Jamie Debole // Makers Podcast 002

A serial entrepreneur, Jamie shares stories about hustling in Shanghai, taking the central Texas lacrosse scene by storm, coordinating epic trips around the globe, and the transition of his current business GlobeKick from a service business into a product and technology company.

The Makers List


The Makers List


January 28, 2022

Jamie Debole // Makers Podcast 002

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Video Transcript

Grant  0:03  All right, welcome back to the second episode of the Makers Inc. podcast. Today, I've got the great fortune of talking to my good friend Jamie Debole, who is the founder and CEO of GlobeKick, he's going to be sharing some of his experiences, the company that he's building today and some of his experiences in the past. So maybe, Jamie, if you give us a little intro to who you are, what you've been up to.

Jamie  0:31  
Sure, um, you know, to kind of quickly, you know, bring you up to speed, I suppose, like, I've been dabbling in entrepreneurship for a long, long time, and never actually had maybe a traditional job, so to speak, and all these experiences that brought me to where I'm at today, or at least feel like they have, with what we're doing with GlobeKick, which is quite a bit different from all the other businesses that I've been involved with prior to this, those were more service based businesses, and, and, you know, navigating various challenges that those presented.

You know, GlobeKick is more of a travel technology company that makes it easy and fun for couples to plan the perfect honeymoon. So kind of a new set of challenges, but excited about the ability to really make an impact in the lives of people for a very meaningful experience for them.

Grant  1:28  
Awesome, maybe if you could take us back in time and share sort of your first experiences with entrepreneurship.

Jamie  1:38  
I'm sure yeah, outside of like, you know, I guess I'd always sort of had this little entrepreneurial bug probably planted in my head from my mom and dad, where, you know, I can remember some of my earliest lessons from my dad saying, you know, I climb the corporate ladder, when you can be the corporate ladder.

They both ran small businesses, you know, there wasn't anything like big or overly, you know, world changing, but kind of seeds were planted early on. So I had a yard, lawn mowing business, I had, you know, my own summer camps that were going and I did that starting around like 15-16 years old. And when I was graduating college, I was brimming with confidence, yet lacking in skills. But I was pretty, pretty bold and brash at that time and thought, you know, that was back in 2008. And I knew a lot of people were making a lot of money over in Asia, and things were booming over there economically. And I ended up, you know, essentially, skewing everything with my major to fly over there to pursue business opportunities, whatever might come along, I wasn't even sure what it was, I had some vague ideas of what I wanted to do. But I just kind of threw myself into the fire, and want to see if I could survive and come out on the other end. So I'd say that it was probably that that experience over in China was my first real experience with what I would consider like true entrepreneurship, where you just dealing day over day with complete uncertainty and trying to navigate it and figure it out.

Grant  3:14  
I love that you just thought that a lot of money was being made, and you were just gonna go be a part of it. It's like there's a gold rush. you're heading out west. Like it wait. So what did you end up doing? I don't know if I've heard this story.

Jamie  3:29  
Yeah, so I took Mandarin Chinese as part of my coursework all through school. So I did have a little bit of a baseline for being able to navigate things over there. And I had this kind of very fuzzy, vague idea that I was going to get into I'd always been very interested in like, e commerce and digital marketing. And how could I maybe set up a drop shipping company and use you know, sell things online and kind of cut out middlemen and shipped directly from these warehouses over there, particularly as it related to a sport that I knew well, which was lacrosse. And so I went over there with the rough goal of establishing some relationships, figuring out where the opportunities lied and just kind of betting on myself to adapt and figure it out as I went along. But that was sort of the target. And it didn't work out that way as it never does, right. But I did find a nice little pocket where I was essentially a middleman for expats moving over to China. And I could help them establish themselves in the city by finding an apartment finding transportation purchasing different things that they would need, and I was able to leverage my Mandarin skills to purchase these things at you know, was like a local price and the foreigner prices, you know, two times whatever the locals are paying so I was able to do purchase at a local price and sell it to some foreigner at below market price that they could receive and kind of take the Delta there within.  

Jamie  5:09  
I did that for I had a pretty, you know, there's a lot of people moving over there to like teach English and needed jobs, I was helping them get set up with their jobs and you know, plugged into the different schools. So there was a never ending stream of potential clients. But you know, essentially it was an expat relocation kind of consulting service that made its home over there in Shanghai back in 2008 and 2009.

Grant  5:35  
That's right, buy it for $1 and sell it for $2. That's so cool. I did not know that story. I didn't realize that you had moved over there. I didn't know that's what you were doing. So how does that relate to here? How long did that last? Before you ended up moving back to the states?

