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Charlotte DeMocker of Penny: “Earning Respect”

Earning Respect. Being taken seriously and treated with respect can be a battle as a young, female founder. The explosion of the startup world and the high failure rate means that unless you already have a successful company or exit to point to, people may doubt you and consider you to be just one more […]

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Earning Respect. Being taken seriously and treated with respect can be a battle as a young, female founder. The explosion of the startup world and the high failure rate means that unless you already have a successful company or exit to point to, people may doubt you and consider you to be just one more dreamer with an idea. I’ve found it helps to act the part — dress well, carry yourself with confidence, and don’t downplay what you are building.

I remember in the early days of the company, I was approached by an employee in the kitchen who I had not yet met. He asked me what my role was at the company, and I must have appeared slightly amused as I informed him my role was COO and co-founder. It really wasn’t his fault that he didn’t know, and it made me realize we were communicating in silo’s. Since then we have incorporated more all-company meetings so everyone is used to hearing from leadership regularly.


As a part of our series called “5 Things I’ve Learned as a Twenty Something Founder”, I had the pleasure of interviewing Charlotte DeMocker, co-founder and Chief Operating Officer at Penny, an innovative 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 with strong skills and work ethic struggling to get ahead, often only because they lacked the financial knowledge that should have been provided in school. Motivated by this inequality, Charlotte embarked on a mission to demystify finance for the many, not the few.


Thank you so much for doing this with us! What is your “backstory”?

Glad to be here! 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 to use my knowledge and skills to help people.

Can you share the funniest or most interesting story that happened to you since you started your company? What lessons or takeaways did you take out of that story?

The global pandemic has certainly been interesting to navigate, as a young company. But startups are built to adapt quickly, so we’ve found creative ways to push forward, maintain operations, and still empower team cohesion. The lesson in that is there’s always a solution to keep you moving forward: a new tool, a product adaptation, or a different messaging strategy. You have to be willing to get creative, check your ego, and accept that your vision for the company may need to adapt if you’re thrown a curveball.

What do you think makes your company stand out? Can you share a story?

Penny is truly a mission-based company. We are the only audio-streaming app in the United States that is exclusively dedicated to helping people master their money, freeing them from debt, and empowering them to live more financially independent and secure lives. 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 full-time workers live paycheck to paycheck, and 53% of college graduates are either unemployed or under-employed — and that was before Covid. The truth of the matter is that money is a scary and stressful subject for a lot of people, especially for young people who are saddled with college debt, and working multiple jobs just to stay afloat. Our goal is to provide everyone with the financial knowledge they should have been offered in school.

When we launched our app, one unexpected thing that happened was that we had someone from Australia leave a comment on our Instagram asking when Penny would be available there. That was a humbling moment, because it left us no doubt as to the scale of the problem that we’re setting out to tackle. Our app is fairly new, and we’re a ways from international expansion at the moment — but already, people in other countries are expressing interest and saying that they could really benefit from Penny. That demonstrates just how widespread the financial epidemic is. I guess that just means we’re going to have to work harder and faster!

None of us are able to achieve success without some help along the way. Is there a particular person who you are grateful towards who helped get you to where you are? Can you share a story?

Absolutely, it’s important to have a strong community you can turn to when you’re embarking on a journey like this. Friends, family, and mentors can be very powerful influences on your professional development. I believe you should surround yourself with people who are thoughtful, positive, and passionate — and try to seek out a variety of perspectives and backgrounds. My mentors include my father and sister, a beloved finance professor, a close friend who is a high-profile lawyer, and a former boss who is a powerhouse creative director.

My father and sister have always been champions of mine, and I’m lucky to have such close relationships with them. My father and I talk frequently and he gives the best advice… even when I don’t ask for it. When I first told him about the idea for Penny he had a million questions, not because he doubted its validity but because the concept excited him and piqued his curiosity. The more we talked it through over the coming months, the more certain I was about it. Looking back I really feel that his expertise in the space, and his energy for debating the finer points of our possible product approach, were what convinced me to take the leap. Well, that, and his countless hours of advice and reassurance about the leap itself. I’m lucky because he is obligated to be my rock, as my father, but he’s an incredible mentor in giving back to others and all things finance.

Are you working on any exciting projects now?

