Direct Sales and Starting Something New with Nathan Barry

Nathan Barry, founder of ConvertKit, on Profit. Power. Pursuit. with Tara Gentile

Connect More With Your Audience By Doing Less: 6 Marketing Automations You Need Today

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Tara:  Hey everyone, welcome to Profit. Power. Pursuit.  I’m Tara Gentile, your host, and together with CreativeLive, we explore the unique strategies that creative entrepreneurs use to take control of their lives, profit from their passions, and pursue what’s truly important to them.

Today, I talk with my friend, Nathan Barry, a software designer and founder of ConvertKit, an email marketing service provider that helps you build your audience and convert them into customers.  Nathan made his first foray into digital entrepreneurship with The App Design Handbook, a guide to design beautiful iOS applications.  He started ConvertKit in 2013 when he found all other email marketing tools lacking the set of features he wanted as a content marketer.  It’s now on track for its first $1 million year.  Nathan and I talked about making the decision to pursue growing ConvertKit full-time, and put his lucrative digital products business on the back burner, the direct sales strategy he used to woo influencers to his product, and what he’s learned about building a Software as a Service venture.

Nathan Barry, welcome to Profit. Power. Pursuit.  Thank you so much for joining me.

Nathan:  Hey, thanks for having me.

Tara:  Absolutely.  So I want to talk lots and lots about ConvertKit, both how that business works and how it can make our listeners businesses work, but first, tell us how you got started with digital entrepreneurship in general.

Nathan:  Yeah, so I started out as a web designer in high school.  I learned how to write HTML, mainly because it had a really quick feedback loop that I thought was cool.  You could just change a tiny bit of code, and then refresh and see what change that made, and so it just got me excited, and then I started working on all of that, and then from there, I did freelance web design, and then got into software design, and got a job at a software company, and then eventually led their design team, and then I was always fascinated by the world of, like, you know, side projects and building little products rather than just doing services.  And so I followed people like Jason Fried and David Heinemeier Hansson from Basecamp, you know, and loved anybody who was basically making products, and so on the side, I started building iPhone applications.  Had got a couple in the app store.  Ended up quitting my job to work on that and also do consulting, and then I started getting asked a lot about how to design applications.  All of my developer friends were asking me for help with their iPhone apps, and there weren’t really any good resources to point them to.  So I wrote a book called The App Design Handbook.  I didn’t really have a blog at the time, or I had a blog, but nobody read it, and I just started working on promoting this book and writing iPhone application design tutorials, and then I built an audience of like 800 people, did a book launch that did very well, and so it was like whoa, okay, there’s something to this training business idea, and then ended up writing more books on software design and on marketing, and then just kind of built a big blog audience, and made really a great living from selling books on technical design and marketing.

Tara:  Nice.  So what misconceptions did you have when you started your business?

Nathan:  Oh, that’s a good question.  I didn’t know the power of an audience.  I really had no clue how to build an audience, quite frankly.  I thought that only like the internet famous people could build an audience, and so when I would hear about someone doing a product launch, and you know, they might sell a book and, you know, it would sell, you know, $50,000 worth or $100,00 worth or something, I was like, yeah, well, of course you can do that, because you’re famous, you know, and I didn’t realize … like I made no connection between how people got to that point.  And so it wasn’t … I had to learn this lesson from like three different places before it sank it, but the idea that in order to become one of those internet famous people, you know, who has an audience of 10,000 subscribers or whatever, all you have to do is teach, you know, and so the story that made this really sink in from me was from a guy named Chris Coyer, and he had this site called  So as a web designer, I was really into, you know, all those web design blogs and articles, and I remember when he came out with the CSSTricks site, I looked at that, and I was like, eh, he’s actually not … like, his content’s not that advanced, and so I’d looked at that, it was good, but I already knew everything that he was teaching, and I kind of remember thinking, like, okay, if I already know everything he’s teaching, like he’s not that much of an expert, and so he would come out with more stuff, and I’m like, oh, yeah, already knew that.  And then eventually, his stuff got better, and then like later on, I’d be like referencing it or sending other friends to it.  They’d ask me a design question and I’d say, oh, why don’t you check out, you know, Chris’s site.  And so all along, we had the same skill level, we basically learned web design at the same pace, and then one summer, he came out with a Kickstarter campaign, and basically, what he said is hey, I want to redesign my site, and I want to be able to take a month off of client work to do it, so I want to raise $3000 on Kickstarter so I can do that, and as a thank you, if you back this project, you know, as I go along, I’m going to create all these design tutorials, and if you back the project, you get access to them.  So he ended up raising something like $85,000 on Kickstarter.  And I’m looking at this going wait a second, Chris and I are the same.  Like we have the same web design ability, we started it basically the same time, and we’ve been learning at the same pace.  So how does he have the ability to effectively flip a switch and make $85,000 on Kickstarter, and I have nothing like that at all?  And so that’s when I realized that the difference, and it was a massive difference between us, is that when Chris learned something new, he taught it, and when I learned something new, I kept it to myself and just, you know, applied it into my next freelance project.  And so that’s what I realized.  The only difference between the people who are internet famous and the people like Chris and me was that one set of people were teaching and the other wasn’t.  And so from then on, I just became determined to teach everything that I know.  I even have t-shirts now that say that.  So it’s kind of become my life mantra of how, like how to build an audience, and all you have to do is as soon as you learn something, teach it to everybody else.

