Wine App for Beginners: Jeff Gillis's WineLikes Story

[00:00:00] Sanjay Parekh: Welcome to The Side Hustle to Small Business Podcast, powered by Hiscox. I'm your host, Sanjay Parekh. Throughout my career, I've had side hustles, some of which have turned into real businesses, but first and foremost, I'm a serial technology entrepreneur. In the creator space, we hear plenty of advice on how to hustle harder and why you can sleep when you're dead.

[00:00:22] On this show, we ask new questions in hopes of getting new answers. Questions like, how can small businesses work smarter? How do you achieve balance between work and family? How can we redefine success in our businesses so that we don't burn out after year three? Every week I sit down with business founders at various stages of their side hustle to small business journey.

[00:00:43] These entrepreneurs are pushing the envelope while keeping their values. Keep listening for conversation, context, and camaraderie.

[00:00:56] Today's guest is Jeff Gillis, the founder of Winelikes, the only wine app that guides beginners to the perfect choices for any occasion. Jeff, welcome to the show. Thank you for having me. So I'm excited to have you on. This is I think you've got a really interesting story that we're going to dig into. But before we get there, give us a little bit about your background and what got you to where you are today.

[00:01:16] Jeff Gillis: Sure. I am a former food and beverage director at some five star hotels all along California. And then I am also a Sommelier and that's, I love wine. I got out of the hospitality business because I have three kids and if you know anything about hospitality, you have to work weekends and holidays.

[00:01:39] And so I actually got into marketing and biotech. And then I decided like everyone else during COVID that I want to work for myself and start my own business. And my wife stays home and works at home and I love my wife and I love spending time with her too. So I'm like, let me start a business. And so I'm like, I really know wine really well, and I know Mar, I have a degree in marketing, a master's in marketing and entrepreneurship, and I'm like, let me see if I can crack the code on wine and see how you can introduce new people to wine. And that's basically by no wine app has gamified wine. So that's what the Winelikes app is about.

[00:02:25] It's about gamifying wine to get you a not wine novice or a wine enthusiast. To drink more wine and enjoy wine and meet new people in new wines.

[00:02:34] Sanjay Parekh: Oh, interesting. Okay, so you've got an interesting kind of shuffle that happened there. Yes. So, okay. The f and b industry, the hospitality industry was not going to suit your lifestyle and what you wanted to do. Correct. You pivoted into biotech? Yes. Which is interesting. How was that transition for you?

[00:02:54] Jeff Gillis: I got easy and I always tell people, and a lot of people ask me that, who try to get out of hoity hospitality is all about customer service.

[00:03:03] Sanjay Parekh: Uhhuh.

[00:03:03] Jeff Gillis: So look for other customer service jobs, biotech. I got into because it was a customer service. It was, it's a. What I worked for a patient driven company, so the company was seeking patients instead of doctors. And so you need to learn how to speak to patients and be very empathetic. Well, if you've ever checked in a hotel or had a restaurant and had an issue, as a manager, you have to be empathetic and be understanding, and the customer is always right.

[00:03:37] And the same with someone who's sick. Or needs just to have someone listen to them. You have to basically smile through the phone. And that's how I made that transition. So, you know, sometimes people are like, ah, I don't want to do a customer service job, but hospitality, it is customer service. That's all It's.

[00:03:58] Sanjay Parekh: Well, so it's interesting kind of your perspective on this because you're not looking at yourself as I work in this industry. You're saying, I have this skillset, and what industries fit with that? So that's correct. I find that interesting because that skillset too, I think takes you into entrepreneurship because that also relates to, you know, like needing to get customers and all that.

[00:04:20] But let first ask you, is this the first time that you've done anything entrepreneurial like this?

[00:04:25] Jeff Gillis: Yes, except if you count a lemonade stand when I was a kid, maybe. But, you know, luckily I grew up with an entrepreneurial family. My father works for himself and I feel like I'm pretty creative myself and yeah. But it is basically the first thing I did by myself. Yeah. Or out there.