Jamie  5:54  
That lasted about a year, it was very stressful at that time, it was, you know, as technically a foreigner over there working illegally, I wasn't able to open a bank account, I wasn't able to really establish myself for my business. So stuffing tons of money underneath the mattress and hoping you know, someone doesn't find it. And it presented a lot of challenges. And in that time, I met some folks, and this is kind of right around that time that the Timothy Feriss four hour workweek was coming out. And it was starting to form my mentality towards entrepreneurship, or what kind of business I would like to be involved with. I was working really long days over there, it was stressful, it was difficult. And this kind of, you know, new way of looking at, you know, a lifestyle that, you know, business or a side hustle that could support myself became increasingly attractive. And I ended up you know, coming back to Austin, Texas, where I chased the the person I was dating at the time. And you know, Austin became attractive for a lot of reasons. It was a cool, booming, you know, young city. And there's a lot of low hanging fruit from a business perspective where deep expertise in the sport of lacrosse, I was able to kind of come in there in a in a market that was still emerging and have relative expertise to others in the area, and ultimately build, you know, kind of a thriving business that the goal was to always digital marketing, digital marketing, digital marketing, I loved the leverage that it provided, even though I didn't have the skill set for it, necessarily. But I came back and started what was essentially like the ESPN of Texas High School, lacrosse, and used all that web traffic that was coming to read about rankings and what's going on in the state and all this stuff, and use that platform to launch all my own camps, clinics, tournaments, and travel teams. And it was a, you know, when you know something, well, you know, you can do it pretty easily. And I'm fortunate that I love coaching, I love the impact that my coaches have made on my life. And the impact I was able to make on these kids lives, whether they were third grade or high school. So it was a lot of fun. eventually You know, I was ready to change it up, which I did in 2015 to start GlobeKick. But throughout that process, I learned a lot both about myself and entrepreneurship and, and kind of everywhere in between. So a really fun and valuable experience. And that's what drew me from China back to the States. And kind of set me up to where I am today.

Grant  8:41  
So that's super interesting. You created a digital platform where you were sort of aggregating content about lacrosse in the area. How are you driving traffic? Like how are you marketing that site and getting eyeballs on it?

Jamie  8:59  
Yeah, it's pretty easy and very grassroots organic, you know, everyone loves to read about themselves and their team. So you know, like rankings is a very easy way to start. And then contacting, you know, just basically going door to door to contact every coach in the area and then in the state and saying, hey, I'd like to write a feature on you and your team, you know, and upcoming season preview, you know, we're and we're just word of mouth naturally spread from there. And before we knew it, we were having 20,000 people a month visiting the website, without any sort of traditional advertising dollar being spent.

Grant  9:37  
That's really cool. And a good reminder, like, even though you ended up getting all this inbound traffic and you didn't have to pay to get people to come to the site, you still had to do all the hard work to go door to door and make those contacts and have in, you know, you're sort of selling. You're not trying to get them to buy anything, but you're building those relationships and writing that content. how are you how are you determining rankings?

Jamie  10:06  
Yeah i created you know just borrowing from what was working and you know what i'd seen being seemingly done well online i would you know straw poll various coaches i wanted to keep as many people from around the state as engaged as possible so i would i'd have all my experts you know weigh in on who they thought after each week was you know what are the state rankings looking like i had my own little team of they were you know basically full time across coaches at this point as well as working with me you know we were writing articles and getting like in depth knowledge on you know games and we're going and scouting different teams the top teams in the state and just just having a lot of fun with it and then coming out with our own sort of ranking which was always controversial as well as you know some sort of coaches ranking where we were able to include more people from around the area

Grant  10:56  
That's so cool when you think back on that time running that business what were some of the biggest challenges that you faced?

Jamie  11:10  
You know the i was very very fortunate to have an opportunity to get acquired in 2015 and the time in my i felt had come for me to do that primarily because the challenge was you know i wasn't generating revenue through the website i hadn't quite i done a good job bringing eyeballs to the site but my revenue driving you know engines of the business were all events in person events that required me to be there which was generally you know with kids being in school and whatnot it's nights and weekends so you develop these very close relationships with these families and these kids who you're really invested in their success and you care about them and you want them to achieve their dreams and helping them achieve their dreams in a certain sense necessitates you been there every weekend to support them in that so the biggest challenge was you know sort of some version of what like golden handcuffs like oh this business is doing well i'm enjoying it but it's limiting my ability to do other things and now that i'm feeling like i'm ready for a new challenge or i want to grow in a certain capacity or i want to travel or do something else you feel these really strong relationship ties with people that you've been working with for years upon years and you don't want to leave them in a way

Grant  12:41  
Yeah that's tough when things are going well with your business but it's no longer where you want to be spending your time that's a that's a very difficult place to be and i'm sure a difficult decision to make you mentioned you you ended up getting acquired do you mind sharing what you can about about that process?

Jamie  13:04  
Sure yeah it really kind of came out of nowhere it was you know central Texas was really starting to grow and you know from being in sort of at a much earlier stage in developing relationships whether that's with various coaches in town or parents or access to facilities and fields which were particularly challenging to come across we had built quite the little network and as larger regional or national players started to eyeball the central Texas market is someplace that they wanted to expand into you know they face basically the choice of coming in and trying to recreate what i've done in the area and try and leverage their brand name to do that or and compete with me in the process or they could try and find a way to essentially buy me out and i could transfer a lot of that those relationships and those contacts and kind of help oversee a transition period where i can get them settled in in the market and kind of instantly become that market leader that we had built ourselves so a little bit tricky and sticky and you obviously want to team up with the right group to make sure that these kids and these families are well taken care of and so there's a bit of a feeling out process with a few different folks who were trying to come into central Texas at that time but ultimately you know we made the decision that we thought was gonna be best for us it wasn't about how much money can we make off of this acquisition you know at that time it was more about how do we leave these people we care about in good hands and how do we try and make the best outcome for everybody.

