Episode Transcript
[00:00:00] Speaker A: Foreign.
[00:00:05] Speaker B: Welcome to another episode of the Worst Advice I Ever Got. I'm your host Sean Taylor, along with my trusty producer jb. And today our guest is Jeff Hillemire. Jeff is a serial entrepreneur, a TEDx Atlanta speaker, and the author of the book Dream Small.
He's also the co founder of 48 and 48, a non profit that brings volunteers together to build 48 websites for 48 nonprofits in 48 hours, unbelievably helping small organizations scale their impact. Jeff, thanks for joining us today.
[00:00:42] Speaker A: Thanks for having me, Jeff.
[00:00:44] Speaker B: I'd love to know about the worst advice that you ever got.
[00:00:47] Speaker A: The worst advice I ever got was to dream big.
[00:00:50] Speaker B: Okay. I'm having trouble. I mean, when you wish upon a star, big, hairy, audacious goals, you know, what am I missing here? What's wrong with dreaming big?
[00:01:02] Speaker A: Well, the funny thing is, I don't know how many of your interviews have, have gotten the advice from themselves, but it was me that kept telling myself.
[00:01:11] Speaker B: You'Re the second one.
[00:01:12] Speaker A: Okay, all right, all right. I just, I just kept feeling like I had to swing bigger and, you know, climb a bigger mountain and nothing was ever enough. And, you know, I got to a point, I was around 35 years old and I was just like, what am I doing? What am I chasing? And so, you know, for me, it was this, this overwhelming feel competing with everyone in a race that I conceived of only in my head and not feeling any satisfaction from that.
[00:01:37] Speaker B: Hmm. Well, let, let's get into some of your experiences that you were feeling over that period of time you just referenced on Dreaming Big. Like, what were you struggling with? What were you going through?
[00:01:48] Speaker A: The earliest example I can think of is I played tennis growing up and played Division 1 tennis in college. I left high school thinking I wasn't that good at all, that, you know, like, I've got so much I have to do to improve. But I was ranked 20th in the state. I mean, there were only 19 kids better than me in the state of Georgia. But all I could think about was how much better that guy's backhand was. I could never feel good about what I had accomplished. So it's, it's when I look back and I'm like, gosh, I was grinding so hard. I was, I was trying to beat everybody else and never really feeling like I was enough.
So I think, I mean, it started when I was younger, oldest child, maybe a lot of oldest children feel this way, but I think it just kept growing and growing until I got to, you know, after I'D sold two businesses and was like, why am I not happy?
[00:02:35] Speaker C: So during that business time, when you're sort of like you're growing, what kind of. It seems like you're seeing success, you're selling two businesses. What, what, what's that part of your life look like?
[00:02:43] Speaker A: So it took us 10 years to sell the first business and then five years to sell the second. I recognize somewhere in there that I was doing a very poor job of pausing, bringing my team together and celebrating we would have a big win. And it was like I was already onto the next big thing. I feel like I probably wasn't as good for my team because I was constantly pushing, pushing, pushing. I certainly wasn't as good for myself. And honestly, all that extra work I was doing to get incremental gains was keeping me away from my family.
[00:03:12] Speaker B: The pitfalls of dreaming big, the burdens that can come from that.
[00:03:15] Speaker A: Yeah, I think one of the things I've realized is that dreaming big out of the gates can actually stifle people from even trying to get started. And when I talk to other people who have dreams and ideas, they just feel overwhelmed by just getting started because they start with such a big, oh, I've got to do this big thing. And it's like you can pare that down to, you know, in. In startups, we. We say minimum viable product, but maybe it's minimum viable dream. Like, what's the smallest you can get this thing to then get started? And that's when you start to feel good about your life and feel like you're doing something important when you're able to get started on the thing that's going to bring you joy. So the pitfalls I talked about are you're never satisfied. You're pushing people around you too hard. You're pushing yourself too hard. Stress can build up, anxiety can build up.
And I just always felt like it had to be bigger and better. And I think the main point is I didn't have a reason for that, just because that's what society was telling me.
[00:04:18] Speaker B: Yeah.
[00:04:18] Speaker C: So it was an opposite true, you know, with Dream Big, Dream small, the.
[00:04:23] Speaker A: Opposite in terms of the advice of I don't.
[00:04:26] Speaker B: Is that bad advice too, to dream small? Is it. Was it like Mama Bear, Papa Bear, just right? I mean, where's the right place to dream, Jeff?
