From $32K in Debt to Dr. AI: How Jonathan Built a Digital Company of One

Hello, hello, hello. Welcome back to The Human Side of AI, and I'm your host Flora. Before we dive in, I have to be transparent with you like I usually am. You're going to hear me say, okay, I'm going to push record at the start of this episode, um, but I wasn't ready to let go of the first part because I want you to meet Jackie first and just wait until you hear that. So keep an eye out. Um, but more importantly, today's guest is Jonathan, also known as Dr. AI, and he earned that name the best way possible. Um, a stranger on livestream gave it to him while he was showing up and serving with zero product, zero service, and $32,000 in debt. That's the kind of person we have on today. Jonathan is a Southern California native who taught himself to code out of necessity, built a robot from scratch with $5,000 in parts from China just to survive his soul-crushing job, and eventually took everything he learned in Salesforce consulting and high-performance venture capital environments to go all in on AI education. Today, he runs a community of over 250 entrepreneurs, coaches them through a 5-stage curriculum, and has developed 4 core systems he believes can help any business owner double their revenue in just 90 days. Oh, and he does most of it with a team of 3 AI agents. Let's jump into it.

Hello Flora, how's it going?

Great, how are you?

Very well, pleasure to meet you.

Nice to meet you. And I'm honestly just gonna push record here in a minute and just start asking all the questions. But before I do that, who's Jackie? Jackie AI note-taker.

My Fathom meeting AI note-taker, same like yours.

Have you named her Jackie?

Yeah, I named my personal assistant Jackie. She's, you'll hear me like, Jackie, do this, Jackie, do that. And they're like, hey, who's Jackie? She's in the system. I'm like, I don't know, it's a bunch of cloud conversations and they're doing all my work.

That's so funny. I knew— I mean, I knew there was a reason. I know it wasn't like you were on your like wife's account or something, you know what I mean?

So this guy's already got an assistant. Listen, let's dive deeper. This guy's interesting.

No, I love that. I will say it's the first time I've ever heard of anyone renaming their, um, note-taker, and it makes perfect sense.

It's such a— we're living now in the world of the movie Her. It's now here.

Yeah, for real. And you're really, you know, you know. So I'm just going to push record and we're just going to start asking.

Start cooking.

Cool. I feel like they move my record button every time. I know.

It's always the last. They're like, hey, zoom.

There we go. All right, Dr. AI, where are you calling from?

Pleasure to meet you, Flora. I'm calling from Southern California.

Oh, beautiful. What part?

Pretty much Claremont. Beautiful Claremont, away from the downtown LA traffic.

All right, cool. And how long have you been out there?

All my life. Also Cal. It's kind of hard to move away when you kind of like been baking under oven. Can't do cold, can't do anywhere else. I'm kind of spoiled.

I feel you. I live in the jungle in Panama and we have two seasons. And I just like, I have a very hard time understanding how people can like walk in snow intentionally.

Snow days or like, or I'm like, nah, I can't. Even there's a slight breeze, I'm like, I'm too cold. No, no, no.

I know, sometimes I'm like, oh, I have to turn my air off, it's too cold. Okay, sorry for like half the world listening to this. Um, okay, so Jonathan from South Carolina, uh, California, so down there, Laura. Talk to us, like, how, what was it like being a kid there? And then how, I mean, talk to us a little bit about how you became Dr. AI.

Quite the interesting journey in the sense that, blessed enough that God's put me on a journey only in hindsight that I was able to connect the dots to see I'm exactly where I'm supposed to be. Needless to say that put me on a journey of becoming Salesforce certified, working in San San Francisco working with elite teams and high-performance, um, venture capital. Um, oh, it's very competitive up there, but from that I learned the skills that I take today with my community. And I see a gap in the market of, uh, pretty much just computer education, which stems into AI education. And did a marketing agency after I left Salesforce. I did marketing agency for 2 years, tried to get into AI, but it just wasn't the time right. So It wasn't until January 25th that, or January of 2025, that I had to make a very big decision. What I was, yeah, what I was doing was just not working. Sometimes, yeah, you're on a path and it's like every time you put effort in, it says not getting any traction. Sometimes the universe telling you that it's like, hey, you're in the wrong environment.