Launching a company is a full time job and then some — so I am committed to Penny completely at the moment. But outside of that, I’m exploring an advisory position with a nonprofit that promotes financial literacy. And I’d like to become a certified scuba diver by the end of the year!

How have you used your success to bring goodness to the world?

I genuinely believe that financial literacy is a key that is capable of unlocking a lot of goodness in the world. The idea of ‘capitalism’ gets a bad rap these days, and more and more young people are saying things like ‘money doesn’t matter’ or ‘I don’t need to be rich’. But really, money is only as good as what it can buy — and the number one thing that it can buy is freedom.

When you are financially stable, you have the freedom to leave your job if you’re not happy; you have the freedom to buy something nice for those you care about; you have the freedom to be kind to yourself when you’re feeling a little low. Last year, I had a bad accident, and I required multiple surgeries as well as extensive physical therapy to get me back to a place where I could be fully mobile again. I’m so, so grateful that I can afford the extra physical therapy sessions that my insurance won’t cover. Without that, my recovery would have been delayed and my mobility could have been permanently impacted. And I say this with an attitude of humility, because I understand that there are so many people out there who don’t even have healthcare, and who literally can’t afford an unplanned medical emergency. So I really think that being financially literate is the best and most liberating thing that anyone can do for themselves, and it’s a real shame that it isn’t taught in schools. That is what I’m trying to bring to the world through my role at Penny.

Do you have a favorite book that made a deep impact on your life? Can you share a story?

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. Now, 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 share 5 of the most difficult and most rewarding parts of being a “TwentySomething founder”. Please share an example or story for each.

I’ve encountered a number of challenges along the way. Those include:

  1. Earning Respect

Being taken seriously and treated with respect can be a battle as a young, female founder. The explosion of the startup world and the high failure rate means that unless you already have a successful company or exit to point to, people may doubt you and consider you to be just one more dreamer with an idea. I’ve found it helps to act the part — dress well, carry yourself with confidence, and don’t downplay what you are building.

I remember in the early days of the company, I was approached by an employee in the kitchen who I had not yet met. He asked me what my role was at the company, and I must have appeared slightly amused as I informed him my role was COO and co-founder. It really wasn’t his fault that he didn’t know, and it made me realize we were communicating in silo’s. Since then we have incorporated more all-company meetings so everyone is used to hearing from leadership regularly.

2. Making Sacrifices

When you’re a founder, it becomes very difficult to maintain a healthy work/life balance. Everything you do is about making your idea come to life, and there is no set working hours for that objective. Things happen, good or bad, at all hours of the day. You’ll have to make sacrifices around your social life, sleep schedule, and exercise preferences. Luckily age is an asset here, and I’ve found my energy and passion to be extremely valuable in breathing life into the company.

During the two weeks leading up to our launch, I remember I slept an average of two hours a night because there were so many moving pieces. I was a high-functioning zombie, working on everything from in-app content to website code to social media strategy. Seeing it all come together on launch day was the sweetest reward (sleeping through that weekend takes a close second).

3. Learning How to Say “No”

If you build your team well, you’ll have some incredible brains to leverage and invest in. This is a reward, but can also be a difficulty if you aren’t used to saying no. People will bring you great ideas that the company simply doesn’t have bandwidth for, or ask you for tools or tech that would obviously be great but that you simply can’t afford. But if you shut people down the wrong way, they may not bring you future good ideas. Learning to say no while appreciating the person is a difficult balance, and I am still learning to do it gracefully when moving fast.

4. Letting Go of the Desire to Be Perfect

One of my best and worst qualities is perfectionism and holding myself to absurd standards, anytime I attach my name to something. It probably started during my time in investment banking and the extreme attention to detail required to put together a pitch deck. When I first started out as an entrepreneur, however, this resulted in many sleepless nights across all kinds of projects. Over time I’ve had to be very intentional about developing my time management skills — now I try to distinguish when there’s a need for especially high-quality deliverables vs. when it simply needs to get done as quickly as possible.

5. Prioritizing Tasks and Staying Focused

It feels like there are a hundred critical things to do at every moment, and most of them are entangled with or rely upon each other in some way. It can be such a challenge to untangle the web of priorities, keep your team focused, and push forward in measurable ways each day, week, and month.

