Leaders of Tomorrow: James Santore, Three Two Strategies
Welcome to my “Leaders of Tomorrow” Interview Series, where I interview those who have made, and are making an impact on the world of tech as we know it. I ask them to share their stories and explain what it took for them to get to where they are today. My hopes are that this can inspire and educate aspiring entrepreneurs in their journey.
This interview is with James Santore, Founder of Three Two Strategies
About James and Three Two Strategies:
James is Philly born and raised (South Jersey if you want to be exact!) and received a degree in Finance from La Salle University while playing four-years of Baseball for the Explorers.
After starting his career in corporate finance, James made the move to the sports and venture capital world while serving as the Chief of Staff, and later Director of Marketing, at SeventySix Capital.
After 2+ years at SeventySix, and a stint in Chicago at SeventySix portfolio company Fubo Gaming (formerly known as Vigtory), James started Three Two Strategies, a marketing services and consulting firm focused on helping companies grow their brands.
Three Two Strategies is the full-service marketing and strategic consulting firm that helps venture funds, startups, athletes, influencers, and small businesses grow, improve, or even start their brands.
We bring your brand to life through creative, efficient, and effective practices guaranteed to impact your bottom line.
What motivated you to do what you do now?
Freedom; I hated the notion that I had to tie myself down to a single job in a specific industry and realized that if I was truly going to love what I do AND be really good at it, I had to work in a way that was more suitable for me than your typical 9–5.
Everyone works differently and I want to instill a culture at Three Two Strategies that is conducive to that. I personally enjoy being able to do other things throughout the day (workout, skateboard, shop, etc) to make sure I give my mind a chance to rest in between projects and allow initial ideas to marinate at the same time.
Building a culture that allows for flexibility and creativity will, in my mind, develop a better work/life balance and thus improve the quality of work.
What tip would you give a younger you?
Have confidence.
I grew up struggling (and still do struggle) with having confidence in myself in almost every aspect of my life. But it wasn’t until after my time playing baseball at La Salle that I realized that my confidence didn’t need to stem from success on a field, but can also derive from a place of knowing that I was putting my best energy into everything I did on a consistent basis.
The more I started realizing that, the more fun I started having in my life. Worry less about what you can’t do, and start worrying more about how to be really damn good at the things you can do.
When starting a company, what is the most important step to ensure you have the best chance to succeed?
Be willing to listen. I am very aware that I am going to make a lot of mistakes along the way (I already have!), but if I’m not willing to listen to those that I trust as well as myself, then those same mistakes will continue to happen.
Instead of viewing mistakes as a negative thing, look at them as an opportunity to learn and get better for the next time. Think “I’m doing a hell of a lot of learning lately!” instead of “I’ve been making a whole lot of mistakes lately!” and you’ll be willing to take more calculated risks that will expedite your learning and growth potential.
If you could see the future, where do you see the gaming market in 10 years?
Way bigger financially than we can even begin to imagine, but much smaller from an opportunity perspective for young companies to disrupt.
I personally believe that the next 3–5 years will be chock full of acquisitions and consolidations amongst the current players within the industry, and that is due to a massive influx of new operators and investment both before, during and after the peak of COVID-19.
These operators are still struggling to find profit (and customers!) as a result of having to compete with astronomical marketing budgets and risky promos. In my opinion, this will lead to a “great consolidation” where we will see more deals akin to Barstool’s acquisition of TheScore.
All-in-all, this will probably create a better experience for the consumer and help stabilize an extremely volatile industry. By 2032, I expect 49 states (Utah, smh) to have legalized sports betting and a much simpler, safer, and sustainable betting ecosystem to pair with the millions of new consumers that will be added into the mix.
Do you think college is needed to succeed? And why?
It all depends on the person.
For me, college was less about what I learned in the classroom and more about maturing as a person. Most of my growth from a business perspective came via internships and real world experiences, but none of that experience mattered without a true sense of understanding myself and how I wanted to play my part in making an impact.
My ability to develop my understanding of myself and those around me happened during my time at La Salle University, but I would attribute that mostly to the great people and experiences I had during that time than college itself.
With that being said, if a person is looking to find understanding and maturity and is able to afford the cost of a college education, it is well worth the price of admission. But there are plenty of alternatives to finding that special circle of people that are much more cost-effective and practical for those that do not want to make the investment in college.
What tip would you give a young entrepreneur trying to raise capital?
You HAVE to believe in what you are raising capital for.
It sounds super simple but if every single person on that management team isn’t 10000% on board with what you are building, and it shows while pitching, it shows in a much bigger way than you could imagine.
Chemistry is the second most important thing a startup can have (capital being number one), and besides the occasional right-place, right-time acquisition, the majority of companies that do have long-term success have the best cultures and people.
Knowing when to compromise to make sure there is cohesion in the vision of a startup is vital to success. So do not be afraid to put that ego aside as long as there is logic and reasoning behind the decisions made. If those two things do not exist, allow your confidence to explain the logic and reasoning to make your argument.
Be transparent in your beliefs. It will help accelerate, and sustain, growth.
What are your thoughts on web3 and different industries trying to add such capabilities to their business models?
I am a big believer in the “Democratization of assets” and I love that web3 is putting that into action.
With that being said, I hate that social media and mainstream media only display the negatives of an industry that is growing much more rapidly than other similar industries before it.
As with anything new, there will be struggles and mistakes that happen. But the most important thing that can happen when those issues arise is having a quality approach to resolving them so they happen 1) less and 2) never in the future.
And I think that’s why web3 will succeed. The communal aspect of Web3 allows for anything that the people value to exist. So when tech, regulatory, safety, etc issues frequently arise in the beginning stages of this burgeoning tech-driven future, we have to look and see how the communities and developers come together to ensure that issues are actively addressed and resolved.
If you had your life savings on one future bet to cash, what would it be?
Sixers winning a championship by the year 2027. There is no way I have been through this much pain to not have a party on Broad Street in the Summer with Joel Embiid still in a Sixers uniform.
Who is someone you have looked up to or were inspired by?
My Dad.
I grew up seeing my Dad be a bad-ass businessman and always being mesmerized by the nuances of his life. From travel, his various offices, the different people and industries he worked in, and all of the craziness in between, my Dad exhibited something that I think is more important than anything else in business and life in general: being compassionate towards every single other person he came in contact with.
And that’s what inspires me the most. My Dad has worked his ass off his whole life and has made sure to do that while helping others, and I want to make sure I continue to do that. Because success is much less about money and physical things and much more about the people you are blessed to surround yourself with. And the way he has treated people has led to him having some pretty awesome people around him.