Daymond John, a 2024 Real Leaders Top Keynote Speaker, zeros in on what it takes to lure investors and be more intentional as a social impact company.

By Carla Kalogeridis

If you have even one good business idea in your head, you’ve probably fantasized about pitching it to Daymond John. What would you say if you had 3 minutes alone with Shark Tank’s branding and marketing guru?

Well, I didn’t get 3 minutes with Daymond John — I got over 30. And while I didn’t pitch anything, I made the most of my time with a broad swath of questions to capture the best of America’s favorite entrepreneur. John opened up about the big shift in the second half of his career, why he’s not leaving his kids any money, and much more. 

Real Leaders: Our readers are impact company leaders, founders, entrepreneurs — that’s our sweet spot. So, I wanted to start with your experience in hearing and making pitches. What are the most important qualities you look for in a founder or entrepreneur in order for you to make an investment?

John: First of all, can they articulate the story to get my attention? Because that’s the human interaction aspect of it. What are you talking about, and why would I care? Are you educating me that this is a problem, or are you assuming that I should just know about it? 

Then I ask myself: Is this person a rock star? Do I want to know this person? Is there a need for me to be in this business with this person? If the founder is a rock star, then whether this business works out or not, we’re going to do something else together. I hope your thing is baked. I really do. But guess what, if it fails, alright, you’ll work with me, and we’ll do something else. At the end of the day, that’s what it is.

RL: What are the mistakes people make when they pitch investors — the things that make you cringe?

John: Not studying the investment target. Why would you want me as a partner? Do you know what’s in it for me? Some people come to Shark Tank, and they think because I have a successful clothing company, I should invest in their clothing idea. Well, if you really knew me, you’d know those are the only companies I don’t want to invest in because I have too many clothing companies. I need to diversify my portfolio.

RL: How have your own investment criteria changed over time? What’s that journey been like for you?

John: Originally, it was, “I don’t have any money,” so I had to concentrate on what I could do. Then it was, “I have money and I want to invest in sectors I know.” But I made a lot of mistakes in those sectors because I thought money was the solution without putting in the work and doing my homework. Then I moved to being in various sectors. I’d throw money at it, and I was right in the middle trying to learn on the fly. I’m throwing a lot of money at it, and I’m trying to tweak it to find better ways to be more effective.

But what I’m doing now is purely about the people. I have to see where I truly add value. I have to have a passion for it. And I have to really trust that the founder has a massive amount of information in the industry. 

RL: What role has social entrepreneurship played in your life?

John: It’s huge. My biggest, most successful investment on Shark Tank is Bombas socks (a 2023 Real Leaders Top Impact Company), which is about social. I care about what I do. All my investments have some kind of social driver to it. FUBU may not have been a nonprofit and the messaging wasn’t social, as in let’s make a better planet or something of that nature, but it was about one culture empowering another culture. Then I move on to Shark Tank, which is about investment empowering other people. My books and everything else I do now are about empowering people. So it’s critical.

The first half of my career, from an investment standpoint, the social aspect wasn’t a big topic. But now, with the success of Bombas, I’ve learned that it’s critical to have that component. Customers want to stand for something, and it has to be genuine. I’ve had some experiences with companies wanting me to be the face of their brand, and I saw that social impact was not their driving force, and they were not being honest with their intentions.

RL: When you look at the investment landscape and how that might impact business leaders, what are some of the market disruptions you’re seeing?

John: Well, AI is the common one everyone is talking about. But I want to give you some meat on the bones. AI is the market assumption, but it’s the use of AI analysis that will cause disruption. AI is such a big conversation. It’s in everything in a big way. Think about your newsletters. With AI, maybe you can go from a copywriting and social team of 20 down to five. People think that AI is going to replace those people, but maybe there will be other jobs created as a result of AI. We just don’t know what they are yet.

The big thing all CEOs are struggling with is how to get effective work from people, how to deal with remote and semi-remote and virtual, fragmented teams. This virtual, remote, fragmented way of the world working is not working. 

RL: You’ve done a lot of motivational speaking. What makes a great speech and a great speaker, and what are you still trying to improve in your own speaking?