And at this point you were in the agency world?

I ran a marketing agency for 2 years, did all marketing sales or marketing and sales. Sales automation tech stacks, but it was burying a hole in me. I was $32,000 in debt, 2 months behind in rent, January 2025. And I was like, I got to change. There's something different that's got to go. So went all in on AI, all in on short-form content, had to do something completely different, drop everything and started AI with a prayer. Said, hey God, send me the people you want me to serve because I tried it. Tried AI, I was like, nah, this is not, I don't know, I don't want to, let's— and he's like, look, try it. And I was like, all right, if you want me to do this, send me the people, send me people you want me to serve and I'll serve them to the utmost capability. And since then it's been a rocket ride. I've been blessed to meet over, gosh, anywhere from 500 entrepreneurs that all have an ambition to use AI to make an impact in the world, honestly. And I'm here to empower them.

Yeah, no, I love this. Okay, so let's, let's bring it back. So you said, so did you actually work with Salesforce or did you, uh, like the company, or did you work Salesforce for other companies?

Started off as a Salesforce consultant, uh, even before that quit my 9-to-5 job, no backup plan, no, no option B. And then God, fate put an article saying, hey, Salesforce career can make the same what I was making at my corporate job. And I was like, Okay, I did Salesforce there and I actually automated everything on my old job. So I was like, let me see what's this, what's up with this? And got certified, started my own consultancy, and then landed opportunity in San Francisco for some very big startups. And there really honed my skills.

Wow. So I want to even take it back a little bit more than that. So before you, you know, joined corporate America, like, did you have— were you a young tech kid? Like, what, what was that like for you as a kid? Like, how did you know that you you were going to start this, you know, this career in technology?

Always had a very knack for, uh, computers and knowledge. Always on the computer building, pushing the boundaries of what's possible. And it was through necessity that, uh, my corporate job that I had to adapt to learn or teach myself how to code, how to honestly do robotics. So because just to automate the whole job, because I was like, this is a soul-sucking job, I gotta— there's gotta be a better, a better way. So forced myself to get into coding and forced myself to get into robotics, automated my entire 9-to-5 job. And then from there, I got really good in Salesforce automation. And then that's— by that time, I was corporate burnout and I was like, I gotta like, peace out. This is not for me health-wise. And then Salesforce came opportunity, got certified, started the consultancy, and then San Francisco was a wild ride. Yeah.

So you just said something really cool. You just said basically like my job was just crushing me and I out of necessity had to learn how to code to basically automate my role there. I mean, that wasn't— so someone didn't come to you and say, hey, you need to automate all of these tasks. You were like, I need to figure out a better way to do this.

To a degree where it went to levels on the software level. That was the first job where there's so much amount of work that has to be done and everything's manual and no one wants to automate anything. The whole organization is a public organization. And so meritocracy, doing things innovatively are very counterintuitive. And so for me, I was like, I just have a knack for taking things apart and proving them just for my own engineering mind. And from there, taught myself honestly AutoHotkey, which was a Windows automation software. Software that within a weekend taught myself that language. And then from there went on to automate everything in my 9-to-5 on a computer, got around IT, and then pretty much— and then I'd walk into work with a USB stick with maybe 10 megabytes of files that had about 30 programs that did my job, my team's job. And I'm like, I'm walking in with half a million dollars in labor and a USB stick. And I'm like, this is changing everything. And that fear opportunity to also open up. So I was like, I got to teach. So I started teaching at makerspaces and then I got pushed to more difficult projects at work where I needed to even teach myself robotics because one of my jobs, they wouldn't invest $100K in a robot that would do that job. And I'm like, wait, you're paying me and what you could do, your ROI is pretty easy. Like you'll make your money back. And they're like, no, no, no, just sit here and do the work of 4 people. And I'm like, this is not humanly possible. This is like, okay, fine. So I learned went online, Google, uh, found Google Patents, found the defense contractor that made the machine, uh, gave myself a budget of $5,000 and 2 months and bought parts from China, taught myself how to do robotics, 3D printing, rapid manufacturing, and then built a robot that then automated that piece there. And then by that time I was already too burnt out.

