Don't Get Ready, Get Started: Real Entrepreneur Stories That Will Inspire Your Next Move

What if the biggest risk isn't starting your business—but never trying at all? In this candid conversation, three seasoned entrepreneurs share the real stories behind their leaps into business ownership. From Aimee's agency escape that doubled her income in week one, to Jacob's accidental 13-year venture that started as a Monday night party, these aren't polished success stories—they're honest accounts of fear, failure, and the messy reality of getting started.

If you've been stuck in planning mode, overthinking your next move, or waiting for the "perfect moment," this conversation will give you the push (and practical strategies) you need to finally make your move. Watch as they tackle the biggest fears holding aspiring entrepreneurs back and share why sometimes the best business opportunities are hiding in plain sight.

Key takeaways: Why you need "just enough data" to start, how to reframe risk when leaving corporate, and practical tips for creatives who hate self-promotion.

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Transcript

Parker Gates: all right. Y'all, I'm gonna go ahead and get us going for those of you that I haven't met yet. My name is Parker Gates, and I'm 1 of the team here with the starting block crew. I'm joined by my good friends and colleagues, Jacob and Aimee, and Jesse and Daniel and Liz and you know I was thinking about that this morning as I was walking my dog. I was like, man. What a pleasure it is to like build stuff with friends, you know, like you know, we've been working together, you know, for a while now, and it's always fun like with us, like it's like coming up with new ideas and finding new ways to execute on things like it's always fun. even in the like, the midst of like not knowing what we're doing all the time, and like having a hard time, like, you know, launching an Ecom brand. Basically it's still so much fun when you do it with like fun and smart people. So anyway, I just wanna like, give a nod to my colleagues. It's so cool to get to work with you guys? so we're gonna do a couple of things today. The title of this podcast is, don't get ready get started and which a lot of the people on here know came from one of our mentors a guy named Perry Claiborne. When I was trying to give him some excuse to not get started he's like, Hey, man, are you building the thing yet? And I was like, man, I'm thinking about it. And he, kinda yeah, put me to put me to work real fast. And so so we have a couple of fun stories about that. Jacob's gonna share a story. Aimee's gonna share a story about getting started. Then we'll take just a couple of minutes to talk a little bit about this course that we have which is on sale for 50% off right now and then. And then we want to do some QA. Or maybe even like, hear little bits and pieces of your own personal stories. So hopefully, this feels more like a dialogue and less like us talking at you, which is maybe not so interesting. So so I want to kick it off. I want to hand it over to my friend colleague Aimee, who's gonna share her story of getting started.

Aimee Romero: Hey, dudes? Yeah. So thinking about what I was gonna share today, I think I I actually spend a decent amount of time getting ready. And I thought about kind of the the last big jump I made. So I've been with love and science now started that 13 years ago, and the story of like getting that off the ground is You know, I didn't really see myself as an entrepreneur. I really wanted to just build stuff and that like building stuff. It was really powered by just a desire to solve problems. I really wanted to capitalize on opportunities, get rid of obstacles, and I was in this agency, and it was a good agency with good people. It was like a great place to work. I had fun, cool projects. But I just kept bumping up against friction. I would want to do things differently. I would see like opportunities. I would see issues. I would see how we could improve, and it just felt like there was no path for me to do that, and I but I wasn't sitting back on my heels. I just kept pushing, kept pushing, and friction just kept increasing, and it was starting to get like pretty hard to work there. As the friction increased, I started just doing the basic math and being like, Okay, well, they're billing $26, or I'm getting $26 an hour. They're billing $165 an hour like there's not a ton of. There's a lot of margin there. I could be doing this work like fewer clients, fewer projects, less time, and still be able to make up that money. So that's in the back of my head. Fast forward a little bit. The agency ends up hiring this outside consultant to come in and assess the company. And this guy. He interviews everybody. He gives everybody personality tests, I'm thinking. Okay, I'm on my way out like once they figure out my personality is actually I'm out of here, but he ends up telling them. give that girl a department she can take you guys like she can keep you moving. Keep you going forward. And there was all this discussion. I was in all these like kind of uncomfortable meetings with supervisors and stuff. And eventually they tell me, hey, you know, we've decided you could take 10% of your time to pursue these things this optimization desire that you have. And by that time it was just over for me. And I thought, I'm going to use 100% of my time, like No, 10%. I'm going all in like, I am going to do what I want to do 100% of the time. And it really like. It was rocky. When I 1st kicked things off I experienced issues I had no idea were coming, but at the same time I've never looked back, and those 1st few contracts that I got the agency that I left was one of my very 1st contracts. People that I had engaged with in my business just as I was working at this job were 1st contracts, and I went back and did the math yesterday, and those 3 contracts equated to double what I was making just those 3 contracts in the 1st like week, or something of like launching the thing. Yeah. So I mean, that's that's pretty much the story a little bit of analysis for me. The big thing is that I want to analyze, like to get an answer to something or to find like what I'm going to experiment on. It's easy if you just spend a lot of time thinking about it, thinking about it, to to stall. But I took in the data a small amount of data that I needed to make a decision to clarify something. And I and I moved from there.