Grant  14:46  
Yeah that makes total sense and thinking about alignment between the two organizations is obviously such an important part of ensuring the long term success of that acquisition. I'm curious if you could share any advice that you would give to someone who's you know at that stage or about to go through that process and in ways that you were able to effectively evaluate the different groups that you were considering?

Jamie  15:15  
Yeah that's interesting you know so much of it comes down to reputation and talking with folks parents from you know maybe other when we're looking for other markets that these companies operate in and seeing you know what's being said about the organization what's being said about the coaches what's being said about the leadership you know do the parents feel like they're getting the value out of it or they feel like they're getting scalped because unfortunately in that business there's a lot of a lot of fiefdoms being created by people who don't really have the kids best interests at heart and on the flip side of that there's a lot of others that aren't trying to grow the biggest business but really do have you know their their kids interests in heart so just kind of like exploring that and trying to figure out well what do i stand for and then how do i team up with an organization that you know stands for something that's the same if not you know very closely similar very cool that i use.

Grant  16:17  
Yeah and i'm curious about... did you have employees at the time and if yes, how did you manage the transition through the acquisition for your employees?

Jamie  16:30  
I did prior to the acquisition, but i've kind of gone on and off with employees versus you know 1099 contractors and Texas law has made it a lot increasingly easier to essentially bring on people as you know contractors rather than full time employees so let's essentially i went that route so the acquisition i didn't have employees to really consider so much as i had a large network of coaches that you know supplemented a significant portion of their income by working you know events or working with me in some way shape or form so you know trying to leave them in a good spot was important but ultimately it was up to the you know the new incoming regime to you know work with the resources that they were allotted to figure out what they want to do with that and i tried to set everyone up for success in that process

Grant  17:24  
Cool. So when i think about you mentioned one of the major challenges for you was that you had this asset you had a digital asset that was you know getting traffic and you were struggling to monetize in a way that didn't require you to be there it wasn't scalable it was it was all events like now you've you've run you know another business for several years you've got you know a whole new set of perspectives based on sort of you know additional years of operating businesses and working in the sort of digital marketing and sort of variety of different spaces and thinking about businesses for that much longer. If you could do one thing different at your time during the lacrosse business what would be the one change you would make?

Jamie  18:23  
I would have definitely diversified the revenue streams and tried to lean more into. I would have made a more concerted effort to branch into digital product you know so much of the value that we were providing was knowledge based and i would have liked to have continued to increased not just giving away free content and free knowledge i'm always happy to do that but so much of the world of sports at youth for better for worse i think oftentimes for worse revolves around recruiting and what coaches are what people can help you know me and my son you know or daughter you know ultimately achieve their dreams but you know get that scholarship and it's unfortunate parents pay a exorbitant amount of money you know at the behest of these experts that are there to supposedly look out for them you know 1000s upon 1000s of dollars every summer going and chasing around different camps tournaments clinics all these things i would have leaned much more heavily into some premium content some evergreen kind of content that really could add value to and shed light in areas that i could see these parents really needed it and have diversified in that way to leverage the traffic base into you know more premium content or like courses and subscriptions this is back you know 2011 through 2015 they're still very early for some of those things and Other tools to make those available, you know, weren't nearly as readily like at your fingertips as they are today. So it's something I could ideate. But I didn't really have the skill set or the tools at my disposal, or at least I didn't feel like I did in order to bring that to life. And looking back. I did if I just maybe stuck with that a little bit longer.

Grant  20:19  
Got it? Yeah. Maybe tell us a little bit about the transition into GlobeKick.

Jamie  20:26  
Sure, you know, so I think actually, this is interesting, when I kind of stepped back in 2015, you know, why? Why am I doing this? Like, what, what do I want my life to be about? And I think, you know, to borrow from Simon Sinek, it's very much like, everything starts with why, why are you doing something, and I haven't always had great answers for that throughout, you know, my professional career and whatnot. But at this time, I started to really figure out what I wanted to do, there's very, there's so many This is, I could dovetail on this forever. In terms of, I think, knowing your why will help you figure out what advice to listen to, because there's a lot of conflicting advice out there and knowing what kind of business you want to create, because it aligns with what you want to do with your life. And what your why really is, is kind of where you have to start. But at that time, I realized, you know, I really wanted to help more people travel the world, some of the most formative time in my life had been from China, or from traveling with friends who became you know, best friends and whatnot in the life experience that I've been able to gain and was very fortunate to be able to gain. You know, throughout my 20s, I wanted to help other people do that. And the biggest barrier to that was remote work. Like, or being stuck, I should say, in not being able to work remotely. So we were sort of in 2015, that transition, I really wanted to, I wanted to make a meaningful contribution to the world and to people's lives. And I don't want to necessarily do that just through, you know, athletics and sports and, you know, recruiting for colleges and the seemingly like, endless hamster wheel of, of these poor kids. So it was at that time that I basically took some time off in 2015 and travelled a little bit. And when I returned back to Austin, I decided, you know, what, I can see this, you know, emerging trend in the market with digital nomads and remote workers, and whatnot in the biggest gap. And everyone's looking around on social media and you see all these glamorous photos of people traveling the world, and you're dreaming about, oh, how do I do that? And the reality is, it's not that difficult. And I wanted at that time, we started GlobeKick to basically help people make that transition from someone who has an office space worker into someone who was working more remotely, and feeling empowered in their ability to do that and travel the world with other people doing that with a sense of community and with a sense of security. And I thought that's how I can make a more meaningful contribution in the world. And that's what kind of gave me the boost to pursue it.