John: A great speaker is self-aware. This is extremely important because they’re not making any more attention in this world, and captivating people in the beginning and keeping their attention is very hard. Maybe you can captivate somebody for the first 10 minutes, but then you lose them after 20 minutes. So how do you pack in what you need to say in 20 minutes? How do you relate to them, feel equal to them even though you’re the one on stage who is deemed as somebody with this greatness or special information?

It’s all in your presentation of the message and how you make people feel. Do you make them feel like they’re connecting because you’ve had the same struggle? And you’re both, at the end of the day, arriving at the same solution or inspiration. 

A great speaker has a takeaway action that somebody is motivated to do at home. I mean, even if you had the person in tears, what is the takeaway? It’s always got to be about what’s in it for them. And of course, last but not least, are you in tune with what the client needs? The person or group who asked you to speak — what do they want? The client has a vested interest in your talk. Everything is on the line for them. Some speakers take up the stage with their own priorities, and if you act like that, then you let people down.

RL: Do you like public speaking?

John: Oh, I love it. I absolutely love it. I love that we find a way to connect through the conversation and the struggle.

RL: What are some of the most valuable life lessons that have profoundly made a difference in your thinking and actions?

John: You have to be extremely hard on yourself in striving for knowledge and constantly tweaking yourself to be better. But at some point, if you have put in the time, then you also have to take a moment to smell the roses. Be proud of yourself. You have to really take inventory of yourself.

You know, the three pillars to success are pretty simple: You got to know your why, you got to set goals, and then you got to do your homework. If your why is the why your parents told you, then that’s what success looks like to you. Do you want to belong to a bunch of people you don’t know who will never change your life? Then you’re setting the wrong goals and you’re going to do the wrong homework to get to those wrong goals. Being brutally honest is a really big key to success.

RL: Many of our readers are the heads of family businesses, and they’re working on succession planning. You have said that you’re not going to leave your daughters any money, citing the importance of a legacy versus an inheritance. Can you talk a little bit more about that?

John: The percentage of generational wealth that gets passed through to children and grandchildren is not that great. It’s been said that the first generation makes the money, the second generation enjoys it, and the third destroys it. I’m not going to say the third destroys it, but in only a small percentage of businesses do the second and third generations take the business to another level or expand it significantly. Now, does that money stay there in the family? Absolutely. Do the Rockefellers still have their money? Of course, and their foundation still does great things for this country. But are the children running their own businesses or extending what the family has? Not as much as probably people would think.

So that brings us to inheritance versus legacy. The thing that any parent wants to do is give their children the things that they themselves never had access to — whether it’s education, freedom, whatever the case is. But when you give your child everything, you make them the poorest person in the world.

I started off letting my girls know I would not leave them anything. And I did that for various reasons. Number one, someone might come into their life to use them for something that was not best for them. I want them also not thinking there is going to be a pot for them at the end of the rainbow. They need to work hard for themselves. They must become really great people to society.

I’ve been to many funerals, but I have never been to one where they talk about what somebody had, their possessions. I only heard of how they made people feel and how they impacted people’s lives. If my legacy is that my children can say, “My father was an everyday man who tried to empower people,” then I think that example will open way more doors for them. I don’t want the door open because they got money hidden behind that door.

RL: You once said that anything worth doing is worth overdoing. What is your passion these days? What are you overdoing right now?

John: My passion is giving access to people who deserve it — but not just giving access — also, showing them they already have access. The one thing people don’t realize is access is all around us — it’s the use of access that is not utilized. As connected as we are, I truly feel like we are at the dumbest goddamn time in history because people hit the top link on Google and then wonder why what they’re asking for does not work. They say all they get is “no.”’ They say, “I did this and then didn’t get that.” Did you pick up the phone? No? Pick up the damn phone. It’s pretty simple, right? I just don’t get it.

I am not about giving access to people who get stuck on these little devices that they’re not going to be further than 3 feet away from for the next 97% of their lives. I give access to a CEO who says, “Listen, I’m somebody who nobody knows, but I’m doing a lot of great work out there, and I want to be the voice of authority.” Or I will give access to a kid who has no financial intelligence. I want all our children to have financial intelligence. It’s not about having my own personal Shark Tank. It’s about giving access to the people or foundations who are going to use it for the right reason. That’s my passion.

