What is the first step to building a creative consulting business? Learn how to find motivation within yourself. Michael Zipursky’s guest in this episode is Bobby Gillespie, founder and President of The PROPR Design. Bobby shares with Michael how people were questioning his move when he left his last job. Even his parents were unsure, even when they were proud of him!
But he proceeded to build his own creative consulting business anyway. Through constant learning by exploring, doing, and making mistakes, his company earned multiple awards like best branding agency and best digital marketing agency. Join in the conversation and let Bobby’s experience inspire you to build your own consulting business. Tune in!
I’m with Bobby Gillespie. Bobby, welcome.
Thank you, Michael. It’s a pleasure to be here.
We have been talking about this for a while. I’m really excited to have you on the show. For those who aren’t familiar with you and your company’s work, you are a Creative Director of brand strategist and you started your company Propr Design in 2014, which is a branding agency based in Baltimore. You won many awards, including the Best Branding Agency and the Best Digital Marketing Agency in your city. You have accomplished a lot. You have been working with some fantastic clients. I feel honored to witness some of the growth and what you have been doing. It has been pretty amazing.
Let’s go back in time a little bit and explain how do you get started. Before you even entered the world of working at other design and branding firms, which I know that’s part of the story from before starting your own company, what were you doing? How did you get into the world of design, multimedia and art? Was it right out of university or is that what you were studying in the university? Take us back to the early days of Bobby G.You learn by observing, exploring, doing, and making mistakes. Click To Tweet
It’s a very atypical journey for me. I was always a very creative kid. I was fortunate my parents had recognized that and they stuck me in art school around Philly. I grew up in Philly. From an early age, they saw that I loved to draw and be involved with art. When I’ve got through high school, I had not the best guidance. I took every class art I could take on weekends, summers. It was all the time. My guidance counselor pushed me nowhere and my Art teacher suggested I go through the University of Chicago for Medical Illustration and that didn’t appeal to me. In my mind, I felt that there was only Fine Arts. I didn’t realize that there was design, illustration and animation. It took until three years of college as a Science major, which I like not love.
On a road trip to Florida for spring break, we stopped at Savannah College of Art and Design and I had this major epiphany that there were creative careers that I could sink my teeth into that weren’t Fine Arts so I wouldn’t be selling paintings on the corner. When I’ve got back to school, that’s when everything changed and I rarely spent the rest of the second half of the year focusing on going to art school and pursuing that path in the creative.
I can’t imagine you doing Medical Illustration. You mentioned your parents encourage and guide you towards exploring that artistic side. You are a parent yourself, what advice would you offer to parents or people who are running consulting businesses, agencies and so forth who have young ones? Is there anything that you look at from what your parents did with you that either you feel worked well or didn’t work and things you are also now incorporating with your kids?
The one thing that set the tone for myself and I try to do that with my kids is to get them to observe. It’s watching, paying attention, and seeing how things are. That applies to life in general, business and everything, observing, seeing, thinking about it. If your kids seem to be drawn towards creativity, whether it’s drawing, coloring, telling stories or making up stories, encourage that creativity because when we are kids, we are encouraged to play. When we are grownups and we engage in something that we would call a play, it’s looked down upon. That’s the opposite of how you learn. You learn by doing, by exploration, making mistakes and observation.
Push into all of those different experiences. I have three college degrees. That’s a lot of different experiences. I had a lot of jobs that I look back on and I hated who I worked for but loved what I did. Those are great experiences where I observed a lot. When the time came that I had the opportunity to lead people and then start my own company, I learned a lot about what not to do. When I had the opportunity, I treat people well and I give them autonomy to learn, explore and make mistakes. It’s the constant pursuit of one, curiosity but two, learning. Those are very related. Anytime you can encourage and foster those, characteristics in people, children, adults, anybody, do it. It’s worth it.Motivation comes from within you. Click To Tweet
After university, you studied and you’ve got these degrees, you also then worked as a senior designer at multiple companies. Talk us through that experience. Your time working at other organizations before you went out on your own and started Propr Design, what are some of the key lessons, insights or experiences that you picked up that if you look back now, you feel like, “Those helped me to start my business or to be who I am.” What was most meaningful or impactful for you during those years of working for somebody else before you started your own thing?
