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Member Spotlight: Braving the Hard Yards in Your Entrepreneurial Journey with Dylan Roos

While owning your own business is no small feat, Dylan Roos knew it was what he wanted to do from his first week at his first job. “I got through my first week, and I was like... I can’t work for someone else. I just inherently knew... but it’s funny if I had known then what I know now about running a business, I’m not sure that I would have still wanted to do it then.” Despite the task being daunting for his younger self, the now owner of Roos Health & Performance takes the trials and tribulations of owning his own business as a masculinity coach in stride.

Since that first week of working at a marketing firm, Dylan went on to study health coaching and neuro-linguistic programming, helped create the Roos Men’s Wellness & Leadership Club with his father, co-founded the MoMENtum Lifestyle Project, and was a speaker at several events before 2020 hit – and suddenly, Covid jolted the world to a stop. This meant no more events, no more speaking engagements, and a lot of time to think about his next move.

Over the next 6 months, he pivoted solely to coaching, buckled down, and worked on developing his new program before launching and selling out his first Prince to King Mentorship Program. Dylan now acts as a masculinity coach full-time, with his Prince to King Program helping more young men every year.

Q: Tell me a little more about what the Prince to King Program is about. A: Essentially, we mentor young men anywhere from 14-23, but we work with boys as young as 12 up to 30-31. Our purpose is to teach emotional mastery, healthy habits, leadership, and purpose to develop young men into positive role models with a lifelong desire for self-improvement. We're also starting to develop more support for parents as well, so it's continuing to grow.

Q: How did you decide, out of all the things you could do, that you wanted to coach young men specifically?

A: Three reasons – 1) there was a massive gap; no one was speaking to young men, and we kind of see the result of that in Andrew Tate and the red pill movement. No one was speaking to young men, and he was born because there was a market for that. 2) My own personal challenges, probably needing mentors during that time as well, and 3) I wanted to be a coach, but who would listen to me at 26 years old? Probably not corporate, probably not guys older than me; I didn't have enough life experience. So it was more of a tactical decision as well, that these are the people who are actually going to want to listen to me and take on my advice because I'd just come out of that. Help who you used to be, basically.

Q: I know you've mentioned that owning your own business is hard and takes a long time to see success. At the same time, I feel a lot of passion behind your Prince to King program – would you say that's what keeps you going and slogging through the hard times?

A: I mean, yeah, by the time you realize how hard it is, you're already in it, so you just keep going. If I were going to pivot now, I've already done the hard yards for the past 3 years, and I'm about to start reaping the rewards, so I'm going to keep going, knowing that it's still going to be really hard, but I'd also rather not do anything else.

Q: When talking about your company, you often mention it being born out of your own personal challenges with feeling lost, and you're also very open and realistic about owning a business being a challenge in and of itself. Would you say that you still feel lost or now that you've done the hard yards, do you think you've found your footing?

A: "When I was younger, I was lost in the sense of I didn't know where I wanted to go or what I wanted to do. Now it's more like I'm doing this thing – am I doing it right? Do I know what I'm doing?" So, a different kind of lost, or I guess I would say unsure more. There's a lot of stuff online where people have got to this stage where they are really successful and they talk about this massive belief that they had, but it's the massive belief coupled with crippling insecurity; you have both. I think to run your business you have to have the belief you'll succeed one day, but the whole journey you're questioning it.

Q: Over the years, you've grown your following fairly significantly. Do you have any advice for people looking to expand their reach on social media? '

A: Find your niche. The narrower you go, the better, and you can also charge more because you're narrowing down. If I'm teaching a mindset course, maybe I can charge a few hundred dollars because that's really general and doesn't speak to any one person. But if I teach a life coaching course to young men between 14-23 that's going to help develop their mindset, then I can charge a few thousand because I'm speaking to one person, and that person will hear that and think, "Oh my god, he's talking to me; he knows so much about me, and if he knows so much about me, that means he can help me."

Q: It seems that throughout your own personal journey, business, currently, you're good at reframing your mindset, stepping back, and being able to see the forest for the trees. How do you do that in your business? There's so much to juggle as a business owner, and it's easy to sometimes get wrapped up in the small anxieties, so how do you prioritize or find the path that works best for you?

A: There is a very simple answer and a very complex answer to this. The simple one is your business needs to be making money. Why are you in business if you're not making money? So you can do the website, you can do the brand, all the fancy things surrounding it, but at the end of the day, if you're not making money, what are you doing? So focus on making money. I say that because I've made that mistake before, where we focused all of our time on different sections until we felt like they were perfect, and then the business had to shut down because we weren't making money.

I'll go through periods where I don't do anything else but focus on sales, but there are also times where I go, 'okay, there are a lot of things I need to fix in my business now.' Have I made some money? Yes. How much time can I afford to spend away from sales? 2-4 weeks? Okay, great, now I'm spending 2-4 weeks fixing a bunch of stuff in my business, and then I'll re-enter the sales.

I think a lot of people get caught up in all the information online, all the gurus, all the people; at the end of the day, you need to be making money. And you don't even know if the marketplace wants what you have. When I first launched my business, I didn't have a product; I had the idea of a product and I put together the bare minimum of what it was going to look like, but it wasn't created yet. I set a date, launched, set a goal for clients, got those and realized, 'cool, people want what I'm selling.' So all I had to do was for week 1 have week 1 done, week 2 have week 2 done. I didn't have a product until I started to do it. That's another challenge that a lot of business owners fall into. They create the perfect product that no one wants or they spend all this time creating something, and then when they launch it, they realize 'oh, they want something slightly different.' My product now, even, is so much different than what it was when I launched, and I've done a lot of different things because you're experimenting with what works and what the market wants.

In the ever-evolving world of entrepreneurship, Dylan Roos's journey from a determined young man with a vision to a thriving masculinity coach has been nothing short of inspiring. Through his Prince to King Mentorship Program, he is not only filling a crucial gap in mentorship for young men but also demonstrating the power of unwavering passion and adaptability in the face of challenges. As he continues to empower and shape the lives of the next generation, Dylan's story serves as a testament to the importance of finding one's niche, embracing change, and, above all, never giving up on the path to success.

To explore more about Dylan's transformative work and the invaluable insights he offers, visit his website at or connect with him on Instagram @dylan.roos

Dylan Roos

Founder of Dylan Roos Coaching

Treehouse Kahala

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