Shopify: Kill “Deal Lethargy” With Agile Business Development

How do you use Agile Business Development to grow your business?

Harley Finkelstein is the chief platform officer at Shopify, which allows individuals and businesses to create online stores. Last time he was here, he taught the basics of Agile Business Development. The interview was so popular, that I invited him back for more details.

Harley Finkelstein

Harley Finkelstein


Harley Finkelstein is the CPO at Shopify, which allows individuals and businesses to create online stores.

Photos of the Shopify office


Full Interview Transcript

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All right. Let’s get started. Hey, everyone. My name is Andrew Warner. I’m the founder of, home of the ambitious upstart. How do you use agile business development to grow your business? Harley Finkelstein is the Chief Platform Officer at Shopify, which allows individuals and businesses to create online stores. Last time he was here he taught the basics of agile business development. That interview was so popular that I invited him back here to talk in more depth and give you more specifics on you. You can implement it if you’re doing business development at your business. Harley, welcome. Thanks for doing this.

Harley: Andrew, it’s always a pleasure to be here. I’m a big fan of Mixergy and of yours so it’s always a pleasure.

Andrew: What’s the problem that agile business development is solving?

Harley: Unlike other aspects of running a business, it seems that BD is something that takes a very long time, can get very, very complicated and, often, there is no light at the end of the tunnel. That causes what I’ve referred to in your show as deal lethargy. I think agile BD is a way and a set of principles to more forward and get past that deal lethargy. And, hopefully, you close some deals and make some money and add some real value.

Andrew: I know sales. A lot of people confuse business development and sales. I know sales is what happens if you go to a Shopify store and you buy a moose head, which is what you’ve got over your shoulder and you told me you bought that in a Shopify store. Or it’s Mixergy Premium where people buy. How is business development different? Can you describe it when it’s done right for people in the audience?

Harley: Sure. For me, business development is really more elegant sales. Rather than me selling one particular end user, I’m selling an intermediary or I’m selling a partner that can then go ahead and sell to the end users. So, as opposed to doing one deal that brings me one particular end user, I can do a deal that brings me 50, 100, 1,000 end users. I love BD. I think BD is a way where you can get sophisticated and a little more creative than you can with sales, where sales are really more binary. There’s a lot of complications, a lot of interesting things you can do with agile BD and BD in general.

Andrew: I’ve got the nine tactics that you’re going to be talking about here in this interview. You first wanted to do a quick summary of what we’ve discussed in the previous interview for anyone who missed it. Is that right?

Harley: Yeah. I want to give a background on where this whole concept of agile BD comes from. It comes from the fact that I joined Shopify a couple years ago and Shopify is a company that is very much engineer-centric. It’s all about writing great product and great code. I read something called, basically, the ‘Agile Software Developer Manifesto’. It talked about things like Itero[?] processes and collaboration between self-forming, cross-functional teams, frequent re-prioritization and testing. I found it to be very compelling because it took something very complicated, like software development, and provided a practice or course of action which they do in a very effective way. When I came over here and I watched the way the software guys were doing it, I felt that this might help myself in closing business deals and that’s kind of the background of it and that’s kind of where it comes from.

Andrew: OK. All right. What’s the first thing that we need to understand about doing bizdev right, doing it the agile way?

Harley: Sure. Again, in the same way that software development and agile software development may look the same to someone who’s not a software developer, I think to a non-BD guy, all BD kind of sounds the same and someone calling you with a deal, you’re not real sure if it makes sense or not. You’re willing to hear them out. I think agile BD is different because it utilizes the same principles that makes other agile software development so unique. Things like agile, things like pivoting a lot, the idea that dumb is better than perfect, listening rather than simply shooting from the hip, shooting bullets instead of shooting bazookas right away, so being a bit of a sharpshooter rather than being a bazooka shooter.

So, today what I’d like to do is talk about nine tactics that I’m using on a daily basis with my team here and we developed this in the last 18 months or so and I think what these tactics do is make business development a lot easier, makes it a lot simpler, and I think it cuts down on that deal lethargia that is just so common now for BD and business development deals.

Andrew: By the way, what’s the purpose of you coming here and doing this? You obviously put a lot of work into this. I’ve already said that you had a idea of how we should start, I’ve got an outline here that our researchers didn’t put together, you put this together and you emailed us which is unusual for us. Usually, we have to convince people to have to spend some time with us prepping to do it.

I’m wondering, you’re still at Shopify. Why not build out the business using your business development methods and then build it up as big as possible, and later on, come back after you guys have sold the business or after you guys are comfortable on an island somewhere and say, hey, you know what, let’s tell you what we just did. Here’s how we really did it and then reveal it. Why go through all this now? Why do a second interview on this topic?

Harley: So, first of all, I believe in collaboration. I think this is non-competitive. My ability to convey my own notes from my own sort of best practices on BD is not a competitive thing for me, it’s collegial and I want to help others that are doing it.

But I do think the main reason is, I think I’ve found something here that just works really, really well and I think that’s it’s something, I mean this isn’t rocket science. There are people that can figure out similar tactics, but I think that I’ve articulated it in a way that you can kind of follow step-by-step and get to a point where you can actually do it on your own. Again, I don’t think this is a law. I think this is maybe some guiding principles and you can supplement it and I encourage all those people watching this that do deals and are in business development to add their own sort of flavor to this sort of thing.

But really, my rationale is I found something that works really well, I want to share with everyone. Hopefully, that can add value to them. And I think also that business development needs a bit of a refresher because the way it’s been done for the last 30 years is kind of boring and uninspiring and I think the way we do it here and the way I hope others will do it after hearing this is creative and different and unique. That’s kind of what I’m trying to convey.

