On today’s episode, Ciara Pressler joins us from her studio in Pregame HQ! Ciara is dedicated to discovering the best business ideas & practices through the advising she provides to entrepreneurs, business leaders, and creative professionals. She has managed marketing and communications initiatives for clients from startups to the best-known brands in the world. She has been a guest expert on business, including segments for NBC, ABC, NPR, and The Huffington Post. Ciara is the author of two business/career optimization books, creator of entrepreneurial development courses, and a guest speaker for conferences, schools, and organizations. Today, we talk about designing businesses, burn out, what makes a sustainable business, and how to build a profitable, better business!
Kristen G: Hi. Welcome back to Up, Right & Better, the podcast where we talk about growing businesses up and to the right, and up and better. On this show, it’s not just about scaling for scaling’s sake. It’s about making organizations that deliver value to everyone involved. I’m your host, Kristen Gallagher.
I am so excited to have Ciara Pressler on the podcast today. She’s both a coach to me and a coach to many others in Portland both formally and informally, and I got the chance to meet her early on in February this year when I hosted a program for the Portland Startup Week events and she’s just a stellar speaker and I’m thrilled to have her on today to talk about her background in marketing and business strategy, and how she’s applied that to small business and so I want to go ahead and start there. Welcome, Ciara.
Ciara P: Thank you so much. I am excited to be on this podcast and I’ve listened to a few other episodes and already learned a lot from you too so thanks.
Kristen G: Good. I’m glad to hear that. Let’s start with your background. You have this extensive experience in marketing and business strategy, and I’m curious, why did you decide to leave the so called corporate world and start applying that knowledge to small business?
Ciara P: I’ve never been a corporate person. I’ve never thought of myself that way. I’ve always worked for small businesses other than a stint at Nordstrom in college, but I grew up with parents who are entrepreneurs and self-employed in different ways and so, I think that’s always been part of my makeup one way or another. Also, my first career was in the performing arts, which is bootstrapping at its best.
Kristen G: It is, yes.
Ciara P: Yeah, it’s in there. I started my consulting practice working with startups and organizations and creative professionals in 2009 as a result of a layoff in the wake of the recession and it really happened organically. I didn’t set out to start a business, but a lot of business landed in my lap as a result of the work I had done previously so that was the beginning.
Kristen G: That’s the best way to start, right.
Ciara P: Yeah, it really is and it’s funny because the landscape has changed so much. A lot of the things I did then to start my business from a just business mode or survival mode are the things that people are doing a lot faster now because we figured it out. Can’t think of a specific example, but we were talking this morning here at Pregame about how everyone’s a business coach now and so, when you say I have this extensive background, I don’t think of it that way. I just think I have a lot more experience than people who are doing business coaching or consulting of some sort. I spent a lot of time building up my reputation and legitimacy in my first years as a full-time consultant, but people don’t really have to do that now. They just need a really great photo shoot.
Kristen G: You’re so right. No, you’re so right and I remember my first year of business in Edify, I kept searching online for support and for help and ideas, and you can download 300 million different kinds of ebooks about marketing and this will grow your business 50 million times and it’ll be six figures in six months. It’s just like most of it is pure BS and I was listening to another podcast yesterday morning about the only way to really sustainably scale your business is to sell, right, and it’s to do the hard work that you’ve done and that experience that you’ve done. I’m curious, what are you doing now? I know you in the context of Pregame. How are you applying that experience to Pregame?
Ciara P: Yeah. I get a lot of the people who have done those courses that are sort of magic pill solutions, whether it’s an ecourse or an ebook or a conference or a coaching program. Often online programs do that because they have to keep your attention to get you to sign up. I get it. I get it. It’s good marketing, but I’ve worked with so many people at this point, so many entrepreneurs, leaders, founders, executive directors, artists, people who are leading a project or a business or a team at this point that I see patterns of how it works in the real world.
I don’t know. I think I am an optimist, or else I wouldn’t be in business for myself, but I’m a realist and I want to know what works in the real world. I like ideas and theories and trends as something to talk about, but the ones that I teach tend to be based on what is actually working and so, Pregame was my way of scaling that. I can only work with a small handful of people one on one at a time and I want to be able to work with more people so, I created Pregame as a way to be able to deliver these success patterns and what actually works to more people at once and make it more affordable for people who are just starting out.
