Cortney Woodruff, tech investor, entrepreneur, and Executive Chairman and co-founder of Assemble, shares the crazy story of the interaction at gunpoint that delayed his Action Catalyst appearance, a clever deal with his college professors, socially re-engineering what success looks like, how to muster energy late in the 4th quarter, and throwing potential business partners an alley-oop.

On today's episode, host Dan Moore speaks to Courtney Woodruff, an American tech investor, entrepreneur, founder, and CEO of Trainer's Fault, as well as the executive chairman and co-founder of the online education platform assemble a streaming platform that provides online courses taught by experts from around the world.

Woodruff's Mission merges worlds and creates opportunity by connecting black thought leaders across industries to a broad learning community.

We hope you enjoy.

Well, Courtney, before we dive in, I wanna let our audience in on a little context for this interview that you and I were just discussing.

This is actually our second attempt at having this conversation, cuz the night before we were originally scheduled to speak, you quite shockingly found yourself a gun point during an harmed attack.

We're so thankful you weren't harmed and you were just sharing with me that you amazingly had a pretty positive take on that whole situation.

Yeah, that was just insane.

A lot of that stuff has been happening around here though, so I don't take it too personal.

Just try to find like, the pros and, and the like, the positive light to kind of shine on it, you know, the night it happened, because I haven't told most people that, right?

I, I have this tendency to try to like correlate these subtle things in my life to like people that I've studied or admired.

And so something that I found was pretty.

For all the, the individuals that kind of created industry in this country and around the world.

There was always this life or death moment that hit them and, and they were spared like John d Rockefeller, like his, the first time he was getting ready to go meet Cornelius Vanderbilt to do a deal, he missed his train and that train actually fell off.

There was a huge catastrophe in, everybody fell off a bridge and everyone passed.

And that was like the sign in his mind from God to tell him like he was really doing the right thing and his life had been spare.

And it gave him like that next level of confidence to ultimately be very, very adamant and brave and determined in his decision making with building standard oil.

So I kinda looked at it like that, like 30 minutes after to having like two guns held in my head and.

This is a sign I just got spare.

You know,

, Dan Moore: that is absolutely right.

Well, you've done so many amazing things and you're really helping a lot of people, but I know our listeners always enjoy hearing a bit about the backstory.

Could you share maybe some of the most significant people that influenced you, and then also the events that maybe caused you to redirect yourself, and then years later you realize all those events added up to where you are.

They definitely have, you know, none of our paths are linear.

You know, there have been some key, key moments in my life.

The first was probably just my family.

My grandfather actually in my grandmother started the first black owned grocery store in Jackson, Mississippi in the seventies.

So, you know, as a kid I grew up in that store and I saw my dad working it and taking over the family business and it actually.

In the neighborhood, um, that mega Everest lived in as a kid, I, I vividly saw his house where he was murdered, and it's also the neighborhood and the community of the movie to help, you know, so it was that area.

So I guess I kind of had the entrepreneurial spirit in me, and I didn't realize it, but.

By my family being successful at that, they really was the go to resource for a lot of people in that community.

You know, my grandfather was quote unquote Santa for many of families, you know, for years.

And he gave so many people groceries and items, you know, on credit because that's all they had.

And when I look back on it, I see two things.

I see entrepreneur in that, and I also see a willingness to help everyone around you and.

Be humble enough not to remove yourself from the circumstances because you are successful.

And then I also saw that business fail because large companies like Kroger and you now have the Whole Foods and stuff, basically put the small mom and pop stores out of business.

And I actually always had a chip on my shoulder about that.

Like, how can I get my granddad's grocery store back one day, or, but I think it kind of like lit the entrepreneurial candle or fire in me, so to speak, was very privileged.

I, I ended up going to a high school.

That I was not supposed to go to, but I was granted a scholarship.

I saw wealth, you know, I saw people with a lot of money.

Those were my classmates, and it was my first time being challenged academically to a whole nother level.

You know, you had to have 70 hours of community service for every year of.

Every year of high school that you had been there in order to graduate.

Um, and it was just so many things and it showed me how wealthier people in my family actually lived.

You know, the only minority barely in that, in the high school class, I think it was four, you know, African Americans in a, in a graduating class of around a hundred.