A former colleague (who manages an enormous team) once told me that each week he identifies three large things he will get done, and then each day of that week he assigns himself three things to complete that tie into those larger goals. I’ve found this approach helps me to stay focused on the larger picture each week, even as I’m getting pulled in a million directions moment to moment.

While there have been challenges, the experience has also been infinitely rewarding. I’ve been excited about:

  1. Building Something I’m Passionate About

Being passionate about an idea, building an incredible team, and seeing the company come to life is all so rewarding and that goes without saying. The additional benefit is that you are working for your idea, rather than working for someone else. At the end of the day, you are building something that is only limited by your imagination and passion.

2. Creating Value and Helping People

Penny is a mission-based company focused on helping people to improve their financial circumstances and, in doing so, hopefully change their lives. So this expands on the above because my passion to build something I believe in is amplified even further by the potential impact our idea can have and the good it can bring into the world. We want to touch millions of lives and provide them the financial freedom that should be everyone’s right.

3. The Network and Community We Are Building

I get to meet interesting, inspiring people who I wouldn’t normally get to meet. Let’s face it, when you’re in your 20’s in a corporate job you aren’t going to be handed access to these kinds of people. There are so many synergies that can develop when you have an amazing network of passionate, connected people across every industry out there.

4. Constant Learning, Personal Growth, and Improvement

I believe one should never stop learning. As a founder I learn new things every day, but I try to be intentional about learning and iterating on my leadership style and observing the effects of my actions as a manager. I thrive in fast paced and intellectually curious situations, and I believe anyone who feels the same way will thrive as an entrepreneur. Boredom is unlikely.

5. Overcoming Fear

Founding a company is a great opportunity to practice mastering your fears — especially the fear of failure. Struggling with your fears can become a paralyzing activity, and it’s one you won’t have much time for — you simply have to push past it. All fear is rooted in something deeper. As Winston Churchill said, “Success is not final, failure is not fatal: it is the courage to continue that counts.” Finding the courage to move forward in spite of your fear is what you will learn the most from.

What are the main takeaways that you would advise a twenty year old who is looking to found a business?

First of all, make sure you begin with the end in mind. Make sure you are financially literate. Understand the personal financial implications of the path that you are choosing to take. After all, business is about money and anyone that says they are looking to start a business but doesn’t care about, or understand, money is probably not being honest with themselves. But the question is how will the money come? Are you looking to engage in arbitrage by purchasing items and then selling them at a higher price? Are you looking to charge fees for your services? Or do you intend to do a startup, and take a shot at that life-changing exit, with the full knowledge that you will need to raise millions of dollars from investors in order to even have a chance? The choices you make at the beginning will determine your path, and your path will determine your destination. Don’t go in blindly, just because you’re obsessed with an idea.

Secondly, surround yourself with positive and high-quality people. If you’re the smartest and most ambitious person in your friend group, you probably need to expand your social circle and find people who will push you. When you’re in your 20’s, it’s easy to fall into the trap of avoiding having to make sober, mature life decisions. And it’s totally okay to say “I am not yet 100% sure what I want, and I’d like to explore for a bit longer.” That’s fine. But if you’re exploring and experimenting, do so intentionally. Make sure that you have people in your life that you can count on for guidance, advice, and constructive criticism when necessary. Peer accountability is very, very important.

We are very blessed that some of the biggest names in Business, VC funding, Sports, and Entertainment read this column. Is there a person in the world, or in the US whom you would love to have a private breakfast or lunch with, and why? He or she might see this. 🙂

I know we’ve recently lost her, and she’s not in business or sports, but it would have to be Ruth Bader Ginsburg. I would really have liked to pick her brain, but also to ask her, woman-to-woman, where she found the courage and tenacity to keep going — even as she saw many of the things she stood for get torn down as a result of cynical political machinations. I’ve been through a lot in life, and through my own experiences I’d like to think I’ve become rather resilient. Justice Ginsburg, however, was truly a paragon that fought relentlessly and with ingenuity, even when it looked like the obstacles were insurmountable, and the outcomes were a foregone conclusion.

What is the best way our readers can follow you on social media?

You can find me on Instagram at @charlottedemocker and Penny at @penny.app.

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

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