Grant  23:14  
Yeah, it's such a cool idea. And I know you've now traveled all over the place, you've taken people on trips around the world, what are some of the most meaningful things you've been able to do?

Jamie  23:29  
Oh, God. For me, it's always about the people, you know, like, some of the adventures are amazing, you know, I can think of like, the ones that immediately come to mind might be, you know, like camel trekking in the Sahara, and sleeping in the desert or like dog sledding in Norway under the Northern Lights and going through, you know, Cambodia and, and working on an Elephant Sanctuary. And all these experiences were fun and amazing. But what really made them amazing is the people you share it with, and the people you meet along the way and develop relationships with. So each one's a bit unique. And what we found through, you know, years upon years of doing this, whether it was a one week trip or a three month trip, the bonds that are formed when you go through when you're forced to be vulnerable yourself and somebody else that you're traveling with also has to be vulnerable. Because you're in a new situation, you have to rely on each other to figure it out together, the bond that gets created is so much deeper than just kind of going about your day to day life in an environment that's comfortable. And that those were the most rewarding experiences that I look back on the friendships and not only that I made but that, you know, people that were traveling with us were able to make with each other and with some locals, those were the ones that, you know, that's what that's what really stands out.

Grant  24:46  
Yeah, that's so amazing. I mean, the combination of the opportunity to get to travel the world and make that a business and get paid to take people to new places and experience it with them. And then also like you to actually build those relationships with the people that you were working with, but also the people that you were, you were taking on those journeys that's imagined, there were some incredible years, hopping around the globe.

Jamie  25:13  
You know, they were, but it sounds more glamorous than it is like it is stressssfull, and those were, those are some of the most difficult years of my life. Like, I know, it sounds cool and sexy and all that stuff. And at times, it was, but you know, we've evolved GlobeKicked where it is today, because of a few reasons. One of which was the juice isn't worth the squeeze, like the stress of, of that kind of business is extremely taxing, and challenging to scale and support, because you, you're only as good as your last trip, and you're only as good as the trip coming up. And to kind of get over this threshold. I know, you've got experience. You know, with things like this, especially like events based businesses, it is very challenging, and you can get yourself into financial trouble pretty quickly. You know, if you're not careful in how you're managing the dollars, so yeah, it was awesome. But it was, it was challenging, and ultimately, like spectacularly failed, in some ways, like our original business plan that we were really, you know, pursuing just blew up in our face. And we, you know, misjudged the market. And yeah, it was a wild time and a great learning experience all in all, and I'm grateful for it, because it's brought me to where we are today, but far from like, the glamorous, you know, vision that it sounds like, you know, would you say you're traveling the world and getting paid to do it? It wasn't quite like that.

Grant  26:47  
Got it? Yeah. Do you mind sharing a little bit about sort of what your business model was, and how the unit economics worked or did not work? for a trip?

Jamie  27:00  
So it was essentially, you know, we started out. We wanted to ride, take a step back, we were riding these overarching trends that, you know, Millennials are dissatisfied in the workplace. And they're changing jobs every 26 months on average, and the cost to a business to re recruit, rehire, and retrain, that employee was exorbitant, you know, the learning curve, the whole thing that's involved, you just have constant turnover, is very challenging for the business to, you know, really sustain its momentum. So what we had ideated was a way for businesses to offer to certain employees that had the ability to work remotely, you know, what we were thinking was, GlobeKicks 1, 2, 3 month long trip to be a great employee incentive in a way to attract and retain top professional talent, hit certain performance metrics, you unlock this benefit that allows you to go and work from Barcelona for a month or two. And, you know, the company pays for that in exchange for you sticking around, and you know, continuing your job, because theoretically, you're happy there. And so we started out like with a very b2c direct consumer model, and we, it was like a rocket ship out the gate. And our first few months, we'd done like, a quarter million in revenue, it was, you know, thinking the product seemed to be flying off the shelves seemed like everybody wanted us and we thought, wow, you know, this is going better than we expected. And in the process of running that trip, though, a couple of things occurred, one, we kept spending to acquire new customers for future, you know, trips. And it takes a good deal of like, foresight and planning and relationships, to stand up a new month long experience with apartments and co working space, and all this stuff in a new city. And a lot of money has to get put down in advance in order to secure those relationships, and secure, you know, essentially, what you need. So we were spending quite a bit. And after our first sort of trip, we realized we might be in trouble here. Because the sales cycle at these companies takes a while to develop, you know, oh, yeah, this does sound interesting. Let me know how it's going. You know, and let's stay in touch. And I want to sell this to other people, you know, in our, or our leadership team. And what ended up happening on our first trip was like, 50% of the people quit their jobs. You know, there's a second subsection that was working for themselves and was able to do that on their own time. There's a sect that had quit their job or left their job like right in advance so they could travel for three months without being encumbered. And there was a section that was working and had to do that work from abroad. And now if you think about it, practically, you're in like Valencia, Spain, or, you know, Portugal, Lisbon, Portugal, and you have to work USPS hours. So now it's, you know, basically, you're six to seven hours ahead over there, now you're working like two to 10pm. from Valencia, Spain, it while all your friends are, you know, just you know, hanging out and having fun and exploring, and what people were doing was just quitting their job, like, you know what, there's only six more weeks like I'm gonna enjoy my time here. Screw the job like, so what we rather than, you know, helping attract and retain company, you know, employees, all these employees were leaving the company. And we quickly realized that Oh crap, the model that we thought seemed so clever and seemed to be working so well at the gate, you know, had some serious structural flaws. And now we were in this weird cycle of making commitments further and further out in time. And, you know, do you keep spending in order to, you know, meet a minimum threshold to make these economically viable? Or how do you have to navigate kind of across this platform? And so it was a pretty interesting time there. And we probably well, in hindsight, we certainly misjudged the market, misjudged our products ability to meet the needs of the market, and ultimately got ourselves in some hot water in the process.