Andrew: All right. Here are some of the ideas that we are going to be talking about. We’re going to talk about how to be greedy, a certain kind of greedy you want people in the audience to be, how to express what you really feel and quit trying to mask it and you’ll talk about that. We’re also going to talk about rejection, how there’s going to be rejections and what you do with those. You’re going to talk about an idea you had from Steve Jobs. We’re going to talk about prep work. Obviously, you’ve done it here and how to do it right. And we’re going to tell some stories about people whom the audience knows, some past interviewees and how you at Shopify have done business development deals with them, some famous people that the audience will recognize. Do you want to start with the first tactic?

Harley: Absolutely. The first tactic is candid objectives. Very simple terms, very simple to understand; what are you looking for, what do you need, what is the actual objective of the call/of the meeting. And one of the things that I started doing about a year ago was really beginning every single phone call and every single meeting saying, “Just so we’re clear. You’re a very important person. I’m less important, but you’re important. How can I make sure I’m not wasting your time here? What can I do that allows me to be as productive and effective in this meeting as possible?” And so I will literally just say, “Look, here’s my objective for this meeting. I want to explore a possibility of a partnership or I’d like to know potentially if your demographic or your user base can benefit from using Shopify in some way. That’s what I want. What do you want out of this?”

And, I know, the first couple of times I did it, it seemed a little bit awkward but the fact that I started a meeting not by necessarily saying/giving this whole pitch, “Shopify is wonderful and you’re wonderful and everybody’s wonderful” but just be being very candid and what’s actually happened through that process is people have actually called me back or emailed me after the meeting and said, “That was the most efficient 20 minute meeting we’ve ever had.” So, again, all I do is very bluntly and candidly say at the beginning of the phone call or the meeting “Here’s my objective. What is yours?” I find that it works really well. The awkwardness that happened at the beginning is no longer there. When someone gives me a weird look and says ‘Really?’ Gary Vaynerchuk talks about the 19-year-old boy who tries to close on the first date with the girl. People want to be wooed a little but. But I think asking for the objective up front actually doesn’t prevent you from being wooed. I just think it’s a really positive way to be extremely transparent.

Andrew: I wish everybody did this at every phone call. I love talking to the audience, but there’s a certain kind of phone call that frustrates me to no end where someone gets on the phone with me and they say things, like, this is what one guy said. He said “Andrew, I built up this website. It took me a long time to build it and you’re going to love it because I used exactly the ideas that I heard on Mixergy and, here, let me show you what it does, well, let me show you first how I thought it through.” Your eyes are going to fall asleep if I continue the way that he continued with me.

Finally at the end, I said, after I think we were 10 minutes into a 15 minute conversation, I said “What can I do to help you here?” And he said “I’m not getting anyone to register for my emails. I’m not getting anyone to sign up.” I said “Oh, because I don’t see where I would sign up. I would like to join just to keep an eye on you and use my back-up email address to see what you’re up to but I don’t see where to stick it.” He said “Ah. OK. Now how do I do that?” Then I showed him that if he goes to Theme Forest he can get a quick page that would allow him to collect emails, etcetera. But people don’t do that. I don’t know where the conversation’s going and how I can be useful. So you’re saying business development calls start off with an objective. Maybe it’s exploring possibilities, maybe it’s closing a deal. Whatever it is, you’re very candid about it.

Harley: You can say that. You can say “Look, my objective is just to explore whether or not this makes sense. Does one plus one equal three here or not? If it does, then I’m sorry to waste your time.” I just think it’s a much better way to do it. It’s not just a one-way objective. It is “Here’s my objective. What is your objective?” I think if you miss that second part, that’s when it becomes a bit of a monologue and that’s not good either. It is making sure that they understand what you want and you completely understand what they want. I think that cuts down on tons of meetings and tons of BS and it gets right to the point.

Actually, Toby, our CO, does something that I love. He gets these emails when people say “Hey, I have got this great idea. I think it’s of a huge value”. He’ll think about it for a second and if he doesn’t immediately see the value for him, he may write back and say “I see the value for you, but where’s the value for me?” He doesn’t mean it in a negative way at all. In fact, it’s very constructive and very supportive. But what that does, is right away, he gets to the point of it. He’s taking his own take on this kind of idea of candid objectives.

Andrew: I love that. Best of all, now when I tell people that I need the objective for the call I can say ‘One of the things that I learned from Harley of Shopify is that we can make this call really productive if we both know what our objectives are. Here is mine. What’s yours?’

Harley: People are busy, right? Particularly if you’re dealing with higher-up executives at companies that are decision makers. They don’t have three hours to spend. What’s the deal? Tell me what it is. Let’s move on.

Andrew: I learned, by the way, from a persuasion expert here on Mixergy that if you put the ideas in other people’s mouths and not yours, then the person who is listening is much more likely to believe it. So if I say ‘Hey, you need to give me your objective or else this will be a waste of call’, they’ll think maybe Andrew’s a little grouchy. But if I say ‘What I learned from Harley of Shopify is’ then they start to think this has credibility. He’s now quoting an expert.

Harley: Exactly.

Andrew: Candidate objectives. Anything else we need to talk about in that topic before we move on?

Harley: I think that’s really good. No. I think that does it.

Andrew: All right. Let’s hit the next one.

Harley: The next one is, the number two tactic is, centerpiece. This isn’t a buzz word. I call it the centerpiece because a centerpiece is something that you have at the center of the table and everyone sits around it and it’s pretty and makes everyone feel good. It’s usually flowers or what have you. I think there’s something about finding a centerpiece between two individuals or two companies that really makes sense. Andrew, you know a little bit about Shopify’s Build A Business contest. We’ve done this now for two years. It’s been really successful for us. It’s really, really exciting. Year one, we had this really amazing mentor and adviser participate named Tim Ferriss. Year two we wanted to get some more mentors and really double down on the educational side of the competition.

Andrew: Who got to compete and what were they trying to do in the competition?

