How to break through a fear of failure

JEFF BERMAN:  Hey folks, Jeff Berman here. We were so lucky to have the brilliant CNN host and entrepreneur, my friend Van Jones, join us at the 2025 Masters of Scale Summit to lead some of the most spirited and inspired and engaging conversations we’ve had on our stage. In the episode we’re sharing today, Van speaks with Fawn Weaver, who is an absolute force of nature. She’s the founder of Uncle Nearest Premium Whiskey. After blitzscaling one of the fastest growing spirit brands in history and becoming the first Black woman ever to build a billion-dollar spirits business from the ground up, Fawn talks with Van about why her focus is not just on building a company, but building an extraordinary life. You’re going to love this one.

FAWN WEAVER:  Hello, hello, hello.

VAN JONES:  You’re so well-known now. What you’ve done is so extraordinary, starting this brand literally from scratch based on a story that nobody knew. We’ll get to that. But those of us who are massive fans, we would know you better if we knew what?

WEAVER:  I always show up as me, never as a representative of myself. So the reason I reach people is because they’re talking to the real me at all times. I have up no walls.

Copy LinkUncovering the story of Uncle Nearest

JONES:  I love that. I love that. Well, some people may not know this story. How many people here have heard of Jack Daniel’s? Okay. How many people know that he stole all his stuff?

WEAVER:  You better quit that. And you should not have raised your hand. That is absolutely not true.

JONES:  Okay. So tell us the story of Uncle Nearest just so they know.

WEAVER:  So to be clear, since Van decided to go back to the original story, in 2016, in June of 2016, there was an article in the New York Times, and it was a photo of Jack Daniel sitting with an African American man seated to the right of him. The reason why that was important is it was circa 1904, and the photo was Jack Daniel and his leadership team. At that time, any African American in a photo would be seen on the periphery if they were allowed in the photo at all.

JONES:  At all. At all.

WEAVER:  And in this photo, you had the African American man to the immediate right. And once you actually look at the full photo that is not cropped, what you will discover is Jack Daniels off center. The center position was given to the African American man. So the question becomes, why would Jack step out of the center position of the photo and give it to an African American man? And you have to look at yourself here in Lynchburg, Tennessee. You’ve got a photographer who undoubtedly has never seen this before, understand this. And so I’m looking at this. The world came to the conclusion because the headline was “Jack Daniel’s Embraces a Hidden Ingredient: Help From a Slave.” The entire world very quickly determined Jack Daniel was a slave owner, stole the recipe, hid the slave. I looked at the photo and said, “If you want to hide an enslaved man or his children, what you don’t do is put him as the center of a photograph.”

And so I looked at this and came to a conclusion pretty quickly, that it was very possible that Jack Daniel was our first business ally. And if that was the true story, then I knew to be able to share that with America who has an underbelly of race we haven’t dealt with, the entire world knows our underbelly is race. You poke us there, and we will react every single time. And so I knew that if I was going to inject an African American into the story of Jack Daniel’s Distillery, who we now know Nearest Green is Jack’s first master distiller, he was the only known master distiller for No. 7.  For those of you who do not know, Old No. 7 was actually Jack’s original distillery number, and Nearest Green is the only known master distiller of that distillery.

JONES:  The reason why I love talking with you and learning from you, most people would say, “That’s interesting.” They wouldn’t say that’s the key to a billion-dollar brand.

WEAVER:  Yeah. I didn’t say that either. I said, “This is going to be one hell of a book and one hell of a movie.” So the book Love and Whiskey tells the story of how this all unfolded. I didn’t show up in Lynchburg for a whiskey. I showed up in Lynchburg –

JONES:  Because the story.

WEAVER: Because I knew it would be a brilliant book that could then be turned into a movie. So even when I showed up there, I was already a New York Times bestselling author. This would be my third book, and I had no doubt that it would be an amazing story if what I believed to be true was true. If this was a story in which Jack Daniel stole the recipe from an African American man or an enslaved man, I wouldn’t have been interested in that story because we have so many of those. What drew me to this story was the allyship.

