Bourbon, badass women, and a bold new brand shaking up the spirits industry? Now that’s my kind of conversation! Especially during Women’s History Month.
On The Debbie Nigro Show, I had the pleasure of chatting with Molly Kingston, the trailblazing founder of Oakley Bourbon—a woman-led brand making serious waves in a traditionally male-dominated industry. And trust me, this story is as smooth and strong as the bourbon itself!
A Spirit with Spirit: Inspired by Annie Oakley
Molly’s inspiration? None other than the legendary Annie Oakley—the sharpshooter and symbol of female empowerment. Just like Annie, Molly had the nerve (and the guts!) to disrupt an industry that didn’t see her coming. She invested in rare bourbon barrels, studied the business, and noticed something missing—a bourbon brand that truly spoke to women.
Enter Oakley Bourbon—the world’s first and only bourbon to launch with a 20-year-old edition. Yep, you read that right. Thousand-dollar bottles sold out in minutes, and collectors are lining up for more.
Why Bourbon? Why Now?
Women are making their mark in whiskey, and Molly saw an opportunity to create a brand that felt inclusive, stylish, and bold—just like the women who drink it. Oakley Bourbon is all about strength, independence, and community—values that Annie Oakley herself would have raised a glass to.
And speaking of collectors, Oakley is the first spirits brand to use Solana Blockchain anti-fraud technology on its bottles—ensuring authenticity for decades. This high-tech touch has serious whiskey enthusiasts clamoring to get their hands on a bottle.
More Than Just a Drink—It’s a Lifestyle
Molly isn’t just selling bourbon—she’s building a movement. From limited-edition collector bottles to exclusive Royale playing cards that unlock VIP experiences, Oakley Bourbon is about bringing people together over a glass of something truly special.
And let’s talk about that bottle—designed with women in mind. No clunky, hard-to-hold packaging here. Oakley Bourbon’s bottle is elegant, sleek, and made for a woman’s grip—but don’t worry, gentlemen, you’re invited to the party too!
What’s Next for Oakley?
With Collector’s Edition 2 on the way and a special summer release in the works, Oakley Bourbon is just getting started. And if Molly Kingston’s track record is any indication, the best is yet to come.
So grab your fringe jacket, cowboy hat, and a glass of Oakley Bourbon—because this is one brand that’s ready to ride into the future.
Want to learn more? Head to OakleySpirits.com and get in on the action.
And to Molly—cheers to you, your vision, and the women raising a glass to history!
Oakley Bourbon: A perfect choice to toast to all the women who disrupt and innovate.
P.S. Obviously Molly agrees with my mantra …”Risk It! or Regret it!”
Enjoy this podcast of my live conversation with Molly Kingston Founder CEO Oakley Bourbon on The Debbie Nigro Show. If you’d rather read than listen the transcript of the audio is below.
AUDIO TRANSCRIPT:
And now back to the Debbie Nigro show.
0:00:04
(Speaker 2)
I’ve got a legendary story to tell you right now and you’re going to meet a legendary woman, pioneer in the spirits industry. Hey everybody, I’m Debbie Nigro. You know, I love bourbon. I drink it and I like good bourbon. I got into it because my boyfriend drank it and I was a scotch drinker forever, but now I’m like, I’d rather have the bourbon.
0:00:40
(Speaker 2)
So I heard about this amazing woman and fellow women bourbon lovers are going to love today’s story and love meeting my next guest. Like infamous Annie Oakley, who I was talking about earlier in the show, Molly Kingston is a pioneering woman and she began investing in unique barrels of bourbon and studying the bourbon industry. She was curious why it didn’t feel inclusive of and approachable for women.
0:01:05
(Speaker 2)
So she had this big vision, then she had the nerve and the gut, you know what I always to disrupt an industry that didn’t see her coming. Oakley Bourbon is what we’re going to be talking about today. That’s her creation, the world’s first and only bourbon, to launch with a 20-year-old edition, which, you know, wow, and thousand-dollar bottles have sold out in minutes.