[00:04:48] Sanjay Parekh: So, okay. So you came up with this idea of like, okay, let's gamify kind of wine and wine drinking. For your background you know, so let me step back. Why did you decide that this needed to be an app? And especially given the fact that I don't think you're a developer, a software developer. I am not. So how did these kind of decisions affect the development of this?

[00:05:12] Jeff Gillis: So the app started out is like I mentioned, my wife, I have a family and all of that is. Prior to COVID and all of that, we had a lot of date nights and we went out and I made a lot of dates and basically I thought is there a dating app

[00:05:34] with wine. And how can you be like, oh, I drink merlott. You drink merlott as well as one thing that if you know anything about the restaurant business the margins are pennies on the dollar. So, and buying off this wine online, it's, they're not getting the restaurants involved, so how do you kind of get the restaurants involved?

[00:05:57] And so I thought of. My wife looked at me, oh, maybe think of like a dating app or something like that. And then the process of brainstorming started and be like, okay, you can only get so far. Okay. You like Merlott. I like Merlott. Let's meet. That's really not going to work. And so it's like, how can we capture all of these trends in social media, in wine together to make some type of app? And I thought of an app just because I have no idea. That's what everyone was on at the time.

[00:06:37] Sanjay Parekh: Okay. So you decided to build an app, but you can't build an app yourself. Right. So how did you go about this?

[00:06:44] Jeff Gillis: First advice, number one, if you're looking to develop an app, obviously you want hire the right people, but know something. And I think where we look at failures in my business trajectory. I didn't know and still don't know much about development. So I would say research yourself on what you want to do or learn at least the basics. But I just started taking, for example, when you're in hospitality or when you're in any job and you need to get estimates, right?

[00:07:18] Right. Or even at home, you call three to five companies, right. To talk to them, find out a, the pricing, see if you get along with them. And that's what I did. I just googled app developers and started interviewing, and I matched well with this one company, and I'm like, all right, this is my idea. And they helped me transform it.

[00:07:43] Sanjay Parekh: Yeah. So did this company end up being somebody local to you in the US, Offshore? Like what?

[00:07:49] Jeff Gillis: So I will say they're in the us. They were, they are in the US but as it's been four years and that contract ended with the Uber economy and everything, I found out... Here's business advice. You know, you can pay a company, which is most likely a third party, and then they're paying someone else to do the work. Or you can cut out the middleman and try to find it yourself. And then that's where I went on one of these websites that promote developers or gig economy, and I'm being like, why don't I just hire someone like this and spend a lot less money?

[00:08:30] Sanjay Parekh: Yeah. Yeah.

[00:08:30] Jeff Gillis: So that's where I am now. So that's a piece of advice is you don't have to hire the big company.

[00:08:37] Sanjay Parekh: Yeah. So that's the way you're approaching it now. How many people do you have working on the app with you? Is it ongoing or is it just like as needed?

[00:08:47] Jeff Gillis: It is ongoing because I keep tweaking the app and like I said, we, I tried to capitalize on what's going on in the world as far as trends and everything. For example, one of the games is a Windle, which is Wordle. So we have that game. We just added another game, Regents, which is a coloring game. Adult coloring is very popular right now, so we have a coloring book on the app. So I'm always tweaking and I think you... the thing they don't tell you when you're developing an app, technology changes fast and you have to keep up.

[00:09:28] And it's not like, here's an app, you're done. It's like, okay, libraries now have to get updated and that costs money. And then, okay, Google did something with Android and then Apple did something. So now you have to tweak it to make sure all of your security preferences and all of that. So. Sadly it's an ongoing battle.

[00:09:50] Sanjay Parekh: Yeah. So when you got into this, was there anything that made you nervous about trying this? Like, you know, you're, you've got this app idea and you don't know actually how to build it. Like what made you nervous?