Tara:  Yes, and I totally missed an opportunity, because I forgot to wear my ConvertKit t-shirt today, and so now I feel like a big old dufus, even though this is an audio-only podcast.  So I love this takeaway, because … and I wrote a post something very similar, you know, because one thing that I hear from people often is that they don’t feel qualified to do this or they don’t feel qualified to do that, and it comes down to the same thing where they see … they see, somehow, a substantive difference between them and the people that they admire, the people that they see doing the things, and what you’re saying is that it’s not a substantive difference.  It’s not something that I’m born with or you’re born with that they are not born with.  It is in fact just action that you and I have chosen to take.  And even in my own story, there’s that sort of realization of wait a second, if every … if there are other people doing this, then I can do this, too.  There’s nothing different about those people and me, I just need to do it, and that’s huge, because you know, not doing the thing, not taking action is the only thing that holds us back from getting where we want to go, right?

Nathan:  Yup, absolutely.  The way that I’ve thought of it is that those people you look at that are experts, they’re not teaching because they’re experts.  They’re experts because they teach.  So you start teaching, and you become that expert, and then you get asked to speak at the conferences.  You get asked to be the guest on podcasts and etc., but it all starts with teaching, and it can start at a very, very basic level.

Tara:  That’s fantastic.  So this leads me directly to ConvertKit, because I feel like I have this problem with ideas like ConvertKit.  In other words, I see me as, you know, a founder in the information marketing space, but I feel like there’s a substantive difference between me and a founder in the SaaS space or the startup space, and you know, when I look at it objectively, of course, that’s not true, and maybe you dealt with that, maybe you didn’t deal with that, but you decided to move from information marketing into a, what looks much more like a startup model and build a SaaS product, which is ConvertKit.  So what gave you the idea for ConvertKit, and what kind of gave you or what was the sort of permission that you gave yourself to make that move?

Nathan:  Yeah, so what inspired ConvertKit was really me learning how effective email marketing was at actually just driving sales.  I … when I started selling the books, I kind of expected that like Twitter and Facebook would be the best converting channels, because like Social was the new thing, and it turns out I was totally wrong.  Like email drove more sales than all the other platforms combined.  And so then I was like hey, guys, this email thing is amazing, you know, to other marketing friends.  It’s like, yeah, we’ve known that for a decade.  I’m like okay, all right.  So I was getting the best conversion rates over email, and then I was learning all these more advanced techniques, like you know, drip email sequences to time your pitch message exactly to the right timing for each subscriber, doing content upgrades, you know, tagging your customers, all these sort of things, and I was using MailChimp, and I was just fighting it at every turn, where I was just like why are these best practices so hard to implement.  And I would find myself not doing things that I knew would increase revenue, just because it was kind of a pain in the tool that I was using, and so I very conveniently had a background in software design, and you know, user experience design, and so I thought, okay, I can do this better.  And so then I started down that road, and I was thinking of starting it as a side project and that’s what I did.  So I balanced the, you know, the information products and the training business along with the software business in order to get that off the ground, and it actually took a long time to get it going, but then, you know, over the last year or so, I’ve fully made the switch the other direction, so now I, you know, put really 100% of my time into ConvertKit and the software business, and effectively no time, which is unfortunate for my blog, but you know, almost no time into the training side of the business.

Tara:  Yeah.  Can you say a little bit more about how you actually made the transition?  Not just the decision, but you know, you’ve got a family, you’re a provider, how did you wrap your head around … what was the process of, you know, putting the numbers down on paper to figure out that putting your time and investing your money into ConvertKit full-time was the best way to go for you?

