digital telepathy

Chuck Longanecker is the founder of Digital Telepathy a design company that has created some ground breaking sites. They are responsible for the design of Tim Ferris's 4 Hour Body, Neil Patel's Crazy Egg, New Relic and more. The inspiration and idea for this company actually arose from a job loss and a general lack of fulfilment in the typical mundane day-to-day jobs. Chuck had a vision that was far greater and far more powerful. He wanted to inspire change, to help people, to make a difference by creating designs that simply make things better. He called it Betterment.


Our goal is to be Officers of Betterment
Our experiences are what binds us together
It's repetitive motion every day that builds a company
If you make a few things better everyday, you eventually get exponential results

Today's Podcast Highlights

[5.54 - As we became more savvy, we realized we couldn't become phenomenal at any of these things as long as we kept doing them all.]
[6.41 - We wanted to create something new and put it out there, something that hadn't existed before instead of creating more of the same.]
[7.04 - We had all our own ideas in-house and we decided to create a budget of time to start building stuff.]
[7.51 - We just hit the ground running and helped determine and iterate what the product actually is for clients.]
[9.37 - We have to test, we have to learn, we have to communicate with potential clients or customers or users, do that customer development, create the prototypes, iterate the prototypes until we actually see some growth and then we can go full bore into what the product's going to be.]
[10.8 - There's uncertainty everywhere. We kind of embraced that.]
[11.32 -  We wanted to build something so simple because it's so hard to make things simple and so easy to make them complex.]
[14.19 -  If you make a few things better everyday, you eventually get exponential results.]
[16.28 -  Our goal is to be Officers of Betterment, creating betterment, no matter what we do.]
[16.52 -  Our experiences are what bind us together, and kind of create what I call this experience DNA.]
[19.34 - Look inward, look at what you love to do, look at what you're passionate about and where you want to make a difference.]
[20.00 - Look out where the friction is, where is there something that you can solve, where is there something you can make better.]
[20.35 - Executing that vision and actually culminating it to a complete vision takes a long time.]
[21.20 - You want to affect a large group of people or else there's not a good chance of success.]
[21.29 -  It's repetitive motion every day that builds a company, and so you have to be comfortable doing the same thing everyday.]
[22.40 - When we blog, we try to share what we've learned with all of our readers of how to do things better. We share our process, we share our culture, we share how to design, we share all these things so that they could take it on their own and make things better. ]
[23.31 - The thought process is if we help people make their users happy, the users are going to take care of those websites.]
[31.55 - As you get older, I think your priorities change a little bit as they should.]
[33.11 - It's not a matter of how long you work, it's a matter of where your headspace is at, how well you work together as a team.]
[34.57 - It's interesting to be motivated by your mind and the family as opposed to other things.]
[35.15 -  To make a greater impact, you've got to do pretty big things.]
[37.53 - Make sure it is something you're passionate about or a problem that you want to fix as opposed to just a market opportunity.]
[38.05 - if you have an opportunity to work with someone you trust, I think that's pretty great.]
[38.32 - When you're alone as an entrepreneur, it's tough, right, because people will not understand what it's like to be you within the organization.]
[38.51 -  If you can be different, be technical and creative or vision and marketing or operationally sound or something like that.]
[39.11 - If you have a great team, that great team can come up with a great idea.]

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Full Transcript

Paul Clifford: Hi there software entrepreneurs and welcome to the show. Now today I've got an amazing interview with a guy called Chuck Longaneckerer, and Chuck is the founder of a company called Digital Telepathy. Now for many of you who may not know who that is, or what that is. Essentially this company is behind some of the most ground breaking sites and personalities on the web today.

For example, Tim Ferris's site, Neil Patel's sites, New Relic, a lot of tech startup sites, they all go to this company to talk about design. The reason is the design and user experience is really, really at the core, everyone who works for this company. Chuck's done an amazing job of getting everyone involved in the ethos of purist design and we've got some great insights to share on the show.

Instead of doing the show as a normal podcast from base camp. What we decided to do, in fact I jumped in the car and went down to his office to meet and greet some of this team in person. Let's get on with the show, let's meet Chuck obviously some background noise because this is a live interview but I really think you're going to get huge amounts out of it. Chuck welcome to the show, thanks for coming on board, I really, really appreciate you spending some time with us today.