Somebody told me something the other day: “The first half of your life, you do it for your ego. The second half, you do it for your soul.” If I think that you’re going to do something to make the world a better place — no matter where you are in life — I’m going to give you access by showing you how to utilize the access that you have.

RL: Now that’s a legacy.

John: Well, hopefully, the windfall is that I’ve inspired people of more colors to say, “Whatever my culture, my beliefs, I can work within my community and empower people.” No matter what side of the table you’re on, you can create investments or ways that people can have a synergistic relationship with those outside America. This is the American dream that’s been given to us, that corporate America doesn’t care about your color, your creed, your gender. And look at me — if I can do it, you can do it.

But our education system is broken. We’re still going off of an 80-year-old system that teaches kids shop and how to build things, but it doesn’t teach them financial intelligence — and that’s one of the few needs we all have in common. A lot of people don’t know if they want a formal education, but they don’t have financial intelligence starting off as children, and then they get marketed by predatory companies at 16 or 17 years old, and they end up with a $700,000 debt for a college education that they were not even certain they wanted.

I do believe in higher education. But the data shows that 57% of the kids graduating now will retire with a job title that doesn’t exist today. It’s like telling somebody 20 years ago, “You’re going to be an AI expert or a social media expert.” So you have no financial intelligence, but you do have $700,000 worth of student debt that you’re not going to pay off until your 50s for a career that you didn’t even know if you wanted. What does that do to our country?

Here’s what it does: All of a sudden, it’s expensive to eat clean. So what happens? Well, you start having a bad diet because the cheapest thing to consume in our country is made of butter, sugar, and salt. Domestic violence rises and incarceration rates rise because if you don’t have an education or you cannot afford enough, what are you going to do? It is a big problem, and it can easily be adjusted if we give our children financial intelligence. We don’t need them starting off with 18% on their credit cards and student loans, with careers they don’t want to have so they can buy a whole bunch of stuff they’ll never need.

RL: Anything you want to say specifically to our readers who are trying to use business as a force for good?

John: I think they need to be more intentional about what they’re doing. We always hear there are so many absolutely amazing leaders and corporate citizens who are doing great things, but they feel dirty about trying to say and show what they’re doing because it feels like they’re trying to make a profit off of doing good. 

When George Floyd was killed, a lot of my friends and business associates called me for advice. They felt compelled to do something. I was honest with them. Even though I’m African American, and I want to steer all the help I can to the African American community, I advised them not to take any action just because it’s the trendy thing to do. If your action isn’t coming from a genuine place, the community — be it the African Americans, LGBTQ+, veterans, whoever — will recognize that, and it could end up hurting you and your brand. As they say, real recognizes real.  

If you want to be authentic, start by talking to the people closest to you — your staff, your friends, your colleagues, or business partners. Many of your people have been a part of these communities for years and you may not even know it. That’s a bloodline through which you can take very intentional steps.

People like to be associated with good causes. If you can give them a way to do it, they will talk about it. That’s user-generated content. That’s why Bombas has worked so well. People want to do good and brag about it. Yes, they’re great socks, but they’re just socks. When I did the deal, they were doing 700,000, and they will do 1.4 billion this year. When I did the deal, I had a million dollars’ worth of socks in my warehouse that I couldn’t sell. The only way I sold them is that I was sneaking into your laundry room at night and taking one out of your basket.

RL: I know that’s true.

John: People buy Bombas because they want to brag that they are giving back. If you have a business that’s also doing good, now you save them from having to go and intentionally give because they buy from you and will tell your story for you.

I will tell you a story. My daughter worked at a pizza parlor. She says, “Daddy, I gave 20 times this year. Every time I bought this, I helped clean up the ocean. Every time I bought this, I stopped human trafficking, and every time I bought a pair of socks, a pair of socks went to one of the homeless shelters. And by the way, Daddy, I’m going to buy every person I know socks for Christmas so they can help 10 other people.” That’s an example of why you have to be very intentional about what you’re doing because people want to brag about what you’re doing and what they’re doing. You can be a force for good — and your customers will help you.