Parker Gates: Aimee, I love that. There's there's a couple of things I'd love to like just kind of like I don't know double down on or follow up on one. Is this like, I think everybody on this call. Everybody in the world has run into that friction at you know their organizations, and that we all have that same kind of ideas like man. I could do this better than than these guys right? Like there's there's always that idea, but you know, rarely do people actually jump off and go try it right? Some people decide to stick around and try to make it better. But we all encounter that friction. It's like, so there's like that. There's that one decision point, you know. Which way am I gonna go? That's where the the path split. The other thing that I I appreciate that you said is this idea of like having one piece of like objective or outside validation about your capability. And it like. How important that can be, how important it can be for us to receive it, but also like how important it can be for us to give it to other people. A lot of times in in my job as a coach, I end up telling people I'm like, Oh, my God, you're so smart, or you're so creative, or you're so like, capable. And people are like, really. And I'm like, Yeah, dude and so, you know, sometimes we just we don't always have that mirror in front of us, and so to have somebody come our way and give us that little piece of objective validation that yes. you're smart, you're creative. You can totally like, do good stuff like that's all it takes to to really launch us? And so yeah, I just really love that. The last thing I would love to say is that is that like in the means of like don't get ready to get started. Was this idea of like, I had just enough data. It was just enough. It wasn't like a mountain of data. I didn't stop and research for 6 months about like what I was gonna do. I had just enough, you know, analysis and data. And I was ready to move on. So yeah, that was great, Jacob, what's up.

Jacob: Aimee, yesterday, when we were kind of running through some of this, you you mentioned something that I thought was really interesting about the way you evaluated the risk, like the risk of being employed versus the risk of that just want to hear you say it again, because it was awesome.

Aimee Romero: Yeah. So for me, a little about of that. Analysis, like short bursts of analysis, was just about de-risking, or like evaluating the risk. And when I thought about it you know, in my opinion, like so people will tell me all the time like, oh, I can't believe you had business for 13 years. It's a big deal whatever, so hard to keep a business running, and I think, like it's way easier for me to keep this business running than to keep a job like somebody could literally fire me tomorrow. And I have to start over, or I've built this thing that like I can kind of point at stuff I can figure things out. So to me it seems less risky to have myriad clients, and like people who I'm engaged with at this level than it feels like to have a job that I could just get fired from. And then the other thing that I talked about yesterday with the team was just like just that, like that cascade effect of like, what's the worst that could happen? And just looking at it, taking a minute to look at it and see what that is, and either say, well, that's not so bad or well, here's how I'd handle it, and it just kind of gives you a step, and and like in fairness, like a thing happened to me when I launched that business that never showed up on my cascade of like. What's the worst it could happen. There are always surprises, but there's a lot that you can do to just. I guess, mentally prepare, and like de-risk, is almost more like what's in your head than what's actually on paper. And I, personally, just really believe that you can find more potential like your potential can be realized more easily outside of someone else's system. And I think when you're outside of someone else's system, it gives you some flexibility to pivot and follow the opportunities, fix the problems. It's the for me, at least, it's the external system that, like I can't judge. I can't always fully judge that, and I certainly can't control it.