Grant  31:27  
Do you think you would have needed to sell through to companies? I can see now with the story that you just told why it wouldn't work. But obviously, that's in part why you have to try things to solidify whether or not they will work. Do you think it was possible for you to find enough people who were in your first two segments that you described? So people who are working for themselves remotely? Or who were out of work for whatever reason to keep the business moving forward without sort of added need for selling through to businesses?

Jamie  32:08  
Yes, certainly the market was there amongst those people, but the solution wasn't, you know, what ended up this kind of interesting thing ended up happening, where on the trips themselves, you know, a certain point in time came when certain folks or basically decided, like, Wait a second, you know, why am I paying for some of this stuff, I can find my own Airbnb, I'm just gonna do that instead. Or I should just do that instead. And they kind of, you know, I don't want to be disparaging in any way, I completely understand the psychology behind it. But what would end up happening was, you know, the model was, was systemically broken, because even though we were the impetus like the safety net, and the bigger the kind of like the nudge that so many people needed in order to make the leap, and come and do something like this, and change up their life and go and travel with a community of other people. Once they got there. They attributed all that to themselves, like not, you know, our ability to maybe help them expand their horizon a little bit, or provide the level of support and comfort that they needed in order to make the leap. So the exchange of value became murky, and increasingly murky longer than these experiences would last, you kind of go through this interesting arc, where right at the beginning of the trip, everyone's thrilled this new cohort is coming together. And people are meeting other people from all around the world and loving it. As time goes on. And those relationships come from something that's new to something that's familiar, people are scratching their head and saying, Well, next month, maybe I don't want to pay bloke that club kick to continue with my commitment here. Why don't you know, the four of us really get along really well? Why don't we go and do something on our own. So we knew that there was a, even though there were plenty of those folks that we could, you know, in theory go after as part of our target market segment that weren't affiliated with the companies that would be sending them over there. Even then, our product that we were offering wasn't the right product.

Grant  34:19  
Got it? Yeah, that's a tough reality to, to come to terms with. How did you and, you know, the team that you're working with, sort of have those conversations and was there a straw that broke the camel's back? Or was it you know, just a little bit over time, and then eventually you decided you needed to make a change?

Jamie  34:48  
Oh, it was a disaster. It was a disaster. I'd say like, six, seven months after launch. I pretty well made up my mind. That this model wasn't going to work, and that we needed to make adjustments. I had a co-founder, quite literally, I presented a plan that I wanted to pursue, as something that I thought would be, you know, more compelling based on what we'd learned up to that point in time, and I had a co-founder flat out refuse to, to do any sort of work, that wasn't this initial product that we had launched, he wasn't gonna work on it, we're free to do it, but he won't just complete like, you know, just ejected out of this thing. And it had a ripple effect, where all of a sudden, I think this this can happen, and it's easy to happen, it can easily happen in amongst startups, especially when they're new is you get into like politics, and you spend time dealing with people issues amongst a small team that isn't helping you get anywhere. And we got mired in that for some time. And ultimately, you know, it felt like what we'd started with in this camaraderie and a strong cohesive group that was going to change the world. And, you know, we were out there, we're speaking at South by Southwest, it's thought leaders in our industry, you know, we had such confidence in where we were going, and it seemed to just disintegrate amongst, essentially founding team in-fighting, and jockeying. So, yeah, that was tough. went through some difficult years there. But I think one of the best lessons that you know, for any entrepreneur is I took a lot of comfort in, you know, believing that there was a real problem here. People want to travel, it is difficult to plan that trip, or to get over that hump, to go and have these experiences, how do we help bridge that? How do we help people who want to do things go and do them? And there's a major, major market opportunity. And basically, what we said was, we're gonna hang in long enough to figure it out. And we're gonna bet on our ability to adapt. And ultimately, you know, stay in the fight. And I think that's like, the big, one of the biggest lessons that I've been able to learn has been, you know, you only fail when you quit, everything else is just a hurdle. It doesn't mean that you are Cavalier or, you know, shouldn't be thoughtful, and the choices that you make you don't, you know, knowingly run off a cliff, you have to analyze it as you go, but just stay in the fight.

Grant  37:39  
Yeah, I think that's maybe the thing that I would, I want to commend you on is so in part been kept abreast, as you've been on this journey, you know, you've shared updates along the way as just a friend who you knew also was interested in entrepreneurship and was doing a startup. And it's really been, you know, just inspiring to see how much you've been able to, you know, put up with and, you know, soldier on and, and learn from your mistakes and continue to pivot. And, you know, so many people quit. And like you say, failure is when you quit, and if you don't quit, and you just, when things don't work the way you want them to, your opportunity is to see that as a learning experience, and an opportunity to pivot into something new and better. And the number of times you've you've done that with GlobeKick and in leveraged, what you learned from in the past to make something new and better has been, it's been inspirational for me, and it's in part why I wanted to talk to you today and in part why I've been excited to be helping out with some of the the new stuff that go GlobeKick is up to today. So maybe this is a good opportunity to share sort of how the company ultimately has pivoted.