Harley: Sure. I should have given the background. So, the Build A Business contest is a contest where people that don’t currently have a business will start a business by virtue of the contest. They will build a store on Shopify. Over six to eight months, we’ll provide them with tons of mentorship and education and info sharing and best practices. In the end, we will measure who has the highest revenue and the person with the highest revenue will get $100,000 and send them to meet Seth Godin for lunch and Gary Vaynerchuk for a power session. Dinner with Tim Ferriss in San Francisco. So the first conference was great, happened in 2010 and the winner was Dodo Case, an amazing company out of San Francisco.

Andrew: I envy them, great story. These are guys who were in Y Combinator, one of the founders was in Y Combinator, the idea didn’t go so well for him, he went out and said you know what? I’m just going to go all old school. Instead of building a new software online, I’m going to create this beautiful looking case that anyone can stick their iPad into, it’ll be handmade, it will look beautiful like a book, like moleskin. I think I’m actually mispronouncing it, I think it’s pronounced mole-skein.

Harley: I call it moleskin, too.

Andrew: Yeah, so he did that, and I think he did a million dollars in sales? He was the winner of that contest.

Harley: So, they won the first contest. I think within a year after the contest they were poised to do something like $4 million a year in sales. It was just incredible. And so we want to do another contest but this time instead of giving away a hundred thousand we want to give away half a million bucks.

Andrew: OK.

Harley: We felt that the contest necessitated that sort of moving up a little bit, you know stepping it up. We want to have more than one mentor. We felt that, obviously Tim was super busy, he can’t mentor every contestant by himself. We need two more people that we thought would sort of create this trifecta of like, brilliant mentors. And we decided that the best way to do it was to ask ourselves who we would want to be mentored by. And for us it was someone named Seth Godin, someone named Gary Vaynerchuk, who are both sort of heroes of ours and two people that we’ve gotten to know quite well. And I know you know both those guys quite well too. The problem was Seth Godin and Seth Vaynerchuk are superstars and they’re super, super popular and they write books and they tour and they speak. Getting their attention is very, very difficult.

And so what I thought about was, all right, if I cold called them or I simple cold emailed them, I’m probably not going to get them directly. I’m going to get an assistant or something and the likelihood of them actually doing something with us was probably going to be quite low. What I figured out was, I needed to do some research on Gary and Seth first, the same way that we kind of got to know Tim a little bit. And just to take a step back, Tim’s four hour work week played really well into what Shopify is doing in that we encourage people to build these businesses really simply and create these lifestyle businesses in many cases.

So, for Seth and for Gary what we did was we took a step back and kind of looked, broad overview, what do these guys do, what do they speak about, what are they interested in? And it turned out, and we did it for some others but those were kind of our favorites, it turned out that both of them were about to release books around the time where we wanted to sort of begin this dialogue. And Seth’s book was called “Poke the Box”, Gary’s box was “Thank You Economy”. And I was able to get sort of snippets of these books on the web, wasn’t able to read the full book before it was released, but I was able to read snippets and substantiate to myself that in both cases the themes and sort of the central core of their book or of their message was around entrepreneurship, this new age entrepreneurship, getting out there and just doing it in the case of “Poke the Box”, making sure you have outrageous customer service in a very positive way, in the case of Gary. It all really made sense and came together well in terms of what we were doing.

And so, rather than cold email them I just reached out to them in a very friendly, non pushy way and said, just so you guys know I read snippets of your book, I think it ties it really, really well to what we’re doing with the contest. Would you be interested in discussing it a little bit? The centerpiece was this, both of them were about to release a book pretty soon after that, that was about the same theme as the launch of our contest. It made sense for them, or at least it made sense for them to at least have a phone call with me to see what I was all about, whether or not there was some value for them to add.

And so, the centerpiece in both the case of Seth and the case of Gary was really around their books and this push for entrepreneurship. It’s the democratization of entrepreneurship, get out there and do it, kill it on customer service, give you customers way more than they need. I think “Thank You Economy” does a great job of giving some examples. And once we substantiated that we were all kind of on the same level, that’s when we were able to start negotiating and figuring out how we can work together. And I think if I hadn’t had that centerpiece being their theme of their books and the theme of our contest, I never would have been able to close deals with them to come on and be our mentors.

Andrew: OK. So the centerpiece that we’re finding with the people we want to do business development deals with is that theme that we both share. The theme of the partnership.

Harley: Yeah. So, it doesn’t actually have to be a theme necessarily, in our case it was a theme of our contest and the theme of their book. In some cases, you know, if I want to go, we have a really robust app store here at Shopify and we have app developers that email us all the time asking if we can publish their app or give their app some love in our app store. The ones that actually are most successful do some research, they go to the Shopify forums, they figure out what the biggest pain points are for Shopify customers and then they email me and say by the way, here’s a clip, here’s something from your forms, here’s a quote from your forms about a Shopify customer complaining that you don’t have this. Just so you know, this is what I want to build.

Now that is a centerpiece, I can rally around it together. It’s not abstract. It’s not pie in the sky idea. It’s I have a problem or I have a common challenge that you do. I’m going to help you solve it. I think the centerpiece, is super important. I don’t think enough people look at that before trying to make a deal and try to negotiate.

Andrew: I think I’ve got an example of this in action. Amit Kumar, who is one of the guys who teaches a course on Mixergy, said that he had a company called Lexity. They help small businesses buy ads and get customers online.

And he wanted to do business with you, guys, because he needed a way to get customers from South and he know that he couldn’t just go off one at a time and get customers the way other businesses do. He needed help getting those customers.

So he said “I’m going to partner with Shopify”, and I guess what he did, he saw that your shop owners needed to get customers themselves using Google ads. You know this business and I think maybe even Facebook ads and so that’s what he made as a centerpiece. He said ‘Look, your customers have this issue of trying to get customers from Google. I’ve got the solution. I’m going to come and help you do it.’