Chuck Longanecker:  Good to be here.

Paul Clifford: You know we're in your fantastic office, I can see some really amazing talent around. You've got what I can sense is like a real great culture of people like really fascinating interested in design and in their work. Tell me a bit about yourself when did you actually start, what got you into building this amazing company.

Chuck Longanecker: Yes, love to tell you a little bit more about that. So I started DT a good 13 years ago when I was 25, which is if you do the math, you know how old I am now. I started kind of on a whim. I got laid off from a startup in 2000, that I was working at, and I had a little tiny severance I think I had a $5,000 severance and I said "I'm going to see how long I can stretch this, and live on this and what the hell, I'll start a company."

Kind of work on my own because I wasn't really fulfilled working for other people. Somehow I'm still here. It was a really, really long road but I think I was born out of my lack of fulfillment with the jobs I was currently doing or I was doing in the past. Which kind of stemmed from you go in, you do your work, you go home you're not satisfied about what you're doing.

You don't get to kind of see the fruits of your labor, you write a white paper, and someone reads it, maybe they make a decision on it. When the web started to increase some popularity, we got to make something and it was put on an IP address that anybody in the world could see. Even if you weren't successful for those sites, you could actually have other people see the fruits of your labor which was really fulfilling.

Luckily the web actually took off. At first I was convincing people that they needed websites, which is kind of funny to think about now and going to the local lead generation events, and you know just like sweating it. Eventually everything kind of picked up, and luckily we embraced design as what our core competency is and how to use design to create amazing experiences and grow businesses, specifically startups.

Luckily, everything that we've kind of followed our heart and started doing, started supporting us back with what the demands are, and now design is one of the most sought after elements of a service that we can provide. I think we got lucky, I couldn't be happier with how things happened.

Paul Clifford:  I remember those days when the web really, in its infancy ... I got involved in creating some sites as well and you would show those to clients and all that, and they'd be going, "Yeah but so what? How's that going to benefit me? How is that going to generate leads?" All those early conversations where you really had to sell the whole concept of having a website to these companies. Of course, obviously that really, really took off.

Chuck Longanecker: Yeah we used to have to fight for the budget from the white pages or the yellow pages. What a ridiculous idea now but at that time, we'd have some very progressive clients that are like I'm going to take a month off from the yellow pages and put it into this site and see if it can do more. Luckily, we were able to pull that off.

Paul Clifford: Often, you were actually selling to not even the marketing department, it was still within IT.

Chuck Longanecker: Yeah.

Paul Clifford: Amazing days, amazing days. But obviously, you started doing that and where did you go on from there?

Chuck Longanecker: From there, we started to learn that what our sweet spot was. We started off giving all kinds of different services, from hosting to email marketing to SEO, and right when the social media came out, we jumped on that. Anything that someone would pay us for, we would do for them, we'd figure it out.

As we became more savvy, we realized we couldn't become phenomenal at any of these things as long as we kept doing them all. So we focused in on design and specifically user experience and user interface and then we looked to see where...who had the greatest needs for this, right?

The emerging startups that were building these products, inventing new technology had the greatest needs for these as well. They were also the ones that were willing to be the riskiest. We like to be on the cutting edge of design.

As we worked with bigger brands, they were more conservative. As we worked with startups, they were just willing to go for it. We're driven as designers by the work that we do and how exciting it is, not how big the budget is per say, and also how many people we're potentially impacting and how we're impacting them. We want to create something new and put it out there that hasn't existed before. Invent something more so than just create more the same.

That led us to specifically user interface, user experience for startups. As we got into that, it was so exciting,  we got to meet all these entrepreneurs that had all these great ideas and we're satisfying their visions. We're like, "Hey, we want a little piece of that, too." We had all our own ideas in-house and we decided to create a budget of time to start building stuff. That was probably one of the best things we had done. It allowed us to go from what would be a kind of traditional interactive agency or company into a real product company.