Jamie  39:15  
Yeah, thank you, Grant. I really appreciate that. You know, it's hard in those moments for other founders that are out there and you're going through it and struggling, it's hard the number of times I've heard of you don't get to this milestone, then you should take that thing out back and shoot it. You know, from people who are standing on the sidelines, they don't know what's going on. And you can't listen to that stuff. You have to trust your inner knowledge and inner knowing. And I think that's really bad advice and really ill you know, misguided advice from a lot of people who really don't know, you know, what your real goals are. And, you know, I think just just before transitioning into GlobeKick a little bit more, you know, that that's why it's important to come back to your why, you know, the downside risk of stopping seemed way too high to me to swallow even if the path ahead didn't seem particularly clear at the time. So you know, soldiering on becomes much easier when you know why you're doing it and you trust in your ability to make it happen. And, you know, so, yeah, so where we've now kind of broken through a little bit is, is, essentially, with GlobeKick, you know, we see a real opportunity to there's this trend that's occurring in many industries, you see it all over the place is paralysis by analysis, the information age has created an overabundance of options and choices for people. And we as consumers, all of us pay for some level of convenience to help me make this decision easier. If I go into a library, I don't want to have to it might have any book that I want to read, but sorting through all these books to figure out which one I really want to check out from the library is an overwhelming proposition, I need a more efficient way to get through this information to find what makes sense for me. And, you know, when I touched on earlier with GlobeKick, you know, it's about meaningful connections through travel. When we started looking at it, we thought, wow, I mean, think about the partnership that happens between a couple who chooses to embark on a lifelong journey together, whether they're married or not, you know, those sorts of deep experiences with one another, how can we help you strengthen those relationships through travel, and so honeymoon started to become very clearly into our focus in terms of wow, you know, we can provide, you know, hopefully make that trip of a lifetime, a life changing experience that people want to enjoy together, a lot less intimidating the plan, and a lot more fruitful for the couples themselves. So what we're doing with GlobeKick is, you know, essentially just a deeper level of personalization and getting to know travelers and then, you know, helping to essentially streamline the process and the more fun and visual way, so that travel planning, you know, is, you know, hopefully almost as fun as going on the trip itself. And we see an opportunity to do this not just in, you know, for couples, but maybe for the travel market at large as well. And it's just a, it's an exciting thing to be working on. It's the culmination of all of that experience that we've had over the years about how people want their own personalization, and trips, that you're just putting people into the bucket to try and satisfy all them in one fell swoop is not the solution. It's about deeper personalization, and connecting people with the places and experiences that are going to be best for them.

Grant  42:53  
Yeah, and as you transition from what has been primarily a service based business, to a product and technology business, what have been some of the biggest challenges so far?

Jamie  43:05  
Not knowing what I don't know. So, you know, I think that's a real challenge. When you do anything new for the first time, you can research and you try and learn and try and soak up as much information as you can from people who were the whether they're one step ahead of you, or 10 steps ahead of you, or have gone through the whole cycle, you know, many times over, trying to soak up that information. So you can make the best decisions for your business. Because ultimately, as a founder, you're responsible for those decisions. You can't outsource to somebody and say, Well tell me what to do. You have to ingest that information, and then try and make the best decision possible for your business by surrounding yourself with the smartest, most capable people you possibly can. So doing that, and something that's new, has been obviously challenging. I've learned so much about technology and product development from you, and the folks around me that have been invaluable. And it feels like a learning experience every day. But definitely, you know, in the back of my mind, I'm always thinking, hmm, is there something about this? I don't know, that could help me make a better decision. Because ultimately, it's all about decision making. And if I can be right, with my decisions more often than I'm wrong, I'm going to end up in a good place. And if the opposite is true, then I'm going to end up in a place I don't want.

Grant  44:27  
Have there been any resources that you found particularly helpful. I mean, having the awareness that there's a ton of stuff you don't know is the most important first step. Just thinking about someone else who's going through this, you know, I've spent my basically my entire career working in digital product design. So sometimes it's hard to put yourself back in the shoes of someone who's doing it for the first time. Have there been any resources that you found particularly helpful in the transition?

Jamie  44:58  
That's a good question. i can't pinpoint anything specifically but i will say that knowing what to what you want to listen to or who you want to model after and who you maybe can politely ignore because it's not the kind of business that you want to create is is maybe the most important thing in terms of sifting through information and figuring out what you want to pay attention to and what you want to discard and you know i give an example well a few people that i really have enjoyed learning from and have decided i wanted to continue to model after you know or like Naval Ravikant or Peter Tiel’s Zero to One. Some of these books have been very impactful you know the Lean Startup was very foundationally impactful for me and you know as you kind of you can get all sorts of conflicting advice like all you need to raise money or never don't raise money that's the stupidest thing you could do you know everyone's got an opinion and there's a lot of noise out there and there's a lot of people who are experts you know in startups but not like startups are so vastly different what kind of business are you trying to create is it service based is technology based are you trying to build the next facebook or you're trying to build a nice little side hustle you know like you can't take just some some advice that you read and say this applies to my business you have to be able to filter that to know whether it applies to your business so you need to know what you want to create and then you need to find those that that information that's out there that aligns with what you want to create and follow that and trust that and trust those people and it's not that this other advice is bad advice it's just if they don't have real knowledge of where you want to go and what you want to do and what you want to create then the advice might not be relevant and it's a dangerous spot to just take any advice that comes along from someone who's been there before but doesn't know enough about you to make a really meaningful recommendation.