Harley: Precisely. So again, if I that day I got 50 emails from all the different app developers that actually want to be published in Shopify ads and get exposed to our 21,000, 22,000 active merchants. Here’s a guy who I couldn’t say no to because he was satisfying a challenge for me. There was someone that having a problem with, he knew that and he was just, and so Lexity is a great app and really popular and has done super well and I never had any concerns with putting it front and center in the app store because there was a common centerpiece. He was trying to take away one of my pains, which was driving more traffic and merchant sites.

And so I think that’s really compelling and that’s a great example of doing that. I also want to say that we’ve been talking a little bit about corporate centerpieces. There are also personal centerpieces. And I think that’s also really interesting. When you are dealing with guys like Seth and Gary and Tim, their corporate centerpieces and their personal centerpieces are basically the same.

Tim is all about the 4-hour brand and so that’s fantastic but when you’re working with a larger company, for example, one of the things I like to do before a meeting is go to LinkedIn, just Google the person I’m meeting with, check out what they’ve done. I used to wrestle in high school. If I can find that one of this guys used to wrestle, I can have a conversation about, are you into Greco-roman wrestling? Was it Free-Style wrestling? I’m also a skier, maybe these guys have skied in Salt Lake City or maybe they’ve gone to Tahoe and then we can talk about that. I think having even a centerpiece interest also breaks down a lot of the barriers.

Universities, for example, is an amazing centerpiece because people are traditionally very loyal and very excited about where they went to school, their Alma Matters and so I went to McGill University. When I found out that somebody went to McGill, one of the first things I would say is ‘So, where’d you live the first yea? Did you live in [??]? Did you live in a dorm?’ and that kind of sets the tone really, really nicely. Again, I don’t think you should go down that path too much but I think there is a difference between corporate centerpiece and personal centerpieces.

Andrew: I see. OK. All right. So we’re looking for at least one of those two. At least some connection that I have with the person who I’m about to do a business deal with, or at least one connection that our two companies have, the one thing that they have in common.

Let’s go to one more and then I am going to ask you to tilt that camera up to see what it is that is over your head but what’s the next one?

Harley: Sure, so one of the things that sort of fits really well with this idea of a centerpiece is a proof of concept. This is not my phrase. Anyone who’s done an MBA or who’s out of business but knows about the idea of a proof of concept. MVP might be another way to put it, Minimal Viable Product.

In software development, you talk about MVP and proof of concepts, shoot a bullet, see how it goes. If it landed beautifully and exactly where you want it, then you shoot a bazooka.

With [??], I think it’s also important to do a proof of concept and sort of start small. Even in the case of the contest, the build a business contest, our first engagement with Tim was very, very small in terms of how much money we were giving away. Tim’s full commitment. We just kind of didn’t know what it was and if we were to push too hard, I think we probably would have turned someone like Tim Farris off about the whole thing because he doesn’t want to be involved with people that don’t really know what they’ re doing and are kind of sloppy.

And so we sort of crawled before we walked, we crawled before we ran, I think all too often in a business development deal, everyone’s shooting for the stars. They want to do a huge deal with Facebook or Google or Twitter and if it’s not the biggest deal, it’s failure. Frankly, going to a Twitter hack fest or going to a Twilio hack fest, [??] hack fest and as a developer or as a business guy and building an app collaboratively with them on a Saturday morning so they can get to know you a little bit. That makes it much easier later on to do a bigger deal.

We have a big deal with an international shipping company and I wanted to do a very large, substantial deal. I was going to wear it on my shoulder like a certificate or an Army sergeant’s badge. But I couldn’t get to that point. I had to take a couple steps first. I started very, very small. I started offering their services to our merchants at a discount. Not as a re-seller, not as an affiliate. Just as a “Hey, I’ve got a lot of merchants, you have a good shipping product. Let me just offer you to them.” I found that by going through that particular course of action, it was always much easier to do the big home run in the end. More times than not, the deals that have been home runs have started with a bit of a crawl before we ran. I think the idea of proof of concept goes far being just product and goes far beyond just software development. I think you can do proof of concept in a business deal, too.

Andrew: What happens if in a business deal, you do something like what you did, which is just refer your customers to this partner, who’s not a partner. Just refer your customers to this company that you hope to partner with. And when you come back to them and say ‘Hey, look, our customers love this. We should have a more detailed or deeper relationship’ and they say “No, we like it the way things are right now. Keep linking, keep sending people to us”. Have you lost a deal because you gave up too much?

Harley: That’s certainly a risk. But the truth is, a partnership, even with these large companies, even if you’re working with the most hegemonic company in the world, an IBM, let’s say, you’re still dealing with people. In the anecdote you’ve just provided, I’m not sure I want to do business with someone like that. If they can make a lot of money from me on a small deal, imagine what we can do together in a much bigger deal. It is also a good indication of the type of personalities and characters you’re dealing with. If they’re trying to screw you in some ways or they’re trying to low-ball you on a small deal, just imagine when the magnitude increases tenfold to millions of dollars. It’s a really good indication of the type of characters you’re working with.

Andrew: All right. Let’s take a look at that. What is it over your shoulder?

Harley: OK. Shopify just moved into a new office. A beautiful space. I’ll do a tour maybe with my iPhone and send it to you. But what we tried to do is outfit our offices with Shopify store products. I’m going to move this around. This is my moose that I have. Right in back of me. It has a mustache on it and it’s really cool. I’ll try after we’re done here to show you some other stuff in the office but this is my cardboard moose.

Andrew: I see. A cardboard moose head with a mustache over your shoulder.

Harley: It’s my moose-tache.

Andrew: I always try to look over people’s shoulders to get a sense of what’s in the office, what’s on their desk, what are they working on. If it’s a whiteboard my eyes will bleed before I stop trying to read what’s on there.