Nathan:  Yeah, so first, I should give a little bit of context.  When I started ConvertKit, which was in January 2013, so just over three years ago, it took about six months, and we got up to … six months after that to get to about $2000 a month in recurring revenue, and I honestly thought it was going to be easier than that, but okay.  Put in a bunch of work, got to the point, that was good progress, we’re on an upward trend, but then I also had, you know, the other, selling the design products and the rest of the business that was making really good money, and so I found it really hard to focus on like the long-term business and growing ConvertKit when the books and courses and product launches there could make really great money in the short-term, and so I effectively spent the next year and a half supposedly balancing these two businesses, but really, almost all my effort went into the training where, you know, you could do a $30,000 or $50,000 product launch, and almost no effort into the software side, into ConvertKit.  And so then in, like, middle of 2014, I was having a conversation with a friend of mine, his name’s Heaton Shaw, and he’s really well-known in the software and startup space.  If you’ve ever used tools like CrazyEgg or Kissmetrics, those are his companies.  And he just, we were walking back from dinner at a conference, and he just said, “Look, Nathan, it’s time that you admit that ConvertKit’s a failure and shut it down.”  And I was like, well, hold on, it’s not a failure.  It’s making like $2000 a month, you know, and he’s like, he was pretty firm, and he said, like, “Look, if you’ve been putting time into it this entire time, it should be way bigger than that.  If it was going to be successful, by now it would be, and you need to admit that it’s a failure and shut it down.  Move on to something else.”

And then he continued, because that sucked to hear, but so I was glad that he continued, and he said, “Or you need to take it seriously and give it the time, money, and attention it deserves, and build it into a real business.”  Because I was kind of working on it a little bit on the side hoping, yeah, once this takes off, then I’m going to switch to it.  And I think a lot of us do that with side projects, because you know, that’s what the hope is, but things don’t take off on their own, you know, 99% of the time.  They take off because we make them, and so what I did is I ended up waiting about six months to, or four or five months, before I actually acted on his advice.  And so the revenue of ConvertKit dropped down even further, so we were making $1300 a month at the time, and from there, you know, I finally had a decision to make.  Should I shut down ConvertKit, admit that it’s a failure and move on, or should I double down on it?  You know, invest real money and build it into something.  So I kind of came up with my own little framework for deciding how to make this the decision, and came down to ask myself two questions, and the first was do you still want this as much today as you did the day that you started?  And so for me, you know, do I still want to be the CEO of a software company as much now as, you know, two years ago?  And the answer was a resounding yes.  Like, I still really wanted it, and so you know, that was good, because if I didn’t still want it, then just shut it down.  Like it’s easy to move on.

Nathan Barry, founder of ConvertKit, on Profit. Power. Pursuit.But then the next question was, you know, have I given this company every possible chance to succeed?  Because if the answer there is no, then okay, there’s an opportunity there.  If the answer is yes, then it’s like, okay, well, if you’ve really, truly given it your best effort and it’s not working, then like shut it down and move on.  But in this case, I looked at the time I’d been putting in, and I hadn’t given it every, you know, possible chance to succeed, and that didn’t, like, if I wanted it more than ever, why … why was there a disconnect there?  And so that told me, okay, there’s still an opportunity here, and I decided to … to double down on it.  I invested $50,000 into the company.  I hired the best developer that I’ve ever worked with to lead the development team, and then I just started selling.  Like I, instead of waiting for customers to come to me, I made lists of all the bloggers and, you know, people doing email marketing and just tried to get on calls and email with every single one of them, and it took time, but we gradually turned the revenue around.  You know, we started growing about 20% each month.  You know, three months later, we were doing like $4000 a month in revenue.  By June of … So I made the decision October 2014, by June 2015, we were at $10,000 a month in revenue.  $25,000 a month by October 1st.  $83,000 a month by Christmas.  That’s a magic number, because that’s a $1 million a year run rate.  And then now, we’re just about to pass double Christmas, so today, we’re at $160,000 a month in revenue, and growing 20% month-over-month, and it’s turned into this amazing thing, but it wouldn’t have happened without deciding to really double down and focus.

Tara:  That is awesome.  So I want to talk more about that.  I have some very specific questions about that a little later on, because you know, this decision to sell, sell, sell, and to stop waiting for people to come to you is absolutely huge, and we need to pick that apart, but I want to go back to the beginning just a little bit, just so that people can understand.  Did you do the initial development on the product or did you outsource that?

Nathan:  Yeah, so I did the design and the front-end code, so that would be the HTML and the CSS.

Tara:  Okay.

Nathan:  And then I outsourced the Ruby On Rails development.

Tara:  Okay, fantastic.  And where did you find that initial set of customers that, you know, were supporting that $2000 a month revenue at the beginning?

