A year ago, Myles couldn’t build a website. He was a senior cybersecurity professional at one of the Big Four consulting firms in the US, the kind of company whose name you’d recognise instantly. He was well paid and good at his job, and he was on the leadership track. He was also wearing what he calls the golden handcuffs: long hours, weeks spent away from his young daughter, and very little time left over for the life he actually wanted.
Twelve months later, Myles has left that role to run his own website and AI SEO agency in Charlotte, North Carolina. He’s netting between US5,000 and US10,000 a month, has retainers lined up, and is in conversations with corporate clients that most new agency owners never get near. One deal he closed even came with free private school tuition for his daughter. He was also one of our High Achiever Award winners this year. Watch our full conversation below to hear Myles tell the story in his own words.
I’ve coached Myles closely through this journey, so I want to break down exactly what he did. This isn’t a story about luck. It’s about a clear plan, a lot of discipline, and one very simple idea: the more conversations you have, the more money you make. If you’re sitting in a well-paid job and seriously considering quitting corporate for a career change to digital, this is the blueprint I’d want you to study.
The Real Cost of the Golden Handcuffs
Myles doesn’t badmouth his old career. He loved the work, learned a lot, and says many of those skills transferred directly into his business. But anyone climbing the corporate ladder eventually runs into the same trade-off.
“As you go up a certain path, the one thing you’re gonna give up is time, and time, I think for any entrepreneur, is the most important commodity you have.”
His wife is from France and works full time as a senior brand manager. Their daughter is two and a half. Myles was spending weeks at a time away from her, and he knew the lifestyle they wanted wasn’t going to appear while he stayed on that path.
His conclusion was blunt. To get the life they wanted, he’d have to “somewhat divorce the paycheck” and take a couple of steps back financially in order to take much larger leaps forward.
Plenty of people in corporate feel exactly this way. Most of them never act on it. So what made Myles different?
Why Myles Actually Did Something About It
Before corporate, Myles served in the military, and he’d always known he wanted to work for himself. He’d tried a few things over the years and nothing stuck. What he needed was a model that was scalable and affordable to start, and that fitted the lifestyle he and his wife were after.
When he discovered online businesses, and specifically what we teach at the eBusiness Institute, something clicked. “That flipped a switch of like, okay, that’s very doable,” he told me.
He liked that an online business runs with lean overheads, can be built from home, and mostly requires time, software and repetition rather than a big capital outlay. In his words, “you can start building online businesses with not a lot of money with the right attitude.”
That combination matters. A strong reason to leave, plus a realistic vehicle to get there, is what turns a vague daydream into a plan. Myles already had the drive. He just needed a business model that made sense.
The Plan Was Three Years. He Did It in Twelve Months.
I want to be really clear about something, because I get asked it constantly. We don’t recommend you quit your job straight away. And Myles didn’t.
When he joined our community, he and I mapped out a two to three-year transition plan, which is what we do with most of our members. He was highly paid and in a job he enjoyed, so there was no reason to rush.
He started in our Digital Investors program, learning the practical skills of building websites, SEO and AI SEO, then moved into our Champions coaching community around September. From there, things moved much faster than either of us expected. By the following June and July, he was booking a coaching call with me to talk about leaving early. We’ll get to why in a moment.
If you’re reading this and thinking, “I’d love to build a digital income stream alongside my job, but I don’t know where to start,” this is exactly the path Myles took. Our Digital Investors Program teaches you how to build, grow and profit from websites and online businesses, step by step, with the coaching and community to keep you accountable.
How to Find Time for a Career Change to Digital While Working Full Time
This is the question everyone asks, and it’s one we’ve seen answered before by members like Jason and Sally, who built online businesses while working corporate jobs and raising three young kids. Myles was in a demanding senior cybersecurity role, he had a toddler, and his wife worked full time. So how on earth did he fit it in?
The honest answer is sacrifice, and he doesn’t sugar-coat it. Before anything else, he sat down with his wife and got on the same page. There were areas she had to pick up because he couldn’t. “She saw my vision, she believed in me. So from a partnership perspective, I had that support, which was critical.”
The 9-to-5, Then the 8-to-1
His days were highly systematic. He’d do his corporate job, look after their daughter, put her to bed, and then start his second shift.
People talk about the “9 to 5, then the 5 to 9.” For Myles it was more like 8pm to midnight or 1am, followed by a 5am start the next morning. He kept that up for a year.
He’s the first to admit it was unbalanced. But he also sees it as a rite of passage: “You’re putting in the hard yards and cutting your teeth on doing long hours. It’s a rite of passage, in my opinion, that callouses you for what entrepreneurship requires.”
Audit Every Input
Time is finite, so Myles went looking for leaks. He audited everything going into his head. Social media that wasted his time? Gone. The books he read had to be intentional.
