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I Didn’t Realize How Differently I Was Taught to Think About Money
Good or bad…I was raised differently. Not better. Not worse. Just… different. My dad followed what people now call the Rich Dad Poor Dad playbook—before it was something people talked about online. And I didn’t realize how unusual that was until much later. Because to me, it was normal. It was normal to hear conversations about deals at the dinner table. Normal to hear about land contracts, trades, timing, negotiations. Normal to watch someone move forward on something… witho

Jaime White
4 days ago3 min read


I THINK IN DECADES
Family enterprise does too. Maybe that’s why I’m so interested in what comes next. Someone recently thought I was their VA. I corrected that pretty quickly. Ha. There are probably several layers to unpack in that interaction, including some old ideas about women, leadership and who is assumed to be doing what work. But mostly it made me laugh because I realized something: I think in decades. I always have. I don’t necessarily care what we’re doing Tuesday at 2:00. I want to k

Jaime White
Oct 234 min read


When Family Business Becomes Personal
What Washington needs to understand about families, employees and generational businesses Two years ago, I went to Washington DC and didn’t say very much. I listened. I watched. I tried to understand how all of this worked. I’m not a policy expert. I didn’t grow up dreaming about legislation. I grew up in family business. And I’m starting to realize that might be exactly why my voice belongs in the room. This week I was back in Washington DC with Family Enterprise USA, and I

Jaime White
Oct 84 min read


Before We Bring the Kids to the Table
My dad once told me I needed management training. He meant something like a one-day seminar. Maybe $500. I took that idea a little further. I started with management books. Then leadership books. Classes. Programs. Mentors. Coaches. More books. Lots more books. Eventually, my management training had very little to do with management. I invested in personal coaching. My marriage. Communication. Relationships. Then healing work. Fear work. Spiritual work. Intuitive work. Unders

Jaime White
Sep 254 min read


What If the Advice Was Never Meant for You?
When I first heard about Human Design, I said no thanks. I had already done DISC, Myers-Briggs, StrengthsFinder, Flag Page and plenty of other assessments. I love this kind of stuff. I love patterns. I love understanding people. But those were assessments. I answered questions about myself. Human Design wanted my birth information. That sounded a little too much like astrology for me. And I didn’t even get to take the assessment myself? No thanks. A couple months later, a wom

Jaime White
Sep 106 min read


What If Keeping the Family Together Isn’t the Goal?
I’m not entirely sure I’m ready for this idea myself. I spent most of my life in a family business. Well into my 40s. For a long time, I thought getting more of the family involved was the goal. Of course we wanted our kids to have access to opportunities. We wanted them to understand business, investing and entrepreneurship. We imagined them proposing new businesses, asking for investments and creating things of their own. That was just part of our family culture. Some famil

Jaime White
Aug 245 min read


Where There Was Once Shame, There Is Now Laughter
The other day I caught myself laughing. Not just smiling. Laughing. At something that seven years ago would have turned into an argument. I stopped for a second. I looked at Kevin. And I thought…We’ve changed. Not because life got easier. Because we did. I don’t know that I could have imagined this version of us. Kevin and I joke that we divorced the first version of our marriage. Not each other. The first version of us. The people who were trying really hard. Trying to be go

Jaime White
Aug 122 min read


Why Believe Crew Exists: Protecting Clarity, Alignment, and Trust When Decisions Shape Legacies
As businesses grow, decisions stop being simple. They stop being isolated. They stop being reversible. They stop affecting only one person. At a certain level, decisions begin to shape families, partnerships, teams, capital, and legacy itself. And yet—this is often the moment when leaders have the least space to think clearly. The Real Risk at Higher Levels of Leadership In early stages, the biggest risks are operational: cash flow execution traction speed But as organization

Jaime White
Jul 313 min read


The Calling Compass
When we work with business owners, we are often getting clarity on their unique calling. If we removed income from the equation… If time and money were handled… Who would we serve? Not what would we build. Not what would we monetize. Who would I contribute to? Who are you drawn to? What problems are you willing to live near? Where do you actually belong? Calling isn’t found through brainstorming everything. It’s revealed by noticing what keeps returning. Let's call it - The

Jaime White
Jul 104 min read


The Power of Being Delusional
One of the things I love most is that the work I do today is the same work I’ve always loved. The title changes. The company changes. The industry changes. But the work stays the same. I love sitting with visionaries. The people who see something that doesn’t exist yet. The people who say things like: • “What if we built this?” • “What if this industry worked differently?” • “What if we could solve this?” • “What if we’re thinking too small?” In other words, people who are j

Jaime White
Jun 253 min read


They Don’t Want Your Plan. They Want Their Place.
There’s a question I hear a lot: “What does the NextGen want?” And usually, it’s asked with good intent. But often…it’s asked too late. Or asked in a way that doesn’t actually work. Because here’s what I’ve seen: Most NextGen leaders aren’t resisting responsibility. They’re resisting misalignment. They don’t want pressure without context.They don’t want a role without clarity. They don’t want ownership without identity. And they definitely don’t want a plan that was created w

Jaime White
Jun 133 min read


They Were Never Trying to Retire
There’s something I’ve noticed after years of talking with financial advisors. And even more recently, leaning into those conversations more intentionally. The entire system is built around a single idea: Retirement. Work hard. Build wealth. Preserve it. Step away. And on paper, it makes sense. But when you sit across from founders…entrepreneurs…people who have built something from nothing…It doesn’t quite land. Because most of them aren’t trying to retire. They’re trying to

Jaime White
Jun 52 min read


The Gifts Didn’t Disappear. They Went Underground.
There’s a question we’ve started asking more often. Not out loud. But underneath everything we see. Which comes first? The disconnection…or the suppression of our gifts? Because after watching this in our own lives—and in the lives of so many others— it’s hard to separate the two. We tend to talk about addiction, distraction, and disconnections the problem. But what if they’re not the starting point? What if they’re the response? A response to something deeper. Because when y

Jaime White
May 213 min read


When You’re Asked to Hide What’s Actually True
A few years ago, we were part of a home church group. We hosted. We showed up. We wanted alignment. Not surface-level agreement—real alignment. So we did what felt right. We sat down with the minister and shared where we were. What we were learning. What we were experiencing. Especially around healing. And his response stayed with me. He said: If you talk about physical healing, people will line up. Stadiums would fill. Coliseums. And he asked us not to go there. I remember s

Jaime White
May 144 min read
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