Don’t let age be a hindrance — Starting a business at age 25 in the higher education industry wasn’t easy. We were advising clients more than double our age who had been working in the industry for longer than we had been alive. Despite a few situations where we were mistaken for students, we learned to embrace our youth and find confidence in the fact that older generations depended on our knowledge and skills to help keep them current and innovative.
As a part of our series about “Optimal Performance Before High-Pressure Moments,” I had the pleasure of interviewing Clayton Dean.
Clayton Dean is the co-founder and chief operating officer at Circa Interactive. After chasing his dream of working in professional sports (NBA, MLB, USA Swimming) in the two years after college, Clayton found his true passion: higher education. Over the last decade, Clayton has partnered with dozens of top institutions to implement innovative marketing and enrollment strategies and consistently exceed enrollment goals. Clayton is a former Division I swimmer and holds a bachelor’s in business administration and sports marketing from Duquesne University, a master’s in organizational leadership and management from Lewis University, and a certificate in new media and internet marketing from the University of Denver. In 2018, Clayton was named a San Diego “Top Business Leader Under 40” finalist and also guided Circa Interactive to a №1,929 ranking on the 2018 Inc 5000. In his free time, Clayton serves on the board of the YMCA of San Diego County and the Prevent Drowning Foundation of San Diego, competes in triathlons, and spends time with his wife and son.
Thank you so much for joining us in this interview series, Clayton! Before we dive into the main focus of our interview, our readers would love to “get to know you” a bit better. Can you tell us a bit about your childhood backstory?
Thank you for having me! Sure, I’d be happy to. I grew up just outside of Orlando, FL, and had two of the best parents around. They instilled a lot of the values and work ethic that I believe have helped me tremendously as a business owner and entrepreneur.
Growing up I was in and on the water every chance I could get — most of my days growing up were spent at the beach surfing or diving, wakeboarding on the lake, or swimming in the pool. I started swimming competitively around eight years old and continued through college at Duquesne University. Division I athletics is difficult no matter what sport you play, but swimming is known as one of the most demanding. We trained upwards of 30 hours a week and most of my days ran from 5:30 am to 9 pm between two practices, weight training, and class. While it wasn’t your typical college experience, I look back at the experience and can see how beneficial it was. You learn to push through when things are tough, how to set goals, navigate team dynamics, and put in the work to get results.
What or who inspired you to pursue your career as an entrepreneur or business leader? We’d love to hear the story.
Jason Fried — I devour anything he writes and has always admired how he approaches business and runs his company. In a world where everyone thinks you have to raise money and run a cutthroat business to be successful, he’s proven firsthand that it doesn’t have to be. I pinpointed his philosophy as one that I wanted to follow very early in my career and when the time came to start defining our principles and values, it was largely based on what I learned from Jason. To this day I find him highly motivating and appreciate how real he can be.
None of us can achieve success without some help along the way. Was there a particular person who you feel gave you the most help or encouragement to be who you are today? Can you share a story about that?
For me, it was the people in my life who supported me in our early years as a business when there we’re still a lot of unknowns and we were operating in uncharted territory. My parents were a huge support and remain so today. They may not fully understand exactly what we do or how we’re paid, but they’ve always remained confident in our abilities. Gino Pala, the former CEO of Dixon Ticonderoga, was also a major influence and supporter in our early years. He’s unfortunately passed away but was someone I reached out to often for motivation and ideas. He was the ultimate entrepreneur and extremely creative in navigating the world of business.
Can you share the funniest or most interesting mistake that occurred to you in the course of your career? What lesson or take away did you learn from that?
I had a job right out of college with the Orlando Magic in their ticket sales department. It was a great opportunity to learn how to sell and get some experience to better understand which path I wanted to take working in professional sports. I came into the job highly motivated but entirely too immature. I had many senior-level connections within the organization and an opportunity to grow, but couldn’t get past the freedom of life after college and replacing 30 hours a week of swimming with a part-time job and partying. Within a few months, the charade was up. I was politely offered the opportunity to resign, which I did, and looking back I still can’t believe how well they treated me during that process. I’m not sure I would have done the same for some idiot who treated their job like summer camp rather than work.
I never sold one ticket.
The road to success is hard and requires tremendous dedication. This question is a big one, but what advice would you give to a young person who aspires to follow in your footsteps and emulate your success?
- You must be willing to sacrifice — Balance is important but you must fully immerse yourself into whatever you’re doing to make it successful and beat the competition. That sometimes requires skipping a weekend with your friends, missing dinner, or cutting a hobby that you enjoy.
- You must be willing to work harder than everyone else — Throughout my career, I’ve come to realize that most of the highly successful people that I know aren’t necessarily the smartest. You can control if someone else is smarter than you, but you can control your work ethic.
- Communicate well, and often — Respond to calls and emails promptly, keep it succinct and send important client communication to a copyeditor (if it’s a long message). Hire a $10/hour copyeditor on Fiverr or Upwork, if needed.
