In this episode of the Billionaire Brain Trust series, host Steve Woodruff interviews Mike Houlihan, co‑founder of Barefoot Wines. Houlihan recounts how a $300,000 debt settlement for bulk wine in 1986 sparked the creation of the Barefoot brand, describing the early challenges of labeling, distribution, and regulatory compliance. He explains the company’s grassroots growth strategy—leveraging unconventional partnerships with Trader Joe’s, the U.S. military, and local community fundraisers—to build shelf presence without traditional advertising. Houlihan also details financial obstacles, such as difficulty securing loans and local resistance, and how creative fundraising (donating wine for neighborhood projects) accelerated national expansion. The conversation shifts to legacy preservation: Houlihan’s bestseller The Barefoot Spirit was transformed into a “business audio theater” audiobook, using Hollywood‑level production to dramatize entrepreneurial lessons for family offices and future generations. He cites a similar audio‑theater project, The Brain Savers, and argues that short, story‑driven audio segments help families convey values, preserve history, and inspire successors. Throughout, Houlihan emphasizes relatability, persistence, and the power of storytelling as a tool for both brand growth and intergenerational legacy.
Chapters
We wrote a book, became a New York Times bestseller. It's called The Barefoot Spirit. We went on speaking tours. We started speaking at universities and colleges throughout the world about business and about basically CPG, consumer product business. We're here to help the family offices have a new way. It's not the only way, but it's another way to convey and save and preserve their legacy. How did Grandpa put all these funds together? Where did this come from? You know, was he a coal miner? Did he make fences? What did he do? What was it like?
Welcome to Billionaire Brain Trust, our newest YouTube series that will take you behind the scenes into candid conversations with billionaires and those who work with them, hosted by Steve Woodruff, who brings a unique perspective as a family office advisor. Billionaire Brain Trust will feature exclusive interviews with billionaires and the key players in their organizations, offering viewers a rare glimpse into their stories, decision-making frameworks, and what they are excited about right now. Whether you're an aspiring entrepreneur, a seasoned investor, or simply curious about the world of the ultra-wealthy billionaire brain trust will help you think bigger and achieve more.
So we are in New York. We are at the Family Office Club, Single Family Office event, and very excited to meet Mike Houlihan. We met yesterday. Mike is the co-founder of Barefoot Wines, one of the most recognized brands in wine in the US, I'm sure.
Thanks, Steve.
And really excited to speak with you. We got, we got a chance to talk yesterday, but I think you have such a cool story.
Thank you.
And appreciate you talking with us. So would you mind telling us a little bit how— what's maybe the short version of how you guys got started? It's so fascinating.
Well, I think the caption for this is ignorance is bliss, right? So if I knew what I was getting into, I probably wouldn't have done it.
Yeah.
But, you know, you jump into the English Channel and you swim halfway across, you're not going to get tired. You swim back. Yeah. So long story short, Bonnie, who's my partner for 40 years, came to me after I'd only been with her for a year and she says, "I want you to go collect $300,000 from this winery that owes my client," who she was working for, "$300,000." And I went, "Wow, you know, $300,000. Okay, I'll go talk to 'em." So I go talk to 'em. They had declared bankruptcy that morning, you know, Chapter 11. So, you know, it was take it, wait your turn, hope you're not here for money. And I was already there. So I went through with the meeting anyway. I met with the board of directors and I was able to negotiate a settlement which involved bulk wine and bottling services instead of money. So now I had, instead of $300,000 worth of debt, I had $300,000 worth of wine that was bottled but didn't have a label. And I was thinking, okay, you gotta come up with a label, gotta come up with a marketing program, you know, gotta learn all the laws in all the states, you know, controlled substance, all this stuff. How hard could that be, right? How long could that take? Well, it took about 4 years before we really understood what the heck we were doing.
Okay.
And, you know, we made lots of mistakes, but we learned from our mistakes, that's for sure. And we took that little brand, they thought it was just a novelty, and it was really successful because we looked for other people that were doing wacky stuff, like Trader Joe's was doing wacky stuff at the time.
Yeah.
And nobody really wanted to do business with Trader Joe's, and we went, hey, you guys are wacky, we're wacky, let's do business together. And so as they expanded across the United States, they barefoot with them.
Oh, that's cool.
And so that helped us a lot. The other thing we did is we— see, we weren't from the wine industry, see. I mean, I thought wine industry was like, you know, swirl, sniff, you know, sip, say some words in French, right? Talk about midnotes. Forget it. It was all about distribution management. So the issue is, how do you get your consumer packaged goods to the store in Iowa and keep it on the shelf there, right? And that's a challenge because you got to go through distributors and truckers, and you got to pay all the taxes and everything else. But if it is off the shelf, it's not selling. If it's not selling, it gets discontinued. So that's when we realized, oh my gosh, we have to have an army of people who are out there going in all the stores every day just to make sure it's there. And that was the key to success because we weren't from the wine industry, so that we didn't think, oh, these wines are going to sell because they're so good, or they're gold medal winners. We said, this is gritty. We got to get in there. We got to muscle this thing, you know? Yeah.
So what year was that when you got the wine and started?
Well, we started in '86. Okay. By '95, we were in most of the states. And the other thing that helped us is we did a lot of business with the military, and the military is under the radar. They don't turn their sales into Nielsen. So the big boys, the big competition that wound up buying us out ultimately, yeah, didn't see us on their radar.
Okay.
