I sat down again with Cristian Mundy, a certified financial planner and senior wealth manager working with professional athletes and entertainers.

Cristian broke down how a first big paycheck isn't the finish line, it's the start of a whole new game, and how spending becomes permanent even when the income isn't.

We talked taxes nobody budgets for, why surrounding yourself with the wrong people can be more dangerous than signing a bad contract, and why athletic discipline doesn't automatically translate into financial discipline.

What's the first thing you'd do if a big check landed in your account tomorrow?

I almost bought a camera I didn’t need.

And the only thing that stopped me wasn’t discipline, budgeting, or some amazing financial habit.

It was friction.

After a recent filming trip to Napa Valley, I convinced myself I needed a new camera. I had the use case. I had the specs picked out. I had the business justification. I was ready to buy it.

Then the seller made it slightly harder for me to pay.

That tiny inconvenience gave me enough time to go home, look at the gear I already owned, and realize something:

I didn’t need the camera.

In this episode of Growing Money, I talk about why making spending TOO easy can work against us, how we turn wants into “needs,” and why intentionally adding friction back into your financial life might save you more money than relying on willpower.

I also share the simple 48–72 hour rule I’m trying to use before bigger purchases and the opportunity-cost question that completely changed how I looked at this one:

Would I rather have another camera… or a plane ticket that could actually help me grow my business?

Sometimes the smartest financial decision isn’t “never.”

It’s just: not now.

Let me know in the comments: What’s something you almost bought, or actually bought, because you convinced yourself you “needed” it?

I sat down with Adam Van Deusen from Kitces.com to talk about something we don't discuss enough in personal finance: what "enough" actually means for you.

We got into why so many people worry they'll never have enough to retire, even when they're doing the right things, and why comparing yourself to influencers or the next tax bracket is a losing game.

We talked about the arrival fallacy, why hitting your number doesn't automatically make you happy, and how to actually give yourself permission to spend money you worked hard to save. I loved his take on buying back your time instead of just buying more stuff.

What does "enough" actually look like for you right now?

I sat down with Jack Heintzelman, partner at Altara Wealth and board member of the Financial Planning Association.

We went way past budgets and spreadsheets into what money actually means to people, why couples avoid the money talk until it blows up their relationship, and why the $2M client and the $20M client are often losing sleep over the exact same fears.

Jack broke down why the most powerful financial habits are the boring ones, why compound interest beats chasing hot investments, and how one simple net worth statement can pull you out of feeling overwhelmed.

What's one money habit you've built that's completely changed your financial life?

In this episode of Growing Money, I sit down with Shannah Game to talk about the side of personal finance that spreadsheets can’t explain: our emotions, identity, habits, and deeply rooted beliefs about money. We explore why someone can have plenty of money and still feel financially unsafe, why so many of us constantly think, “I should be further ahead by now,” and how childhood experiences can continue shaping our financial decisions decades later.

We also talk about money guilt, emotional spending, defining what “enough” actually means, and why earning more isn’t always the answer. Shannah explains how our bank accounts can change much faster than our nervous systems and why small experiments may be more effective than trying to completely overhaul our financial lives overnight.

We also get into career changes, comparison, personal growth, and giving yourself permission to step outside the box you’ve built around money and success.

What money belief have you carried for years that you’re starting to realize might not actually be yours?

In this episode, I sit down with Robert Dillard, an insurance and special needs planning specialist who works alongside financial planners, estate attorneys, and CPAs to help families protect what matters most.

Robert opens up about growing up in a broken, low-income household, living with autism, ADHD, dyslexia, and dysgraphia himself, and raising a nonverbal autistic son who requires round-the-clock care.

He shares the gut-wrenching story of his mother's term life policy lapsing just three days before she passed away, and how that moment shaped his entire career.

What's one financial conversation you've been putting off with your family?

What if you could go back 20 years and make better money decisions?

I ran into an old college friend while I was out filming at a winery, and our conversation got me thinking about Back to the Future, Hot Tub Time Machine, and one question that hits a lot harder as you get older: what would you actually change if you could go back?

I wouldn’t want to rewrite my life. I love my wife, my daughter, and the journey that got me here. But financially? There are absolutely decisions I would make differently.

In this episode of Growing Money, I talk about protecting your future self by making better decisions today. You don’t need to know what the next Apple, Google, or Amazon will be. You don’t have to make perfect financial decisions either. But small choices made consistently over time can completely change where you end up.

I talk about investing early, diversification, building equity through business ownership, increasing your income, spending less than you make, and some of my own financial mistakes, including student loan debt. I also explain why I don’t believe financial freedom means never buying another latte. The goal is to build a financial life strong enough that buying one doesn’t matter.

This is also the beginning of a new direction for Growing Money. Over the next 52 weeks, I’m going to explore how we can earn more money, keep more of what we earn, invest intelligently, build ownership, avoid costly mistakes, and create a richer life without pretending any of us have all the answers.

I’m figuring this out too.

And I want to bring you along for the journey.

In this episode, I sit down with George Burnett, Director of Philanthropic Consulting and Wealth at Callan Family Office, to talk about what happens after you build wealth and why the hardest part often has nothing to do with investment returns.

We get into generational wealth, estate planning, wealth transfer, philanthropy, family communication, and the money anxiety that can exist at every level of financial success. George explains why families can spend decades accumulating wealth but wait until the last minute to plan what happens next, and why communication may matter even more than the legal documents themselves.

We also explore the danger of chasing more without remembering why you wanted financial success in the first place, how scarcity can affect even ultra-wealthy families, and why a strong financial plan should create a “floor” of stability for the people you love.

Ultimately, this conversation is about building a legacy measured not just by money, but by relationships, intention, impact, and what you leave behind.