0:01:29
(Speaker 2)
So I want to welcome Molly to the show today, and congratulations on your Oakley Bourbon. Hey, Molly. Hi, Debbie.
0:01:37
(Speaker 1)
Thanks so much for having me.
0:01:40
(Speaker 2)
Oh my.
0:01:41
(Speaker 1)
Looking forward to chatting. And I also love bourbon, that’ll come as no surprise to you.
0:01:46
(Speaker 3)
Yeah.
0:01:47
(Speaker 1)
And so, happy Women’s History Month. I mean, bigger than my brand or your brand is the fact that it’s Women’s History Month. And as an interesting side note, I happen to be passing through Hood River, Oregon. Right now I’m on some family travel. And I’m staying in a hotel
0:02:05
(Speaker 1)
that was built in 1888. The historic Hood River Hotel, it sits right along the Columbia River and the Railway Depot is right behind the hotel. So you may hear some very noisy trains in the background.
0:02:20
(Speaker 2)
Oh, we love noise. It’s all good. I just said to my engineer, Bob, I hope I don’t hear those fire engines somebody always has an emergency during my show it’s beyond anyway Molly this is a this is related
0:02:32
(Speaker 1)
because Annie Oakley was built she was born in 1860 and I haven’t had a chance to research this but I have a feeling she came through here and she may have stayed in this very hotel because the timing would align just perfectly so that’s all pretty interesting and I’m hoping she’s kind of roaming the halls of the hotel.
0:02:51
(Speaker 3)
If that’s the case, Annie is with us.
0:02:53
(Speaker 2)
She’s great. I’m a huge Annie Oakley fan. I was saying that I did a little bit about her before you came on and why I love her so much and why she was a pioneer and just an amazing woman. You know, when she couldn’t shoot anymore, she started teaching other women how to shoot so they could learn self-defense.
0:03:08
(Speaker 2)
And women helping other women is what I’m all about. So I extend my hand wholeheartedly to you today to congratulate you for being a pioneer, especially during Women’s History Month, and also to find a little bit out about the back story of this, because it’s a big story, Oakley’s spirit. So tell me about your inspiration for this.
0:03:31
(Speaker 5)
Yeah, of course.
0:03:32
(Speaker 1)
We were just talking about her. My inspiration was Annie Oakley, and I’m a bit of a history buff. And she was a woman who embodied empowerment and equality, very, very progressive for her time. And she would still be seen in many ways as progressive today. So I love the interplay of kind of the history, which Bourbon is also steeped in history, as you know, and has a long and storied past kind of pre-prohibition and then survived prohibition and came back roaring back to life right afterwards. But, you know, Annie Oakley was a fascinating person.
0:04:10
(Speaker 1)
I know you talked about her before I came on. But she is an absolute inspiration then and now. And so we really created this brand reflecting her values of strength, independence, and inclusivity. Again, she was very progressive for her time. She was friends with and advocated for Native Americans. She was obviously a woman competing in what had been really exclusively a manned sport
0:04:36
(Speaker 1)
or competition. Right. And so, you know, she lived her life fearlessly. She did, as you said, helped other women. And she actually tried on two occasions to help the U.S. government by putting together a band of female sharpshooters who she offered to first President McKinley to put together
0:04:58
(Speaker 1)
a band of sharpshooters for the Spanish-American War, and later she did that again as we were approaching World War I. So in every way, shape, and form, she was an absolute inspiration to the value set and the spirit of Oakley.
0:05:15
(Speaker 2)
Wow, that was a mouthful but you said it all. Do you envision all of the women who drink bourbon now coming to raise a glass to you, to Annie Oakley and to each other? Is that what’s in your head?
0:05:29
(Speaker 4)
Absolutely.
0:05:30
(Speaker 1)
We created this as a real lifestyle brand that fosters community. vein, yes, I do see women coming together, groups coming together, people, families for special occasions or a camping trip or an evening sitting out on your deck and having good and deep conversations over a glass of bourbon, neat or on the rocks or however you choose to take it. Beautiful.