JONES:  The love.

WEAVER: The love, the honor, the respect. The most famous American whiskey maker of all time moving out of the center position. So when America tried, at some point, someone here would attempt to wipe out the legacy of Nearest Green, which they tried in 1978, which is why no one of this generation knew the story. When Jack was alive, when his descendants ran the distillery all the way till the last one passed away in ’78, Nearest Green and his boys, George and Eli were always a part of the story of Jack Daniel.

Copy LinkWhy Fawn Weaver refuses to be a mentor

JONES:  Yeah. The reason that people are here and people are so fascinated by you is that from the beginning, this is an unlikely story, and for some reason you’ve been able to break the playbook. You have not done a single thing in the playbook. You even said that you don’t care about the P&L as much as you care about the love.  And you got people here who are trying to build companies. They may have a story written on their heart that their advisor told them, “Oh, don’t say that. Don’t lead with that. Here’s a cookie cutter for this. Here’s the way you do that.” You’ve broken all those rules and you’ve broken through. Just talk about that as a founder.

WEAVER:  I think the key is this isn’t a new blueprint. You can go back to Carnegie, you could go back to Rockefeller. There are certain elements in every American titan that you can find in this story. What I think a lot of people do, and I think it’s a big mistake at the current moment, I have so many people come to me and say, “Will you mentor me? ” And every time I say, “No.”

JONES:  Why not?

WEAVER:  “But I’ll send you a list of books.” Because I believe it’s a crutch. We’re looking for someone to guide us, but the reality is everyone still living is still looking to be guided in some area. So if you are incredibly successful in business, but your marriage was garbage, and your kids didn’t like you by the time you died, I don’t want you to mentor me. Right? And so what I have done throughout 30 – listen –

JONES:  It’s about to get real.

WEAVER:  What I have done throughout my 30 years of entrepreneurship is I have read most books on most titans, and I can tell you what they did. So when I’m looking at any situation that comes up in my company, I don’t care how difficult and challenging and crazy it looks to the outside world, I assure you I’ve already seen this playbook before. I saw it with Reginald Lewis when he leveraged everything for Beatrice.

JONES:  The first Black billionaire in America.

WEAVER:  The first Black billionaire when he leveraged everything for Beatrice. I saw it with Carnegie when he’s building using a material that wasn’t safe as far as Americans were concerned. And yet he had to get them to cross a bridge that he had built that was very expensive, that ran two years behind budget in which every investor was knocking on his door and every debt collector, and he had a lot of them, was calling him every single day for two years trying to shut him down. And he’s building something that America never even said they wanted. He builds this bridge and to convince America to cross the bridge because Americans for whatever reason believe that elephants would not walk on anything that wasn’t stable, he does a whole PR move to have the elephant lead the people across the bridge. Do you know how brilliant that is of the PR move? But let me tell you who was one of the most brilliant PR people in the history of American business, Jack Daniel.

And so when I am looking at what I am doing, I don’t look at anything that I am doing as unique. You could call out any element of my business, and I can point you to who it is that I am following in that regard. But here’s the key to doing it this way. And listen, for all of you all who are looking for mentors, go for it. Just make sure their personal life is together because if their personal life ain’t together, you don’t want that one.

BERMAN:  Still ahead, more from Van Jones’ conversation with Fawn Weaver.

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Copy LinkBalancing success in business and personal life

WEAVER:  When I am looking at the blueprints that I am following, I could probably point to 20 different ones that are certain elements, none of them in the spirit business.

JONES:  Gotcha.

WEAVER:  Because no one, no person of color or woman had ever succeeded before me in the spirit business. So I can’t follow your advice.

JONES:  That’s right. That’s right.

WEAVER:  I can’t follow what you did, but what I can do is I can look to someone who started with nothing.

JONES:  That’s the thing.

WEAVER:  And then I can watch what they did. And then after they’re dead, I’ll know whether or not their family liked them and then I can decide what elements – y’all, I’m serious about this. I don’t want to just have –

JONES: Family matters.