We experienced all the pain and agony of figuring out what the product is, of getting it to scale, bringing on users, monetizing then eventually going through acquisition. That allowed us to kind of go to the phase that we are at now which is we have a very startup centric service offering we provide that is very agile that kind of works based on objectives, not on tasks, on what we're accomplishing so we don't take a scope, we don't go through a normal technical spec. We just hit the ground running and help determine and iterate what the product actually is for our clients.

Paul Clifford: Which of course ... and your clients obviously understand that way of working as well, right?

Chuck Longanecker:    They have to or else they won't work with us, and it's okay, right? We have really ... we don't have a sales team. We have very frank conversations. We try to help people first and if there's a good click, a good fit, they understand the way we work. Usually it's a reflection of the way that they work and so we just seamlessly work in there and kind of take over as their Chief Design Officer within their company.

Paul Clifford: Right. Does some of that stem from like the whole lean sort of approach as well really not ... as you said, not build out scopes and specs like that, but let's sort of mock something up, let's see if that works and see what the reaction and the feedback is or customer development as they call it in the Lean world. But trying stuff out and then molding it and then changing it and iterating it and then eventually ...

Chuck Longanecker: Absolutely. We wanted to approach everything with a very common sense approach. When we first found Eric Ries and his writings were like ... this is the way we've been thinking and finally someone organized it, we were so relieved. We were like, "Oh good, we can just kind of follow what he's figured out as we were doing portions of it." Fortunately, we got to work with Eric as well so we better implement some of that Lean approach and methodology. See absolutely, we look at it less like we're deciding to go Lean, we're deciding to go agile and more so that let's go common sense.

When someone comes to us to build or design something and ask us how much it's going to cost, the answer is we have no idea, right? We don't even know that the approach that you're moving in is correct. We have to test, we have to learn, we have to communicate with potential clients or customers or users, do that customer development, create the prototypes, iterate on the prototypes until we actually see some growth and then we can go full bore into what the product's going to be.

Or if we're modifying an existing product, there's so much digging of quantitative, qualitative analysis that we need to learn from to determine what's the greatest path. The whole thing, as Eric would say, is that startups are uncertain. There's uncertainty everywhere. We kind of embraced that. If we need to change, we need to pivot, then the way our model works since it's just a recurring subscription we can pivot on a dime. It doesn't matter, right, and it doesn't cost them any more money.

Paul Clifford: Because you're not working within a fixed framework.

Chuck Longanecker: That's right. That's what's allowed us, aside from what we do on a services perspective, to keep building products so we're able to carve a certain percentage out of our staff to build these products and continue to learn, continue to go through the agony and get more and more ambitious with every product we build.

Paul Clifford: Right. As we're talking about products specifically, one of your great products that you sold I think to Crazy Egg was Hello Bar. How was that born? Did you just come up with this idea one day and thought, "Hey, it'd be really cool if I did this."

Chuck Longanecker: Yeah it was ... I have to give credit where credit's due, Matt from Sitepoint had started Flippa, and Flippa which is a website for selling websites had a little bar up at the top that they had hardcoded in. It's like wow, that really grabs your attention but doesn't take away from the experience of the site.

We were looking for an idea, we had kind of written on a whiteboard and said the next thing we build, we want everybody else to look and say, "Man, I wish I would have thought of that." We wanted to build something so simple because it's so hard to make things simple and so easy to make them complex, right? We got this idea and we asked ourselves, "Okay, what's one thing you want someone to do on a website? A visitor comes to a website, what's the one thing that you want them to do?" You've got 2, 3, 4, 5 seconds, right?

Our theory was you want to deliver a simple message and a call to action, and where do you do that on a website? It's kind of random, right? You could put it in your nav, you could put it in the header, you can make a big red button, you can do all kinds of interruption kind of stuff but the user's not going to be trained to look at a new place on the site. So we decided the top area of the site and putting a toolbar up there that was unobtrusive and smart would be a great way to get attention, deliver that message and call to action and then go away if you wanted it to go away.

