entrepreneur traits
Project Ignite Podcast by Derek Gehl Successful Entrepreneur Traits With Jon Nastor
00:00:00 00:00:00
  • Episode  36
  • Jon Nastor


Jon Nastor didn’t start out online. He opened a few of his own offline businesses, after finding his entrepreneurial edge at a young age. In 2011, he made the jump online and has since interviewed 207 entrepreneurs on his podcast, Hack the Entrepreneur. Jon has compiled all of the shared entrepreneur traits and strategies that he’s learned from so many successful entrepreneurs into a book, released in early December, that he shares knowledge from with us today.

Transcript: Successful Entrepreneur Traits With Jon Nastor

Welcome to the Project Ignite podcast–a podcast designed to skip the hype, skip the BS, and bring you real, actionable tips and strategies to help you grow your business and your income on the internet. If I’ve done my job, at the end of this podcast, you’ll have a list of actions, tasks, and steps that you can use to start making more money.Today we’re going to be diving deep into a topic I’m really passionate about after helping entrepreneurs over the past fifteen years or so now–and that is, what it takes to become a really successful entrepreneur. To help us along this path, we have a special guest that’s been starting and running businesses for the past thirteen years.

His entrepreneur journey began with multiple offline businesses, but in 2011, he discovered the internet, and I don’t think he’s looked back since. By 2012 he was running a software company from his laptop, living the internet lifestyle and travelling the world with his wife and daughter.

And playing drums in a punk rock band. We’ll have to unpack that one with him.

He’s also the host of a very popular podcast called Hack the Entrepreneur where he’s completed over 200 interview with entrepreneurs from all over the world, driving 1.3 million downloads. He’s also forged partnerships with Copy Blogger and Rain Maker FM.

The internet changed his and his family’s lives, and he can’t wait to help you start, build, and grow your own business.

Without further ado, I’d like to welcome serial entrepreneur and more importantly punk rock drummer Jon Nastor to the show today.

Jon, thanks for being here.
Thank you so much for having me.
Before we get started, could you expand on your journey from offline entrepreneur to running an online business? What was your path to this point, and how does punk rock drummer fit into all of that?

Punk rock drummer fits into it because the businesses that I’ve created give me time to pursue the things I love to do, which is play drums in punk rock bands. I actually play in two currently, now that I’m back in my home town for the next few months. It’s the freedom and the ability to work when and where I wanted.

I discovered the internet as a business thing, and I’ve said it before and I stand behind it still: I’ll never create another offline business in my life. The internet’s the place.

I hear that so often. Once people figure out how to set up an internet business and experience that freedom, it’s tough to go back. So give me your career path as an entrepreneur. You were offline, how did you wind up online?

Looking back it makes more sense than when I was going through it. The band thing started, I was in a band all through high school. We’d want bands to play in our city, and we wanted to play with them, but no one would book them. So we decided to, with a mentor of mine, start putting on our own shows. It was very much a DIY thing. Make some money, play with the bands we liked, and then we started travelling around the country playing shows. It was a great way to spend my later high school years.

It kind of spiralled from there. Then I started working at a record store, and that spiralled into talking to the owner, and then me considering whether or not maybe I should buy this place. That was always how it went with the few jobs I did have; within the first year of working there, it would be like, Jon, maybe you should take over this business. It was always something I was really meant to do.

At the time, I was just seeing all these random events that didn’t make sense. But in my mid to late twenties, I started businesses. I sold my last offline business, and we sold our house, and at that point I’d had my daughter that was just about two years old. I was thirty or so, and I wanted to do something bigger. I didn’t want to be spinning my wheels anymore. I didn’t want to have to constantly be out of the house working.

When I was at my last business, I was out of the house 12 hours per day, 6 days per week. I wanted to spend more time with my daughter, more time with my wife. That involved me figuring out how to do something else. I didn’t actually know about the internet as a business tool. In 2011 it was a tool, but it wasn’t for everyone.

But I got this spark. I talked to some people I went to university with, and they knew someone that had actually started his own business and was making a lot of money. A light went on. I started talking to people, and realized that I had to figure it out. So I had that pool of money from selling my house and business, and I decided that by the end of that money, I’d have a business online.

It didn’t quite work out that way, but that was my goal.

