My personal challenges help me become a better human...
Things are only obstacles if you see them as obstacles. If you shift your perspective and see them as challenges, then they are something you can overcome.
I hope I inspire people.
Embracing challenges through the approach of optimism, discipline, and humility has been my guiding light from a very young age. The inspiring lessons I’ve learned throughout my personal and professional life are the result of overcoming significant obstacles including nine blood transfusions, asthma, and dyslexia. My hope is to share my story as a guiding light for others as one of the most recognizable examples of how fearless optimism and steadfast determination will guide you toward success, even in the face of adversity, a topic I covered in a TEDx talk in 2020.
I currently live in San Diego with my wife and two younger children while my eldest daughter forges her own entrepreneurial path in Denver, CO. In my free time, I enjoy living life to its fullest. Whether it’s biking along the entire coast of California, wrestling a crocodile, bullfighting, running a marathon, or swimming with sharks, I’m always seeking new challenges to show those like me that it is more than possible to realize all of the dreams that we previously thought impossible.
1986 - 2022
2022 CHALLENGE: 10K OPEN WATER SWIM
I officially completed my 2022 10K Open Water Swim Challenge on September 17th, 2022! Proceeds were donated to the Autism Society of San Diego and the San Diego Blood Bank.
This was the most difficult challenge I have completed to date, and a true testament to my belief that drive, determination, and perseverance are in my blood. Watch my journey here.
2021 CHALLENGE: BASE JUMPING
Because I've spent the last few years working on authoring my book, making media appearances, and developing the BOSS Capital Partners investments syndicate as well as BOSS Startup Science, I have been putting off a commitment to jumping back into “real work.”
Overcoming the fear of this BASE jump symbolized my getting back into the game, stepping off the ledge, and putting my trust into the next chapter of my professional life. I am going to dig in now; what a rush of powerful emotions. Look out entrepreneurs and investors, Greg is back!
2020 CHALLENGE: TEDX TALK
Let's be real, who isn't a huge fan of TED? It has always been my passion to inspire others by sharing my personal story, after nearly two years of hard work and persistence, I had the amazing opportunity to do just that. What an experience!
I felt this was an important time with Covid creating some extremely difficult times for many people. The experience was incredibly rewarding, the people involved were honestly some of the most genuine, kind, thoughtful and smart people I have ever met. It was the first time TED had gone from live events to a studio due to Covid, however I felt it was powerful and I hope my talk is helpful for those who engage. What an honor…What an achievement. Thank you, TED!
2019 CHALLENGE: GIVE ONE GALLON OF BLOOD IN ONE YEAR
I was born with an RH incompatibility. In 1968, this incompatibility in RH-/+ blood types between mother and fetus was misunderstood and research was scarce. I received and survived 9 blood transfusions during my treatment - breaking a record at that time. There were times that I stopped breathing, moments when my heart stopped, and at one point I was declared dead - but I survived because of those blood transfusions. My brother, who suffered from the same RH incompatibility, did not. My mother always told me, “you are here for a reason.” She told me that it was my responsibility to give back. The angels that donated blood literally saved my life - a gift that is not lost on me. I made a goal last year to donate one gallon of blood. This year, my goal is two. I will never know the people that saved me with their gift of life, but I will honor them by paying it forward.
To acknowledge Greg's ongoing contribution, he was featured in the Team Survivor section of the San Diego Blood Bank newsletter in April, 2020.
2019 CHALLENGE: 525 MILE BIKE RIDE ALONG THE CALIFORNIA COAST
I always wanted to ride from SF to LA on the Pacific Coast Highway. So, I decided to do it. On the first day of training I was only able to do 5 miles. 6 months later, I was riding between 50 and 80 miles per day. For the race, I had to ride 6 hours per day, 7 days in a row. This challenge made me dig deep at times, and I would see riders older, heavier, and some with disabilities. This brought me a sense of humility and inspiration that I reflect on to this day.
