Hidden Gems: Meet Ray Stein of Headwaters Digital / Wanderlust Cleaning

Today we’d like to introduce you to Ray Stein.

Hi Ray, so excited to have you with us today. What can you tell us about your story?
After graduating with a degree in business, with a focus on marketing, I got a job at a digital startup as the general manager.

My main focus was operations, but I quickly got involved in the marketing side of the business. Specifically, I focused on digital marketing. About six months after I started, I transitioned into overseeing all of the marketing for the business, as it seemed I had a real knack for it. I quickly realized this was what I was passionate about. I wanted to learn as much as I possibly could about marketing, especially digital.

I decided to look for a job at a marketing agency. I wanted the opportunity to work with a variety of businesses on a wide range of projects. Somehow, I ended up getting offers from three different agencies all at the same time. Two were large and well-established, but one was tiny and still in its nascent stages. I remember being on the phone with the owners and them asking me to walk them through a marketing issue I was currently working on. We actually ended up chatting about it for some time and coming up with a possible solution, as well as the environment in which it could be tested. Based on that call, the decision was easy, I ended up joining that agency, Two Octobers. At the time, they only had one other employee. Over the next seven years, I helped grow the company to over 30 employees. I worked with hundreds of businesses and also did a lot of white-label work for some of the bigger agencies around the country.

As time went on and a lot of the early team members moved on to other jobs, the company started to feel different. I realized I really liked the smaller company vibe, where everything was a little more customized and more personal. That’s when I started thinking about taking some time off and starting something of my own.

I’d spent the last seven years helping build someone else’s business, and I figured it was time to build my own. I talked to my bosses about it, and they were incredibly supportive. One of them suggested I take some time off before jumping into my next thing. I said I was thinking a week or two, and he said, “How about three months?” I ended up taking a full year off because I was having so much fun.

After that, I got down to business. I basically started three companies at once: a cleaning company (Wanderlust Cleaning), an in-home healthcare company, and a small marketing agency (Headwaters Digital) focused on customized solutions for small and midsize businesses.

I’m sure it wasn’t obstacle-free, but would you say the journey has been fairly smooth so far?
Thinking about obstacles and challenges is interesting. My first instinct was to say no, but when I really reflect on it, there have definitely been a lot. Starting any business from scratch is tough. Owning a business during COVID came with a whole new set of challenges.

Honestly, I’d say owning a business is a constant struggle. There is always something new. A problem to solve, a decision to make. But over time, you get used to it. The struggle becomes part of the routine, and it doesn’t carry the same weight it used to. You learn to handle things as they come and just keep moving forward. In fact, I think I would miss the struggles if they suddenly disappeared.

Great, so let’s talk business. Can you tell our readers more about what you do and what you think sets you apart from others?
Headwaters Digital is a small agency based here in Denver, though we work with clients across the United States. Most of the businesses we serve fall in the $2 to $20 million revenue range.

We don’t have any full-time employees. Instead, I collaborate with other small firms and independent experts I’ve met over the years while building and working inside other agencies. That setup gives me the flexibility to bring in the right people for each project, based on what that specific business actually needs.

What that means for our clients is a much more personalized and strategic approach. We’re not just selling a standard list of services or trying to fit every business into the same playbook. We take the time to understand what’s really going on and build a plan around that. I’m proud that we don’t use cookie-cutter solutions or push unnecessary, high-margin services. We focus on helping each client find what actually works for them.

Wanderlust Cleaning is a little more straightforward. I started the business about six years ago. At the time, I owned several Airbnbs and was constantly frustrated by the quality of cleaning services. It was hard to find anyone who would consistently show up and do a great job.

I launched the company with my sister, although she later decided to step away from it. Since then, my mom has taken over most of the day-to-day operations.

We’re still relatively small and not too focused on aggressive growth. Right now, we handle between 100 and 150 cleans per week and have a team of about 10 employees.

Risk taking is a topic that people have widely differing views on – we’d love to hear your thoughts.
Entrepreneurship is a risk in itself. Starting something from scratch, especially when you’re bootstrapping it, comes with a lot of uncertainty. I think I take a fair number of risks, and most of them have paid off. But not all of them have. One business I started and ran for over two years never had a single quarter of positive cash flow. That was a big risk that didn’t work out, but I learned a lot in the process. When I think back on it now, I don’t see it as a failure. I see it as one of the biggest leaps I’ve made in terms of learning how to run a business.

It can definitely be scary at times, but it’s also incredibly rewarding. So yes, I take risks, but I try to avoid unnecessary ones. I try to be calculated. I weigh my options, I think about the downside. But once I make a decision, I move forward and don’t really look back. I learned the hard way that you have to trust yourself. You make the best decision you can with the data you have. If nothing new comes along, then trust your original decision and keep going.

Contact Info:

• Website: https://headwatersdigital.com/