So So that was the good news. The bad news was it was hard to get a loan because they—
The town would try to force you out, essentially, if they saw you coming up. Of course they would. Okay.
Yeah. They nicknamed us the brand that would not die. So anyway, we did all that and wound up— we couldn't afford advertising, so I get a call from a guy in Chinatown, San Francisco, and he says, "I need $50,000 for a kids' after-school park." And I said, You sure you got the right number, pal? And he said, yeah, you know, you're Michael Houlihan, you're a rich winemaker in Sonoma County. I said, look, I don't have any money. I said, I got wine I can't sell. I'll give you wine, you can use it. You know, you can auction some off and buy some swings or, you know, sandboxes, slides, or you can use it at your fundraiser. Maybe people will loosen up and write you a bigger check. And he took the wine. He wanted the money. He was very disappointed. But sales took off in his neighborhood. We started to notice that. We said, "Wow, let's try this with another fundraiser." So we tried it with another fundraiser, another one, and that's how we built Barefoot across the United States. Instead of using commercial advertising, we went to worthy causes that were in the neighborhoods of the stores that were carrying our products in the hopes that their nonprofit members would have a social reason to buy our product. Because then they would become advocates and they would share it with their brothers, sisters, employees, everybody.
So that's such a good strategy.
That's, that's our story. We wrote a book, became a New York Times bestseller. It's called The Barefoot Spirit. We went on speaking tours. We started speaking at universities and colleges throughout the world and about business and about basically CPG, consumer product business, and In the process, we noticed that people started coming in wearing earbuds about 2016. By 2018, everybody was wearing earbuds. And we went, what is going on? This is a revolution. You know, Bonnie said, you know, we better find out what those young people are listening to. So we said, what is it? Is it hip-hop? Is it rock? You know, a typical boomer question, right? And the young guy says, no, no, I'm listening to podcasts. You know, they're free. I'm learning about my business. I'm learning how to improve my life. And another gal says, "Oh, I'm listening to War and Peace. You know, the damn thing's so thick, I can't sit still for it." And we thought, sit still for it? She's talking about mobile on demand. This is a great way to get a message across. So we took our book, which was already written as an adventure story, and we turned it into what we call business audio theater, which is kind of a 1945 radio approach. Before television, when actors acted parts to sound effects and music, and you were like right there. You were the fly on the wall. And it was so successful, it was—
So that's what you did to your book. So if we get your audiobook—
You can get our audiobook. You can get it any place that sells audiobooks.
And it'll be like radio theater.
It'll be radio theater. And you'll enjoy it. Yeah, that's fun. And I'd love to hear from you about what you think about this new approach.
Yeah, I'll check it out for sure.
So then we got approached by— the guy that really was the first person to do interstate enterprise telemedicine, and he's a neurologist. And so he wanted to do it because he wanted to tell his story to other people in neurology. He wanted to use it for teaching and whatnot. So we did it for him, and that was voted top 20 business books in the world last year. So we're pretty excited about that. So that one is called The Brain Savers. You can also find that in audio Theater, we call it, but it's in all the Audiobooks stores. But there, that's— yeah, that's pretty much where I came from, what I'm doing, and where I'm going.
Yeah, I could— I could see a lot of— my kids ask me to tell them a story all the time. I know we talked about this briefly, that this could also be used for families to really share their story.
That's— and yeah, that's why we're here. We're here to help the family offices have a new way. It's not the only way, but it's another way to convey and save and preserve their legacy. How did Grandpa put all these funds together? Where did this come from? You know, was he a coal miner? Did he make fences? What did he do? What was it like, you know, in his garage when he got started? And so it kind of humbles things down to a real believable human level where you say, look at this guy, you know, he's scared, I'd be scared. He doesn't have any money, I don't have any money. This guy's, you know, got a lot of chutzpah. Approachable. Look at this guy.
Relatable.
Yeah.
When you hear the early stories of what it takes to get there.
Yeah, the idea is instead of somebody telling you what their values are, you can actually be entertained by listening to and imagining in your mind's eye what this person is going through, you're experiencing it. And so it's much easier for you to identify with their values because you see them wrestling with decisions and holding up their own principles on the one hand and, you know, what's the smart thing to do on the other, making that decision. So we love doing it.
It's easy to say that someone was hardworking or they had integrity, but when you tell story after story that shows that this was a brutally tough time and they just kept being persistent over and over again, despite all odds, those, those are the stories that really sink in for all of us, right? But especially true when you're, when you're trying to share it with your kids and next generations. And the fact that it's recorded and the grandkids and the great-grandkids can still have access to it is pretty cool.
That's the idea, Steve. You know, you do it once, it's there for 100 years. Yeah. And the thing is, we have a complete operation in Hollywood. We have engineers from Disney Disney, we, we do a really first-class job. So when you listen to these stories, you're going to be entertained, and they're in short segments, so you don't have to sit there for 5 or 7 hours, but you can listen to like one segment and go, oh, you know, this is how the guy got started, or, you know, this is where she ran into her first challenge, or this is how she hired her best person. And so those kinds of developments that happen in the life of any business you'll be able to observe and appreciate, and hopefully you'll be able to emulate some of those values that you see dramatized in those scenes.
Yeah, so cool. Thank you. We'll post in the show notes some, some more info. I love it. This is a pleasure, Mike. We really appreciate the time.
Thank you very much, Steve. It's been a pleasure. Thanks.
