The Living Your Legacy Podcast
Justin Day on The AI Tactics That Will Build A Legacy
Tue, 22 Apr 2025
SUMMARYJustin Day, a three-time bestselling author and founder of Day by Day Digital. As the creator of the Swarm system, Justin is a leading voice in AI-powered marketing, helping businesses scale sustainably using smart automation and data-driven strategies. He shares his journey from learning marketing at his mom’s agency to becoming a CEO, working with hundreds of entrepreneurs around the world.In this episode, Justin dives into his entrepreneurial path, the pivotal moments that shaped his business, and how AI is changing the game for small businesses. He breaks down five key ways to use AI in your workflow, from audience research to content generation, and explains how mindset shifts—like letting go of perfectionism—helped him go from solopreneur to successful founder. He also gets personal, sharing how he bounced back from $100K in debt and why building a lasting legacy drives everything he does.CHAPTERS02:35 – Growing Up in a Marketing Household04:03 – Key Lessons for New Entrepreneurs06:01 – 5 Ways to Use AI in Your Business07:36 – Navigating Challenges During COVID09:14 – Advice for Entrepreneurs in Debt09:50 – Building a Legacy with Purpose10:18 – Tips for Creating a Personal Brand10:41 – What Makes This Episode Different10:58 – Tattoos, Meaning & Mindset11:18 – Where to Find Justin Day OnlineConnect with Justin:Website: https://swarmsystem.aiAI Marketing Tools: https://aimarketingtools.comInstagram: @justindaydigital
Chapter 1: What challenges do solopreneurs face?
The challenges were definitely being a solopreneur and really doing all these things myself. I didn't figure out until three or four years in that, hey, you don't have to do everything. You don't have to be everywhere all at once.
A lot of people are probably in the phase you were three years ago, four years ago. So what lessons would you teach them?
The lessons I would say is... Justin Day is a three-time best-selling author, founder of Day by Day Digital, and a pioneer in AI-powered marketing. As the creator of the Swarm system, he's built a reputation for delivering real results through data-driven, sustainable growth.
Give me five key ways everyone listening should be using AI.
Number one is... It spans the globe like a super high school internet. Elvis Presley. Today, Apple is going to reinvent the phone. It's not over until I win. The Living Your Legacy podcast for those who live to leave a legacy. That's extraordinary. The impossible. Oh, that is sensational. Open. Chicago was the lead. You said Paul is the fastest man on the planet. You can live your dream.
What's up, guys? Welcome back to another episode of Legacy Makers. Sat today with Justin, who's on a mission to make your business more profitable.
He's an AI systems expert, and he basically comes into businesses and shows how to automate a ton of stuff so you can have less staff, less headaches, and be more productive, and has an amazing story doing this for himself, some brands, and now he's helping hundreds of people around the world. So, Justin, welcome. Thanks for having me. So let's talk about, you know, your story to get here, right?
Like, AI is pretty new. You're obviously, you know, really getting into it like everyone is. How did you get there?
Yeah, I mean, I started about 10 years ago at my mom's agency, kind of learning the ropes of marketing and development, learning coding. And kind of along the way, I learned things like leveraging Zapier to connect the DOS to kind of automate things one by one. And then along came ChatGPT, which kind of shifted everything. It really changed it all, right?
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Chapter 2: What key lessons can new entrepreneurs learn?
Yeah, so both of my parents own marketing agencies, so I kind of grew up in that space. So it was, you know, just kind of natural. I was always hearing about it as a kid, listening to the client problems. I knew what I was getting into. It's weird saying you're the first person I've met that has grew up with a parent or agency. Yeah, well, in most people, right, that would turn you away.
You hear all of like this.
crazy well it's pretty new too it's probably only that generation yeah right you know yeah so just growing up in that environment and i always had that creative spark and that you know you got fling that are fanned over the years and that you know burst into starting a you know doing a little bit of graphic design you got friends and then it was like getting paid for that doing some freelance stuff and it kind of organically snowballed and i got word of mouth and grew my business
Yeah. Now, you know, you've grown fast now. You know, you're very successful. But what were some of the challenges getting there?
The challenges were definitely being a solopreneur and really doing all these things myself. I didn't figure out until three or four years in that, hey, you don't have to do everything. You don't have to be everywhere all at once. really outsourcing and leveraging other tools.
And that's really where I came in with your mastermind a few years ago and actually learned how to outsource and be involved in networking and that kind of stuff. So that kind of really shifted my business towards being a solopreneur to actually being a CEO and a business owner.
