Steve Strauss

Steve Strauss

How Getting Cut From His Own Father’s Baseball League Taught One Man the Value of Hard Work


Put yourself in this scenario: your dad is running tryouts for your town’s baseball league…


When the time comes to get picked for a team, your dad tells you that you didn’t make a team. But, he says, if you work hard enough, maybe next year there will be a spot for you.


That’s exactly what happened to Steve Strauss when he was 14 years old.  He could have let that ruin his self confidence or held a grudge against his father, but that’s not the kind of household that Steve grew up in.


Instead of taking this defeat personally, he vowed to get better and make the team next year.  This sort of upbringing fueled Steve to become a serial entrepreneur who is constantly challenging himself to be better every single day.


Chad and Steve have known each other for decades.  Chad was over Steve’s house constantly while they were growing up and they were even roommates in adulthood.  


Chad sat down with Steve for this episode of The Cannonball Mindset to talk about Steve’s family growing up, lessons learned along the way, and entrepreneurship.




Steve grew up in environment and family that truly valued hard work.  His family was large, so he had to discover new ways to get attention, especially from his father.  Doing things better than anyone else and with true excellence got his dad’s attention, so that is what he focused on.  


His home life helped support Steve as he moved forward into adulthood, and wired his programming from an early age.  His home provided a safe place that he could always return to where he never lacked food, shelter, love, and other basic human necessities.  This provided a stable foundation he was able to build his world upon as he grew up.


Lessons Learned


One of the first lessons Steve learned in hard work was when he tried out for as a 14 year old for his town’s local lead.  His dad was the one who ultimately decided who would end up on each team and who would be cut. That night as his dad was calling all of the other kids who had made a team, Steve realized that he was going to get cut.


His dad honestly told Steve that he wasn’t as good as the other kids, and that it would be an embarrassment if he made the team because everyone would know it was only because his dad allowed it to happen.  


So he asked Steve, “Do you want to be on the team and be embarrassed, or work hard and try out next year?  This instilled a value deep into Steve: there are no shortcuts and regardless of circumstances he had to work hard and hone his skills.  


You don’t get a awarded things in life because you show up. You actually have to be good and do the work.”  – Steve Strauss


Because of this life lesson, Steve always jokes with his friends and family today that there will never be participation trophies given out in his household.




Steve knew he was going to be an entrepreneur while he was in school at the University of Maryland.  While he was in school, he worked at a gas station where he had to arrive at 4:30 every morning. While he worked, he had deep conversations with a co-worker who would constantly encourage him to “do his own thing” and own his own business.  


When Steve was young, he became enamored with pins: swapping and trading pins, meeting other collectors, and discovering new pins.  This became a special hobby that he was able to treasure with his father.


Over the years, Steve has met people all over the world trading pins, and his father even made it their tradition to go on a vacation trading pins every year.  Steve was able to build that hobby into a business with his father and he still runs that company today.


Steve is the type of person that can’t do anything halfway;  He is 100% all into what he decides to pursue. This is a huge reason that he has become so successful and at 45 years old he owns seven companies.


Because he has such a great reputation as an entrepreneur, he often gets offers from people looking to partner with him, but he protects his time and energy by only getting involved with projects that are close to his heart.  He shys away from things that are not in his wheelhouse.


Steve believes that you can always move time around for what is important, and he’s no stranger to working hard. Over his career he’s sacrificed his weekends and put in countless hours of blood, sweat, and tears all in the name of making companies he believes in better.


“I was taught to do the right thing all the time, even when nobody’s watching.” – Steve Strauss


If there is one thing Steve is sure of it is this: you can’t outwork him.  Steve has had some fortunate opportunities in his life, but he has taken full advantage of every single one that was given to him by working as hard as he can.  


Steve believes that the one thing holding people back from taking advantage of every opportunity in front of them is fear.  At some point, you have to take a leap of faith, and get over your fear because that is where true greatness lies.


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