EPISODE OVERVIEW

Duration: Approximately 25 minutes

Best For: Trapped entrepreneurs who built successful trades or service businesses and now feel chained to every decision, every email, every project

Key Outcome: A clear framework for taking a "refining year" that lets you step back, reclaim your health, and still grow revenue without adding headcount

He had a 4 year old son. He was skipping lunch, logging on at midnight, and feeling guilty every time he went surfing.

THE BOTTOM LINE

Justin Dickinson built Cousins Co Renovations from nothing to a multi-million dollar operation in six years. On paper, he was winning. In reality, he was drowning. The thing is, his story probably sounds familiar. You started this business for freedom. You wanted to help people, build something meaningful, maybe even have time for the things that matter. Then somewhere along the way, the business became your prison. Justin hit that wall about a year ago. Anxiety creeping in. Drinking too much. Skipping the gym. Missing moments with his son that he knew he would never get back. So he did something counterintuitive. He stopped chasing growth and took what he calls a "refining year." The result? His business runs smoother. His team is happier. He is present for bedtime. And he is on track to scale from 3 to 5 million with the same team of six, using AI to eliminate the work that was slowly killing him.

WHY THIS EPISODE MATTERS TO YOU

You will discover why pausing growth to refine your systems actually accelerates your freedom, and what happens when you keep pushing without stopping

You will learn the exact mindset shift that allowed Justin to stop feeling guilty about taking time for surfing, skiing, and his son, because that guilt is costing you more than you realise

You will understand how a small trades business is using AI to handle transcriptions, estimates, and material lists, freeing up hours every week without adding complexity

You will hear the hidden cost of being the bottleneck, and why your team, your family, and your health are paying the price right now

KEY INSIGHTS YOU CAN IMPLEMENT TODAY

The Refining Year Strategy: Justin hit 1.5 to 2 million and instead of pushing harder, he paused. He spent a full year putting processes in place and stepping back to see the whole picture. The consequence? The next two years became "more friendly to the owners, to our project managers, to all management." If you keep sprinting without refining, you will burn out before you ever reach freedom.

Self Care Is Business Strategy: Justin noticed something powerful. When he would sneak out for a surf or a ski day, he would feel guilty on the drive there. On the drive back, every problem that seemed impossible suddenly had an obvious answer. "All of a sudden I have all those answers because I took the time to give myself a break." Your best business thinking happens when you step away. That is not a luxury. That is a competitive advantage.

The Loneliness Solution: As a trapped entrepreneur, you cannot talk to your staff about the hard things. You have told your wife about the business so many times her eyes glaze over. Your friends are tired of hearing it. Justin started building a community of other small business owners in Maine, people who actually understand. He also started talking to AI in a therapeutic sense, using it to reframe his thinking. You do not have to carry this alone.

AI For Trades Without The Overwhelm: Justin is not using AI to replace his team. He is using it to transcribe walkthroughs and phone calls so he can be fully present with clients instead of scribbling notes. He is exploring tools that take drawings and generate full material lists. He is automating scope of work tracking to catch change orders automatically. The goal is simple. Go from 3 to 5 million with the same 5 or 6 people.

The 70/30 Work Split: Justin realised the part he loves, the walkthroughs, meeting clients, seeing a new home for the first time, that is the human work AI can never replace. The repetitive stuff that drains him, the estimates, the material lists, the admin, that is where AI belongs. Figure out your 70/30 split and protect the work that lights you up.