I think back to my favorite bosses and unfortunately, none of them were in my industry. One of my favorite bosses of all the time was somebody who ran concessions at the Academy of Music in Philadelphia where I was a bartender for a while. He treated people well. He didn’t judge and we were all accountable for our bank and our bar. He taught us what we need to know and then he trusted us. My first job in the industry was at a dot-com back in ‘99 and I’ve got that experience again. There was no boss so it was quite different. We were all autonomous but we were all accountable to one another working on a common goal. We are all very young in our early twenties wearing shorts and flip-flops to work and showing up at 10:00 and headed to the beach on Friday. It was so ideal.
There was a taste of something with both of those experiences that I was seeking throughout my career until I started my own company. I wanted to be treated like an adult, have autonomy, be empowered to make decisions, can make mistakes, be curious, learn and not being focused on blind items, creating red tape and complexity. It was like a drug that I was feening for about fifteen years. I’ve got fed up with the industry and how other agencies were operating to foster that culture and commitment to that lifestyle when I started my own company.
You were thinking about starting your own company for many years. Was that playing in the backyard?
I’m not necessarily thinking about it but I had career goals. When I moved to Baltimore, I fast-tracked those goals because it was a new town, a new chance and a new start. I wanted to be a senior art director or creative director of an agency and within four years of moving here, I had that job. When that ran its course and there was time for me to go, that’s when I was like, “What do I do now?” They are running my company for seven years but in hindsight, I was always being groomed to be an entrepreneur and be the owner of a company. By that time, I was like, “I never imagined this once in my life,” I always sought that leadership role, wanted to bring about change, and question why we did things the way we did them because there’s got to be a better way. This sucks. I became unemployable because of my ideas, opinions and my motivation to act on them.
What were you saying at that time? Were people supportive? Did people think like, “You should stick in the corporate world?” What were those around you telling you at that time?
You know how the world acts and says you have to stay in your job and be a good employee but I never care what anyone thinks. You asked me earlier what my parents were in terms of supporting. They support me. They are not necessarily sure what I do, that’s okay but they are incredibly proud of me. My family is proud of me. When I left my last job, people were like, “What do you want to do?” I was like, “I don’t know but I’m excited about it.” It was a 50/50 split, whether I was going to get a job or start my own company.
Some things had to fall in place with my family and whatnot but every day, the needle moved more towards me starting my own company because I felt that my motivation comes from internally. I just need support from my family to believe in me. I don’t need someone to push me at all but I have felt that there was a better way to run an agency. If I was going to bring my all to it, I might as well make my dreams come true, not someone else’s. The pressure is to fall in line, have 3 years here and 5 years there. That’s how I see in my eyes.
When you started Propr Design, what was one of the biggest challenges? What was something that was unexpected or what were you banging your head against in the early days?
There’s a piece of advice I give to anybody reading. When you start your own company after you had some success, you don’t have to start over and you don’t have to earn your keep again. Pick up where you left off because you earned it. Having the confidence to make those decisions, charge what you should charge and go after the clients that you best fit with, that’s difficult early on. For me, the biggest challenge was separating myself from my history so where I worked before. I had to regain my reputation to myself. That was my initial focus.
One of the most surprising and gratifying aspects of running a business is being able to change people’s lives. Impacting our clients, focusing on the service and the relationship is different but also my team. Being able to offer them what I’ve never got through my career, that’s why I started my own company, a place where they are treated like adults, respected, have autonomy, empowered and hold one another accountable, the simple things we want, all those things. In the first few years of starting a company before I had any employees, it was a lot of knowing what not to do through my experience. Not necessarily having a roadmap for what to do or how to accelerate through the different corporate lifestyle cycles that we all experience, feeling comfortable, being aggressive with it and asking for help.
You mentioned in the early days that one of the challenges was how to take all of your years of experience and expertise, and figure out how to position or focus on that. How did you navigate that? Working in other companies or running into design firms, you are going to work on a lot of different types of projects and different industries. What was the path for you in terms of deciding where to place your focus and what you wanted your company to be known for?
I’m big on identifying weaknesses and working tirelessly to new worked in the strengths.