Nathan:  Yeah, so I found them effectively just from my blog audience.  From the books and courses that I had written, you know, I had … I don’t know how many.  I think when I started I maybe had 6000 or 7000, when I started ConvertKit, I had 6000 or 7000 subscribers, and so I told them about it, and enough people signed up and tried it out.

Tara:  Nice.  And do you think … what do you think was their main reason for signing up then?  Was it because wow, Nathan developed an email marketing provider, that’s awesome, or was it a particular benefit?  What do you think got them to sign up?

Nathan:  I think the pitch was fairly compelling because it was I ran to this specific set of problems that you probably have, too, and you know, and I solved them for myself, and so, you know, a lot of people who are feeling the same problems with MailChimp, you know, being charged for duplicate subscribers, all these other things, they were like yeah, this sounds great.  Now, the downside is that the product, the ConvertKit product wasn’t super robust at the time, and so, you know, it was limited in who stuck around and so it was definitely an uphill battle, but that … the initial sales pitch is what got people over.

Tara:  Okay, awesome.  Can you talk more about the particular problems that you saw in the email marketing space that you decided to solve with ConvertKit?  Because I think this is a really compelling part of how you decided to build the product to begin with.

Nathan:  Yeah.  So my idea was that there’s all these best practices in email marketing, and you shouldn’t have to work for them.  They should be built into the product by default.  And so when we focused in on professional bloggers and you know, content creators, then that meant, okay, I can solve just their problems.  And so the main ones were that you should be able to tag your customers.  So you know, you should never send a message to someone telling them to buy a product that they’ve already purchased.

Tara:  Amen.

Nathan:  The next one is you should do content upgrades on all of your content that’s, you know, the highest value.  We had a ConvertKit customer recently, they have an amazingly popular blog, and they had 400, they were averaging 400 new subscribers a day, and they went back to their top 15, they went into Google Analytics, ran a report, the top 15 articles, and then they made specific content upgrades for those.  So instead of saying, like, the call-to-action being subscribe to my newsletter, it changed to being, you know, get this free guide on topic exactly related to the blog post, and they ended up doubling their subscribers per day based on that one change.

Tara:  Oh, so good.

Nathan:  So they went from 400 subscribers a day to 800 subscribers a day on average.  And so I was like, okay, that should be really easy to implement, and so I wanted it to be very easy to make it so that a form, when someone signs up, you know, they could get like the free guide or the free link to the video course or whatever right there in the email, and that should all be customizable.  And then there were other little thinks like if someone goes to our site and they subscribe to your email list and then they come back, most likely, you’re pitching, like the call-to-action all over your site is subscribe to the email list, and so I was looking at that going, okay, why is everyone, again, like the earlier thing, why is everyone pitching an action that has already been taken?  We know that that person subscribed to the email list, and so … and it’s not that hard to track.  You know, you can do some custom code and track when someone subscribes, and then show different content.  But out of, you know, all the professional bloggers I know, like three of them have done the work to custom code that sort of tracking.  And so what we built straight into ConvertKit was if someone signs up to your email list and comes back, that same form can now show different content just for them.  It could either hide itself so they’re not getting pitched on something they’ve already done, or it can show a call-to-action for the book or the course, you know, the next thing that you want them to buy.  And so we just built that into the platform once, and now every ConvertKit customer can use it, and it’s a very, very profitable feature.  So basically, those kind of things.  Every best practice I have learned about email marketing built directly into a product.

Tara:  Yes.  Which is why I love it.  So all right, awesome.  Let’s talk about more about the selling and the influencers piece here, because I think this is so, so, so important.  There is this misconception in content marketing, in digital marketing in general, that people … that the way this all works is that you build this thing, and then people come to you, and if there is anything that I have learned over the last 7 years, it is that that is completely false, and that even when we’re doing our very best job and we are getting people coming to us sort of organically, it’s because we’ve done the hard work of actually reaching out to begin with.  And so you’ve really focused in the last, like you said, six months, last year, on growing the customer base at ConvertKit by reaching out to influencers in different markets.  How did you decide on that particular strategy?