GOLDEN QUOTES WORTH REMEMBERING

"On that drive back after I gave myself that self love, that self care, all those questions I had on the way there were like, oh, that's so simple. Why was I even contemplating this?" - Justin Dickinson

"I needed to make a change for my health. For a few months I couldn't quite get there. I'd get stuck back at the computer, I would skip lunch, and I have a 4 year old son. I'm not going to get this time back." - Justin Dickinson

"We hit 1.5 to 2 million and said, let's take a second and refine for a year. Let's not just keep going, driving ourselves crazy, getting over our head." - Justin Dickinson

"The more you learn, the less you know. Always learning, always improving, always humble on what you do know." - Justin Dickinson

"If I reach my goal, great. If I don't and go a completely different way, even better. That just allows me to not dwell on things as much and enjoy the present, because that's really all we got." - Justin Dickinson

QUICK NAVIGATION FOR BUSY LEADERS

00:00 - Introduction: Why surfing helps trapped entrepreneurs think clearly

02:15 - The Moment of Unemployability: When Justin realised he could never go back to a job

04:30 - Birthing a Business: The brutal first years and why it feels like raising a baby

06:45 - The Refining Year: Why Justin paused at 2 million instead of pushing to 3

09:20 - Health Wake Up Call: Anxiety, drinking, skipping the gym, and missing moments with his son

12:00 - The Self Care Discovery: What Justin learned on the drive back from surfing

14:30 - The 70% Guilt Problem: Why business owners feel guilty about everything and how to break free

16:45 - Loneliness as an Entrepreneur: Building a community when nobody understands

18:30 - AI for Trades: Transcriptions, material lists, and estimates without adding staff

21:00 - The 5 Million Vision: Scaling revenue without scaling headcount

23:15 - Tangible Pride: Driving around town showing his son the kitchens they built

25:00 - Conclusion: Next steps and where to connect with Justin

GUEST SPOTLIGHT

Name: Justin Dickinson

Bio: Justin is a problem solver, entrepreneur, and co-founder of Cousins Co Renovations in Portland, Maine. Over six years, he and his cousin built a high-end renovation company approaching 3 million in revenue. Justin specialises in helping clients transform their homes while navigating the challenge every trapped entrepreneur faces, how to grow without losing yourself in the process.

Connect with Justin:

Website: cousinscomaine.com

Instagram: https://www.instagram.com/cousins.co.maine/

Facebook: https://www.facebook.com/cousinscomaine/

YOUR NEXT ACTIONS

This Week: Identify three tasks you do every day that drain your energy. Write them down. These are your first candidates for AI automation or delegation. Notice what happens to your thinking when you imagine not doing them.

This Month: Schedule one "refining day" where you step completely away from operations. Go surfing, skiing, walking, whatever clears your head. On the drive back, record voice notes about the solutions that appear. Your best ideas are waiting on the other side of guilt.

This Quarter: Map out your own refining year. What processes need documenting? What decisions could others make? What would your business look like if you only did the work you love, the client walkthroughs, the creative parts, the human connection? Build toward that vision.

EPISODE RESOURCES

No additional resources for this episode.

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READY TO ESCAPE THE TRAP?

Take the Freedom Score Quiz: https://scoreapp.atpbos.com/

Discover how trapped you are in your business and get your personalised roadmap to freedom in under 5 minutes.

Book a Free Strategy Session: https://www.atpbos.com/contact

Let's discuss how to build a business that works WITHOUT you.

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CONNECT WITH YOUR HOST, ROY CASTLEMAN

Roy is the founder of All The Power Limited and creator of Elevate360, a business coaching system for entrepreneurs ready to scale without burnout. As a certified Wim Hof Method Instructor and the UK's first certified BOS UP coach, Roy combines AI automation, wellness practices, and business operating systems to help trapped entrepreneurs reclaim their freedom.

Website: www.atpbos.com

LinkedIn: https://www.linkedin.com/in/roycastleman/

YouTube: https://www.youtube.com/@allthepowerltd

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Good morning, good afternoon, good evening, wherever you are in

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the world. I'm here with Justin Dixon and we're going

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to talk about business and we're going to talk about

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life and we're going to talk about AI. Welcome to

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the podcast. I appreciate it, Roy. Thanks for having me.

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I said what was fun before and you said surfing.

