Raj Alva: Co-Founder of Whiskey JYPSI
Episode 799
On today’s episode, we welcome Raj Alva, Co-Founder of Whiskey JYPSI — the award-winning whiskey brand redefining modern American whiskey through craft, culture, and storytelling.
Raj is a serial entrepreneur, brand architect, and investor known for building culturally resonant consumer brands that thrive during moments of disruption. With Whiskey JYPSI, he saw white space in a category steeped in tradition and chose to approach it differently — focusing on blending excellence, creative freedom, and emotional connection rather than owning a distillery or following conventional playbooks.
In this episode, Raj shares how Whiskey JYPSI was built by leaning into uncertainty, why blending can be a creative advantage, and what it takes to build a brand that resonates beyond the bottle. We dive into brand-building during disruption, the role of culture and storytelling in consumer loyalty, founder responsibility beyond profit, and how values-driven leadership creates durable, meaningful businesses. This conversation offers powerful insight for founders, operators, and anyone building brands with intention and conviction.
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To learn more about Raj Alva and Whiskey JYPSI:
https://www.linkedin.com/in/raj-alva-a654801/
https://www.linkedin.com/company/whiskeyjypsi/
Transcript
Kara Goldin 0:00
I am unwilling to give up that I will start over from scratch as many times as it takes to get where I want to be. I want to be, we just want to make sure you will get knocked down. But just make sure you don’t get knocked out, knocked out. So your only choice should be go focus on what you can control. Control. Control. Hi everyone, and welcome to the Kara Goldin show. Join me each week for inspiring conversations with some of the world’s greatest leaders. We’ll talk with founders, entrepreneurs, CEOs and really, some of the most interesting people of our time. Can’t wait to get started. Let’s go. Let’s go. Hi everyone. Welcome back to the Kara Goldin show. Super excited to have our next guest here today. The conversation is going to be about building when there’s no clear playbook, having the conviction to move anyway. Raj Alva is the co founder of an incredible brand that I just ran across called Whiskey JYPSI and Raj is a builder in other industries, but decided to jump into this industry, the spirits industry, and really find the disruption and make the impossible happen. So not an easy feat, especially in the spirits industry. So Whiskey JYPSI, it has challenged a lot of assumptions in the whiskey world, and it doesn’t follow the traditional script. It happens when storytelling and craft and purpose are actually aligned, and that’s exactly what Raj and his co founder is doing. His journey is shaped by earlier experiences, as I mentioned, in other industries, and today, I cannot wait to hear more about what it takes to not only build brands in other industries, but in the spirits industry, and what he’s seeing with his co founder, so Raj, welcome to the Kara Goldin show. So excited to meet you, and I absolutely love what you’re doing.
Raj Alva 2:12
I appreciate that. I appreciate that. It’s it’s always fun building things. Yeah, definitely the kid and end up building businesses when you’re an adult.
Kara Goldin 2:22
Exactly, exactly. So for listeners who maybe haven’t heard of Whiskey JYPSI yet, it’s spelled j, y, p, s, I, what makes it fundamentally different from most whiskey brands that we find on the shelves today? Yeah.
Raj Alva 2:40
So when Eric Church, my business partner, and I were thinking about getting into this space, he was already partnered with Jack Daniels. He was the second person ever to have his name on a bottle. Frank Sinatra being the first, and it was a barrel pick. So basically straight whisk bourbon into a barrel. Actually, not that’s Tennessee, so whiskey straight into a bottle. And I said, Derek, if we’re going to do this, because he just came up on a golf trip where we were way too overserved, and talking about different businesses, he was asking about Grayson, which is my other business I was a founding investor in. And I said, if we’re going to do this, we have to do something different, because it’s a pretty tough space to break into. There’s a lot of players, a lot of big players, a lot of small players. And so we spent a couple years really honing the plan. I want to say we started the Ibn 21 we launched in mid, early to mid 23 so it took that long buying the liquids. So what I would say, what we did differently, and it was interesting. When I was researching the field, I had a lot of connections, which I didn’t realize in the industry. Joe Magliocco is the owner of miters, which is my favorite brand. I called him. He gave me, kind of some parameters of what we would be looking at. He actually told me not to do it. He said to own Rick houses. And then I had some other friends, whistle pig guys in high west so and they were all great. They were sharing information, but every time I would ask why they did things a certain way, the answer would come back, well, that’s how we always did it. And I said it was kind of an aha moment. I said, Okay, let’s figure out how they’ve always done it, and see if there’s something else that can be there. And that’s why, if you look at our product categories, every one of them is different. That we have one tier which is a blend of world whiskeys. We have another tier that’s finished in woods. We have a third tier. That’s a grain story. And you know, traditionally, people look down on on blending and in finishes. But if you look at the largest whiskey company in the world, Jack Danny, sorry, Johnny Walker, it’s a blend. And so we saw an opportunity there. And I think people are now. All starting to see, you’re seeing a lot more finished products come out. You’re seeing not blends as much, but some. And so, you know, we really want a different direction. I think people were expecting us to come out with these single barrels, similar to what Eric had and and our first product, which was a world blend, ended up winning double gold at San Francisco world spirits, which is the highest award you can get. And then our third product, also, which is a grain story, we found Cherokee White Eagle corn, which is the grain used by the American Indians when they were teaching the settlers how to make spirits. We use that in our entry price point, and then we double barrel it. And that one double gold at the World spirits. So I think we’re on the right track. We’re seeing, we’re seeing a lot of growth so, and we’ve got some pretty interesting new products coming out, again, all non traditional finished products. So it’s a, it’s a different category that we have really dove into on the whiskey bourbon area.
