From Athlete To Entrepreneur: Dan Whalen of Harbor Bay Hospitality On The 5 Work Ethic Lessons We Can Learn From Athletes

An Interview With Edward Sylvan


Quitting is easy. Improving, fighting through adversity, building mental toughness — all of that is hard. And the only way to do it is to struggle, fail, repeat, and get better through the process.

As a part of our series about the work ethic lessons we can learn from professional athletes, I had the pleasure of interviewing Dan Whalen.

Born and raised in Cleveland, OH, Dan Whalen is the Vice President of Design & Development and President of Hospitality of Harbor Bay Hospitality. A creative at heart with an entrepreneurial spirit, Dan is passionate about his projects and elevating the restaurant scene in his beloved hometown. His diverse past experiences, from journalism to the football field, enable him to provide an inspiring vision for his entire team.

Thank you so much for doing this with us! It is a great honor. Our readers would love to learn more about your personal background. Can you tell us the story of how you grew up?

I grew up in a lower-middle-class family on the east side of Cleveland. We didn’t have much money at all, but as a kid, you really don’t have a concept of what that means. It wasn’t until I was in high school that I understood how hard, my mother specifically, worked to make sure we were able to have the things we needed and to play the sports we wanted to play. My parents got divorced when my brother and I were young (I was 10, he was 6), and my mom remarried a few years later. My stepfather passed away from alcoholism when I was 22. So, you could say that neither I nor my brother ever really had a solid father figure in the house with any consistency. We are very close with my mom, and we have always just had the approach to put our heads down, work hard, keep busy through sports and competition, and not rely on anyone else to define our success. Growing up it was all baseball for me until high school. When I was 13 our baseball team won a national championship, but by the time I got to high school, the allure of the lights on Friday nights made me turn my sights to football. Not to mention, we had a varsity baseball coach that was more concerned with getting everyone playing time than he was with competing and winning games, so that took a bit of the edge away from baseball for me. I had always played football growing up but never fell in love with it until high school. When I got to high school, we were terrible. We didn’t win a single game in 7, 8, or 9th grade — which is an amazing feat in and of itself — but by the time we got some real coaching at the varsity level, something flipped for us, and me specifically, and we ended up going undefeated as seniors and being ranked as high as #2 in the state. That team success led to accolades for me, being named First Team All-State, and it also was key to me being recruited to play in college.

What or who inspired you to pursue your career as a high level professional athlete?

I don’t have a romantic story here that’s going to read very well, because it’s hard to pinpoint for me who inspired me to pursue my athletic career. That part was always in me. I am a competitor. I seek challenges and I want to improve things until I get them right or perfect them. I want to dominate whatever I’m doing, and I want to make sure people know it without me having to say a word. The inspiration came from those who helped me get the most out of me as a person and as an athlete — those who helped me hone my skill set or helped to motivate me when I may have felt discouraged. Those people specifically are my mom, my brother, my high school coach Matt Duffy and my college quarterback coach Dave Dicarlo. Whether it be through the things they taught me, the way they pushed me, or in my brother’s case — me wanting to lead by example and be someone for him to look up to — that’s what not only kept me going, but what elevated me through the years.

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?

I alluded to it before, but most of my success in football and a lot of how I learned to deal with problems and challenges off the field came from the relationship, coaching, and mentorship of Coach Dicarlo. By being hyper-concerned with the details and maintaining an intense focus on the things that most other quarterbacks weren’t working on, and by helping me stay centered mentally, I learned a lot, and I perfected fundamentals and techniques that led to all the positive outcomes I ever experienced on the field through and after college.

Can you share the funniest or most interesting mistake that occurred to you in the course of your sports career? What lesson or take away did you learn from that?