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One day I'm going to get it. I just went

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to Morocco to start learning it. Yeah, I've been in

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the other places. I've been jumping out of airplanes and

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going underwater and never quite got to surfing. But yeah,

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what a fun experience that was. How long Mako Mako,

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I have heard, has some fun surf. I haven't gotten

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down there. Portugal is a fun one as well, but

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there's actually a growing community here in Maine. I'm a

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general contractor in Maine and. And there's a good little

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community here that are pretty badass. They're wearing hoods, gloves,

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booties in the summer. Geek on. Booties on. It's a

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good way to clear your mind as well. It's a

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good way to get into flow state and forget about

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everything else for a little bit. People look at what

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I do in the adrenaline side of it. I jump

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out of airplanes and they're like, oh, you're just an

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adrenaline junkie. And I'm like, no, it's not. It gives

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me a time when I can be in the moment

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and then I can't think about it. Brain finally stops.

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So tell us about business. What I actually want to

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know about is when did you step out of being

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employable and become unemployable? What was that moment like? Pinpointing

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that. Probably about a year ago. Roughly a year ago,

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I really stepped out. We've been in business for six

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years. We do a lot of high end renovations in

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the Portland, Maine area. Me and my cousin starting up.

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I managed everything and he's the finished carpenter. We're both

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on site making it happen. We were gonna do some

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of our own investments. This is all during COVID when

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there wasn't a lot of properties available. So we just

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used other people's money and got us off the ground.

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So. And here we are still renovating for other people

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six years later, but unemployable. I just had to do

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a salary sheet for a new accounting company that's helping

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us out. And it's a long list, a lot of

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hats to wear and every week's different. So I'd say

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probably a year to two years ago is when it

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was really clear that Myself and my cousin, the other

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owner were unemployable. That's the thing, right? You start this

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thing and it's your baby, right? And you birth this

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baby and for the first six months it's like a

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bloody baby. You can't sleep at night and you're up

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until 3 in the morning. Yeah. Every waking moment is

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all about this thing that you birth and. And then

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it goes to the terrible twos and it's like, ah.

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Then slowly but surely you get to the teenage years.

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I think business owners are so cool because they see

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a problem in the world and they I want to

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fix that problem in the world. How many people do

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you know that have said to you, I've got this

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great business idea, yeah, people actually do something about it.

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That's the hardest part. It doesn't have to be perfect,

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you just gotta go for it. I think it's funny

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though, there's always that next step, right? They say it

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into a million's tough and then two to three million

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is the hardest part. We'll do about two and a

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half to three this year we kind of hit one

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and a half, two and said, let's take a second

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and refine for a year. Let's not just keep going,

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driving ourselves crazy, getting over our head. Let's refine for

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a year, put processes in place, take a step back

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and look at the holistic picture. And then these past

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two years have been more friendly to the owners, to

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our project managers, to all management and just been smoother.

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I would recommend a refining year or two. What you

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mentioned there, it comes to the heart of what I

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try and do, this journey of business ownership.

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You start it because you want to be free, right?

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And very quickly it becomes the biggest prison. There's no

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time off, you never switch off, always on, right? And

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quite quickly. I think one of the things that happens

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is you end up putting your own health second long

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hours, you don't go to the gym anymore, you don't

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do the workout, your stress level goes up, you're always

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living in stress. How have you felt that this break

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year or break period has helped you manage that? I

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can relate to that 100%. About a year ago I

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noticed I needed to make a change for my health,

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anxiety wise. Drinking too much, not going to the

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gym, not surfing enough for a few months I couldn't

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quite get there. I'd get stuck back at the computer,

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I would skip lunch and I have a 4 year

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old son and it's hey, I need to be present

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for him, this is not. I'm not going to get

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this time back. I'm the people pleaser as well. That

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person can wait. Or a quick email to say, hey,

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it's going to be next week. For the past six

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months or so, I've really dedicated time to the gym

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time with my son. I'm logging off at the end

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of the day. Honestly, I would feel bad if I

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went skiing and I wouldn't tell my team and I'd

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be like, hey, I'm going to sneak out and go

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skiing for the day because there's a big storm or

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surfing because there's a big storm and feel really bad

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about it. But on that drive back after I gave

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myself that self love, that self care, all those questions

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I had on the way there were like, oh, that's

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so simple. Why was I even contemplating this? Oh, all

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of a sudden I have all those answers because I

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took the time to give myself a break, to give

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myself a little freedom or whatever it is. And all

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of a sudden email seemed easier to write. That self

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care is actually beneficial to the rest of the team,

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to your wife, to your partner. Yeah. I think that

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brings up the other big thing I hear all the

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time. 70% of business owners are guilty all the time.