Grant  47:02  
Yeah i mean that so directly ties back into one of the through lines here around understanding your “Why” like the “Why” of what you're doing is so important because then the “What” and the “How” can change and you've got your sort of got guardrails to understand like there are certain “Whats” and there are certain “Hows” that do not help me accomplish the the foundational “Why” of my business and therefore they're out of bounds or that particular advice from that particular source doesn't make sense for the type of business i'm trying to create based on my sort of underlying understanding of the sort of the purpose of the project in its in it's sort of foundation so that's super helpful which which also reminds me that you know i think one of the biggest challenges in very early on in my career before i got into startups i worked at a marketing firm that would go into established businesses and sort of tried to apply and work with the sort of founding team and the executive the c suite to go through a sort of workshop to define what is the company's “Why, How, and What” which in retrospect is just such a difficult exercise to do retroactively like when you've been operating a business for decades which i think is why it's so helpful if you're doing a startup if you're at the beginning stages of your project or your business like you might be wrong and it might change but it's very helpful to define those things upfront and and starting in the middle like your “Why” like why do you want to do this and the better understanding you have of the “Why”, it puts you in a position you can take a stab at what the “What” will be and how you'll go about doing it and those things might be your pivots you may change over time as we've heard you know directly from you Jamie's like for GlobeKick you had a core “Why” and then you were able to try something out in the market really give it a solid try and see if it could work and then with clear eyes acknowledge when it wasn't working sort of recenter to that “Why” and pivot into something else that could accomplish that same goal so i think it's just so important for people to take the time early on to know what it is that they want out of what they're doing, otherwise you can find yourself way off course very quickly.

Jamie  49:27  
Very well said, very well said. I completely agree with that it's for anyone that any the Simon Sinek It Starts with Why it's such a great book i've revisited it you know frequently and i think if someone hasn't read it yet particularly as a founder it's such a foundational book as well i think to begin with.

Grant  49:47  
So one thing that you said that I want to revisit is when you were talking about your sort of introduction to entrepreneurship specifically when you graduated from college, you moved to China, you equated the uncertainty of that experience of not knowing what you're going to do with sort of your real first experience with entrepreneurship. And so I think it's an interesting way of, and I know you weren't necessarily defining entrepreneurship that way. But I think it's really important to acknowledge the uncertainty because it is, at least in my experience, embracing that uncertainty is sort of a prerequisite for, for taking the leap, doing the startup, you have to acknowledge that there's so much you don't know yet. You don't know where you're going, you don't know where you're going to end up. There's no map. You just have to kind of embrace it and get started. Maybe if you could tell us a little bit more about like, how do you come to terms with that uncertainty? How do you become comfortable with it? How do you move forward? Even when there's so much ambiguity?

Jamie  51:00  
Yeah, that's, that's really interesting. That is really what it is. And so much for me that it boils down to it's part art, entrepreneurship, to me is part art, part science. And again, it very much depends on what you're trying to build out what your goals are with it. If your goals are just to make, you know, some quick cash to support yourself, or if your goals are to do something more artistic, and do something no one's ever done before your goals are to try and change the world on the largest scale possible. All of these paths require a level of uncertainty and ambiguity that you have to navigate. I think it was Ben Horowitz in the Hard Thing About Hard Things, I thought, when I read that book, and heard his message around, the hardest part about being a founder is managing your own psychology. And I thought that that was a very apropos and salient point. Because I'd say managing, you know, it's very difficult, you're constantly, you have to figure out how to train your mind in order to make good decisions. And for me, meditation has been the most impactful way to help me do you know, tame that monkey mind sleep well, at night, I maintain, you know, the level of confidence and level headedness that I need to continue on. But there's things that you can do or not do to help you manage that psychology, things like going into debt with your startup, very much increases the pressure, and makes the psychological burden of dealing with that uncertainty that much more challenging. Not having good people around you, and feeling as though you're going at it alone is something else that increases that pressure. You know, so having some semblance of like stability and trying to make, you know, sound decisions, knowing that you don't have you know, in in the startup, it's never, you're never gonna feel like you're on firm ground, it doesn't matter whether you have, you know, zero in the bank account or a million in the bank account, you're always the problems just get harder and harder and harder. It doesn't get easier as you go on. And so you always need to try and be setting yourself up to not take on more, knowing that whatever you're working on here is going to have plenty of challenges. And let me you know, in hindsight, moving to China, and trying to navigate that in Shanghai and take on that uncertainty while trying to start a business was just like an absolute pressure cooker. One of them in isolation, it's fine. Putting all of them together is much more challenging. So trying to remove variables, so you can stay if your goal is to build something meaningful for whatever your goals are, I'd say removing distractions or removing variables as best you can, is and if that answers the question, but that's how I interpreted the question.