Fortunately, it did catch on and so we actually spent a ton of time designing that little 33-pixel bar. How does it look best on all these sites? We had a lot of different versions and we used an iframe tool so we could actually have the bar and we'd bring in all these different sites and we'd try them on big sites and little sites and beautiful sites and ugly sites. And finally came to a point where we found something that looked great and then we had to go through the whole thing with color. Strangely enough, we came up with the orange that actually worked well with everything as well.

Paul Clifford: I think the simplicity of it is ... what you just said, it's really hard to make something simple and really easy to make it complicated. I think that's something ... I mean I always struggle with that, I must admit, and when you're building software, trying to keep the features out, trying to say no, and when you look back at some success stories like I think Buffer for example, it's a very simple concept, what they're doing in terms of the social sharing and everything, but hugely successful. I guess is that something you really instil within your team, within the people who work with you as sort of one of your design ethos's for one type of expression?

Chuck Longanecker: Yeah, absolutely. I mean clearly we can't claim that it originated from us. Dieter Rams, it's one of his 10 design principles which is keeping things simple, design is simple. But what we do instil specifically is this concept of betterment. If we walk around after this and you listened to some conversations, you're going to hear people say betterment or make it better, right? Kind of our methodology is not just design this, design that. It's actually what designs do it, makes things better.

The concept of betterment ... there's a definition which is incremental improvements to create exponential results. If you make a few things better every day, you eventually get exponential results. There's a formula that we use internally that involves simplicity, and it's very simple of course: simple plus compelling minus friction.

If we go find friction, and friction's easy to find, and we don't look just at something that that is friction, we look at some friction that is affecting many, many people. We actually look a way to remove the friction or replace it with something simple and compelling. Simple because why make it complicated, that's not actually solving the problem.

Simple adds to the almost emotional IQ of a user when they come to a site, they naturally will be able to understand how to use it. The compelling is just that little delightful thing, compelling is a touch screen over a button membrane. It's something that just lights you up a little bit that makes it feel a little bit good, gives you a bit of a positive feedback when you use it.

Paul Clifford: Right. So that's obviously instilled in your team when they're approaching design, right?

Chuck Longanecker: Correct.

Paul Clifford: I guess that's probably what makes ... or nowadays, probably  what makes or breaks an app to a certain extent, do you think? Because I've heard the term emotional design used a lot, and the way I connect with that is that the market in terms of products is quite saturated. Very rare something completely new comes along, right? There's lots of me-too  products, but I think the ones that win are the ones that really draw you in because you just love to use them. I guess, and there's not necessarily a question here, but I'm just following your thinking in terms of taking those what you've in that formula and applying it into design user experience is what creates the emotional design, does that make sense?

Chuck Longanecker: Yeah, absolutely. I think that's definitely part of it and that equation works towards anything. It can work for manufacturing, it can work doesn't have to be just design. Our goal is to be Officers of Betterment, creating betterment, no matter what we do, we happen to be doing design right now. That's our tool that we do it with now.

To branch on what you said as well about those simple apps maybe the better ones or the ones that win. I think it's a little more than that as well is that life is made up of moments and a collection of moments makes an experience. And experience is the fabric of life, right? Our experiences are what bind us together, and kind of create what I call this experience DNA. It's how we see the world and how we're moving through the world.

I think if you can find ways to make really great experiences and meaningful experiences through these apps, that's what allows them to win. That magic, right, it's talking into your phone and having it send directions for you. That's not complicated on the front end, it's incredibly complicated on the back end. But that magic in that experience it reduces all that friction and allows you to do something you couldn't have done in the past, right?

I think that's that kind of a-ha moment you have with these apps. And even something like Flipboard, which came out a while ago but I saw people buying iPads to use Flipboard. And they didn't invent RSS or they didn't even curate the content that well. It just looked really good and it was fun to flip through, right?

You could absorb it better, right, as opposed to looking at Facebook, just the News Feed and kinda then going page per page. You can actually have this more immersive experience. So, I think the experience is just like that one thing that defines us. It's a funny thing because it's hard to define an experience in general and what is a good experience. But that's why we use all these customer development and Lean tools to validate our ideas, right?

