Charlotte Democker of Penny: “Trust your intuition ”

If you’re trying to do right, you’ll do it more often than not. Trust your intuition — whatever your gut is telling you, it’s probably correct. Bad news doesn’t get better with time. As a part of our series about business leaders who are shaking things up in their industry, I had the pleasure of interviewing Charlotte DeMocker, the co-founder […]

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If you’re trying to do right, you’ll do it more often than not.

Trust your intuition — whatever your gut is telling you, it’s probably correct.

Bad news doesn’t get better with time.

As a part of our series about business leaders who are shaking things up in their industry, I had the pleasure of interviewing Charlotte DeMocker, the co-founder and Chief Operating Officer at Penny, an exciting digital media startup that seeks to help people master their money. As an analyst at a top investment bank, Charlotte became concerned that the financial system catered only to the wealthy elite. She saw millions of bright young people struggling to get ahead because they lacked a basic understanding of finance, and so she embarked on a mission to correct this inequality by demystifying the topic of money.

Thank you so much for doing this with us! Before we dig in, our readers would like to get to know you a bit more. Can you tell us a bit about your “backstory”? What led you to this particular career path?

Thank you for having me! I pursued a degree in finance after being inspired by my father’s work in wealth management, and spent several years working at a boutique investment bank. My time there taught me a great deal, but it was very different from the work that inspired me — which was rooted in helping the average person invest in, and plan for, their future. Instead, the bank’s services were available only to the extraordinarily wealthy and provided access to investments that most individuals will never have. This gave them an unfair advantage in maintaining and building wealth, while millions of ordinary people struggled to even pay rent. That didn’t sit right with me, and over the years I felt a calling I felt to use my knowledge and skills to help others grow stronger.

Can you tell our readers what it is about the work you’re doing that’s disruptive?

Penny is the only audio-streaming app in the United States that is exclusively dedicated to helping people master their money. We are a mission-based company and we believe that if you work hard, you should be able to get ahead in life, but unfortunately that isn’t enough anymore. The statistics show that 78% of Americans live from paycheck to paycheck, and 53% of college graduates are either unemployed or under-employed — and that was before the global pandemic. The truth of the matter is that the education system is failing us, and does not provide even a basic level of financial literacy with which to navigate the world. Money is a scary and stressful subject for a lot of people, but especially for young people who are saddled with student debt and working multiple jobs just to stay afloat. Our goal is to provide the knowledge and tools to empower millions of people to free themselves from debt, open the door to passive income, invest in their future, and move up in the world.

Can you share a story about the funniest mistake you made when you were first starting? Can you tell us what lesson you learned from that?

When I first started out as an entrepreneur, an angel investor and I decided to acquire a men’s fashion company that had a solid base of customers as well as a strong following on social media. After acquisition, however, we discovered that we had been misled about the entire supply chain of the company and none of the unit economics or quality standards were legitimate. When we asked for an explanation from the person who had sold the company to us, he simply replied: “Sometimes you just have to lie [to consumers].” I was rendered speechless.

At the time I didn’t find it funny but in hindsight I do, because it highlights just how naive we all can be in the beginning. That experience has taught me that, in business, the rule of ‘caveat emptor’ always applies — and no matter what someone says, there is no substitute for good old due diligence. Luckily it did not impact my relationship with the angel investor.

We all need a little help along the journey. Who have been some of your mentors? Can you share a story about how they made an impact?

Mentors can be very powerful influences in professional development. I believe everyone should seek them out and try to find several, so you can benefit from a variety of different perspectives. My variety of mentors include my father, a favorite finance professor, a dear friend and high-profile lawyer, and my former boss.

My former boss, Josh, had a powerful influence on my professional development and my perception of good leadership. Through the investment banking and startup industries, I have experienced some extremely difficult managers in my lifetime. Sometimes the only lesson you wind up learning is what kind of boss you don’t want to be in the future. I’ve always felt that leaders should inspire, advocate, and lead by example, but had struggled to find one to learn from in real life.

When I met Josh, I was so inspired by his work that I essentially forced my way onto his team and the rest became history; we worked together for more than three years. I relished every day of it because I learned so much from him, both by observing and through active mentorship. He was the first person to manage me like a human — he invested in and advocated for my development, empowered and engaged my interests, and never micromanaged my output.

I learned so much from Josh, all while enjoying work that felt fun and exciting. Now that I am managing a large and diverse team, I reflect on all the ways his leadership helped me and try to emulate those approaches with my own team, where appropriate. I’m still growing into my leadership style, but I certainly wouldn’t have the headstart that I do without that experience. Over the years Josh became a friend and mentor, and he was particularly supportive when I first told him about the vision for Penny. His encouragement helped to convince me I was on the right path and the confidence to proceed forward into the unknown. These days we still talk regularly and he still gives the best advice.

In today’s parlance, being disruptive is usually a positive adjective. But is disrupting always good? When do we say the converse, that a system or structure has ‘withstood the test of time’? Can you articulate to our readers when disrupting an industry is positive, and when disrupting an industry is ‘not so positive’? Can you share some examples of what you mean?