Kara Goldin 6:05
So the name JYPSI spelled j, y, p, s, I, where did you come up with that?
Raj Alva 6:12
So Eric has a song where he talks about drawing cards with a Whiskey JYPSI. And so we had a bunch of other names that we were thinking about, but it kind of stuck. And we wanted something that was easy to say. If somebody’s at bar and they say, Hey, I’d like a JYPSI and coke or a JYPSI old fashioned, you need something that was easy to remember. We wanted to spell it differently, because the word JYPSI can have some negative connotations in some places. And from you know, the reality is, we’re we are a new generation of the word JYPSI, right? We’re not the tradition. We’re doing things differently. We’re exploring the world, which is, you know, we’re travelers and we’re taking risks, but at the same time, we’re not the old way of doing things. So we wanted to spell it differently as well.
Kara Goldin 7:01
So how crowded is the whiskey industry overall? And just to give people some scope of how big this
Raj Alva 7:14
is, I think they only need to walk into a liquor store and see how many brands there are. I had a similar experience when we started gracing clothier. So I don’t know how much you know about the golf clothing industry, but it was probably 2015 I met Charlie Shafer, who’s our founder, and he was had a business plan he was pitching. And I said, Okay, well, let me take a look at that. I love the concept. Peter Millard just been sold to Richemont, and Ralph Lauren was really de emphasizing golf clothing, so I saw a window, and the timing was perfect when he pitched me, and I said, All right, this is I like it. I like what you’re doing. We can start with golf and we can build it to a lifestyle brand, which is where we are now, 10 years later, it’s been a huge home run for us. But I remember going to the PGA show that year, and saying, Okay, let me see how our brand fits in. There was hundreds of clothing companies. And I panicked. I said, What did I just get myself into? I mean, this is crazy. It was similar when I went into the first liquor store that was a decent size. There are so many whiskey brands. And look, I want all my competitors to do well, but there’s a lot of them that just don’t have a reason to exist, because they’re really just bottling somebody else’s product and putting it on a shelf. And we don’t distill our own product. We find distillers who we can partner with. They use our grains, they use our yeast strains, and so we use their equipment, basically, but, but we we don’t have our own distillery, which really with the over capacity, and then industry makes no sense for a small company. So when I walk through the aisles, another reason it took so long, I said, we have to have something different. And I would tell you, the average liquor store probably has 50 types of American whiskey, maybe more sitting on a shelf. Total Wine could have 100 plus. If I had to guess, how many are out there? Total brands, 1000 Wow. And yeah, and, but the main producers, there’s probably only three or four who produce MGP in Indiana. You can tell the label, they’re required to say where the product came from. So if you see Indiana, you know was MGP. If you see Kentucky, it’s probably Bardstown or Dickel or some of the other guys who sell the third party producers. If it’s Tennessee, it’s probably Tennessee distilling group. So if it’s North Carolina, it’s probably southern distilling so there’s a lot of third party producers who will produce for other brands, and they make excellent product. But you know, for us, we want to do something with that excellent product, not just put it in a bottle.
Kara Goldin 9:50
Yeah, definitely. So your packaging is beautiful, and I would imagine in the spirits industry, especially when it’s. Uh, sitting on the shelf for the consumer to make that decision. Maybe they’re not familiar with the brand name, but the packaging has a lot of weight. So can you talk about that, and what your experience was in building that?