Harley: In every office at Shopify there’s one wall that’s colored so I got lime green and I put it behind me. My whiteboard is on that side so I can stare at it while I’m at the computer. There’s this really great Tumblr blog called “Everyday Carry.” It’s basically where people can take out what’s in their pockets, put it on a counter, take a picture of it.

Andrew: Oh, cool.

Harley: I find something about that so fascinating. Seeing the way someone has their desk set up, I find that really fascinating.

Andrew: All right. I also want to ask you about what’s on your arm but let’s do three more and then we’ll come back to that.

Harley: OK.

Andrew: We talked about tentative objectives, centerpiece, proof of concept. What about schedule?

Harley: Yeah. I want to talk about schedule now. Schedule also relates to all these sub-categories of centerpiece. If you recall, in the anecdote I gave you with Gary and Tim and trying to get them engaged, I was really fortunate that the timing made sense. The truth is that if the timing didn’t make sense, if I was launching my contest in May and they were launching their books in August, I probably would have waited until August to do it because those are two people that really played a huge role in our contest and really helped us promote it.

Andrew: You would have rearranged your contest around their schedule if it was a few months off?

Harley: Absolutely. Without question. Now, again, the reason I would do this is because I know that these guys are really busy. I want to make sure that it’s convenient for them. The worst thing you can do is force somebody into a business development deal. If they’re forced into it, it’s not going to be any fun for them. They’re not going to give it their all. I want partners that are completely into this and if they’re not into it, tell me and certainly I can try to rearrange it in some way that makes it more enticing. I think schedule is really, really important. When you’re doing these centerpieces, it’s important to figure out ‘Is that partner launching a book?’ I just heard that PayPal just recently launched a new card reader to compete with Square. If I was going to do a deal with retailers around PayPal, I should probably do my research. I should know that this past week they did this launch. I’m not going to go to them six months ago and start asking them about their card reader, knowing that that’s still six months away from development.

I spent a lot of time diarizing, using my calendar, my iCal, figuring out when launches are happening, when books are coming out. We’re doing a deal right now. An awesome deal with Daymond John who is one of the sharks from ‘Shark Tank’ and we timed this deal with Daymond perfectly around the schedule of ‘The Shark Tank’ episodes on TV because they happen Friday nights and we want to make sure that we do it properly. Had I pushed too hard on someone like Daymond, who is the founder of FUBU, a total maverick, amazing businessman, super successful, I probably would have blown it. I really tried hard to figure out what his schedule was for season two and season three of his show. It’s very difficult to do that when you’re not in the studio.

But there is a method to the madness. There’s a calculation you can do. So I actually spent time figuring out when the show was going to air based on last year’s precedent, based on how many episodes in a particular season. One of the reasons I think we were fortunate to get Daymond John was the timing simply lined up and I think that’s something that people don’t realize. Again, going back to that [?] analogy of that 19-year-old dude that wants to close on the first date, it’s not going to happen. That’s short-term thinking. I think you have to be mindful of people’s schedules and what they’re doing and what they’re launching. Again, that fits back to the whole centerpiece. What are they interested in?

Andrew: I found that even with interviews, that people who are impossible or feel impossible to get on as guests, when they’re at a certain time in their lives they’re eager to do the interview. They’re eager to come on and be guests. Those times are when they release a new product and they’re eager for the world to know about it and for sites to link to them when they’ve got a new book and it’s time to do publicity and they can add you to their list. I see the same thing with business development. When there are certain moments in people’s schedules when they’re ripe to do a deal, you’ve got to jump on those. You’ve got to anticipate them and that’s what you’re saying to us.

Harley: I couldn’t agree more. Exactly.

Andrew: All right. Next, this is the one where I was mentioning something about greedy. What kind of greedy do you want us to be?

Harley: For some reason, post-Wall Street Gordon Gecko 1980s culture, greed became this bad thing. I think short-term greed is a really bad thing. I think long-term greed can be really helpful and can be something that’s very motivating. Let me tell you what I mean by long-term greed. I’m going to use another example here because I think it does the point really well. Shopify has over 1,000 partners. We call them partners. Most of them are design shops all over the world that when someone walks into the design shop and they say “Hey, I want an e-commerce site” they come and they build it on Shopify. Those designers love working with Shopify and we love working with those designers and we have a deal in place with them so they get properly compensated.

One of the things that happens from time to time is we start asking through surveys and certainly on the sign up process “How did you hear about Shopify? How did you get to us?” We do some multi-attribution to figure out what the course was from Googling ecommerce you get to Shopify. But often, we’ll just ask how’d you hear about us. Sometimes, ironically, what happens is we hear a name over and over again that isn’t a registered partner. Someone who is just referring businesses to Shopify. It might be a really cool e-commerce blog, it might be a partner who runs a design agency in New Zealand. Often, we’re surprised to hear that “Wait a second. That guy David from New Zealand is sending us, like, 20 stores? Who is David? We never even heard about this guy.”

I think a lot of companies would probably just send David either a thank you note or nothing, actually. Just wait for David to continue sending orders his way. What we do, actually, is very, very different. I will call David or someone on our partners end will call David in New Zealand. This is fictitious, but you get the example. We’ll call David and say “Look, David, what you’ve been doing is amazing. Did you know that we have a partner account where you actually get a revenue share from people you refer to us?” And he’ll say “No, actually. I had no idea. I love Shopify, it’s a great product. That’s why I use it.”

What we’ll do in many cases is we’ll retroactively comp him all the accounts he’s brought to us prior to that negotiation, which I think is really unique. Often, the reaction from the David of the world where we say we’re going to retroactively apply a rev share, he’s blown away by it. What company is going to give me money that I actually never earned? That’s kind of our way of paying it forward. It’s our long-term greedy strategy.

I can assure you that even though it may cost me a couple hundred dollars or couple thousand dollars to compensate David on the retroactive accounts he sent to us, the truth is, David’s going to be a loyal partner for us for the next fifty years and that is so much more important than the $5,00 or $10,00 or $300 that I was going to pay him. We don’t simply wait for people to ask for the money. If they’re bringing us business, bringing us value, we’re going to pay them. Often, we will even retroactively pay them out of our pocket.