But yeah, you, you just said something, you said It was fear or opportunity. And I feel like that could be its own, like, podcast series, right? And I just, I wanted to bring people's attention back to that statement because what a beautiful, like, what a beautiful chance to question, right? Like, are you feeling fear and is this an opportunity ahead of you? So I, I love that and I love that You know, so many times I talk to people and they're like, I went to school for this, like, this is what I did. And then, you know, it's like people hearing it could think, okay, well, I didn't go to school for this, so that can't be my outcome, right? And it's like, that's not what you're telling. You're telling us, I just had to figure it out. I had to learn it. I taught myself a language on a weekend and I mean, anyone can do that, right? And so that, that's really cool. Thanks for sharing that. So you mentioned you're empowering— you, you, at this point in your journey, you've, um, you're empowered— you've empowered over 500 business owners. And I love that statement. Talk to us a little bit about like what your day-to-day looks like. Like, do you have a morning routine? Like, what does it look like to be who you are?

Discipline. Um, I am an ADHD entrepreneur, and from that, I have to— everything that I do business and routine, everything, even for my curriculum and the stuff that I teach, all bases through ADHD management without medication. And so I've developed my own framework from that that has a very systematic routine of schedule and tools that allow me to replace what I would say is my executive functions, my, um, my long-term memory, so that I can ruthlessly execute on the amount of obligations that I have to do throughout the day. So I leverage tools like TickTick to manage my time and ask. And then with it, I have a routine where, believe it or not, I wouldn't be here where I am if it wasn't for content. So my first non-negotiable is content, is making sure I'm posting 10 times a day. Get that out of the way. Second, because I don't have a sales team, I don't have— I'm not running ads. Everything, the whole business is funded through organic growth. Second to that is mostly working with my agents. I have a team of about 3 admin agents. I mentioned Jackie, who's my personal assistant, one. Those help me manage all of the inboxes, inboxes for clients, inboxes for community. We have about 250 entrepreneurs that are all going through a 5-stage curriculum to go from complete beginner to making a few money with AI. And so it's responding to the questions that they're bottlenecked, looking at the curriculum holistically to make sure I'm trying to aim for an 80 to 90% success rate this year. And then Lastly is working one-on-one clients and coaching and helping to implement systems in their business. We identified 4 core systems that could help any business owner double their revenue in 90 days.

Also, I'm sorry, when you say we, that's you and your 3 agents?

Yeah, yeah, it's, uh, I have a thesis of, uh, you're now— we now have the capability to build a digital company of one. Um, and so what is that process? What is that framework? And from there, um, you could have many different agents that are part of your business that are working on different aspects that now, and it's, that's the scary part is like that's replacing the workforce and that is now. And so it's really just staying on top of, so, and then lastly is health, health and wellness, exercising, gym, meditation, and then also just eating, good sleep, and just taking care of over health. It's like trying to find a balance at the end of the day is what everyone's North Star.

Well, I want to, I want to talk to you a little bit about that because, you know, you, you are our king of automations, right? So, I mean, in theory, that gives you a lot of your time back to be able to, you know, take care of yourself and that health and wellness space. Does it truly, or are you just spending more time automating other things?

That's a very difficult challenge question, I would have to say. So I would say 2 weeks ago I didn't understand the word balance. Now, over the next couple of weeks, I'm now forcing balance into my schedule. But it's really— that's a very difficult paradox. What that means is that when you get into AI, one of the things that they don't tell you is that you're going to spend less hours sleeping. You're going to spend more hours building because today is an opportunity where you can literally turn your ideas into dream, into reality very effortlessly. From that, people are working harder, working longer. Are they making more? Are they being more busy or productive? I would say they are being more busy with multiple projects. That's the hardest thing is to focus on one thing to make the true impact on what you want to do. But yeah, from there it's, it's possible. I would say it's a great opportunity now that these tools now empower you to reach your goals faster in an easier amount of time. And so people are working longer hours, late nights. I'm seeing it on the weekends. I'm seeing it in my cohorts. People are spending more time after to really build their future to— honestly, what's what everyone wants. They want to escape the 9-to-5. They want a digital product so that they don't have to work. They can work on their own schedule. And everyone right now prioritizes a remote lifestyle. So everyone right now is trying to figure out what's that product, what's that transition from 9-to-5 to entrepreneurship. And I've made that journey and I could tell, I know, especially with all of my students, I know how scary that transition can be.