Raj Alva 10:16
Yeah, you hit the nail on the head. So we we went around and we looked at all the different bottles we saw in the industry that we thought were interesting. And we this was a long process, and it’s funny enough, I actually have quince an alley, one of our prototypes, sitting right here. But we went through 50 to 100 different bottles that we said, Okay, this could be interesting. That could be interesting. What do we like about that? What do we not like about that? And we hired a person who had made some of the ones we liked as a bottle. There’s a specific bottle designer, and what we decided was we weren’t going to limit this based on cost. So I think our bottles, if I did Yes, are probably twice the cost of any traditional bottle you’re going to see on the shelf. We only found one group who could actually make it. We even went to Italy to a group that makes these custom models. They couldn’t figure out how to do it. It’s basically a hammered copper still, but in glass. So whiskey is distilled in copper stills in the old days, and they’re hammered typically, so they have these little indentations. So that process, that bottle process, took one full year to design that bottle, and you hit the nail on the head. In terms of the visual, we call it the bar cart test. If it’s sitting on your bar cart, does somebody see it when they’re walking by? Well, it’s even worse when you go into a liquor store, because all that the facings I told you, 50 100 bottles, is someone going to see it visually right when they walk by? Does it stand out? And so, you know, from that standpoint, that we had to get that right, even though it costs a lot more. And so we’ve actually won a lot of awards for the bottle as well. The bottle design, it’s very hard to make. We’ve found one more group that can make it. We’re switching to them. They’ve been able to cut our costs back a little bit, 40% probably so. But it is, it is the key to me. Either your label, bottle or both, has to stand out when you’re walking by an aisle. And you know, I would say this with any consumer product, you know, shelves are crowded, and what’s going to make that person come up and actually look at the bottle, or look at your bar, or whatever it is? You need to have something that’s going to catch somebody’s eye to get them to look at it.
Kara Goldin 12:32
Yeah, definitely. I remember when we were launching hint and we had a clear label, and what we didn’t take into account was the lighting in the stores and the and the light was coming through, and, you know, we wanted everyone to know that it was clear, right, that there wasn’t dyes being used, and, you know, it wasn’t tainted in any way with any type of color. But, but the consumer couldn’t see it. And so when we actually were forced by New York tax law that changed quickly, or we were going to have the bottles pulled off the shelf, we changed to a white label, because we couldn’t get the clear labels right away. And 10 extra sales, and we’re like, what happened? Yeah, we just couldn’t believe it. No one saw it, no creative team. No one saw what the issue was, until, until that happened, yeah.
Raj Alva 13:34
And so in that the eye test, right? The consumer walks through the aisle. Shelves are crowded. What are they seeing? And again, I see that in the clothing world too. With Grayson, when I go through pro shop, I try to see, what is our clothes? How are they? How are they putting it up and displaying it? You know, what do they what does the consumer see? And does it stand out? And if it doesn’t stand out, you’re going to walk right by the ones that you’re going there purposely to buy your product. We’ll buy it, but that’s not going to grow your brand. You need people who are there and don’t know your brand, or might know a little to see it, pick it up, look at it, and then, you know, ask the questions if they need and walk out. Right? So, yeah, the eye test is fair. Is failed when? And again, I tell anyone who’s listening to this, go to a liquor store. I promise you, 75% or more of the ball is just blend right in. So it’s, it’s hard, it’s a hard, hard way to do it.
Kara Goldin 14:29
Yeah, definitely. And you talked a bit about this, but the three tier system is something obviously that you are, that you have to adhere to. And I tell founders this all the time, that it doesn’t really matter who you know. I mean, maybe to get an introduction, it matters on who you know in the industry. But you have to have a lot of different elements. You have to have the great. Product. You have to have a story, you have to have the labels, you have to be able to deliver the product, and otherwise all the introductions in the world go out the door. What has been the most challenging for you and actually getting the product launched?