Kristen G: Right. Exactly. You were just starting to touch on what a sustainable business is through that idea of these are not just ideas and theories, but this is practical knowledge about what can make a business sustainable and scalable so what makes a business sustainable to you in your opinion?
Ciara P: There’s this paradox, right, because the kind of person who’s going to be a founder or an entrepreneur, someone who’s creative enough and risk tolerant enough to start and run a business is going to have certain personality traits that make it more likely for them to take that leap, but those are the exact same personality traits that can work against them for what it takes to get the business to profitability and sustainability, right. You want to be creative. You want to be a good connector. You want to be a good sales person in terms of talking about your business and getting other people excited about it, but if you’re so high on the idea and the excitement of the newness and disruption and all that, it can become very boring to do the day to day work and that’s where I see people, they just get tired of their business. It’s like people who really love the act of falling in love, but they don’t want to do the long-term relationship work because …
Kristen G: It’s true.
Ciara P: Yeah, I’m like, “Sorry, this is not glamorous. Every entrepreneur I know …
Kristen G: Yeah, this is the ugly stuff.
Ciara P: Yeah. The business nextdoor to mine last week during our heatwave, the owner of that business with a team of 20 was outside scooping ice into snow cones for the neighborhood, and I was like, “This is real entrepreneurship.” She’s serving the community. She’s out there doing it herself, not just making her team do it. I get on my hands and knees and clean the floor if I have to and whether that’s a metaphor or whether it’s literal, I think you have to have the humility if you don’t have the very long and deep runway of a bank account that can hire a bunch of people to do that for you. Even then, I’m not sure it’s healthy to outsource everything because I think you need to take responsibility for what you’re creating and know the nuts and bolts of things before you hand them over to other people. All that said, the characteristics of the founder or founders and how they manage their own personality traits I think is a really big deal, bigger than I previously thought actually.
Kristen G: I think it is. You see it in a lot of startup type businesses that are maybe funded before they actually have sales or market share to show for it and you do see that founder trait show up sometimes where they’re so excited about the idea and they can sell the idea, but then when it comes down to actually building it and building a team that can really deliver, then it’s called into question sometimes.
Ciara P: Yeah. I have this radar for that personality type, right. I always find these people and it’s very obvious to me right away because I’ve worked with so many of them and because I grew up in a family with that spirit. I work well with those people because I can help them figure out where the points to how to help them get excited about smaller strategies within the business, not just the whole business concept itself. If you want to be restless about something, be restless about your marketing and your sales because that’s the thing you’re going to have to be doing every day for the rest of the life of your business.
Kristen G: Right. I was just talking to a friend and fellow business owner yesterday about how excited I am for my vacation and she said, “Is it really bad? Am I going to be a bad business owner by telling you that I am tired and it is hard to do the day to day work?” I said, “No.” Of course, I think it’s important to admit, and you and I talked about this before, burn out and all of that, that it’s important to admit this is hard work, but that is what it takes to create a sustainable business.
Ciara P: That’s why you can’t do it by yourself. I don’t have a co-founder. I think having a co-founder or a team is fantastic. Of course, there are cons to that, you’re splitting up the pie. It might take longer to make decisions. It really has to be the right match, but even if you’re going solo, you have got to have a team around you. I call it your advisors.
I have a weekly call on Thursday mornings with a mentor who I can just vent to if I need to and I have other people I can call. Luckily, my brother helps me with finances. I have another friend who has a similar business to mine so we can bounce ideas off each other where we respect each other’s opinions enough to hear what the other person is saying. Not everybody should play that role because not everybody has good advice, but whether it’s some sort of peer accountability group, an actual coach or consultant, I think you need several people that you meet with regularly in order to stay healthy.
Kristen G: I completely agree. I think now in Edify’s third year of business, I’ve finally hit that stride of I have a weekly call with my both friend and accountability partner who has a similar business on the other side of the country, and we have in place now the team members who can be that owner of different parts of the business while also working together and providing that expertise and advice to you and challenging you, too, sometimes because I think you mentioned that some of the traits that make people really good business owners and not good entrepreneurs can also trip them up. I’ve known that very well about myself.
Ciara P: Yeah. You need someone to check your BS.
Kristen G: That’s very true.
Ciara P: Who has permission to call you out on it like, “Actually, that’s not true. Actually-
Kristen G: Yes, actually that’s false, yeah.
