: Curious about building or growing an estate planning practice you actually love? Explore this training for attorneys and hear how lawyers are creating more predictable, relationship-centered practices through the Personal Family Lawyer® model. Register here: https://go.newlawbusinessmodel.com/event-w-2026-09-08?hsCtaAttrib=218711726217

Follow and subscribe to get notified of every new episode, and share this one with someone building something of their own.

Connect with Ali Katz:

Instagram: https://www.instagram.com/thealikatz

Facebook: https://www.facebook.com/TheAliKatz/

LinkedIn: https://www.linkedin.com/in/thealikatz/

Website: https://alikatz.com/

My company New Law Business Model made the Inc. 5000 for the seventh time. But the biggest lessons I've learned came from the two years we didn't make it.

In this episode, Ali Katz breaks down what happened in 2022, when her company hit $8 million in revenue but came within two weeks of missing payroll, and traces it back to seven specific ways she'd abdicated her own leadership without realizing it. From delegating tasks instead of ownership to handing out titles nobody had earned yet, she walks through each lesson with the real cost attached, then closes with the bigger picture: filing bankruptcy in 2012, and choosing seven years later to apply these lessons instead of repeating the same mistake.

In this episode:

• Why delegating ownership for an outcome beats delegating a list of tasks

• Why giving someone a title they haven't earned sets them up to fail, and leaves them nowhere to grow

• Why reporting is visibility into your numbers, not admin work

• Why you can't run your company if you can't read your own numbers

• Why you should believe people's actions over the values statements they recite

• Why your energy, not your time or money, is your number one asset

• Why building with the people you love works, if you've followed the six lessons before it

Free Resource: Join Ali's next live Estate Planning Masterclass to learn how to make sure your will, trust, or estate plan truly works for you and the people you love. Register here: https://personalfamilylawyer.com/masterclass

Ali also publishes The Great Wealth Transfer Substack, with more resources linked from her website: https://alikatz.com/

For Lawyers: Curious about building or growing an estate planning practice you actually love? Explore this training for attorneys and hear how lawyers are creating more predictable, relationship-centered practices through the Personal Family Lawyer® model. Register here: https://go.newlawbusinessmodel.com/event-w-2026-09-08?hsCtaAttrib=218711726217

Follow and subscribe to get notified of every new episode, and share this one with someone building something of their own.

Connect with Ali Katz:

Instagram: https://www.instagram.com/thealikatz

Facebook: https://www.facebook.com/TheAliKatz/

LinkedIn: https://www.linkedin.com/in/thealikatz/

Website: https://alikatz.com/

The Washington Post just told thousands of American families something they didn't want to hear. Ali Katz read the same numbers and found the one thing missing from every story in that article.

In this solo episode, Ali breaks down a Washington Post investigation that tracked real families from their early 50s until death: the share of people left with nothing to pass on after paying for eldercare has nearly doubled, and 1 in 20 spent more than $100,000 out of their own life savings. She tells the story of an Ohio man whose 96-year-old mother has been in assisted living for seven years at $15,000 a month, a family now facing the loss of a Kentucky farm that's been theirs since the 1960s. Then she names what every family in that article was missing: a legal window that closes long before anyone feels a crisis coming, and the specific tools, an irrevocable trust, a steward's trust, spousal protections, a real power of attorney, that could have kept it from happening.

In this episode:

• Why the number of families left with nothing after paying for elder care has nearly doubled

• What happened to one family's Kentucky farm, and the exact tool that could have saved it

• The five-year window that decides whether Medicaid will ever pay for your care

• What a Medicaid asset protection trust or a steward's trust actually protects, and what it costs you to use one

• What a well spouse is legally allowed to keep when the other needs long-term care

• The 1993 rule that lets the state claim your house after you're gone, even after you thought you were safe

• Why "the talk" with your parents or your kids matters more than any document you sign

Free Resource: Ali is going deeper on asset protection and elder care planning on her next live masterclass. Register here: https://personalfamilylawyer.com/masterclass

Additional Resource: More on long-term care planning and the steward's trust is available on Ali's website: https://alikatz.com/

Follow and subscribe to get notified of every new episode, and share this one with somebody you love.

Connect with Ali Katz:

Instagram: https://www.instagram.com/thealikatz

Facebook: https://www.facebook.com/TheAliKatz/

LinkedIn: https://www.linkedin.com/in/thealikatz/

Website: https://alikatz.com/

You're not bad with money. It's just the way the system is designed, and the people who have the most often have it the worst.

In this solo episode, Ali Katz names the term she coined for the feeling of never having enough regardless of the number in your account: money dysmorphia. She traces it back to feeling broke at six figures and still broke running 2x Million Dollar businesses, then breaks down why the system is built to extract from you rather than serve you, drawing on ideas from her friend Lisa Peterson (CFP, author of Mindful Money) and her longtime teacher Charles Eisenstein. From there she gets practical: how little you actually need to love your life, the LIFT meeting cadence (Legal, Insurance, Financial, Tax) she runs weekly, monthly, quarterly, and annually, and why $27 trillion sitting in retirement accounts is more within your control than most people think.