Parker Gates: Yeah, I I had an old boss guy named Robbie Reimer when I was in the healthcare world that always said that to me he was like, look, man, sometimes you gotta go work down the street for us to realize how good you were here. And that's certainly been true in my life the other thing, and I'll steal Jacob Jones's line real quick. The other thing that I don't know why I always call you by your 1st and your last name. I've been doing it for like 15 years, anyway. The other thing that I love that Jacob always says is like one of the riskiest things that you can do is never go try your dream like, never go try the thing that you've been thinking about for a long time, and then be. you know, 98, laying in bed about to die and think, shit! I kind of blew it so. That's probably one of the biggest risks that we can take. So all right, if you have questions or comments for Aimee's hold on to him, drop them in the chat. Just wait a minute and we'll come back. But I wanna make sure that we get a little time for for Jj. To share his story, and then we'll do a little QA. And open it up a little bit. After that. Jj.

Jacob: Yeah, I wanted to share. I've been thinking about this kind of my entry way into entrepreneurship. It's a little bit about getting unstuck and getting started in kind of my own version. So I moved to Nashville in 2,007. I was in my early twenties, and I was a musician. Me and a buddy were roommates, and we were both putting out albums. And so we had this idea of starting a record label. We just wanted to control our own stuff, have a common flag to fly and ideally grow the record label as a business and sign other acts and everything we just moved to Nashville, after all, just seemed like a great thing to do. So we get going. And like we get the brand together, we get a website we get. He's a great designer. We get all the all the elements, and we're off and running. We both have albums. We put them out. and we kind of immediately come up against a wall of we don't know booking agents or radio promoters or distribution, or we don't have any money. So it was really hard. It was fun. But we weren't really getting anywhere. We were both playing shows and doing our thing. But we really wanted this label to be our common thing. And we're just like, after a year or so or 6 months. It's just kind of stuck in a way that like didn't matter that much, because we both worked at restaurants, and we were both kind of screwing around. But we just kind of it just kind of just didn't really work and kind of realized. All right, if we're gonna make this work, we're gonna have to, you know, maybe get some help or figure out how this industry works more than just fake it to you. Make it kind of approach. In the meantime he and I had started a party that has nothing to do with this business. But it was still him and I and this party was on Monday nights in Nashville, and then we both have a big love for old soul music. So like sixties, motown stacks, chess and so we launched this party at our at a venue down the street. And you know, 1st night 10 people are there next week 20 people are there and 50 people. And we're like 6, 8 weeks into this party, and there's hundreds of people at this thing every Monday night. We still don't make the connection that, like, maybe this is what we should be doing. We're still trying to build this record label, which was called Electric Western Records, so fast forward a couple of months. This party is just outrageous, and it's so it was free, by the way, and we were just doing it for the fun of it, and make some tips. The party gets so crowded that we decide to start charging $3 at the door just to piss people off so that some people won't come in, and it will clear room on the dance floor because people were getting upset and saying, Yeah, I can't even move in here. And so we charge 3 bucks. And then all of a sudden there was like Eureka like, Oh, my God! I just made more money tonight than I do bartending down the street, and I had been really looking for a way out of the bar industry, because I seen what that can do to you after a while, and I didn't want to do it for the next 20 years. So then I immediately got the idea of like, let's charge 5 bucks, because if you look in this room and you're not willing to pay 5 if you're willing to pay 3, then that's on you, because you can see this is a really good time. So all of a sudden we charge 5 bucks. Nobody cares. And then we just have a conversation. One day we're like, instead of electric Western records. Let's make it electric Western productions. and we just became promoters. We still had our music, but we had already started this thing without knowing it, and it, like we had struck a nerve at the Zeitgeist at this right time and place, and we just weren't paying attention to it. The second we started paying attention to it and feeding it the same amount of creativity and energy that we had been feeding the label side. It just exploded. We did that party for 13 years every Monday night somewhere between 4 and 800 people came. Every Monday we ended up doing festivals, Bonnaroo traveling we finally shut it down. When Covid hit the building was hit by a tornado, and then a week later, Covid hit so that the double whammy we were like, you know, I think I think we're good. We aged out but you know we will look back on that. And we had put hundreds of thousands of people through that door, and we had Dj. Dozens of weddings, of people who met at the party, and, like all these crazy things, happened from it. And then I ended up launching a marketing agency based on the reputation of that party, and it led all these different pathways which led me to media production, which is how I met Parker, and then eventually led me into real estate, which is what I do now. And he's had similar experiences, and we're still super close friends. And I just I just want to tell a story to illustrate that sometimes a thing that gets you unstuck is right in front of you, and you may have already started it. Even if you don't realize it.