Ciara P: Yeah, but it’s funny. I had the idea for Pregame in some form or another for years, but the last piece of the puzzle that I didn’t have yet, which I learned from my personal life is that it’s so important to have an in person peer group. I knew that from my friendships, but I think it didn’t click until in the last few years, which is even if you have these calls, you still need to have the mirror neurons of being in person with somebody for human connection and normalcy because social media is the antithesis of that. You think everybody is doing well and that you’re the only one experiencing problems because you can’t tell that people are just writing about one kind of great thing that happened in their whole week while the rest of their week was a total mess.
Kristen G: Right. Exactly. I know. I remember my first couple of months after I had quit my job to run Edify full time, and thinking, “God, everything is so fragile right now,” right. It’s like it can be good one day and really bad one day and it’s less than 12 hours later and I remember walking down the street. I think I was on Hawthorne here in Portland and I was thinking, “Oh, my God, all these businesses are potentially so fragile,” right, but yet people keep coming to work every day. I’m also an optimist-realist so I’m not saying that in a negative kind of doomsday way, but gosh, it’s really hard, right, and you have to keep coming back day after day.
Ciara P: It’s just a different kind of hard.
Kristen G: That’s true.
Ciara P: I was raised in such a way that this kind of hard suits me. It’s hard to go to a big corporation every day where you don’t really have a say in anything and you have a very tiny role to fulfill in a massive machine and that would be very frustrating to me because I like to fix things and make systems better, and I’m very much of the school of thought of like if it’s not working, change it.
Kristen G: Yes, exactly.
Ciara P: If it’s not working anymore, change it. That’s why I love small business because you can actually do that, but what the recession did for us in 2008 and 2009 is showed us that everything is volatile. If a company stock drops, they need to unload 10,000 employees to make their stock more attractive, then you’re out of a job even if you work for like a blue chip company. I think that this surge in entrepreneurship that we’re currently experiencing was fueled by the recession and people feeling uncertain no matter what kind of business they work for.
Kristen G: Right, right. Speaking of some of those challenges, but opportunities at the same time, what do you think are some of the most compelling challenges and opportunities that are facing, I call them small, but scalable businesses today?
Ciara P: So many things. Everything seems to be changing so quickly especially because of technology, but one thing that’s really standing out to me right now as a potential obstacle for businesses is idealism. It’s when you get too stuck in how you think things ought to be in a way that is not appropriate for business. I think that’s great if you’re an artist. I think that’s great if you’re at a nonprofit to a point, but too much idealism will kill your business because you still have to be able to sell the thing, right.
Kristen G: Right.
Ciara P: If you’re in a hybrid creative business, it’s a little more clear. Like if you’re a graphic designer or an interior designer or a chef, it’s very clear that you can’t only just make or design what you want everything to look like, but your flair and what you bring to the project is very important. The way that relates to even like a technology business is you might need a piece of software to do X, Y, Z, but if your audience only needs it to do X, Y or if they only want Z, that’s what your business is. So you have to be, as Steve Jobs said, “Stay humble, stay foolish,” you had to be humble and foolish enough to not let your ego get in the way of what the market wants.
Kristen G: That’s a really interesting idea that you could actually hamstring yourself by focusing too much on what you think the vision is rather than listening to what the market has to say about it.
Ciara P: Yeah, basically, around the two-year mark when I’m working with an entrepreneur, that’s when they’re ready to give up on their own idea of what their business has to be. If people, if they insist, “This is our lead product, this is the product everybody wants,” but people keep calling them for a different product …
Kristen G: Maybe pay attention.
Ciara P: Eventually, yeah, eventually, maybe make that what you lead with because that’s what gets people in the door. I’ve made that mistake, too, but I think the solution is you either package all those things together or pivot your business, which is just …
Kristen G: Yeah, yeah.
Ciara P: Startup culture way of saying, “Be smart and use common sense.”
Kristen G: Exactly, yeah, all these coded words that really mean simple things. Speaking of coded words and simple things, things that we read about all the time, things like automation and AI and the pace of change, how do you think that those things play into the day-to-day work of small upstart businesses that might not be say a venture-funded company?
Ciara P: Yeah, I think you need to think ahead a little bit. First of all, stay informed. Be in the news. Go to conferences. Go to networking events. Know what’s going on so that you know what’s being developed because if you’re in a bubble, if you’re working from home and you never leave and you’re not talking to other people in your industry, you don’t know if somebody’s already 10 steps ahead of you doing the same thing. Then think ahead about where is the development of technology taking us? Is what I’m building or what I’m providing as a service going to be automated within a few years and then, I’ll be automated out of a job? I think we have enough information on our fingertips to be able to look into the future a little bit and decide what are things that software won’t be able to do in my place in a year or two or in five years?
