Category Archives: Inspiration

Finding A Great Mentor Is Hard. Here’s How I Found Mine.

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Having lunch with my mentor Ed Neff.

There has been no greater impact on my professional, personal, and romantic life than having mentors. That’s right, I have someone’s guidance in every aspect of my life so, yes, I even have a love mentor! The benefit of mentorship hasn’t only been through my role as mentee, I’ve also realized the power of being a mentor, starting in college with the Big Brothers Big Sisters program and continuing through today where I still mentor several people.


While mentorship has a certain meaning to many, it’s not neatly defined, causing confusion about exactly “what is a mentoring relationship?” The largest misconception I’ve noticed is the thought you can’t be mentored unless you have an official relationship with someone who confirms they’re your mentor. This is an old and limiting belief. I spent the early part of my business career being mentored by Steve Jobs, Bill Gates, Susan Taylor, & Reginald Lewis. None of them knew it, though. I believe simply listening to someone’s speeches, reading articles and blog posts they’ve written, or exchanging thoughts with them via social media, can all be considered “being mentored.” At the end of the day, I define mentorship as a personal development in which a more experienced or more knowledgeable person guides a less experienced or less knowledgeable person.


That being said, you won’t get an argument from me about whether formal mentorship is more effective. It’s MUCH more effective! [inlinetweet prefix=”” tweeter=”” suffix=””]A relationship with established roles and defined expectations always gets optimal results.[/inlinetweet] So how do you structure a formal mentoring relationship, especially with someone who is highly sought after? Well, the first thing to know is while it may seem against conventional thought, whatever you do, please, please, please do not ask someone to be your mentor. Seems strange, right? You would think in order for someone to be a mentor, you would need to ask them.


The problem is when we ask we’re typically asking strangers, people we have only met recently, or those we don’t yet have strong bonds with. Sheryl Sandberg, COO of Facebook, sums it up best in her book Lean In:


“If someone has to ask the question, the answer is probably no. When someone finds the right mentor, it is obvious.  The question becomes a statement. Chasing or forcing that connection rarely works.”


So the real question is not so much “how to ask someone to be a mentor” but rather, “how to build a rapport with someone you would like to become your mentor?” Here are the 5 steps I used (as well as steps that were used on me) to seal the deal on my most rewarding mentoring relationships.


1. Become Mentee Material

Are you somebody you yourself would like to mentor? Are you open, flexible, resilient, and respectful? Are you eager to learn, and committed to modifying how you’re interacting in the world so you can have even more success, reward and happiness?

If the answer is “no” don’t move to step 2 until you nail this one first. It took several failed mentoring relationships for me to appreciate the importance of becoming mentee material. Be someone who is already actively building his/her life, and is demonstrating that every day.


2. Make Sure The Person Shares Your Values

Don’t simply see their awards and accolades and because you aspire for those same things believe he or she is the right person to guide you. It’s critical that you know your potential mentor has the same values you do. Values are essentially your guidebook to life. If your mentor has different values, it means they play by a different set of rules from you. Some of which you may consider immoral or unethical.


Most people searching for a mentor don’t focus on values because they either don’t know their own (and so don’t have anything to match against) or don’t want to expend the effort to assess someone else’s values. Determining someone’s values requires dedication. You have to watch actions play out over time. While values are key, I don’t believe any other similarities are critical – so your mentor doesn’t need to be the same ethnicity, religion, gender, or nationality. My greatest mentors (like Ed Neff pictured above) have all been different from me in many aspects, but we always had the same values in common. Shared values are the single most important matchmaking category for success (and that’s in all relationships – business, platonic, and romantic).


3. Advocate For Their Work!

Tweet their posts, comment in a positive way on their blogs, share their updates, start a discussion on LinkedIn about a post they’ve made, promote and attend a live talk they’re giving, and the list goes on.  In short, offer your unique voice, perspectives, experiences and resources to further the action and conversation that these influencers have sparked.  Understand that you are able to be of service to them, and go out and do it. In particular, show up in their comments – this is where many people with large followings go to for their “oxygen.” Continue to show up, give insight, and provide value, consistently. It’s important to note this step isn’t simply about advocating their work for a few weeks and thinking you’ll be noticed immediately. It takes time and keep in mind, you may never be recognized for being their advocate. It took me 4 years of consistently promoting and attending his independent film events before finally connecting with someone who later became my mentor, Ed Neff. What got me through those many years of advocating with no reciprocation was shifting my mindset to giving with no expectation.


