We recently connected with Kristopher Bolleter and have shared our conversation below.

Kristopher, thanks for joining us, excited to have you contributing your stories and insights. Innovation comes in all shapes, sizes and across all industries, so we’d love to hear about something you’ve done that you feel was particularly innovative.

I’m a bit of a process-nerd, part OCD, part fascination with optimization and how we can continually improve in every aspect of our lives. It’s this obsession that drove me to create my own SaaS platform for my freelance processes and communicating with clients and stakeholders, Roadmap Tracker (roadmaptracker.com).

The system may not be all that “innovative” on the nose, if you’re familiar with the most famous tracking platform, the Dominos Pizza Tracker. But it seems to be a foreign concept to virtually any other industry or persons who need to track their own processes, whether for goals, projects, or delivering a pizza (well maybe not). The point being it seems like a revolutionary innovation for my processes, so I built it.

As a freelance Brand Strategist and User Experience Designer by day, I had many of the tools and competencies needed to build the system, just no backend Development experience, So I’ve partnered with a team of awesome backend developers to make Roadmap Tracker a reality and testing it with a small group of users currently – about to roll it out to the public.

As always, we appreciate you sharing your insights and we’ve got a few more questions for you, but before we get to all of that can you take a minute to introduce yourself and give our readers some of your back background and context?

I’m a multidisciplined freelance Brand Strategist and User Experience Designer (and front-end developer) from Georgetown, TX (Though we all claim Austin at this point, right?). I’ve had the opportunity to collaborate with organizations in a diverse set of verticals, of all sizes from small businesses to Fortune 500 companies. Though most people get introduced / referred to me as a “website developer” or “logo designer” these days, I love how that’s just the tip of the iceberg. Working with clients to expand their understanding of what makes a brand strategy successful and where to dedicate our efforts to make the biggest impact is something that’s made me tick since the early days of the web.

I got my start online like many in my generation did with Myspace and the internet boom. I was enamored with building something from nothing, and styling it limited only by your digital creativity, while rewarding how “clever” you could be with putting the puzzle together – if there’s one thing you learn as a front-end developer, it’s that there is no “right or wrong” in many agnostic styling circumstances, and it rewards thinking out of the box.

Flash forward to anything professional, and I feel like I was all too fortunate to have almost fallen into the opportunity, in part due to my passion for it, my drive, and overall mission to be a positive force in everything I do (which I also refer to as the “Three P’s” in another Vantage interview)

Can you talk to us about how your funded your business?

There are really two major “Funding” inflection points for my business, the first was when I made the jump to go fulltime freelance. I was an in-house Creative Director for a small product design and marketing agency in Georgetown, Spindle 360, while freelancing nightly for relationships I had built in my previous position. At a certain point, I realized the income from both streams were getting competitive. I took that opportunity to request more compensation, not getting the exact response I expected, I took that opportunity to jump ship into the freelance world. “Why spend 8-9 hours a day working straight to make what I was making in 2-3 hours every night” I thought. Best decision I ever made. Working for yourself unlocked the “unlimited linear correlation between input and output” I knew I could thrive in. Now it’s been roughly 6 years of fulltime freelancing through a pandemic, numerous networking opportunities, and through it all I’ve been fortunate to keep growing year over year.

Due to this growth, I had some money set aside I was planning to parlay into “traditional investments” (stocks and all that fun stuff) but I saw an opportunity (and no reason not to) continue betting on myself. I took that investment (along with my skills) and funded Roadmap Tracker. It’s been a true labor of love that started November 2022, and I couldn’t be more excited about the traction and early feedback I’ve gotten, before even going public.

We’d love to hear the story of how you turned a side-hustle into a something much bigger.

Expanding on the story from the source of the funding, working nightly as a freelance designer and developer while working fulltime was instrumental to my success. I get asked how to get started in freelancing often, and it’s really no secret, you have to do the work. What I mean by that is put yourself in a position to do the work. When I left my position as the Lead Graphic Designer at Harris Media to become a Creative Director for Spindle 360, I didn’t want to let those connections I made go to waste. Even though the to organizations were in completely different verticals, I used that opportunity to foster more relationships and opportunites to collaborate during my “free time” – granted, I tell everyone I’m blessed and all too fortunate to truly call my work my hobby. Cliche as F___ but I swear I haven’t “worked” a day in my life since I quit working at the GAP as I finished college.

After I left Spindle 360 to pursue my freelance opportunity fulltime it seemingly gave me exponentially more time to focus on my own work, what was previously 2-4 hours available every night before crashing grew into 12-16 hours… a blessing and a curse if I’m being honest. The “linear correlation” between your input and output is truly only limited by one variable… time. Now that I had so much more, I’ll admit it was definitely a shock at first to find the pace, rhythm and quantify how much I needed to fill my schedule. Being your own boss is such a responsibility to hold yourself accountable, while not beating yourself down and burning yourself out. A key milestone for me was the birth of my son, that responsibility and accountability light switch went from “freelance money is cool” to “freelance money is necessary” and that, combined with my OCD for process optimization quickly led to a full pipeline.

Contact Info:

• Website: KristopherRay.com
• Instagram: https://www.instagram.com/kristopherray/
• Facebook: https://www.facebook.com/kristopherraycreative/
• Linkedin: https://www.linkedin.com/in/kristopherray/