Ciara Pressler and Cathey Armillas: What Makes an Entrepreneur?


Last month, I sat down with Cathey Armillas at the OpenSignal studios in Portland, OR, to talk about smart entrepreneurship and what it really means to go for what you want in business. Video above; transcript below!

Welcome back to our program, I’m Cathey Armillas. I’m here today with Ciara Pressler; she is the owner and entrepreneur of Pregame, an amazing organization that helps small businesses and entrepreneurs be their best. Welcome Ciara, how are you?

Thank you Cathey. This feels very formal compared to how we usually hang out.

I know it’s very formal but it’s really cool to sit down and actually have a formal conversation with you because you’re actually a freaking genius. Seriously, and I think what you’ve brought to Portland is amazing and I kind of want to talk to you about that, and I want everybody to hear about pregame and what you do. So you started this organization because you wanted to help entrepreneurs get you know a hand up, right?

Exactly. I’ve been working with entrepreneurs my whole career small businesses startups in lots of different industries. I grew up with entrepreneurial parents so it’s it’s been in my blood and all around me my whole life, so you know, naturally you pick up pick up on the patterns of success and failure. You know I was a consultant to entrepreneurs in my first business helping them with brand strategy communication strategy, which inevitably moved into pricing products you know people everything but I wanted to create a way that more people who get this good information.

Yeah, and they don’t know but I coach at pregame for you. I’m one of your experts and one of the things I think that you’ve done incredibly well that I don’t think a lot of people take stock or value or understand when they’re starting a business is that there’s all these components to your business besides what you’re good at or what product or service that you’re doing that you need and you’ve created this amazing space where there’s all these experts that do all these little intricate things they have access to some amazing, like if you can’t make it in that environment oh my gosh, you can’t make it anywhere, right the whole New York thing.

It’s true and I really believe that there are geniuses out there when it comes to coaching and consulting entrepreneurs but nobody has all the answers. I certainly don’t and so in the areas where I’m not an expert I want to bring in other people who can help people make the right decisions. It’s ultimately your decision how to start and grow your business but you need input from people who actually know what they’re talking about and we are in an era of a lot of self-declared experts and people are getting the wrong information and they’re wasting time money and energy and ultimately burning out because they are taking action on advice that isn’t really sound.

Or worse they’re not they’re not getting advice at all, so it’s almost like there’s no in-between. I see they don’t go out and seek any advice or they take really bad advice.

Yeah and you know something you mentioned was that entrepreneurs you know, they know what they do. You know the business the product they know that really well especially if you’re a solopreneur you’re freelancing, you’re a creative entrepreneur it’s really about being able to do that product all the time and we neglect to think about the fact that we need to run the business of that product as well and spend some real time and and focus on that in order to make it a viable business. That’s something I see more in first-time entrepreneurs than second time entrepreneurs. People who are starting their second business tend to be more adept at answering an actual market problem and taking themselves out of it it takes about two years to get that you go out of your business.

Right, well it’s kind of funny too because you think about the switch of it to some businesses don’t understand that there’s the business piece behind their business and then once you really get to the the highest of entrepreneurialship I think is when you flip at the other direction and you go I want to create any kind of business, but a business that will run well as a business. So it’s it’s being in the business of being in business. I think that to me that’s what an entrepreneur really is as opposed to somebody that’s just self-employed and does something they’re good at their craft and they happen to be a like a freelancer or they’re self-employed.

Yeah, that’s a good distinction. If you just want to do the thing you want to do, the time whenever you want to do it that’s a hobby, if you want to do the thing you do all the time and have someone take care of everything else that’s a job, if you want to do other thing you do all the time and also sell it and choose your customers and create this structure around it that self-employment and if you want to take yourself out of it eventually that’s a business. I just made that up you know.

That’s amazing we’re gonna use that! It’s amazing you know you describe that so beautifully and it’s so true because a true business is one where you can remove yourself from it. So going back to that though because I really the value that I know that you bring Ciara is that you help people find that in themselves and you help them bring those two things together like okay you’re really good at this but how do we turn what you do into a business. So tell me what’s like what’s the biggest challenge with entrepreneurs or you know tell me what you work with the most.

Oh wow, there are a few. I think on the note of the product as people really fall in love with the idea of the thing they want to create at the risk of not listening to the market. So what does the audience want versus what you want to create and of course you can be very creative and bring something new to market but the additional challenge with that is that you have to educate people and hold their attention long enough in this day and age to educate them on why it’s appropriate for them and why they need it. That’s a big big part of it another part I think especially when you’re on your own and you’ve come from a job especially if you’ve come from a creative job is people don’t charge enough, you know they think okay I make you know X thousand dollars a year in salary at my job so that’s what I need to make in order to be self-employed. No, there’s additional expenses you know you add in another third to that at least. Another thing really is mentality and attitude, the people who I deem most successful because my definition of success is to you know be happy and healthy and live a full and balanced life. Those people are the ones who have a great attitude and go into their businesses with a spirit of service to others and it really becomes an exercise in self-actualization to go you know really high level with it, but you know if you’re running a business especially a service based business which is most of my clients you have to know exactly how much of your heart to put into it and how much of your ego to take. I struggle with it every day it’s a it’s a learning process.

