The Mistake Is the Lesson: How Failure Built a Marketing Agency

Join Molly Baker for a candid conversation on building a marketing agency from the ground up. From a job hunt full of dead ends to a mentor's advice to stop working for someone else and start building something of his own, this guest shares what it took to launch a boutique agency and grow it into a full service creative shop. Together they explore learning to let go of control, saying no to clients that aren't the right fit, and why handcrafted creative will always beat AI generated shortcuts. The episode also dives into failure as a teacher, partnership, and the balance between strategy and creativity. Whether you're building a business or just trying to trust the process, this conversation offers a grounded look at what it really takes to grow something for the long haul.

MB (Molly Baker): Without telling us who you are, what are you thinking about professionally these days?

HR (Hart Roberts): I think about it daily, like customer touch points. That's kind of my day to day job, looking at how to optimize a client's digital reach. Looking at those touch points, whether it's the messaging, the targeting, the paid, the email, and figuring out the biggest impacts to drive results for our clients.

MB: What are you really good at?

HR: Our team always laughs that we're digital problem solvers. I think I'm really good at taking a challenge, asking the right questions, and figuring out the next steps. Over twelve or thirteen years of growing an agency, I've become a digital problem solver.

MB: How did you get good at that?

HR: Making mistakes, messing up. Just learning over time. You take on a project, learn from it, and grow your portfolio. It's mistake after mistake, learning experiences we call them, and then applying what you learn to the next project, the next client. Over time, you grow personally and professionally.

MB: So you're a believer that your mistakes teach you more than your wins?

HR: Absolutely.

MB: What's been the most pivotal moment in your career so far?

HR: I lived out in Telluride, Colorado. When I moved back east to Atlanta, I was on the job hunt, doing some freelance projects on the side but also looking for a job. Agency after agency were crickets. That stung. I don't think my work in Telluride really translated since it was still a destination not many people knew about at the time. But I remember that lighting a fire under me. One of my mentors took me out to lunch and said, "Don't work for the man, be the man." That was a big moment for me to pursue the agency and the work I wanted to do.

MB: So was that what motivated you to get started?

HR: Yeah. We were taking on projects on the side, but that really fired us up to just go for it. That was nerve wracking, but I had a really good business partner and friend involved, so we were in it together, which is really important.

MB: How long were you in Telluride?

HR: Six years. I went out for a summer, thought I'd just visit some friends, and never came back.

MB: When you went to start your own company, what were you most afraid of?

HR: Obviously failing, but also just not having the portfolio to back it up. We were fresh, so every project we took on became a catalyst for the next one. Not having enough experience or enough clients under our belt was nerve wracking for sure.

MB: Was your co-founder equally ready to jump in, or did one of you need convincing?

HR: He was in it too. The cool thing about us is we were at the same stage in life. When we started the agency, neither of us had kids, we both lived in Raleigh, and we were both getting married and having kids around the same time. That helped us stay on the same wavelength.

MB: Was there ever a moment early on where you thought it wasn't going to work out?

HR: All the time. In the early stages you compare yourself to other agencies and people a lot, and that breeds fear and doubt. There were a lot of "what are we doing" moments. I think those made us stronger and better as business partners and lit a fire under us to do even better.

MB: Who's been the most impactful person on you professionally?

HR: My business partner, Cam. He's almost the total opposite of me, and his strengths outweigh my weaknesses. We've been friends since college, then lived in Telluride together, and we just trust each other and have a good time doing what we do.

MB: Tell us who you are and what you do.

HR: My name is Hart Roberts and I'm the head of digital strategy at Chair8 Media.

MB: Tell us about Chair8.

HR: Chair8 is a boutique marketing agency here in Raleigh. We're full service, from branding to web design to creative content and more. We can take on your brand at any stage and help you find the channels that make the most impact to drive results.

MB: What does your average day look like these days?