Parker Gates: Dude. That's I'm always such a big fan of that story. I've heard it several times, and it's still like like I'm still like tuned in like, I don't know what's gonna happen or something like that. It's just like it's a fun positive story. And and I'm just like catching a couple of things here in the chat, like Emily said, Yeah, watch out for that unexpected prototype. And it's so true we talk about like stumbling into things accidentally, the accidental prototype, right? Which happens all the time. And there's so many cases where sometimes we'll just tell people like, even if you don't know what to build yet. Go to the prototyping table and just start looking at materials and start to build and like, watch what happens. It's like. There's something like, even if you can't consciously think like your subconscious is like jamming on something, and your hands are doing another thing. And then just magic starts to happen in a really beautiful way. I think that there's this. there's this myth that a lot of us suffer from right this like this idea that like, Oh, I have to have a really clear vision of exactly what's gonna happen. And then I'm gonna go build it. And then it's gonna be successful. I certainly had this. A couple of the guys that are on this call were here this night, but I had this idea of like I wanted to be a writer. I wanted to write a book, and somebody asked me, oh, man, what are you gonna write a book about? And like, you know, what's it? And I was like, oh, well, I mean, I'm not really sure I'm kind of like thinking about it. And then, as soon as I get it all like figured out in my head. I'm gonna I'll sit down and, like, you know, put it on paper. And he just started laughing. and he was like, no dude. That's not how it works. You need to go get to work right now. The 1st draft is gonna suck. It's gonna be awful but you need to go get it done right now. That's that's your start. And and sure shit, that's exactly what I did, and and he was absolutely right. So anyway, so I love this. I love this idea of like getting started doing the like kind of like following the energy following the flow into into doing something you like. And then you have no idea how it's gonna turn out. But the fact that it was like something you loved, and it was with a good friend like. you know, like it's hard to lose. With that, you know, like it's hard to. It's hard to go bad with that kind of feels like you and I get started with starting block. Actually, same kind of same kind of thing alright. So here's what I'd love to do. I'd love. We have just like 10 min left. I'm gonna tell you a little bit about starting block here in a second, and this like cool cohort that we're offering this like free cohort that we're doing for for new startups, new entrepreneurs, or early stage entrepreneurs. But I'm curious. Does anybody have questions or comments, or like similar experiences? With Aimee and Jacob that they'd be willing to share or talk a little bit about. I know a lot of you do, because I know most of you. So I'm curious. If anybody has anything that they'd love to, to share or to ask.

Question: How do you overcome the financial fear of leaving a steady corporate job to start your own business?