Nathan:  Really, I learned that there is a lot of people who were trying to … who I was pitching on ConvertKit through blog posts and that sort of thing, and they weren’t buying, and I didn’t know why.  And so that’s something, if you write a blog post pitching your course or whatever it is, and say that … say that’s read by 1000 people, and 10 people buy.  Well, why did the other, you know, 990 not purchase?  You don’t know.  They just kind of moved on with their day.  But if we’re having a conversation, and I, you know, verbally tell you all the benefits and say, “Would you like to buy it?”  And you … like you can’t just hang up the conversation and move on.  I mean, I guess you could, but if we’re friends, you’re not going to do that.  You have to actually tell me why it is that you’re not going to buy the product.  And so getting that feedback is incredibly valuable.  And with content marketing, you just almost never get that feedback.  People just silently move on.  And so I realized that I needed that feedback, and I realized that content marketing wasn’t working for me to sell, you know, this particular product.  It worked amazingly well for me selling the books and courses, and so I just … I started with the direct outreach.  I actually made a Trello board so I could track every conversation, which now, you know, there’s obviously way better CRMs and sales tracking tools for it, but I started really simple with Trello, and so the big things were I just made lists of people to reach out to, and then I made sure to follow up with all of those people, and it was just a lot of conversations.  And I started small, where the first people I was reaching out to were, you know, had 1000, 5000 email subscribers, and we just kind of worked our way from there, and you know, later on, we’re reaching out to people who had 100,000 subscribers, and you know, way beyond that.

Tara:  Yeah, and one of your big victories was getting Pat Flynn to switch to ConvertKit, right?

Nathan:  Yup.

Tara:  Can you tell us how that happened?

Nathan:  Yeah, so this is a case where your own content marketing will help your sales efforts a lot.  So if you’re purely sending a cold email, like that’s not going to get great response, but if you’ve been blogging and putting a lot of things out there so that these people might have heard of you already, then all of a sudden, it’s way easier to get a response to your blog posts.  The other thing is if you’re going to do direct sales, go to conferences.

Tara:  Yes.

Nathan:  Because there’s just a huge difference between some random cold email that, you know, you and I get tons of every day, and you know, a real person standing in front of you at a conference, you know, and just getting to know people.  So through some mutual friends, through my blog, stuff like that, Pat and I had had some conversations, and then we met once at a conference, and things kind of went from there.  But then I emailed him and said, “Hey, you know, would you consider ConvertKit?”  He said, “No.”  He had just made the switch to InfusionSoft and was really excited about it.  So I was like, oh, that’s a bummer, I wish I’d caught him before he made the move.  Too bad.  But then I decided to actually go down and visit him in person.  So we had enough of a relationship that I knew that if I showed up in San Diego, he would like take a coffee meeting, you know.  And my goal at this point, I decided, was to not pitch him on becoming a customer, but instead, to get him to promote ConvertKit as an affiliate, because even if he loved InfusionSoft, it was probably too complicated for, you know, his readers.  So I got coffee with him, talked through all of that, got him on board with, you know, him becoming an affiliate, or at least the idea of it.  We kind of worked on it slowly, and then, like a few weeks later, he came back to me and said, “You know, I’ve been thinking about this.  If it’s this … if everything you’re saying is true and it’s this good for my readers, like InfusionSoft is really, really frustrating me right now.  It wasn’t the dream that I was sold, and so let’s try out ConvertKit.”  And so in July of last year, he signed up, switched over from InfusionSoft to ConvertKit, and we weren’t allowed to talk about it publicly, because he was just trying it out.  But then he ended up, you know, really enjoying it.  And we get email from people who, they’d be like … they would see from his email list, you know, because the link tracking and stuff was coming through ConvertKit, they’re like, oh, did Pat just switch?  And then he would like quietly mention it in some live Periscope broadcasts, too.  Like, we actually got a bunch of customers, because one night at Midnight, because this is how Pat works, he was doing a Periscope broadcast, and he mentioned that he switched to ConvertKit and started showing people that over ConvertKit, and we ended up getting like 15 or 20 new customers the next day, like that night and the next day, which was huge for us at the time.

Tara:  Yeah.

Nathan:  You know, just because he was talking about it at Midnight on the internet.  So another thing on the sales side that we did was we started doing what we called concierge migrations.  So basically, we would have a conversation, and someone would be like, “Okay, this all sounds really good, but man, I do not want to move my email list.  That … like I love everything that you’re doing, but this is too much work.  I’m sorry, it’s probably just never going to happen.  Or it’s going to happen when I have time, which is also never.”  And so then we’d say like, great, totally understand that.  We will move your email list.  You know, migrate you from MailChimp to ConvertKit or from InfusionSoft to ConvertKit, and we’ll do it totally for free.  And so in the early days, I was doing this for anybody, and then later on, we set, you know, some limits.  So only the $100 a month and above accounts, and that kind of thing, but it just made the sales process so much easier, because it just removed that last objection right at the end where people were like, “I’d love to, but oh, man, no.”  And so when we removed that last objection, they were like, “Done.  I’m in.”

