6 Leaders' Takes On Being Fearless In Money And Life

These movers and shakers took big risks to get where they are today. Here are some words of wisdom from their journeys.

David Daneshgar, co-founder of BloomNation

"When it comes down to it, and you have all your chips down, are you willing to trust yourself? Ninety-nine percent of people don’t because they are scared."

Ruth Zukerman, co-founder and creative director of Flywheel Sports

"After my divorce, I was determined to rebuild my life--and succeed financially on my own. I didn’t want to ever feel that I had to rely on anyone but myself."

Bruce Poon Tip, founder of G Adventures

"Being financially fearless is also about freedom and creating happiness through your triumphs in equal measure to your mistakes. Life would be boring if we always came out on top."

Angela Lee, founder of 37 Angels

"Test your assumptions. Before you quit the six-figure job or invest $50,000 into your startup, do a one-week or one-month test run. Think you found your dream job? See if you can shadow someone for a day who actually does it day in and day out."

Kate White, author of I Shouldn’t Be Telling You This: Success Secrets Every Gutsy Girl Should Know

“Start building your later-in-life nest egg NOW. When my dad told me that in my twenties, I thought he was nuts--but that strategy became my ticket to an exciting new life and career when I was ready to leave the magazine industry in my fifties.”

Mayer Dahan, C.E.O. of Dahan Properties

"I know to be successful at a young age is an incredible accomplishment, but to be charitable shows the amount of financial fearlessness you truly have. I’m always inspired by the quote: ‘We make a living by what we get, but we make a life by what we give.’"

6 Successful Leaders On What It Takes to Be Fearless

These movers and shakers took big risks to get where they are today. Here are some words of wisdom from their journeys.

What does it mean to be “financially fearless”?

LearnVest C.E.O. Alexa von Tobel defines it as taking control of your money, so it doesn’t control you. That’s one reason why she named her new book Financially Fearless—she wanted her advice to inspire people to go from feeling anxious about money to feeling amazing about it.

We were curious to know what types of answers we’d get from other business leaders if we asked them to define financial fearlessness in their own words. So we reached out to everyone from successful entrepreneurs to intrepid investors and found that their points of view didn’t just apply to their financial lives—they also seemed to reflect a mantra from these bold leaders’ personal lives.

David Daneshgar

1. Don’t let the unknown throw you off your game.

—David Daneshgar, cofounder of BloomNation

This former World Series of Poker champion left the world of high-stakes card games to become an entrepreneur, cofounding BloomNation after his friend complained that his aunt’s florist business was being hurt by competition from online floral websites.

So he and his partners got the idea to build an online marketplace that connected customers directly with florists, enabling them to get exactly what they wanted instead of relying on stock photos that didn’t always reflect what was delivered. But Daneshgar needed the funds to get started. His solution, naturally, was to win a game of poker. So he entered a local tournament and won more than $25,000 to launch the business. Despite the odds at stake, Daneshgar says that losing was never part of his fearless plan:

“Luckily, I didn’t have [the fear of losing], although my partners did. Poker makes you emotionally stable, no matter what the financial swing is. If I lost $50,000 one day, [I knew I’d] win it back another day. If I showed my emotions, I wouldn’t be able to win. When I knew money was on the line, I always did better.

When it comes down to it, and you have all your chips down, are you willing to trust yourself? Ninety-nine percent of people don’t because they are scared. Even when I was in business school, everyone claimed they had an idea, but they couldn’t execute on it [because of fear]. They were [leaving school with] $100,000 worth of debt, so they had to be financially comfortable. But an entrepreneur knows that anything that is comfortable is not in their ecosystem.”

Ruth Zukerman

2. Make sure your passions pay off.

—Ruth Zukerman, cofounder and creative director of Flywheel Sports

After years spent working as an indoor-cycling instructor, Zukerman decided to start a business with her partners that centered on what she knew best. So in 2010 she launched Flywheel to make group exercise a truly branded experience. They focused on perfecting every detail—from the equipment to the playlists—and subsequently went from a single location in New York City to 25 outposts across the U.S. (and seven abroad, including one in Dubai) in just a few years.

Her fearless key to success? Making sure that her zeal for group fitness could fulfill her personally—and financially.

“When I started my journey into the world of indoor cycling, my primary goal was to build a career that would bring me great fulfillment. However, carrying my heavy backpack from gym to gym wasn’t exactly lucrative. Yet that didn’t deter me from gaining more experience, and trusting that I would come up with a way to use my talent and passion to ultimately provide me with a more than comfortable lifestyle.

After my divorce, I was determined to rebuild my life—and succeed financially on my own. I didn’t want to ever feel that I had to rely on anyone but myself. My method of teaching brought about a huge following, which enabled me to take my career to the next level—providing a wonderful life and security for my future.”

