Bobbi Rebell's money moguls' 'Financial Grownup' moments

30 financial powerhouses reveal how they got their money mojo in new book

Q&A: Bobbi Rebell, author, 
‘How To Be A Financial Grownup’
Q&A: Bobbi Rebell, author, 
‘How To Be A Financial Grownup ’

Can’t imagine Ivanka Trump flying coach? Or Jim Cramer from “Mad Money” living out of his car? Or a strapped Drew Barrymore turning down millions after her star-making turn in “E.T.”?

These are just three of the anecdotes featured in “How to Be a Financial Grownup,” a compendium of personal aha! moments, compiled from 30 financial powerhouses by Thompson Reuters TV anchor and personal finance colmnist Bobbi Rebell.

Ever wonder how some of the shrewdest money managers on the planet got their mojo? Rebell found out by asking them two simple questions: What was your financial grownup moment and what lesson did you learn from it? She then tapped her own expertise and advice from others to translate these first-person experiences into actions we all can take to get a better grasp of our greenbacks.  

Q: What inspired you to collect these “grownup moments?”

A: Tony Robbins was in many ways the inspiration for me. In his book, “Unleash the Power Within,” he talks about being overweight in this 400-square-foot studio apartment, and he says, “You have to just decide.” So I decided I would write a book that collects these incredible personal stories about money.

I never prodded any of the role models; whatever I got, I got. I never said, “You know, I’m a little light on this chapter …” None of that. Everything was wide open and presented in their own words.

Author Sarah Newcomb

Author Bobbi Rebell, whose book "How To Be a Financial Grownup" was released Oct. 18, 2016

Q: How long did it take to collect these stories?

A: I’m really driven. I would say, start to finish with the anecdotes and writing, it was about six to nine months. It’s not like I sent out 30 invitations and 30 people said yes. There were some no’s, and  we’re hoping they’ll be yeses for the next book.

Q: In addition to such expected chapter topics as debt, investing and real estate, a few entries earned a chapter all their own.

A: A dear friend of mine, Aaron Shapiro, who’s the CEO of the digital marketing agency, came up with one of my favorite stories, because it talks about hiring friends and how tricky that is. A lot of people, when they start businesses when they’re young, the natural thing is, “Hey, roommate – you’re my No. 2!” right? But just because they were assigned to you at Harvard or wherever, that doesn’t mean it’s the best business decision. And Aaron talks about hiring his friends and having to make a business decision to fire them. I read that and said, “This is important. It has to be a chapter.”

Q: A few of these grownup moments are bittersweet. For example, Kevin O’Leary of “Shark Tank” wistfully gave up his dream of being a professional photographer to, in his words, “make money, and lots of it.”

A: Yeah, but here’s the thing: He didn’t. I’ve been to Kevin’s art shows and he’s amazing! He is doing photography; he’s just not as famous for it. He did not abandon it at all in the end. He has art shows and donates the money to charity.

Q: Considering that we’re just days away from electing our next president, readers will likely make a beeline to Ivanka Trump’s entry. How did that come about?

A: Before her father was running for president, Ivanka Trump was one of the first people to sign up for the book, and she was so enthusiastic and so lovely. People said, “Why would you include her? She was born rich.” But that doesn’t necessarily mean they don’t have a lot to share. Plenty of rich people mess it up. As Tony Robbins observed, we all have different starting lines. If your starting line is not as good as your friend’s, get over it; move on.

While Ivanka clearly had a head start over the vast majority of Americans, she took it upon herself to create her own identity and financial future by using the resources she had, which is fair. Life is not fair, but you should use what you have. She had a name and financial resources, and yet she created her own brand identity. I was really honored that she participated in the book.

Q: One irony that emerges in the book is that we often need money skills the most when we have the least. For instance, many will fumble their first credit card, as “Real Housewives of New York” star Heather Thompson did.

Plenty of rich people mess it up. As Tony Robbins observed, we all have different starting lines. If your starting line is not as good as your friend’s, get over it; move on.

A: Yes. In fact, I was initially concerned that I would get nothing but credit card horror stories and then what would I do, write a book about credit card debt? It was such a relief that no one else said that. Kids today are flooded with offers. Thankfully, now at least there are some parameters as to what the card companies can do on college campuses. It used to be that they could just give you a Frisbee for signing up, and now they can’t do that kind of stuff anymore. To get my 19-year-old stepdaughter a credit card, we had to put her on ours. You really do need a parent to supervise it, and I do think it’s an improvement for the industry.

Q: Another standout aha entry comes from Ellevate founder Sallie Krawcheck, who not only encountered her grownup moment as the result of her husband’s infidelity, but turned it into a global professional women’s network. Her cautionary tale was much more stick than carrot.

A: Yeah, and she was really blunt about it! She sent me that via email from an airplane in the middle of the night and I was like, does she know this is going in a book? I could not believe the candor. Especially for young women, it’s a real awakening that while we all have to trust our partners, you do have to at least be aware of what’s happening with your money, and she didn’t know. And this is Sallie Krawcheck! I think everything happens for a reason.

Q: Your own grownup moment came with that classic threshold-to-adulthood question: to rent or to buy? In your case, you wisely chose to buy your New York apartment. What makes this crossroads such a life-changer for most?

A: When I did the math, I realized that my out-of-pocket would be so much less by owning that even if I sold it for a loss, I would be OK. It was still a risk, and people do lose money on real estate. And there is a case to be made against owning, especially if you have a job where you’re going to be moving around. But you could also move out and rent the place.

Especially for young women, it’s a real awakening that while we all have to trust our partners, you do have to at least be aware of what’s happening with your money, and she didn’t know.

Q: You close out the book with a fascinating grownup moment from actress Drew Barrymore, who explains how she decided to stand her ground on the flood of film offers that followed her big screen debut in “E.T.”

A: What were the odds that Drew Barrymore would end up in my book? It resulted from a chance encounter on my day off from Reuters and went to an event where she was speaking. I had been looking for sources on retail, and she was up there speaking about these businesses she has in addition to her film studio, including this incredible beauty business which is the No. 1 beauty line at Walmart. Who knew? Afterward, I managed to get a couple minutes with her and she told me this story.

What I learned from her is nothing short of jaw-dropping. Yes, biologically, she had a grandfather, John Barrymore, who was a very famous actor, which is great. But her mother fell so far short as a mom to where Drew was emancipated at age 14 and was basically on her own, doing odd jobs to support herself. She was taking care of her mother. That’s where this drive and amazing talent came from.

Her moment was so organic that she ended up being in this book, because it really says it all: that it’s on you. I still don’t know how she found this drive.

Q: Will there be a sequel?

A: Absolutely, yes! And if your readers have ideas of what they want to hear more of, please get in touch with me through my website,

See related: 6 ways to overcome the shame of debt, Financial problems span generations, so is debt in your DNA?, For uncontrolled spenders, cash-only may be the right lifestyle

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Updated: 03-26-2019