Jacob: You know. Go ahead! Yeah, that's that's that's super solid. I I just will add on to it and say, kind of like the way Aimee views it, I mean, you have to be prepared. Obviously, in math is math. But You can always go back, you know. It's like, I don't know when you do that. What's the worst that could happen? Thing I mean, okay, worst that could happen. I can't pay my rent or I can't. I mean, that's not great. But like if you, you can always try and then go back to the job market, I mean, that's my opinion. I guess it's not. No decision is so so final that you've abandoned all the other options. But if you don't ever try and you have, you're one of those people that has that kind of voice in your head that you want to try. Then you've eliminated that option permanently, whereas if you just try it once, you still have all the other options on the table.

Parker Gates: Yeah, I just wanna like, take this opportunity to say that the number of failed business opportunity or like failed businesses that I've tried outweighs the number of successful businesses I've tried. I just want to be really clear about that. There's 5 or 6 things that did not go well. But the things that did go well went well enough to get me through all of the all of the little tiny fails like they were inconvenient more than they were like. A failure, I think, is is the thing that I would say I love. I'm just gonna like Mark. Mark. He has such a beautiful voice, can you just share your your questions here.

Aimee Romero: I have a rich friend who I periodically ask, hey, man, if everything really went South, would you pay my mortgage for a couple of months, and and I pressure him until he says yes, and that helps me a little bit.

Parker Gates: Awesome. Rich friends are great. I love that.

Aimee Romero: He's never had to pay my mortgage, but I think some of it is just like that that the potent fear, if you really look it in the face and say, Well, what could I do? There's so many things that you could do. It's like it just really. That de-risk thing is, is always kind of there.

Parker Gates: Totally the safety net, like always knowing that there's like a a level or 2 of a safety net is always kinda nice. I also. Yeah, I mean, Emily again, just pointed out something like really great, like layoffs happen all the time. Our friends who are, you know, employed by corporate get laid off all the time. There are times when I feel like being an entrepreneur is actually more secure than working for a big organization, like A, you know, especially in tech these days. So more and more, all right, do we have? I think we have time for, like another question. Other comment. If anybody's got one.

Question: How do creative people overcome the fear of marketing themselves and their work?

Jacob: I've got. I've got one story that I've just seen in my own life from afar, that is, that has astounded me. About 3 years ago my wife started a business. She's she's a home stager and interior designer. and she's just the exact same thing she hates promoting herself, hates talking about herself, very introverted, doesn't like to put herself out there. And I definitely thought, like, it's gonna be a problem. You're going to have to pitch yourself a lot, but the work has just stood for itself, like she just got up there started working, and I would say things like you should get on Instagram and share these pictures and share this, and she would when she had time. But she eventually, you know, through networking and just existing friends she got so busy, and then she and she was. She's really dedicated to what she was doing 3 years down the line. She's swamped at all times, and has literally, I don't think ever promoted herself, she went on. A podcast once was terrified, the shit out of her. And that's about it. And so that's the only that's an example I've seen just with my own 2 eyes of like. Sometimes it's more what you do than what you say. Get you further.

Aimee Romero: Super speed, super speed thing. My band wasn't Aimee Romero, it was Merrill and the broken bones, because then I could be like this band is cool, and I genuinely thought the band apart from me was cool, and it made it easy. Love and science is not Aimee Romero consultant, and I think my team is amazing. It makes it easy for me to talk about them. But the other thing that works even before I had, you know, band team. Whatever is like the work matters so much to me. and it's so easy to talk about where you want somebody to go, how you want to see their trajectory that that can take away all of the like agony of being like, Hey, I'm really pretty good at this. It's like talking about the problem. And I mean, everybody's got a different like way of selling. But talking about the problem, talking about like what the solution is like that's super helpful, and something we stand by also is like, do stuff for free. When you do stuff for free people will talk about it. You know you do a good job. People will talk about it, and it kind of gets into that expansion mode that Jacob's talking about.