- Do what you say you’re going to do — Make sure you hit deadlines and always follow through. Failing to do so is a very quick way to lose trust and confidence in personal and professional relationships.
- Don’t let age be a hindrance — Starting a business at age 25 in the higher education industry wasn’t easy. We were advising clients more than double our age who had been working in the industry for longer than we had been alive. Despite a few situations where we were mistaken for students, we learned to embrace our youth and find confidence in the fact that older generations depended on our knowledge and skills to help keep them current and innovative.
Is there a particular book that made a significant impact on you? Can you share a story or explain why it resonated with you so much?
Simple Numbers, Straight Talk, Big Profits — The simplicity of this book is what makes it so powerful. While my accounting courses in undergrad were helpful, this book broke down what financial metrics are most important to ensuring a business is healthy and successful. It’s helped me more effectively work with our CFO and add more value to the financial management of our business.
Scaling Up (Verne Harnish) — it’s so easy to get caught up in the complexity and nuance of running a business and this book was instrumental in helping me understand what’s most important to my business and where I need to focus my time. I adjusted their framework to make it fit for my business and responsibilities but overall this book has been such a great tool that helped ensure our business scaled on solid principles and foundations.
Can you share your favorite “Life Lesson Quote”? Why does that resonate with you so much?
The Jar of Life story is one that really resonated with me and is more relatable now than ever before. You can read about it here. In short, there’s a jar with golf balls that represent your life — your family, children, health, friends, and passions. The jar and golf balls are then filled with pebbles, which represent other things that matter — your job, your house, your car, etc. Sand is then added, which represents all the small things.
If you put sand in the jar first, there’s no room for golf balls or pebbles.
If you spend all of your time on the small stuff you’ll never have time for the things that truly matter.
Pay attention to the stuff that matters. Go to dinner with your parents. Grab a drink with friends. The small stuff will always be there, your most important things in your life won’t be if you don’t give them time and attention.
What are some of the most interesting or exciting projects you are working on now? How do you think that might help people?
Back in early 2019, we identified a close connection between student retention and rising levels of stress, depression, and anxiety amongst college students and set out to figure out how we can help reduce student anxiety, stress, and depression to improve student outcomes and help colleges and universities increase student retention.
We were about halfway through product development when COVID hit, which had a major impact on student mental health and created an even larger need for student support. In collaboration with Mindful Labs, a Colorado-based biotech firm, we accelerated the development of Reset, which offers students a free, 100% online solution that enables them to get the mental health support that they need without having to step foot on campus.
Our goal is to help students better cope with all of life’s challenges, especially for the first-time college, low income, and full-time working parents, so they can complete their studies and accomplish their goals.
OK, thank you for all of that. Let’s now shift to the core focus of our interview. As a business leader, you likely often face high stakes situations that involve a lot of pressure. Most of us tend to wither in the face of such pressure and stress. Can you share with our readers 3 or 4 strategies that you use to cope with the burden of stress?
I’m 10 years into owning a business and this is something that I still struggle with and have to be hyper-aware of. I think most entrepreneurs and business owners can relate. It’s really really hard to turn off your work brain and not worry. There are dozens or hundreds of moving parts, dozens of people who depend on you for their livelihood, and your pride at stake. It’s a lot to handle and I don’t think many people who aren’t in our position can totally relate or understand.
Again, I’m still working hard myself to get better in this category but here’s what I’ve found to be helpful:
- Make exercise part of your daily routine — exercise will not only cleanse your body but also your brain. I do some of my best thinking on my bike or swimming laps in a pool.
- Compartmentalize — separating home and work has become increasingly more difficult since COVID began, but this is something that I still have to work on every week. Monday through Friday I’m 100% focused on work and it’s oftentimes hard to stop, especially when I’m overloaded. I’m doing a great job shutting off on the weekends and focusing on family, however.
- Limit your focus to the highest priority — prioritization is one of the best ways to help reduce stress and overwhelm. This is another area I have to continuously work on but as I’ve progressed in my career, I’m learning that there simply aren’t enough hours in the day to do everything that I want or need to. I’m constantly reshuffling priorities each day and I recommend that you do the same. You must remain flexible and agile and understand that when running a business, what you think is most important today may not be the most important thing when you wake up.
Aside from being able to deal with the burden of stress, can you share with our readers 3 or 4 strategies that you use to optimize your mind for peak performance before high pressure, high-stress situations?
- Preparation — for me, it’s all about preparation. Preparation equals confidence and confidence eliminates stress and anxiety. When I’m prepared and confident, I find that I can handle just about any situation.
- Sleep — it’s extremely difficult to be focused and quick thinking when you’re tired, so prioritize sleep every day. Don’t fall into the Silicon Valley trap of thinking that you’re only going to be successful by sleeping four hours a night. If you’re building a business for the long-term and want to be happy and not stressed, get some sleep.
- Exercise — There’s really no better way to clear your mind or prepare for a high-stress situation. When I’m on the road, I always make a point to stay at a hotel with a nice gym so I can get a workout in the morning of a big presentation or pitch. It helps me burn off anxiety, visualize the situation, and walk-in feeling confident.