What were some of the, just for people listening, a lot of people are probably in the phase you were three years ago, four years ago. So what lessons would you teach them?
The lessons I would say is don't feel like you have to do it all right. There's websites out there like Fiverr or Upwork. There's like, you don't have to have a W-2 or like hire a big house team.
Yeah, I think that's a big myth. Like I tell people all the time, go grab someone for a grand a month. You know, it's like I think weirdly, I guess people assume it's like I either do it all myself or I'm going to pay like a hundred grand salary. It's like not that way at all.
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Chapter 3: How can AI be utilized in business?
Number four would definitely be, you know, doing key research for, you know, whether that be competitive or landscape so you can see opportunities to grow. So that's a lot of ways.
And new ideas too, right? New offers, upsells, cross-sells. That comes natural to me, but when I teach that to entrepreneurs, It blows their mind when chat GPT and AI gives them all these crazy ideas. Yeah, definitely. Good.
And a fifth? The fifth one is a new thing that they're doing is being able to actually have conversations with AI. That's the best way. So it's now you can just instead of having to type all because that's kind of been a bottleneck for a lot of people now just have a conversation with it to get the best results. And that's where it's going to be. And that's where it's going to stay, I think.
Good. So let's talk about, you know, your journey to get here. We talked about your parents and stuff, but pretty much every legacy maker has not been a straight line to success. Do you have any challenges or stories along the way?
Absolutely. So, you know, I started my business, like actually filed, actually being an LLC right before COVID. COVID hit. Boom. I was doing about 50 grand a month. All gone. And they were all local businesses, right? Yeah. I was like, okay, well, I don't know what to do here, but I guess I'm just going to keep powering through because I wasn't about this. Not like the job market was there.
So I just kind of sucked it in and I got in about $100,000 of debt. And then I climbed my way right back out of it because I just felt. That was just from living expenses, business expenses. Yeah. I mean, even before, I mean, just doing investments and everything like that, setting up the business and then trying to hold on to that through COVID for six to eight months was Really hard.
But I mean, it all came back to because people had to come back to business and marketing had to happen.
Well, and I always say when people get in debt and money in business, obviously not everyone figures it out. But if you do, it's very crazy. Like some people, you can be in half a million dollars of debt, which to a normal person sounds ridiculous. Right. But you can also earn half a million dollars in profit in one month in a company. Exactly.
And it's like a normal person doesn't understand that because they have a payment cap, right? In a certain amount, in a certain job, in industry. But in entrepreneurship, it can be very scary. But then at the same time, I mean, once you've done some of the winning side too and made the half a million or the 100Ks, you see there's a bit more light at the end of the tunnel to recover from that.
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Chapter 6: How can one build a legacy with purpose?
And through that experience, I was really I saw kind of the vision towards where it's not going anywhere. This is an amazing thing that's going to change businesses. So it's kind of spearhead at the top of it always. And I just saw the future. It's like always being the front of it to build.
Chapter 7: What tips are there for creating a personal brand?
Chapter 8: What mindset shifts are crucial for success?
Love that. And what about your own entrepreneurial journey? What brought you to doing all this?
Yeah, so both of my parents own marketing agencies, so I kind of grew up in that space. So it was, you know, just kind of natural. I was always hearing about it as a kid, listening to the client problems. I knew what I was getting into. It's weird saying you're the first person I've met that has grew up with a parent or agency. Yeah, well, in most people, right, that would turn you away.
You hear all of like this.
crazy well it's pretty new too it's probably only that generation yeah right you know yeah so just growing up in that environment and i always had that creative spark and that you know you got fling that are fanned over the years and that you know burst into starting a you know doing a little bit of graphic design you got friends and then it was like getting paid for that doing some freelance stuff and it kind of organically snowballed and i got word of mouth and grew my business
Yeah. Now, you know, you've grown fast now. You know, you're very successful. But what were some of the challenges getting there?
The challenges were definitely being a solopreneur and really doing all these things myself. I didn't figure out until three or four years in that, hey, you don't have to do everything. You don't have to be everywhere all at once. really outsourcing and leveraging other tools.
And that's really where I came in with your mastermind a few years ago and actually learned how to outsource and be involved in networking and that kind of stuff. So that kind of really shifted my business towards being a solopreneur to actually being a CEO and a business owner.
What were some of the, just for people listening, a lot of people are probably in the phase you were three years ago, four years ago. So what lessons would you teach them?
The lessons I would say is don't feel like you have to do it all right. There's websites out there like Fiverr or Upwork. There's like, you don't have to have a W-2 or like hire a big house team.
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