WEAVER: – a great business.

JONES:  Why is that so important to you? Because look, I have a bunch of questions here about business and you’re talking about family.

WEAVER:  Listen, I’ve been married 22 years to my favorite person in the world. My favorite person. It’s important to me because I think that people give up so much of themselves to build. But we weren’t placed on earth to build. We were placed on earth to love. And if the building supersedes the love, you are going to walk around empty, and that’s why I show up as me and not a rep of myself. I can do that because I am so loved. I don’t care about what anybody in here thinks. Not that y’all aren’t important. You just ain’t as important as my husband’s words.

JONES:  Yeah. I’m rarely speechless.

WEAVER:  That’s what Jeff said when he interviewed me.

Copy LinkOvercoming fear of failure and public embarrassment

JONES:  I do this for a living. I’m rarely speechless. But let’s talk about this now because let’s be honest, we have a bunch of people who are building companies, who are building businesses, and that’s how they think they’re going to make a difference. That’s how they’re going to vindicate having been bullied and pushed around and given wedgies on the playground. That’s how they’re going to show everybody who laughed at them. And it has become a singular pursuit. And in the world of technology, that means that we are going to wind up with the world possibly with an awful lot of data and very little wisdom.

WEAVER:  Yes.

JONES:  And we’re already now running companies that are data smart and people stupid.

WEAVER:  Yes.

JONES:  And it has to do with a hole in the heart of these founders too often, too often. And yet I can imagine somebody saying, “Well, listen, easy for you to say, you had another career before you became a builder. You have this broad basis of understanding of all these stories if you’ve ingested in your own personal LLM, and you’re now with a billion-dollar company.  But I’m 23 years old or 32 years old and I’m trying, and I don’t have nobody that loves me like that. And if I spend time trying to find that love, I’m going to miss my moment.” What do you say to that person?

WEAVER:  I wasn’t trying to find love. Love found me. I started my first company at 18.

JONES:  Okay. Oh, okay.

WEAVER:  So when my husband found me, I was already building. But I was open, right? And so for so many people in the building, they begin to close themselves off because they are so concerned. For those of you who do not know, if you buy any alcohol, it’s essentially, for the most part, seven spirit conglomerates, right? Six really, and then toss in Tito’s because he’s bigger than all of them, even though he has one bottle of vodka, right?

But that is 90%, more than 90% of the volume of alcohol in this country is run by a very small group of people. Then you have this little Black girl with all the fricking confidence in the world who walks in here and says, “I don’t know what I’m doing, but I will figure it out. And by the time I’m done, I will be sitting right beside each of you, and I’ll be running as much through here as you are.” But let me explain the reason I’m able to do this is because I don’t care what arrows they throw my way, I won’t let it close me. I remain open.

And that’s a tough thing because people are so afraid of being hurt, people are so afraid of other people seeing your failure. I said this not too long ago, and people really questioned this on social media, but I’m pretty sure I got the data to back this up. People believe that they have a fear of failure, and it’s the reason why a lot of people never launch or a lot of people refuse to scale. They’ll stay at a certain level because they’re like, “If I go to the next level, and I fail,” so they’ll just stay stuck, and they believe that their fear is failure. But I don’t believe that is what the fear is because if you try something and it doesn’t work, but you were the only person who knew you tried it and it didn’t work, do you care? It’s not really a fear of failure, it’s a fear of public embarrassment, of people knowing that you failed.

JONES:  And that shame button.

WEAVER:  I don’t care.

JONES:  You don’t care.

WEAVER:  Because if I fail, I’ll build it again. It’s of no consequence to me.

JONES:  Well, look, it’s so interesting sitting here with somebody who is free.

WEAVER:  Yeah. You don’t get that a lot, do you?

JONES:  I don’t.

WEAVER:  Yeah. Yeah.

JONES:  I don’t. You’re free. And I think that that’s something that we don’t talk about enough. I worked with Prince for six years. He was free.

WEAVER:  Yes.