Andrew: Yeah, that’s a tough one to sell to an entrepreneur who is just scraping by and getting his business going. But it’s an investment in a long-term relationship with the businesses.

Harley: Totally.

Andrew: All right. Next, productivity.

Harley: I work in an environment where it’s mostly engineers. I work with probably some of the smartest engineers and programmers. We recently hung out with Toby and Daniel in Austin.

Andrew: You and I did, yeah.

Harley: I work with the smartest people I’ve ever met in my life, which is why I’m at Shopify because. . .

Andrew: I was asking you, actually. I said, candidly, Why did you–because you were running a business. I said, “Why did you give it up to go work at Shopify?” And you said that same thing, that you wanted to work with these guys who were just really smart.

Harley: And these guys have just–I think what Shopify is doing is really democratizing entrepreneurship. Entrepreneurship is at my core what I am. I met these guys and I was just completely taken in. It’s always really good, as we discussed at lunch, to be the dumbest guy in the room and often I am. I feel really, really good about that.

Andrew: I feel insecure when I’m like that.

Harley: Yeah. I am actually quite flattered that these guys allow me to hang out here and help them with the business side of Shopify. But I work with some really smart engineers and programmers. What I’ve realized–and no one’s articulated this as well as Paul Graham has done–what I’ve realized is their work schedule is very, very different than mine. I can do 20 meetings in a day, 20 minutes each or half hour each, bang them out; one, two, three, four.

And then, in the evenings at a spin class or yoga class I’ll do some deep thinking and go home and write a little bit about what I want to do the next day. But programmers can’t work in 20 minute stints. In fact, in some cases they need four hour blocks in order to do something really productive. That’s really challenging for me because as an executive here, many of my colleagues need four hour blocks and I need five minutes with them here and five minutes with them there.

And I read this amazing blog post that had a real effect on me by Paul Graham called Makers vs. Managers Schedules. What I’ve decided to do–the quick answer, it’s online on the Y Combinator blog, or Paul Graham’s blog. But the short summary is maker schedules sort of have four hour blocks. Manger schedules sort of have 30 minutes blocks. And what I’ve decided to do was because of the people I’m working with and the way they operate–and the way I operate as well–is I’ve chosen to make Monday, Wednesdays and Fridays manager’s days and Tuesdays and Thursdays makers’ days.

And so what I mean by that is I have most of my phone calls and meetings and deal-making sessions Monday, Wednesday and Friday. And Tuesdays and Thursdays, that’s kind of big thinking day. That’s where I will go–will talk to someone, perhaps one of our guys here who’s looking for a change in career. Maybe give him some mentorship. Maybe he needs some advice. That’s when I’ll conceptualize the next contest. Or I’ll figure out there’s this company that I love in the UK. I want to do a deal with them. I don’t know what it looks like. Let’s grab a spreadsheet and figure out how we can make this work for them. I’ve actually separated my time between maker and manager schedules. It’s been hugely productive for me as a BD guy who has to work with some really smart engineers. First of all, it’s a lot less irritating to them which is important. But it also keeps me really, really efficient with my own time.

Andrew: You know what, actually? I’ve started doing that and it’s a huge help. I used to–if someone wanted to have a phone call with me, I’d do it at any time. I’d just add it to my calendar. If I did interviews, I would just do one a day and it would break up my day. And as Paul Graham says in that essay that you mentioned, if you have that one thing coming up later in the day, you can’t relax and lose yourself in the work because you keep thinking I’ve got to stop and go and take the phone call. Or in my case, I have to stop and go and do the interview. Now I’m batching all of my interviews into two days, Tuesdays and Wednesdays. That’s what you and I are doing today. You’re one of the interviews for today.

And then this guy, a Mixergy premium member called T.K.[SP], the founder of [SP], he told me that he makes phone calls, all of them on the same day at around the same time. And I did that and, man, it frees up my mind when I’m not making those phone calls. So Monday, now, I have no phone calls and I can get lost in a project. So, what you do is you say you break it up into four hour blocks. You don’t even need to break it all up into one day the way I do?

Harley: No, sorry. I kind of break it down. It’s not science. It’s not always four hour blocks. Often it’ll be on Tuesdays and Thursdays it’ll be a three hour block to talk about what I want to do in terms of a channel deal with this big company. Or it’ll be a five hour block to talk about how I want to restructure my team because I have some new guys that just joined our company. But it actually–if you’re sitting in front of your computer all day and you’re on the phone all day and you’re writing all day and sending out emails all day, I find it’s not the most creative place to be.

Often I’ll just leave the office. We live in a really awesome place called the ByWard Market in Ottawa, and I’ll go to a cafe with my Moleskine or Moleskyne, or however you pronounce it, and I’ll really just write down my thoughts and I’ll spend an hour or two there. I find when I come back from that I’m a lot clearer. I have a lot less on my mind and I can really focus on the task in front of me. Everyone that joins Shopify and my team has to read The Makers and Managers Schedules. I really encourage everyone to read it. It’s such an important post because engineers and business people really don’t work in the same kind of manners. Toby is coding some nights until midnight or working on something until midnight. I’m in bed my 9:00 because I’m in the gym early in the morning. You do have to figure out a way to work well with each other even though everyone has different schedules. The makers versus managers differentiation makes a lot of sense to me.

Andrew: You know what, we have three other big ideas to cover. I wanted to look at your [arm] and I want to take a tour of the office. But you’ve got to indulge me and just take sidetrack here with me. Tell me how do you, when you take time off in the middle of the day to journal and to think things through. I get excited about that because we don’t, on a regular business day, get enough time to think through what we’re trying to do with our lives, what we’re trying to do with our business. We’re in a very reactive mode instead of creative, productive mode. I’m curious about when you take that time out with your moleskin, and I’ll pronounce it that way, what do you do? What’s your process of making that a productive thought session?