[00:10:04] Jeff Gillis: Probably I had blindfolds on and wasn't nervous. I'm like, this is really cool. I could do this and then...When you actually develop something or have a business and like, look, I can go into an app store and see my app. I'm in 176 countries. Right? Like, that is such a cool thing. Yeah. But that's, you know, again, it's the honeymoon period I guess. So I've had a lot of, what I'm nervous about is what is your ROI and how much money can you spend? If you are actually going to look to make money?

[00:10:45] Sanjay Parekh: Let's talk about how, how you balance these things a little bit too, because this is a, this is a side hustle. You've got full-time job, you, you've got multiple things that you're doing. So talk about that and how you're balancing your time between these things.

[00:11:00] Jeff Gillis: I, it's very hard and I think the biggest advice I. I want to give people is you need to have consistency when starting a business. I don't have consistency with my app and that is probably my, one of my biggest downfalls because, for example, what gets users on Learn Organic Marketing, you got to go on off the social, other social media sites.

[00:11:25] There's something in apps called push notifications. So I can do that in my app to get users more engaged and all of that. And it's just I don't have the time. I do have, I'm still in marketing for biotech. I do have a family and then I do in order to pay for the app, I got another job. So I am a adjunct college professor at a culinary school.

[00:11:49] So I teach hospitality and wine at culinary school, so, which is so much fun and all that, but yeah, you can't really balance it out. Yeah, I wouldn't know how. And it's like I used to be able to stay up until 2:00 AM wake up at 7:00 AM and really get going and then, you know, you get really excited about it. And then the honeymoon phase zone, it's like, okay, what's the point? If I don't do this today? It's not like I'm going to gain another user.

[00:12:23] Sanjay Parekh: Yeah. What, so that's interesting that you took on a second job just to fund the development of the app. You know, was, was that the sole strategy of, of taking on that adjunct and, and then you discovered that you liked it, obviously, so that, that's a nice side effect.

[00:12:41] Jeff Gillis: I think the sole part of getting that other job was a, yeah. I'm like, ooh. I can be a college professor. That sounds great. And I think it's like what everyone's dreams for is like, do we want to work for the man all our lives? And that's why I developed this app in the first place. And it's like, okay. You know a professor position or teaching position gives you a little more flexibility than the I would say nine to five, but I'm in, more of an officer in the corporation. So I'm 24/7. Something nine to five exists when you're in management or upper management anymore.

[00:13:23] Adam Walker: Support for this podcast comes from Hiscox committed to helping small businesses protect their dreams since 1901. Quotes and information on customized insurance for specific risks are available at Hiscox.com. Hiscox business insurance experts.

[00:13:35] Adam Walker: Let's, let's switch gears a little bit and talk about like, balancing this with like family life. Like you've got literally three jobs then right now, right? Yes. So you've got the, the marketing director or your marketing executive. Mm-hmm. For the biotech, you've got the college professor, job, and then then wine app. How do you balance these things and keep them separate or do you keep them separate from home, personal, family life?

[00:14:03] Jeff Gillis: I don't, at, it's 7:00 PM when I'm, I, so I'm obviously culinary school. I've spent lots of times at restaurants. I'm the chef in the family, so at 7:00 PM when I'm cooking dinner, you can hear me yelling, recording. So I'm doing my little social media plug with wine because I have food there for the app. And then the kids, although the weekends are be like if we don't have anything going on luckily my kids are a little older with play dates. Where it's like, okay, dad's in the office working on the app or doing something.

[00:14:39] And then I have my kids get involved, like when my kids love Wordle, so I'm like, help me develop this, you know, to test it. And yes, they're not of legal drinking age, but they're not being, they're not drinking the wine, they're just playing with wine. The games to see, to test the bugs. So I've tried to get them involved and I think the most important thing is to show them that live, live your dreams or develop your dreams. I, I should say, or, you know, I want them to find something all that they're successful at, and even if they're not successful at, at least they can say, I'm having fun in life.