When you say it didn’t quite work out that way, what was your path? So you decided you wanted to do this, what were your first steps?

I bought a whole bunch of courses to learn how to do it, but as seems to be the case with most people I talk to now, I didn’t really implement the courses fully. I bought them, that’s the thing, right, but we don’t do anything with them, and then complain that it’s a scam. That’s not the case, though! There would be some that didn’t work, but most of them are the real deal.

But I just didn’t really do it. I’d do the 30 day challenge, from Ed Dale, the whole niche website thing. I started a few of those–what was the first one? This is embarrassing. It was like, RC cars, or something like that. But it was really cool. Build a website, write some articles, get into some affiliate programs which were really interesting. And then that’s where I went: affiliate marketing. Started making websites and binding affiliate deals. And it worked!

But that was like two years of doing nothing. I did need some time to get the momentum, but that was like two years of me just buggering around. And not fully going into it. I don’t know if it was the fear of failure or the fear of success. I had to get a job after those two years.

So a month or so into this job, I was like, this is ridiculous. I can’t be here. I have to do something. Then I really got into the pay per click stuff. I’d work all day, hang out with my daughter for a couple hours, and then at eight o’clock or so I would work until 3AM, every night, for seven months. I just focused and focused and focused.

At the end of seven months, I quit my job, and I haven’t looked back since.

There’s a few really valuable lessons there. A few of the things you said there really resonated with me. Because that’s something I see everywhere–investing in a dozen different courses and not really implementing anything. That is one of the biggest mistakes I see people making. But it’s tough! You subscribe to all of these lists, and I call it Shiny Object Syndrome, right, because something new comes along and you have to chase it.

That’s huge. So here’s a question for you. Your RC cars, you started in that niche, and it didn’t make much money. Did you learn from it, though?

I wouldn’t be here without that 30 day challenge. It’s the basis of everything: understanding a market, understanding how to write copy, figuring out WordPress. I can remember buying a domain, and hosting, and then seeing all this DNS stuff and being so confused. I think that’s the hardest part. Once you start doing it, there’s a transition that happened in my head. I look at websites now and know that some dude just decided to create that. There’s plugins involved, there’s hosting somewhere, the DNS thing… These sites are made by people like me. It was no longer a weird thing that I wasn’t a part of.

Before that 30 day challenge, the internet was a lot like television for me. Watching TV is so passive, and I don’t think to myself–I could just make a TV show and toss it upon NBC. Because I can’t do that. With the internet, it’s not like that. So I was finally brought into the club that was the internet.

That was life changing.

What you just said there is so crucial to new entrepreneurs. I just came back a month ago or so from events in Australia, and one of the messages I put out for people is that you need to just pick something and then get started. Even if you’re not super passionate or the idea isn’t perfect, just the process of learning and implementing and growing is going to open so many doors that will never open if you just sit and wait for a golden opportunity to pop up.

That’s huge. I really wanted to highlight that with you, because your story is so representative of how so many people get into this.

Let’s take a step forward. Over the past few years, through your podcast, you’ve interviewed how many people?

Jon: Like, 207, or something.

You’re ahead of me! I’ll have to catch up.

Are they primarily digital or from all walks of life?

They’re mostly digital. I’ve had a few old school entrepreneurs, like the founder of Ugg Boots, because it’s an awesome story, but I tend to focus on the digital because I love it.
This is why I’ve been looking forward to this conversation. I love thinking about what makes entrepreneurs tick. After interviewing 207 entrepreneurs, what are the common entrepreneur traits you’re seeing among the successful entrepreneurs?

Contrary to what I thought before I started talking to all of these smart people, it’s not a strategy or a tactic that can be taught. It’s all of their mindset around business and personal growth and life. They all share these commonalities. The people that just want to have their secure corporate job until they retire, they don’t share these traits. These are things that anyone can take on–and you should, even if you don’t want to be an entrepreneur. It will make your life so much better.

To boil it down to three of them, the first is absolute confidence in yourself. Everything you have within you, every skill and every weakness, is what will make you successful. These weaknesses and strengths among the people I’ve talked to vary so greatly that they’re almost irrelevant. You just have to nourish it and take it in. When you know those weaknesses, you can put people in place around you to improve on those weaknesses.