Kristen G: That’s a really good way of thinking about it. How do you think that you would build a business that’s both profitable and better for the community? I’ll let you decide what does better mean to you.
Ciara P: Yeah, I was thinking about this idea of better. I think a healthy business is usually better in general, but for some businesses, better is providing jobs for the community and for other ones, it’s giving back more tangibly and directly to the community like having a triple bottom line. How do you do it? I don’t know. Every business is different. Profitable means you’re making money, you’re not wasting it and digging yourself into a hole of debt, but some people can afford to do that. Listen, not everyone who starts a business is doing it to make a profit. Some people are just doing it for fun. If that is your goal to maybe establish yourself or get an idea out there, just build an app for fun, go for it, awesome. If your goal is to make money, which is the goal of most businesses, that involves the humility that we talked about and paying attention to the numbers and being honest with yourself about what’s working.
Kristen G: I completely understand. I think that honesty is a good thing to hone in on. I think oftentimes, I see with businesses that have scaled really quickly, they’re not always honest with themselves about the hidden pitfalls that they could be running up against. What is that? You mentioned runway, what is the runway that I have to make this thing happen and do I need to make a change? Do I need to pay attention to what my community, what my market is asking me? How do I as a business owner define better and how close am I to that goal?
Ciara P: I love that. I love looking at this as a spectrum between profitable and better, and you just need to decide where your dial is going to be on that spectrum, what is most important to you. If it’s all the way over on the side of better, maybe it’s a nonprofit that you want to create or a B Corp. If it’s all the way on the side of profitable, maybe it’s not even worth it to you to own the business. You just want to go make money. I’m not saying one’s better or worse than the other. I’m just saying be honest with yourself about why you’re in the game so that you don’t self-sabotage.
Kristen G: That’s such a good point. That’s really good. As we wrap up, what pieces of advice would you have for listeners who are trying to build a scalable or a profitable or a better business?
Ciara P: When I first start working with somebody, we do a kickoff session and we spend an hour talking about their whole entire professional context and their goals, and starting to build a strategy for what they want to do or a game plan as it were. An exercise I keep coming back to in that is this quadruple Venn diagram and I ask people what do you love, which they pretty much know what they want to do all the time. Then the next circle is what are you good at? Now sometimes, people want to start businesses doing something they don’t actually have any experience in and I say, “Well, then you’re going up against people who have 10 years of experience doing X, Y, Z. Does that make any sense? Will people pay you for it?” The next circle is what will people give you money for, right? The final circle, what do people want? Finding something that’s at the intersection of all four of those areas I think is a really solid start to a business model.
Kristen G: That’s a very solid start. I wish that I had done that when I started. I think maybe it would’ve helped me see some things that took me a while to see, but given that, are there any other resources or things you want to share with listeners?
Ciara P: Oh, wow. There’s so many things out there. The number one thing I want to share with people is that you are the CEO of your own career, even if you’re not the CEO of your own business and if you are seeking help or advice, it’s up to you to vet that. I think a lot of times, we make decisions in a panic about taking that overnight magic pill ecourse or working with that person who promises us success in six weeks. Real life doesn’t really work like that.
The people who are successful in those things are successful in most things because they have these traits of discipline and a good attitude and a solid business model and being humble about the work that they’re doing. Work on that, but then when you’re evaluating like who are going to be my advisors, who’s going to help me build this business, please, please, please, ask the right questions. Develop questions ahead of time that you want to know. I’m going to be offering a list of those questions on my website that people can download. Be sure to comparison shop too so you know what’s available to you.
Kristen G: Such good advice. Thank you. Speaking of websites, where can people go to find more out about you and about Pregame?
Ciara P: Pregame’s website is pregamehq.com and on social media, you can find us at that same hashtag, pregamehq and then, my personal website is ciarapressler.com.
Kristen G: Thank you so much. Ciara, it’s been wonderful talking with you. I really appreciate you and look forward to talking again soon.
Ciara P: Thanks, Kristen.
Kristen G: That’s it for today. Thank you so much for joining us for another episode. If you’d like to ask a question or suggest a guest, email me at firstname.lastname@example.org. Until next time, grow better.