The Transcript

How to Build a Business That Lets You Live the Life You Want

Voiceover: Welcome to Hack the Entrepreneur, the show which reveals the fears, habits, and inner battles behind big-name entrepreneurs and those on their way to joining them. Now here is your host, Jon Nastor.

Jonny Nastor: Welcome back to Hack the Entrepreneur. I am so glad you decided to join me today. I’m your host, Jon Nastor, but you can call me Jonny.

My guest today has been involved in branding and marketing strategy for over a decade and has worked to shift the status quo with brands such as Apple and Morgan Stanley. He is now the founder of Design Pickle, a graphic design subscription service that offers unlimited requests and revisions for a monthly fee.

My guest is also a creative consultant at Digital & Disruptive, where he hosts workshops to help companies rapidly develop marketing or build brand strategies. He is a charitable guy and has been on the board of directors for the Alzheimer’s Association and is the co-founder of one small business, which provides entrepreneurial education for young people.

Now, let’s hack Russ Perry.

Welcome back to another episode of Hack the Entrepreneur. We have a very, very cool guest today. Russ, thank you so much for joining me.

Russ Perry: Yeah, you bet, Jon. Thanks for having me today.

Jonny Nastor: It is my pleasure. Let’s jump straight into it, shall we?

Russ Perry: Absolutely.

Figuring out Ways to Build a System

Jonny Nastor: Russ, as an entrepreneur, can you tell me, what is the one thing that you do that you feel has been the biggest contributor to your successes so far?

Russ Perry: Hmm. I know luck is one of those cop-out answers I probably shouldn’t throw it there. I think for me, it’s being able to assemble the right resources to put together in the business. I think a lot of times, as I look back at the failures that I’ve had, it was when I have tried to do too much myself. That’s a common trap a lot of entrepreneurs fall into, because we’re good at everything, and we know exactly what we want.

To be truly successful, you have to figure out ways to build systems or bring on people to expand whatever you’re doing beyond yourself. I tend to have a knack for that, and whether that’s getting people on my team or creating systems with technology and software, that’s where my strengths probably lie. I’ve been able to use that through several businesses and growing them and making a little bit of money along the way.

Jonny Nastor: Which isn’t so bad.

Russ Perry: It’s not. I’ve also lost a lot of money too, so …

Jonny Nastor: Of course. We all have.

Russ Perry: It goes both ways.

Jonny Nastor: Yeah, and the luck — there obviously is a certain amount of luck in timing, being in the right place at the right time, online or wherever you are in your business. But you have to be there. You have to be doing that for luck to find you, right?

Getting Lucky in Business (Is Not about Being Lucky)

Russ Perry: Yeah, and luck, you could look at luck as just a probability type of thing. I have a friend who would always win these contests. I’d be like — his name’s Dave — “Dave, you’re so lucky. You always win. You win these crazy contests to go to Las Vegas and TVs,” and he’s like, “Russ, I enter like 20 contests a day.” He’s statistically more probable to win.

I think for luck, it’s the same thing. People who are lucky aren’t necessarily getting more advantages than other people or the universe is favoring them. It’s just that they’re putting themselves out there more. They’re trying more things. They’re creating more connections that could lead to other stuff, and that to me is really how I interpret luck. Just creating more of a mathematical probability that you’re going to meet or get whatever you want.

Jonny Nastor: Exactly. Exactly. I’m glad you made that clarification, because you’re right. It’s like, looking at Dave, it looks like he wins all the time. But he also enters all the time.

Russ Perry: Yeah.

Jonny Nastor: People can look at you and be like, “Oh, Russ, you’re so lucky with business and stuff.” It’s like, “Man, I work my ass off. I have for a long time.” It’s not really luck. That’s cool.

Your Past 10 Years Is Just Practice for Today

Russ Perry: My business coach said that the last 10 years have been practice for today. I was lamenting over a couple of businesses I had over the last decade. She’s like, “Oh, that was just practice for today.” I was like, “That’s an interesting way to look at it.”

Jonny Nastor: That is. How long have you had a business coach for?