If you don’t admit that you have them, and don’t acknowledge what they are, they will hold you back forever. So you have to just have that belief in yourself. When you’re the kind of person that wants to sleep in until noon every day, do it, and do it confidently. Just because Richard Branson wakes up at 5AM every day, doesn’t mean you have to!

You can take things and try them, but when you really find that you’re exhausted until 8:30AM, sleep until then. Just own it. You don’t have to be other people. When you can confidently be yourself and push your strengths and weaknesses forward, you’ve won.

I agree 1000%. People operate differently. Perfect example is the Steve Jobs biography. I can’t tell you how many young entrepreneurs read that and said, yeah, I wanna be an asshole like Steve Jobs! And I’m thinking, no. Take what works for you. Don’t try to model everything because not everything works for everybody!

Let’s take a step into that confidence in yourself. The other side of that is the lack of confidence. I see this as one of the biggest roadblocks with people really igniting and taking that next step and investing themselves in something. That’s their fear of failure. I feel like that holds so many entrepreneurs back–whether it’s conscious or unconscious, there’s always this fear of “what if it doesn’t work?”

Where do you sit on that? You might’ve gone through that a bit on your own.

It won’t work. What’s the best way to create a business that will succeed? Create ten businesses because one will succeed. But if you make one site your be all end all–it’s like the first person you date. The first person you date is not typically the person you’ll marry. The first website you make will not be the one that succeeds.

It’s just not. But if you know that, and you go, well, I’m going to create a new site every two months for 20 months, that means by that time, you will have a successful business. You have to know and now put all of your hopes, dreams, and eggs, in that one idea. When that idea doesn’t work, and it won’t, it’ll crush you.

We’ve all been there, but we’ve pushed through until we got to the one that made it. And then yeah, when that one makes it, it’s easier to get to the next one. But that first one takes so much learning. I don’t mean let everything fail blindly, keep trying to learn from every business you start. And remember that it’s not you, it’s business. It’s not personal, it’s because it didn’t hit the market quite right.

Learn something from it, and move on. When you get to the tenth business and it doesn’t work, email me. We’ll start the eleventh one and it will work. It’s a numbers game at that point.

I can’t remember who said it, maybe it was Edison or Einstein, that said, “I’ve never failed, I’ve just found 10,000 ways that don’t work.”

The message that I’m hearing from you, which I stand behind 1000%, if you want to get to that winning business, it’s a process. You need to create your RC car website. You need to go through 20 relationships before you find the person you marry.

When you say it’s mindset, you’re so right. It’s about shifting people away from that idea of “I need an instant win.” It’s all a process. It’s okay if not everything works, because that’s all in the process of getting there.

So, diving into mindset, we talked about confidence on yourself, what’s next on the list?

You actually touched on it–learning to be wrong. Taking ten steps, and learning from each one.

Making sure to not internalize it and taking it personally. You’re not a failure, the business failed, and businesses fail all the time.

As an entrepreneur, you’re not a failure. You’ve actually learned and moved on to the next bigger and better project. Then, you create your own luck.

People on the outside look at us and think, Jon is so lucky. He gets to travel all over the world and live wherever he wants. These are the same people that when I was working hard late into the night would ask me out for a beer, and I’d say, no, I have to keep working. And they’d say, oh, are you making any money yet? No? That’s a waste of time, you shouldn’t do that.

Now they say, you’re so lucky! But that’s not true, it’s not luck. I created this luck. And you can do it to. I’m not better or faster or smarter than any of you. I just put my head down and I did the work and I worked until it succeeded. Then when I succeed, I go on an awesome trip and I enjoy it.

I’m throwing quotes out left and right here, which is weird because I’m not usually a huge quotes guy, but:

Being an entrepreneur is living your life today like others won’t, so you can live your life tomorrow like others can’t.

It’s frustrating as an entrepreneur when you get to that level of success and people are still calling you lucky. They don’t know about the sacrifices you have to make to get there. But in the greater scheme of things, sacrificing your free time for a few years for this kind of freedom is completely worth it.