Yeah, yeah wow that’s so beautiful that you brought the mindset piece into it too there’s again this is this is why you’re sitting here and this is why you’re amazing at what you do because you see things from this holistic value but a lot of people don’t put the the stock into the mindset piece of it or that balance of pulling the ego out and and adding the passion or adding you know the good pieces in. Also I you could probably see a lot in the work/life balance right you know I think sometimes people I remember when I first started my business I thought I thought it was the coolest thing in the world to send somebody because I was always up till like 2:00 3:00 in the morning I thought it was really cool to send somebody an email and then I realized later I’m like people don’t actually respect you and they know when they know you don’t when they know you don’t know how to respect your own time they don’t respect you as a person. It’s a weird distinction to like go well it’s kind of weird to think that if you send somebody an email at midnight they’re not going to respect you, but honestly it shows your mindset and and and there’s a there’s a fine line between your dedicated you’re passionate you’ll do whatever sound like you have no balance.

Yeah, one of my new year’s goals this year is to get better at boundaries and that we do workouts around that a pregame is defining like what are my standards for an engagement what are my boundaries with my clients, because you know if somebody text me at 9 p.m. on a Sunday to like register them for a class or take them out of a club I’m not doing that ya know.

I draw my line there, yeah, boundary there.

But it’s challenging and it depends what stage of life you’re in as well. You know I was thinking just yesterday about how if we’re artists people really romanticize being completely enveloped by your art and like I was writing a new song till 2:00 a.m. on Friday and all of that but if I’m working on my website till 2:00 a.m. then that’s unhealthy. So you kind know there’s a balance but you know the first year or two of your business do demand a lot of sacrifices you know. You have to put the investment in and what happens is people don’t plan for it to take a long time to grow, or even reach a point of sustainability and they get burned out, they quit they give up because it’s honestly easier to have a job. You know if you don’t like your job go get a different job. There’s a lot of jobs and the paycheck magically arrives in your bank account, and taxes get paid, how does that happen it’s so magic when people tell me like have a cold so I’m staying home from work.

I’m like that way you could pick up the phone and call somebody and tell them that you’re gonna not do anything.

I know it’s true. It’s just it’s a different demand, I mean the fourth month of my business I had walking pneumonia and I showed up every day. I’m not saying that’s good for me or good for anybody else but there are different demands.

Right, yeah no, I love that you beautifully touch on, I mean just somebody here in your interview right here even if they weren’t an entrepreneur they would get a really good sense of what you know, what’s life like on that other side, and yeah there’s pros and cons of course and you’re describing some of them. I’d love for you to tell us quickly like how does pregame run it’s such an amazing magical wonderful place.

It runs on magic. You can buy a bottle of it through Pregame you know, but I do think a lot of people sell their services that way like it’s magic, just buy it and you’ll get magic. We are the antithesis of that, so you know a big part of the first first premise of pregame is that we tell the truth. So you know I really push back against our culture of like follow your dreams leap and the net will appear because there’s an asterisk there right, there’s a caveat – yes follow your dreams but the risk is you’re gonna have to work weekends, you’re gonna have to pay your own health insurance. Like this is what it means in the real world and I think it’s great to be positive and optimistic and we absolutely try to keep a spirit and energy of optimism every day in every class we do at pregame. But it’s really important to base the premise of our decision-making in reality. Pregame is like a gym for your goals,w e have workouts every day.

It’s so amazing.

We have classes every single day around accountability getting advice from experts like you and people in all different areas of business and people get a membership and they have unlimited access to all these experts, these accountability sessions, guest speakers, field trips happy hours, it’s a total lifestyle of just being your best everyday.

The entrepreneurial lifestyle, never thought about that is such a good tagline. 

Hashtag start-up life.

I you know of course because I teach there and I know how I know I’ve gotten to know a lot of your members and there’s such amazing dedicated entrepreneurs. It’s so cool that they have this ease of access to just be able to jump in and you know go hey I really need, I really need to work on social media marketing right now, boom I’m gonna pop in and do this now, and then later I need to work on this or I love that.

Yeah and the value of that because a lot of our experts don’t even sell an hour of their time. You know they’re doing multi-thousand dollar engagements with big companies but they’re willing to come there and give back and I know that’s a big part of your philosophy is to give back as a mentor. So you’re getting time with these amazing experts for a fraction of what it would cost to hire them.

Oh a fraction, if you could even get the time with some of these people. Your friend list is amazing Ciara! I cannot believe the people you know. Yeah it’s fantastic. So uh, you know wrapping up this has been amazing. I appreciate all of this great insight. I love the little, I love your little, you got to give that a name it was amazing cuz this whole thing between-

Oh it’ll be branded.

Oh it’s gonna be branded by the end of the day. From hobby to actual business, I loved it. But you know last question like what would you, what advice would you give somebody if they were wanting to start a business? It’s like what what if somebody came to you to see how you know, you do this, like I want to start a business what would be like your one piece of advice?

Yeah you know balance what you want to do and what you’re willing to work on every day, and live and breathe with what other people need and want, and always stay humble about what the next step is, and ask for help. I am terrible about those last two but it’s a process. You know this is a great tool for learning those those qualities, right. Ask for help because there’s people around you who know more than you do who are more than happy to help, and if you can’t find any come to Pregame.

Yes, exactly! So on that note I actually want, I know that people listening and watching are gonna really want to know more about you because you’re amazing and and Pregame’s a great place. Can you tell us how they can find more information about you?

Yes, Pregame HQ is in the pearl district in Portland Oregon. You can come to our Clubhouse for classes it’s at and if you’re outside of Portland you can’t make it go to and you can read articles by all of our experts about how to redefine success for yourself.

This is fantastic Ciara. Thank you again so much for being here.

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