Yeah. So, so you said, you know, this shift has kind of happened for you personally in the last 2 weeks, this finding balance. If you don't mind telling us, like, what was that? What was that? Okay, I really need to start prioritizing balance here. What, what did that for you?

I'm very blessed. I have a family that, um, I have a brother that is very, very, um, ambitious and very, very, um, someone to aspire to look up to. He's very pioneering, I would say, health and wellness, uh, his journey, um, and then sharing that with the whole family. So for me, I feel blessed that I get to shortcut, I would say, the health and wellness kind of like game in the sense of learning from him, seeing, um, what do's and don'ts, and then also the impact that you can have in the sense that putting yourself in a position and a state to accept more abundance, uh, to manage the gifts and the blessings that you asked for, which is always going to be more responsibility, more time, more this. But at the same time, it's what you asked for. And so now it's, it's taking care of health and wellness so that you can play this game for a longer period of time instead of a short season.

Yeah. And how do you see this, this balance evolving for you? And while you sip your water and, and, and answer that, I just wanna come back to the statement of accepting more abundance and just really hoping that resonates with whoever's listening, you know? So, but yeah, tell me a little bit about, you know, what, how do you feel like this, this will, you know, evolve for you?

I'm a man of ruthless action. Um, so last night I was up till about 2:00 AM for about 3 hours and rebuilt everything, rebuilt my entire business model, rebuilt my entire offer stack, rebuilt my entire website and rebuild my entire onboarding process. Over the last couple of weeks, it was getting very clear on the goal that I'm trying to reach and the people I want to take to that top of the mountain. It requires discipline and also sacrifice to say no to a lot of other opportunities to focus on this journey. And then from that, that is going to allow me to work with more qualified individuals that really want to leverage automation to make the impact in their business. It's also going to allow me to go deeper into my current members, into their current business, and really help them reach their goals a lot faster.

And then as far as your health and wellness, like that, that journey, how, you know, you said you started that 2 weeks ago. How do you see that developing for you?

Yeah, so the— it's going to be religious, uh, two parts. One, strength training. Second, proper nutrition, uh, which includes, uh, very more getting back to people with ADHD have a very, um, regimented supplement nutrition supplements they have to like take in order to just, uh, function. Getting back into those. And then also, believe it or not, connection, uh, connection in social groups, picking up hobbies again, getting back to salsa dancing. Yes. Changing that routine up. How fun!

Well, I'm excited for you. I mean, and I, and I'm, I have no, no doubt that your business is going to continue to evolve. And I'm just really excited for you in this personal journey to, to really expand on your health and wellness too, because at the end of the day, like, AI in theory allows us time to be more human, right? And that's, that's what it's about. So, um, okay, you're teaching people— actually, before this call, I had a chance to listen to the replay, um, that you did for our, our Club Jam members, and I'm obviously going to link that here in in the show notes. Um, and you know, you're— that it was so much fun to listen to, and, and I, I look forward to going back and doing it with you like you suggested. Um, so you're teaching people to clone themselves so they can show up without burning out, and you know, what do you do to prevent burnout for yourself?

That is a very good question. Um, honestly, right now I'm in this very specific season. I would say, um, a lot of people want to find balance, uh, and Well, on one side, yes, balance is key as far as taking care of health and also rounding out the area domains of your life. For me, I find more being in business. This is a very specific season in business. You're— when you get traction is a very small window of time that you have to go all in. You'll look back at it, entrepreneurs, and be like, damn, that was such a moment in time. If I only had double the amount of output, got stayed an extra because getting a business off ground to traction to me is a time of no balance. I just feel like entrepreneurs in the stage of where this is that you shouldn't seek balance. You have to seek traction and get the business stable. You have to get the business where you're not the product. I would say only until that stage is met, then you can seek balance, then you can seek, but you have to build the system systems and routines so the business generates revenue outside of your involvement. And a lot of entrepreneurs I find want a laptop lifestyle, want to work less, but also have a part-time, like, job or part-time income that replaces their six-figure career. And I'm like, that doesn't exist. You have to sacrifice an ungodly amount of time and effort, um, in order to reach— when it— to play at this level I'm experiencing. And so I see more of I'm not playing hard enough and I need to go harder. Um, and so That way, that way for me, I'm looking more— although balance is a big thing, I'm just really ruthlessly doubling down on automation and output so that I can honestly crush competitors and be the only one.

