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What I Learned Going From Solopreneur To A Business Of Many

For National Small Business Week, we’ve gathered valuable tips and resources to serve as your guide to all things entrepreneurship.Follow along all week for features that’ll help you navigate the small business landscape on your own terms.

For 15 years I’ve had the great privilege of helping people level up their finances. I’ve published three money books, hosted multiple makeover shows, and given over 100 talks. My podcast, So Money, features intimate financial conversations with celebrities, athletes and academics, and is nearing 10 million downloads.

And I’ve done this mostly as a business of one.

Admittedly, the solopreneur life is a good one. It provides me with professional autonomy, a seconds-long commute to the office (a.k.a. the desk in my bedroom), and flexibility to take a barre class mid-day.

But with this being my final year as a 30-something, I’ve been thinking more deeply about the level of impact and legacy I want to create and where I want to as  my mother says “go from here.”

And that’s led me to want to shake things up.

I’ve recently teamed up with two women, Patience Ramsey and Kindra Meyer, to co-found a company called She Stacks. Together we aim to financially empower women with an ecosystem of content, experiences and products that are simple, sexy, and social.

Our first offering is a massive, visual pop-up that celebrates financial feminism called Stacks House. (Think Museum of Ice Cream meets money for women.) It’s currently stationed in Los Angeles through May 19 with plans to tour the country.

To date, the transition has been gratifying, but also riddled with uncertainty. I’m learning a lot—about weighing risks, raising capital, and stemming your losses.

If you’re considering a similar move, here are my best pieces of advice.

A healthy risk is one that you can afford

Business is risky. But it’s not the probability of failure that matters. It’s the chances of your business being able to recover or pivot in the event of a failure that makes all the difference. For me, leaving my comfort zone of running a solo operation to start a company with two other people is risky. Investing my personal money into a venture that may or may not thrive is risky.

But it’s a risk that I can afford. And only today. A decade ago? Not so much.

Years ago I would not have had as much of a professional foundation to fall back on if things turned south with a growth venture. Today, I have my personal brand, credibility, and relationships to leverage in case our plans go awry. I also have more savings in the bank to shield me against losses.

Raise money carefully

As a solopreneur, I never needed to do a capital raise. I earned money, spent some, saved a lot, and invested the rest. On repeat.

But as I’ve scaled, smart friends have asked if the company is taking on venture dollars. The answer is no, but maybe later. She Stacks is primarily self-funded between myself and my co-founders. We have poured in some of our savings and taken on a few loans. That was a conscious decision so that we could maintain control of our beginning stages. While millions in venture capital can be enormously helpful to some start-ups, we think that it would be too much too soon for us. Call you in a year, though? And in the meantime, we have female-led companies that have paved the way and raised record amounts of venture capital and grown beautifully like Minted and Rent the Runway to inspire us when we’re ready to make that move.

Cut losses quickly

When things aren’t working out with a vendor, client or team member, it’s important to address the issues directly and immediately. And if it means letting this relationship go, so be it. In the long run, cutting ties with a party that isn’t adding value to your company’s mission, is the best route to take, as difficult as it may be at the time.  I’m learning that when you’re in the early stages of growing a business, you cannot afford the added stress of trying to work through an impossible relationship. Firing is just as important as hiring.

Pay attention to those who go the extra mile

The truth is, you’ll never be 100 percent sure if a person is the right hire, but doing your due diligence is still important. Someone who comes highly referred, who has experience producing results for the exact problem you’re trying to solve, and who comes to the interview having done his or her homework is incredibly important. Bonus: This person also appears genuinely passionate about what you are creating and seems willing to go the extra mile because they believe in the company’s mission. We turned down a potential hire because it was evident in the interview that this person hadn’t taken time to review our materials. This person was super skilled, but that was just a huge turnoff.

Find a balance with your co-founders

Not working with power-hungry co-founders is one way to strike a balance of power. We’re a lucky trio in that nobody believes she is more talented or more capable than anyone else in the group. We all work in service of our company and mission. When you take yourself and your own ego out of the equation, it’s much easier to find the paths that will move your business forward. What we do believe is that we all share responsibility in the successes and failures. We practice open and honest communication regularly. Our group text chain is epic.

Define your roles from the beginning

Our individual areas of expertise often define where we assume leadership. Patience is a brand marketing and operations whiz who keeps us buttoned up and moving forward with precision. Kindra is our creative genius driving the company’s brand identity and bringing ideas to life. And my focus is creating rich content and sharing our message with the media. That said, as a start-up, it’s all hands-on-deck sometimes and we’ve each had to jump in to support aspects of the business that weren’t exactly our sweet spots. But you roll up your sleeves and try your best to learn from your mistake!

Set communication expectations that everyone agrees to

My co-founders and I are all great friends by now. It’s not possible to keep strict boundaries when you’re in communication 24/7, is there? We try to build in some social time with founder dinners and outings. We try to meet in person as much as possible because we actually get a lot more done when we are together. To be totally honest, starting a company with three people, it’s an emotional process and we allow ourselves space and permission to share what we’re going through and our frustrations. No sense in keeping things bottled up!


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