Paul Clifford: Yeah exactly. I guess If you're talking and a lot of people listening to this will be ... there's plenty looking to scale. But it's also people looking for that idea, people looking, who want to build a SaaS app or any software. What I tell a lot of people is don't try to find the unique idea, they're very, very  rare. Find something that is working because then you know there's a market and then work out how to make that better in some way. Can you offer anything along those lines in terms of advice to help people ... how would anyone look at something to try and make it. You know create an app that's going to touch people in the way you described.

Chuck Longanecker: I'm really big on your personal like higher purpose and values in life, right? One thing I warn people against is like, "Oh look, there's a new market opportunity over there. Let's go take that," right? It's in the financial market or it's in the real estate market. But if you really don’t give a shit about those markets, you're not going to succeed or if you do, it's not going to be fulfilling for you.

I'd say first, look inward, look at what you love to do, look at what you're passionate about and where you want to make a difference. That's kind of the first step, and so I love digital, I love experiences, I love design. All of these different aspects and so that's the way I want to impact things.

It's different for everybody. Some people are passionate about fitness, some people are passionate about healthcare, some people are passionate about travel, right, so I would start there. And then look out where the friction is, where’s there is something that you can solve, where’s there is something you can make better. It could come from your personal experience but you have to be careful with that, right, because some very particular people have very particular habits and wants and needs and that's a very small market.

If you can identify what that problem is on a larger scale, and then you can use, what the third part is your skills to be able to fix it, right? If you have competencies in those areas and you can see a way from the beginning to end, you know you're on the right track to fix something. Now executing that vision and actually culminating it to a complete vision takes a long time. You have to peel back those layers. I feel like sometimes, it takes me a couple of years to peel back the layers to the pure essence of the idea and then I could truly execute it at that point.

You're always looking for it, you're always working at it every day, you're always kind of shaving off another layer. We have a-ha moments on our product filament everyday and we're like, "Oh wait, it's this!" The next day, it's not something else but it's more of that, right? It's micro dialing things in to be more and more clear about what you're going to do. I think putting those two together, because it's a long and arduous road, so you got to be passionate about it. You want to affect a large group of people or else there's not a good chance of success, right? And then you want to be able to have these skills that you love to do every day. It's repetitive motion every day to build a company, and so you have to be comfortable doing the same thing every day.

Paul Clifford: Yeah, got it. I think that you touched on filament there for a second and to a certain extent, and correct me if I'm wrong, but that's almost the case in point. I think you've identified that there's all these websites where they're needing to put in plugins do this and bits of code to do that. Where you've come from is really these are the best plugins or bits of code that you need to improve your traffic or your social or whatever in your site. And you're almost curating to a certain extent these little apps. But where you're delivering is maybe, using your term, reducing the friction and implementing them straight into your website. Is that fair to say?

Chuck Longanecker: Yeah, that's right. I think we got lucky when we figured this betterment thing out. The way we look at it is that on our services side we're helping clients make their business better with our services and if we're not making their business better, our services should no longer be used, right? That's our measure if we're creating impact and value for those customers.

When we blog, we try to share what we've learned with all of our readers of how to do things better. We share our process, we share our culture, we share how to design, we share all these things so that they could take it on their own and make things better. With filament we had the a-ha, we're like, "Wait a second, this is for people making their websites better and these simple tools."

What it was born out of is that design is hard, it's very hard. It's hard for us, we've been designing our new website for 6 months now. It's very, very difficult and it's expensive because of that. We feel that design should be more democratized because it's the end users that are losing in this. You go to a website, it's difficult to use. You want to do business with these people but it's just too confusing, right?

We want to create these tools so it's easier to have good design and ultimately impacts the user, right? The thought process is if we help people make their users happy, their users are going to take care of those website owners. They're going to do business with them or follow them or share, whatever it is. That's the idea of filament that was born.

The friction that we noticed is that as we do a lot of this work for our clients and activation rate, which means if you have a web app that you have to drop code for, a good one is like 50%, which means that everybody you sign up, you lose half just automatically. Then you have all the rest of the following, you have to deal with at that point. Dropping code is really tough.