Ultimately, I will admit a little bit of luck, because if I had been born ten years earlier, the internet wouldn’t have existed like it did, and I would’ve been screwed. But that luck exists amongst everyone listening to this podcast, because this technology did not exist ten years ago. So the world has given me that much luck.
I totally agree. Had the internet not existed, I think I’m unemployable. I’d be so screwed.
I say that all the time, sitting around the kitchen table. This family would be so messed up. What would I be doing if there was no internet?

Everyone that knows me knows that I barely scraped out of high school. Barely. I was not going to university. Had I not found the internet, I’d be nowhere. I met my wife when I hired her to be my VP of Finance. The whole thing is thanks to the internet!

Let’s take a look back now at your entrepreneurial journey. If you could do things differently, is there anything you’d change?

The one regret that I have is that I wish I had started those ten businesses sooner. In those first two years, I could’ve started those ten businesses–anyone could’ve. I would’ve succeeded far before, and I wouldn’t have had to get a crappy job that almost killed me, and I would’ve made it to this point three or four years earlier.

It’s not that it’s easy, but it’s a manageable thing to start setting up those businesses when the first ones don’t work. Then it’s like, what’s that? A Paypal payment… Someone I don’t know just sent me money. And your brain never goes back at that point.So if I could’ve been there sooner, my life would’ve been so much better earlier. I don’t really look back and regret it, but I could’ve just put in the work earlier and known that I had it in me. I wish I’d known to ignore all of the hype-y, fluffy, shiny objects. When people interview Gary Vaynerchuk, and ask how he got started, he doesn’t say “well I figured out how to get 3 million free visitors to my webpage and it changed my life.” It’s never that. It has never been that. That’s what it is on a sales page, but it isn’t real.No one has figured out a tactic to use Facebook to drive ten million likes and have their life changed. It’s not tactic based, it’s about the mindset. And I wish I had realized that sooner.

That is such a powerful message. For the listeners out there, Jon is saying to start ten businesses in the next two years. And if you’re just getting started online, you’re probably thinking, what? How am I going to start ten businesses in two years? But that’s the beauty of the internet. Once you understand the process, you can get things off the ground so much faster.

I’ve always lived by the test small, test fast, fail small. You can do that so quickly with the internet. Obviously the first time you’re doing it the learning curve is steeper and it takes longer, but once you’ve got that first website under your belt…

If you had an idea Jon, to put up a website today along with sales pages and a shopping cart, emails, stuff like that–foundational. How long would it take?

I’d give myself seven days.
Seven days! And how much do you think it’d cost?
Maybe $100. Because I already have my hosting. Once you get your hosting, that initial investment, but after that, you’re totally set. I have my emails already set up so I can just add a new email, but that’s it. Maybe I want a new WordPress theme, but I can just hire someone on Fiverr… Literally, a hundred dollars, 7 days, we’re done.
The barrier to entry isn’t high. For everyone listening but thinking, “I want to start but I don’t have any ideas!” What’s your advice to those people?

The best way I’ve found to find ideas is to spend the next few hours online, as you’re doing the things that you do, look for failures in what you’re doing. Something cumbersome or annoying. Like with Buffer App, the idea was that I want to send stuff to Twitter, but I don’t want to have to be on Twitter all the time. I wonder if you can just schedule it, or why Twitter doesn’t have that.

Buffer is doing like $600,000 per month now, just based on that you can put something in the app and it will send it to Twitter for you.

The simplest things. Velocity Page, my newest business–was literally me trying to set up a landing page before I had to go to a conference. But I couldn’t do it very quickly. So I went and bought the two things on the market that existed then, and they both sucked, so I decided to build my own when I got home.

These are literally just scratching your own itch. It’s really easy to write copy as well, because you know the pain point well. Like with Gmail, there’s add-ons like Boomerang or Sidekick that you could get coded on Odesk, and people will pay $5 or $10 or $20 per month to use them. There’s all kinds of stuff out there that you can improve.

This goes back to understanding that the internet is just websites built by other people. That’s it. That’s why it’s there. So you need to change your mindset from being a consumer to a producer. I didn’t even know I needed Boomerang til it came out, and then it was like, how much money can I give you? That’s amazing. And it’s the simplest thing.

All Boomerang does is take an email out of my inbox and send it back to me at a time that I specify. It probably took five hours to code. And I think they charge $10 per month, but they have thousands of users.