2018 CHALLENGE: DEADLIFT 500LBS, 5 TIMES, AT 50
Growing up I took a pretty bad emotional and physical beating on a daily basis because I was bullied for my learning disabilities and eccentricities. At 13, I saw a picture of Arnold Schwarzenegger and thought, "Maybe I can prevent this," so I started lifting weights.
By the time I was 16 I was competing in bodybuilding contests, but in my late 20s I had an accident that put a stop to heavy lifting. At 49 I decided I would beat my record by lifting 500 pounds, 5 times before I was fifty. I started training in Feb and by June I pulled it off.
2018 CHALLENGE: MEET PRESIDENT BARACK OBAMA
In 2018 I had immersed myself in politics and worked as the chairman for a congressional candidate. This exposed me to the political world and provided myself and my wife the opportunity to meet President Barack Obama. No matter what side of the aisle you're on, meeting the country's first black president is a special moment since it meant we were taking a big step forward as a country. It was a truly speechless, heart-stopping experience. Barack is a genuine and kind person who took the time to allow my wife and I to catch our breaths and actually talk with him.
2017 CHALLENGE: RUNNING THE SAN DIEGO MARATHON
I have asthma and as a child I was not allowed to do physical education or play sports in school. I always felt left out, like that strange kid that “got out of PE.” As a young adult I decided to lift weights and this made running difficult because of my bulky build. Like every physical challenge, I started training at the start of the year. I could not even run 1 mile when I started but eventually I was running 10 miles on a regular basis and 16-18 miles on harder days. At 5AM in June I put on my shoes and, with my coach at my side, joined hundreds of others like me going after the impossible, with no explanation as to why. It took me just over 7 hours. I never stopped. When I crossed the finish line I was one of the last, but to me just doing it meant I won MY race. I hope this inspires you to do something impossible; the feeling of empowerment is unmatched.
2016 CHALLENGE: TREKKING ACROSS THE SAHARA DESERT
I have always wanted to do a long distance journey in the Sahara Desert and in 2016 I made the goal come to life. I must say, riding a camel through the Sahara Desert is one of the most unforgettable and uncomfortable experiences I have had. The animal was not pleased with having not one but two people on its back and kept reaching around to take a nip… so I rode in the back LOL. The bumpy hard ride left quite a bruise that you have to sit on the next day.. that was the roughest part. The people were absolutely humble, kind and attentive. The scenery was like nothing I've ever seen. You would find red sand gliding over the surface of the sand dunes creating delusions of dancing red mountains. A new type of wildlife and backcountry I had never seen before or experienced was worth the bruising.
2015 CHALLENGE: LOSE 30 POUNDS IN 30 DAYS
I had put on quite a bit of weight, not just because of eating crap food which I did, but mostly due to travel, and also working so many hours I had no time for anything else. I had decided that I would lose 30 pounds and to make it happen with work and travel I would have to do it 30 days. It was so effective I actually ended up losing 45 pounds. Everyone asks, “how did you do it”, well, after talking with a doctor I dropped my caloric intake to 800 calories…If you have never done this it's a serious challenge! Next I introduced HCG which prevents your body from eating muscle as you are not eating enough calories. The first week you honestly feel like you're going to die, then your body starts to eat fat and it gets easier, NOT easy, but easier.
2014 CHALLENGE: LEARN HOW TO BE A BULLFIGHTER
When I was in grade school I would work on a ranch before and after school. Twice a day I would change 40 foot irrigation pipes over about 25 acres and afterward would walk into the bull pen to feed T-Bone (that’s what I named this huge bull). I would have just enough time to run across the pen, and every time T-Bone would chase me and each time, I would leap up over the fence right before he got me. Thinking about this, I decided to try bullfighting. I took a class and immersed myself into this very hidden and prideful world. You start with a small bull and work your way up. Don't judge by size; when a bull is running at you horns first and you hear the pounding of the hooves it's pretty intimidating. I found those whom do this respect the animal and watching after you learn allows you to see the art of it.