It’s funny now, but looking back, at the time it was probably disrespectful and extreme. But there was a week or so during college that my head coach was just relentlessly badgering me during practice about some things that I wasn’t doing to his liking — this was after we had already had some success and I’d proven myself — but for whatever reason, he wanted to make an example of me. After a few days in a row of just hammering me verbally in front of everyone at practice, he had wanted me to throw the ball away instead of taking a sack. So, I called everyone back to the line of scrimmage, I re-ran the play that was called, and I took one step and launched the football off the press box at the top of the bleachers. Then I walked away. That was the kind of thing that, had I done in high school, Coach Duffy may have literally killed me — and frankly, I would have never done it then. But my college head coach and I had a different relationship, we butted heads a lot, but in the end, there was a mutual respect that grew as time had gone on. I laugh about it with my friends now, but in hindsight, I probably should have just kept my cool and taken the yelling.

OK, thank you for all of that. Let’s now shift to the core focus of our interview. As an athlete, you 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 optimize your mind for peak performance before high pressure, high stress situations?

Pressure comes in different types. So, strategies differ depending on what’s really at risk, but here are a few ways I would advise:

  1. Always try to take the time to assess the situation if you can. Never rush. This includes trying to understand all the outcomes, as many of the potential challenges that are in your way, and how you might navigate them.
  2. Be constantly working on your self-awareness. What you’re good at, what you’re not, the way you’re feeling in these types of moments, and how that impacts your ability to execute.
  3. Calmness is going to resonate through to your team and those around you. If you’re calm, there’s a better chance they will be too. In moments of chaos, you can either just stampede with the herd, or you can take a deep breath and be calculated in your approach. It’s linked to self-awareness, but if everyone else is in a panic — whether it be due to a deadline, a business interaction, or any other instance — it is usually true that cooler heads will prevail.
  4. Be assertive, make quick decisions, and don’t be afraid to pivot if it appears your decision was the wrong one.

Can you tell us the story of your transition from a professional athlete to a successful business person?

That’s quite a long story — and a good one — but what I can say is that my life in sports prepared me for everything I do every single day. I think back to all the times we ran sprints, and my coaches would yell “FINISH THROUGH THE LINE!” As a leader, you must keep pushing, you must finish, and you must be the one who motivates others to do the same. That mentality is what gets things done. It’s the way that you find creativity in yourself when there are obstacles in your way. And when you have opportunities that may not come around again, you have to find the confidence to jump on them. Missed opportunities in the past have eaten at me and they have helped to frame the mindset I have now that when I see one, I take it.

What are some of the most interesting or exciting new projects you are working on now?

We are currently building our hospitality brands that include a few different concepts here in Cleveland. Edda Coffee Roasters, which is a brand we want to grow, Pioneer, a wood-fired casual sports bar, and Jaja, an Argentinian steakhouse and lounge. We also operate one of Cleveland’s top wedding and event venues, and we are exploring the idea of creating our own hotel brand as well. That’s all on top of our core business of real estate development, which I oversee. We are looking to build large, high-profile, mass-timber projects in markets around the country that build off our most recent project, INTRO, here in Cleveland. It’s a busy, exciting time.

Do you think your experience as a professional athlete gave you skills that make you a better entrepreneur? Can you give a story or example about what you mean?

I think being an athlete in general, and specifically one that participates in team sports, better prepares people for the trials and tribulations of the business world. In athletics, to be consistently successful, you must struggle together through ups and downs, you must build trust, confidence, and respect in one another, and you must be ok with the fact that while you may be able to lead, you can’t do everything. Preaching accountability and being clear with expectations are two things I beat the drum on constantly, and I think not only demanding those but being an absolute leader by example in doing them is key.

Ok. Here is the main question of our interview. Entrepreneurs and professional athletes share a common “hustle culture”. Can you share your “5 Work Ethic Lessons That Entrepreneurs Can Learn From Athletes”? Please share a story or an example for each.