If you have an idea like that, Google it. See what comes up. If you type in your idea and see that there’s already Boomerang and Sidekick, don’t think that you can’t enter that market. That’s why you should enter this market–because there are people in there that are making good money. All you need is a small portion of those users.

You don’t need to create Facebook. You can make a ton of money with the littlest ideas because there are so many people that will want to use it. You only need a fraction of the people on the internet to pay you $5 per month to be ultra successful.

Start small. Google the idea. If the idea exists and has customers, run with it. You can duplicate it exactly, but if you improve it a bit you’ll get a bigger market share. With Boomerang, even if there’s something about the branding that doesn’t quite sit right, and someone else created the exact same program but branded it differently and called it Bounce Back, you’d get just as many customers.

They make a lot of money every month.

That’s huge. That’s a shift in how many people starting up think. When you look in a market and see a bit of competition, that’s a great sign because people are making money. People come to me and say, I have this amazing idea! I ask what the competition is like, and they say, there is none! That’s not really a good sign, because that means there’s probably no market.

Some competition is fantastic.

Another thing I want to highlight: solve small problems. When you’re getting started, it could be a tiny thing. I see so many people start out and try to create the Cadillac of a solution, trying to rival Hootsuite or Buffer, and I just think, no. Unless you have deep pockets to develop something that big, start small!

That was really sage, valuable wisdom.

I just actually wrote on my notes, called Bounce Back, like I just said, the Boomerang copy, and I think I might actually run with it. Give me seven days.

Here’s one of the things I’ve found, too, in the world of software. There’s a ton of software with good intentions but they’re designed by pure developers. With a little polish on the UI, and a little marketing acumen, you can blow it up. So, again, there’s so many little opportunities where people have created great things but they don’t know how to sell it.

So if you can market that better and make it look nicer, you will crush it.

So in 14 days, you’ll be live with Bounce Back.

I hope so, but I’m also launching a book in 14 days. If I had nothing else to do, I’d run with it. I may still. Unless someone out there wants it–if you beat me to that domain, it’s all yours.

I totally hold no grudges. Take it, run.

I have one last question for you. I see this hold so many people back. So people say to me, I’ve found this great niche, but there’s a problem. I say, what’s that? And they say, well, I’m not an expert. I don’t have expertise in that field.

And then I say, what the hell is an expert anyways? No one can give me a straight answer.

So if you don’t have that expertise, how do you become an expert?

That’s awesome. So Tony Robbins, this is the Tony Robbins method. This is how he started many years ago. So the first step is you know nothing about the field. Then, you find five people that are experts in that field, and you interview them. Then, you boil it down to the simplest things that they have in common with each other, and then you do those simple things over and over and over again.

It’s a 5 point plan. You can Google it. I was thinking, that’s brilliant. By the time I interview 100 entrepreneurs, I’ll be an expert in this field. I got to around 50, and I started seeing these common themes running through. I was thinking, oh my god, you’re all geniuses! And nobody knows because they’re all working in their own worlds. Then I categorized it all and broke it all down and realized I had to write a book on this. They weren’t experts until they talked to experts in their own fields and learned.

Nobody is born an entrepreneur. It’s something you have to step up and do. You just have to know that. It goes back to having self confidence. You can see someone up on stage and wish that you could have that kind of presence, but if you talk to them about their first few times presenting, they’d probably tell you that they were throwing up backstage.
entrepreneur traits
They didn’t start a massive business from the start. It may look like that from the start, but we all have the same fears and doubts. And then someone younger will come up and ask to interview you, because they want to be an expert, and you’re one of the experts they want to talk to.

And this is one of the greatest startup strategies in so many fields. I think one of the best ways to do this, to build a website and a following where you don’t have any expertise, take Jon’s strategy and start a podcast. Start interviewing people and connecting with people! Utilizing their knowledge for yourself, but also create some really great content.

In our space, it’s pretty competitive. But when you drill down into certain niches, there’s huge followings but there’s zero podcasts happening. It’s so easy to go out and collect experts and create great content while leveraging other people’s expertise.

The more I talk about it, there’s so many opportunities out there.

