The Journey From Travelling Poet to Online Entrepreneur

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 organized way. It’s awesome, man.

I can’t recommend a COO enough for a founder, a founding team. In our business, in the SaaS business, you always got to have a CTO. You got to have a technical guy. You got to have a business guy. I think it’s very rare that you get a business founder who’s good at and loves both the executive side and the operations side. I tend to think that most founders are more executive. The faster you can find some help with operations, I’m betting that your business will thrive because of it.

Jonny Nastor: Yeah. I appreciate you being honest and telling us it’s only been a month. It sounded like such a revelation that you had so long ago. That’s good. I like that. It’s all a process. It’s fluid. These businesses just kind of grow and come at us. We don’t have always time to figure out the right way to do stuff until we do it and it works. Like hiring a COO a month ago, now you’re like, “Yeah, of course, operations. That’s what it needed.”

Josh Parkinson: Yeah. That’s part of the whole entrepreneurial lifestyle, too, is that you never can plan too far ahead, and you’re comfortable with this. I wanted to talk about this before. That’s the thing is that a lot of people would really feel uncomfortable with my life or your life because they really don’t know what’s going to happen in a couple months.

I don’t know that Facebook’s not going to shut down my app in a couple months. I don’t know if Twitter’s going to remove their API from us. I don’t know that one of my competitors in going to crush me in a couple months. I can’t predict it. It’s possible, but that’s the reality that I want to live in, at least I choose to live in. That’s just what comes with the game, right?

It adds to the whole fun of it. I recognize that it’s the default for me now, but for most people, it’s kind of scary to not know that and not have that security.

Jonny Nastor: Yeah. It’s a good clarification. To take it even a step further, I almost feel like it’s more secure. Like you said, we’re in control. I don’t think I could sleep at night if I worked for a giant corporation that I’m worried every Friday when I go to work that there might be pink slips handed out because there’s a thousand people being laid off, and I’m just one of them. That’s, to me, not having control. That’s not any way being in control of my destiny. That freaks me out way more than just not knowing what my business is going to be doing next month.

Josh Parkinson: Maybe so. I think maybe you’re overestimating the risk that those people face. I think it’s actually much more secure than that, but I get your point.

Jonny Nastor: That’s true, man. I’m not part of it either, so I don’t know. I read about it in magazines and newspapers. I don’t know. Alright, Josh, let’s move to what I call projects. Projects probably is going to be some feature or something within Post Planner, your business, at this point.

You mentioned earlier it was strictly about Facebook for you guys, then Twitter. Then you mentioned Instagram. Within your business structure as it stands now, how do you decide when a new project –whether that’s a new feature or taking on a new social platform — is something that is right for your business to do?

Articulation — Why It’s Very Important to Josh Growing His Business

Josh Parkinson: That’s such a timely question. It’s probably something that all SaaS businesses are facing. It’s this choice of product development, which features you’re going to bring on, which ones you’re going to start development on, how quickly you’re going to push them out. It should be, in my opinion, a constant battle inside the company between different sides. You should have really nice checks and balances inside your company.

For example, my CTO is very much the guy who’s saying, “We need to remove features. Stop adding features. We need to test. We need to get more data on what our users are using, cut things down, and make things more simple.” He’s always constantly pushing back on me, where I’m the guy who’s like, “We got to add this. What if the app did this, too?” There’s this kind of balance and this constant conversation happening — if you have multiple voices coming in on that, it becomes a very rich and important discussion.

It almost becomes the most important discussion in the business about, “Why are we doing this? Why are we going to add this?” What we’ve done recently — I’ll just give you some real tactical stuff that was spearheaded really by this new COO, this guy named Sam — we’d put together a Google Doc sheet where we listed all the features that we have. We use JIRA for our management of the product and bugs and all that. We have a ton of issues in JIRA that are new features and new ideas for things we can add.

We looked through those, and we found all the ones that are most viable and seem to be the most popular and the ones people are passionate about. We listed them in a column in this Google Doc. Then we added three factors — 1) the customer value, the value of the feature to the customer, 2) the business value, the value to the feature to the business, and then 3) ease, how easy is it to actually create it, be able to implement it and add it.

Then we polled people in the company and let them vote. We just said, “On a scale of 1 to 5, give me your idea about how valuable this feature would be to the customer, to the business, and how easy it would be. Obviously, the ease part, we favored the development team, especially the CTO and his opinion on about how easy it would be.

We just all voted. We all went in there, and we put in our numbers. Then we calculated the average of them in this total. Then we saw immediately all these certain features were rising up at the top and certain features rolled down at the bottom. Now we can have a real discussion about which ones seem to be important to the team. Also, it’s on certain people who are for features to convince the rest of the team.