Harley: The first thing is I leave this at home.

Andrew: You leave your phone at home?

Harley: Yeah. I mean, I’m, as I’m sure you are and many of your watchers are, I’m pretty compulsive and I’m pretty obsessive. Because of that if I have my phone there I will check it every now and then when I have five seconds between the time I pour the milk into the coffee and the time I put the coffee in my mouth. If I have it there I know that I’m going to look at it.

Andrew: That’s a good point. I do that too.

Harley: The other thing that I’m finding recently is that email is becoming a task list that other people populate for me. That kind of sucks. I’m OK with the task list. I love lists. I have lists all over the place and especially with using Ever Note now. But I don’t want other people populating my task list. Initially what I did was I used to go to the cafe and bring my iPhone and I ended up checking my iPhone most of the time and answering emails there and taking phone calls. I thought that just wasn’t productive. I’m at my desk. I have my phone, I have my computer, I have everything I need here. But when I leave here I kind of want to depart from this a little bit. I want to get out of this.

Andrew: OK, so get rid of anything that’s a distraction. But once you’re faced with that plain piece of paper and it’s time to fill it up in a productive way what do you do? Do you write a list of questions that you’re going to answer?

Harley: One of the things I first of all I do every time I have a brainstorming session is I usually start with a blank piece of paper. I have a moleskin and so it’s beautiful paper and it’s great and I like to have the continuity of it. But I find that when I start halfway through a page I actually am not as creative as I want to be. I’m kind of reading up there and reading up there. I find that starting with a blank piece of paper is really, really efficient. The next thing I do is I actually spend a full 24 hours before execution I’ll write down everything I want to do or my ideas. I like to draw pictures and diagrams because I’m a very visual guy. I won’t do anything for 24 hours.

I find that 24 hours is a great reality check. It’s the same way that, you know, when I get an email from a partner or from a customer or a competitor that kind of pisses me off and I start writing a nasty email because I’m really upset. I usually don’t send those. I usually give myself 30 minutes or an hour and in the end I usually end up deleting those because they’re not productive. I’m really careful about that.

In the same way that I do that I usually give myself 24 hours to mull it over. I know you’re a big runner. I don’t run but I do yoga and I spin. When I’m on the spin bike I’m thinking about what I wrote down. All of a sudden I’m like you know what? That is a stupid idea. I’m never going to do that. Forget it. Often I have an epiphany and say OK, well that’s not a stupid idea completely. There is some merit there. Let me see where I can go with this.

The last thing I do, which I think is really helpful, is I basically put everything into Ever Note. Everything into Ever Note. I use the tag feature in Ever Note compulsively. Cafe on Tuesday might be one tag. Beautiful day outside, just so that I can kind of remember it. But I put everything into Ever Note and this way I can always reference it. I find that to be very helpful.

Andrew: You know, I put a lot of things into Ever Note too. Here’s a tip for getting your moleskin into Ever Note. There are a couple of things you could do. You could scan each page individually but here’s what I do. I go to Kinko’s and for $1 they will chop that binding off of the book, which I know will freak out some people but I love that. They will chop that binding cleanly off the book and then I use a snap scan that’s sitting right here in the office by Fujitsu. Merlin Man recommended it. I bought it, I love it. You just put it at the top. You hit a button and it scans it. It gives you a document that will go into Drop Box if you want and it will automatically import into Ever Note. All those thoughts that you came up with that maybe you can act on now, maybe you need to wait until later, are stored forever.

Harley: I think it’s amazing. You can also search inside the document even though it’s hand written. That’s amazing. I have sort of figured out ways to optimize my life. I also, in the same ways that the software guys here A/B testings. I also A/B test my own life. Right now I’m A/B testing 6:00 a.m. yoga. Which is something I think I told you when we were hanging out.

So 6:00 a.m. yoga right now is working for me. I feel great, I’m really tired in the evenings but I’m a lot calmer and a lot more collected. And it’s just something that I’m really excited about. I may not do that forever. So I do try to change things up from time to time. But there are certain staples and I really think that the makers and managers schedule is going to be a staple for me. I just, I love it.

Andrew: So, what is on your arm?

Harley: So, are you talking about the bracelet or the tattoo?

Andrew: The tattoo.

Harley: So, the tattoo which says hustle, and It’s kind of coming off because I’ve had it now for about a week. But I’m going to put it back on.

So there’s an amazing web designer, Tina Eisenberg, also known as Swiss Miss, very very famous. She runs a blog called So Tina has a younger daughter who came home from school one day with temporary tattoos all over her arm. And Tina being the most visual brilliant designer I know said that this is ridiculous, there’s no way that temporary tattoos should look this bad.

And she started calling up all of her really well known super impressive and creative designers, friends of hers. And had them each design one tattoo. And so I had a wash tattoo on that said ‘you’re late’ unfortunately it came off last night. And she basically bundled this all together around a store called, t-a-t-t.l-y. And is just basically, they call them design temporary tattoos and so yeah, the hustle one is my favorite. Because I’m always hustling and it’s just I love it.

Andrew: I was reaching my pocket to get mine. This is the one that you gave me. There’s the company that URL right there and here is the temporary tattoo you gave me at that lunch that we had at South by South. Who was that hotel by the way at South by Southwest?

Harley: Four Seasons.

Andrew: The Four Seasons. That is place to be because it took me an hour while I was waiting for you.

Harley: It’s crazy, I know that. Because you were waiting for me and yet like people don’t go there. It’s kind of too fancy for more startup guys. The problem is all the other hotels are so crowded that the startup guys have now taken over the Four Seasons and it’s awesome. Just the amount of people I got to hang out with.

Andrew: Me, too.

Harley: And sit on that couch.