Tara:  That did it for me.  I mean, I had … I knew I had outgrown MailChimp years ago, even though I loved … like I love them, and I still love them, and I still recommend them, and they weren’t … it wasn’t what I needed anymore, but the cost of switching was so high.  Not in terms of financial decision, necessarily, although that could have been part of it, but just the time and the frustration, and so when you told me, “Well, yeah, we’ll do it for free.”  I’m like, uh, okay.  I mean, I would have paid you to do it, but doing it for free, absolutely, it removed that last objection, and it was so easy to say yes, because I was in exactly the same place.  Like this sounds great, this sounds amazing, it’s exactly what I’m looking for, and the cost of switching is huge.  So that’s great.  And I just want to emphasize for everyone again that, you know, we talk so much about marketing.  Marketing, marketing, marketing.  Content marketing, Facebook marketing, social media marketing, but sales is where transactions actually happen, and sometimes, that means getting on the phone with people, and I’m just so thankful for your example of how that can be so beneficial.  Are there any other strategies, tactics that you’ve used to woo customers outside of this influencer marketing?  You’ve mentioned affiliate marketing some.

Nathan:  Yeah.  So the other great thing about getting influencers is that a lot of people tend to follow them, that’s why they’re influencers, and so we, you know, worked on getting a good affiliate program in place, so we pay a 30% recurring commission, and you know, so that … that made it easy to get, you know, Pat promoting as an affiliate, and then just these other influencers in like the health and wellness space and in fitness and in all these other areas.  Some just promoting it to their friends, and others, you know, promoting it very, very vocally, and so right now, we pay about $10,000 a month out in affiliate commissions, and that’s, you know, increasing, you know, at a very quick rate.  So the three big channels, really, are direct sales, affiliates, and then just referrals, where you know, someone who loves ConvertKit just tells their friends, and it just kind of spreads from there.

Tara:  Awesome.  What has surprised you about developing a SaaS product versus what you’ve done before?

Nathan:  How hard it is to develop and maintain, and then also, how hard it is to sell.  You know, there’s something about with books and courses, just because you bought one, that doesn’t preclude you from buying another, you know.  We all kind of have a bunch of them that we buy and learn from and all of that.  Whereas an email marketing product or, you know, a scheduling tool or any of these, you pretty much buy one, you know, and you might switch from one to the other, which we’ve already established is a big deal, but it’s not … it’s not an impulse buy.  It’s a big decision, and you know, if you’re already using and loving one tool, you’re not going to buy another.  You know, you’re like you can’t do it.  So that’s been the hardest thing.  I thought it was going to be way easier to sell than it actually was.

Tara:  That’s excellent.  And again, to kind of point out this exactly what you were just saying, the home page for ConvertKit is just completely benefits-driven, and completely, you know, here’s why this is the best choice, here’s how we’re going to help you get over all of those problems that you have with your current provider, and I think that that really, I think it’s super effective, and I think it really speaks to, you know, what you just said.  Can you tell us what your team looks like right now?

Nathan:  Yeah.  So we have a team of 13 full-time people.  We’re distributed all around the world.  One of our … I’m headquartered in Boise, Idaho, and we have three, two other people in Boise, but then other, you know, like Nashville’s popular for us, Portland, and then around the world, we’ve got Thailand, Brazil, and Spain.  So the team is five developers, four support people, and then there’s three in the account management and sales side, and then there’s, you know, we’ve got one person in operations, I don’t know how many people I’ve listed.  Beyond this, it’s like everyone is overlapping between different roles, like Val, who’s amazing, who runs all of our marketing, you know, also helps out in support.  And so you know, beyond that, a lot of people are juggling multiple roles, but that’s the basic team.

Tara:  Awesome.  Do you have a strategy or system for managing your time?

Nathan:  Poorly.  I schedule the recurring meetings, you know, with each of the directors on my team, because I guess now, I still … I directly lead the support team, but everything else, you know, I have fairly limited involvement with, because I’ve just tried to set up those systems so the … like with development, I have a meeting once a week with my director of development.  We set the direction and that kind of thing, and that’s pretty much the extent of my involvement, because he just runs that entire team and does an amazing job.  And my team is really good about listing out all the things they need from me, and then getting them taken care of in one block instead of just pinging me all day long in Slack or something.  So that’s helpful, but at this point, my job as the CEO changes so often.  Like the company is growing so quickly, you know, that we’re doubling the size of the company every couple months, and so my job changes all the time, and quite honestly, I’m still trying to figure out how I fit into this whole picture, you know.  What it is that’s most valuable that I should be working on.  There’s a lot of strategy and that kind of thing, but then at the same time, early this morning, I was in Photoshop and you know, designing some new posters and getting some new t-shirts ordered and stuff like that, that I just wanted to do.  So it’s kind of a balance of all … all kinds of different things.

