Chad Cascarilla Shares Leadership Strategies To Improve Your Company’s Culture

Chad Cascarilla CEO and Founder of Paxos

Recently I had the opportunity to interview Chad Cascarilla from Paxos for the ongoing series: CEOs Share Leadership Strategies To Improve Your Company’s Culture.

Chad Cascarilla is the CEO and Founder of Paxos, a financial technology company delivering pioneering blockchain solutions for global financial institutions. He is also the founder of itBit, the first fully-regulated global cryptocurrency exchange. Paxos recently closed another round of financing that will be officially announced in the near future.

Krish Chopra: What are the 3 most important values that your company’s culture is based on?

Chad Cascarilla:

· Search for the Truth — Obsess over finding the answer to the ‘why’ of any solution you propose, instead of attaching yourself to an idea or agenda. This is the most important value that we try to instill into every employee.

· Real Time Candor — We owe it to each other to give ‘brutally honest’, ‘radical’, ‘real time’ feedback about how we work with each other. Real respect means complete candor even if it means having a difficult and uncomfortable conversation.

· Be an Owner — Owners are comfortable with saying “this is my problem, even if I can’t solve this on my own.” Saying that lets them explore new or different ways to solve the problem. Renters, on the other hand, are more comfortable with pointing out problems and expecting others to solve it.

Krish: Managing millennials can often be a polarizing topic. Can you elaborate on your advice for managing the “millennial mindset?”

Chad: I think ‘managing millennials’ has become entirely overblown. Millennials want the same things every other working generation has wanted before them. Respect, professional growth, transparency, work/life balance, and the opportunity to work with great people. Information has proliferated so the demands may seem more ‘entitled’ than past age groups, but it’s really because they are more informed about what is happening in different industries and workplaces.

Krish: What are your “5 Ways to Improve Your Company’s Culture” and why.


· Host an all-hands team meeting every other week. This keeps the team on track, and gives them an opportunity to ask questions and learn about the business as we grow.

· Constantly force your team to provide feedback to senior leaders and then act on that feedback. Nothing makes a team feel more involved and invested than providing an open forum for discussion.

· Sit out in the open. Meetings can be held in private rooms, but no one should be sequestered away to work in silence all day. Working from a desk out in the open gets more people involved in the conversation and creates a more approachable dynamic for all levels at the company.

· Plan cross-functional events to increase productivity. We had our operations team go bowling with the engineers they worked with, and it immediately made the teams closer and more communicative. It’s comfortable to only work and socialize within your team, but great things can happen when you put different people with different backgrounds together.

· Allow for spontaneous fun. We are very serious about doing great work for our clients, but we don’t try to be serious all the time because it doesn’t make work a place that people look forward to coming to each day. For example, we let employees take their kids to work for a day, and each team planned activities for entertainment. It was fun to see a bunch of kids laughing and playing in the office. I wouldn’t say it was the most productive work day, but it lightened the mood for everyone.

Krish: Strong company culture is something that everyone likes to think they have but very few have it. Why do so many organizations struggle with creating strong, healthy work environments?

Chad: The simple answer is that it takes a lot of time and work. Every company struggles to articulate their culture (we definitely did), but once we finally started to hone in on our authentic company culture once we decided to make it a top priority. The culture can’t be something that you take casually because ultimately that will fall flat and employees won’t buy in. I thought long and hard about what inspired me to start the company and what traits were important and I think we are finally getting close. The important thing now is to stay focused on implementation by constantly talking about our culture and empowering our employees to be the ones who carry it forward. If it is not something that is threaded throughout the company it won’t be able to evolve and sustain.

Krish: What is one mistake you see a young start-up founders make in their culture or leadership practices?

Chad: I think the big mistake is promoting or implementing a culture that doesn’t reflect the founders. There is a reason the company was started, and if the founders’ own DNA and values are not reflected in the culture, it won’t work. You can’t copy culture from other successful companies because each company is unique.

Krish: To add to the previous question, young CEOs often have a lot of pressure to perform and often wear many hats. What’s a simple time efficient strategy they can start doing today to improve their company’s culture?

Chad: Make time for 1-on-1’s with your executive team where work is not the topic of discussion. Schedules are always insane, but making time for 1-on-1’s is the best way to improve company culture. Ask for feedback, give feedback, talk about personal/professional goals and make these meetings a regular priority. If you have to cancel from time to time, that’s fine, but make sure to always re-schedule. Those meetings will set the tone for those leaders to go out and have 1-on-1s with their own teams, and they will use those meetings with you as a frame of reference.

Krish: Success leaves clues. What has been your biggest influence in your leadership strategy and company culture?

Chad: Netflix (specifically their culture deck) is a company that we have used a lot in our approach to improving and shaping company culture. They have some incredible insights on freedom, responsibility and excellence that we respect and are doing our best to implement in our own organization. They have obviously found ways to pivot, expand and scale their business over the years, and it’s our hope that we can achieve similar levels of success in our own industry.

Krish: What advice do you have for employees that have bad bosses? How can they take control and improve a bad situation?

Chad: Bad bosses are everywhere, but I think there is something to be learned from every situation. If a positive attitude and constructive feedback are not acknowledged or well received, you may be in a situation that will never improve. First, try to understand the problems, be self-reflective, bring some empathy, and then if things still suck, move on! There are plenty of smart, inspiring people in the world who will take an interest in you and your career.

Krish: Okay, we made it! Last question — what’s one unique hack you or your company does that has enhanced your work culture?

Chad: No more diet coke or artificial ingredients in the kitchen. There was a revolt at first, and I know we aren’t the first, but we decided to make a conscious decision to only provide fuel that is great for people’s minds and bodies. They are free to consume whatever they want, but we wanted to send a message that being mindful starts with how you choose to nourish yourself. We already have people that feel better and are more energized during the day. Food is a perk, but it’s a perk that we felt needed to reflect our goals and ethos as a company.

A note to the readers: Improving company culture happens at any level in an organization. If you learned one thing in this interview, please share this with someone close to you.

A special thanks to Chad Cascarilla again!

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