Do you use any special or particular breathing techniques, meditations, or visualizations to help optimize yourself? If you do, we’d love to hear about it.
I’m really big into the impact of breathing techniques, although the way I do it isn’t conventional. What most people don’t realize is that lap swimming is highly meditative and involves continuous breathing exercises. It’s an activity that helps me clear my mind and work through any challenges I’m facing.
If I’m nervous before a presentation or high-pressure situation, I also just take a minute or two and take six long, deep breaths to help center myself. It’s simple but impactful.
Do you have a special technique to develop a strong focus, and clear away distractions?
One of the challenges of being a business owner is overwhelming and getting spread too thin. You wear many hats and feel responsible for everything happening within the business, so it’s super easy to lose focus or focus on the wrong priorities. Over the years I’ve picked up best practices that I’ve worked into my routine, including:
- Cleaning out emails first thing in the morning and at the end of each day — Email is probably the biggest distraction for any professional these days and prevents you from getting to meaningful work. Tackle priority emails first thing in the morning or at the very end of each day so that you maintain a high level of responsiveness but you also can shut off that part of your brain and focus on the things that will help move you or your business forward.
- Blocking time on my calendar for deep work — I have recurring time blocks each day that ensure I at least have an hour or two of the time allocated for meaningful work. As a business owner, it’s easy to spend your entire day in meetings and end the day feeling like you’ve made no progress on your goals. It’s frustrating and can be super draining. I typically block off the entire day on Wednesdays so that I have zero distractions and can spend two to three hours on my biggest priorities.
- Scheduling themed days — I actually picked up this technique from Jack Dorsey, the CEO of Twitter. Jack splits his time as CEO between Twitter and Square and has to be super strategic with his time. He assigns a theme to each day to ensure he’s giving the most important parts of each business the time and attention it needs to continue operating at a high level. I follow a similar structure:
- Monday — business health review, project check-ins, and client success
- Tuesday — partnerships and business development
- Wednesday — deep work; no meetings
- Thursday — team and 1:1s
- Friday — overflow, admin, and planning
Finally, turn off the notifications — Slack, email, text. It’s rare that anything will pop up in a work environment that is truly urgent and can’t wait a couple of hours. If your attention keeps getting pulled away every few minutes you’ll never truly get into a deep workflow that will move the needle on strategic initiatives.
We all know the importance of good habits. How have habits played a role in your success? Can you share some success habits that have helped you in your journey?
Following the same morning and end of day routine. Routine is crucial to productivity and focus, so it’s vital that you identify what you need to do each day in order to set yourself up for success. My routine includes:
- Clean out email
- Read/audiobook 30 min
- Prep for today’s meetings
- Tackle the most important action item for the day (high impact, high value)
- 15 min of French
End of Day:
- Clean out email
- Plan 2–3 priorities for tomorrow
- Review notes
- Review what I accomplished today
What is the best way to develop great habits for optimal performance? How can one stop bad habits?
Limiting focus is key here. It’s easy to try and focus on too many things at once, but limited to 1–2 habits at a time is key. Use a tool like Notion to create a habit tracker that’ll help you keep track of your progress.
I’d also suggest making your intentions public. Post on social media, tell your friends and family. You’re not only creating a support network but you’re also helping to keep yourself accountable. Social pressure is amazingly powerful.
As a business leader, you likely experience times when you are in a state of Flow. Flow has been described as a pleasurable mental state that occurs when you do something that you are skilled at, that is challenging, and that is meaningful. Can you share some ideas from your experience about how we can achieve a state of Flow more often in our lives?
As you progress through your career, it seems like you get pulled into more and more meetings, and getting focused becomes harder and harder. If I’m not careful, I can easily go an entire week without more than 30 min at a time to get actual work done.
To get into a state of Flow it’s absolutely vital that I schedule it ahead of time, or it won’t happen. I typically block off the entire day each Wednesday and prioritize one or two strategic projects that day that require my undivided attention. I shut off my phone, close my email, and focus.
Ok, we are nearly done. You are a person of great influence. If you could inspire a movement that would bring the most amount of good for the greatest number of people, what would that be? You never know what your idea can trigger.
Expanding financial literacy. If I didn’t have parents who instilled sound financial discipline in me from an early age, would I know how to balance a checkbook or understand the importance of time to take advantage of compounding interest? Simple financial concepts such as saving, debt management, investment strategy, and more aren’t being taught in schools or homes around the U.S and could benefit millions of people. I’d love to see financial education prioritized alongside traditional subjects in k-12 curricula.
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 just see this, especially if we both tag them 🙂
It’s a toss-up between Bill Browder and Bob Iger. Bill’s book Red Notice is one of my favorites and I’ve always admired his fearlessness and candor. Bob Iger’s biography was amazing and showcased his ability to maneuver one of the largest organizations in the world and some of the biggest business deals of our time with tact and grace while maintaining his integrity and treating people right. It’d be great to talk shop and pull as much knowledge from him as possible.