Russ Perry: Man, I’ve always had one off and on. I find myself to really thrive in that kind of environment, the accountability and the perspective that a coach provides.

This current one I hired at the beginning of the year, really right around when I was launching Design Pickle. I’ve been working with her, her name’s Dena Patton, I’ve been working with her. We work every other week, have a call, and it’s great. I love it. I highly recommend getting a business coach. That’s a really powerful thing, especially if you’re just on your own, doing your own thing, because you don’t really have that accountability like you would if you were in a team.

Jonny Nastor: Yeah, no, exactly. That’s why, when you mentioned it, I wanted to ask. How did you go about finding her? How in the past have you gone about finding a business coach?

Russ Perry: This specific coach — it’s a quick, funny story — I was at a conference, and she was speaking and presenting on some other topics, and mentioned she did coaching, but coaching for women. I was like, “Oh, that’s a bummer.” I thought she was really smart and really liked her content. So I actually referred her to my wife, who just started her business. I was like, “Hey, you should look into a coach.” My wife is very cynical of the idea of coaching. She is like, “So I’m going to pay all this money to talk to somebody? That sounds stupid.”

She got off her intro call with Dena and hired her on the spot. I was like, “Holy smokes. If this woman’s good enough that Mika, my wife, is going to hire her on the spot, then I should talk to her.” I talked to her and she’s like, “Well, Russ, yeah, I work with women business owners, but I also work with really smart men.” I was like, “Oh, that’s a genius sales line.” I had to hire her at that point.

Other than that, I think coaching is very personal, so there are all different styles of coaches. It’s frankly easy to find them, searching in your local community for business coaches. There are all sorts of training programs they go through. Some are trained, and some aren’t, but for me, I’ve always just come across them, usually in a conference setting.

Jonny Nastor: Nice. Excellent. I love how the past 10 years has been practice for today. That leads us nicely into this question of, in every entrepreneur’s life, there seems to be this time when they realize one of two things. Either they have this calling to make something big in the world, something bigger than themselves, or as mostly seems to be the case, they find they simply can’t work for somebody else.

Can you, Russ, take us back and tell us what side of the fence you sit on and when you discovered this about yourself?

Russ Perry: Yeah, it’s really clear for me. I was working for Apple here in Arizona, where I’m at. I worked for them in college at the university doing stuff for them, and that was fun. I helped them launch the iPod back in the day. Then after college, I was working for them as they were launching the retail stores.

However, I had just had my first daughter, who will be 10 this year, so that’s about 10 years ago. I was freelancing and doing my own thing, but I wouldn’t have considered myself an entrepreneur.

I was working for Apple, and then I was doing some stuff on the side. I actually, when my daughter was born, was really limited with the amount of time I could take off of work, because me and her mom weren t together. We were just friends, and whoops, we had a baby. I was trying to navigate all these doctor’s appointments and seeing my daughter and all this stuff. I was like, “This sucks. I hate working for somebody.” Requesting time off just to be able to go to a doctor’s appointment seemed like the craziest thing for me.

Again, the stars aligned, and I had one friend who provided me with enough of an opportunity to go out on my own. In 2005, I actually started my first agency formally. I had filed the business paperwork and that was that.

I think I was the latter of your two options, thinking I don’t want to work for somebody. I don’t want to have to navigate a paid-time-off policy.

Jonny Nastor: I guess that’s still your case.

Russ Perry: Yeah, yeah.

Jonny Nastor: The further you get now, right?

Russ Perry: I would say, I was technically unemployed last year. I closed my last business in September of 2014. I had no plan, so there were real conversations with my wife about getting a real job. I kind of cheated. I did consulting, which is like getting a real job, but kind of not, so that was good. But becoming an employee again and going through all that, it’s almost like my mind couldn’t comprehend that. Then I figured out what my next thing was going to be with Design Pickle.

Jonny Nastor: Yeah, that’s interesting. That’s an interesting place to be in, especially after so many years on your own. You said your wife’s an entrepreneur as well?