[00:04:35] Speaker A: Yeah, I. I like the idea of starting small. I've always liked. REM Is one of my favorite bands, and they have a song that's called Begin the Beginning, which has always been one of my Favorites. And I don't even know if that's what they mean in the song, but to me, it's like, you got to get started. So dreaming small allows you to start.
And, and so that I think is important. Certainly you want to have aspirations. You want to say, okay, this is what I'm working toward. But it's, it's the getting starting and not feeling overwhelmed by this massive thing you're trying to accomplish. Sort of put that to the side and say, okay, yes, I want to build something great, but how do I get started and feel good about the next six months, the next next 12 months? And I think that's where people get tripped up.
[00:05:18] Speaker B: Yeah, I get what you're saying. Like the thing can be so big, so hairy, so audacious to, you know, borrow from the BHAG concept that maybe you can't even get going. Am I hearing you correctly? That start small, but ultimately you will accomplish things bigger because of that? Like surely. Yeah, you, you want to have significant impact. So you're not saying try not to have significant impact, are you? I mean, just help me carve this up a little bit.
[00:05:47] Speaker A: So, so I'm saying a couple things. I'm saying, in most cases, the only way to have significant impact is to start small and don't become overwhelmed by that. But also when we're talking about people chasing their own personal dreams and, and, and trying to do work, let's say that's meaningful. Small is okay. Small is okay. You know, so I, I, I was fortunate enough to give a TEDX Atlanta talk on this topic a few weeks back. And, you know, the, this, this dream small concept. And after the talk, a woman came up to me and she was telling me that she was in a career of finance and chasing all these goals and stuff. And a couple years ago, she felt like her heart was calling her to save pets, save animals, save dogs from being euthanized. And so she, in her community, she just started doing that. And so she started saving animals. And people around her were telling her, that's not enough. It's not making a big enough impact. And she said, hearing me talk about dreaming small was the first time she felt okay and about what she was doing in pride and what she was doing, and she felt like somebody had seen her. And that example, I, I, I, this twofold one, her, her taking that step, it may, it may only be her local community that she saves, you know, a dozen dogs a year or something, but that's enough. That is enough. The other thing is, is I think about all the work that went into that talk. I mean Ted, Ted talks are, they're no joke. If all that happens is this one woman feels better about what she's doing and continues to do that good work, all that work I did was worth it. Like it doesn't have to get a hundred thousand views. Like it's those small impactful moments that could be enough to drive you forward.
Purposeful and prideful.
[00:07:29] Speaker B: I have to imagine that when you were dreaming big early on that you were following certain type of patterns, certain type of behaviors, certain maybe leadership tactics. How did that change when you pivoted to going from dreaming big to, you know, starting small?
[00:07:48] Speaker A: Yeah, it's a great question. One of the things that is layered into all of this is finding my personal purpose and, and wanting to build and part of that being to build companies that were purpose driven. Companies that stand for something more than just, you know, profit to shareholders, which is important. But if that's the only reason your company exists, it's hard to get people excited about it and feel like their work is important. And so on that journey of working with Dragon army, my third company, to really figure out what's the formula for putting purpose into a business, it was important that I took small steps with that and that we tried little things and I didn't come right out of the gate and hit him over the head with this thing. And we all watched the Simon Sinek video and like that would have been overwhelming and too much and probably would have derailed the business. So in those steps I've learned to be more patient, to take my time.
One of the quotes I like, I'm not sure who said it, but people always overestimate what they can do in the short term and underestimate what they can do in the long term. And so I've become a long term thinker. So my businesses are set up hopefully to be here for decades and when you start expanding that it allows you to think smaller on a daily basis and say, okay, we're going to take our time with this. We don't have to rush, rush, rush, because we don't have to be 5 on the book of list next year. You know, we don't have to compete with the guys around the corner, let's do what we're doing and feel good about it.
[00:09:11] Speaker B: Was this just self actualization? Did you just figure it out on your own or was it some, some counsel that helped you there?
[00:09:17] Speaker A: Yeah, so I went to my sort of main mentor, a guy named Ken Bernhardt when we, when we were selling the second business and he had been along both journeys, the first company, second company supported me always. And I said to him, I was like, Ken, I don't know what's going on, but like we're about to sell this business for a lot and you know, it's by all means a huge success and yet I'm not feeling anything from it. And Ken said, Ken, knowing me for 10 years at that point, said, you need to go through Leadership Atlanta.