[00:15:20] Sanjay Parekh: Right. Yeah. That's an interesting, like you, you've really. Kind of merged the things that you like together there because you're, you're doing social media posts doing the thing that you already love already, which is cooking and, and you're doing for the family anyways, and it kind of just blends into the business then at that point. How do you, like, on that social media side, how do you manage that? Are you just doing the recordings and all that yourself and then doing postings or do you have somebody helping you with that, that part of it?

[00:15:57] Jeff Gillis: I have, I had some people help me, luckily some friends, but then I've had paid, but obviously it's another expense.

[00:16:04] So it's like, do you, you have to look at, like I said, that ROI, do I take the time to do it myself or do I pay someone to do it? And what's going to going to happen or with that, and it's like I have to really. Do it on my own. And again, I think it's also, that's my baby. Like I want to do it right. Does it take more time to hire someone and then look at their work and, okay, I like it, and then approve and all that, rather than, all right, let me just bang this out myself.

[00:16:37] Sanjay Parekh: Right. Yeah.

[00:16:38] Jeff Gillis: And you have to look at the, you know, the balance of, they say life work balance, but it's just the cost of everything. The cost analysis, I should say.

[00:16:47] Sanjay Parekh: Yeah, that's perpetually the problem too, right? With entrepreneurs, especially because a lot of times you feel like, well, nobody else can do it as good as me and if I've got to review your stuff anyways. And this is the trap that we fall into. And it, your load never gets lightened because of, of kind of that mentality. And you've got to be able to figure out how to delegate. And I will admit I have a problem with this myself. So it's not like I'm the one telling everybody else the right way to do this.

[00:17:17] So let's talk about like what you've put into place for yourself then, at least to help with your process or is there any technology or apps or systems that you use that help you kind of in your day-to-day flow of work and getting things done?

[00:17:33] Jeff Gillis: I think sadly, I hate to.... ChatGPT has been a lifesaver whether that's social media prompts or expanding writing a blog for the app and all of that to try to get users and doing, you know, instead of hiring an SEO person, I can throw this into a AI and say, give me this, give me an SEO prompt.

[00:18:02] Then I throw it on the internet. So I think the biggest time saver for me has been the invention of AI, which is funny because there are probably a wine app a day is coming online, which is crazy and I don't know why and how. And it's because of the invention of AI. And I stress on my app, we have no AI and I won't allow AI, it's all user generated.

[00:18:30] The word is I tried to promote is belonging. Like, you belong here, you belong with wine. And I don't want a machine telling you, oh, you like Pinot Noir. I want Sanjay in Atlanta saying, I just had this lovely pinot noir. Try it.

[00:18:48] Sanjay Parekh: Yeah.

[00:18:49] Jeff Gillis: You know? Yeah.

[00:18:50] Sanjay Parekh: Yeah. That makes sense. Was there a big technical challenge that you had to get through in building Winelikes?

[00:18:58] Jeff Gillis: I think I'm still getting through it. And that's what I mentioned is I have no idea what I'm doing.

[00:19:04] Sanjay Parekh: No, and I mean that, that's more like a how to build it, like, but was there like a technology challenge at all, or?

[00:19:11] Jeff Gillis: No, the thing is the, you know, when we talk business talk barriers to entry, right? Or the high or low. They're low. Anyone can throw up an app on the app store. On these app stores, and then period. Anyone can, you know make sure. I would say get trademarked. I'm trademarked. All that. And all of my stuff through the process is trademarked, so no one can copy me. But, and I would say, but no the barriers to entry are so low that someone can just be like, all right, now I have an app called Wine Lovers App, and I'm one loss, you know, which is also, you know, the competition then, there's so much competition.

[00:19:54] Sanjay Parekh: And I think, do you think, yeah. Do you think this is good or bad? For consumers and regular people, like all of us. Like what how do you feel about that?

