From serious money mistakes to making serious money
You may think that my economics degree from Smith College made me financially savvy.
And that managing billions — with a capital B — of other people’s investment dollars during my twenty-one years with Goldman Sachs and the Bank of Israel would have taught me how to invest and manage my own money.
Or that my ambition and outgoing personality would make it natural for me to grow a successful business.
But you’d be wrong.
In 2002, my husband was diagnosed with cancer.
At the time, I had six children, the youngest only seven months old. Fear set in as I scrambled to manage our household while caring for my husband and our young family.
Determined to make it through, I took a long, hard look at our finances.
Shockingly, I discovered that despite all my experience and intelligence, our personal finances were in complete disarray.
The Goldman Sachs pension I expected to be healthy was stagnant; it had barely grown since I’d left the company.
Money invested via a money manager was significantly less than expected. Our nest egg was more of a nest amoeba.
A “hot tip” I had followed ended up depleting two-thirds of our investment capital.
My self-worth took a huge hit.
How could I, the professional who had successfully managed billions for other people, effectively flush away my family’s financial security?
There had to be something else going on here. I needed to go deep inside to find the fault lines. I discovered that at a cellular level, I was being guided by fear:
Fear of loss… and then feeling even smaller
Fear of being seen… and exposed as a fraud
Fear of being too successful… and thought of as greedy or selfish
Fear of not being enough… and failing abysmally
Those fears had led me to hold tight to what I had, play small, and, unbelievably, to avoid using my own G-d-given intelligence to manage my own money.
It was a lot to process.
That’s when I had my first big AHA.
If I could mess up that badly, how were other women without my expertise supposed to successfully manage their money and create lives they love?
Women all over the world have absorbed the same fears (regardless of their family history). Many women say that they “just don’t have a head” for numbers, or investments, or technology. But I definitely did not have those excuses.
Then, it hit me. My second AHA.
If anyone could do something about it, it was me. Debbie Sassen.
I could help women develop a healthier relationship with money.
Not only could I do it, but I needed to help women get paid in alignment with the value they're putting into the world, live free of money worries and full of possibility.
First, I’d need to heal myself.
I became a woman charged.
I embarked on my own coaching journey and did the work on the fears underneath: thought work, nervous system healing, tapping. Whatever it took to clear the money blocks I'd been carrying. And to stop needing more of it to feel like I was enough.
Along the way, I became certified in several modalities. Everything I was learning, I wanted other women to have access to as well. These skills later evolved into Worthy Money™; a money membership that empowers women to manage and grow their money with confidence.
I also invested deeply in learning what it really takes to scale: sales, leadership, decision-making, and the ability to step out of the day-to-day and think like a CEO. Soon, I found myself advising entrepreneurs in my network.
And then things started moving forward. Quickly.
The same year I started healing my relationship with money, my revenue broke through years of stagnation. It has grown every year since, and doubled in some of them. I've built a seven-figure business and an eight-figure wealth portfolio.
I'm not the only woman who's ready for more.
The women I work with aren't beginners looking for hand-holding.
They're already high achievers — talented, respected, and smart.
Part of why they chose to go out on their own was so they could design their own schedule. Take a friend out for lunch. Chaperone a daughter's school trip. Spend summer vacation actually vacationing.
And they do see success. People want what they offer and pay for it.
But somewhere along the way, they hit a breaking point: there’s no more of them to go around. They work too hard. Sacrifice too much. Ironically, the business they built to create freedom becomes a gilded cage.
Technically, many are ready to scale.
But ready and able are two very different things.
Scaling means writing the biggest checks they’ve ever written. Hiring talented people who need to be paid, come what may. Holding the energy and leading even when you’re not in the mood.
Getting a business from Point B to Point C is not a repeat of the first leg of the journey. And it needs a different type of support — more than a cheerleader husband or loyal friend. Support to take risks. To take on debt to grow. To turn down an opportunity and work on a better one.
I stepped into that role, working one-on-one with women who know they're meant for more. Finding the one thing actually stopping them from scaling, and removing it.
And that's when I had my third AHA.
I noticed that my clients didn’t have many friends who understood the challenges of scaling a business. Their families couldn't relate to the weight of major financial decisions. After all, few women have a social circle of business owners. Without realizing it, they were shrinking their CEO-selves to blend in.
It's hard to grow in isolation.
That's when I created Wired for Wealth — a high-level coaching program with a community element. It’s a place where ambitious women entrepreneurs grow alongside people who actually get it.
What’s happened inside this space has been incredible to see. When women have like-minded peers, momentum builds more easily. Confidence clicks into place. Growth stops feeling like pushing a boulder up a mountain.
Here’s what women inside our community say:
I was doing 95% of the work and still making a lot less than I could be. Deep down, I knew it didn’t make sense, but I felt too overwhelmed to change it. Debbie helped me see what was actually possible and work through the fears that were keeping me stuck.
Once I did the work, everything shifted. I’m now doing the exact same work, but at triple the income.
Rivky Rosenberg,
CEO, Flooid Design
I was selling my key package for $1,350, and I was feeling drained. At that rate, any challenge that came up with a client would create resentment. It felt like I was over-giving and under-earning.
Now that I’m offering the same package at $1,950, everything has shifted. I’m attracting clients who see the value and recognize it as a strong deal.
Zineb Layachi,
CEO, Raise the Runway
I could have stayed a coach working in someone else’s practice and done a great job there.
But Debbie taught me to separate the identity of working in my business from working on my business. I feel more in control, more empowered, and more confident stepping into both roles. What I’ve learned is that if you come in with a learning mindset, you can become a CEO; you don’t need to already have a “CEO personality” to get there.
alana stern,
adhd coach
I see each woman as a world.
When we change her life, we change the world.
Can we change your world?