In this episode:

• What money dysmorphia is, and why it hits people at every income level

• How the system is designed to extract from you, even the things that used to be free

• The key to liberation: figuring out how little you actually need to love your life

• How to earn what you need in alignment with your values instead of chasing "enough"

• The LIFT meeting cadence: weekly, monthly, quarterly, and annual money check-ins

• Why $27 trillion in retirement accounts is more within your control than you've been told

Free Resource: Ali's going deeper on how to become a steward of your family wealth on her next live masterclass. Register here: https://personalfamilylawyer.com/masterclass

Free Resource: Get her Inheritance Guide — practical guides on what's actually transferring, and how to talk about it: https://www.alikatz.com

"It's not that you're bad with money. It's that the system has been designed to make you think that you are." — Ali Katz

"The key to your liberation is identifying how little you need to love your life." — Ali Katz

Follow and subscribe to get notified of every new episode, and share this one with someone who needs to hear it too.

Connect with Ali Katz:

Instagram: https://www.instagram.com/thealikatz

Facebook: https://www.facebook.com/TheAliKatz/

LinkedIn: https://www.linkedin.com/in/thealikatz/

Website: https://alikatz.com/

Dan Martell just posted about a $3.6 billion exit. Ali Katz read it and asked one question nobody else did: whose name was that investment actually in?

In this solo episode, Ali uses Dan Martell's Intercom exit as the entry point into a mistake most people make without realizing it, holding growing assets in their own name instead of protecting them as they grow. She gets personal about what that mistake cost her: a handshake deal with an employee that turned into a lawsuit, ten thousand dollars out of pocket immediately, and fifty thousand more in legal fees before it was over. From there she breaks down the numbers on estate tax (an exemption that's been as low as $675,000 and a rate that's hit 77%) and introduces the "steward's trust," an irrevocable trust structure that protects an asset for generations without handing over control.

In this episode:

• Why growing your assets makes you a target for lawsuits, creditors, and predators

• What a handshake deal gone wrong actually cost her, dollar for dollar

• How to grow an asset completely outside your taxable estate

• Where the estate tax exemption and rate have really been, and where they could go

• What a "steward's trust" is, and how it protects assets without giving up control

• How to turn an irrevocable trust into a training ground for the next generation

Free Resource: Ali is going deeper on asset protection and the steward's trust on her next live masterclass. Register here: https://personalfamilylawyer.com/masterclass

"Once people see that you're making money, they see you as prey." — Ali Katz

"The trust becomes an educational tool, not just a legal one." — Ali Katz

Follow and subscribe to get notified of every new episode, and share this one with someone who's building something worth protecting.

Connect with Ali Katz:

Instagram: https://www.instagram.com/thealikatz

Facebook: https://www.facebook.com/TheAliKatz/

LinkedIn: https://www.linkedin.com/in/thealikatz/

Website: https://alikatz.com/

Keith Alpert spent most of his life with almost no view into his family's wealth — until a single conversation turned him into the full-time steward of his father's estate. Six years, and one $100 trillion generational wealth transfer later, Keith opens up about what it actually takes to manage a family fortune: the week-long inventory that started it all, the "gold digger" email that blew up trust in his own family, and the exact conversation he now recommends every adult child have with their parents before it's too late.

In this episode, you'll learn:

• Why the first real step toward family wealth stewardship is a full inventory, not a will — and what happens if you skip it

• How to open the estate-planning conversation with your parents without it reading as "what's in it for me"

• The real story of a "caring" email that got read as greed — and cost a family its trust

• Why "he wanted to create family security" is a stronger reason to plan than fear of dying

• How to raise financially capable adult kids without doing the work for them

• The "bucket" system for managing cash and investments across three generations at once

• Why timing the market matters less than knowing your own risk tolerance and time horizon

Guest — Keith Alpert

Instagram — @rockinout68: https://www.instagram.com/rockinout68/

LinkedIn — /in/keithalpert: https://www.linkedin.com/in/keithalpert/

More From Ali Katz

Instagram — @thealikatz: https://www.instagram.com/thealikatz

Facebook — The Ali Katz: https://www.facebook.com/TheAliKatz/

LinkedIn — /in/thealikatz: https://www.linkedin.com/in/thealikatz/

Website: https://alikatz.com/

Free Resource: Get my Inheritance Guide — practical guides on what's actually transferring, and how to talk about it: https://www.alikatz.com

Join Ali Katz's free estate planning masterclass to learn essential strategies for protecting your assets and ensuring your family's future: https://personalfamilylawyer.com/masterclass