[00:20:04] Jeff Gillis: I promote a free market society you know, I, a laissez-faire, like, yeah the app or the business will succeed if people enjoy it. They're not going to just do go, all right, well this one, look, I'm a free app, so I can't say there's a lot of wine apps there that aren't free and all that, but in general, I think if people like the app or like the business, they're going to flock to it instead of going, all right, this is mediocre, I'll do it.

[00:20:40] But I think with everything the development side, or I should say, barriers to entry. The biggest thing is there's so much app fatigue now.

[00:20:51] Sanjay Parekh: Yeah. Have you learned anything about how people kind of interact with either like a wine app like yours, or just wine content in general? Like is there something that's you've discovered along the way that's interesting?

[00:21:04] Jeff Gillis: I think it's so interesting to me is like, how do these people drink every day, have you on social media, and how are they drinking some of these expensive bottles? But then you learn the tricks of like, oh, that guy works in a restaurant and he's grabbing it, saying he's doing it or she's doing it. But not really. But I think no. What I have learned about human behavior is, I mean. I think they're going to help you out. I have some diehard users on it that, you know, who I've never met who are in your, you know, a big Europe, big drinking is in Europe and who I've never met. And they're like, oh, I found this bug, you know, or this happened and let me help you, or let me just tell you.

[00:21:54] And I think that's great. You know, there's a lot people that I've probably lost that didn't tell me what's wrong?

[00:22:02] Sanjay Parekh: Yeah. Yeah. That's interesting. Yeah it's great to see that. Has that given you any kind of encouragement in terms of like, okay, maybe we're going down the right path because now you have these diehard users that are hoping that you'll succeed.

[00:22:17] Like, you know, if you've got a business that is awful, like you don't get diehard users, right.

[00:22:22] Jeff Gillis: It gives me some encouragement that, okay, I have the right game, so I have the right concept. But then you go to, okay, this is a niche market. Wine drinking, which is getting smaller and smaller by the day. If you listen to and read about what's going on with health and all of that.

[00:22:44] Sanjay Parekh: Yeah.

[00:22:44] Jeff Gillis: And the issues. And then what it is like, okay, I have this niche market, but I can't stay alive just for love. Yeah. You know, and that's the hardest thing is like, great, I would love to be for these people, but why aren't you telling your friends? Right? I can't ask somebody. I can be like, Hey, you know, I could do a fun newsletter. Oh, if you like us, rate us five stars and all that. And so, but it's just like, all right. But you know, I always say in hospitality if you have a bad experience, you're going to tell 10 people. If you have a good experience, you're going to tell two people.

[00:23:21] Sanjay Parekh: Yeah. Yeah. Which by the way, I don't think I've ever said or haven't said this on the podcast in a long time.

[00:23:26] If you're listening to this podcast and you do like this podcast, go ahead and rate it five stars because I would appreciate that. And what's interesting is. Very few people will actually take the time to do that. Right. So by the way, if you're listening and do that, I do definitely appreciate you doing that.

[00:23:42] Okay. Last question before we kinda get into the closing advice portion of it. It kind of dawns on me that you've spent a lot of time in this industry. And Yes, like you're saying, maybe. A shrinking industry, but there's definitely still other people that are looking to break into this industry.

[00:24:01] Do you have any kind of advice for folks like that, that are looking to get in like a non-traditional way and breaking into the wine industry?

[00:24:09] Jeff Gillis: Yeah. I mean, what's great about the wine industry is there's so many faucets of it, whether you want to be a winemaker. Or you want to be a som at a restaurant or obviously the marketing side of it.

[00:24:21] There's so many avenues to pursue. And I would say the one thing is get a baseline. So for example, there's what's called the W set which is where you get your degree in som or in wine and everything. I'm a wset too. And there's a wset four. There's upper level, so at least get, just like you should have, I shouldn't have gone in a baseline of developing, I should have taken some master classes or gone, you know, to a community college and, you know, Python 1 0 1 or whatever code to learn and all of that so I could at least do some stuff on my own or know, okay, people who I hired are doing it right.