4. Elevate Your Value To Them Over Time

Go beyond the comments and offer ideas, refer new clients or business to them. What finally placed me in a position of strength with Ed was when I introduced him to a potential acquirer of one of his businesses. This increased value will move you from someone your possible mentor sees as merely a member of their audience to a member of their network. It’s this critical step I see so many not do and it’s the one strategic move that will most differentiate you from mentee potential to mentee personified.


5. Don’t Ask For Mentorship, Make A Statement

Going back to the Sanberg quote above, you’ll know your relationship is in the right place for formal mentorship when you don’t have to “ask” but simply say – “you’re my mentor.” I recall when I made this same statement to Ed, we were having dinner and towards the end I simply said “thanks for being such a great mentor.” That was 7 years of stellar guidance ago.


Finding a great (formal) mentor can seem daunting, but start where you are. Begin through the inspiring people you’re already interacting and working with now. Mentors need to be people to whom you have demonstrated your potential – who know how you think, act, communicate and contribute. And they have to like, trust and believe in you already (why else would they help you?).  They also need to believe with absolute certainty that you’ll put to great use all their input and feedback.


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The 10 Books That Changed My Life

In a recent post I wrote about how I significantly reduced how much TV I consume and dramatically increased my reading. A key reason for doing this is because upon reflecting on “activities” that have led to substantial changes in my life, I can’t count one TV show as the catalyst.

I can, however, point to several books. Here are 10 books that have had a profound influence on my life…

10 Books that changed my life

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10 Lessons I Learned While Making My First $1 Million

The last 6 years in business have been transformative for me – both personally and financially. I have never been more fulfilled and purpose-driven than I have been doing what I do. And, as a result of stepping out on faith (it took a huge leap of faith to leave what others thought was a secure lifestyle to delve into the unknown), I’ve learned some powerful lessons. This journey has taken me places that I’ve only dreamed of going, while accomplishing some key milestones along the way.

Folks always ask how I did “it.” Recognizing the importance of paying it forward and sharing what I’ve learned, I managed to synthesize an actionable list of the 10 lessons I learned while making my first $1 million.



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20 Successful Habits I Learned Working For Two Billionaires (Part 2)

In Part 1, we looked at general lessons I learned working for billionaires Oprah Winfrey and Enver Yucel. In Part 2, I continue with deeper insight into successful habits – specifically for business-minded readers seeking to understand how extraordinarily successful people reach the top of their fields.

 Successful Habits

It’s my honor to share with you Part 2 of successful habits I learned working for two billionaires:

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10 Things You Must Stop Doing Today to Believe In Yourself

Reflecting on the commemoration of Dr. Martin Luther King, Jr.’s achievements, it’s important to consider the one thing that made it possible for him (and many others) to indelibly impact the world: belief in self, first. Dr. King’s “dream” is often noted and recited. Still, it’s important to remember that in order to express and ultimately realize your own dreams, you have to believe in yourself.

Everything we have in life comes because of our belief that they are possible.

Yet, believing, especially in yourself, is much easier said than done. I know this first hand, because for the majority of my adult life, I suffered from one of the most debilitating diseases known to man – a disbelief in myself.

Believe in yourself

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20 Things I’ve Learned After 7 years of Being a Professional Matchmaker

2016 marks my 7th year as a professional matchmaker. Thanks to the addition of an incredible team added in 2013, my agency has dramatically increased the number of clients we serve and our client geographic footprint continues to expand, as well (last year we coached and matched people in the United Kingdom, Turkey, India, and the United States).

Since 2009, my firm has served over 1,000 coaching and matchmaking clients. For our matchmaking clients, we directly organized thousands of dates in 2013, alone. Some of those dates went incredibly well (and led to committed relationships), some of those led to platonic friendships, some of them there was no “chemistry,” and some completely blew-up with both parties hating each other.  All in all, I took notes on everything.

