As the co-founder and COO of Penny, I try to help people improve their financial literacy, get better at money, and build wealth through the help of short-form audio tracks. But this time last year, I would never have anticipated that I would be successfully launching a business in the midst of a global pandemic.
Throughout my career, as I've worked at the intersection of investment banking and technology, I have been acutely aware of various alarming statistics, like that 78% of Americans live from paycheck to paycheck, and only 39% are able to pay for a $1,000 emergency. With these figures in mind, my co-founder and I saw launching Penny as a chance to make a difference.
The experience of launching a company in 2020 had its own unique set of challenges. But we knew that it was the right time to take the leap with this idea, in part because of what the pandemic had brought to the surface for so many: deeply rooted issues like systemic income inequality, job insecurity, and the ballooning costs of housing, health care, and education, all of which has made it increasingly difficult for ordinary people to achieve financial security.
Here are some of the most important lessons I learned.
I began my career at an investment bank, advising my clients on multimillion-dollar investment opportunities. At the time, I was deep in student debt and unable to invest my own money while I focused on paying off my loans. The irony was not lost on me.
I was also working 80-hour weeks, which limited my ability to generate additional streams of income. But I tried my best. I worked as event staff at conferences, handing out brochures or manning booths for brands. I used my weekends to freelance my financial forecasting and pitch deck skills. And I drove for Uber on nights when I left work at a reasonable hour.
While I built those side hustles, I also had to take a look at my broader financial picture. It took some trial and error, but learning about credit and investing and how to build a budget helped me create a plan to work toward my money goals.
I lived off a bare-bones budget in the beginning, carefully monitoring what money was coming in and going out. When I hit certain milestones, I slowly reintroduced expenses, like reactivating a streaming service. Ultimately I was able to pay off my student debt within five years — which gave me the freedom to invest in myself and build more wealth.
I wasn't thrilled with the reality of participating in a financial system that benefited those who were already wealthy while I and so many of my peers were struggling. That dissatisfaction laid the groundwork for Penny's mission.
What I'd realized were my limits also informed our decision to focus on short-form audio in the app. I understood firsthand how valuable time is, especially when you're working to stay afloat financially.
After two and half years at the investment bank, in 2016, I left to join a tech start-up, where I worked for nearly four years. While I was at the tech company, in 2018, I created a luxury accessories brand that I still run today.
Around this time, my co-founder and I started talking about and working on Penny. In late 2019, we decided to go for it. At that point, we began hiring a small team. But when the pandemic hit, we had to briefly furlough our employees because our infrastructure wasn't developed enough yet to have a solid footing for remote work.
It definitely wasn't in our initial plan to have to pause our operations. But during the furlough, we we were able to build up all the processes we needed to have everyone successfully work from home. And in September, I made the move from Denver to Los Angeles, where our headquarters are based, to continue to grow our team.
As COO, I had three main goals: motivate and support my team, cultivate better practices for acquiring and producing third-party content safely, and launch our app on time.
What I found was that communication was often happening in silos and many employees felt walled up and unconnected to each other. I started setting up weekly one-on-one meetings with every person on the team to get a feel for how each employee felt and their current challenges.
Video by Courtney Stith
I set up recurring all-hands meetings, team check-ins, and a virtual product demo/happy hour on Fridays. We also improved our software to enable better collaboration and real-time discussion, which helped everyone feel more connected.
Ultimately, my biggest challenge — to develop a rapport among a completely remote team who didn't know each other, or me, very well — was a great opportunity to build a company culture where everyone's voice could be heard.
When we started Penny, we thought we had more time when it came to building and launching our app. But as people experienced job losses and struggled to make ends meet due to the pandemic, getting it out in the world quickly became our top priority.
Like many companies, we had to rethink our approach to business, and how to meet our goals, with health and safety protocols in mind.
Video by Mariam Abdallah
Our team was able to come up with creative solutions to overcome potential obstacles, like developing a system to record all our content remotely, even sending equipment to people's homes. Thanks to everyone's quick thinking and collaboration, two months after I moved to Los Angeles, our app was officially launched.
This experience has shown me that people are motivated by causes they find meaningful. Everyone we've hired has personally experienced some aspect of the problems we are trying to solve.
If you are starting a business, especially right now, my best advice is to collaborate with people who share your vision.
And if the last year has taught me anything, it is that we are all capable of more, and more adaptable than we realize. Change is scary, but opportunity exists even in the most challenging circumstances.
Charlotte DeMocker is co-founder and chief operating officer at Penny, an innovative digital media start-up that successfully launched during the pandemic. Penny seeks to help ordinary people master their money. Follow Charlotte on Instagram @charlottedemocker and learn more @penny.app.
More from Grow: