This is the story of one of my friends, Steven, and how he helped me understand the link between Shame and Money.

On Sunday, at 10:12 pm my tablet pings. Someone has sent me a private message on Facebook. It’s from a person I don’t know. I click on it. Lindsey has contacted me about my book, Shame Hack. I’m flattered. My book has only been out for a week. She wants to know the relationship between shame and manifesting abundance. I do my best to answer her questions.

Shame and Money

I’d been entertaining the idea of writing a Shame Hack and money book, since there’s so much shame associated with money. Lindsey’s message nudged to me to explore the idea more.

I want to speak with self-made millionaires and hear what they have to say about money and financial success. By self-made, I mean that they built their own fortunes. They didn’t inherit them.

The following is my first exploratory interview with Steven, a self-made millionaire.

Steven’s Financial Success Story

I meet Steven at his firm on Monday afternoon. I feel a bit uncertain. I’ve never interviewed anyone before. Growing up money wasn’t something we talked about. Now I’m going to ask a stranger about money. Luckily, Steven is a friend of a friend.

Steven is in his early fifties. He’s taken care of himself and it shows. His frame is fit and athletic, a runner’s build. He still has a full head of hair, salt and pepper, about 80% pepper 20% salt. No glasses, clean pressed shirt with slacks, he’s the picture of casual sophisticated. We meet in the conference room.

Steven was an Asian kid who grew up in a beach town in Orange County, California. Growing up, there were very few other Asian families around. Both his parents worked. His father was a former science professor turned stock broker. His mother was a pioneering computer programmer. Steven’s work ethic was instilled in him from an early age. He grew up watching both his parents work. Both of Steven’s grandfathers were businessmen as well. The entrepreneurial spirit is in his blood.

As Steven and I talked about his background, something he said caught my ear. He talked about growing up playing games with the family, like mahjong and poker. He shared how playing games like this exposed him to learning about odds and risk when making financial decisions from an early age.

Our conversation transitioned to financial literacy. Tongue in cheek, Steven talked about the three states of money: not having enough, having too much, and having just the right amount. He joked that two of the three are bad.

Steven explains that the basics of financial success are straight forward. “First, you must earn money. You need to have some cash flow, such as a job. Second, you must save your money. Third, you must invest your money. But it seems money has a mystical element to it. Why is that? Why is investing hard? That’s because no one is talking about it.

“Your parents may have told you to get a job and save your money. But they might not have told you how to invest. If money was demystified when you were young, it would feel natural to save and invest. Investing is not hard to understand, but it’s difficult to execute because of emotions,” Steven explains.

Sometimes Steven gets frustrated when clients, (and many people, myself included) chase performance. He believes that is not the best strategy, as a matter of fact, exactly wrong. That philosophy is to only invest in things that are successful now. The hope is that those things become more expensive. It’s important to understand that investments are cyclical. Everyone knows the common wisdom, buy low and sell high. But when people chase performance, they buy high and hope it goes higher.

The historical data supports that when the stock market drops, it will rebound. But after the stock market drops, people get emotional. They sell off, and don’t make contributions. This course of action makes it very difficult to make gains with your investments.

If you were trained from an early age to invest, for example say $100. Then you could do it with $1,000, then $10,000 and so on. But when you’re forty with money to invest for the first time, you invest $100,000 and the market drops and you lose $50,000 in value. You think about how hard you worked and how much you lost. Then you make the wrong decision. Steven uses a metaphor to make a point, “Say you were raised Democrat or Republican or any indoctrination for that matter. When your party takes a hit do you change parties? Do hits make you change parties? Not likely. Same goes for investing philosophy.

“When the stock market is up people start to pay attention. They lift their heads up and want a piece. But the reality is, when the stock market is down your odds of success go up because the market has to come back to its average, as it has for the last hundreds of years.”

When the market is up, work more and save your money. Buy when the market is down. It sounds simple enough, but like Steven says, it’s difficult to execute.

I ask Steven why he keeps working. He has plenty of money. He starts his answer from a pragmatic place. He doesn’t want to run out of money. Life can change in an instant. More importantly, he still enjoys his work. He still wants to help people. And more interestingly, his passion and his purpose for his firm has evolved.

When Steven first launched his firm, it was his vision and he ran it that way. The firm grew and did well. The firm was eventually bought by a large financial institution. Steven cashed out. After some time away, he decided to return to the firm and bought it back.

But this time, he wanted to grow the firm not from his vision, but a shared vision. His current employees and team members contribute to the vision and direction of the firm. This change came from an insight Steven had. Before, he hired people based on their job skills, and how they fit into his vision. This put the employees and Steven at cross purposes. The employees were more inclined to want to develop themselves and their ideas. When the firm shifted to a shared vision, it aligned to a shared purpose. The employees and Steven developed themselves and the firm together.

The culture of the firm moved from I towards we. More of a tribal idea. Steven encourages his team to form relationships with each other, meaning getting to know one another and making some emotional investments in one another. He wants his team to get to a place where it is second nature to ask for and receive help. Steven aspires to move towards team accountability. There’s wisdom in this idea. When a client becomes dissatisfied with anyone, or part of the firm’s performance, the client’s recourse is to fire the firm. The whole firm is held accountable. Everyone wins or everyone loses.

I ask Steven what has changed since he’s made his money. Do people treat him differently? Interestingly, he tells me that now people may question his motivations. They wonder if his motivations are different or easier than theirs. He’s not part of the group. Also, depending on how a person thinks he’s made his money changes the attitude they might present. For example, if a person thinks he didn’t work hard for his money, or he got lucky, they may resent him for his success. If they respect how he made his money, or believe he deserved it, then there’s no animosity.

To wrap up the interview I ask Steven what he would want his two college aged kids to know about money. I thought I had already gotten the answer with the financial literacy idea. But I get surprised.

He says that if you love what you do, the money will come. You’ll be fine. I’ve heard this phrase before. I have to drill down on it.

I ask him, “Steven, when did you understand that?” He answers, “When I launched the firm. I was ignorant of the pain I would go through, but I was cognizant that’s what I wanted to do. So I was willing to continue on. I went into debt. This is my mom’s funny story. I was about to get married.

“My mom said, ‘Did you tell your fiancé you are $200,000 in debt?’

“No, should I?

“My mom lays down the law. ‘Here’s how it going to go down. The day you get married if you don’t take a paycheck from your firm, you’re done. You’re going to go get a job. You’re going to take care of your wife. Pay off your debt. And that’s how it’s going to be. That’s the way it works.’


“Our wedding day arrives. We are at the church. (My mom, by the way, is taking care of the book keeping.) My mom opens up her purse and says, ‘Hey guess what? You made it. Here’s your first pay check. It’s $500.’ Then hands me a check. ‘Oh, by the way, you owe me and your dad $500 for the money you borrowed.’ And took the check right back.”

I can see that Steven lives his financial philosophy. He earned, saved and invested. Following his philosophy, along with doing what he loves combines to create a powerful financial success story.

Your Truth

If you would like to know more about how get to your truth and know in your body that you are acceptable. Let’s talk. Book your free call now. Click the link below to schedule your call. It will be the best hour you spend freeing yourself from shame.

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Shame is NOT a life sentence, so free yourself.