And I didn't know what that meant. And to be honest, I thought I had heard about Leadership Atlanta and knew all that, like top leaders went through it. And I thought, yep, that, that feels like another thing that will make me seem impressive. Like it was the same. Gotta be bigger, gotta be, you know, faster. Yep. All right, that, check that box. And so I went into it not realizing why he said that. And there's lots of things you can garner from the year long program at Leadership Atlanta. And so I went on about a two year journey. You know, I read books on purpose. I started to understand, okay, I am searching for purpose. And yeah, I watched, I did watch Simon Sinek's video, I did read his books, I did talk to experts, I talked to a consultant who works with companies and just kept trying to unwind this thing. Ultimately landing on my purpose is to have an outsized positive impact on the world. So I've been given so much and I'm, you know, every room I walk into, I'm taken seriously. I have no disadvantages. You know, I've had hard times, but none of it's because of who I am that I feel like I have to make sure what I'm doing is, is having some sort of bigger ripple effect of positivity. That's why I've started nonprofits. That's why I feel like if I can create businesses that are purpose driven, that I'm slowly but surely trying to make a, a positive impact on the.
[00:10:59] Speaker C: World was enough to get yourself out of that mindset of dreaming big or did. Was that the first step?
[00:11:06] Speaker A: No, it's a great question. So that, that came after because I was like, okay, you know, here I am about, I started my third company, Dragon army, and I want to make a big impact. What can I do? And actually the first idea, and I've not really shared this publicly before, but it's one of my biggest regrets. So I've been passionate about helping our homeless community for a long time. And I had this idea having had companies that had Programmers and building technology that if I could create an organization that could take unhoused people and train them to be developers, and then next to that, they. They. They roll into an internship program that I would create and then a business that I would create. So one of the things that has been tried a lot in, like, prisons is, is to teach people in prison how to code. The problem is, they come out and no one's going to hire them. And so I thought, all right, well, I know how to build a company that, you know, can make money off of programming. So let me put this whole thing together. And I should not have done this. I should have started small. I should have started testing things. But I thought, well, if I'm. I'm doing something, I'm doing it big. I interviewed a lot of people, worked with the homeless organizations in town to identify people. Ultimately got three men that joined my program very quickly. That got down to one man, but he stayed with me for about nine months and during that period started to learn to code. One of the reason we chose him is because he had been getting his life back on track. As we started paying him, he started getting in trouble with the money, and he got into bad habits. He got an apartment he couldn't afford, he got a car he couldn't afford, started using drugs again, and eventually fell out. You know, just stopped coming, and I never saw him again. And I really think I bumped him off track. I really think I did a huge disservice to him because my own ambition was so big. I thought, of course I can do this. And I was dealing with somebody's life. And so that really knocked me over, and I thought, I've got to be smarter about. About these things.
[00:13:03] Speaker B: What lessons did you take from that?
[00:13:05] Speaker A: I realized that if I was going to try to make an impact, the better place to do that would be in my own industry. So I had been building companies that are in marketing and digital, building websites, mobile apps. And so that was something that I thought, okay, I didn't know enough about the landscape of homelessness. I've since been on boards of organizations, so I've learned a lot more. But, like, I was too naive to take that kind of risk and to start small with the next thing I did. And I was really searching for what that could be. And then my team at Dragon army decided to take on a small website for a small nonprofit. But we had to do it very quickly. And the team, you know, griped and moaned, we don't have time for this. And you Know we're already busy, but I was like, I think we can do it. So I, as I say, I volun told them that we'd be doing this project, and we did it. And the interesting thing that happened out of that was that my team, for the first time, started to feel meaning in their work because their work was completely altruistic. It was helping others.
And I felt meaning in my ability to give them that chance. And so because I saw that we did it very quickly, and because I saw that it made an impact to them, to the nonprofit, to me, I thought, I want more of this. So I was fortunate enough to start with a small example. And that made me say, okay, well, there's a lot of people in this town that can build websites. I wonder, if I started inviting teams to an event, could we build a lot of websites in a weekend? And so what was funny was when I would took that big idea, and ultimately I got to, what if we could build 48 websites in a weekend? Even that sounded kind of crazy to me. But again, I had started with one, and I thought, well, if five people built one, my team built one, five other people could build two, and they could be in the same room together. Like, it didn't feel too much scale. But when I talked to the other agency leaders in town, they're like, that's impossible. You can't build one website in a weekend. You definitely can't build 48. But I knew it was possible because I had built the one. So I had seen the smallness of it, and I grabbed one of my best friends and we decided to start inviting people to an event in October of 2015. Hundreds of people showed up. They showed up on a Friday afternoon. By Sunday afternoon, we had built 48 nonprofit websites.
[00:15:15] Speaker B: Okay, so I'm going to push back because that's big, man. That's not small. I mean, you, come on, help me figure this out.