So that basically got me used to being the only black person in many of the rooms that I would be in in the future, you know?

But I took that work ethic from high school and, and I remember the first year in, uh, college, they said, you know, your goal is not to get a degree here.

Only your goal is to get a degree, and your goal is to learn how to be an adult and communi.

And so after my first year, I would always go to my professors and say, Hey, can we make a deal?

If you give me my entire syllabus and I promise to get you all of this work back in three weeks, can I be allowed to skip class and only come and take the midterm if my grades require me to, or don't take the midterm and only come back and take the.

And 10 out of 10 of the professors would be like, you know, if you wanna take that risk and not learn this in the classroom, be my guess.

So I really didn't spend a lot of my time on campus.

I spent it traveling and pitching my first tech startup and going around the United States and traveling and going back to see my mom and see my little sister grow up while I was in college.

Definitely my last two years.

You know, that is an incredible story.

Yeah.

You know, so, so those are some of the small things.

And ultimately I graduated, I think it was top of the class in economics and, um, I spent maybe eight months, you know, at home trying to figure out what was next.

I ran a startup in Spain for a year.

Learned the language.

Just wanted to enjoy Europe and I gave everything up and I moved to Silicon Valley with the idea for startup I had, and I basically lived in a stranger's garage for 18 months and built my first company called Trainers Ball.

And I think that was, you know, a thing where you feel like you're on this path of greatness.

But I was homeless.

Not on the sidewalk homeless, but very.

Going to an unfamiliar place where I didn't know anyone and I had to open my mouth, make connections, and ask a stranger to provide shelter for me while I worked endlessly knowing that there was no turning back.

So I ran that business, built it.

It was a platform that helped personal trainers run their business, and we basically brought all their business online and helped them stream all their content and sell it.

And we focused on African American trainers in the south, and I kind of took my business acumen, built the website, educated them, people that were pretty much living in an areas where fitness was.

But the, the innovation around the business modeling wasn't there, just social media was there, so that company was really, really hard to build.

That was a seven year process.

I spent 18 months into Silicon Valley, and as that company was finally starting to turn a leaf and grow, I realized that the rules were not the same for black entrepreneur like me as they were for other individual.

Lo and behold, I ended up going around Asia for the next three years raising capital and it was so interesting because I thought, my God, being a, being this.

Young black male from Mississippi.

I am being better embraced in Asia across the Asian continent than I am in my own country, and I came back with a sense of pride.

I knew that I, I had not only survived and built a business in the United States, but I, I could build a business in Asia.

Why was it easier for me to go to Asia and have, be embraced and get support while trying to just do something good for.

Than it was in my own country.

I.

All parties involved, how individuals that look like me, how re treated one another as well as the, you know, the inherent system that has been constructed primarily by a white audience, you know?

And I said, something has to change.

And that's where the idea for a symbol came.

And I said, Hey, I'm gonna be that one person.

That makes the celebrities come to the table with a sense of humility and take the time to give back and teach and educate.

And I'm also gonna be the person to build celebrities out of the other successful individuals that are in our communities that are doing amazing things outside of media and enter.

We're gonna give them their flowers too.

And we have to socially re-engineer what success looks like in our community because if all you see is a basketball player, or his best friend or an entertainer and his best friend, being the catalyst to having wealth and money and providing for your family, you're gonna overindex in it as a group of individuals and we're gonna stay in the same pred.

That we are in

Courtney, what a story, because it's not only the things that you've done, it's who you've become in the process.

You know, it's been said that the only way you really know what you're capable of and how resilient you can be is to be put in a situation where you don't have a clue what to do next.

And you've got that multiple times.

Yeah.

You're clearly an encourager and that's an important point.

Have you ever hit a, a total?

I, I don't, don't say, have you ever, cuz I know you have a brick wall that was so unexpected, you weren't sure how to get around it over and.

So many, I mean, time, after time, after time.

So normally when, when things just get crazy.

I always sit very calm and still it's, it is like, you know, like the quiet before the storm when it just gets super quiet and you, you know, the lightning and the thunder's coming.

It just get quiet.

And I just think, and I just, my mind goes through every resource, every contact, you know, every asset that I have that could attack this problem.

And then ultimately in the, in, in the last minute, a solution.

Prevails.