  1. Quitting is easy. Improving, fighting through adversity, building mental toughness — all of that is hard. And the only way to do it is to struggle, fail, repeat, and get better through the process.
  2. I don’t buy into the mentality that ‘everyone has to pay their dues’ or ‘work their way up the ladder.’ When you see high performers who can take big leaps, there’s not always a reason to make them take the same small steps that other people may have to take to get to the same place. Work smarter, and when you find people who excel and can help the company go places, give them the resources, tools, and autonomy to lead. When I’ve been a part of great teams in the past, the players with the most talent, best instincts, and hardest work ethic rose to the top. It should be the same in any organization.
  3. Be resourceful. This one isn’t always easy to learn, but when problems arise, you have to be able to think on your feet, be strategic about your approach, and find the answers or solutions based on what’s in front of you. You’re not always going to have all the information you need or the perfect conditions to execute whatever it is that needs to be done. You have to figure stuff out and find who or whatever it is that can help achieve the goal.
  4. Do your job. So many times, I see people trying to do everything or play the superhero. In football, it was always pounded into our heads to focus on our jobs on a given play. If someone thinks they need to take on someone else’s role, then the play breaks down or people end up out of position. It’s a two-fold challenge though: you can’t get distracted from what it is that you’re supposed to be doing, and you need to be accountable to your team, so they know that you’re going to execute. On the field, it became very clear who was unable or unwilling to do their job consistently. Being unable is one thing that can be fixed through practice. Being unwilling, that’s entirely another.
  5. Relentlessly pursue mentors. Regardless of how much positive impact or leadership people take on, you can never stop learning and you can never gain too much knowledge from people who have ‘been through it.’ The same way you have a coach or a professor who teaches, you should find the same thing in business and push for someone to take you under their wing.

What would you advise to a young person who aspires to follow your footsteps and emulate your career? What advice would you give?

There is no blueprint on how to get to where you want to go. And there’s no straight line either. You have to have confidence in yourself — even when you aren’t sure about what you’re doing. What I’m talking about is the confidence that your instincts and skill set will help guide you through the uncertainty and difficulty. You have to learn when to kick doors down to get what you’re after, and when to finesse your way into the catbird seat. And from a more technical standpoint, while everyone else consumes their free time with social media and mindless scrolling, consume yours with exploration, curiosity, study, and obsessing over what it is that drives you. Focus on that, and don’t lose all your time doing things that aren’t going to matter or help you achieve your goals.

You are by all accounts a very successful person. How have you used your success to bring goodness to the world?

I think a lot of how I was raised plays a role here. I don’t think you need success to bring goodness to the world either. That said, it certainly can help your reach and influence when you’ve got a foundation of success to work from. Aside from things like volunteering and donating my time or money to things that I think can make an impact, I am making sure that our companies are doing things for the right reasons and doing right by our employees and the communities in which we work. From giving people with criminal records a second chance to trying to push for the most sustainable building practices in our real estate to partnering to reinvigorate community assets like Cleveland’s West Side Market, all we can hope to do is put in the effort to help make a positive difference in people’s day-to-day journey. When I’m six feet under, I just hope people can say their life was even just a little bit better for me being in or around it.

You are a person of enormous 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. :-)

Empathy. Emotional Intelligence. These are things that the world has lost. Everyone is so quick to take information in that they don’t even absorb it, they just react. Most people don’t care about perspective, and most people aren’t taking the time to assess, consider, discuss, and debate. Social Media has expedited this decline of consciousness by just obliterating us with thousands of pieces of meaningless content every day. It’s destroyed our attention spans, it’s dissected our spending patterns, spreads misinformation, and makes it easy for people to say things without having to face consequences for them as they might in person, it keeps people from doing meaningful or impactful things the same way any addiction would. I think for whatever good and whatever capitalistic benefit there is from social media, the societal deterioration and dumbness that it is creating at warp speed is on its way to becoming far worse. And empathizing with people, being emotionally intelligent enough to have deep conversations about life’s most challenging and complex topics, that stuff can only happen through being conscious enough to work on it. And with the instant gratification and dopamine hits we’ve been conditioned to seek all day every day, it only further limits our ability as a society to get back on track.

