We caught up with the brilliant and insightful Jan Watermann a few weeks ago and have shared our conversation below.

Jan, thanks for joining us, excited to have you contributing your stories and insights. Can you talk to us about a risk you’ve taken – walk us through the story?

One of the biggest risks I ever took happened before I even had a career to risk.

Back in middle school, I realized something most people don’t even question until much later: the traditional path just wasn’t for me. I couldn’t imagine spending my life in a classroom, followed by decades in a 9-to-5 office job. So instead of going on to high school, I made a decision that shocked pretty much everyone around me-I left the traditional education system entirely.

No diploma. No backup plan. Just around $3,000 in savings and a one-way ticket to New Zealand.

I had no clue where I’d live, how I’d earn money, or what the next month would look like. But I had one thing going for me: a relentless curiosity and belief that there had to be another way to live and work.

I started out doing farm work to get by. Then I discovered the world of online business – copywriting, SEO, content marketing. I learned anything I could about it, messaged hundreds of companies, and eventually landed my first remote clients. That was the turning point.

That leap – leaving the safe, well-trodden path without a degree or safety net – set me on a journey that would define my life. Since then, I’ve worked remotely from over 50 countries, built a career as a marketing consultant, and co-founded Pragmatic Business, a boutique consultancy helping other independents and small agencies grow with clarity and focus.

It wasn’t just a $3,000 risk. I put my entire future on the line. And looking back now, I wouldn’t change a thing.

Great, appreciate you sharing that with us. Before we ask you to share more of your insights, can you take a moment to introduce yourself and how you got to where you are today to our readers.

I never finished school. No high school. No degree. Just $3k in savings and a one-way ticket to New Zealand.

From picking fruit to pitching clients online, I taught myself SEO, content, and everything it takes to build a business from scratch-without a résumé or a safety net.

Today, I’m an independent growth consultant and co-founder of Avail Solar – Utah’s fastest-growing solar company – and Pragmatic Business, where we help freelancers scale beyond one-off projects and transform into agency owners with real structure, clarity, and predictable income.

My work is all about building lean, future-proof growth systems – whether that’s through SEO and content strategy, smart positioning, or helping solo operators evolve into business owners. No fluff, no hacks. Just what works in 2025 and beyond – including for AI-powered search platforms like ChatGPT and Perplexity.

What makes me different? I’ve lived every line of what I offer. I’ve built client pipelines from zero, scaled service businesses, and created a lifestyle that lets me live and work from anywhere – all without chasing trends or faking authority.

If you’re done freelancing on hard mode and want to build something that actually scales, we should talk.

How’d you meet your business partner?

I met Robert Roth – who’s now not only a business partner but also a good friend – on a Caribbean island in Panama. We’re both long-term residents of this beautiful (and somewhat underrated) tropical country, and initially connected through mutual friends and a few casual Facebook messages. We figured we should meet up, and that first conversation quickly turned into many more.

What started as a casual meetup turned into the foundation for multiple ventures we’ve built together, including Avail Solar and Pragmatic Business. We realized early on that we shared a similar mindset: practical, entrepreneurial, and always looking to optimize.

One of our favorite ways to collaborate? Over long cigar sessions – brainstorming, challenging each other’s ideas, and figuring out how to build leaner, smarter businesses. Some of our best strategies (and worst jokes) have come out of those sessions.

Looking back, it was one of those rare, natural partnerships that just clicked—and we’ve been building ever since.

Any thoughts, advice, or strategies you can share for fostering brand loyalty?

This is actually one of the first things I teach new clients when they come onboard in our consulting business, because staying in touch is one of the simplest but most overlooked growth levers.

As someone who has worked fully remote for nearly a decade, I’ve learned the importance of being proactive about communication. I make it a point to schedule regular update calls – not just with current clients, but also with people in my broader network. These conversations aren’t just about checking in; they’re where new opportunities, collaborations, and ideas often surface.

Beyond calls, I try to add value in small but consistent ways, whether that’s sharing a relevant insight, sending over a quick audit, or introducing someone to a helpful contact. Staying top of mind isn’t about selling, it’s about being useful.

That’s also what fosters loyalty. When clients know you’re genuinely invested in their success – not just during a project, but long after – it builds real trust. And that’s what keeps them coming back.

Contact Info:

• Website: https://pragmaticbusiness.com/
• Linkedin: https://www.linkedin.com/in/jan-watermann/