Can you give an example of that?You need to understand your priorities to see clearly where you’re going. Click To Tweet
When I started the company, the director of sales where I was the Creative Director was a senior sales guy, a good friend of mine. He was dangling it out. He’s like, “Should I come?” I resisted that because I want to know what it takes to be successful in the business and sales role so I can hold people accountable for it. No one sells me, my company and our services better than I do and that still holds true all these years later. I’m big on empathy and understanding, and it’s challenging for me to be able to hold someone accountable in those roles when I have never done it. I wanted to sell hundreds of thousands of dollars in projects and I did. I continued to do that but that’s not my primary focus because we don’t sell, we consult.
There are a lot of branding and design companies out there. Clearly, you have been very intentional in creating differentiation between what you do and what others do because that’s one of the reasons that you left the industry. You didn’t like what you saw what was going on. You could focus on working with any type of company in the world that needs branding or design services. What has been the path of choices that you have taken to differentiate Propr Design? How did you in the past and how do you now think about differentiation? Who to focus on in terms of being an ideal client for your company?
This is what I think about all the time. Positioning our clients, being able to help clarify their messaging and we meet our own dog food on that non-stop. Who’s our ideal client? Is it a vertical or is there a horizontal? It’s a little bit of both. How do we come to that? The formulas are similar but the variables are unique. The first thing you’ve got to do is identify, which variables are right for you and your company. The variables for us are while niching down into a vertical meaning industry or size is very advantageous in terms of focusing your finite marketing resources, which is in a very infinite game but we look for need.
For us, it’s what their need but also, we use that mid-market size as being able to deliver based on a budget that works for us. How did we come there? It’s where the opportunities led us early on. I come from a heavy digital marketing consumer product and an eCommerce background. We do a little bit of all that but what we focus on, which makes us different, is not jumping into implementation. We start with brand strategy and when our clients don’t have one, they are struggling with it or it’s up here, that’s where I step in and I facilitate what we call Brand Clarity Workshop. It’s where we extract that from their heads and make it a very tangible piece to roadmap their future.
What was missing when I started my company is now something that we provide our customers. To take their insecurities, whims, egos out of the equation and focus on what’s best for their brand and what’s best for their target audiences then it makes it very easy to evaluate every decision they are making as an organization. Not just on design, copywriting, photography but on hiring and where they should seek opportunities. It’s very empowering this approach for our customers. You can go anywhere and get a great website. What’s your website or what’s a house cost? Determining where they should best invest their money, their resources and focused their energies, we help them understand that to where they see their priorities as clearly as we go.
You and I have had many conversations on that topic because it is a very powerful differentiator. Most or many design companies and branding firms, if a client or a company approached them and said, “We need a website.” They say, “Sure. We can build you one. Let’s get started.” What you do is slow things down and help them to identify like, “Let’s figure out first why do you need a website. Where is it coming from?” You look at and make sure that the foundation is very strong. It’s the same mindset that we have as we work with consultants.
People will say, “I need more leads. I need to improve my marketing.” “Do you know who your ideal client is? Do you resonate with them? If not, you can do all the marketing in the world and throw lots of money at it but it’s not going to get you the result that you want.” That foundation is so critical and very powerful in the way that you are doing it. Let’s come back to the early part of your career and then we will jump forward to a bit more of what’s happening now in your business. When did you know or have a feeling like, “I have made it. I don’t need to go look for a job anymore. I have confidence?” It might not be that the things are going on 100% the way that you want all the time but that feeling of like, “I’ve got this.” When did that happen?
I remember a couple of years ago, for the first time, when we were still billing hourly, although we don’t do that at all anymore, I was on the beach and had people working while I was on vacation, I said to my sister-in-law, “The company is making money without me now.” That was interesting and nice. The transition coming out of 2020, we all know 2020 into 2021 around the New Year, I had the realization that this company is almost running on its own now. I have been talking to a lot of my friends, colleagues and team about this like, “If the company was to slow down, I would have to consciously sabotage it.” That was a very indescribable feeling because that doesn’t make sense in the way the universe works. The one variable in there that makes it make sense is people.
You are marketing, people are aware of you, you are having a consistent message, impact on your clients, making a level of revenue and it’s increasing. All these things are happening at the same time. It’s people selling to people providing services to people. That was when the whole flywheel concept was like, “This thing is humming. We don’t have to push as hard.” In 2020, we had to push super hard but it turned out to be our best year despite all the nonsense, sadness, pain and suffering. 2021 is our best year but it was a sensation that was like, “This is all clicking.” It was after many years in business that that happened. I will never forget it and I won’t let it stop spinning.
