The Transcript

The Journey From Travelling Poet to Online Entrepreneur

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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: We are back with another episode of Hack the Entrepreneur. I am your host, Jon Nastor, but you can call me Jonny.

My guest today is a poet turned tech junkie and entrepreneur. After receiving a graduate degree in literature in 2000, my guest headed for Europe, where he sang rhymes to crowds for five years before moving to Arabia to teach Shakespeare to American troops.

His interest in tech was sparked while working for a VC firm in Utah. His due diligence work there taught him one thing. He wanted to be the startup, not the investor. He got the chance in 2011 when he launched Post Planner.

From there, my guest and his co-founder grew Post Planner from a simple scheduler into a powerhouse content curation and social publishing platform.

Now, let’s hack Josh Parkinson.

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Welcome back to Hack the Entrepreneur. We have a guest I’m really, really excited to talk to. Josh, thank you so much for joining me today.

Josh Parkinson: It’s a pleasure to be here, Jon. Thanks for having me.

Jonny Nastor: Pleasure is all mine. Let’s jump straight into this. Josh, 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?

People Who Don’t Give Up Win, Those Who Do Not Disappear

Josh Parkinson: Probably just not giving up. That’s really it in the end because the entrepreneurs who don’t give up are the ones that win. The ones that give up disappear. In my business — I’m in social — we’ve been on the Facebook platform for four years. We’re a fully bootstrapped company. We’ve been through some really hard times that would, for many other entrepreneurs, I’m sure they would have given up and tried a different sector, a different application, or something.

But I stuck with it, and my partner, Slav, stuck with it with me. Now we have a bigger team and all that, but really, in the end, the entrepreneurs who make it are the ones that just don’t give up and just believe in what they’re doing and just keep going.

Jonny Nastor: I think you’re totally right. There’s also a time where you have to stop certain things, right? Not stop being an entrepreneur all together, but what is it, Josh, that tells you that Facebook is the right platform and even the changes that it throws at you or something like that, that you just have to keep going and it’s the right thing to do? Is that a gut feeling you get, or how do you work that?

Gut Feel and Data: How It Helped Josh Find His Platform for Business

Josh Parkinson: That’s a good question. It’s partly a gut feeling. It’s partly based on data, that Facebook is the elephant in the room. It’s the gorilla in the marketplace in terms of social. If you’re doing social and you’re not on Facebook, then you’re missing 85 percent of the market.

I really wanted to be in the social and the content space from the beginning. ‘From the beginning’ is maybe not the right way to say it. I didn’t foresee that, that would be the direction we went with the application. Once we started to go in that direction, I realized how passionate I was about it, how much I enjoyed it, how fascinating it was, and how fun it was to build a product around that.

When problems with the Facebook platform came up, to give up on Facebook would make the prospect of building what I wanted to build infinitely more difficult and less profitable. My co-founder, my CTO, he has a background in the Facebook platform. That’s what he’s an expert on. It was a bunch of factors like that, that I knew I couldn’t give up on Facebook as a platform for the business.

Now we’ve expanded outside of Facebook for the first time in the last couple of months. We started posting to Twitter. We’re adding different types of feeds, content feeds, inside of the app from other networks. In the end, that’s really where everyone is spending their time, most of it. You got to get on Instagram. Instagram’s blowing up and these other platforms, but right now, Facebook is the number one place.

Jonny Nastor: Yeah. I want to know when you figured this out about yourself. There’s a time it seems to be in every entrepreneur’s life when they realize one of two things. Either they have this calling to make something and make a difference in the world or, what seems to be the case mostly, is they just simply cannot work for somebody else. Josh, can you tell me which side of the fence you fall on, and when this happened for you?

How Josh Used Independence as a Motive to Be an Entrepreneur

Josh Parkinson: I think I’m both, but I’m definitely the latter. I’m not very good at working for other people. I want to lead the charge. I’ve always been that way. I want to be the leader and direct things, be the visionary for whatever I’m doing and be independent if I have to do something, not have to put work into something that I don’t believe is the best thing to do.

That goes so far back into my history, probably into my childhood. My parents would probably say that I’ve been that way since I was 3 years old. I can’t remember ever being different. That’s what I tell a lot of people who ask me when I decided to be an entrepreneur. I just say, “Dude, I’ve been an entrepreneur since I was 3.” It’s a mindset.

It’s really about what you’re talking about. It’s this drive to create a world for yourself, create a living for yourself. It’s a different mode. It’s much more risky. You never know what’s coming around the bend, but it’s fun as hell, man. I can’t imagine doing anything differently. I never really have.

The only period in my life where I didn’t, I had more safety, was when I was in academia and studying. While I was studying, I was teaching, and for a period in my life after studying, I did teach a little bit. That’s really the only time where I had a job like that where it was secure. I knew what was coming next, and I knew I could stay if I wanted to. There was a different joy in that — the joy of teaching and having students, learning, and that kind of thing.

Still, even as a teacher, you’re kind of an entrepreneur — especially at the collegiate level. You’re creating your own syllabus. You’re creating your lesson plans. You’re directing the classroom. You’re the leader in the classroom. Even with the way I did it — I went and spent three years on military bases in the Middle East during the wars in the 2000s — I was alone out in these military bases, kind of an entrepreneur, building these satellite university sites and being the teacher as well. Even in those times, I was an entrepreneur.

Before that I was a singer in a band in Germany for five years. I was the lead singer. I was the band manager. I was the guy who got us gigs. I was the guy who took us out to the street and all that kind of stuff. Like I said, from the beginning really, that’s been my mode of living. I can’t really imagine anything else.