When my COO first said that to me, I was like, “Why do I have to convince my team of this? I’m the CEO. What I say goes, right?” But he’s like, “No, dude, that’s actually counter-productive” — for obvious reasons, but the most important reason is that, in the act of explaining and making the case for your features that you want, that process of doing that, you’re going to think it through and probably improve the idea of the feature and realize things along the way.

Maybe you might think, “Oh, wow, now that I actually have to explain this, now I’m starting to see that it’s going to be a lot more complicated. It might not be that valuable to the customer, blah, blah, blah.” In the process of doing it, making my case to my fellow team members, I’ve fleshed out the feature more. I explain to everybody more.

This process has really been pretty cool in our organization. We just had a meeting a couple days ago where we all got on and looked at the results. We were all like, “Wow. This is interesting.” People were making arguments with some features, others for others. This is just internally, so now we have this idea about where we are aligned internally on all these features. We call it our ‘features score card.’ We see these five to 10 features at the top that have the most votes.

Now the next part of the process is to go to customers and have a strategy for presenting it to some power users and customers in the segment that’s making us the most money, the ones that we want to pursue and see what they think about it. Not so much for them to validate or say ‘yes’ or ‘no’ about it. Again, similarly to what I said before, it’s more about maybe they have ideas on how the feature would actually be implemented and other ideas about certain parts of the feature, et cetera.

That’s the process that we’re using right now. We validate it internally with a feature score card, vote on it democratically, and then we go out and go to the customer, see what they think. Then once that’s done, we move on. We just green light features and send them to design and dev.

Jonny Nastor: You said something interesting. You do it democratically, but you were like, “No, man. I’m the CEO. I can decide what happens.” And your COO is like, “No, no, you can’t do that.” I’m going to back to your gut. To me, that’s what tells us these things.

Is there anything in your gut that says, “No, I am the CEO. I make these decisions still. I want to hear everybody’s opinions, and I want to … “? When it comes down to it, if shit goes completely wrong, it’s not anybody who voted’s problem, it’s yours. You own the company. You know what I mean?

Josh Parkinson: Yeah, for sure. In my gut, I know that I’m in control, but I know that if I can’t even explain the value of this feature to my team and convince them, then I need to think twice about it.

Jonny Nastor: That’s true.

Josh Parkinson: I’m a well-spoken, persuasive dude. If I can’t even articulate the value of a feature in such a way that my team doesn’t buy it — the guys who actually believe in me enough to work for me — if I can’t even do that, then what makes me think that I’m going to get customers to use it?

Now the other side of that is maybe you have the vision and you can’t quite articulate exactly the full, long-term vision of where this goes. I think about that on certain features. In general, I think the exercise of having to articulate, the bottleneck of ideas is articulation. If you can’t articulate your ideas, then they’re really not ideas yet.

It’s the same thing for these feature ideas. If I cannot articulate the value and how it will work, show it to you, and make it obvious and you are the guy who actually believes in me enough to work for me, then there’s a problem with the feature. I need to either think it through and explain it better, or move on to another feature.

Jonny Nastor: Well said, man. Very well said. I like that. Alright. We’re going to end off on something I’m calling the ‘entrepreneurial gap.’ You’ve done some cool stuff. You’ve built a really, really impressive business, but there’s something that I see amongst entrepreneurs.

We’re always looking forward — one month, three months, six months, a year, five years into the future. Everything will be better when my business is there doing that, when it’s that, when I get to do this, when this happens, right? Always in the future.

Even before we hit those goals in one month, three months, five years, before we even hit them, we set five loftier goals further into the future. We’re always looking forward. We never seem to stop and look back at the stuff we’ve come through, the stuff we’ve accomplished, to be amazed at where we’ve come over the last few years.

So, Josh, I would love if you would just stop right now, turn around where you’ve come from and to what you’ve built, and tell me if you are happy with that. Tell me if you are proud of what you’ve done. Of course, you still want to look forward. You still want to have goals, of course. Can you just tell me your experience of stopping and looking back at where you’ve come from?

Perspective and Gratitude: Josh on What He Appreciates the Most

Josh Parkinson: Sure. It’s a great question. It’s something I think people should do in general. Even non-entrepreneurs, they should stop and look and get perspective, and show some gratitude to their past actions and what brought them here.

For me, the first thing I really think about is the money and the security that, that brings. I have a family, two young kids and a wife, and for me, when I look back and I realize that, “Damn, dude. You built a living for yourself.” I built a salary for myself that I probably couldn’t go out and get. Maybe I could, but it would be a pain in the ass for me to go out an interview at a bunch of jobs and get a job where I make as much money as I do now.

