My Questions → His Wisdom

A few days ago I was wrestling with a business issue and I decided to call a close friend to get some advice.  I grab my cell phone and instinctively dialed a number, even though my friend’s number is programmed into my phone.  After the phone rang a couple of times I realized that something was amiss.  I called the wrong number. I accidentally called my old boss/mentor with whom I had a close relationship. I hung up and oddly enough I dialed the same number again.  Weird!  Doesn’t seem like a big deal eh?  People dial incorrect phone numbers every day.  But what’s weird about this episode is that I twice instinctively dialed the number of my mentor, a man whose funeral I attended earlier this year.  I knew my mentor had died earlier this year but I still dialed and unconsciously reached out to him when I needed advice. Although he is no longer on this earth, many of his business and life lessons live on through me.  I thought I’d share a few of them given they were so impactful to me when I received them in my mid 20s.

Let me provide a bit more color of my mentor’s background so you can better understand his advice/wisdom when I share it later in this post.  His abbreviated story is:

  • Born in Aurora, IL in the 1940s
  • African-American male
  • Father drowned on a fishing trip while my mentor was young
  • First in his family to graduate from college (Southern Illinois University)
  • Joined Black Panther organization
  • Worked at Continental Bank (acquired by Bank of America)
  • Became a Partner at PriceWaterhouse Coopers
  • Started his own firm in 1984
  • Loved his wife and four daughters
  • Grew a multi-million dollar business

Ok, now you that you have a sense of the man that I had the pleasure of working with for eight years, I’ll share some of the business and life lessons, in no particular order of importance, that were impactful to me:

Look the part

My mentor was probably one of the best dressed businessman in Chicago.  The previous statement is not hyperbole, people would comment on his fashion sense all the time. He was always impeccably dressed in an expensive suit, shoes, watch, pocket square, etc.  When we first met he ‘encouraged’ me to upgrade my wardrobe.  It was a point of contention given I was of the belief that all that mattered was what I can deliver in terms of value, not so much how I look.   He agreed to a certain extent, but his experience taught him that as an African American male in corporate America we are judged ‘on sight’.  Research shows all people are making judgements within minutes of meeting you based on appearance no matter your race.  But my mentor realized that there are additional biases that come into play for African American males as well.  One of the ways to combat these biases is to present one’s self in the best possible light and that included how you dress.  I had a hard time accepting this at first b/c as young idealistic guy I believed the world operated as a meritocracy.  Hahahaha…it doesn’t.   My mentor knew the world, let alone corporate America, doesn’t operate in this manner.  The funny thing is he understood that looks are superficial, but he realized we needed to ‘look the part’ as soon as we walked through the door to give us fighting chance.  I invested in my appearance and upgraded my professional wardrobe. I’m still not at the level of my mentor because I’m cheapskate, but I’m working on it.

Listen, Questions, Facts

My mentor had the uncanny ability to listen.  I think listening is a lost art these days.  But those that actually listen during conversations tend to reap rewards for employing this skill.  My mentor would listen intently to every word, ask a few questions and then hit you with facts.  Not just facts, but statistics.  He was well read across a wide variety of subjects and he was blessed with the ability to recall specific stats. For example, I recall he once quoted the percentage of failed businesses in 1984 compared to those in 2004.  How can you argue against that?  And therein lies his lesson.  He taught me to have facts at my disposal because people’s arguments fall down because most people can’t argue against numbers/facts.  Their rebuttal is weak.  I read more than these days and I try to remember some facts.  I’ve realized he was right.

Who told you don't belong?

I’m smiling as I write this because I can hear my mentor asking, “Who told you that you don’t belong? And why do you believe them?”  It’s a rhetorical question he posed and he would pose this question when he sensed that I was experiencing some doubt about approaching someone and/or my hesitation to speak up in a meeting full of executives.   It was a great question, it made me realized that somewhere along my journey I accepted it as truth that I should be happy to be ‘here’ (wherever here is).  But my mentor made me realize that not only was I supposed to be ‘here’, but I should be leading the conversation.  Basically he was encouraging me to have confidence and know that I belong.  Today I know this.  I consider myself the man with anything at the intersection of business, technology, and growth...