Raj Alva 15:19
Yeah, so the three tiered system is definitely, to me, it’s archaic so it I’m not sure why the league we’re going to have it anyway. We need the distributors, we need retailers, but it really makes a brand very hard to build profitably, because even if you called me to buy a product, I still have to pay the distributor. I still have to pay the retailer, right? It’s the wine industry has found a way around it. We have a little bit of a loophole in some states where we can do some direct shipping, but it makes it very hard to build a brand. And I don’t know if that’s great for consumer, but from so that the profit side was is hard. Fortunately, Eric and I have deep pockets here. We can get through that. But you know, we’ve been blessed that he and I have pretty good connections. So it does open doors. If I was coming in blind without knowing I have friends who own some of the big distributors. Funny enough, we actually didn’t go with them, we went with some of the smaller distributors, and because of Eric’s name, we’ve been getting inbound calls. A lot of small brands haven’t been able to get distribution. We’ve been getting inbound calls. So I think that. But the challenge, there’s so many challenges starting a brand in this industry, the challenge I think we’re having now is just getting the word out, because we didn’t want it to be a celebrity brand. We consciously didn’t put Eric’s name on it, so we get all these great reviews. Now it’s the marketing side. How do you target market? We’re only in a handful of states. We didn’t want to go nationwide, because you want to make sure, in the states you’re in, the product’s moving on the shelves. Because if it’s not moving, the retailer is going to, you know, stop carrying it. The distributor is going to get angry. So wherever you’re going, you have to make sure it’s moving. So you have to spend marketing dollars and so without pulling too much on Eric, because if we use him too much, he becomes a celebrity brand. That’s where we’re, you know, we’re at that stage now of getting targeted marketing, and we’re seeing great growth, but that’s the harder challenge for me. It’s keeping one hand tied behind my back, because I have a celebrity I can use, but we don’t really want to use them for because you don’t want the brand to get tainted, right?
Kara Goldin 17:38
So, so you’ve been involved in Grayson and other brands as an investor, versus actually operating and rolling up your sleeves. So it’s a little bit different. I have that right, right that you haven’t, yeah, well, Grayson, Grayson.
Raj Alva 17:54
I’m actually a founding board member, and when we started, we were so small, I was rollin up my sleeves. So Kara Lee and the team, 99 90% whatever it is, but they were, you know, real, really leaning on us, because he was a creative guy who did some operations, but we helped bring in the COO found a new CFO. CFOs. You know, there’s small companies. The people who are coming in don’t have the same experience, so they’re leaning on you. So I’d call it active board management, right? You’re not rolling up your sleeves the way the team is, but you’re pretty involved. I mean, we’re about to do something fairly exciting, Grayson and, you know, Charlie and I and one other board member are kind of negotiating, structuring the whole thing. So, so it’s a little bit different. On this one, I have brought in a CEO recently, because at the end of the day, at a certain scale, you need to bring some you need to bring more structure in. And I think some founders make that mistake where they wait too long to hand the, you know, the reins off a little bit because they don’t want to lose control. But I think the smart ones, when you’re scaling fast, you’re gonna make a lot of mistakes if you don’t bring people in underneath you who’ve kind of dealt with that. And so I saw that happening here. And, you know, brought in a CEO who had been at two companies that had grown in the spirits industry, grown and sold for big numbers. So he’s really helped me figure out the launch plans, how many states we should go and how we should launch in them. And so, you know, you check your ego at the door and you do what you need to do.
Kara Goldin 19:35
Yeah, definitely. So I mean, that’s, I think maybe lessons learned along the way, but also when you think about, I guess, instinct and and trusting yourself a little bit more, that maybe your younger self you would have ignored anything like that. That come to mind when you think about how you’re viewing building the company today. I mean, you mentioned one point where you brought in a CEO pretty early, which is great. But also, I think just just looking at the landscape and recognizing that not everything is going to go right, right, that you’ve got to, you know, you’ve got to, if, if you’re forced to go right, then you know, you’ve also got to figure out, what else can you do to make up the
Raj Alva 20:35
correct point? Yeah, there’s, you’re always going to make mistakes, right? There’s just, you just have to realize there’s going to be mistakes made. It’s, can you minimize the damage those mistakes do to you, right? And then do you learn from them and pivot quickly? How quickly do you catch those mistakes? And we made plenty of them at Grace, and we still make mistakes, right? And so if you, if you don’t fix them fast, they can be fatal. And so, you know, for me, having smart people around me, bringing them in a little earlier than I probably would have, I wouldn’t have done that when I was younger. You know, when you’re younger, you think you can do everything. And so for me, it’s, I want the smartest people in the room. I’ve heard the expression, you know, a plus CEOs want a plus people around them. And you know, B CEOs want C people around them, right? And I’ve seen that in the corporate world, which I did M and A for a long time, and I can tell you, the best CEOs were the ones who just surrounded themselves with very smart people and wanted to hear their views, and they’re going to make the ultimate decision, but they want to be surrounded by talent. And that’s my view at this point in building businesses, you want best talent you can get because and they might challenge you, but listen to them, because they’ve experienced it before. And if I was in the same business for 30 years, I might have a different viewpoint, but I’m starting different businesses in different industries, and there’s people who know a lot more than I do, and so you know, bringing that talent in early, it’s really valuable to avoid those mistakes.