Over the years, I have gained an incredible amount of insight on how commitment-minded singles date and interact in the early stages of a romantic relationship. Here are 20 of the most interesting things I’ve learned:


1) Everyone should be in therapy


I’m not kidding. 1 out of every 5 people in the United States have been negatively affected by someone else’s pathology. This means you have had a relationship with or are currently a sociopath, psychopath, or have a disorder associated with ‘no conscience’. Serious business. You may be out of the relationship, but the relationship may not be out of your mind. The clients I have who are actively engaged with therapists are typically the ones who gain the most from their dating experience.


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(30 Steps to a Better You) Step #3: How To Write A Personal Vision Statement

“Your vision will become clear only when you can look into your own heart. Who looks outside, dreams; who looks inside, awakes.” – Carl Jung, Swiss psychiatrist and psychotherapist

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A lot of us can see, but how many of us have vision?

Having “vision” is the ability to perceive or project a vivid mental image of your future, and crafting, breaking down and setting goals for the future are the next three steps in our 30 Steps to a Better You exercise.

Step three is all about creating your vision statement. According to Business News Daily, a vision statement is a “future-based” self-assessment that is “meant to inspire and give direction.” It’s all about what’s possible and what’s ambitious.

Now the first time I was presented with the idea of writing a personal vision statement I thought it was a joke … until I realized it actually worked! I saw how writing down and organizing my thoughts made me see my “vision” more clearly. It made it easier for me to plan ahead and act on things that would make what had been only a dream reality.

So how do you go about creating your vision statement? Well, we’re first going to start with an exercise I call “Tomorrow Is A Good Day.”

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#GoodPeopleProject: Homeless to Hopeful

Anthony Ross has a harrowing story that’s hard not to be moved by. I was moved by it when I met him, a young man who’d been homeless since he was 13 and before that, living in poverty with his drug addicted mother. Anthony, despite his difficult upbringing and homelessness told me he had a dream. It was to get out of his cycle of homelessness and poverty and go to college. Together, with taking Anthony on as a mentee, we set out just to make that happen. The following story was captured by a staff writer for the #GoodPeopleProject 

Anthony Ross

Anthony Ross is a dreamer.

Although it may be surprising to learn that, once you know where he came from. Where can one find dreams when all you know is pain, hurt and poverty? And yet Anthony had them. He had them at his darkest moments and in the direst circumstances. Dreams for a better life. For a way out of a cycle that for far too many young black boys leads to death and ruin.

Anthony grew up in Washington, D.C. where he and his older sisters were being raised by their grandmother. But while some grandparents can carry the load, Anthony’s grandmother wasn’t equipped to care for him.


“Whenever I got in trouble I’d get locked in my room for days without eating,” Anthony said. “I accumulated a lot of diseases from not eating. My grandmother didn’t have the patience.”

Her lack of patience lead to them not having much of a relationship, yet, when she died from heart disease an already rough situation became worse as Anthony and his three older sisters were sent to live with their crack addicted mother in a house with no heat, electricity or running water in Upper Marlboro, Maryland.

Even less fit than their grandmother, their severely addicted mother tried to attack her children with a meat cleaver.

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(30 Steps to a Better You) STEP #2: Identify Your Passion

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“Passion is energy. Feel the power that comes from focusing on what excites you.” – Oprah Winfrey

In our next step in “30 Steps to a Better You,” it’s all about finding out what you love and working towards that, also known as finding your passion. It dovetails nicely into what was last week’s task, identifying our values. If you followed along and did the homework for that step – making a list and breaking down what your core values are, then acting upon them – you’ll be better prepared for this step where knowing your values is crucial.

Because now, we’re going to turn the things we value most into our passions.

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(30 Steps to a Better You) STEP #1: Identify Your Values

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“Our necessities never equal our wants.” – Benjamin Franklin

Would you want a sports car that couldn’t drive you anywhere? It would look nice. The stereo system is incredible. The rims are chrome and shining. But when it came to a car’s basic function – to get you from point A to point B – it couldn’t get you there. Would you still want it?

The answer is easy. No.

What’s the point of having a car if you can’t drive it? Because all those nice things, the stereo, the chrome, those are things you might like to have in a car, even want, but what you need is to get to work, to get to the grocery store, you need a ride and if it can’t give you one, what’s the point?

That’s the difference between a want and a need – and needs are values, the things that really matter to us.

I believe “identifying values” is the most important single exercise we can do regarding self-awareness. In this step, the first among our “30 Steps to a Better You,” is all about putting together a car that drives (or in this case a life that works) – by focusing on what really matters.

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