[00:15:22] Speaker A: It's the dreaming. So here. Here's what I would say. Yes, I hear you. But if I had started by saying.
[00:15:26] Speaker C: I'm going to build 48 websites, I'm.
[00:15:28] Speaker A: Going to build 48, I never would have started. That's the part of it. Like, just like the other agency leaders that had teams like mine, they were like, no, it's impossible because I hadn't.
[00:15:36] Speaker C: Thinking about that end goal. Like, that's what, you know, if you only think about the end and how I'm going to get to this big spot, you're like, well, that's impossible to build 48. So I'm just not even going to try to build one. But then if you actually start with that one, you can see what's possible.
[00:15:50] Speaker A: That's right.
[00:15:50] Speaker B: That's right.
[00:15:51] Speaker A: And part of it too, I'll just say, guys, is that the beauty of 48 and 48 is that all these hundreds and hundreds and, and now we've had 7,500 volunteers over the last 10 years go through 48 and 48 events. They make a huge impact and they feel good about themselves. And to me, that's an example of like, that's enough. If that's what they do that, that year, every year, great. Like that, that meaning into their lives, they make an impact.
[00:16:13] Speaker B: Jeff, it feels like you were able to maybe take more risks because you had some security to focus on impact. And, and, and I guess that's hard for maybe a 25, 26 year old who's just trying to figure it out, or a dorm or dorm rat like yourself who was trying to self make yourself. You dreamt big, you hit some financial success and that allowed you to get back to dreaming small and just focus on community impact. But am I being too cynical with that question?
[00:16:40] Speaker A: No, I mean, it's a fair question. I would say it this way. When I get, when I get a chance to speak to entrepreneurs or college classes or whatever, and I get the question, what is your biggest regret? Okay, my answer is I wish I had found my purpose sooner in life. To me, I probably thought exactly that. I've got to work hard for the first X number of years and then I can start doing good. I will tell you this so, you know, 15 years of just head down, grinding away, trying to be bigger and better than everybody. Ten years after that, having purpose in my life, I've had more success in those 10 years than I did in the first 15. And I think it's because of the grounding that I had, the way that I started some of these things.
More patience, it just works. You can outgrind people for a little while, but I think, you know, finding, finding who you are, it doesn't, doesn't mean you need to join a nonprofit at 25, not at all. But if you can make it so that you and your team or whatever you're building has something more meaningful and again, starting small, I think it will make a huge impact. People will be more loyal. Your, your, your company will grow faster than if you're just constantly focused on the financial side of things.
[00:17:54] Speaker B: So Jeff, I think it's incredible that now you've Sort of got evidential proof of starting small leads to something big. With this 48 and 48 journey. You that weekend, how has that carried forward or catapulted you in the last several years?
[00:18:09] Speaker A: 48 and 48. So 10 years in, we just had our 10 year anniversary. We've had 35 events. We've built 1300 nonprofit websites around the world.
7500 volunteers donating 300,000 volunteer hours when Covid hit. So the whole idea is bring hundreds of people together, build websites for a weekend that literally can't exist anymore. That's impossible to exist. The other thing was our biggest sponsor was Delta Airlines. March 16th was the Monday we were all in lockdown in 2020. That was when I firmly and squarely thought, okay, this organization had a good run. The volunteers said, I think we can do this virtually. I had never used Zoom before. So I was like, no, there's no way. And I just sort of immediately thought, there's no way we can do it. But it was the volunteers that were like, let's try one in a weekend and see what happens. And it went great. And then they said, well, let's try four. And it went great. And I still was like, this is going to be near impossible. The important thing there is I still hadn't learned the lesson.
[00:19:07] Speaker C: Yeah, you're still doing the thing.
[00:19:08] Speaker A: I still made the end. I still made the same mistake. But of course it worked out. And here's the most amazing thing about that part of the story. By all practical purposes, we should have shut down. Our biggest constraint up until that point was expanding to other cities. We tried to do LA for like three years. We got to find a venue, hundreds of volunteers, nonprofits. And we at the same time had people all around, not even in America, asking us, can I participate? We're like, can you fly to Atlanta? Can you fly to Boston? Now we have our kickoff in person, usually in Atlanta on Friday at like 6. We have a kickoff at like Friday at 7am for Asia. We have people around the world participating in this thing because we were forced, I would say, to dream small when. When that panic moment hit, forced by our volunteers, who are the people we do this for? And now we're, you know, again, you. We've had this juxtaposition of, like, was it dream big or is it dream small? That moment of dreaming small and trying it. Now we're bigger than ever.