Grant  53:55  
Yeah, no, for sure. That's, that's really good advice. And I think sometimes you're not completely in control of all the variables, but there are almost always some variables that you are in control of that, you know, you can make changes in your life to make things easier for you. And like, you brought up meditation, which, which can be just so powerful for people but you know, things like just making sure that you're sleeping, making sure that you're eating healthy and exercising. I think that sometimes there's an appeal. And that there's like an allure to, hey, I'm at the beginning stages of a startup, I'm going to work all the time. I'm like, never gonna sleep. I'm gonna ignore everything else in my life. And ultimately, I think that's detrimental to the startup, you know that there is a point of diminishing return. And there is a point where, you know, maybe you do need to make some sacrifices early on, depending on sort of what you value. And what's important to you, but being really wise about some of those, like foundational things that can impact your mood and like you said, your psychology, like, like rest and food and the meaningful relationships in your life outside of work, there are certain things you don't want to compromise on too much.

Jamie  55:21  
Couldn't agree more if this might be a little like fear of it being interpreted as woowoo or too meta, you know, I do think the external world responds to whatever's going on inside. So if you're in alignment with yourself, you feel good about yourself, you're taking care of yourself, then you carry that confidence in the world. And the world responds accordingly, new opportunities come into your life, new relationships, or improvements in your current relationships, everything gets a lot easier when you start with with this, and you can control this, you can control your mind, you control your body, you can eat healthy, you can exercise, and I completely agree with you long term, it's the best thing you can do. There are times you have to toggle up and maybe go into sprint mode and hustling, grind for a while. But doing that end over end is long term detrimental without a doubt. And I know that because I've done that. And I've seen where that's gotten me. And yeah, that's, that's a lesson learned the hard way for me.

Grant  56:24  
Yeah, just to close the loop on that. It's so interesting, too, because I think the biggest mistake that people make is they forget, as you mentioned, that decision making is what it's all about, it's all about making the best decisions as frequently as possible, you're not always going to make the right decision. But it's about sort of increasing your percentages of good decisions. And all of those things we talked about, when you start to lose sleep, or workout, or like the relationships within your co-workers and within the company are bad and you stop, you're not trusting each other, and you're just your decision making goes down. And that's, that's you may you could work 90 hours a week forever, if you start making bad decisions, it doesn't matter. Obviously, it's going to end up badly. So obviously, this is a, you know, a podcast, a conversation, it's part of a larger project that I'm working on called Makers Inc... And it's, it's all about startups and really, my goal with the project is to share my experiences, my skills and, and provide access to resources that I wish I had when I was first starting out. And so through conversations like this, and with other people who've, you know, been through different things and have learned from their experiences. Hopefully, people will find it valuable. So I really appreciate you taking the time to share your wisdom, share your journey in entrepreneurship. And I think the most exciting thing about it is it feels like it's just you know, getting started, there's, you know, a bright future for GlobeKick, I'm excited to share more broadly with the channel here. Some of the updates that will be will be rolling out pretty shortly on the goal of GlobeKick. And I'm curious, as I'm also at the beginning of starting this project with Makers Inc. I'm curious if you have any advice for me?

Jamie  58:56  
First of all, thank you, I've learned so much from you already. And your entrepreneurial experience should not be discounted in any way shape or form. In addition to your product design experience. I've learned so much from you, I'd say the advice that I have for you and really for anyone starting out and building something new. And that's taking the leap in is taking action steps towards that not just thinking about it. You know, it's kind of funny, I've heard this so many times and not applied it. And when I've applied it, everything's gotten so much easier and that is knowing exactly who your customer is. and speak to that person. The ideal target market is a target market of one. What are the defining characteristics of you know, who is Makers Inc. for is it for the person doing the side hustle? Is it for the person that has huge dreams that wants to you know, start out in a very low cost kind of way is it, you know, for someone else entirely? It can satisfy all of those segments. But knowing which one you want to, you know, truly go after first has brought so much clarity when I've applied this, it's I know it's, it sounds very simple, but the biggest thing, start with, you know, the smallest little segments and go really be the best you can for that one particular segment and everything else becomes so much easier. I've learned that one the hard way more than once. And so I'd say that's my piece of advice for you as you're starting out here. And continuing to hone in on on who's going to be getting the most value from Makers Inc.

Grant  1:00:41  
Absolutely, that is great advice and something that I know I need to continue pushing on. So I appreciate you sort of reinforcing that. Where can people find you online, they want to check you out?

Jamie  1:00:55  
Oh, I'm like a hermit there. Trying to stay off that boat. I'm on LinkedIn. And Jamie at GlobeKick .com is probably the easiest way to reach me. But I go on and off Instagram. I haven't dabbled a whole lot on Twitter at this stage. And I haven't really spent a ton of time on some of this other stuff. I'll go through these dark periods where I just, you know, it just doesn't feel like at that moment in my life. It's adding a whole lot of value. So I just kind of set it down for a while but LinkedIn and email are pretty tried and true.

Grant  1:01:32  
...and GlobeKick.com is the best place to see what you're up to on the new business.

Jamie  1:01:40

Grant  1:01:41
Awesome. Well, Jamie Debole it was awesome. I really appreciate it man.

Jamie  1:01:47  
Thanks so much for having me Grant. I really enjoyed this.

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