(This was written by request to be included in an upcoming friend’s book)

During my childhood family vacations that took us far west away from the flat plains of Chicago, I used to love rock jumping with my brothers.

We’d find a rock, put a leg back to wind up, jump, and land safely…most of the time. Then on to the next rock.

Usually the jumps were pretty easy and at a length I’d done a thousand times, but occasionally we’d get to a rock that was at a length I’d never done before. My mind would race. “Will I make it? It’s too far. You can do it. There’s only one way to know for sure!” And off I’d jump. At some point, mid-air, my eyes closed and all my focus was on hoping my feet hit solid ground…instead of my face. Success! Off to the next rock I went.

As an adult I don’t physical rock jump anymore, but in growing my business I do mental rock jumping all the time. The biggest difference is unlike my childhood where I could see the rock and how far the distance was, in mental rock jumping, I only have guesses as to how far the jump is, or if there’s even a rock to land on on the other side. This is the entrepreneurial leap. This is the moment when the idea of uncertainty, or the unknown, either propels you forward in a quest to know the answer, right or wrong, or holds you back out of fear.

I jump a lot, but leap only once in a while. I love the quest of the unknown. It’s exciting, and unlike with real rocks where I could end up in a hospital, the damage of mental leaps is only what you allow it to be, and for some people it is far worse than anything a hospital can fix.

My latest leap was to start another web tool called www.alumnichoose.org. It was expensive both in upfront costs and in opportunity costs for not focusing my energy elsewhere. I did the usual market testing that one would expect for a new idea and all signs pointed to a green light. So I put my leg back, wound up, and leapt. I’m still in the air today.

All my data, research, and vision shows me that there’s a landing rock on the other side, but I won’t know for sure until it actually happens. But here’s the trick. It may never happen. I may never fully feel solid ground and so in-flight becomes my new ground. All the sudden everything changes.

By not needing to worry about my landing rock, I can more freely, and happily, enjoy the never ending quest of the unknown. Now I find myself leaning into the uncertainty I encounter, with my eyes wide open, because in flight is the exciting part, it’s where life happens.

Blogger James Altucher challenged his readers to create a list of the ten things that make you happy. Here’s my list…

1. Spending time with my wife
2. Spending time with my family
3. Building things people value
4. Building financial wealth
5. Spending time with friends
6. Reading (learning)
7. Traveling for pleasure
8. Being active (soccer, hiking, etc)
9. Daydreaming
10. Connecting with student leaders

Bonus list…

1. Writing my blog
2. Meditating
3. Networking

What would you put on your list?

In person time with my family is the best, but not always possible.

Tonight Ido Leffler, the founder of the fashion product line “Yes to Carrots,” spoke to the NY Entrepreneurs’ Organization at the Trump SoHo ballroom. Here are my short-hand note take-aways from the talk…

• In sales, he’d inject an urgency into trying to get a meeting with someone. If he were coming to NYC for a week, he’d call up potential clients and tell them he was calling all the way from Australia and that he’d only be in NYC for one day and would love to meet with them. “You’d be surprised at how urgency gets people to act fast.”
• Treat employees like royalty.
• Take every meeting if you are the brand ambassador for the company, because you never know what meetings will lead to what. (My Note: If it’s a bad meeting, have an exit strategy because they can suck up your time. I’ve been there.)
• Fly only one airline to rack up the miles so you get upgraded. You’d be amazed at who you sit next to in first class and get three hours to build a relationship with over free drinks.
• “We saw all our competitors saying no to bad ingredients and we wanted to be opposite to that, so we became a company that said yes to good ingredients.”
• Have a social cause for your employees and even your clients to rally around. You sell product, but what do you sell it for?
• “The scariest thing for me is to be an employee.”
• “QVC and HSN are like bungee jumping for entrepreneurs.”
• If you can raise money once all together, that’s the best. A second funding round is massively complicated and ugly.
• “I am a good entrepreneur, I’m not a great CEO. Know when to let go.”
• If you’re going to outsource, outsource to experts.
• “We were extremely transparent with our finances with our employees, but we never let our employees doubt the fact that we were going to be huge.”
• “We don’t employ people, we adopt people.”
• “Employ good people.”
• “When you don’t want to do a holiday party because of all the stress, it is the most important time to do a holiday party.”
• The story matters. Your story and the company story, because everyone will ask you about it.
• “We built massive loyalty among our customer base. We have a VIC [very important carrots] program.”
• “Our customers know way more than we do, so we constantly connect and learn from them.”
• As the CEO, it’s important to smile all the way through
• “As a founder, even if you sell your company, it’s still your baby forever.”
• “My family is my rock. They ground me. They keep me sane. Bath time is my favorite time.”
• Take your ego out of the business.

My dad turned 70 this year and in celebration my oldest brother, Robin, had his son record this cutness filled video. 