2013 CHALLENGE: LOSE FEAR OF THE OCEAN AND SWIM WITH A GREAT WHITE SHARK
I have always had an irrational fear of deep ocean water. I could not even go past my waist. I tried surfing but the fear made me stay completely on the board; I would not even let a toe slip into the water. Stand-up paddle-boarding was a disaster for me as well because I was afraid to fall in. I decided (as I do) to face the fear head on! Each year in Farallon Islands near San Francisco the great white sharks come to prey on the seals during their breeding season, I had been on the waiting list for a while and my name came up! It was 6:11AM on November 2013 when we left. After a long journey with awful sea sickness we arrived. Straight away, they had the cage ready for a dip and I went first! The water was cold as hell and that was a surprise. It felt like I was floating in space and the deep water without much visibility was already pushing my limits. I looked down and saw a small white dot then, looked up at the surface seals. When I went to look back down a huge great white came out of nowhere and straight up past the cage displacing the water and moving the cage. I just about shit myself! I thought this would help as I would see for myself the sharks are only interested in seals and thats true; they had no interest in me. But for this challenge, let's just say my goal to lose the fear did not work!
2012 CHALLENGE: DRIVE AN INDY RACE CAR
Okay, so who has not dreamed of driving one of these things. In 2012 I created an opportunity to do so. What a rush! When you first get in this beast it's so small I almost didn't fit. Once I was able to squeeze in, I was almost laying down, shoulders smashed and arms forward. I could barely move. The steering wheel is small and the the car pivots at the slightest turn. The engine is right behind your head and even with the helmet the sound is intense. You're probably 3 inches from the ground so as you pick up speed the combination of the sound, laying down right next to the road, and the wall passing by like an unfocused video is, well, a rush!
2012 CHALLENGE: GO 70 MPH IN A BOBSLED
In March 2012 my family was on a road trip driving from Maine to Key West to explore the east coast. As usual, I get online and find whatever I can do. The 1980 Winter Olympics Center in Adirondack Park, Lake Placid offers the opportunity to experience a real Olympic bobsled course. I mean, who could turn that down! The bobsled gets to over 70 miles an hour in seconds. The turns feel like what I would imagine a fighter jet to be like but you're sitting in this thing shaped like a bathtub. You cannot see the turns coming and without warning you flip left to right and vice versa. The turns almost feel as if your going to go upside-down. The ride goes by in a flash and when you climb out it takes a second to absorb what you just did. This was awesome!
2011 CHALLENGE: WRESTLE A CROCADILE
I have always been afraid of crocks, I don’t live near them and have no experience with them but anytime I am near water where they live the thought of being snapped and pulled to the depths is terrifying. Yes I know everyone feels that way! So on a trip to Orlando Florida in April 2012, after hours of phone calls and online research and mostly hearing “are you crazy? um no we don’t do that," I found a place that I could take a class and have an “animal interaction” I call crock wrestling. You start with the small guys and work your way up and by the end of the day you earn your way to the 9 foot crocks. The guy I had was named sawtooth. I was on a man made island surrounded by a moat filled with crocks. While I was working with Sawtooth, the guide was keeping the others from attacking with a special rake tool. In the process I actually felt bad for the animal, after all this is a dinosaur and they deserve our respect. This powerful animal was able to throw me around easily with its tail! They can bite down with up-to 3,700 pounds per square inch (psi) of pressure. My guide said, "listen, if he gets you it would be like a semi truck driving over your arm." This was scary even for me. However, the most difficult part wasn't jumping on his legs and grasping his jaws faster than he can flip and bite, It was getting away without it flipping around and taking off my leg. This is not for the average thrill seeker.