Parker Gates: I'll end with this the the thing that I'm also super allergic to to sales people in general like I don't like being sold to. So, therefore I'm terrified of being like in any way associated with that kind of that kind of behavior. Somebody once told me that if I do something that is actually valuable for other human beings, I'm denying them the opportunity of impact and getting better if I don't open my mouth. And that really struck home. It's almost like I'm holding the antidote to some for somebody who's just been bitten by a snake, and I'm not saying anything about it and I don't know. Maybe that's taking myself a little too seriously. It's fairly dramatic, but at the same time it's got a good point to it, you know. So if I feel like I'm doing really good work, and I'm not just trying to make a buck. Then I should. I should say that thing out loud, you know. So alright, guys, we're right at the end of our time here. I just wanted to like, take a moment to talk a little bit like, really quickly, about this this thing that we have. So, we built this online course, Jacob and I made it over a year ago. It's called Starting Block. It's for brand new, like aspiring entrepreneurs or early stage entrepreneurs. It is a like a super practical, no fluff online course, you could literally watch the whole thing in like 45 min. But we assign homework for each module. And so there's like work to be done if you want to do it. It's lots of personal stories of both of like success and failure. And I think we talk a lot about our mindsets as well. And so anyway, we're offering that for like 50% off. So it's like $49. I don't know whatever half of 99 is it's that? So so if you're interested, if you know anybody that's interested you should ask them to buy it and then the other thing that it's maybe even cooler is that we're prototyping a 60 day cohort for new entrepreneurs for anybody that's launching a product or service or a business we're doing a free, completely free, 60 day cohort, all of us experienced entrepreneurs, serial entrepreneurs. We're doing weekly calls and then income in addition to like some asynchronous support. For 60 days, and that is to help people get unstuck to get somebody launched out into the world. You know. sharing war stories and but also like tips and tricks. There's a awful lot of knowledge in this group. We're also big fans of this idea of like building with other people right like doing it with a group doing it with a community and but not a giant community, not like 300 people, but like 7 people or something like that. We think that there's a lot of value in that. So if that sounds interesting to you, or you know somebody that could really benefit from being in a cohort, tell them to buy starting block, and then they can join us for free for 60 days. Team! Have I missed anything? I'm sure I have missed something. But did I miss anything.

Aimee Romero: Just build like what starting block is like that course, it just kind of covers a lot of the basics and personal story. When I launched my business I didn't know a lot of things that came back later to hit me, including like not having a business license for 10 years or something, and having to do some weird negotiations with the State. So like just getting some of that dumb stuff that takes up an enormous amount of your mental space, or can hurt you later on, like just getting it out of the way. I wish I'd had it laid out like this like this is what I was always asking people for is like, I just want, like a workbook that has, like the set of things that I need to do that are not exciting, you know. Not all of them are exciting. A lot of the stuff is like cool and like exciting, but it also covers the just junky stuff that like stops you. Those obstacles are like, well, but I actually don't know what an Llc. Is like. It'll just wipe them out.

Jacob: I just add on and say, you know, when I think everyone involved from Parker and myself, love and science, like we all kind of come from this sort of punk, rock background and entrepreneurship has made a huge impact on the amount of freedom we've been able to have in our lives. And so when we built this thing, it was like, how can we teach people how to go from 0 to one? And then, after we made it, and we were promoting it. It was like, What's the how can we create a community of people who are also their endeavors are allowing them to live the lives they want. How can we share in that? To lift each other up and just provide a community to travel along with.

Parker Gates: Yeah. Yeah. Well said, well, said, you guys, alright gang, we're 3 min over. I knew that we were gonna blow our time by a little bit. That's all right. If anybody wants to stick around and chat a little bit more, feel free like we're just gonna hang for a minute, if not, thank you so much for joining us. This was our 1st one. I don't think we blew it that bad, I think. We there's no like major mistakes, no blood or anything like that. So anyway, we'll be back next month. Look forward to it. You're probably gonna get a bunch of emails from us. Just ignore them. That's cool. All right, everybody. Thanks a ton. Y'all we'll see you later.