Saturday Ramblings

So I had a million different ideas for what I’d write about next before I pulled out my laptop and fumbled around for my username and password. After about 5 minutes of trying, I finally log in and now of course my mind is blank. 

I find myself now at almost 35 years old having spent nearly 13 years building my career to take a shot at building a billion dollar company. It’s insane how many hours of work I’ve had to put in to reach here. Honestly I often wonder if it was worth it even if I am successful. Last year my dog died and my girlfriend of 3+ years and I broke up. I didn’t appreciate how important both of them were to who I am and how I function. Looking back now one year later, I have to admit I didn’t realize how lucky I was. Not just to have sold my last company successfully but to have such a full life. 

It’s been tough realizing that I’m down at the bottom again and trying to build my way up and out. I wonder sometimes if I hadn’t created Skillz what would’ve happened instead. It’s unfortunately a futile exercise to imagine the world that never was. I can’t decide if those kinds of thoughts help me work harder to make Skillz happen or if they’re just negative drag which is something I worry about all the time these days. It’s like we’re trying to have enough momentum to make Skillz reach success and yet there are so many different people who are blocking rather than helping the company succeed. Some of these are people who want us to fail, to take the market space instead of us, whether big company competitors or new founded startups. Others of these are internal, some knowing and some unknowing employees, investors, customers. I often am not in a position to tell them exactly how much they’re hurting Skillz future and have to instead just take the abuse on behalf of the company. No one said being CEO was going to be easy but the saying it’s lonely at the top is incredibly true.

What I do to cope is a combination of exercise and meditation. I wish I had figured out the system I have now when I first started. I’d probably have been more successful in my earlier endeavors if I had. I’d probably also have more hair left 🙂

My system is something along the lines of waking up early, working out regularly at Barry’s boot camp, plenty of vitamins, trying to make sure I don’t have too much caffeine, trying to make sure I’m eating healthy. Sometimes I almost even sound like a grown up! I really believe in that for a daily routine and am trying also to work in more reading and more mediation as a daily habit. One of the most influential books I’ve read was Benjamin Franklin’s autobiography. He had really great ideas around personal habits and how to adopt behaviors that are ideal in our society. 

Since it’s Saturday, it seems like it would be a good day to practice some of this so I’m logging off and going to enjoy the sunshine.


It’s been almost 5 years since I last blogged. In all honesty I want to blame hackers (who broke in and corrupted my old site), too many hours working on my company, or maybe even just life getting in the way. In reality I can only blame myself for not making this a priority sooner. So with that light preamble, it’s time to dust off the writing skills and reboot 🙂