About Me

Name: Jesse Henry

Birth Place: Boston, Massachusettes

Birth Date: October 6th

Height: 6'5"

Weight: 225 pounds

Eyes: Hazel

Hair: Dirty Blonde

Occupation: Entrepreneur & Investor

College: Florida State University

Major: Entrepreneurship & Sales

Favorite Sports: Volleyball, Hockey, & Weightlifting

Favorite Animals: Monkey's, Giraffes, & Sea Otters

Favorite Emotions: Gratitude & Love

Favorite Fruit: Strawberries

Favorite Fast Food: Chipotle

Current Home Base: Phoenix, Arizona

Number of Countries Traveled: 20+

Jesse Henry 4

How it All Started

I’ve been told that we spend our lives as adults trying to solve the same problems we had as kids. This concept has always fascinated me. It helps us understand how others, and ourselves, see the world and make decisions.

I’m not sure if scientists would agree that we spend our lives solving these same problems, but I have found this concept relevant in my own life.

Jesse Henry Childhood

Here were the 2 things I was forced to overcome during my childhood:

I was born near Boston, Mass – but ended up moving 4 times by the time I was on 4 years old. I spent 20 years in Florida, but have spent much of my 20's moving around. I was always (relatively) comfortable with the change, but, accepting this reality makes me realize that change will be a CONSTANT in my life – for the next 80+ years. That’s not going to CHANGE.

As an adolescent, all the way up through my teenage years, I had a stutter. I had trouble pronouncing words that started with…. about half the alphabet. Saying my name was the hardest.

If you watched my TEDx Talk – you were able to get a small slice of how life used to be. It was UNCOMFORTABLE.

I spent most of my childhood as a tall, skinny, awkward kid who had a stutter. I’d like to think we all had a rough patch at one point or another.

I mention this during the first part of my TEDx Talk to show people how uncomfortable it was for me to communicate on a daily basis.

It served as a cornerstone obstacle in my life that helped develop me into the person I am today.

I’m telling you this because I went from a kid with a stutter – to a business leader who speaks with power, conviction, and congruency. When people tell me that I’m a “natural” up on stage, they are all sadly mistaken.

Most people have a fear of public speaking – but this fear gets amplified with a stammer.

Overcoming an obstacle like this is a process.

We’re talking about a decade + of stage acting and speech therapy.

These are the tools I had as a child to enhance my communication skills.

This obstacle throughout childhood has put me on the lifelong journey to master communication in its many forms.

Jesse Henry in the 90's
Jesse Henry in Highschool

High School

In high school I was very involved in sports. I participated in 2 sports a season: hockey and cross country in the fall, then volleyball and track in the spring. Needless to say – I stayed VERY busy.

At the time, cross country was the hardest I had pushed myself both mentally and physically. During peak season, I was running 90 miles + a week – and the results were showing. I realized – you only get out of life what you put into it. Cheating the workout was only cheating myself.

Because I enrolled for school late – I was locked out of the typical freshman electives. This meant I was stuck in a business class. I was forced to join a club called DECA, and this was my first taste of what business was really like.

The organization had different categories with both written tests and role plays. I ended up going to the state competition for all 4 years – and qualified for the international competition twice. In my junior year – my partner and I placed in the top 20 internationally for the “Business Law and Ethics” category. It was the first stepping stone in my professional life.

The high school that helped me become the man I am today is none other than Marjory Stoneman Douglas. On February 14th, 2018 – someone murdered 17 Stoneman Douglas students and staff. The event that has destroyed my hometown created a national movement. Parkland Florida will be the epicenter of a shift in our political structure. That became partially evident in these past 2018 midterm elections.

I wrote the acknowledgment section of my book about Stoneman Douglas. You can find it HERE


College was an incredible experience. I had the opportunity to start 2 companies AND 2 entrepreneurial organizations while on campus. A koozie company, and a video production company helped me apply the tactics I was learning in my entrepreneurship and sales classes. But, getting involved in the Tallahassee entrepreneurial ecosystem was what really made the college experience worth it (for me).

I started the Florida State CEO (Collegiate Entrepreneurs’ Organization) chapter. This steamrolled into other projects, both on campus and with the organization nationally. During my senior year, a good friend and I created the Office of Entrepreneurship and Innovation as a bureau of student government. This allowed us to lobby for appropriations going toward entrepreneurial initiatives on campus.

I really began to understand the interconnectedness of business and politics in a way that opened my mind to endless opportunity.

Jesse Henry TED Talk
Jesse Henry Speaking at Investable Bootcamp

Launching a Career

After college, I had NO CLUE what to do. I had preached entrepreneurship as a student – but knew I had to learn the ropes before taking a jump. This was a misguided assumption, but I’m grateful for the experience it lead to.

Shortly before I graduated from college, I had the opportunity to do my first TEDx Talk. That speech was what afforded me the opportunity to become a peak performance strategist for Tony Robbins.

It was an incredible experience that I quickly decided wasn’t for me (long term). I was running the same workshop over and over, and as you now know, the lack of change (or growth) was frustrating.

But, when I left the organization, I looked back at my notes and realized that 2 problems persisted in all of my clients.

  1. Access to capital
  2. Millennials (and relationships as a whole)

So I set out to solve those 2 problems.

Traveling and Investing

During 2017 and 2018, I worked as Chief of Staff at Intersection Capital and Pitch Anything, a small investment bank in southern California. This job brought me face to face with business operations, capital raising, pitch building, and deal flow management. It was the perfect experience to hone my financial acumen and understanding of the capital markets, and the value chain that surrounds it. I’m grateful to Oren Klaff - he was an incredible boss, manager, partner, role model, and mentor during the experience.

I have now moved out Scottsdale Arizona to work on a few investments. I’m excited to share the path with you as everything begins to materialize. 

Traveling has had a massive impact on my perspective, and how I see the world. Over the year's, I've been blessed to travel to.

  • Costa Rica
  • Canada
  • Jamaica
  • Israel
  • Thailand
  • Singapore
  • and 14 Countries within Europe

What people want, vs what they need - are completely different. In America, we live a life behind a screen with airconditioning and clean water. Most of us have no idea what it means to truly struggle.

My travels have propelled me toward activist investing. Infrastructure, education, energy, agriculture - these are the things that society needs.

While many within my generation will spend their lives behind a computer screen, I aspire to travel the world and help governments and leaders build a foundation for their people. Click HERE to find out more about my investing activities.

Jesse Henry in thailand

If you're interested in learning more about the millennial perspective...

This book will tell you everything you need to know about how to sell, manage, empathize, and communicate in a multi-generational workforce. If you can understand how millennials listen, think, and act, you can survive in the 21st-century workplace.

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