Kara Goldin 22:06
Definitely. Yeah, definitely. And I think also hiring people who also believe to hire people on their teams that actually know things that they don’t is just so critical. So I found that as I was building hints that that was such a key thing that I learned early on and in the tech industry when I was growing up, that, you know, the key is to find people that actually know things you don’t, and then you also continue to stay engaged, because you’re learning along the way, no matter how successful you are. And I think that everything that you’re saying applies to that thinking too
Raj Alva 22:55
well, and also having people who are willing to communicate, I find where I’ve had problems. You know, when you’re not running the business day to day fully is and especially in this distributed world we live in now, my team’s all over, master distiller and CEO in Michigan. I’ve had two people marketing and head of DTC in Nashville. We blend in ball in Nashville. I’ve got a co in Illinois, communication is critical. And you know, for me, I’ve found the ones, people who don’t work, are the ones who keep everything themselves and they think that they get all insecure and they want the information, and that’s their power. And it’s really important teams are communicating, because otherwise Mistakes happen, and you, you know, you end up having to fix things that you probably could have fixed. And I think you especially in small organizations, if you find somebody who’s not willing to, you know, push down or let, let other people do it, share the information, it really creates problems in an organ a small organization.
Kara Goldin 23:59
Yeah, definitely. So when you look at at the build you talked briefly about that you’re really focused on getting it right in the states where you’re distributing, I think often people, you have a lot coming at you, people, I’m sure, who know your co founders name, and you know they’re they. They want you to pay attention to this state and that state. So how do you rein that in and make sure to stay focused and keep the team focused, because all the opportunities that are coming your way will spread you too thin not allow your balance sheet to look the way that you want it to look in six months or one year from now, all those things. But what would you say to that?
Raj Alva 24:48
Yeah, we made that mistake early. We were chasing the shiny pennies to some extent, and we’ve kind of restructured it a couple of things. One, obviously, there’s a lot of people who just want. There to show up and do bottle signings and everything, part of and our answer back is, we’re not a celebrity brand. We can’t do that. We’re not going to, you know, we’re not out he’s not out there, you know, pitching this. We’re try our product, see what you think, and if you like the product, let’s push the product, not not Eric. And we’ve done really well with that. More recently, it’s been, you know, when we switched to that message, people try the product and they love it, and it’s been flying so that that’s, that’s one, two. We’ve also been much better at targeting accounts that we think have long term potential, not yet that initial sale. But you know, how do they fit in the cat in the state, in the area they’re in? So we go, we’re basically going less broad and deeper into into account. So places where we could open 600 accounts, we’re really only opening two or 300 and we did the same thing with Grayson. We could have gone on almost any pro shop. We limited. We try to go into pro shops that are higher value, higher volume, higher value, so that the sales people can focus on them as can be good customer service. Versus a bunch of small, small accounts. It’s just much harder to manage. And so we took a similar approach here, deep, big, bigger accounts, deep relationships. And you know those relationships work when you, you know when you when they see success, and they they’re that, you know, they’re one of the bigger accounts in the state. There’s ABC is an example in Florida, is the largest retail chain in terms of store numbers, and we’ve become friendly with the owners, and we’ve done partnership stuff with them, and we are now one of their fastest moving new products. So it’s to me, that’s the way you do it. You pick the key accounts, focus on them, go deep with them, and then the other accounts start to come after.
Kara Goldin 26:52
Well, I’m so excited for you guys, and I know that this is going to be a big success. So thank you so much for coming on and sharing a lot more about Whiskey JYPSI, everyone needs to check it out. Look for it at the total wine stores, ABC and and also many, many fine establishments. So seriously, check it out. It’s an incredible, incredible spirit. And like I said, the packaging, you can’t miss it. It’s it’s, you guys have nailed it. So Raj, thank you so much for joining today, and thanks everyone for listening. Thanks for having me. Thanks again for listening to the Kara Goldin show. If you would please give us a review and feel free to share this podcast with others who would benefit, and of course, feel free to subscribe so you don’t miss a single episode of our podcast, just a reminder that I can be found on all platforms. At Kara Goldin, I would love to hear from you too, so feel free to DM me, and if you want to hear more about my journey, I hope you will have a listen or pick up a copy of my Wall Street Journal, best selling book undaunted, where I share more about my journey, including founding and building. Hint, we are here every Monday, Wednesday and Friday. Thanks for listening and goodbye for now.