Tara:  Yeah, I do those things, too.  That’s … and that was exactly going to be my next follow-up question.  What are some of the things that you’re still really hands on, or that you find yourself being hands on with now?

Nathan:  Yeah, so I’m very hands on with customer support right now.

Tara:  Oh, okay.

Nathan:  Because dealing with the huge number of customers coming in, you know, and trying not to, I don’t want to just keep throwing people at the problem.  You know, I don’t want to be the sort of company where, you know, you blink and overnight, it seems to have gone from, you know, 15 people to 100 people type of thing.  I want to solve the core problems, so you know, we’ve been working very hard to get our customer support response times down, and so that … that’s a lot of my time.  I’m still fairly involved in design, because my background is software and user experience design.  So we haven’t hired a designer on the team, yet.  So I’m the bottleneck there, and that’s got to change soon.

Tara:  Oh, wow.

Nathan:  Yeah, and then I spend some time on sales, and I still teach some of the webinars as well.  So that’s kind of … I really work on a lot of different things, and that needs to change.  But then I also, you know, I cut out early yesterday to go skiing because we got an inch of snow and so, you know, just gotta do that.

Tara:  Oh, yeah, that’s the life, right?  I was going to ask you when you were talking about the team and you mentioned you have a couple of people that are on sort of the sales side of things now.  Are they getting on the phone with people the way you used to do most of?  Or is it more like internal sales?  What does that part of it look like?

Nathan:  Yeah, so their process, we do sales in two different ways.  One where we’re reaching out to people to do, like for partners to do webinars, just some sort of promotion, and so that’s, you know, a very organic process, and we’re going to spend a lot of time to figure out, okay, here’s this person we’re trying to get to, who do we know that could introduce us, you know, in what ways are we connected?  And then the other side would be, you know, kind of the outreach.  So we’ll … we’ll just put lists together of, okay, all of the top paleo recipe bloggers.  So we’ll get really, really narrow in who we target, and then we’ll put together a list of 30 or 40 of them, send an individual email to each person, and then everybody who responds, you know, we’ll try to get on a call with them and tell them about ConvertKit and go from there.  So that’s … that’s what I used to do, and now, they handle all of that.

Tara:  Fantastic.  Awesome.  So what’s next for you and ConvertKit?

Nathan:  We’re going to build this company up to the size of like a MailChimp or a Campaign Monitor, or you know, any of these companies.  We’re going to try to do it with, you know, a small, very effective team, and my whole mission is just … I learned a few years ago that if you … going back to the beginning of the conversation, if you teach, you can build this audience online and you can make a full-time living just from writing a blog and, you know, sharing this valuable, whether training, your stories, or whatever else with your audience, and so my mission is to get thousands and thousands of more people doing that, and I want to do that through ConvertKit, and so yeah, what’s next is to just keep teaching and training and building tools to make it easier for people to make their living on the internet.

Tara:  Oh, that’s so good.  Nathan Barry, thank you so much for joining me.

Nathan:  Thanks for having me.

Tara:  You can learn more about ConvertKit at or by reading my full review at  Next week, I’ll sit down with Lori Allen, the director of Great Escape Publishing, about her entrepreneurial journey, including helping the direct response marketing company she works for take their snail mail efforts online.  We also discussed the different types of offers Great Escape creates and why they create them, her process for creating compelling ads and copy, and the surprising thing she’s learned helping retirees acquire a new set of skills.

Are you surrounded by the right people to help your business succeed?  Your support network has a huge impact on your success, your satisfaction, and your ability to achieve your goals.  At the Quiet Power Strategy Lab, we get you and your business.  We respect your individuality, and we challenge you.  The Lab is our entrepreneurial resource library and support community.  It’s full of smart, experienced, and savvy business owners who want to help you succeed.  Start your free, 10-day, all access trial by going to

That’s it for this week’s episode of Profit. Power. Pursuit.  You can download other episodes of this podcast and subscribe in the iTunes store.  If you enjoy what you heard, we appreciate your reviews and recommendations because they help us reach as many emerging entrepreneurs as possible.  Our theme song was written by Daniel Peterson who also edited this episode.  Our audio engineer was Jaime Blake.  This episode was produced by Elizabeth Madariaga.  You can catch up on older episodes in the iTunes store, where new episodes are added every week, and you can learn more by going to

Photo of Nathan by Armosa Studios

Business versus Startup, Managers versus Entrepreneurs

Is your venture a business or a startup?
Are you a manager or an entrepreneur?