I don’t believe that disruption is always good. Nothing is always good, or always bad — it depends on the outcomes at the end of the day. And while there are many different, contesting perspectives around whether an outcome is good or bad, ultimately, I believe that something is ‘good’ when it results in the greatest good to the greatest number (of people).

I don’t want to get overly geeky or technical here — but in economics, there is a phenomenon known as rent-seeking. A good way to understand rent-seeking is that it seeks to prevent people from having light bulbs in order to protect candle makers. Rent-seeking is the opposite of innovation. Whereas innovation seeks to produce new, efficient solutions to problems, rent-seeking seeks to maintain the status quo so that the entrenched incumbents can continue to reap the economic benefits without making improvements or adding value. We see many examples of this in our society today.

For example, electric vehicles have been a thing for over a decade — and yet, less than 5% of all vehicles in America are electric. Obviously, if more vehicles were electric, companies such as Exxon and Shell would be in serious trouble. They have a vested interest in maintaining the status quo, even though it is bad for the environment, and therefore, also bad for humanity in the long run. Disruption is capable of breaking the status quo quickly — even if special interests were to lobby for legislation in their favor, this places them on the back foot, reacting to the disruption rather than staying ahead of it.

I think we all know about how Uber and Lyft disrupted the transportation industry — and specifically, greatly reduced the influence of the highly exploitative taxi medallion system. In cities such as New York, a taxi medallion can cost up to $1 million, and this is a classic example of rent-seeking at work. Uber and Lyft, while far from perfect themselves, have forced the market to open up — this benefits a lot of people.

At the same time, however, every coin has two sides. When disruption happens, people often get displaced. In recent years, there have been tensions about fracking, or about bringing back manufacturing jobs that are getting eliminated due to outsourcing (and, more pertinently, to automation and technology). In fact, according to a study by McKinsey and Company, up to half of all jobs as we know them today will be eliminated by the year 2030. Can people reskill themselves quickly enough to pivot their careers wholesale, in the face of disruption? And should we, as a society, not do more to protect the people who can’t? It is a very difficult dilemma to be faced with, and when I ponder these things, I am simply grateful that I am not in government.

Can you share 3 of the best words of advice you’ve gotten along your journey? Please give a story or example for each.

  1. If you’re trying to do right, you’ll do it more often than not.
  2. Trust your intuition — whatever your gut is telling you, it’s probably correct.
  3. Bad news doesn’t get better with time.

We are sure you aren’t done. How are you going to shake things up next?

You are absolutely right, we have very big and ambitious plans at Penny. We are aiming to be the go-to platform for anyone who wants to master their money — and we believe that the best way to do this is to make it approachable. Money is a scary subject for a lot of people, but it really doesn’t have to be — unfortunately, the reason why most young people find it so intimidating is because the education system has completely failed in imparting even the most fundamental financial literacy skills. In addition to my work at Penny, I am exploring a nonprofit role, also to promote financial literacy — and while I cannot divulge too much information about that just yet, it is something that excites me very much. I just want to do my best to ensure that anyone who works hard gets a fair shot at getting ahead in life!

Do you have a book, podcast, or talk that’s had a deep impact on your thinking? Can you share a story with us? Can you explain why it was so resonant with you?

I found Blink by Malcolm Gladwell really impactful, because it digs into the philosophy that first impressions and intuition can often be more useful for decision making than painstaking rational thought if used correctly. The human nervous system is capable of sizing up situations in seconds and making a successful judgement on the right answer. I found this theory both valuable and validating. As a young founder you are never going to have all the information to make decisions, and you’ll have to rely on and trust your intuition more than you may realize. This only works if you really do trust it.

Early in my life I endured a great trauma, and during those years I learned how important it is to be in tune with your instincts. When I read this book in college, it verbalized many of the things I had felt but had no words to describe. These days, life moves at a breakneck pace and the ability to trust my gut to make rapid judgements is critical to moving the company forward. So I really believe that my finely tuned intuition has become even more valuable as a founder.

Can you please give us your favorite “Life Lesson Quote”? Can you share how that was relevant to you in your life?

“Success is not final, failure is not fatal: it is the courage to continue that counts.” — Winston Churchill

You are a person of great influence. If you could inspire a movement that would bring the most amount of good to the most amount of people, what would that be? You never know what your idea can trigger. 🙂

At least for the time being, my work at Penny is primarily focused in the United States, and I am very excited about being able to help my fellow Americans master their money. However, if I could, and maybe this will happen someday — I would really like to also help people in developing countries, particularly those in rural, economically-deprived areas.

Microfinance is one model that has been proven to be successful in lifting millions of people out of poverty — and personally, I find the work of Professor Muhammad Yunus of Grameen Bank to be incredibly inspiring. If I were to manifest the future, I would certainly hope to one day be able to make an impact in communities and regions in the developing world, using finance and business as a conduit to facilitate social mobility.

How can our readers follow you online?

You can find me at @charlottedemocker and Penny at!

This was very inspiring. Thank you so much for joining us!

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