When I stop and look back and realize I’ve actually built this for myself out of nothing, out of thin air. I’ve built this living for myself, that’s what I’m most proud of. It’s the perspective. I was a poor musician in Europe. I was happy on a day when we made 200 Euros for a gig. That was a big gig for us. That was 50 Euros for me because we were a foursome. Living at that meager lifestyle for so long, it was the same thing.

I got that money out of thin air. I built that living for myself and those experiences for myself as well. Just the contrast of that compared to having a family in one of the most expensive cities in the world, a nice place to live, my kid’s going to private school this next fall. We pretty much get to go and do whatever we want. We don’t really have to think about money that much. My wife, she has a great job, so that contributes of course. When I stop and I think, I look back on what I built.

Maybe that’s a selfish perspective, but that’s really a human thing. I first think about my family and our security. I’m proud of the fact that I’ve built a lifestyle where I can have security for my family and also, at the same time, be doing something I love and be making good money at it.

Jonny Nastor: Beautiful answer, man. Beautiful answer. And you should be proud.

Josh Parkinson: Thanks, dude.

Jonny Nastor: You’ve built something really, really impressive. Josh, in passing we got to mention your business. Can you specifically tell the listener where to find out more about you and your business?

Josh Parkinson: It’s PostPlanner.com. @postplanner on Twitter. If you guys are having trouble with your social media, if your social media accounts are crickets and graveyards — you’re just not getting any engagement. You don’t know what to post. No one’s clicking on your post. You’re not getting any traffic from social — we can help you. We’ll help you triple your engagement in about 10 minutes a day, send more traffic to your website, and give you more customers from social. PostPlanner.com, come on over.

Jonny Nastor: Excellent. They can find you, Josh, on Twitter as well?

Josh Parkinson: You can find me at Twitter. It’s @Yessayer. That’s where I am.

Jonny Nastor: Excellent. I will link to PostPlanner.com and on Twitter, and I will link directly to you, Josh, on Twitter in the show notes for everyone, so they can find you and continue this conversation with you.

Josh, thank you so much for your time. Please keep doing what you’re doing, man, because it’s really, really awesome to watch.

Josh Parkinson: Man, this was so much fun, Jon. I really appreciate you having me out.

Jonny Nastor: My pleasure.

Josh, thank you so much for the conversation. As was probably obvious, I just had so much fun on this call. It was a lot of fun. I do thank you for the smart conversation. It was just good. I’m speechless. Sorry. I don’t get speechless very often.

So Josh said a lot of smart things. I have this list. I have six smart things that I’ve written down on this sheet of paper. It’s a tough choice, but when I really, really think about it, there was one thing he said. One thing that really stuck out, wasn’t there? Did you get it? Did you hear it? Let’s do it. Let’s find the hack.

Josh Parkinson: 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.

Jonny Nastor: And that’s the hack.

Josh. Yes. Yes. Yes. You’re right. It might be going a little deep, but how could I miss it. That’s brilliant. The idea of keeping the idea of death close to you and making you appreciate it. To me, this is probably the ultimate reason why I do the things I do in business and in just creating things. I do appreciate the fact that we have a finite amount of time here on this planet, and I’m not going to waste it just trying to do stuff that don’t really matter or that I’m going to get to the end of it and be like, “Oh, I wonder what I could have achieved.”

I’m going to go and try everything I possibly can and go for it. To me, the ultimate sort of end or cost that I would pay is not trying things and not being willing to put myself out there and do possibly big, cool things because I was scared to try. You got one shot, let’s do it, right?

Josh, I appreciate you taking us there because I think sometimes we get caught up in the business side of it, but there’s this whole big grand life sort of thing, too. What it is we do and the reasons behind why we do these crazy things that we do in business is because I think some of us, really, we know that there’s this definite time we have, so let’s just make the most of it.

I don’t want to just waste time playing video games all the time and watching television. I want to do cool stuff, and we have to have that inner sort of passion for it to do that. Thanks, Josh. That was good. I really, really, really appreciate you bringing that up.

Again, thank you so much for taking the time. It’s always, always, always a pleasure when we get to spend this time together. HacktheEntrepreneur.com is the website. You will see Josh on there when this goes live and anything we’ve mentioned or talked about. Go, check it out, and it’ll be great.

Also, you can get on my email list there. Every Sunday, my best writing, best work, it’s going in there. You can get it direct, and that’s also direct access to me. Hit reply to any of those emails, come straight to my phone, straight to my laptop. Let’s have a conversation. I’d love to talk to you.

Again, so much fun. I appreciate it so much. Please, until next time, keep hacking the entrepreneur.