Author: Steve Ainslie

I have been close with two ex-military guys. The first, a former Intelligence officer for the Navy, is my longtime good friend. The second, a former Special Forces leader, was my right-hand guy who helped me build & run a sales team. I’ve worked side-by-side with dozens of ex-military men throughout my career in technology…

In the Solo Podcast community and forum, there’s a fair amount of discussion about how “unfair” society is to single people (vs. married people). Frequently people post about married people receiving better insurance benefits, tax benefits, travel & lodging discounts and other preferential treatment. When I read or hear these complaints, I am tempted to…

It wasn’t until 9/11, when the planes took out the World Trade Center Towers, that I began to understand that New York City was a big deal in the US. Up until that point in my life, I never really thought much about New York. I was 33 years old and working out at the…

On the Pivot podcast today, Scott Galloway mentioned that he has “no attachment” to stuff. He said he was getting rid of extra clothes and noticed that his teenage son started showing up in “Brunello Cucinelli”. Scott said he enjoyed seeing his son wear his (Scott’s) old clothes. I am not familiar with Brunello Cucinelli….

I almost adopted a 3rd dog last week. I’ve said for awhile now that I couldn’t handle a 3rd dog unless I grew a 3rd arm. Managing my two bike/kid reactive dogs is already a handful. Wrangling them when I have contractors in my home or taking them to the vets together can be a…

Last month marked six years since my wife died and five years since I’ve worn my wedding ring. And yet, I still feel like I am married – especially when I am dreaming of her. Obviously, I know I am not married. Still, it feels weird to check the box for “SINGLE” on tax forms,…

Many of the books I read and podcasts I listen to have Millennials (and sometimes GenZs) as hosts, authors, and guests. A common trait I see in this group is a fear to try things, combined with a huge fear of failure. When I hear them talk about their upbringing, many had doting parents who…

As far back as I can remember, I’ve been someone who tries to make the best with what I’ve got. The story I like to tell myself is “I didn’t have a choice” so I was forced to accept the cards that were dealt to me and figure out how to live with them. But…

When I was on my road trip adventure/fiasco. I had this plan that I would “follow the weather”. In the hot spring and summer months, I’d camp out in forests and mountains where it was cooler. In the winter, I’d reverse direction and migrate to the warm deserts and possibly back to Florida. My plan…

I was listening to a podcast that discussed the Prisoner’s Dilemma and various strategies to maximize a player’s winnings. The prisoner’s dilemma is a situation in which two people can either cooperate for mutual benefit or betray the other person for individual gain. In simulations, the winning strategy was to cooperate on your first turn and then do…