[00:25:06] So I would say get a baseline and go for your wset level one or level two at least, and get that and find out what you love about or like about the wine business, whether it's marketing or I want to make wine.

[00:25:21] Sanjay Parekh: Yeah. Yeah. Great advice. Okay, Jeff, couple last questions for you here. Sure. You've been working on this for a while now. Thinking about kind of all the challenges that have happened over time and the things that you've learned from them, is there something that you like now knowing what you know, that you would love to go back in time and do differently? And if so, what is that thing?

[00:25:43] Jeff Gillis: There is a time when you have an app that no time, let's go before that, before you have your idea or when you have your idea. Go see if your idea is worth it. I went straight. I have this idea. Here's some money. Let's make the idea happen. I didn't do enough market research, so that's what I would probably tell your audience, who's looking, okay, I'm about to start a business. I have this great idea. Might be a great idea in your head.

[00:26:15] Kudos to you. But go out and ask the market if this is really something they need and something they will buy.

[00:26:24] Sanjay Parekh: Yeah. That's an interesting response from somebody who's a marketing person, right? I know to say. I should have done the market research. Yeah. And I think that just highlights that a lot of times we as entrepreneurs, as founders, we sometimes have hubris in terms of the things that we do. And sometimes it's good to have that grounding.

[00:26:44] Jeff Gillis: Look, the pro my issue, I, and like I said, maybe I should invest in therapy instead of my app. I'm an internal optimistic, so I will wake up and I'm like, this is the day I just hired a influencer and now I'm going to get a thousand users. Well, never happened in my life, but it's just that perpetual, like, okay, it's my baby. Or it's like, yeah, I have a great idea. Yeah. You know?

[00:27:08] Sanjay Parekh: Yeah. Yeah. And that honestly is a required skill too, of entrepreneurs and founders to be optimists because if we were pessimists..

[00:27:17] Jeff Gillis: Yes.

[00:27:17] Sanjay Parekh: We would never make anything new. So, because we would just say that it's going to, not going to succeed. So we need the optimists and the as founders and entrepreneurs.

[00:27:27] Okay. Last question for you, Jeff. Yeah. If you were talking to somebody who was thinking about. Doing like you and launching a side hustle or you know, getting a new job so that they can fund a side hustle. Hopefully that they can make it into a full-time business. Is there any advice you'd give to them?

[00:27:45] Jeff Gillis: I would go all in, but don't go all in. And that's where my dad, like I said, what's an entrepreneur always taught me, don't quit your job until you have another job. Period. So you may have this great idea and like if I have quit all my jobs and invest all the time in Winelikes, it still wouldn't be a success.

[00:28:06] Where you need, you always need revenue coming in, and that's where whether you have to have two jobs like me to have it, or you have your one job you still need, don't, I guess don't put off your eggs in one basket.

[00:28:21] Sanjay Parekh: Yeah. Great advice. Jeff, this has been fantastic. Where can our listeners find and connect with you online?

[00:28:27] Jeff Gillis: Of course. Well, guess what? I have an app. So you can go to the Google Play Store or the iOS store and just look up Winelikes App. And that is me. Or you can find me on social media on Instagram mostly. I am Winelikes app. And that's where usually you can find me.

[00:28:48] Sanjay Parekh: Awesome. Thanks so much for coming on today.

[00:28:50] Jeff Gillis: Thank you, Sanjay. I really appreciate it.

[00:28:55] Sanjay Parekh: Thanks for listening to this week's episode of the Side Hustle to Small Business podcast, powered by Hiscox. To learn more about how Hiscox can help protect your small business through intelligent insurance solutions, visit Hiscox.com. And to hear more Side Hustle to Small Business stories, or share your own story, please visit Hiscox.com/side-hustle-to-small-business. I'm your host, Sanjay Parekh. You can find out more about me at my website, SanjayParekh.com.