Bruce Poon Tip

3. It’s okay to take a risk—it just might be worth it.

—Bruce Poon Tip, founder of G Adventures

Getting fired from his job at McDonald’s as a young man was the best thing that ever happened to Poon Tip because it made him realize that he’d only be happy if he worked for himself. So in 1990 he maxed out two credit cards (which, by the way, we wouldn’t recommend!) to start an adventure-travel company, G Adventures. In his case, the risk paid off—he now runs tours on seven continents for over 100,000 travelers a year.

Poon Tip’s unconventional ideas for how to run his company (there’s no CEO or human resources department, to name a couple) also spawned a New York Times bestseller, Looptail: How One Company Changed the World by Reinventing Business. For Poon Tip, risk-taking is not a scary proposition.

“A high tolerance for risk is really at the heart of every great entrepreneur who lives for those high-risk/high-reward opportunities, which don’t come around often. I get excited by [these kinds of] opportunities—I view them as keys to being innovative and disruptive in business, which creates differentiation for your company.

I was so passionate to start G Adventures that I had no choice but to be financially fearless and take a huge leap by maxing out two personal credit cards for seed money, when no financial institution would give me a loan or believe in me and what I wanted to do.

But being financially fearless is also about freedom and creating happiness through your triumphs in equal measure to your mistakes. Life would be boring if we always came out on top. One of the greatest aspects of being fearless is when we stumble or make mistakes because it’s how you get up that really matters.”

Angela Lee

4. Never make uninformed decisions.

—Angela Lee, founder of 37 Angels

When Lee, an adjunct assistant professor at Columbia Business School and a former marketer, launched her angel-investing network, only 13% of such investors were women. Lee wanted to boost that number to 50%—and thus found inspiration in the number 37, the percentage difference that women would have to make up to reach that goal.

37 Angels funds early-stage startups for both men and women, and Lee also trains other women on how to be smart angel investors. So it’s no surprise that Lee’s key to taking away the fear in making money-related decisions is due diligence.

“[When making career decisions], too many people ignore the realities and dive in blindly. Want to start a food blog? Take photos with whatever camera you already own before investing in that fancy DSLR. Need lighting equipment? See if you can borrow or rent it first.

And test your assumptions. Before you quit the six-figure job or invest $50,000 into your startup, do a one-week or one-month test run. Think you found your dream job? See if you can shadow someone for a day who actually does it day in and day out. I really thought I wanted to be a chef, and had applied to culinary school and everything. Rather than invest in those two years blindly, I worked part-time in a kitchen for six months, which made me realize what aspects of the food business I love versus what parts I had merely glamorized.”

RELATED: 10 Questions for a Career Coach

Kate White

5. Plan early so you can pursue your future with confidence.

—Kate White, former Cosmopolitan Editor

White ran the helm of Cosmopolitan magazine for 14 years as editor in chief—a job some women would kill for. But she knew that, at some point, she wanted to pursue her other dream: writing books. So she stepped away from her storied position to focus full time on her second act.

The result? Her Bailey Weggins mystery series and career advice books became bestsellers. But despite the fact that she took chances in her career, she didn’t want to take them with her financial security, so here’s what she had to say about being fearless about saving:

“Start building your later-in-life nest egg NOW. When my dad told me that in my twenties, I thought he was nuts—but that strategy became my ticket to an exciting new life and career when I was ready to leave the magazine industry in my fifties. Life goes by faster than you think!”

“I’m always inspired by the quote: ‘We make a living by what we get, but we make a life by what we give.’"

Mayer Dahan

6.Giving back should be part of your plan.

—Mayer Dahan, C.E.O. of Dahan Properties

Dahan’s world is split between helping society’s well-heeled and its most vulnerable. The real estate developer and entrepreneur builds high-end homes that are sustainable, ecofriendly, and earthquake-proof in Los Angeles’ tony neighborhoods. But he also grew up watching his immigrant parents struggle to make ends meet, which influenced his passion for volunteerism and charitable giving.

As a result, he started a philanthropic organization, The Dream Builders Project, to support causes ranging from affordable housing to human trafficking. For him, being charitable—with your dollars and your hours—shouldn’t be an afterthought. If you’re fearless about making money, you should be just as fearless about giving it away.

“I know to be successful at a young age is an incredible accomplishment, but to be charitable shows the amount of financial fearlessness you truly have. I’m always inspired by the quote: ‘We make a living by what we get, but we make a life by what we give.’"

I think too many professional people have a complex about saving for a rainy day. Although it’s important to be frugal and smart with money, it’s of equal importance to give back, and we all have a moral obligation to do so. The ability to give back on a large level highlights how financially fearless one truly is because that money is being invested in a cause, rather than the person who made it.”

Julia Chang is a Senior Editor at LearnVest. Previously, she worked for the custom content division of Time Inc., where she helped produce award-winning print and online content for financial consumers.

This article originally appeared in LearnVest and is reprinted with permission.

[Image: Flickr user Sascha Kohlmann]

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