Think it’s all semantics? It might be. But it also might be the source of a lot of tension in your day-to-day operations.

Quick Quiz

  1. Do you make time for creating & investigating new ideas? Yes or No
  2. Would you prefer to spend most of your business time working for your clients/customers? Yes or No
  3. Does evolving & changing your business excite & energize you? Yes or No
  4. Do you prefer getting it right & sticking with it? Yes or No

If you answered “yes” to questions 1 & 3, you’re the entrepreneur-type. If you answered “yes” to question 2 & 4, you’re the manager-type.

Entrepreneurs & Startups

A startup is a human institution designed to deliver a new product or service under conditions of extreme uncertainty.
Eric Ries, author of The Lean Startup

Entrepreneurs thrive in environments of uncertainty. Change is a constant – and welcome – companion for these business adventurers. They are on a quest to discover and rediscover a product that creates value, innovation that disrupts a market, and a business that “works.”

Entrepreneurs create & run startups. Startups are businesses driven by the hunt for an unknown prey. Startups must be built for agility. One or 10 wrong moves won’t kill a startup but moving too slowly will. A startup is focused on implementing then learning and then implementing and learning again.

If you’re an entrepreneur running a startup, you probably thrive on short-term projects, experimentation, and learning new techniques.

To do: Make time in your schedule every week for thinking on, designing for, and playing at something new. Don’t succumb to guilt because you’re not spending time hustling for new clients or working on the things that pay the bills. Yes, that’s important but, if you don’t indulge your creative/innovative side, you’ll lose interest in your venture.

Also, be prepared to bring others onto your team quickly, you’ll need support in administration & management to grow the business beyond its initial stages.

Watch out for: Boredom. Recognize that many businesses aren’t meant to remain startups forever. It’s possible for you to get to a point where your desire to create & innovate in your current venture withers away. If you sense this is a possibility, be sure to be building your business so that you can step away from it, either by putting management in place or by selling it.

Also, be mindful of shiny things. Shiny things are projects or ideas that take you away from your true purpose. Novelty is important to you and should be considered carefully but not at the expense of the learning cycle you’re in.

Managers & Businesses

…you switch from riding the rocket to playing the long patient game. You’ve reached a level of business expertise and positioning such that the only way you’re going to get better is to focus on the long game of expertise and market share.
— Charlie Gilkey, Productive Flourishing

Charlie’s series on the stages of business is helpful for both manager-types & entrepreneur-types but especially so for managers.

Managers are focused on greatness. They prefer getting things right the first time and then slowly optimizing from there. They bank on the long tail. They thrive in long-term relationships with customers & clients. Their businesses are powerhouses of word-of-mouth sales. They learn and then implement.

Managers run & maintain businesses. A business is an enterprise with a proven model. It runs like a top. As long as it’s spinning, it’s generating profit.

If you’re a manager, you probably live for doing the work you created your business to do in systems that help you do that work better.

To do: Indulge two of your strengths and create a system for gathering referrals. Incorporate it into your client emails or create marketing geared at existing customers. Make sure your team knows referrals are a priority for you.

Also, reach out to 3rd party perspectives on a regular basis. A business coach, copywriter, or PR specialist might help you see opportunities that would have otherwise been missed.

Watch out for: Getting comfortable. It’s easy to get comfortable cruising along when you’re a seasoned manager and your business is working. But surprises do come. Make a habit of considering different scenarios (both positive & negative) to train or brain to embrace the unknown.

Also, look for opportunities to leverage your (or your team’s) time. When you love the work that you do and create a business for that express purpose, it’s very easy to get comfortable doing that work on a pay-for-play basis. You get paid when you work. It’s difficult to create freedom in a business like this so make time to work out ways to leverage what you do to generate profit.

What does it all mean?

Ventures that succeed over the long haul need both types of people — or more specifically both skill sets. This isn’t a judgement call; there is no better or worse. Understanding what energizes & strengthens you helps you understand how you can serve your own business best.

To begin, grow, or change direction, you’ll need to call on your entrepreneurial skill set. If this is where you thrive, you’re pretty well set. If this is what causes you some pain, get help. To maintain a low-stress business, you’ll need to call on your managerial skill set. If this is where you thrive, again, you’re pretty well set. If this is what causes you some pain, get help.

Running a business is not a solo act. Whether you’re a solo entrepreneur or the focal point of a team, it’s important to realize that there are multiple roles required for keeping your business running smoothly. Neglect a role and you’ll suffer for it.

So tell me – what are you: an entrepreneur or a manager? Answer in the comments and/or click here to tweet it!