I love my job (if you can call it that) because I get to work with excellent entrepreneurs and business owners.  They are inspiring people with the optimism to improve the world, the bravery to double down on the roller coaster of the inevitable ups and downs of life (and business), and the intelligence to see things others do not and adapt over time.  I love it.  I particularly love supporting them, providing them input when requested, asking questions that may lead to some insight, and seeing them succeed.

My realization that I loved supporting entrepreneurs and business owners began in the mid-1990’s.  And, I can point to a particular moment in 1996 (I think) where I bought a tiny business from a college senior at Northwestern University and hired him to run it post acquisition.  His name was Mike Lazerow and the business was University Wire or U-Wire.  Earlier this week, Mike and his wife Kass announced they had an agreement to sell their business, Buddy Media, to Salesforce.com for $689 million.

My deal with Mike was almost as big of a deal to both of us at the time.  My start-up company, The Main Quad (a website for college students with the mission statement to “connect college students to each other, themselves, and the world” — sound familiar?), paid a grand total of $10,000 for U-Wire.  It was all the money we had in the bank at the time.  I signed the deal with Mike and slept on his couch that night because I had no money for a hotel room.  For the next few years, Mike grew U-Wire steadily and stuck with us at the Main Quad as we merged with Student Advantage.  I then invested in Mike’s next start-up (Golfserv that he did with his wife Kass and Mike Caspar) and sat on his board.  Through U-Wire and Golfserv, I tried to add value to Mike’s endeavors and I think began learning how to provide support and not get in his way.

In watching Mike over those experiences and now from a distance while he did Buddy Media, there are a few things that I particularly admire about Mike and Kass and would encourage all entrepreneurs and business owners to endeavor to do well.

• Be an excellent communicator.  No one can write a compelling email like Mike.  I was amazed at how Mike, even as a college senior, could write an email that could get the attention of anyone.  He consistently got the attention and therefore struck partnerships and deals with big time publications, revenue partnerships, etc. because he could communicate with the best of them.  Everyone can improve their communication skills and it pays big dividends.
• Establish/develop the emotional intelligence to navigate personal relationships with multiple elements.  In the case of Mike and Kass, this became particularly apparent in their skill in making a business partnership work while being married.  The data shows (see Noam Wasserman’s book, The Founder’s Dilemmas: Anticipating and Avoiding the Pitfalls That Can Sink a Startup) that start-ups with partnerships with family or friends fail more often than partnerships among other types of co-founders.  Mike and Kass worked together as partners at both Golfserv and Buddy Media and therefore navigated together two successful start-ups on a world class level.  That isn’t easy and they should be commended for that.  They also have been able to manage their partnership in combination with other co-founders — an even more difficult task.  This demonstrates an awesome emotional intelligence on the part of Mike, Kass, and their co-founders.  We all can constantly improve our emotional intelligence and our ability to manage interpersonal relationships.
• Wise persistence pays for entrepreneurs (not suggesting blind faith).  Persistence and determination are often cited as key characteristics of successful entrepreneurs.  That is true, but equally as true is the wisdom to know when to hold ’em and when to fold ’em.  Mike and Kass showed very wise persistence in their experience at Golfserv.  The time in the early 2000’s after the dot-com bust was not easy for Internet entrepreneurs.  Mike, Kass, and Mike Caspar managed through that time wisely and demonstrated a wise persistence in their efforts.  Wise persistence pays off and we all should look to be learning and improving our wisdom for these moments and the skills necessary to persist when it makes sense.
• Pick a playground with a lot of potential.  As Mike was considering his start at Buddy Media, I remember talking with him as he was trying to decide between another Internet endeavor (Buddy Media) or something in the skin care arena.  Both are very high potential areas.  I think Mike chose wisely (obvious given the outcome) because it built upon his earlier experiences, personal network, and skill set.  Skin care is also a good area as I have friends with great success in that area.  It takes as much effort to start a tiny business in a small town somewhere as to launch a global level business — you might as well play in a large playground if that is what you are interested in.

I could go on, but I will save it for another day.  Congratulations to Mike, Kass, and the entire Buddy Media team!