Since I was only three years old when my younger brother Michael was born, I can’t say I remember anything about his actual birth except for family photos like the one above. But the next 17 years of growing up together were filled with plenty of great stories, so I figured it would be fun to share one of those stories on his birthday…

Story Title: Duct-Tape Parental Surprise!

Our family took a lot of family vacation road trips. It started with packing all seven of us, plus equipment, into a VW Van, but eventually, as we all got older and bigger, we upgraded to an RV.

During one trip to the SouthEastern part of the U.S., my parents left us kids alone in the RV for a couple hours while they went for a walk. Michael, being the youngest, tended to never fair well when our parents would leave him alone with his four older brothers. This time was no exception.

We decided to take all the extra duct-tape that was sitting around the RV and completely wrap Michael in it from head to toe. By the end, his hands, feet, and arms were bound tougher by tape. We then taped him to one of the seats in the RV and put a sock in his mouth.

Let me pause for a moment and acknowledge how horrible this sounds, but Michael did play along, and considering I grew up with all brothers and no sisters, it could’ve been a lot worse.

Before our parents came back, we hid in various spots throughout the RV so all that was left was Michael bound to a seat with duct-tape covering his whole body and a sock in his month. We even attached a little note that said, “help!”

You can only imagine my parent’s reaction…

About a year ago my brother’s wife, Suruchi, brought up the idea of doing a big surprise 40th birthday bash for him. At the time, the rest of the brothers were excited, but planning something a year out with my family is next to impossible.

Fast forward a year later and over the past weekend, we did the impossible. All four of my brothers, my dad, and myself rented a lake house for four days and three nights in central Wisconsin. Though we grew up taking road trip vacations two times per year, this was the first time all the brothers have taken a vacation together in at least 13 years.
It took a lot of pre-planning to make the vacation happen, but for me it was totally worth every second because no matter what, there is still nothing quite like family. As we all grow older and spread out across the country, quality “together-time” is a rare thing.

Most of our extended family is in Germany and we don’t get to see them very often, so I’m jealous of families who do a big family reunion every year. But coming out of our inaugural family reunion, I have a lofty goal to make it an annual event and an even loftier goal of owning lake property that we can keep depositing new memories into year after year.

Up until I was about 14 years old, we took family road trips around the US every summer. Our trips involved my two parents, four bothers, and me packing into a VW Van stacked full of food and camping supplies. As we got older we upgraded to an RV with built in kitchen, bathroom, and shower. One of our first trips in our new RV was to visit family along the East Coast with a swing through NYC.

Having never visited NYC, I only knew this larger than life, big shot city through its portrayal in movies and T.V. As a farm boy, actually visiting there made nervous.

With our RV, my dad rolled across the Brooklyn Bridge, through Chinatown, and found a place to park downtown on Wall Street. To me, Wall Street was the pinnacle of New York and all the power it held. I remember feeling so small and out of place as my dad parked our RV next to two black town cars that I’m sure were there to pick up some multimillionaire CEOs. Something inside me wished he’d parked outside the city and we walked in so not to disturb the power flow of the city.

Instead, my dad got out of the driver’s seat with an ear-to-ear smile on his face and proclaimed he was going to take a shower on Wall Street. At the time I remember wanting to hide under a blanket to avoid the embarrassment from the CEOs seeing my dad shower on their street as they walked by. But he showered, no one saw, and we went on with the rest of the day.

His shower on Wall Street became an epic story to tell among our family and friends. In fact, my dad’s whole life is filled with similar adventures that didn’t happen by accident, he made them happen.

I saw Wall Street like everyone else saw Wall Street, and in doing so, my experience of Wall Street was just like everyone else. On the other hand, my dad saw Wall Street in a totally different way, and in doing so, had an amazing experience that I’m retelling 18 years later.

If you know me, you know I am always fresh off of some new adventure that most people don’t believe actually happened. What you are really seeing is my dad’s approach to life living on through me.

Since moving to NYC a year ago, I don’t get to see my dad as much as I did when we were in Chicago, but no matter where I’m geographically at, I take with me many of his life lessons. His lessons, however, don’t come as lectures or rules, but rather in the way he lives his life. He won’t tell you what the lesson is, but rather patiently wait for you to discover it knowing that the teacher doesn’t show up until the student is ready. Sometimes I’d understand the lesson within a couple hours and other times it wouldn’t click till years later. It took me until college to understand what he taught me on Wall Street and I’m forever thankful.

An old man in our building passed away a couple weeks ago. I only saw and spoke with him a couple times. Annie and I nicknamed him Morgan Freeman because of a striking resemblance.

I found out about his death because of a police notice on his door and asked our Super what happened. Our Super said the police sealed his apartment because they needed to go through his stuff to find someone to call. They haven’t been able to find any one yet nor has anyone showed up. That’s sad.

I remember someone telling me how the first two rows of your funeral are the people who really count. The exercise then is to think about who would be in the first two rows and make sure to put an effort into keeping and building those relationships.

In full disclosure, this is my brother who’s written and preformed a ton of amazing music and continues to impress and inspire me with his creativity.