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Guilty about taking time off, guilty about not doing work

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with people, guilty about not sending the email back to

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the client, guilty about asking the staff members to do

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stuff. It's like, hang on. Without us being there, doing

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the thing, starting the business, the these people wouldn't be

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feeding their families. Right. 1% of people in their lifetime

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will start a business. 1%. Really? That's the number? That's

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the number. And I think that's built into that 1%

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though, is setting high expectations and never really reaching them

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and just continuing. Who's a good example? I don't want

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to use Elon Musk. I'm going to anyway. He's. I

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know I'm not going to get it done in six

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months, but if I set it for a year, then

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it's going to take two years. If I set it

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for six months, I actually get it done in a

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year. So it's never good enough. It's just always being

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creative, always looking for the next thing. And really enjoyed

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talking about AI with you before this call. What's that

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next thing? Because once you get stuck or static

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like then somebody else is going to come and make

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it work. I think there's this big piece, right? Yeah.

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We look towards what everyone else is successful, right? Yeah.

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And we're like, okay, they're all doing this and there's

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way more people not doing it then those people that

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are doing it that we compare ourselves to. Right. I

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needed to hear that. Yeah. I've been focusing on being

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easier on myself, not looking into the past and the

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future so much. Here's a goal. If I reach it,

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great. If I don't and go a completely different way,

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even better. That just allows me to not dwell on

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things as much and enjoy the present, because that's really

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all we got. And then the other thing, before we

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start talking about AI because that's so cool, what's your

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view on loneliness as a business owner? Loneliness?

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I have this thing that I've learned over the years.

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Right. We have all these people around us, we have

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staff, we have family, and we have friends. But because

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you're that 1%, they don't know. When you've told your

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wife five times about your business, the eyes glaze over.

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Right. And then you're becoming boring. You can't talk to

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your staff about it because especially those things that are

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painful. Yeah. Your friends are like, okay, there he goes

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again. Something you're excited about. I think about that a

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lot too, Roy. I think like, I eat lunch alone

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a lot, running around to projects, whatnot. Loneliness in that

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sense. But I also, because I've stepped out more and

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delegated and hired the right people, it's almost setting myself

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up to be more lonely in that direct sense. But

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as far as just in the mind, I think it's

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really helped to create a community that is Business owners.

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Maine has a lot of small businesses. So I do

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have some good friends that also run small businesses that

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I can talk to. And then I've been talking to

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AI almost in that therapeutic sense. It'll

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help me reframe my thinking and is something to

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talk to AI. Right. I know. I've seen that

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the world is so scared of AI and the

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opportunity that's there is we can do 10 times more

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work with 10 times less people. And this is the

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problem because it's like, I've now got a staff of

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10. How do I justify getting rid of 10 people?

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And I'm trying to get people to reframe this. Right?

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Yeah. We have the opportunity to have people do the

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work that they love doing, which should be the human

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part, which should be the visual part, which should be

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the connecting with other people, having more conversations with customers,

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having longer time to talk internally. If we can do

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10 times more work in six hours a day, that's

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the vision I've got for it. AI can never have

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that connection, that relatability, that face to face. My favorite

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part of my job is doing the walkthroughs, seeing a

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new home for the first time, taking some measurements and

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getting to know these people. I had one this morning

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with friends I know from our daycare and it was

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almost like a friend meetup. That's the part I enjoy

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the most. So how can I get all this other

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shit that gets repetitive off my

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plate? For us, it's very personal. I'm coming in and

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I'm renovating your kitchen. Potentially you're going to be living

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upstairs while we're downstairs working and we're going to be