You are an amazing person to work with, Bobby. You are in our Clarity Coaching Program and I remember you shared this thought about where things were in the business. During that period of 2020, where a lot of business owners were feeling they weren’t moving at times as quickly as they want and clients were delaying things, there was a period before the New Year where many people, even though they were having good years, at times, it’s the ups and downs of business. You are very open to that. I respect that you were open to sharing what was on your mind.
I want to know because you have this mindset, which I think is unstoppable. It’s something that I respect. I want you to share with people how do you navigate those times when your mind is telling you, “Things aren’t going the way that I would like them to go. I’m feeling a little bit stuck and it’s hard to push through.” What have you done? How does your mind work to allow you to push through that and get to new heights?
There are a couple of things that we have to come to terms with. One is the humble factor. We all realize that a lot of the stuff that we are seeing in the media is BS, meaning nobody knows what they are doing. A lot of people are insecure, scared to go into business or take a big plunge because they feel like these stories of overnight success are real. The overnight success takes fifteen years and $25 million of your parents’ money to make it happen. That’s just the estimate.
What gets me through it is what also fulfills me with my business. It’s relationships. It’s keeping it real. Being authentic, open and honest with people, being yourself and saying, “I don’t know.” My favorite response to something I don’t know is, “I don’t know but I can’t wait to find out. I can’t wait to learn more.” Instead of people saying things like, “We can do that,” then scrambling, trying to figure it out and embarrassing themselves. I appreciate the kind where its flattery will get you everywhere it may. It’s that authenticity of the relationships, communication, allowing yourself to be vulnerable because you don’t have the front and fake it. Just be yourself and have fun.
Were you always that way as this growing up? Was there an experience? I will speak for myself. Back in the day when I was early stages of building our 1st or 2nd consulting business, especially when I was in Japan is surrounded by a different culture, people are much older than I was and the language that I was trying to work to improve on, all that stuff. I felt at many times extreme vulnerability, self-esteem and a lack of confidence but I always pushed through because I think that comes back to my upbringing around sports.
Living in a different country and then coming into feeling like an outsider, I always want to prove myself. That’s where I channel it through sports and into business but I wasn’t open about that vulnerability. Not until years later did I start to expose and tell our story as a company. I’m wondering, where does that come from you? Were you always that way, you say it as it is or is that through some experiences, through training or something else? Where does it come from?
I feel that at this stage in my life, my career and my business, it affords me that ability for extreme vulnerability. It hasn’t always been that case. I was in great suffering but I have always been very opinionated and I have always marched to the beat of my own drum. I’m a middle kid, I grew up in Southwest Philly, rough and tumble neighborhood, and I went to Catholic school where they try to beat you into being a follower, someone that was there to take orders. They tried but they failed because I had my own ideas. What may be a challenge when I was in the wrong role at companies was that I had my own ideas.
I’m very confident in that. I like to give the advice that is the smartest person in the room. That’s never been the case but what I mean is be the most prepared. Like you, I’ve got tons of books behind me and boxes of books all over the office in my house. It’s that insatiable curiosity and seeking self-improvement to be better but also be proud of yourself. I mentioned being humble but also be proud of yourself, what you accomplished and your ideas. I don’t give a shit what anyone thinks. I have never cared what anyone thinks even though in the neighborhood I grew up with, I knew what everyone thought because they said, yelled or beat it into me. I always had my own ideas and ways to do things.Despite all the nonsense, sadness, pain, and suffering, this year can be your best year. Click To Tweet
You made an important point, which many entrepreneurs and certainly, entrepreneurial consultants are guilty of. We tend to focus too much on the future and not enough on what we have accomplished. I don’t mean to drag the past behind us and all our time thinking about what went wrong. Look at what you have accomplished over the last 30 days, 1 year or 5 years because we are thinking about that next goalpost into the future and we are not appreciating what we have accomplished to the point where we are. Being present, appreciating the past and being proud of our accomplishments.
I read a book and it mentioned people thinking about their legacy too late in life. It’s like, “What’s the legacy you are creating for yourself?” Having things like being able to have my kids at the office. That warms my heart to no end and have them grow up and talk about that long past I’m gone. The legacy of books all around, helping, impacting and empowering people. You look back on that and you should be proud of what you will accomplish. Some of us have that innate ability to have a vision for a future state that even fewer of us have the guts to make that future state of reality.