Jonny Nastor: Wow. So much correlation to how I probably would have answered that. I love it.

Josh Parkinson: Yeah, we’re not all that much different. Entrepreneurs in the end, founders, especially the ones who are bootstrapped I’ve found, are like this. This is the way they live.

Jonny Nastor: Even down to the point of being in a band. I’m a drummer.

Josh Parkinson: Nice.

Jonny Nastor: I still play in bands. We’ve been on tour, and I was the one who booked the shows. I was the one who dealt with the business. It was something I wanted to do, so what did I do? I made it happen for us.

Josh Parkinson: That’s awesome.

Jonny Nastor: That’s kind of how entrepreneurship is, right?

Josh Parkinson: Respect. Yeah.

Jonny Nastor: I just want to know just one thing. I want to know if this is just me or if this happens to you, or has happened. You said you want to lead the charge. You want to be the visionary. You want to be independent and make a living in a world of independence and for yourself.

If this has ever happened to you, when was the last time you either woke up in the morning or went to bed at night or sometime through the day you were just like, “Oh, man. It would just be nice to just maybe not be responsible for all of this.”

Sometimes it’s just overwhelming and you almost think, “The other side of it is I could literally just show up for work either in a startup or a bigger business, but I wouldn’t have to deal with all of this.”

Choosing and Creating the Reality You Want to Live In

Josh Parkinson: I think that every single day, dude. That’s just part of the job as well. You always have this idea that there’s this other side of safety. It’s almost like this yin and the yang thing where, when you’re the yin, you got to have the yang next to you all the time. This might be going a little bit deeper, but I believe in life you should constantly have the idea of death with you all the time. It makes you appreciate life all that much more if you keep it close.

It’s the same thing with an entrepreneur. You got to keep the other side and have that thought of, “Man, I can just go get a job, and I could just walk out on this. I could take off some time for a year.” You always have those kinds of thoughts, every single day. Those are the default for me. Their always present. I know of them. They knock on the door in my brain every once in a while to let me know that they’re there. I never act on them. They’re just there as a foil almost to my reality.

Jonny Nastor: Beautifully said. When you’re starting, though, those thoughts seem more powerful, don’t they? It’s one of those things that when I realize, when I stop to think what the thought process of my day and the things that used to really sort of knock me off my game, that I would really put more thought into, now that’s just part of it.

You’re always going to be thinking those things, but it’s never to the point where I might actually go get a job. You know what I mean? At the beginning, when you’re struggling with stuff, you don’t have the experience of dealing with that mindset and that tension.

Josh Parkinson: As you get older, you realize that your thoughts about those idealistic item or lifestyles or whatever, the whole idea of Man, it would be so much easier if I just had a job that was secure.” That’s 10 percent of the reality, right? The reality is, if you had a job, that you just have security, that you would have 90 percent other attributes of your lifestyle that would suck, right?

As you get older, you realize that those idealistic thoughts, they contain a whole other side and that you’re not really considering the full picture. When I have those kind of thoughts, I realize that it’s really not that great to have a job, and that’s why I never had one.

Jonny Nastor: Nice. That’s 10 percent of the reality. I like that. Every blog post right now, every expert talks 80/20 rule — do 20 percent, get 80 percent of the results. Do what you’re good at. Delegate the rest. You’re good at not giving up. That’s your one thing. What is it, Josh, in business, within your business, can you tell me something that you are not good at?

When and How Josh Delegates Tasks to His Peers

Josh Parkinson: I’m not good at things that I don’t enjoy. One thing I’m not good at is operations. I’m not good at managing — get those results, and if you don’t, then I’m probably going to criticize you or come down on you. That’s not really a great way to manage I’ve found. You got to have a guy who’s good at operations and constantly there making sure that things are getting done, has processes in place to make sure that happens. That’s just something that I’m not good at because I don’t really enjoy it. That’s really why businesses break it down, right?

That’s why we have a CEO and a COO. A CEO is doing the kind of things that I like to do — leading the business, leading the vision. In SaaS products, leading the product because usually it’s the founder who has the vision for the product. At least it is in my case.

My main thing is I love building products, and I love building our product in particular. That’s what I want to spend my time doing. I don’t really want to get into whether my developers are spending their time properly, or whether my content team is being as efficient as possible, or whether all this other stuff. I’m very happy to outsource, not outsource it, but hand it over, delegate it to my COO.

Jonny Nastor: Excellent. How long into business was it that you still ran operations before you realized that you were not good at it and you had to get somebody else to do it?

Josh Parkinson: Like last month. I’m serious, man. It really was.

Jonny Nastor: That’s good.

Josh Parkinson: I just barely hired a COO, and he’s just a stallion. I worked with him for two years. We had a digital marketing agency that was really helping us, and this guy was the COO there. He was managing us as a client. He kind of eventually became our outsourced COO. Probably 12 months ago or 18 months ago, he started to fill that role. Just events, one thing led to another, and certain events happened to the point where we had the opportunity to hire him on as our COO. We just did that in the last month.

It wasn’t a huge transition since he was already doing so much, but now he’s doing so much more. I’m just like, “Oh, my God. Life is so much easier and so much more fun.” The funny thing is it’s not actually less busy. It’s actually more busy now. But I’m now concentrating on diving deeper into the things that I really want to be a part of. I’m so confident in the fact that these other things that have to get done in the business are getting done and getting done in a really effective and...