[00:20:04] Speaker B: When people are dreaming big, Jeff, it feels like when they swing and miss, they try again and they keep swinging for home runs, right yeah. If someone's stuck continuously trying, what's one thing that they can do, Jeff, to just sort of reset? I mean, what advice like first step would you give them to get out of this rut?
[00:20:22] Speaker A: I would say the best thing you can do. I'll go back to that startup example, is figure out what your minimum viable product is or your minimum viable dream. In most examples you can boil something down and continue doing that until you get it to a point where you're like, okay, this will test the thesis, but also is something I can do in the next, you know, in the next week, the next month and, and not cause a lot of disruption and see if this is going to work. I'm though, I'm not necessarily saying don't dream big, but I'm saying first you have to dream small. If you can't show them, here's the little steps we're going to take to get here and, and that's the journey we're going to take. You only got three or four big swings in you and then you, then you kind of give up or you're pessimistic or, you know, so I just think, keep boiling it down, keep questioning how small can I get this to understand if this is a path forward.
[00:21:12] Speaker C: What do you think the difference is between dreaming small and not caring enough about having a lofty goal?
[00:21:22] Speaker A: That's interesting. I think dreaming might be the key word to me, dreaming small. When I say that, I really do mean like, you know, what is your dream? What is the thing that you're going to be proud of doing? I have so many friends that are my age, so I'm almost 50, that are like VPs at some big company and they're just completely underwhelmed. They're just like, what am I doing? I, I, I got the corner office, I travel more, I don't see my family. What is it all for? So you can have more money in the bank? You know, I still think people should, I mean, I'm never going to be unwired to say you shouldn't put your best effort forward and you shouldn't try to do your best. Whatever your job is, try to do your best, you know, but when it comes to dreaming and like, what's the thing that's going to make you proud? That's the thing that I think we really need to start and make it manageable. Like, it's weird to say manageable dreams and goals, but it's, you just have to be able to get started. You have to Be able to get that ball rolling downhill.
[00:22:19] Speaker B: Jeff, I think it's great to have you on the show because hearing about how, you know you set big dreams, caused you troubles is good for people to hear because everybody grows up dreaming to be big. But your story actually reflects that. Getting back to just being normal and focusing on small. My backyard, my home, my one to one impact can actually be what catapults people to great big things. So I really appreciate you being our guest today and sharing your story. It's been very valuable.
[00:22:48] Speaker A: Thank you. I appreciate the chance. I appreciate and I love your guys show, so it was an honor to be here.
[00:22:53] Speaker B: Okay, jb, I got to admit, when, when Jeff told us the worst advice he ever got was dream big, I did a double take. I mean, that's usually the stuff that you see on coffee mugs. Right?
[00:23:05] Speaker C: Right. It's like the classic motivational phrase. But what Jeff unpacked really hit me different. It's. It's not that dreaming big is bad. It's that dreaming only big could just steer you so far off course.
[00:23:18] Speaker B: And that mindset, he. He said, really, it didn't lead to success. It led to burnout. Unrealistic, unrealistic goals. And I mean it really, he. He talked about even hurting someone he was actually trying to help.
[00:23:30] Speaker C: He owned it. And you know, it changed how he moves and operates.
[00:23:34] Speaker B: Oh, oh, yeah, it changed him for sure. I mean, it kind of leads to that characteristic that he displayed today that I appreciate the most, which is his humility. Right. He didn't just pivot professionally, he changed the way he thought about impact.
[00:23:47] Speaker A: Yeah.
[00:23:47] Speaker C: He had a quote. It said, dreaming small doesn't mean you stop caring. It means you start in a way that's actually doable.
[00:23:56] Speaker B: Yeah. Which is funny. Look where that led. 48 and 48.
[00:23:59] Speaker C: Right. He ended up in a big place. But by not starting with the huge idea, you know, if you just start with, hey, I want to make 48 websites in a weekend. Someone say, I don't even understand what you're talking about, but do one, do four, do 16. Okay. Wow. You can kind of build yourself up there. And, you know, that's really what the big takeaway is. You don't have to scale the mountain in one big leap. Sometimes the best way is just to make a difference. One small, consistent step at a time.
[00:24:23] Speaker B: Yeah, I couldn't agree more. One website at a time, one episode at a time. That's why we drop them each Friday. Right. Because we want you to listen to these episodes, maybe go back and listen to them a second time. The third time, reflect on what our guests have to say. Because there's so much to unpack in each of these 2025 minute episodes, and today's episode was absolutely no different. We think next week's episode will be impactful as well. So be sure to tune in next week for another episode of the Worst Advice I Ever Got.
