I recently sat down with Scott (39) and Wendy (38)—a successful entrepreneur couple with two young kids who’ve done a fantastic job building wealth. With over $1 million in net worth and strong earning years behind them, they’ve checked a lot of financial boxes most people only dream of.
But that success came with a surprising side effect: stress.
“We’ve done a great job planning for the most part,” Scott told me. “But I stopped focusing on cash flow and budgeting because we’d already built up our net worth.”
Like many high-achieving families, they let their guard down once things felt “comfortable.” A few great years and the feeling of financial security slowly led to lifestyle creep. They were still investing, still growing—but monthly cash flow had drifted into break-even territory or even dipped negative at times. And that started to weigh on them.
Here’s a quick look at their current picture:
$650K in real estate (LLC #1)
Income generated through their business (LLC #2)
$400K home with a $240K mortgage at 5.5%
$220K in brokerage accounts, $51K in Roth IRAs
$40K in cash
$30K in car loans, $22K in student loans
Their combined gross income is around $175K. After taxes, that’s about $131K—yet they spent $129K last year (including investments). In short, there wasn’t much wiggle room.
This isn’t unusual. Many families with solid net worth and strong earnings find themselves anxious about monthly cash flow. The problem isn’t their success—it’s the assumption that more money means fewer money decisions.
Here’s what I told Scott and Wendy: No matter how much you earn or how much you’ve built, you still need to tell your money where to go. Cash flow doesn’t take care of itself. I work with high achieving entrepreneur families across the Southeast to create clarity and confidence in their financial lives, especially when they’re navigating transitions, growing businesses, or juggling the demands of career and kids.