Own it

I recall eating lunch with my mentor and asking him about working for multinational firms and rising to the ranks of an equity partner.  We talked about the time, effort, and sheer luck needed to accomplish this type of feat.  Then he began to shift the paradigm and he asked, “Would you rather work in a $500M firm and have a 1% ownership or build and own 100% of a firm worth $5M?”  You can do the math if you’d like to do so…but the value is inconsequential.  The real wisdom is understanding these are two totally different lifestyles.  Ever since I heard this question I began to care less about working for established brands just because of their reputation in the marketplace.  I desired to build lifestyle companies in which I controlled a significant amount of ownership and worked with talented and amazing partners.

I see families

There was a period of time when the company that my mentor owned started to contract.  I was in business school during this time and thought I really knew how to run a business…even though I had never done so at that point.  I recall encouraging my mentor to “reduce expenses” and “cut the dead weight”.  He just looked at me, smiled, and shook his head.  You see, my mentor had seen tough business times before.  He knew it was just a tough period in time.  But what he shared with me during this conversation has always stuck with me.  He said, “Jamail, I just don’t see employees.  I see the families attached to each one of these employees.  I can’t in good conscious make wholesale cuts.  We’ll be fine.”  This logic flew in the face of most of what I was learning in business school.  He brought a human element to business that I hadn’t considered at that point.  He didn’t establish this business just to make money, but rather he wanted to make money and help others make a decent wage and support their families.  I still struggle with this logic given you have to do what’s best for the business, but maybe what’s best for the business is going through hard times with others, winning their loyalty and trust, and coming out on the other side together.

Generous Capitalism

This leads into another amazing quality my mentor possessed. I like to call it ‘generous capitalism’.  He was all about business, but he realized the business allowed him to give to others.  And boy did he do that.  I don’t know all that he’s done for employees and families of employees over time, but I do know that he:

  • Provided internship opportunities for underprivileged high school kids
  • Paid for tutors for kids he realized were falling behind
  • Paid for college for employees’ kids
  • Provided jobs for men and women that needed to “get back on their feet” after being downsized by larger companies
  • Donated time and money to the arts in inner city Chicago

He just did a ton with his resources.  This was a reminder that building a business is not only for me.  Life is much larger than my selfish wants and desires.  Now I ask, “How can building this business help others as well?”

“That's not your problem”

Is the refrain I’d hear often from my mentor.  He was adept at understanding and analyzing a situation to determine what needed to be done.  Often he suggest doing nothing because the issue didn’t lie with him, but it was something that the other party was struggling with.  Let me provide details.  My mentor was a commanding figure. He wasn’t tall (under 6 feet), wasn’t big, and didn’t have a booming voice.  But he had the strongest most authoritative presence of any one that I met.  As soon as he walked in the room people began to show deference to him.  It’s unexplainable why this happened time and time again, perhaps it’s a result of the way he carried himself.  Now the added layer is that he was a black man, super confident, would speak his mind, and had a commanding presence.  I hate to say it but this doesn’t sit well with many in corporate America.  I wish I could explain why this is the case, but there have been many times where he was pushed out of a deal or passed over for a partnership.  I used to review the business reasons to understand these occurrences but I could never find the reasons to justify the actions of the other party.  My mentor understood what had happened each time.  He would tell me how some struggle with working with a confident, smart, black man.  He also advised to never mute your strengths because others are insecure.  He would say, “That’s not your problem…that’s their issue”.  No need to waste energy solving for their issue(s) and biases.  Having worked in the corporate world for almost twenty years, I can say that my mentor was right.

RIP buddy. Thanks for the wisdom, fun, and generosity. Your presence is greatly missed…

Jamail Carter