2011 CHALLENGE: SWIM WITH A SEAL
In 2012 I had the opportunity to swim with a seal. This was absolutely amazing, not scary at all! These creatures are instinctively kind and not as skittish as I expected. What stuck with me is the incredible similarities they have with dogs; it's like swimming with a Labrador. She even at times would look back to make sure I was ok as if she could sense my fear of water.
2006 CHALLENGE: BECOME A FATHER FOR THE THIRD TIME
2006 was dedicated to supporting my best friend and partner (wife) during the pregnancy of my baby girl, Sarah Eve. We had our son who was just a quiet chill little guy, and the market was showing signs of what was to become a recession. I was under quite a bit of pressure like most of us were so I had no challenges, no goals, just stayed focused on my businesses and my family. This picture is just pure love and joy in my heart.
2005 CHALLENGE: FLY A GLIDER OVER LAKE TAHOE
Flying has always been a dream, I mean, who does not have that dream? I wanted to fly over Lake Tahoe, and with one of the most amazing views from the ground I thought it must be unreal from the air. After the research, I found a place that offers the service and booked a class and flight. In 2005, I was airborne. The flight was quiet, calm and beautiful but also kind of bumpy. I became so motion sick I had to end the flight early and resign to the idea that this is something I can't do without creating quite the mess LOL.
2004 CHALLENGE: BECOME A FATHER FOR THE SECOND TIME
In 2004 I had one main goal, to support my wife during her pregnancy, and second to that, earn a living and keep the business going. She was an amazing support for me and was a powerhouse of courage in what is a physical and emotional challenge for even the strongest. I would often times look at her and feel so helpless. My son, Aiden, was born and the world for us become a brighter warming place. The motivation you feel from a baby is unlike anything I have ever felt.
2002 CHALLENGE: RUN 28 MILES OVER THE SIERRA NEVADA MOUNTAIN RANGE IN 1 DAY
n 2012 my mom and I, who was the most powerful person I have ever known, made a goal to run from one side of the sierra Nevada mountain range to the other in 1 day. The rise from 3000 feet in elevation too over 11,000 feet in elevation in 28 miles is extremely difficult. The trail was non existent at times, and weather goes from 100 degrees to 30 and back. I must admit, I did not run the entire way due to asthma that really kicks in when the air is thin, so I did run walks. We started at 4AM and completed the run at 8PM. No joke, my mom was only about 30 minutes behind me!
2001 CHALLENGE: DRIVE THE PAN AMERICAN HIGHWAY
In 2001, without knowing Spanish and having never visited central or South America I decided drive the Pan-American highway starting at Panama north. Although the actual Pan-American route mapped out is around 15,000 miles long, nobody does the exact route without venturing into many detours and side roads. The trip was full of surprises starting with the “jeep” I rented, which turned out to be a tiny little 4X4 from a manufacturer I had never heard of. The drive included parts where the “highway” would just disappear at a river without a road in sight. On one occasion, I drove down into a river, saw a road, and desperate to get out of the river as the water was filling up the “jeep”, ended up driving in the jungle for hours to end up in village with a combination of XPats and local villagers and a combination of German and Spanish speakers… like in the middle of the jungle, pretty crazy. The trip ended in Nicaragua when I saw a goat tied to the road by its tail and pulled over, only to see men with automatic weapons step out, it was a trap. I gave them all the money I had and turned back. The trip back to the airport included a boat, horseback riding, and a flight on a single engine plan… but what a blast! The people were so sweet and generous. I was so moved by their kindness, care, and love for someone they did not even know, it changed me forever.
2000 CHALLENGE: CLIMB THE CASTLETON TOWER IN MOAB, UTAH
Castleton Tower, a 400-foot-high sandstone spire near Moab, is probably the most famous desert tower in the world, and was the first major tower climbed in the Moab area. The Kor-Ingalls route is one of the 50 Classic Climbs of North America. I had been training and climbing now for a bit and after El captain I felt I was ready to lead an entire climb. A sandstone climb is very different then the granite that you'd find in Yosemite Valley and the tower has a different level of exposure. The climb is much smaller than some of my past climbs and once I got to the base after a decent hike from the road in the dark I thought, “ok this is doable”. The tower stands 1,000 feet and has a feeling of its own. The climb is about a day up and back so we started in the dark and the top was truly epic!
