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Charlotte DeMocker of ‘Penny’: “Seek out expert advice when necessary”

…As far as the startup community is concerned, I understand that there is always going to be a large amount of emphasis on fundraising, investors, and valuations. I would advise that every founding team should choose their investors wisely. I have heard nightmare stories about how things can go very wrong because the investors are […]

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…As far as the startup community is concerned, I understand that there is always going to be a large amount of emphasis on fundraising, investors, and valuations. I would advise that every founding team should choose their investors wisely. I have heard nightmare stories about how things can go very wrong because the investors are not aligned with the management team. We are very grateful and appreciative of the fact that we have supportive investors who completely understand our mission.


As part of my series about the “5 Things You Need To Know To Create a Successful App or SaaS”, I had the pleasure of interviewing Charlotte DeMocker

Charlotte DeMocker is co-founder and Chief Operating Officer at Penny, an innovative digital media startup that seeks to improve people’s social mobility by reimagining and simplifying how we learn about money. Follow her on instagram @charlottedemocker.


Thank you so much for joining us! Our readers would love to “get to know you” a bit better. Can you tell us a bit about your ‘backstory’ and how you got started?

I’m a designer and storyteller by trade, having spent years crafting everything from investor pitches to My father worked in wealth management, and it inspired me to also pursue a degree in finance. It became clear just a couple years into my post-college work at a boutique investment bank that, while I enjoyed working with people and helping with their finances, that my true passion wasn’t to help the wealthy build more wealth, but rather to help the average person invest in and plan for their future. It didn’t seem fair to me that millions of people struggle just to pay their rent. I felt a calling to use my knowledge and skills to help those people.

What was the “Aha Moment” that led you to think of the idea for your current company? Can you share that story with us?

I don’t think there was a single ‘Aha’ moment, but rather, a series of moments. I worked in investment banking for a few years, and I saw over and over again that the current system exists only to serve those who are already wealthy. Meanwhile, there are millions of people who are working two, even three jobs — but unable to get ahead, simply because they lack financial literacy. The more I observed this in real life, including amongst my friends and colleagues, the more I realized that something needed to be done.

Can you tell us a story about the hard times that you faced when you first started your journey? Did you ever consider giving up? Where did you get the drive to continue even though things were so hard?

We started Penny during the worst months of the pandemic, so frankly, things were not easy at all when we first began our journey. We never once considered giving up. Penny was not a spontaneous, spur-of-the-moment idea — we had been thinking about this and making plans for years, and so we knew what we were getting into. And as for drive — when I look around me and I see so many people who, through no fault of their own, and for no lack of trying, have had their entire life trajectories put on hold thanks to this pandemic, my resolve simply strengthens. I know that I have an opportunity to make a difference, and that’s what keeps me going every day.

So, how are things going today? How did your grit and resilience lead to your eventual success?

Things are going fairly well. We managed to launch an app in just two months, even when no one else was in an expansionary mood and everyone was turning inward. I would like to think of that as a nice little win. But these are early days yet. We have a long, long way to go, and I know that we are going to have to work even harder in 2021.

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

I think Penny stands out because we are primarily driven by the principle of compassion. A lot of startups are driven by the promise of quick, life-changing money. At Penny, we know we are in it for the long haul. This isn’t about a quick flip. This is about solving a deeply-rooted problem.

First and foremost, we are compassionate towards our people — and we really seek to empower and support them as they strive to forge their own career paths. And in turn, our people are compassionate towards the millions of others out there who are desperate for a financial clean slate — to get their debt under control, to buy their first home, or to lead a life of purpose and meaning instead of constantly having to struggle to pay the bills.

One thing we did in the lead-up to the holidays was to reach out to specific individuals who had started GoFundMe campaigns because they were trying to start businesses, but were struggling for money. We specifically chose the ones whose campaigns were not doing so well. And in addition to making a donation, we also put together customized playbooks for them — covering everything from sales, to marketing, to cash flow management, to financing. This was a team effort, and involved not only Penny employees, but also, drew from the content that was contributed by our independent content partners (Presenters). Penny really is about people and community. I would like to think that makes us different.

Which tips would you recommend to your colleagues in your industry to help them to thrive and not “burn out”?

In one sentence — surround yourself with the right people.

Your support structure is very important. We all know that we are the sum total of the five people that we spend most of our time with. So I would say to anyone out there who is young and ambitious — spend time with people who are more ambitious, more intelligent, more successful. Learn from them,and allow their experiences to inspire and nourish you. If you are always the smartest person in the room, it’s probably time to try a different room!

What is your monetization model? How do you monetize your community of users? Have you considered other monetization options? Why did you not use those?

Penny currently offers a completely free streaming service. We will be launching a premium subscription service at some point in the future — but even when we do, users will still be able to stream our content for free. We are expecting that the vast majority of our user community will stay with the free service.

Monetization, and profit, are not our main objectives at the moment. We know that people are hurting financially due to the pandemic, and we are focused on trying to help our users improve their financial literacy and ultimately, to master their money. We are in this for the long-haul, and we are very blessed and fortunate to be backed by solid and patient investors who understand our mission — and who appreciate that Penny is about solving a widespread problem, and not about opportunistic short-term returns.

Based on your experience and success, what are the five most important things one should know in order to create a very successful app or a SaaS? Please share a story or an example for each.

Firstly, I think Jeff Bezos and many others have said this, so I can’t claim that this is an original suggestion — but really, as cliche as it sounds, the emphasis has to be on the user or customer. Make sure you are solving a real problem. Be humble, respect the data, and don’t assume that customers want what you want. The market never lies.

Secondly, as far as the startup community is concerned, I understand that there is always going to be a large amount of emphasis on fundraising, investors, and valuations. I would advise that every founding team should choose their investors wisely. I have heard nightmare stories about how things can go very wrong because the investors are not aligned with the management team. We are very grateful and appreciative of the fact that we have supportive investors who completely understand our mission.

Thirdly, no matter how fancy your product is, you are not going to get very far unless you have a good team. Don’t just hire people for their skills or qualifications. Instead, spend some time digging deeper. Try to get an understanding of what makes them tick. Skills can be learnt over time, but culture fit is something that is either there or isn’t there. As the company grows and evolves, its people must grow and evolve with it.

Fourthly, seek out expert advice when necessary. No entrepreneur or co-founder is going to be an expert in all areas of business management — that simply isn’t realistic. I have learnt that it is extremely important to put the ego aside at times, and learn from people who have specific knowledge within their respective domain areas. And their advice is only going to be valuable if it’s applied and put to use.

Finally, and I would say this matters especially to me because of what Penny is about — set out on your entrepreneurial journey in a financially-literate way. What are your personal financial goals? Are you looking to make a comfortable income for yourself? Would you like, perhaps, to be able to earn that income passively or semi-passively? Or are you trying to take a shot at a life-changing exit? Whatever your goals are, make sure you are clear about them. Be intentional about what you’re doing. Because each path looks very different — and requires its own approach and playbook. Each also carries its own risks and downsides.There is never a ‘right’ or ‘wrong’ — it is about what works best for you. Having your personal financial goals mapped out is not a guarantee of success. But at least it ensures that you will go in with your eyes open. That is very empowering.

How can our readers follow you on social media?

You can find me on Instagram at @charlottedemocker and Penny at @penny.app or look out for my posts on the Penny blog, where I share my views on a wide array of money-related subjects, including entrepreneurship.

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

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