As an executive, it can be quite lonely at the top, and so having the opportunity to surround myself with a few other folks, especially of different walks of life as well, in different industries was appealing because I believe in the value  of diverse thought and experience and some of the opportunities for learning that that can present. So really, that was the main driver, kind of continuous ability to learn from Sara and learn from others and sharpen the pencil as an executive.

I’m just sad I didn’t get to benefit from it as much as I could have due to a health issue!

There’s a lot of shared experiences with respect to the challenges of being a leader, whether that’s from financing to dealing with other founders or other members of the leadership group that may be challenging to deal with, and the various headwinds that exist that are out there and seemingly never go away. I think there’s a lot of interesting thought and just like a good feedback loop from the group that the Mastermind created, which is cool. 

One of the big things that I realised is that just pulling people together because they’re talented isn’t the right move. There has to be emotional connectivity there that I think is hard to appreciate, but something you shouldn’t discount. Culture is everything.

After bringing SIS to its current point and successive years of 40% YoY revenue growth, and realising that there was a divergence of vision with the Board; I decided it was the right time to move on to my next adventure.

I realised that I like two aspects of business that I really find myself drawn to. Coming from a sports background, that is the team set up, which I think Draftkings, that I’m returning to, has in spades. They have a high performance culture and I was really drawn to that. That competitive dynamic that exists in the ecosystem where there’s always that group that you’re against. So that helps create that camaraderie and that sort of team dynamic because there’s a shared enemy. I believe in the competitive spirit of people in a business. And I think that’s a really big draw for me.

It’s amazing how my perspective has changed by virtue of leaving Draftkings, rolling the dice, taking on a CEO’ship at SIS. I think I have more shared experiences with the founder team now than I would have, had I not actually departed Draftkings. And so I think it set myself up sort of better going in and I have all this learning in my back pocket.

I would recommend the mastermind!  If you’re new to the role or if you’re experienced in the role. Either way, I think it’s super valuable. If you are in a leadership position and you don’t have a great support network of other people around you who are in similar dynamics. Like for myself, with a company solely remote, I don’t go into an office. So, I don’t get a lot of exposure to other founders, especially outside of my industry. 

Watch the video testimonial.