There is! This goes back to just getting started. With my podcast, I had never interviewed anyone in my entire life. I decided one weekend after thinking about it for a few months, that I was just going to do it. I started it up on a Sunday, and by the following Thursday, I was interviewing my first two people. I had never interviewed anyone in my entire life.

The momentum of now interviewing 207 people in the last 15 months, getting all of these downloads, I’m considered an expert by many people in the industry. It’s at the point now where every two weeks or so, I get a really great business opportunity in my inbox. A coder, or someone, has a great idea, and they say, let’s use your audience, you can do the marketing.

And I say, ah, I don’t have the time, I can’t do it, but holy smokes. I had seriously never interviewed anyone before. But that momentum started more momentum around me where people started hearing about me and then started wanting to partner with me… It’s crazy. It’s all because I’m talking to experts. It’s amazing.

And don’t say, you’re a natural interviewer Jon, because 15 months ago, I had never interviewed anybody and I was so nervous. I was sweating and shaking beforehand. I just did it.

But also, don’t go listen to those first few interviews.

I’m so glad you’ve said that. I’ve been lecturing my members, start a podcast! And everyone says, but I don’t know how! I’ve never interviewed anybody!

Just wing it! Just do it! Ask him some questions! Jon, you’re living proof of that. You’ve built your expertise by interviewing those 207 people. You’re on my podcast now, because you’re an expert!

And somewhere along the way, I partnered with Copy Blogger and designed a podcast course for them. They have millions of users. It makes no sense! When the CEO asked me, it was right after I’d interviewed him and he started asking me all of these questions.

I was sitting there like, 7 months ago I had never interviewed anybody before, but why not, I can design a course! Sure! I know how to podcast now. I’m an expert. I’m at podcast 60 something.

And now I’ve taught over 400 people how to podcast.

That’s amazing. Just take action. I love hearing stories like yours. I love your attitude. Just get out there and do it. Don’t overthink it.

Before we wrap things up, if our listeners want to find out more about you or your podcast or your software, where can they find you?

The best place it HTEBook.com. I have a book out early December. I’ve distilled all of those interviews into 50 hacks, and I’ve wrapped them in lessons and essays. We start with the mindset, and how to deal with being wrong, and then the last part is scaling up your business.

It’s only $3 or $4. If you want to know about me, that’s the best place. Also, HacktheEntrepreneur.com is the podcast. You can also get access to me when you buy the book, and can send me all of your questions and ideas and I’ll give you my best feelings and thoughts. That’s what I’m here for.

Jon, thank you so much for sharing your story and everything you’ve learned interviewing so many flippin’ entrepreneurs and giving us so many valuable tips and strategies on what it takes to become a successful entrepreneur and the entrepreneur traits people need to learn.
Thank you so much for having me, it was my pleasure.

Awesome. Well everyone, that was Jon Nastor. Everything we talked about will be included in our show notes along with our transcription of this episode–that’s up on ProjectIgnite.com/podcast. If you haven’t done so already, you can subscribe on iTunes–just look up Project Ignite, Derek Gehl, or Internet Marketing and I’ll show up! If you’re an Android user, just get us on Soundcloud!

Also, if you like what you hear–leave a review, tell us what you think. I love to hear what you think. Your feedback is what gives me the momentum and motivation to keep creating this podcast for you.

Now it’s time to take the tips, tools, and strategies that we’ve learned from Jon here today, and apply the final essential ingredient to make this all work for you: that ingredient is action. Go forth, take action, and stay tuned for more info-packed episodes of the Project Ignite podcast–a podcast designed to make this whole internet business thing easier so you can make more money and have more freedom.

This is Derek Gehl, signing off.

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  1. Great Interview Derek! Jon interviewed me a while ago and the success of his show is largely due to the fact he is a great interviewer and knows how to bring out best in his guests. I’d say he possesses one trait of being a successful entrepreneur, and that’s the absence of the “me syndrome”! You just gotta keep it real 🙂 Thanks again – Belinda

  2. Hey Derek,

    Great podcast! Jon’s an awesome guest to have on the show too! I really enjoyed hearing about his entrepreneurial story. It’s amazing to hear how he started off in 2011 but then had that random couple of years only to really knuckle down and crack online business seriously a couple of years later. Really inspiring story with loads of great tips for entrepreneurs – thanks for sharing!

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