Can you share your favorite “Life Lesson Quote”? Why does that resonate with you so much?

“Don’t be careful, be smart.” Coach DiCarlo, who I mentioned earlier, always used to tell me to ‘be careful’ all the time on the football field. It became an inside joke of ours because I told him ‘I’m never careful when I’m playing. But I’m always smart.’ So, we collectively amended the phrase to be more applicable to the way I approached the game. The subtlety for me was important. ‘Being careful,’ the way I took it, meant to play hesitantly, or to be somewhat on eggshells — like I could be outsmarted or outfoxed. But I did the work. I prepared in a way that was unmatched by, not only the opponent, but my team as well. It was so I could anticipate any move they might pull to try and defend or beat us. I relied on preparation and my physical ability to be in a position to take calculated risks. And I think that’s the difference. Being careful means trying to eliminate any semblance of risk as far as I defined it. But being smart means understanding your potential blind spots and knowing what risks you can and should take, and whether or not the risks are worth it. When playing quarterback, being careful will get you nowhere most of the time, but if you can prepare and be in a position to attack when you need to, then being smart in those moments will be to your benefit. Football is just an example, but it translates to life and business as well. If you don’t take risks, you’re going to miss a lot of opportunities. But if you’re not smart about how you see, perceive, and assess those risks and opportunities, look out.

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 :-)

This is tough. I think it’s impossible to pick one, so I think I’ll give you a few with some context.

Francis Mallman is a human I absolutely admire. One of the most accomplished chefs in the world, who has essentially distilled his life down to the simplest of elements. Living in the remote mountains of Patagonia, cooking all his food over fires he makes by hand, and relishing time with family, friends, and romantic partners. Paired with great wine and no cell phone service. Sounds incredible to me.

On the business side, Dave Grutman or Michael Rubin would be my choices. Dave runs an empire of Miami-based hospitality concepts which are design-forward and draw the elite of the elite. He demands the best quality, but he has an epic tee shirt collection that tells me he still doesn’t take himself too seriously. Michael Rubin just continues to dominate whatever he touches, so spending some time with him would be super valuable. These are guys who make things go. Who knows, maybe we could meet at one of Dave’s restaurants and Francis Mallman can make a guest appearance as a chef.

As far as sports are concerned, I have crossed paths with a lot of athletes, and I never really got starstruck by any of them, perhaps because I always had access to them, but also because I saw them as my peers. I’m far more intrigued by what these people have to say and what they’ve experienced as opposed to how they dunk a basketball or hit a baseball. But I find myself watching The Shop on HBO a lot and would love to be in some of those discussions with athletes talking about real-world stuff.

This was very meaningful, thank you so much! We wish you continued success!

About The Interviewer: Growing up in Canada, Edward Sylvan was an unlikely candidate to make a mark on the high-powered film industry based in Hollywood. But as CEO of Sycamore Entertainment Group Inc, (SEGI) Sylvan is among a select group of less than ten Black executives who have founded, own and control a publicly traded company. Now, deeply involved in the movie business, he is providing opportunities for people of color.

In 2020, he was appointed president of the Monaco International Film Festival, and was encouraged to take the festival in a new digital direction.

Raised in Toronto, he attended York University where he studied Economics and Political Science, then went to work in finance on Bay Street, (the city’s equivalent of Wall Street). After years of handling equities trading, film tax credits, options trading and mergers and acquisitions for the film, mining and technology industries, in 2008 he decided to reorient his career fully towards the entertainment business.

With the aim of helping Los Angeles filmmakers of color who were struggling to understand how to raise capital, Sylvan wanted to provide them with ways to finance their creative endeavors.



Edward Sylvan CEO of Sycamore Entertainment Group
Authority Magazine

Edward Sylvan is the Founder and CEO of Sycamore Entertainment Group Inc. He is committed to telling stories that speak to equity, diversity, and inclusion.