JONES:  He had some painkiller addiction he picked up late in life, and it killed him, but he was free. And I have not met anybody who felt as free as Prince felt until I’m sitting here with you.

WEAVER:  Wow.

JONES:  I wish he could be up here. It’s a remarkable physical experience to be with somebody who is not guarding anything and who’s not managing a bunch of ego or fear or presentation who is just flowing. None of these questions are going to get an answer. I’m sorry, y’all.

WEAVER:  Let me tell you it’s so funny because when my company is going through anything publicly, anything challenging and people will check in with me, and they’ll text and they’re like, “Are you good?” And what I’ll do is I’ll send them a screenshot of my stress levels on Oura. Do y’all have an Oura ring? So I live between restored and engaged. And so after this, I’ll look at my Oura ring at the end of the day, and I assure you I’m going to still be between restored, relaxed, and engaged while sitting here, leading up to here when I leave out of here –

JONES:  Lower handlebars.

WEAVER: – and I believe it is because I show up as me.

JONES:  Yes, you do.

WEAVER:  I don’t have a fear of public embarrassment. And you have to, by the way, be embarrassed publicly a few times to know whether or not that statement is true.

JONES:  Yeah. Well, I know nothing about that, but go ahead.

WEAVER:  But I do believe that a lot of people, when we’re talking about Masters of Scale, a lot of people choose not to scale because they’re afraid of failure on the next level. And the reality is any person who has built anything extraordinary, any extraordinary business, especially in America, they always did it on risk. They always did it not knowing what happened on the next level.

Copy LinkThe secret weapon of love and faith in business

JONES:  Listen, I agree with you on that, but I just want to say something to you because anybody could say that part, take risks. But what you’ve revealed here is there’s a secret power that we don’t talk about, which is the power of love.

WEAVER:  Yes.

JONES:  Self-love.

WEAVER:  Yes.

JONES:  And then being open to love from others. Everybody may not find their 22-year love of life, but you said something about being open. This is a tough game. You get a lot of no’s. You get a lot of rejection. You get a lot of people who you’re trying to tell them what your dream is, and they’re just blinking at you.

WEAVER:  Yeah.

JONES:  And you got to go to the restroom and get your face right.

WEAVER:  Well, see, I don’t.

JONES:  And that’s what I want you to close on is somehow they need to add in these business books and add in all these courses everybody spent all this money on, a chapter about love and staying open. Talk about not just the fact of it, but what does it give you? What does it unlock for you to have this secret weapon of love for self and others in your business?

WEAVER:  Yeah. So I don’t separate business from personal. I have no separation. I am who I am at all times. I don’t care if I have on no makeup and I’m in sweats and I’m at home or if I’m here with you. This is the same as if you were at my house, now if you were at my house, I’d have on no makeup and I’d have on sweats, but the exchange would be the same.

JONES:  That’s okay.

WEAVER:  It is no different for me. But because of that, anyone who knows me knows I lead with my faith. I absolutely lead with my faith. So the reason why when people say no or when people, if their heart is turned away, if I am looking for something and they choose not to invest or whatever the case may be, I don’t look at it as being that person. And I’ll explain what I mean.

When Moses was leading the people of Israel out of Egypt, we’ve all seen all the plagues that happened to Pharaoh because he kept saying, “No,” right? We’ve all seen this. This is the part that people miss, and I live with this in front of me. Every single time Moses said, “Let my people go,” Pharaoh said, “Yes,” and he let the Israelites go. The next sentence in the Bible, every single time, “And the Lord hardened Pharaoh’s heart, and he did not let the Israelites go.” So whenever someone says, “No,” to me, I assume it’s God, not that person. So I can remain open because that person was only speaking on behalf of the direction God wanted me to go in. So I’m okay with every no.

JONES:  Fawn, I’ve interviewed Oprah. I’ve interviewed Jay-Z. This was unbelievable.

BERMAN:  Thanks again to Fawn Weaver and Van Jones for joining us. This conversation was recorded live on stage at the Presidio Theater in San Francisco at the Masters of Scale Summit.