Let's see if we can do it for you. Yeah, yeah, fair. And but you've been burnt out before, so what are you going to do to, to make sure that doesn't happen again?

So with it now, now blessed with agents, we now have the capability to season, hone, and deploy agents to automate work. That was the part that was the biggest bottleneck is before, like with ChatGPT and even before Claude, we didn't have any agents to actually delegate and actually do work where we're not tied to a computer.

Yeah.

So that's where I see now it's like the skill set now is to build agents or have a member in your team who's certified to build agents or automations because then you'll be able to set up the systems that would give you the time to have the balance that everyone seeks.

No, I appreciate that. So what's something that you still do yourself on purpose that you could automate but you won't?

Roadmaps with clients. Every client, when they come to me, I give them a very clear roadmap, 90-day roadmap, but help them generate revenue, automate their business and so forth. So with it, it's really— although there's so much that I could do for automation, it really comes down to there's something you can't automate, which is taking the time to really holistically basically look at the person's goals, their business, their state of where they are, and put together a very clear roadmap that meets them where they are, um, and then also gives them the resources to help them reach their goals, kind of like, uh, in a sense of like quicker. So for me, it's a lot of like, um, yeah, just assessment resources so that I can help them close the gap on where they are to where they want to be and make that transition smooth and fast.

Cool. What a quick answer too. I love it. All right, cool. So do your closest people, your family and friends, do they see a difference in you since you went in all in it in AI? Like, what is their experience watching your journey from their perspective?

It's only within the last year. So the first year was just a grind. First year was just establishing. First year was like, ooh, we got some followers for sure. A lot of people are like, oh, this is a, oh, he is just doing the AI thing. Kind of. So it's not until you, I guess, reach a certain followers or, um, or after the first year, that's when things become more, more stable in a sense. So that's when friends or family are like, oh, this is a thing. Oh, this is a business. Oh, it's actually impacting many there. Oh, and it's not just you. So then, so that's to me is, um, well, yeah, it's, um, Friends and family, entrepreneurship's a very lonely game. So I have only maybe one family member that's in entrepreneurship, and so they're very early in their season. And so I would say friends and family may not understand the journey that you're on in business. So you want to surround yourself with groups of entrepreneurs and business owners so they can speak your language, know your struggles. And then I would say they're the family, especially in the business world, that's going to celebrate your wins, help you on your losses and then also relate to be able to be, to say, I've been there and this is how I got stuck. So not to say to not focus on family, but it's really two separate families, one for health and wellness and life, close family, and then you'll have your entrepreneurship and business family, and both are equally as valuable.

Yeah. So if someone's listening to this and they're like, man, his fire, his, his His, his spirit is like something I'm feeling really connected to. Who is your ICP and how do people know that they need to work with you?

If you're an entrepreneur that's generating over $200,000 a year, you're already established and you're the bottleneck. You already have a team, or you are—

hold on, you said you're already established and you're the bottleneck? That's powerful. Okay, I just wanted to bring attention to that. Continue, please.

Because I have a lot of entrepreneurs, they're solopreneurs, coaches, consultants, maybe, maybe have an assistant or maybe two people. Functionally, they are the product, they are the business. Uh, the business doesn't generate revenue without activity or involvement from them. Um, and for me, it's, uh, being able to help them automate their entire business so that they can reach more people, serve a greater, our greater audience, and then helping them buy back their time so that they can spend almost half the amount of time while making the greater impact. So for me, it's coaches, consultants, service providers that are the bottleneck in their business that know AI automation is the path and opportunity and want a clear path to leveraging agents and automations to truly scale their impact, reduce their overhead, and make the impact that they want it.