The other thing is that that curation you hit on as well is what apps do I use? How do I improve my site? There's not a good source of what the best in class apps are and there's not necessarily guidance. There's great sites like where you can go to and you learn a lot of this stuff. But no one kind of brings it all together for you. Our hope was to help both users, website owners, to be able to move those apps into their site, help the web app creators to get those apps installed more easily and then ultimately the users to have a better experience.

Paul Clifford: Yeah. So people can go to ... is it, is that right?

Chuck Longanecker: Yes.

Paul Clifford:  And they can just register straight away and start using those?

Chuck Longanecker: Yep, completely free.

Paul Clifford: And it's really drag and drop, isn't it? I mean I've used it, I've got it on one of my sites.

Chuck Longanecker: There is one little dirty secret which is you do have to drop our code once but then you don't have to do it ever again. If you're on WordPress, there's that WordPress plugin that negates that.

Paul Clifford: Right, cool. Let's just talk a bit about maybe the startup community in general because since I came to San Diego, really knowing it from a marketing perspective and I found like a huge sort of thriving hub of startups either starting in San Diego or moving some of them further south. I've kind of always believed you don't need to be in the Valley to have a great startup. But I can see things really accelerating here. Is that what you see now? How has it changed over the past year, I guess, or 2 years?

Chuck Longanecker: Yeah, I can tell you how it has changed over the past 10.

Paul Clifford:  Right.

Chuck Longanecker:  I'm the old guy here. In the early 2000s, it was pretty much non-existent. You had DivX, which was pretty great. The rising of, which went public not too long ago and was recently purchased. As well as ProFlowers, and those guys provide commerce. But aside from those larger organizations, we didn't have much going on.

As the Web 2.0 movement came, we had a nice surge of new startups happening but had zero capital. Capital was a little drier in general at that point in time, and it was even harder to go travel to get that capital to actually build stuff, and stuff cost more to build if you were to think about it. You'd have to go raise a good amount of capital and then take that capital back to San Diego, and a lot of VCs didn’t like that.

There was a little start-stop that happened during that Web 2.0 period. That was frustrating but we do have a few startups in town like TakeLessons and Mogul  that came out of that era, as well as that started as Assistly was sold to Salesforce recently. Now you have a whole another set of ... I guess the game has changed, right? Now you have people using AngelList and raising their seed in angel capital.

You have people actually finding funds here in town or raising capital from outside of town and a lot more fast-moving startups. Before we were a lot of bootstrap people, which is great. I've been bootstrapped my whole career, but it's a long road that's why I'm on a 12-year-old startup. It definitely is ... it's like the third coming and I think this time it's got legs.

The thing that was missing the whole time was community support. One of the challenges about San Diego it's a beautiful place to live. It's so beautiful that it's really hard to get people to come together. It's very spread out. Everything is 15 minutes away but it seems like everybody is always 15 minutes away and not here. Sometimes it's hard to get people together, it's hard to keep them together. The surf when the surf is good. Coding isn't happening. But I see that changing and I see the community of entrepreneurs supporting it which is really great because you pull yourself up by your bootstraps. You don't depend on some type of marketing or PR organization here in town, you don't depend on capital, you just depend on yourselves and I think that's the only way we're going to be able to thrive in this community here.

Paul Clifford: Right, okay. I also see Santa Monica coming up as well. In fact, I think  I looked at yesterday and someone sent me a link for like a mapping tool called Represent, have you seen that?

Chuck Loganecker: Ah, no.

Paul Clifford: Yeah and I think ... do you still run like a San Diego hub or website for startups?

Chuck Longanecker: I used to do Startup SD. I've relinquished that as it became too much to handle.

Paul Clifford: Right. Whoever's doing the hub, if you like, or the online hub should look at that as well. Because what Represent managed to do is, I think it's just open source code but it just instantly maps on Google  maps all the start-ups in the L.A area. And so all of a sudden you've got a complete map for Santa Monica which is very dense and a lot of app in there and I think that would be good to have that type of thing in SD as well.

Chuck Longanecker: Yeah, absolutely.

Paul Clifford: It's a very, very cool tool.

Chuck Longanecker: There is a site called, that they've been amassing database of all the startups there as well, so that's a good place to check out.

Paul Clifford: Yeah, maybe I'll touch base and get them to do that. I don't think it's complicated to do this because it's open source, right?

