his week, I read a sobering statistic that’s been living in my head rent-free:
70% of wealthy families lose their wealth by the second generation, and 90% lose it by the third.
Conventional wisdom says it’s because the next generations become lazy or entitled.
But that attitude says more about our collective loathing of the wealthy than it does about the individuals themselves.
In my experience, it’s rarely the case. Most of the next-generation inheritors I meet are eager to step out from the shadow of their parents and prove their worth.
And therein lies the real culprit behind the staggering statistic.
After working with hundreds of entrepreneurs, athletes, artists, and inheritors, I’ve discovered something deeper at play.
If you’re anything like me, you’ve wondered at some point if you deserve your success.
After I sold my company, this question haunted me more than I’d like to admit.
This wasn’t necessarily a conscious thought, but below the surface, embedded in the subconscious, I had this nagging feeling that I needed to prove I was worthy of the wealth I’d created. After all, why me? With so much suffering all around us, why did the universe allow me to have so much?
It was precisely this deeply embedded insecurity that drove me to rapidly deploy capital into deal after deal – startups, real estate, crypto, you name it. I was like a gambler at the roulette table, spreading chips across the board, hoping to prove my first win wasn’t just luck.
Of course, my behavior was shrouded in noble intentions. I told people that I was doing my best to help others create the same success that I had.
The painful irony? I lost millions trying to prove I deserved the millions I’d already earned.
This pattern isn’t unique to me.
We aren’t wired for wealth. Our brains evolved to keep us safe in an environment of scarcity. When abundance shows up – especially if we didn’t “earn it” through decades of blood, sweat and tears – our subconscious often works overtime to return us to what feels safe and familiar.
I see this play out all too often with the high performers I work with.
One client inherited a substantial sum from her grandfather’s business – a household name brand. Unlike the stereotypical trust fund kid, she works 80-hour weeks growing her own company. But no matter how successful she becomes, she feels like an imposter.
“I can’t shake the feeling that I didn’t earn any of this,” she told me during one of our sessions. “Sometimes I feel like I need to lose it all just to prove I can make it on my own. Am I crazy?”
I don’t believe she is.
The truth is, this worthiness wound runs deep in our collective psyche. Society tells us money must be “earned” to be deserved. This creates an impossible psychological burden, especially for those who make or receive wealth quickly.
If we feel unworthy of wealth, the reality is that it will start to disappear as quickly as it came.
We may try to prove our worth through increasingly risky ventures and overcompensation (leading to self-sabotage like my post-exit gambling spree).
Others (like my client) try to hide their wealth, always careful to never appear showy or ostentatious. This creates a shame-based prison of never feeling like enough.
Most families would rather talk about anything other than money. This silence creates a vacuum where unhealthy patterns thrive. When we don’t talk about money, we can’t examine the stories driving our decisions.
The families that successfully preserve wealth across generations aren’t necessarily the ones with the best financial advisors. They’re the ones who’ve done the inner work to create healthy money stories that can be passed down alongside the wealth itself.
Here’s what I’ve learned the hard way: You don’t have to earn the right to be wealthy. You don’t have to prove anything to anyone. The wealth you’ve created or inherited isn’t a burden to be justified – it’s a tool to be wielded in service of the life you want to create.
If this resonates, take a moment to reflect:
Where are you trying to prove your worthiness?
What would change if you believed you deserved your success?
For me, accepting that I was worthy of wealth – not because I earned it, but simply because I am – was the first step toward true freedom. Maybe it could be yours too.
To owning your worth,
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