Every portion of his day was examined with one question in mind: if I really want to build this, how do I optimise this hour?
He also leaned heavily on the weekly intention-setting sessions we run in Champions, regularly revisiting his one-year and five-year goals. Because, as he says, motivation disappears quickly when things get hard. “That’s where you have to lean on discipline.” And when discipline wavered, he went back to his why. “When I put my daughter down, that’s my why.”
Design Your Environment
Myles had one big advantage: he worked from home, so there was no commute eating two or three hours of his day. He didn’t waste that gift.
He set up two desks in his office, one for corporate work and one for agency work, so he could switch contexts instantly. “For those that are working from home and you have that flexibility, that’s a gift, so use it.”
Free Websites First: Getting the Reps In
Despite his technical background, Myles had to learn website building from scratch, just like everyone else. That took him a solid six months of evenings and early mornings.
And his first builds were slow. Really slow. “My first websites would take me months to make. Months.” His own personal website was rebuilt five times as his skills improved.
His advice for anyone starting out is to build a few sites for yourself or for friends with small businesses. It’s low stakes, and every one teaches you something.
The Hot Dog Truck That Exploded
One of those early freebies was for his childhood best friend back in Minnesota, who runs a Scandinavian-style hot dog business called Nordic Dogs. I loved this site and we’ve featured it at our summits.
Myles spent ages on it, and it paid off for his mate in a big way. The business is now booming, he’s looking to add more trucks and open a bricks-and-mortar store, and “a lot of it is just traffic that’s coming to his website.”
That’s the hidden value of free work done well. It gives you a portfolio piece with a real result behind it.
The Ultramarathon That Led to His Biggest Client
This is one of my favourite stories from any of our members. Myles was training for ultramarathons and volunteered at a race in his community. Before he went, he checked out the race company’s website, saw it needed help, and took notes.
On the day, he approached the race director: “Hey, I’m learning to do XYZ. I’d love to help you out.” They had a coffee, and Myles rebuilt the site for free.
It performed well, and in return he got free entry into some races. During one of them, a 50-mile race in the North Carolina mountains, he found himself hiking alongside another runner who asked what he did for a living. Myles started to say “cybersecurity,” then caught himself. “Well, actually, I do website development.”
That small mindset shift changed everything. The runner owned a wedding venue in the Smoky Mountains and needed help with his website. That project became a $10,000 build and Myles’ biggest retainer at the time.
It was the catalyst for him leaving his job. Volunteer, do good work, show up, and own your new identity. That chain of events is worth studying.
The Earliest Networking Group in Town
Myles’ other secret weapon was beautifully practical. He looked for the earliest BNI meeting in his area, one that ran from 7am to about 9:15am. He’d race home afterwards, sometimes cutting it fine, and start his corporate day.
Interestingly, he didn’t join BNI until seven or eight months into his journey, once he’d built the skills and had work to show. Even then, standing up in front of a room of entrepreneurs and saying “this is what I do” was terrifying. “Deal with that imposter syndrome. It still was really scary at first.”
It worked quickly for him. Within a couple of months, referrals started flowing, and because he did good work, those referrals multiplied. He’s realistic that it can take longer in other chapters, depending on the people and the market. But his principle is universal: curate those relationships early.
BNI also taught him something he’d never needed in a remote, behind-the-keyboard cyber career, namely how to actually network. How to hand over a card, what to talk about over coffee, how to follow up and nurture a relationship.
Raising Your Prices as Your Confidence Grows
Myles’ pricing journey is a great reality check for anyone starting out. He went from free, to $500, to $1,500, and now a baseline of $3,500 to $4,000 (all US dollars). Some of the projects he’s delivered include:
- A travel agent website: $5,500
- A financial consultant website: $3,500
- A local church website: $3,500
- The Smoky Mountains wedding venue: $10,000
Each price rise felt uncomfortable, and he’s honest about that. But once you understand the value you’re delivering, he says, those prices really aren’t unreasonable.
His net revenue over the last few months has ranged from $5,000 to $10,000 a month, and once current projects launch, he expects ongoing retainers to add roughly $4,000 a month on top. A smart rule worth copying: he doesn’t start retainer work until the site has launched.
Keep in mind, he spent the first six months learning. These numbers came in the following six months, while he was still working full time, without any significant financial investment. It’s a similar pattern to Kim and Nick, who turned their learning year into a $75K earning year.
From Small Businesses to Six-Figure Corporate Conversations
This is where the story gets really exciting. Myles is now in conversations with much larger corporate clients, deals we believe are worth six figures. One is a joint venture project with a world bank.
So how does someone go from building $3,500 sites for BNI members to sitting across from C-suite executives? His answer: transferring credibility.