Let’s talk about your business and how your role has changed. You have a team and you have worked hard at cultivating a great culture among the team. I want to hit on a few different things related to this. The first is how has your role changed over the years? You started as Bobby. Take us through some of the different hires that you made and based on those hires. How your mindset changed as you put those different people in place to grow the business?
Many in our predicament have experienced the litany of hats we have to wear. Eventually, it’s no longer good enough to wear that hat and applies to everything. Sometimes things need to be good enough but when they are no longer good enough, you need to up your game there. Over the years, I hired a designer the first day. She worked with a contractor but then she was my first full-time employee building that relationship, her helping me grow and let go. I’m a designer but I don’t design anymore.
We glossed over that point. That it’s such a sticky area for so many people to get to where you are knowing that you have that deep expertise, knowing that in your mind, you are the best person to do that. Here you are trained as a designer doing design work and then now, you don’t do design. You give direction and you work with your team. What was that like? Was that an easy thing for you to hand over? Take us through the mindset, the thought process and the battle that went through your mind at that time.
It’s easy when it’s someone else’s company. When I was a Creative Director, I could hire somebody and then direct them but there’s very little risk and it’s not as scary. With my own company, you feel that your reputation is at stake. I mentioned good enough, for us, it’s up here. It’s a really high bar. Finding the people that are aligned with what I care about most, they care about it, too. That’s the most important thing. Being able to get out of that and let go, it’s a trust issue. We are the leaders of our company.
We have to put our people in a position to be successful. If they are not successful, it’s us. Here’s the quick part of that. You trust your gut, you do due diligence, you make a decision, then depending on how the situation works out, act just as quickly. You have to fix it, remedy it or remove something from the equation. It’s that whole paralysis seeking perfection. There is no perfection.
What have you found most helpful in your company to vet and qualify to ensure that somebody has the right ingredients and that might fit for culture? It sounds like for you, culture is such a big part of it to bring. For us as well, building our team. Think about culture and values. Even when we haven’t necessarily been as open and sharing our values, we tend to attract people with who we do share our values through what we are doing. Are there any words of advice or anything that you have found that’s helpful in the hiring process or the team-building process? Let’s start with the hiring process first.
It’s the same thing. It all starts with values. You compete on values, you attract on values, you build on values. Everything else is negotiable and should change over time. Your values are your values. When someone is the wrong fit or our client is a wrong fit, it’s because your values aren’t aligned. Nothing else. If you don’t know what your values are, start there. When you are hiring folks, be completely honest. Don’t bullshit people. Don’t create this fictional environment that is very appealing but complete BS.
I have experienced that a million times where I have done all my due diligence to ask all the right questions, I get the job and all of a sudden, I’m in there and I’m like, “This is nothing like they said it was,” so it bounced. It’s the same thing. If they are lying to you, they are bullshitting you. If you are bullshitting people, then you are going to get bullshitters attracted to that. If you identify your values as what’s important to you and you live by them, you abide by them, you work towards them, they are aspirational, then you are going to attract similar people.
I want to go to empowering your team. You mentioned that trust is a big factor. Is there anything that you do from a structural perspective? Do you follow a certain meeting cadence? Do you use a certain process or a system to ensure that your team is getting things done but also the overall culture and environment is conducive to people operating at high levels and everyone is working towards growth? Are you in constant contact? Do you have any system or process that you use with people?
We have a weekly standing meeting. Everyone has gone virtual. We were all already mostly virtual with the teams all over the country at this point but we still have the office if anyone wants to come home once it gets cleaned. We have a standing weekly meeting where we go over projects and make sure that people have the support they need and the opportunity to ask for help. That’s important. We want people to be accountable, which includes asking for help. Support goes hand-in-hand with empowerment. We stay out of email so it’s Slack. If someone is going to be out of pocket, then they text me or Slack me, I will get back to you.
It’s managing expectations but promoting open communication. Once everybody went virtual, we started to do the weekly check-in. We allow time for people to bullshit, not lie but catch up and talk about nonsense, pop culture or the news. It’s people. Create an environment that your people are comfortable in and creating an environment that your people have what they need. There’s something that we resist. It’s standardization.
