How Transparency Got This Entrepreneur A $1M Check

How does a 29-year-old computer programmer who is earning multiple six figures end up broke? That’s the question Amanda Steinberg, now the founder of DailyWorth, asked herself back in 2008. “It wasn’t because I was spending money on clothes or shopping therapy,” says Steinberg. “It was because I didn’t understand the house that I was buying and I didn’t understand the taxes related to my business.”

Rather than hire a financial adviser, which would have been the logical thing to do, she started publishing about it on the internet. From her attic office in Philadelphia with a newborn in her arms, she launched DailyWorth — every women’s guide to money, career and business. Today, DailyWorth’s newsletter reaches more than one million subscribers. In 2015, she launched WorthFM, a digital investing service. Forbes named her one of the 21 New American Money Masters and Oprah selected her to the exclusive SuperSoul 100. And now she’s the author of Worth It: Your Life, Your Money, Your Terms.

The mentoring moment I want to share today had such an impact on me and really changed the course of my life. It happened in 2016. DailyWorth and WorthFM were still two separate companies — WorthFM is an investment advisory and DailyWorth is a media company. We’ve been venture capital-backed for the last six years. What happens when you’re venture capital-backed is that you have to grow really fast in order to justify the reasons why you took that capital. This can create a vicious cycle of needing more capital in order to thrive.

We had a lot of trouble raising capital in 2016 because the companies were separate and most investors wanted to invest in one entity, but the merger process of creating a holding company was going to take months. I was in a really difficult, depressed and scared place for our future.

My mentoring moment came from Jamie McIntyre, one of my board members and advisors. One morning before my meeting to pitch an investor, Jamie said, “Amanda, be honest about who you are and what you’re up to. Express the situation that you’re in. Use your passion and your power to say what’s really going on for you.”

When you’re an entrepreneur and you are constantly pitching venture capitalists and getting up on stages, you have to create a sense of credibility and composure in order to inspire people’s trust, so they will invest in you. So for me to be honest about where we were was downright frightening because I thought it was going to make me less desirable as a recipient of additional capital.

That morning I took Jamie’s advice, walked in to pitch an investor and walked out with a million dollar check. It was a real turning point for me: often we’re hiding behind who we think we’re supposed to be, but when you become who you really are and you really forge a connection with someone, that is where the magic happens. You have to know that your challenges, pains and fears don’t make you weak. You can be strong, optimistic and passionate in your delivery of both what your strengths are and what the opportunity is, as well as what your real challenges are.

I’ve found that this actually inspires more trust in you. It doesn’t make you look weak. They’re not mutually exclusive. You can be vulnerable. You can express challenges. You can be honest and you can be powerful at the same. The more honest I am the more magnetic I become because people are really attracted to authenticity. It’s a slightly overused word these days, but it’s for good reason.

To find out your money personality (are you a visionary, producer, nurturer, epicure, or independent?) and to hear the stories behind the quotes below, check out our podcast.

I chose marriage at a very young age because I got messages from everywhere that I would be unhappy if I didn’t.

“If I earn more money, I will have more money.” That can backfire in nasty ways.

Financial advice is bad at serving you. It’s not that you are bad with money.

I am done with following rules that someone else told me to follow.

Our culture has a deep attachment to work as identity—we have been socially conditioned to work.

By Denise Restauri

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