When people call each other and ask, “How’s your guy going?” and the answer is “He’s doing great work,” doors open. Some of his work has come from several hops of introductions, one person connecting him to another, who connects him to someone else. “You just never know who’s in whose phone book.”
He’s since joined a second Charlotte group, a mastermind-style huddle of entrepreneurs, which has widened his network further.
His corporate background also helps. When he tells people he came from cybersecurity and now builds websites and does AI SEO and AI implementation, it signals trust. But as he’s quick to point out, the background opens the door; you still have to earn the credibility once you’re inside.
Sales 101 for Bigger Rooms
Just as he studied digital skills, Myles has studied sales seriously. He keeps sales books on his desk and leans on mentors in his community, as well as our coach Calum, who comes from a corporate background.
Large organisations, he’s found, have the same fundamental needs as small businesses. They’re just bigger. “They’re all humans, they have certain agendas, and it’s understanding what they wanna avoid, what they wanna accomplish, what their fears are.”
In practice, that means mapping the buying influences in the room: who controls the budget, who’s the user buyer, who’s the technical buyer, and who influences whom. He also looks for a “coach” inside the organisation, someone who can be a sounding board and explain the personalities at play.
At its core, though, the question is simple: “For every dollar I give you, do I get five in return?”
Know When to Walk Away
Not every deal lands. Myles walked away from a large project with a California construction company when a new buying influence entered the picture that would have made it more headache than it was worth.
He treated it as a lesson and debriefed afterwards, which is something he now does after every significant conversation. What did I learn? Where did I miss opportunities? What will I do differently next time?
Never Stop Filling the Pipeline
Corporate deals come with long sales cycles. Budgets shift, quarterly numbers change, decisions drag. Myles fills that gap with smaller, faster projects.
His biggest warning for new agency owners is to keep prospecting even when you’re busy. “What can happen with an entrepreneur early is you get all this work and you do all this work, and you stop prospecting, and you have nothing.”
After he went full time, he was actually networking so much he couldn’t deliver, so he set himself a rule: one coffee and one virtual meeting a week until things became manageable.
The Crossover Point: When Quitting Corporate Made Sense
Around June and July, two things happened at once. His corporate role was demanding more leadership responsibility, and his networking was suddenly working. Real clients were paying him real money, and Myles takes that responsibility seriously. “I don’t have the luxury of dropping this ball.”
Both sides started to suffer. Something had to give. Around then, he’d watched my Digital Investors Podcast interview with Henry, another Champion and former engineer who’d also left his job earlier than planned, and he booked a coaching call with me.
We worked through it carefully, because he has a young family. But the decision wasn’t made on a whim. He and his wife had been setting up their finances for this moment for one to two years before he even joined our community. “When the day did come, I was prepared and comfortable enough to make that jump.”
“Matt, this is my chance. I’m young, I can afford to take a risk.”
Myles
He told me that, and I’ve thought about it since. Calculated, planned, and backed by real revenue. That’s how you quit well.
Myles’ Advice for Anyone Considering a Career Change to Digital
I asked Myles what he’d tell someone who’s outgrown their corporate job. His answer was practical. Start by auditing what really matters to you and what direction you’d push your life if you could.
Then look at the skills and circumstances you already have. He worked from home and had technical skills, so websites and AI were a natural fit. Yours might be different.
Accept that there’ll be sacrifice. And then ask yourself the hard question: what’s the worst that could happen? “It doesn’t work and I have to go back. Okay. Then I’ll do that and at least I tried.” Because, as he reminds us, “a year is gonna happen if you want it or not.”
Finally, break it down. Every week, Myles writes down five simple things that will move him closer to his goal. On Friday, he reviews what got done, what didn’t, and what distracted him. Then he resets for the next week. One bite of the elephant at a time.
The Takeaway: It Wasn’t a Solo Effort
For all his discipline, Myles is clear that he didn’t do this alone. “Seek out the people that have accomplished the things that you wanna accomplish and get around them.”
His wife’s support, his coaches, his mentors and our Champions community all played a part. He just happens to run the agency solo, with a little help from a team of AI agents. That’s a story for part two.
Here’s what I want you to take from this. Myles started with no website skills, a demanding job and a toddler at home. He followed a plan, did free work to get his reps in, put himself in rooms full of business owners, and kept having conversations.
Twelve months later, he’d brought forward a three-year goal and built a business with genuinely exciting upside. It wasn’t about the income. It was about getting his time back and following a lifelong dream.
If you’re in a job that’s paying well but costing you the things that matter, maybe this is your sign. Start where Myles started. Join the Digital Investors Program and learn the skills to build your own digital income, on your own timeline, with people who’ve done it beside you.