Once things become standardized, over time they become dogma. Once they become dogma, they become unquestionable. That’s the worst-case scenario. We like the beta. In the group, we talk about standard operating procedures. That’s a piece but we come BOPs because it’s a starting point that we are constantly reflecting on and asking, “Could this be better?” That’s the foundational aspect of my business and how we operate with our clients, we don’t set anything and forget it. We question, “Can it be better?” That’s where our creativity comes into play.
That constant search for continuous improvement. It can be small things or big things but oftentimes, small things compound and lead to much bigger things. You mentioned that 2020 was your biggest year and 2021 is going to be your biggest year. If you had to hit on 1 or 2 things that you think have the biggest impact on your business, things that you have done, you have learned, what would you say that those things are?
This is a softball one. I’ve got to throw love back to the group. You have thought about a lot of the stuff that’s new to me. The corporate life cycle is a very similar journey for a lot of businesses, business owners and consultants. You get to these glass ceilings and then when you do, you either stay put, go backward or breakthrough. That breakthrough requires help. Reaching out, asking for help and finding a community that you feel a part of that supports you, that’s critical to me. Finding anybody, that’s why these consultants exist and we were here, we are going to help you through this.
I hired my first two employees in 2020 as well. That’s a major milestone for me. I went to school for design, multimedia and science. What the hell do I know about business? I know it by experience, by reading and by other people’s experiences but getting over the hump with making your first hires, that’s insanely challenging until you do it. You are like, “No big deal.” It’s seeking people to help you navigate through the waters and being appreciative of the relationships that you come across on that journey.
Bobby, before we wrap up, I want to make sure that people can learn more about you, your company and see the great work that you do. It’s visually appealing and there’s so much more beyond the visuals and the brand. Things look good, which is always nice to see you. That’s certainly as it should be from a branding company. Where’s the best place for people to go to learn more about your work and connect with you?
Our website. That’s the humble betting marketing activity and if it isn’t, it should be. Our website is ProprDesign.com. We do some social media but our clients aren’t on social media. Our Instagram is interesting and very visual. I’m very active on LinkedIn myself, which is, @ThatBobbyG and you can get my nuggets that come out here and there.
You have been doing some cool stuff on LinkedIn with videos over the last little while. What has been your experience with that? You went from a very slow start to be ready to jump off the running block but once you did, it and now feels like you are getting some great momentum with these videos. What has been your experience and how are you feeling about it?Seek self-improvement to be better. Click To Tweet
It has been great advice. You gave me that advice and you gave me a framework to follow on how to get started. My first video it’s that pursuit of perfection. I recorded it, I sent it to an editor, I paid money out and then I was like, “I could do this in-house and have it be good enough up here,” then it comes up like the topics are already there. They are in the conversations we are having, my team seeing things. I’m like, “Do a video on this, please.” It takes me an hour a week to do a video or throw out a meme.
All we are doing is professing our values, professing our positioning, our thinking and our approach. We are offering people some of our humble words of wisdom to think about things a little bit differently and see a different route than the traditional method of hiring some folks that are going to add you into the next dollars.
They have created increased engagement and people are contacting you. There has been a beneficial business impact.
We are leaders in our industry. We are supposed to be. Where’s the evidence of that? You can’t keep the evidence on case studies on your website. You’ve got to put your thinking out there. Some of the things I say are quite controversial and damn right they are.
I don’t think anybody could have guessed that based on our conversation at this point.
It’s helped to be a contrarian and that leads us into interesting waters. We give this advice to our clients when they have a team that’s all buying for leadership and it’s like, “You’ve got to do twenty posts in a month and then start doing it like this. Start doing videos. Keep posting.” It works within the algorithm so you get more exposure. When people are researching and googling you to hire you as a consultant or your agency, it starts becoming a deep archive of good content that never stops being given.Manage expectations and promote open communication. Click To Tweet
I want to encourage you to check Bobby’s website, check all the work that they have put in their portfolio, connect with Bobby on LinkedIn and watch his videos. He puts out some great content with some ideas that aren’t the standard ideas. That’s what makes them interesting. Bobby, thank you so much for coming on here. I appreciate you sharing some of your journeys with us and I look forward to talking soon.
Appreciate it. I will see you soon.