0:05:55
(Speaker 2)
Now, I thought it was really interesting that you decided to launch, and I’ve never heard a launch like this, with a 20 year single barrel bourbon. What were you thinking about, and how successful has this been? I can’t believe you’re selling thousand dollar bottles of this stuff.
0:06:13
(Speaker 2)
Tell me the back story on that. Yeah, absolutely.
0:06:16
(Speaker 1)
So I am very patient. Obviously. And so many, many years ago, I started investing in some pretty special barrels, put those up in a rickhouse and waited and waited and waited. During that time, I was ideating this brand, thinking really about what this brand would reflect, what it would look like, what it would be like.
0:06:38
(Speaker 1)
And bourbon is on its own timeline, as in many respects we all are in terms of when we peak. So just like an Olympic athlete, you’re trying to peak at the very right time, looking for when that is and so we could have launched sooner, but honestly we waited for the perfect moment and kind of let the burden speak for itself. So it’s very poetic that that happened when it was 20 years took our time and you could
0:07:12
(Speaker 1)
say that we did this right rather than doing it fast.
0:07:17
(Speaker 2)
I’m asking myself a question in my head, so I’m going to ask you, how many times did you check on that barrel over the 20 years?
0:07:21
(Speaker 1)
I stood there the whole time. I was on the floor right there next to it.
0:07:27
(Speaker 2)
Because I’ve been checking on a regular basis, maybe. And you know, you just said something really fun, because I’m just peaking now, which is shocking. I didn’t think it would take this long, but sometimes great things take time that you didn’t see how much time.
0:07:42
(Speaker 2)
And patience, yes, I’ve had to learn patience. It’s an amazing thing that takes a long time to learn. You learned it quickly in life, apparently, 20 years ago at least. So now here you are with this Oakley bourbon, and I’m noticing that there’s a great appeal
0:08:00
(Speaker 2)
amongst collectors. I was on the website oakleyspirits.com. It mentioned, you know, that things got sold out in seconds. Tell me about the collector market in this.
0:08:11
(Speaker 1)
Absolutely. So there’s a very strong collector community, as there is for many things, you know, rare watches, rare art, rare bourbon. And we were fortunate to really get the attention of that market early on and in part because we were launching with the 20-year which is, you know, unheard of and also in part because we benefited from a very new and very high tech. And again, this is where we’re sort of playing in the history and the modernity and availing ourselves of the current technology.
0:08:50
(Speaker 1)
There’s a new anti-fraud technology developed by Solana Blockchain in partnership with a company called Iridia. We’re the first brand in the world to put that on our bottle. So that was a massive attention draw for collectors
0:09:04
(Speaker 1)
because the anti-fraud ability of this particular tamper strip, which is the strip of paper that goes over the top of the bottle, allows you to confirm at any point going forward for decades and decades that this bottle has never been tampered with. That’s incredible. It’s amazing. Yeah, yeah. So
0:09:22
(Speaker 1)
that was another thing. And of course, Solana has been talking about this and been talking about Oakley. So the collectors really took note of what that was and what this product is. And they have been phenomenal. I have interacted with many of them personally. They are anxiously awaiting our Collector Edition 2, which is coming out a little bit later this spring. I can say that many of us have become friends, and so we’re excited about the community that
0:09:51
(Speaker 1)
Oakley is fostering.
0:09:52
(Speaker 2)
I want to be friends with you. This is too cool. You know what I was drawn to, because I’m a girl who bought Cracker Jacks back in the day just to get the prize. You mentioned that there are limited edition Royale playing cards that may come with a chance to unlock exclusive experiences that are on your website as part of what you can purchase for swag for Oakley.
0:10:16
(Speaker 2)
What is that all about?
0:10:17
(Speaker 1)
Yeah, well, as you know, poker was at its high point back in the early part of the 1900s. And so we, as a play, a reference towards history, our creative director developed super unique, beautiful playing cards. They are on our website. Every one of those cards is individually designed.
