4 Lessons From Seven-Figure Entrepreneurs Who’ve Been There

When we think about successful entrepreneurs or visionary leaders, our minds tend to drift to the highlight reel: the splashy press, the multi-million dollar funding rounds, the products we know and love.

As a therapist and executive coach, though, I often get a peek behind the scenes. I see the entrepreneurs working around the clock to grow a business, the founders facing down only weeks of financial runway, the leaders not sure that the world will ever get to see their vision.

So, if you’re facing a roadblock, a rough patch, or a failure, the first thing to do is to know you’re not alone. In fact, even the most “successful” among us (perhaps especially the most successful among us) deal with feelings of disappointment, discouragement, and failure, too.

What’s more, our toughest moments can also be incredible opportunities for growth — both personally and within our businesses. Below, I’m sharing some key lessons I’ve learned from other trailblazing business leaders who’ve experienced feelings of failure firsthand. My hope is that their experiences will normalize this part of your journey, as well as provide some actionable next steps for moving forward.

Lesson #1: Don’t Be Afraid to Pivot

In 2017, Victoria Repa had what she thought was a brilliant idea for her company, BetterMe (a health and wellness ecosystem with accessible digital health products, athleisure goods, and wearables): combining meditation with VR glasses. “I thought such a sensational technology would attract many users to meditative practices,” she says, so she invested $30,000 in creating and testing a prototype

It wasn’t the successful launch she was hoping for. “The process of meditation is a challenging one for many, and the additional equipment required to do so only made things more difficult,” she explains. As a result, only 0.5% of users made use of the feature.

It would have been easy to dwell on the defeat, but Repa decided to view the failure as an experience rather than a personal setback. “It was a pity that we lost time, resources, and money, but it was great that we gained experience and made proper conclusions,” she says. “Realizing that our test was negative and that there was no need to pursue or scale the feature… prevents me from incurring further losses in the future.”

After the failure, the team pivoted to testing other features to find new opportunities and potential for growth. “Obviously, some of them became a success, while others were left in an archive labeled ‘failed tests,’” she says. But she sees them all as part of the process: It’s now part of BetterMe’s philosophy to “cherish a positive error culture.”

Lession #2: Pause And Regroup

“Imagine what it’s like when you have no idea what to do to save your startup,” Meredith Noble, cofounder and CEO of Learn Grant Writing shares. That was the situation she found herself in two years ago: The business was losing $20,000 each month and had exhausted every marketing tactic possible trying to turn things around. “It wasn’t long before we had six-weeks of financial runway left, and the first time I thought, ‘Maybe I can’t do this,’” she says.

Rather than continue to chase even more quick fix marketing tactics, she and her co-founder decided to pause their efforts. Taking a step back gave them the fresh perspective to overhaul their offer and price point, focusing on a single offer, a single customer segment, and a single marketing channel. “It worked,” she says. (Her formula: Nail down the cost to acquire and serve that customer and multiply it by three to determine your product price.)

Recognizing that what they’d been doing previously wasn’t working meant putting their ego aside. But it also meant that, on the absolute cusp of failure, they turned the business around. Now, the company generates seven figures in revenue annually and has “the most remarkable community of customers we love,” Noble adds.

Lesson #3: Remember Your Why

“My cofounder and I were 18 months into building Motherly, and I felt like a professional failure,” says Elizabeth Tenety, co-founder of the digital platform for a new generation of mothers.

“I was working 24/7 to get Motherly off the ground, and while our audience was growing, we couldn’t yet raise venture capital to invest in our vision,” she says. In the meantime, she had turned down grad school at Harvard, her husband took a stable but stressful job to support their family, and she was paying childcare providers more than she was making herself. “I just increasingly felt like I could never get to the other side of the mountain,” she says.

There was a moment of serendipity in the slog. “A random tweet a friend tagged me in snowballed into a feature on Motherly in an industry trade publication, which led to inbound interest from a VC looking to invest in Millennial moms,” she says. To date, the brand has raised $5.8M and is growing year over year.

While the bit of luck certainly helped the business turn a corner, Tenety gives more credit to her faith in the vision: to build a supportive, evidence-based and non-judgmental platform for mothers. If she hadn’t brought the platform to life, it wouldn’t exist today, and keeping that “why” in mind led to its ultimate success.

Lesson #4: Develop A Growth Mindset

Tenety also recalls Motherly’s early days, when an advisor told her that she couldn’t fail. “What he meant was that the only failure would be not learning and growing in my skills, experience, network and mindset along the way,” she says.

Now, she knows that advice to be true. “Even when you have to start over—on a project, a launch, or even your entire venture—you’re not starting from scratch, you’re starting from wisdom and experience,” she adds. “Amidst the ultimate setbacks, there are massive opportunities for evolution, improvement and change.”