On the flight back from the Future Proof Festival last week, I couldn’t help but think about the amount of fun, vision, and hustle I had just witnessed and taken part in. It’s an electric event with access to just about anyone in my industry and where one’s dreams can become realized. My mind then went to two people I’ve read extensively about, that share/shared the same energy being released. Both of these people seemingly figured out how to prolifically and purposely live/lived four lifetimes in one.

• Theordore Roosevelt
• Jessie Itzler

I’m not sure how much sleep they require/required, but guessing less than the ‘normal’ person. Natural energy level? Off the charts. What else made/makes them unique? Curiosity, creative thinking, and then the act of DOING.

For Teddy, he a was prolific author and doer of all things that spiked his curiosity. He left his pampered, educated life in NYC for the Wild West and once punched-out a cowboy who called him “four eyes.” He came back, was appointed to several irrelevant government jobs to keep him busy and out of the way (he was an inconvenient agent of change), only to make them relevant and high profile. He left one of those positions, Assistant Secretary of the Navy, to assemble his Rough Riders and led a charge up the San Juan Hill, dodging bullets, unscathed to victory at the top. He tried to turn down his Vice President nomination (that used to be political suicide), but after President William McKinley became ill and died months into his presidency, this ‘Man of Destiny’ become the youngest president ever.  He was fluent in three languages and as president, would often communicate with ambassadors in their native language. He ‘settled’ a 50+ year government stand-off and pushed through the Panama Canal and cementing the US economy as a #1 exporter of goods. He once held the Guiness World Book of Records for most handshakes in a day, some 6,000 (every New Years Day he would greet any visitors at the White House if they were not drunken, dressed appropriately, and women wouldn’t hit on him). There’s so much more, but you get the point.

Jessie on the other hand is a similar burst of curious-creativity energy and serial entrepreneur. Also, a native of NYC, he became a white rapper and then pivoted to writing pro-sport team’s jingles (Knicks theme song). Upon selling his first company and riding on a private jet for the first, he approaches Net Jets about creating a fractional-use jet card company, Marquis Jet, and after a wildly successful 10-year run, sells it to Warren Buffett. Not allowing himself in the trappings of success and boredom, he pivots to health and ultramarathons (100+ miles). Researching hydration and electrolytes, he determines coconut water to be superior to Gatorade- then finds Zico Coconut Water and subsequently gets it sold to Coca-Cola. Still racing and pushing his limits, invites an unknown former-Navy Seal named David Goggins (now famous for saying ‘Stay Hard!’) to live with him and his family for a month. The result? His first NY Times #1 Bestseller “Living with a Seal”, which leads to his second book about silence, “Living with the Monks”. In between all this, he marries his wife, Sara Blakely, billionaire founder of Spanx, has four children, and becomes owners of the Atlanta Hawks. He’s not done yet.

I say all this because both men found ways to achieving their dreams and goals. Sometimes it happened because of fate or what some people call luck, but most was from following their gut, staying curious, and then creatively finding solutions to problems. At its most basic definition, this is what a financial planner does for you. We take your goals, we your numbers, and we tailor a personalized success plan for you. This plan often changes with life, so we forge a personal relationship with you and update it often… if you participate, because it’s a two-way street. Don’t have a planner? I know a guy and it’s worth your weight in gold.

Want a quick inside story of how to do just this? ‘Got Muffins?’ is a story in my upcoming book, “Debt Row 2 Cash Flow”, about how Jessie was able to jump start his fledgling, fractional jet card business. Needing high net worth, very-guarded clientele, to make it a success, he had to find where they were at and then how to get a seat in front of them.

Around this time, the tech industry was awash in cash and the now legendary TED talks had just launched and with it, a crowd of forward-thinking movers and shakers with deep pockets. Bingo! He knew the niche for his brand and had discovered an event with direct access to them, however he had no lanyard and subsequently no inside access. His brain fluidly moving to how to secure outside access to these HNW potential clients, he observed their morning routines. Across from the conference center was a coffee shop that every morning had a line out the door of HNW, TED-talk attendees grabbing a great cup of joe and- a muffin. The next morning, Jesse goes back, and making sure he was first in line, grabs a coffee and buys all the muffins. He just cornered the market. As the usual crowd lined-up to get their coffee, they were greeted with a “sold-out” response about muffins “because that guy sitting over” had bought them all. Guess what happened next? A recently minted millionaire many times over comes up to Jesse, and Jesse asks him would he like a muffin? “Yeah, I was trying to buy one. What do you do?” Jesse says, “I own a private jet company.” To which this guy responds, “Really? I’m in the market for one.” SALE.

To be clear, Jesse didn’t own any actual jets. His genius was going to Net Jets and using their unused planes sitting on the tarmac into an Uber-like service and creating new profits for both his company and Net Jets. In business, you charge more money by selling in smaller quantities and keeping your team at an efficient level of productivity. Jesse nailed both.

I love this story because it shows the outside the box thinking that an entrepreneur or any leader must be successful in certain moments. I’m sure Teddy had similar behind the scenes stories from every win he achieved. It also highlights the value of having a carefully thought out and executed plan- one that a good financial advisor and client relationship can achieve. I just used those same tools to come home from Future Proof with some big wins. I’ll share more in due time.

What are you working towards? Do you have anyone helping you out or at the very least holding you accountable? If you don’t know where to start on your goals or need accountability, consider a CERTIFIED FINANCIAL PLANNER® to help you get started and see you through.  

Got muffins? We’ll help you get some.