For our latest interview of the BOSSES series, we sat down with friend and entrepreneur, Andrew Follett.

From starting and growing his video production company, Demo Duck, to his recent revamp of Heggerty, Andrew has always been an inspiration to us at Rubric. He was kind enough to share his entrepreneurial story with us along with advice on being a leader and navigating 2020.

How did you start your day today? Do you have a morning routine?

Today I woke up at 6:30 to read the Bible and pray. I try to do that 3 times a week, exercise 3 times a week, and rest on Sunday. At 7:00 “me time” is over, my 4 kids wake up, and it’s off to the races. After breakfast - I had Cinnamon Toast Crunch today in case you were wondering - I usually bike 2 of my kids to school then arrive at the office around 8:30 (I’m lucky to have their school and my work within a mile of my house). I keep a goals sheet on my desk that I review once a week. It outlines my personal goals, work goals, some leadership principles, and a few quotes that keep me motivated. My day almost always wraps up by 5:30 so I can be home for dinner and spend time with my family. I’m pretty serious about setting boundaries - no working weekends, no late nights - but that’s a topic for another day.

Could you tell us a bit about your background and about the (many!) businesses you’ve launched?

I’ve always been interested in business and the challenge of it. It runs in the blood. My Dad had his own business when I was growing up, and my great-great-grandfather started a company that is still in the family 150 years later. So I knew I wanted to run my own business at some point, but I wasn’t sure what to do (my wife still laughs at my ill-conceived college business ideas, like a hookah bar) and I didn’t have the confidence or experience to strike out on my own right away.

I spent 4 years at a small company as a marketing manager before launching Concept Feedback, a community for marketers looking for ideas to improve their websites. I spent about a year working on it as a side project before deciding to pursue it full-time. It scraped by for another year, but I never could figure out a solid business model (this was when crowdsourcing and freemium were all the rage) and I eventually sold it for an amount that paid for little more than a nice celebratory dinner out.

While Concept Feedback was struggling, I was doing some marketing consulting on the side to make extra cash, and most of my time went towards producing basic screencast tutorial videos explaining how to use a website or app. That was the genesis of Demo Duck, a business that came to life in a matter of weeks for a couple hundred dollars.

What was it like growing and ultimately stepping away from a company?

Unlike Concept Feedback, Demo Duck took off right away. I was able to use inexpensive search ads on Google to generate leads, and 6 months in, I was working on 30 projects simultaneously. At that point I did everything except the voiceovers (my friend Cisco, a radio host in Chicago, did those). Customers would fill out a form, pay online (pricing was flat fee based on video length), and submit a brief. I’d write the script, record and edit the video, and ship it off, sometimes doing everything over email without ever speaking to the customer. That seems hard to imagine now, but in the early days everything was very simple, and it worked.

Over the next year, I introduced animated and live action explainer videos, teaming up with talented freelancers and my first full-time hire, a project manager. We grew quickly, accelerated by videos for companies like Crazy Egg that would see success with our videos and share us with their networks. I also spent a good amount of time writing blog posts, optimizing our website for search engines, and eventually ranking in the top 5 for key search phrases like “explainer video”. Once search ads became too expensive, the entire business was built on organic word-of-mouth growth and search traffic.

After 7 years at the helm, I decided it was time to step away from the business. A number of factors went into the decision, but it was mostly that I felt like I had taken the company as far as I was able to and I needed a new challenge. I still remember having the conversation with Colin (an employee of 4 years at the time, and now the Managing Director at Demo Duck) outside on a 70 degree February day in Chicago. He was excited to have the opportunity, and so I spent the next 9 months grooming him for the position before stepping away completely at the end of 2017. I still own the company and check-in monthly, while he runs the day-to-day. Colin has been able to grow Demo Duck and inject new life, and I really couldn’t have asked for a better outcome.

I spent the next 18 months dabbling and trying to figure out what to do next. I invested in some multifamily properties, gut rehabbed a 4-flat (never again), worked at an elementary school, took my family to Portugal for a month, helped a friend grow his window installation business, and spent a lot of time reading, thinking, praying, and writing down business ideas. It sounds kind of great, but honestly I struggled through a lot of that time feeling a lack of purpose and a strong desire to get back to work on something I could fully apply myself to. For all intents and purposes, I was living the dream - financially set, “retired” at 33 - but like most things in life, once you get them you’re not satisfied. I believe God designed people to work and be productive, and that without it, there’s something missing.