No, I love that. I love that. So, so I talked to, I've had the chance to talk to several different agency owners and, and, and founders of companies and they, they help automate businesses as well, right? What do you think you do differently than others?

Beautiful. With my Salesforce experience, I've identified 4 systems that every business needs that could save them up to $2,000 a month in overhead. We live in a time where now everyone is selling big SaaS. Everyone sold everyone a GoHighLevel subscription, but at the end of the day, people are stuck with tools that aren't helping their business move forward. So with that, my ideal clients are looking for proven systems, one, to automate their marketing, sales, website, CRM, email automation, digital products, payment collecting, all of that in one app. We sell that so that they could cut the cord from GoHighLevel and other agencies, own their data, built-in true automations, and leverage agents to manage the front end. I'm the only one who's truly automated full content automation with digital avatars at the highest quality. So I already know. So from that, business owners come to me when they want to get to posting 10, 20, 30 times a day using avatars and automation. That's going to be the second package that they'll need to upscale into. Next, teams that have 3 or more, you're using ClickUp, monday.com, or spreadsheets to manage your operations on the back end. And these tools are your bottleneck. They're preventing you from truly automating your team. So let's get them off. That was our third system operations. And lastly, my, my fun one is actually their own course platform. So traditionally they're using Skool or Circle and they're paying hundreds of dollars a month for a platform that requires them to manually log in and upload some information and copy paste and prevent their members from actually completing the courses because we all know they're not taking the courses. So with that, I built my own custom learning management system that I sell to companies so that they can build their own internal AI course platform. And so these are the 4 systems that are the foundation that every business will eventually adopt, that they'll now have the foundation to truly automate and build the digital company of one.

Wow, wow, wow, wow. Okay, and then what is— if some— if you're talking to someone and this is really clicking with them, what is one thing you want them to do right after they listen to this?

Watch my YouTube.

Is there a particular one?

Nah, there's tons there. You'll find something there of value that will make the impact on your life. Second, I have a very clear, uh, roadmap. And the first step is, honestly, if you have— I know, so very, uh, strict— but if you have a Mac computer, I have a free Mac training that will double the amount of time and save you 24 hours every single week. It's a free course that I offer. That's the first step in my training program. And I find that we have about a 95% success rate of members that go through that and eventually ascend into all of our other programs to truly leverage automation. So I would I would say come take our Mac course, it's completely free. And from there, with the time that you'll save, reinvest it back into your education.

I love it. I love it. I love it. And I know you've answered this question before, but just tell us, how did you become Dr. AI?

I was on a livestream and I had no product, had no service. I was livestreaming, $32,000 in debt, 2 months behind, and just showing up and serving, just showing up and answering questions. And from that, over the last, the next couple months or the next 30 days when I did that I found that every question that people answered, I would always have some answer that will help them get clarity and move the next step. So one person on the livestream, God bless her soul, they said, you're like a doctor. You're like a doctor AI that people could come to and you can answer, you have the answer for everything. And from there I was like, let's just have fun with this. Let's just see. And from there it's been honestly a blessing that I get to call myself. And, but it's really the impact that I get to make is the members and their lives that they, or the impact that I'm having with them allows them to reach a greater audience and make a bigger impact. So to me, that's the biggest gift is the skills that I teach others allow them to make this world a better place.

I love that. Well, thank you so much for taking the time to chat with me today. I know you're very busy and you could have probably automated 6 workflows in this time. You know, but at the end of the day, like I truly believe and so do a lot of our members, but, you know, using AI allows you time to be more human, right? So thank you so much for sharing your story, and I look forward to following it as it unfolds, and you're doing great things out there, and just thanks again for your time today.

Honestly, thank you so much, Flora, not only for the opportunity to be interviewed, but also Robyn and the whole Jam Club. What you guys are doing there is truly making an impact, and the community that all of you have built is truly something special that I'm grateful just to be a guest stuff.

Well, we look forward to hearing more from you. Take care, talk soon.

Bye.