HR: It's never the same, which is fun. Really my job is connecting the dots. It's looking at data and relaying with the team what's working and what's not, then prepping us for next steps. A lot of my time is in the web, paid, and email flywheel and how creative sits in the middle of that, which is my passion. But in the agency, it's really about connecting dots and making sure our team is set up for success.

MB: How do you feel about AI built websites?

HR: I've seen them and we've tested them. They work for certain clients and certain businesses. But we love the handcrafted approach, taking a Squarespace or Shopify site and intentionally building it with content we create in house, with SEO and generative engine optimization in mind, and making it truly unique. A lot of the AI stuff feels generic, almost like it's pulled from other places. If it works for your business, awesome, but we value the handcrafted final product and the relationship along the way.

MB: What's been the best and worst part about founding and building an agency?

HR: The best part is definitely the team, building it over the years and watching teammates move on to bigger and better things. The worst part is trying to fully disconnect. The agency is your baby, so there's never a quiet moment. There's always something you could be doing or some fire to put out.

MB: What lesson has taken you the longest to learn as an agency owner?

HR: Learning how to not be involved in everything. The agency is your baby, so you want to be in everything because you're excited about the work and the clients and the team. But I thought about the best managers I ever had, the ones who trusted me and stepped aside, and I realized that's really important. It took a while, but it's had real benefits.

MB: How did you get more comfortable letting other people run things?

HR: Staying in my lane. Focusing on what I had to do and not getting distracted, and building better structure within the organization so it's clear what I'm in charge of. That's happened in the past couple of years and it's really helped.

MB: What's been the biggest thing that's changed in the actual work you do?

HR: Early on we took on anything and everything to build our portfolio. Now it's rewarding to be able to say no to things and really take on the relationships and clients we want, no bad blood, just knowing what we're not as passionate about anymore. It took a while, but it's a good feeling.

MB: Do you guys specialize in a specific industry?

HR: Not really, but we fall into three buckets. Real estate and development, where we work on projects before they even break ground. CPG, which I love because it's a fun space to play in. And hospitality, restaurants, some hotels. Even the outliers go through the same process, building a great relationship with the client and thinking about the touch points that create the most impact for them.

MB: How do you balance leading strategy with partnering on the creative side?

HR: I'm a creative at heart, so I have to have that outlet. My creative outlet is photography. I've always taken photos and enjoyed that side of creativity, and I'll still go out on shoots with the team sometimes. It was tough moving away from leading creative day to day, but I knew there were people in our agency better at it, and I wanted them to lead the charge. We're about fifty fifty, thinking analytical and creative, left and right brain.

MB: Is your co-founder leading creative?

HR: He is. All video production, photo shoots, content creation, that's his side. I'm more strategy, which falls into the web, paid, and performance marketing side.

MB: What's a project you're most proud of?

HR: It goes back to Murphy's Naturals, a local CPG natural mosquito repellent company. Another pivotal moment for us was moving into a shared workspace when we came to Raleigh, where we were founding members. Alongside us was the Murphy's Naturals team, and they trusted us early on and let us run with the brand. Seeing your content in Costco or in a flight magazine is pretty cool. It gave us a lot of confidence early on and it's just a fun brand to work with.

MB: What's one thing you wish you knew earlier in your career?

HR: You don't always have to have it figured out. When you graduate college you feel like you have to follow this natural progression, but you don't. Try something new, move out west, you never know what's going to happen. Growth comes from doing things, messing up, and adjusting along the way.

MB: Do you feel like if you hadn't gone to Telluride, you wouldn't be doing what you're doing today?

HR: I think that's right. I had the opportunity to run a website on a really small team out there, and that's where I fell in love with the marketing world. We didn't have the budgets bigger resort towns had, so we had to get scrappy, and that's where we learned how to hustle.

MB: When you were twenty one, did you think you'd be here in your career?

HR: Absolutely not. I think once I moved out west after college and started getting my hands into more marketing, more hands on things, that's when I realized this could lead to something bigger.

Find Hart on Linkedin or visit the the Chair 8 website!

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