Literally, you know, you just have to sit no matter how bad it is.

You just have to sit and you have to think, and I don't know if it's the dopamine, the adrenaline, but your mind would normally provide you with the solution because you have to tell yourself there's, you can't bail at this, you know?

Um, humility as well.

I've been in so many pickles and a lot of times people are embarrassed to ask.

These two things are normally what gets me out of a lot of jams.

You know, humility prevails if you just accept what you are doing and know that it's for a greater purpose.

You can be humble.

You can call a friend and pick up the phone and say, Hey, I need help.

You know, you don't have to worry about them saying, oh, well I thought you were in Mr.

Mba.

You were in business school and you are in tech.

It's like, yes, I won't, but I'm trying to start a company and that's very difficult.

You know, that takes a lot of different things.

So I'm humbly asking for.

And that's why I'm so happy.

Elon Musk always tells the story of selling PayPal and making a hundred million dollars and literally putting it all back into new companies and having to live on his friends apart on his couch for a year and a half because he had no liquidity or no money, because that is the reality.

So yes, when you come up and face a jam, If you haven't wronged anyone, you know, you can't call somebody that you've kinda screwed over you.

You maintain relationships.

You always add value to other individuals and you, you can be able to humbly ask for help.

That, that honestly is my advice.

Mm-hmm.

. Dan Moore: Now, let me ask you just kind of a different tack.

Do you have a morning routine that you start your day with on a regular basis, or does it vary from day to day?

No, for the most part it's, it's, it's pretty much the same.

You know, I, I, I wake up, I, you know, talk to my, my girlfriend and I hit the gym, and that's the first thing I do, I think for.

Maybe the last three years, I normally had a personal trainer come over just because that's something that I thought was important, my health and my fitness, and I'm too lazy sometimes to just get up and go.

So someone ringing my doorbell at 7:00 AM was just like knowing that I had that it, it helps me with decisions that I make late at night too.

You know, oh, are we gonna go out and have a drink or stay at this restaurant too late?

Or should I go home, go to sleep, because I know I gotta hit the gym at 7:00 AM So it's pretty much.

Wake up, hit the gym, read the Wall Street Journal.

Have a coffee, meditate on what I just read and start my work day.

Well, it's

a good, it's a great start.

You know, express an appreciation of somebody you care deeply for getting exercise going, get your brain moving.

That's a fantastic start.

And having that trainer outside, that's a master stroke.

I've got a very, very good friend that got me into walking years ago, which eventually led me into distance running.

And one morning we were supposed to meet at 5:00 AM and he didn't show.

And I waited outside his house until five.

Oh.

And the light turned on.

He stepped outside.

He looked at me and he said, you know what?

Peer pressure really sucks.

Let's go

. Cortney Woodruff: Exactly.

I bet he had a great session though, didn't he?

But it, but it works, you know, if we're accountable to somebody else, especially when you're paying that person, you're gonna use that time wisely.

You have to and, and, and you know, like we all think, oh, I know how to go to the gym and do it on my own, but.

You know, sometimes, at least with me, because of everything that I'm, I'm working on, you know, as a startup founder outside of work and, and just like my, my personal life, I, I really don't have the mental capacity to think a lot.

When I go to the gym, I'm like, Hey, you have this schedule.

You have, you know, the goals, you know the milestones of what we're trying to achieve.

You just tell me what to do because I don't wanna sit there like, okay, what do I do next?

I, I really have very limited capacity.

Apply critical thinking to things outside of work and just like, uh, you know, family issues and stuff like that.

Obviously my personal body is that, but like if there's an expert that knows more than me, why not?

Once again, humble myself and let them do what they're, what they're great at.

If, if you ever have a chance to play anything or train with the professional athlete, You can think you're in shape and then you just, everyone says that you see them go into another gear, right?

And you're like, oh, I understand why you're a professional athlete.

Like you just, you just took off, you know?

Or they doubled down.

And I actually correlate that to being greater in business.

The difference between the successful people and those that don't.

Is that within that, you know, five to 10 year journey, because it's going to always be that there's so many obstacles, there's so many decisions to be made.

There's so many highs and lows, right?

And a lot of people fail at the test of time because they don't have the resolve or the endurance to get through it.