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selecting everything together or working with a designer. But it's

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very personal and I don't see AI taking it over

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anytime soon. So to all the people out there, the

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trades is a good place to be. Yeah. What's that

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feeling you get for you when you hand over that

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kitchen? Yeah, it's special. It's not always as glorified

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as the TV shows make it. We hand it over

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and there's usually a punch list of little things that

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need to get done. Yes, it's special. And I can

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drive around my neighborhood or around town with my son

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and point at the houses that we've renovated. It's very

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tangible and goes from the very beginning, creative aspect,

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designing it to a tangible kitchen that you're going to

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use for the next, potentially lifetime, 50 years, hopefully longer.

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It's very special. I think the other thing I wanted

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to note was just, I think we do this because

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this is the problem we see in the world and

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we go out and fix it. I love working with

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business owners, having a conversation with them and I see

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the light go on in their eyes and they're like,

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ah, that's the shortcut I can do to get to

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the next stage. That's what I've been missing. It is

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about the connection. What we start with as business owners

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is a vision that we chase after. Right. I want

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to see 10,000 business owners live the life they love.

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I love going and traveling. I love working around the

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world. I work with all sorts of different people. Right.

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That's what lights me up and that's what gives me

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enough power to carry on through the difficult stages. Right.

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How many difficult times have you had? How many times

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have you not taken a salary because you got something

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wrong or something went against you or Covid hit or

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something? A couple times have not paid ourselves for a

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Few months. I think there's always something

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to improve on. It doesn't stop, it doesn't end. It's

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always the next mountain to climb. In construction in general,

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there's always something to learn. I think a lot of

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the skills are getting lost with the retirees that are

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leaving. And we're a young team, we're all still

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in our 30s or younger and trying to get people

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excited about it. I think you might have an influx

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of people coming to work for you, right? Just saying.

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Yeah, but yeah, where are we going? Where do you

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think? Yeah, where are you going to be in the

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years? What is good look like for you in five

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years time? So right

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now we're reaching towards 3 million from the financial side.

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I think if we can utilize AI on the back

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end and on the design and take drawings and do

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a full material list from it, that's a lot of

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time. If we can speed up estimates, speed up the

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whole planning process and also start transcribing every conversation,

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not only the zooms, but walkthroughs, phone calls, transcribe all

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that, get it to pull from our scope of work

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and say, hey, this, this is a change order. And

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because back to your point, I'm trying to connect with

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you so I'm not taking notes of everything. I need

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that transcription if we can, because right now I don't

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want to grow our team. I have a goal of

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staying at 5, 6 people, 5 and a half part

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time and can go from 3 to 5 million with

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the same team. That's the goal right now. That's going

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to be the power of AR, right? Yeah. You can

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go from 3 to 10 million. Yeah. If all those

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things can be sped up for you, you can do

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that. And there's. How many things in the day do

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you not like doing? If you can find those 10

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things you don't like doing and make them 10 times

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faster, that's going to be the power. It's fun the

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first couple times because you're figuring it out and then

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once you do it 10 times it's like, ah. And

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you still get to do that with AI almost more.

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You get to create that whole process, agentic systems, if

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you will bring that in. And then all of a

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sudden you're not doing it day to day. You're not

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doing the mundane. That's the curse of the entrepreneur especially.

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You'll sit at the visionary parts. You get much more

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excited about figuring stuff out and much less excited about

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operations 100% and

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learning that process as you go through it. That's the

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fun part. Always learning, always improving, always humble

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on what you do know. The more you learn, the

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less you know, right? Thank you very much for joining

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me. It's been awesome chatting. And if I ever get

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to Maine, I'll come surfing with you. And likewise, show

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me how to actually do it properly. We'll catch up

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in a year's time and see if you made your

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5 million. All right, sounds good. I appreciate it. I'll

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put all your contact details below and we can catch

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up and see where it goes. Cousins Co renovations cousinscomain.com

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or cousinsco main on Instagram. Cool. Thanks for coming. Thanks,

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Roy.