Chuck Longanecker: Right. Yeah absolutely.

Paul Clifford: I'm notorious for hacking codes.

Chuck Longanecker: We need more people like you.

Paul Clifford:  I don't know, especially talking to someone at the top of the design world, sometimes I feel guilty about some of my sites which are just generally hacked together using WordPress and the most good-looking theme I could find on CodeCanyon. Put those together and that's my site.

Chuck Longanecker: But the great thing about that is you always have to start some place. I mean quite often we'll talk with people and we'll say, "You know, you're not ready for the most polished design yet." Just get it out there, get it working, grow it. And then when you get traction, that's when you start really investing in the design. If it is amazingly designed, it doesn't mean that people will come, right? It helps but there's still ... unfortunately sometimes, the best design, aesthetic design in the world doesn't always perform the best either.

Paul Clifford: Yeah. It's really about taking that massive imperfect action, as they say, right? Just get something out there first of all and then improve on it.

Chuck Longanecker:  I love Reid Hoffman's quote around ... I think he said if it doesn't look like complete shit, you shipped too late.

Paul Clifford:  So much truth in that. There on the startups we're also talking about age and how that's changing. What are your thoughts on that? We touched on that earlier.

Chuck Longanecker:    Yeah, it's funny, I feel young. I think we're both pretty young in all consideration of the idea. We were just mentioning about how venture capital is looking to invest in younger and younger people based on the drive and I guess maybe their ability to survive on ramen and redbull and just not having the family, not being tied down and just being able to hustle. Because ultimately at the end of the day, they want to get 10x, 20x, 100x out of what they're looking to do.

As you get older, I think your priorities change a little bit as they should. Or maybe you found a bit of success already and your ambitions are different. You learn to slow down and appreciate life passing you by as opposed to staying up all night to try to push the code live or get coverage in a tech blog, and you kind of realize that's not the stuff that necessarily matters.

Hopefully I'm not talking VCs out of investing in me but I think that that is a paradigm. I don't think it's necessarily true. I think on the other side of the other hand, I feel like I've personally become a 38 a more mature leader. And, I've been able to sit back and make my mistakes, I still make a lot of them, can catch them a little sooner now. I can be more calm and learn how to actually put a better product out there and the product is made by a team, and the team are people, they're humans.

They're not human capital, they're actually humans just like you and I. And invest in the culture and invest in them is first and foremost our priority. What happens after that is amazing. You have happy people that are passionate about what they do and the product just takes off and becomes so much better. It's not a matter of how long you work, it's a matter of where your headspace is at, how well you work together as a team.

It's not the team necessarily that practices the longest or that studies the hardest or that works the hardest. It's the people that work the best together. We've invested a ton in culture and I think that's hard if you're a young person, it's really hard to be able to lead a company to do those types of things. You don't have that experience, you haven't had all of those mistakes that force you to learn, you can't read about that stuff in a book really.

Paul Clifford: You don't understand the life experience element of it. I also see another angle out of that as well especially and maybe this applies more to bootstrappers. I also think when you go through the family phase and you need to feed the kids and you need to send them to school and all that, then another sort of drive comes out. I think for one of a better phrase, the more mature entrepreneur or the person who is leaving their corporate job and setting up on their own, I think they should never be overlooked because I think they're more hungry.

They've burnt their bridges. They have to deliver. I think often some entrepreneurs who pivot a lot probably come out of that sort of world. Because it's not about the product. It's about the person who can actually make it happen, and often I know from myself I need to push up, backsides sometimes just to get stuff done. And having the family driver is always there.

Chuck Longanecker: It's interesting to be motivated by your mind and the family as opposed to other things that could be motivating you when you're young and distracting you. I think that's definitely true and I think naturally, you also want to make greater impact later in life. To make a greater impact, you've got to do pretty big things.

I think as opposed to just creating a product that has a ton of users, you want to create a product that creates world change and there's a lot of value in that, too. I think that's another thing that goes overlooked at times as well. It's interesting, I can't remember this specifically but I think there was a series of startups, I think it might have been Twitter, it might have been one of them, that were starting with people 35 and over. So there's a list out there some place that we can maybe put in the show notes, and it's pretty amazing to see which companies were started later in life by a lot of this organizations.