1999 CHALLENGE: CLIMB THE FACE OF EL CAPITAN
In 1999 after over a year of training and a climb of the east rock face of Long's Peak, I headed off to the ultimate climbers' heaven, Yosemite in California. Driving to the canyon all you see is the 3,000 vertical foot rock face that has killed 120 climbers, the captain, El Capitan. In the canyon its size and majesty was a sight to be seen from the lens of a person about to climb it. I could not even make out the people on the wall with binoculars; they were tiny dots. The next morning in the dark we left base camp for the "Nose", the route we chose to climb, and started our ascent. Pitch after pitch we rose out of the trees into the sky. The first night I did not sleep. Lying in a harness hanging off the ledge with tiny mice running back and forth on the ledge made it a rough night. 2 days of grueling effort later I reached over the last hold with shredded hands and forearms and stepped up over the lip. It was an amazing feeling.
1998 CHALLENGE: FACE THE JMT... AGAIN
The John Muir Trail is a land of 14,000-foot peaks, lakes in the thousands, canyons thousands of feet deep, and immense granite walls. Over the course of 3 weeks, we ascended 46,000 feet in elevation and summited 14 mountain passes as well as Mt. Whitney, the highest peak in the lower 48. We hiked about 10 miles a day with 65 pounds of supplies on our backs and 2 food drops. In 1998 there where very few people on the JMT, no books on the adventure, no movies. We saw two people on our journey which was more than usual. Besides the thin air, steep climbs, blisters and joint pain, you experience a range of transformations. Additionally in 1998, there were no phones and if there was there was no reception, no communication, which leaves you truly alone, isolated with heightened senses and a clear head with which to see life from another perspective. Day after day of heart pounding high altitude steep climbs, limited food options, and the nightly visit from bears hungry for your food after hibernation, made for light sleep. The views, fullness of life, and sense of the wild are overwhelming.
1997 CHALLENGE: CLIMG ALL CALIFORNIA 14,000 FT MOUNTAINS IN 14 DAYS
My brother offered me to be part of a 3 man team that would attempt to bag all 14, 14,000 foot mountains in California in 14 days to raise fund for multiple-sclerosis. We had not expected this to be as difficult as it was, after 8 in 8 days the whole team was unable to walk. We had under prepared, had no support team and the raids and approach to the assents turned out to be a huge challenge without a lifted 4X4, this cost us time which we train to make up with speed causing a few injuries and dangerous climbing without ropes. We called it in and I still will go after it again someday soon, however those 8 14,000 foot mountains in 8 days based on people I talked to was still quite an achievement.
1997 CHALLENGE: CLIMB 40 COLORADO 14,000 FT PEAKS IN 4 MONTHS
In the mountaineering parlance of the Western United States, a fourteener is a mountain peak with an elevation of at least 14,000 feet (4270 meters). The Colorado Geological Survey says there are 58 peaks that exceed 14,000 feet in elevation. My challenge in 1997 was to climb 40 of the 53 in 4 months. Why not all 53? Well time, weather, and the short climbing season. I was able to do 39 in that time and OMG it just killed me, but as they say “shit happens”… Whenever I set a challenge I fall short of I have to remember that the, focus, drive, discipline, optimism and enthusiasm that goes into the year of training brings with it all the value of the experience and is more often then not harder than the challenge itself. I was able to experience some of the most beautiful county I have seen, had wildlife experiences, saw amazing views, and climbed with some amazing people whom I love deeply and some that I have lost over the years. This year was a year of growth for me personally and most of that growth came from those climbs.