0:10:41
(Speaker 1)
So this is a deck unlike any other. And then on top of that, we are including a very special gold card in one out of every 50 decks. So if you buy this deck of cards, not only is it a great gift and fun just to play with for any card game,
0:10:58
(Speaker 1)
but you have a random chance to win a gold card, and then the gold card entitles you, if you choose, to register on our website for membership in an affinity club, and the gold card recipients will have all kinds of cool access to everything from chatting with us about what charities we eventually select to invitations to events, to discounts on merchandise, you know, all kinds of cool things.
0:11:25
(Speaker 1)
So we’re really excited about that. It’s one more way that we’re building community and engaging with our customers in a way that’s very novel.
0:11:33
(Speaker 2)
Everything I’ve looked at visually that represents Oakley spirits is total class. I have never seen a presentation like this. I spent a lot of time on your website oakleyspirits.com. The photos, the branding, the feel that you’re in there with Oakley, Annie Oakley, the West, everything about it, it just makes you want to be part of it. So I need I need
0:11:58
(Speaker 1)
to congratulate you all because that’s genius. Thank you. It’s a testament to my amazing team. We have a very small and very nimble team and it’s all them. They are leading the way with things that are never before seen, an amazing look and feel, visually captivating, and the message really comes through in every single aspect of our design aesthetic, our website, our label, our bottle, right down to the shape of the bottle which I wanted to have a good feel in a woman’s hand. You don’t have to hold the bottle with two hands for it.
0:12:36
(Speaker 1)
You’ve maybe been in that position before where you have to really grab these kind of thicker bottles with two hands.
0:12:43
(Speaker 2)
I always manage to get it done though, that’s no problem.
0:12:45
(Speaker 3)
Good for you, exactly.
0:12:47
(Speaker 2)
I like the idea of it being a little easier.
0:12:50
(Speaker 1)
It’s a little easier, I think. Our bottle is kind of elegant, very different. And my task was to make this appealing to women and not alienating to men or alienating to anyone. So, if our core values resonate with you, you are our customer.
0:13:08
(Speaker 2)
Oh my gosh, I’m so excited because I can’t wait to drink it while wearing my fringe jacket and my cowboy hat. I’m like so ready for this.
0:13:17
(Speaker 1)
I hope I am there for that.
0:13:19
(Speaker 2)
Oh yeah. Speaking of ready, am I allowed to talk about Ready to Ride, the next thing that’s coming?
0:13:24
(Speaker 1)
Not quite yet, but it is coming and we’re excited about that. Before that, we have our Collector’s Edition 2 coming out. That’s going to be a rare, exciting product. And then this summer, we have a very special summer release that’s on its way and that will be a moderately priced but still very premium product that is going to be very fun. So plan to put on your fringe and spend the entire summer with Oakley following our story because it’s going to be a great summer with our new summer release.
0:13:54
(Speaker 2)
Alright, last question for you as we come to the end of our time together. Not quite yet, we have a little more time. Just tell me, as a woman-led brand, and if you can do it in like, you know, two words, in a traditionally male-dominated industry, how hard has that been? On a one to ten?
0:14:12
(Speaker 1)
It’s been maybe, you know, a three for me, because every industry that I’ve ever been in has been male-dominated, but I love men, so I find a way to work together.
0:14:23
(Speaker 2)
Me too! And move it all forward. Me too! Oh, me and you are going to be best buds. We’ll be having a toast together soon. So wonderful to meet you, Molly Kingston, the founder behind Oakley Spirits, Oakley Bourbon, a very special new bourbon out there celebrating female empowerment and obviously classy new product entrepreneurship at its finest. Oakleyspirits.com is where you’ll go find out
0:14:47
(Speaker 2)
all about it. And I wish you a fabulous day. Happy Women’s History Month. Good having you today, Molly.
0:14:53
(Speaker 1)
Likewise, Debbie. I look forward to raising the glass with you. Likewise, Debbie. I look forward to raising the glass with you.
0:14:56
(Speaker 2)
Can’t wait. Can’t wait. We can’t leave now, but I’ll see you soon.