Paul Clifford: Yeah I'm wondering if there's any data on that collectively it would be really interesting, because I know, and we touched on this earlier, but I know I'd always wanted to be an entrepreneur and that's probably why I always worked for startups when I was much younger. The last one took a lot longer to mature, to sell, etc. The problem with being in a startup for so long is when you have the family commitment and kids and schooling and all that sort of stuff, all of a sudden your committed outgoings is so high, it's really difficult to make that leap. I think for people who are in their desk jobs who want to leave, it is possible to do that and you can do it. It just takes that action, that step to actually get out and do it.

Chuck Longanecker: And the support of family.

Paul Clifford: Yeah.

Chuck Longanecker: Not too risk-adverse.

Paul Clifford: Yeah, I know. Try persuading a wife that you want to go to San Diego.

Chuck Longanecker: Yeah, well there can be worse places to go.

Paul Clifford: Exactly. Chuck, we're coming to the end really and I’ve really enjoyed our chat. The we talked about, we talked about design, culture and the culture of employees and motivating your staff and your team and everything. For people who were thinking of starting up, any sort of tips or any advice you can give them in terms of what's important to get right in terms of their new app or their website or anything like that?

Chuck Longanecker: Yeah. I'd probably summarize a few things I've said, which is one is make sure it is something that you're passionate about or a problem that you want to fix as opposed to just a market opportunity. I think that's number one. I think that misery loves company and I think if you have an opportunity to work with someone that you trust, I think that's pretty great.

I've worked with friends and it's ... right now my business partner is a friend and there's ups and downs. I wouldn't trade anything for in the world, I trust him more than anybody else other than my wife and that's been phenomenal. To be able to share that with someone you care about, to work on things ... with these things and to not be alone. When you're alone as an entrepreneur, it's tough, right, because people will not understand what it's like to be you within the organization.

Other entrepreneurs will understand but you only get to see them every once in a while. Find a partner in crime, I would say, if at all possible. If you can be different, be technical and creative or vision and marketing or operationally sound or something like that. Don't be the same because it's those differences that create your strengths.

I would say that, and then I would say build your foundation on culture. If you have an opportunity ... if you have a great team, that great team can come up with an idea. Ideas are so cheap, right? Every time we take a shower, we get a new idea, so it's about finding the team, it's about aligning the values and the culture of that team and about making that idea everybody's because that's what will be executed even better.

Sometimes it's hard to start with a team because there's no capital to do so, but I think if you're going to be inspirational, it's a good place to start to get people to kind of believe in you and start there, it's a great way that I think start a company on that foundation itself.

I think there's a period when you start a new company or a new product, I'm sure it's a like the hero's journey, right? There's highs and lows. There are times where you just need to keep on pushing and there's times where you just need to kind of shut it down and try something else. I don't believe, and waging the war for years and years on end if you're not seeing results, it's like the definition of crazy is to do the same thing over and over again and expecting different results. I just go out there and as they say fail fast, but be excited about making mistakes because you're going to learn from it. When you get those wins, just keep following that path.

Paul Clifford: Right. That's brilliant. Chuck, I really appreciate you coming on the show. I found it really exciting and interesting interview. If people need to get a hold of you, via

Chuck Longanecker: Yeah, And we recommend everybody to takes a look at our blog, we try to give away all our secrets on it. So you can sign up via  email, or if you want to say hi, just hit the contact button.

Paul Clifford: Brilliant. Chuck, thanks very much for coming on the show.

Chuck Longanecker: Thank you.

Paul Clifford: If you enjoyed the show, you can get the show notes from And if you are not a subscriber and you're listening to this from the iTunes store, then please visit and sign up.

That's it for this episode. Look out for next week's show. I'm Paul Clifford and thanks for listening.

Recommended Resources:

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2. Eric Ries Author of The Lean Startup - click here

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6. Filament - click here

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8. SalesForce - click here

9. AngelList - click here

10. Start Up San Diego - click here

11. CodeCanyon - click here