What led you to invest in Heggerty?

My intention was always to start a new company, mostly because that’s what I’ve always done and I think there is some personal pride that accompanies starting “your own thing”. It wasn’t until talking to a friend and reading a book (Buy Then Build) that I started seriously thinking about trying to find a business to buy. Ultimately I decided that at this point in my life, with 4 young children, I didn’t want to start from scratch. I figured I would be better off stepping into something that already has a proven business model and simply leverage my skills to help accelerate growth.

Shortly after signing up for a few business listing sites (think Zillow for companies), I came across Heggerty. It pretty much checked every box on my list: serves a need in an industry I care about, has a small team, sells a product not a service, and has room for growth in the areas where I can add value (primarily marketing and digital). Plus, it turned out that the office was 2 blocks from my house! I’ve only been here for a year now, but it has been a great fit for me personally, and already a big success in many ways.

What excites you about being your own boss?

I love coming in everyday knowing that I can affect real change. If things are broken, I’m to blame, but I can also help fix them and chart a new, better course. I wouldn’t say I’m a control freak, but I do like being in the driver’s seat and having some control over my own destiny. I think my nightmare is being in a position where I do my best work and invest all I can into building a company, but ultimately have no visible impact (a cog in a giant machine) or control over a failing strategy.

What are some of the challenges?

When things aren’t going well, the boss is usually bearing the brunt of the burden. I tend to internalize things, which means I can let situations at work take over my thoughts and affect my mindset. I also have never enjoyed managing people. In fact, if I had my way, I’d sit in a corner and run a little web business with zero employees. It’s something I’m working on and getting better at, but it’s not natural, and it’s always messy. A great boss is intentional about being present and active in the leadership and mentorship of their team. That doesn’t come easy to me, and it takes practice.

How do you ensure you’re being a great boss and leader for your team?

Like any relationship, I think it’s mostly about communication and just showing up. I meet with my leadership team every Monday morning and we talk about what we’re working on and the challenges we’re facing. Every Friday I send a Friday Update email to the entire team that runs down the highlights from the past week, recognizes special contributions, and invites everyone to give shout-outs to their teammates. Once a quarter we have an all-hands meeting as well as performance reviews. Because I don’t naturally think to check-in with my team or recognize people nearly as often as I should, this cadence and schedule helps ensure that I do. I also try (and often fail) to do the simple things, like showing up, being present and available, listening and empathizing, and giving clear feedback and directions. These principles apply just as much to being a father and husband as they do in the workplace.

How have you managed / led your team during times of quarantine? Any new strategies or learnings?

Leading during a time of uncertainty and unrest, like we’ve experienced over the past year, has been a challenge. I think 2020 only increased the need for better communication from the top. When Covid began, I tried my best to be a stabilizing voice for the team, transparently sharing the challenges we’re facing as a business while being relentlessly optimistic about the future and the path forward.

After George Floyd and the racial unrest over the summer, I was probably too slow to speak up. I wish I would have addressed it sooner, but I was trying to “stick to business”. I just don’t think that works anymore. Once I did address it with the team, I received a number of emails thanking me for my willingness to address the topic head on, which in turn made my team feel like the topic is now on the table and they don’t have to hold it in anymore.

There have been a number of situations recently where I’ve had to take off my CEO hat and try to listen and empathize out of love and care for my co-workers. There is a lot of hurt and pain out there, and people are going through extremely difficult things right now. As a leader, I need to engage with that.

Where do you find inspiration—whether it’s business, marketing, or just life?

I usually find inspiration while reading books, having conversations with other people, and seeing examples of great work out in the wild. This is another reason I think boundaries are so important. Inspiration often strikes outside of the office when my mind has some breathing room. Without that time to disconnect and stop thinking about work, I find it’s hard to have any space for inspiration.

Any advice for other entrepreneurs that want to take the leap into being their own boss?

Just do it already! I get frustrated when people talk about doing something but take no action. For most people, the upside is huge, the risks are minimal, and the barriers to starting a business have never been lower. In the words of Kurt Vonnegut, “Of all the words of mice and men, the saddest are, ‘It might have been.’”

What’s in store for Heggerty in 2021?

We are doubling down on digital, launching a slate of new products (including a beautifully illustrated set of original children’s books that I’m very excited about), and trying to get better and better as a company one day at a time.

If you or someone you know is a BOSS, let’s chat.