1996 CHALLENGE: DRIVE A NASCAR RACE CAR
In 1996 the idea of driving a NASCAR Race Car popped into my head after watching a race with my brother Rain who was a huge fan. After a bit of research, I found the Richard Petty driving experience was going to be in Colorado at the Pikes Peak international speedway. I experienced the 2.5 mile oval speedway with 31 degrees of banking turns. It looks like your heading into a wall when you get to the turns, the car sends you into your seat, and the sound of the engine ratels your spine. I have never been a fan of the races but I must say I am a huge fan of the NASCAR experience.
1994 CHALLENGE: BACKPACK ACROSS THE JOHN MUIR TRAIL
The John Muir Trail is a land of 14,000-foot peaks, lakes in the thousands, canyons thousands of feet deep, and immense granite walls. Over the course of 21 weeks, we ascended 46,000 feet in elevation and summited 14 mountain passes as well as Mt. Whitney, the highest peak in the lower 48. My brother and I had decided to do it in 21 days this time which meant less rest and longer days with more miles. Technology had come a ways from the last time I did the journey so packs were a bit lighter, but the mosquitos and blisters due to the heavy winter that year was intense to say the least. This trip was very special as I was able to see my mom and cousin on part of the trek. I found the experience to be less of a challenge and more of a spiritual experience this time. It's a wondrous, timeless land that reminds you how you are a small part of a much larger planet.
1993 CHALLENGE: BECOME A FATHER FOR THE FIRST TIME
My first baby girl was born in 1993. My challenge for that year was being a daddy for the first time. I was only 25, trying to make it in life it was a real struggle. She brightened my life. Talk about motivation!
1992 CHALLENGE: GET ADDICTED TO BUNGEE JUMPING
In 1996 I heard about this crazy new adrenaline rush called bungee jumping, I was on it. I started jumping out of hot air balloons, then bridges and finally sky cranes. I loved it so much I bought the company… and lost all my money, but had a great time and learned from the mistake. Over a period of 2 years I jumped over 400 times, went on to sky diving, ultra-light and hang gliding. What a blast.
1987 CHALLENGE: GRADUATE HIGH SCHOOL
My mom, with the discipline of a NAVY SEAL and the drive of a honey badger, started a preschool for under privileged children and a place I could get the special attention I needed. I spent hours with flash cards that would say, “focus”. I would sit for hours with the distraction of the sound of kids playing. I asked my mom, "whats wrong with me?", she would say “you think differently”. The tests revealed Dyslexia, Autism and auditory processing disorder (I hate the word), which I would not know about until I was in my 30’s. Talk about a surprise! I had struggled every day in special education, which was very different in the 80’s. I hated every single day. I felt so stupid, was told I was stupid and needed to try harder. After being home schooled and attending 4 continuation schools I had it! I was not going to give up, I would graduate! This was the first time I had set a challenge, "I would graduate this year” I said. I applied a layer of focus, hunted down some very giving and patent teachers and asked for help, and I pulled it off. I was not stupid, I was different, I learned differently. I did not know it yet, nor did I know applied right, my learning disabilities would be a gift!
1986 CHALLENGE: PLACE TOP THREE IN A BODYBUILDING COMPETITION
I spent my childhood getting bullied, was called names, and would get beat up almost on a daily basis. I was small and frail. I decided to hit the gym. Working out with weights was something I could do with asthma and free at the school gym. Even though I started with the goal of being big enough to stop the bullying, it become a passion, something in which I would be seen equal. I found it to not only decompress pent up emotions but also, it just made me feel good. I made the goal to place in the top 3 in a regional competition and I did it in 1986. The feeling of achieving and being a winner was absorbed in a visceral way and was pivotal in my belief that I CAN do things that I thought impossible.
4 PRIVATE EQUITY AWARDS
12 SUCCESSFUL EXITS
+ $1 BILLION IN TRANSACTIONS