Name: Indiana Gregg. Age 48 . Education: Bachelor of Science, Sports Medicine & Athletic Training, PT. MBA Born: Terre Haute, Indiana. 

Job role: Chief Operating Officer Sportside. 

Career: Tech pioneer, brand designer, singer-songwriter.  Founder of

Hi Indy. So how did you get involved in the Sportside journey?

I think I was primarily drawn in by Xan’s enthusiasm. I have been working with start-ups as a consultant and executive coach since 2009. Hermione Way, our CMO put me in touch with Xan and his passion about helping people connect through sport was infectious. 

With every start-up, there are a million and one things to do and not enough time to get them done. I’m an executer and saw how and where I could help through my network of contacts, experience and business acumen. Plus, I’ve always had an affinity with sports. I was an NDA all- american athlete in dance and a US national dance champion at University level. I have an empathetic understanding for what it takes to win and have applied that champion ‘drive’  to every aspect of my creative and business life. 

And you have been on a journey yourself. You started off life as a five-year-old musician in Terre Haute and are now a tech innovator. Is there a connection?

I think music and mathematics will always have a strong connection. After all, music is just the study of numbers in time. Learning music from an early age requires mental mathematics whether a kid is aware of it or not. So, it’s not uncommon for a musician to have a strong interest in math and physics and therefore, it makes sense to me. I’m a creative person and spend every waking hour of my life in a ‘creative’ zone. Technology requires an intense amount of both creativity and mathematical skill. So, to me, the connection is obvious. 

How has Sport influenced your life and career?

As a kid I was involved in competitive Dance, and although a lot of people don’t consider dance a sport, it definitely is at the US national competitive level. I was an NDA national champion at University and I believe winning the US national championship at the university level  taught me a lot about hard work, dedication, and team building..  

You hit the headlines as a singer and songwriter. What’s been your musical highlight?

The days that I spent in Dublin with the Irish film orchestra and hearing them perform my compositions was the most heart-melting moment. As a songwriter, that’s kind of a big one.  Other than that, I feel as though I write in order to help people see their lives from a different perspective.

What gets you out of bed in the morning? 

Commitment, coffee and messages from the universe. But reallly lots of coffee.  Mornings are my creative time. Every morning I wake up and generally Xan and I have a call about the business and something magical happens every day that literally helps move the ball forward. Sportside is an epic ‘team’. Our exec team is on fire and everybody loves each other! Not all start ups are alike. This one is a unicorn.

Some words of advice for budding tech entrepreneurs?

1,Don’t put the cart in front of the horse. Developing a great product requires product/market fit and a number of iterations until you get it right. Test, test and test again.

2. Expect to fail and when it happens, see the opportunities that arise. They are magical. 

 No technology should ever be stagnant.

Sportside aside, what is your career highlight to date?

Watching people and ideas grow and come to life more than anything else. Being a part of amazing teams and helping people achieve their dreams.   

Who inspires you from a business point of view?

Hmm. There are many. I love Arianna Huffington. Her perspective on life and business falls right into my ethose. My favorite quote from her is:  “Fearlessness is like a muscle. I know from my own life that the more I exercise it the more natural it becomes to not let my fears run me.”  

For me, there is something about being fearless that gives me an unexplainable sense of calm. And that sense of calm, I believe, helps me when I’m communicating with teams on both an operational level and a level of understanding people in a profound way. It’s key to motivating teams.  At Sportside, we know what the end goals are and we’re on a mission with a purpose in this movement. 

And your sporting inspiration?

I grew up in Terre Haute watching every ISU basketball game from the floor seats at Hulman Center. Larry Bird was our star player in the late seventies, early eighties. I got to meet him several times as a kid and he’s gotta be the most inspirational athlete in the history of basketball. It’s dedication and shooting hoops every day for hours that got him his spot in the sports hall of fame and I think a lot of my pride being a Hoosier stems from him as a role model. My dad would talk about Larry Bird constantly and we had tons of Celtic memoribillian in our home. My dad would say, “Honey, don’t give up. Be like Larry”. And it’s true. Only the quitters lose.  

How do you think Sportside can change the world?

Sportside is exactly type of company I love to work with because it’s socially conscious and uses technology to better peoples’ lives. Let’s face it, if you’re meeting people to play sports with, you’re not sitting on your arse scrolling through feeds. It’s a win/win. Using technology to help get people outside of their heads and into a healthy social environment is precisely what the world needs right now. It’s fundamental to both physical and mental health as well as the relationship upside that comes along with it. It can help people in every level of their lives, professionally, mentally, socially, vocationally and beyond. This is the kind of dream that must be executed.  

Three guests at your perfect dinner party, living or dead?

Marie Curie, Henry David Thoreau, Florence Nightingale –  I can’t believe you’re only letting me choose three. I’ll go with the dead ones then, because the live one’s I may actually end up having dinner with some day! 

Guilty pleasure?

Whisky, for all the wrong reasons and therefore rarely.  

What’s your next big goal?

You mean, after helping to make Sportside an inrresistible global phenomenon? Well, I’m currently writing a book called ‘The ABC’s of Purpose’ which will be out in March 2020. Other than that, my biggest goal is to help other tech future start-ups make it happen!