Hustler vs. Entrepreneur

I was having a real heart to heart conversation with an employee yesterday who is a great young man, hardworking, enterprising, and candidly expressed he was at a crossroads in his blossoming career as to “working in a company” or “being part of something where he can get an equity stake and feel the satisfaction of building something and ultimately making more money as an owner.”    I really appreciated the candid dialogue and said in our conversation (but didn’t use the word “Dude”).  “Dude, I understand the challenge.  I mean, I have never worked for anyone myself, I’ve never had a real job, I’ve always hustled and done what I needed to for over 50 years to build my various companies—and so I get it.” 

I really did empathize with a person less than half my age, at the start of their careers with the entire world in front of them, wondering if they should work for City Winery, in a very exciting, growing way, dynamic way, but where a good salary, target bonuses, team bonuses, management options, and all the things we do to create incentives, a great culture, stimulating work place, is simply not enough.     I recall a conversation I had with my 25-year son, the same age of this dude, when I offered him a short consultancy on a start-up opportunity on a risky side project that needed a business plan built, some due diligence and research, which included a clear $500 a week cash payment for 15-hours a week or so.  The project had the budget to do this and my son, who I knew was juggling a few gigs simultaneously and living at home, I thought would jump on this great opportunity to earn a bit of money and have input into a really cool important project.   However, after a few minutes of talking, he said, “How much equity will I get?” 

OK, fine, he is a chip off the old block, but to turn down a few grand a month for 1/5 of your time, I didn’t understand.  (I felt the urge to do it myself).   And since there were no real investors yet, and I too didn’t understand what my role, my piece, my equity would be, how could I make any solid offer to my son for some part time work.    I offered a small % of my % if this thing ever got off the ground.  He passed on the gig.  Yes, this certainly is a generational thing where a short hustle for a true entrepreneur is not satisfying.  There needs to be more too it.  It needs the adrenalin of hustle that includes the long-term intrinsic value of the connection that some form of equity compensation offers.    And it turns out, my son made the right choice.  That was 8 months ago and while he still is living at home, he has built a business now that is cash flow positive on track to get some investment creating several million dollars of value for  his sweat equity.   Good for him, I am a proud Dad.

So this other kid, my employee, same age, who has worked for me for a year has a similar mind set.  While different set of skills than my son, there is certainly an overlap of something that is being a hustling entrepreneur--willing to go the extra mile, sell a bit harder, put in those extra hours to see the fruit of your labor that is beyond a paycheck. 

I recall the first time I was called a “hustler” but someone I really respected and was not sure if it was a complement or a backhanded insult.   One of my great mentors was George Wein, the impresario who created the Newport Jazz & Folk Festival, New Orleans Heritage, Playboy Jazz and so many more.  We had a wonderful relationship with him being 36 years older, wiser, and more successful.  I remember him calling me a hustler, but he explained once over dinner years after he said it, that he meant as a complement, that he thought it meant it set me apart from other promoters and people he saw come up in the biz. That I was not ever giving up.  That I put the extra effort into it, beyond the money.   Like Paul Newman with Jackie Gleason in the 1961 “The Hustler” which I re-watched last night for first time since who knows when, Paul who plays “Fast Eddie” has a deeper need to challenge Minnesota Fats played by Jackie Gleason.   There is also George C. Scott who essentially plays Bert in the role financier and says Eddie has “no character” in the early parts of the film.   

There might be a deeper plot in this classic film about billiards, but I took that a true “hustler” hustles for more than a paycheck.   While Eddie was a great pool player, “a shark” who  eventually wins over the greatest player in seedy New York pool halls near Pier 57 in NYC (check out the old cinematography),  it’s about self-awareness, knowing what provides fulfillment as a human being.  Paul Newman, I mean Eddie, is willing to walk out on the short-term cash for the satisfaction of doing his job successfully.   Maybe I am reading and contorting the plot to support my thesis a bit, but I am the one writing this, so I can.

To foster a young person’s talent and sharpen their skills, there is the do it yourself track or the mentor and learning track.  And while the former comes with greater risk, the later allows for learning the wisdom from many years of trials and tribulations.   Both are valuable.  Part of being an entrepreneur is the willingness to make mistakes, take the risk financially and the body blows to the ego of questioning one’s own tenacity and sanity when things are challenging and not on plan.  So, my advice to my young employee is:  are you ready to give up a good paycheck, lots of perks and benefits, and jump into the unknown?   You have the hustle, you have much of what it takes to be an entrepreneur, but are you ready and willing? Is the time right?  Is there some compromise that balances out the risk of leaving what is a path in front of you with the ability to be rewarded for achieving results in a larger enterprise for now.  Can you sacrifice for short-term the desire to own your thing, for the value you will gather besides money, waiting a few more years to go at it with a much larger tool-kit?    I don’t know the answer for you, but these are the questions you should be asking yourself.   It’s not about confidence, you have it.  It’s about when to make the move, when to take your shot.