And typically you think, oh my gosh, I've been on this 10 year marathon.

I'm tired.

You have to ask.

Now in the fourth quarter with two minutes left, what would Michael Jordan do?

What would Tom Brady do?

Or Tiger Woods?

They go to a whole nother gear.

You know, what do these people do in the clutch after they've, they're already tired.

It's like they start all over, like they haven't done anything.

They have more energy in the last few seconds than ever.

And in business, that's what you have to do.

Well, that's true, and I hope our listeners heard what you said very quickly, a few minutes.

That it's a five to 10 year process.

This is not a sprint.

This is not a run to the corner and be successful.

This is a long term game.

If you really wanna make a difference with people, I think that's awesome.

You know, it's one thing to work hard on a problem very long time, but it's another thing to be self-aware that you have to work on yourself.

And so oftentimes, We don't know what we don't know.

You know, it takes us all a long time to to seek out answers to questions, you know, questions that we have, but then also figure out the things that we never knew we needed answers to, and start seeking out the answers to those things as well.

So, yeah, , it, it, it's a journey because, you know, in life you're, you're constantly iterating on yourself as a person, picking and choosing what type of human being you ultimately wanna be.

Um, and then you also are trying to apply your viewpoint to whatever it is that you're working on.

Very true.

Courtney, I wonder if we could wrap up by asking you for some advice.

You know, we've got listeners from all different demographics, all different ages from high school students, all the way up to retirees and everything in between, and many of them are just living the dream.

The life is going really well.

We got some other listeners that are, are struggling right now.

Any words of encouragement for somebody that just doesn't know what to do next?

Yeah, so I think the first thing is pick your head up.

Hopefully you're always working on something where even if it doesn't work out the way you, you expected it to work out.

You can be proud of yourself a, for trying and whatever it is that you was working on at, at least you, you tried it.

And you could be happy even if you fell because it was for a great cause.

You know?

That's the first thing.

The second thing is to always realize that even when things don't work out, make a list of all the things that you learned and just ask yourself, am I a better person?

Am I better equipped, you know, for my next run at it?

Than I was when I first started this, because it probably will improve your chances of success or finding some type of relief with the next thing that you're working on.

And then I think to be more specific, you know, for those that may have their back against the wall with a pressing issue, one of the greatest ways that I found myself able to get help from individuals that, you know, I thought could have easily helped, it's I, I used the analogy of the alley who everyone's busy.

And when you go higher and higher up, the, the food chain people get really busy and you know, there's a million people calling them every day and everyone needs something and it's training.

The easiest way to get help from individuals of influence and means is to throw them Ali hoop.

So you have to do your homework.

You have to figure out what's their sweet spot, what they're great at, and why, what they're great at is beneficial to.

But why?

Whatever you're.

It's also beneficial to them.

And if you think about it that way, you pretty much can get your point across to them very easily and they should be able to understand it easily and it'll be an aha moment because you will have naturally figured out a way to incentivize them and they will go, oh, I'm incentivized by this.

This is easy.

All I have to do is pick up the phone and vo.

Because no one wants to do more hard work.

That's why they've at the top, they've been working hard for all their lives, you know?

So now they have the luxury of picking and choosing.

So oftentimes, yeah, no one really, you know, deals with the cold calls and wanna help outta the greatness of their heart.

Everybody's driven by, you know, normally capitalistic incentives, you know, or, or something, a play on their ego or, or, or just timing.

Right?

So throw people alley hoops and, and more than like, They are much more inclined to help you cuz you've already made it easy for them.

And that's my.

Yeah,

I think it's fantastic advice.

I love what you said about take a minute to count up what you've learned and what you've accomplished and and feel good about that, and take a moment to reassert who you are as a person.

And for those, our listeners maybe aren't familiar with an Ali loop, I guess I'd describe it as a spectacular assist to a spectacular scorer.

And it's not just a random bounce pass.

It is a spectacular toss in the air to the person that can handle it, and it works really well

and it makes them look good.

That's fantastic, Courtney.

Thank you.

Thank you so much for, for making your heart available to us as well as your mind.

We're glad you're in good shape, safe and sound and wanna encourage you to keep on the great work that you're doing cuz you are fundamentally an encourager and goodness.

Our world needs more of

those.

I appreciate it, man.