Russ Perry: Yeah, she’s a new one. It’s a scary place. I was really freaked out, to be honest. I didn’t know what I was going to do, and I have two girls now and one more on the way. My wife wasn’t pregnant then, but I still had a family. To not know what your plan is is really scary. For an entrepreneur who usually always has a plan, that’s a very unusual place.

Jonny Nastor: Yeah. Was there a process that you could, say, replicate or go through again to discover where you wanted to go and focus your efforts, which became Design Pickle, but like you said, you had no idea.

Russ Perry: Yeah.

Jonny Nastor: That’s a hard place to be.

Russ Perry: Yeah. I started really poorly in terms of figuring out, and it was whatever idea came into my mind, I started being like, “Oh, I’m going to do this. I’m going to think about this.” I was really dangerous, because I was most certainly in a place of scarcity. I was in a place where everything seemed like a good idea, frankly because I didn’t know what I was going to do.

I actually also hired a coach, a different coach this time — this was in October — a guy named Taylor Pearson. I had not met him, saw some of his writing on some forums and things, a really prolific guy. I hired him. I was like, “You seem like an analytical guy. Help me sort through all this.”

We did two exercises, which was really simple. One was describe your life three years from now, irrelevant of your work. What do you want your lifestyle to be like? If you’ve accomplished this and this is what’s happening, you’re really happy. I wrote that.

Then he’s like, “Okay, I want you to make a decision-making filter.” These are the things that need to be true for you to achieve that three-year outcome. For me, I had a lot of travel and time away and visiting Asia with my family and doing a summer in Italy. For my decision-making filter, my next professional thing clearly would need to be remote. I would need to be able to work with it anywhere in the world. Maybe I would have an office, but my business couldn’t be dependent on me being in a physical location.

I created this list of decision-making filters. I think there was like seven or eight items on it. When I took all my ideas and ran them through this filter, all of them failed. None of them passed, and so I had no ideas left in October. I just consulted. I had a couple friends that I helped out with their marketing stuff, and I didn’t come up with new ideas.

Every time a new idea would come up, I would run it through this filter, and it wasn’t until December when the idea of Design Pickle came to my mind. That was the first idea that had passed all the filters. That’s when I started to realize I was on to something.

Jonny Nastor: That’s really cool. Basically, it’s like working backwards, right?

Russ Perry: Yeah.

Jonny Nastor: Think of the business you want to create and the life you want. It was even outside of business, but what life do you want, which is even more important. Otherwise, we just create businesses, and then three years from now, you’re like, “This isn’t what I wanted,” but you’re stuck in this business you created. Now you’re actually creating what you want, the life you want three years from now.

Russ Perry: Absolutely. It’s hard to change things. Even one year into a business, it’s super hard to change stuff, to go from an office to a virtual-only environment. I was actually talking to some guys today, and one guy was like, “Russ, it seems like you have no friction with employees. You have this model that you’ve used for Design Pickle, and everything seems to be self-sustaining.” I said, “Yeah, it’s because I didn’t want to manage anybody,” so the first person I hired was a project manager.

That was by design, because in my little decision-making filter, I wanted to have a lot more freedom. You do have the luxury when you’re in my position to do it, but I totally agree. Kind of reverse engineering out what your lifestyle is and what things are like for you, irrespective of the actual business or whatever, seems to have worked well in me now making decisions based on that. I still make decisions based on those decision-making filters when I’m hiring and with different strategic things.

Jonny Nastor: Have you got to go to Asia with your family yet?

Russ Perry: Not with my family. My wife is from Japan. She lived most of her life here, but her mom’s from there. I did go to Japan in 2011.

Jonny Nastor: Nice.

Russ Perry: That was really amazing. Yeah, that was awesome. Our goal is to go back there. Her family lives in Kyushu, and so we want to go back there and spend some time. Maybe a summer.

Jonny Nastor: You’re setting up your business to allow you to do that.

Russ Perry: Yeah. My business is totally remote. I run most of it from my laptop. I don’t have an office. My staff, everything, all the systems are in the cloud, and we have a lot of team around the world right now. That’s one angle that we have for Design Pickle...