Andrew: I’ve met more people at that Four Seasons lobby then I have met anywhere else. I mean, that I got to connect with then with any where else. Had a beautiful lunch which was quiet without people bumping into us. Looking out at the water.

Harley: Beautiful water.

Andrew: And I also learned this, you got me to get the Mophy.

Harley: Awesome. Yeah, isn’t the Mophy amazing?

Andrew: I love it.

Harley: I think it’s a must have for any conference goer. In fact, you get a full day extra of battery life, it’s just amazing.

Andrew: You do. Unless you have somebody like Toby next to you, who needs half of your battery life[inaudible]

Harley: Like I said when the boss needs a charge and fortunately he grabs my Mophy.

Andrew: He’s a smart man.

Harley: It’s how it goes.

Andrew: Let’s do 3 more. The last 3 in and then I want to go look at your office if you could show us some things there.

Harley: Sure. Totally.

Andrew: So next.

Harley: So, the next point I have is do your homework first. Know who you’re talking to from a corporate perspective and a personal one. And again this does apply to the centerpiece as well, the difference between this and finding a center piece is this takes a little bit more research. Whereas a centerpiece, you know, everyone knew that Gary is coming out with a book called Thank You Economy it was obvious that I would research that.

The homework piece is a little bit more in depth and this is kind of where you want to read someone’s blog. I remember when we were about to raise money for some VC funding, I’d read this great white paper from Bessemer called the Ten Laws of Sass Businesses. Really well known white paper, those of you that are in sass business should read it. But I’d looked at who wrote that white paper. I started looking at that particular person at Bessemers, their blog, their personal blog. Understanding what they do, understanding how they operate. What their passionate about.

And by the time it came, when the time came to actually meet these people in person, I felt like I knew so much about them. And I was able to say, look I read this really great post you had about why average revenue per user is a better metric than sales per customer, or something like that.

And not only does that show you’re really interested but in some cases it’s really fascinating to see what everyone is all about. So in a case if I was trying to pitch you for something, so you know, I would sort of look at the fact, hey you’re runner, I use to run too and I hit a plateau. So, maybe, one centerpiece or maybe some of the homework that I do is talked to. But hey how do you not get bored of running because for me running is become painful for me beyond the shin splints.

So, I think that doing a little bit of homework goes a really long way. And I don’t think people actually do their homework. Particularly when it comes to larger companies. Which doesn’t make sense because a lot of these publicly traded companies, you know, you can go to their corporate investor page or their corporate page and see who the executives are and just sort of work backwards. Go to LinkedIn check out their blog, see what they’re up to.

And I find that if you do the homework beforehand it gives you this great context on them. I’m doing a deal right now with a large telecommunications company and one of the executives used to work at another company that we’ve done a deal with. Had I not known that it probably would have come off that I really didn’t do much of my research but I happened to do my homework for almost every single phone call that I ever have. Because of that I was able to kind of right away say by the way, I know you used to work at this great company. I did a deal with them. Here’s how it worked. He said yeah, you know, I was hoping you’d bring that up because that deal worked really well for them and we’d like to replicate it. It shows a lot of respect for their time and a lot of respect for who they are. I think that far too many people that do BD and do sales are kind of like the 19-year-old dude who just tries to close on the first date. You’ve got to do some homework man.

Andrew: How long does it take you to do that? I know, to be honest with you, it took me in the past an hour to do research on each guest. Maybe a little bit more. I would find out those things like you’re talking about. That they were interested in running or they had this past business that failed. Then if you go in five pages in Google search results you come up with someone who didn’t like them. You get a sense of why that person didn’t like them and what they stand for that makes people upset. It took me at least an hour to do that and now I have people at Mixergy who help me, Ari and Andrea. They put research on you together. But it’s a lot of work before each meeting. How long does it take you?

Harley: That’s where, I think that’s where priorities come into play, right? There are, you know, again one of my other tactics that I use is every deal to me is gold, silver, or bronze. That has nothing to do with the quantum of the deal. Some of our biggest deals I would classify as bronze deals.

Andrew: Some of the biggest deals, you said, you’d classify as bronze?

Harley: As bronze, right. What gold, silver and bronze means to me is actually level of difficulty. How tough is it going to be to close the deal with them? We built a theme for Shopify called social which it basically embeds a lot of really great social commerce into it. It’s in the Shopify theme store. We built that theme but I felt really bad that we didn’t build that theme in collaboration with Facebook who, you know, knows more about social than anybody else. I really, really want to sort of redo the theme and rebuild it with Facebook’s input and feedback. It wasn’t going to bring us any money necessarily but that was a really important deal and I really felt that working with the Facebook commerce team was fairly difficult. That became a gold deal for me.

The flip side is we have partners of ours that send us, you know, tens of thousands of dollars, and those are often bronze deals because the level of difficulty is less. Usually for the gold deals I will do the research myself. Silver deals I have an amazing team, amazing BD team here. Brennan who’s, I think, an up and coming star at Shopify helps me with BD. He does a lot of the research for the silver stuff and certainly for the bronze stuff too. I really do prioritize that. But frankly if I was doing this by myself and we weren’t a 100 person company, it was just me, that’s where I would spend a lot of my time because I think the ROI for doing your homework is absolutely massive.

Andrew: I see. If I walked in to a meeting with you and wanted Shopify to partner up with my business I might talk to you about how at 17 you started a t-shirt company and how I might have started one back then too.

Harley: And then right away you and I have a connection immediately beyond any of the dollars and cents and profit and loss reports and rev share agreements. We have a connection. I think that’s far more important.

Andrew: All right. Next one. Steve Jobs. That’s what I was mentioning earlier at the top of the interview.

Harley: OK, so this one’s a little bit controversial only because it is somewhat, sorry. At the beginning of this talk we talked about the idea of candid objectives. Being very clear up front and saying what you want and asking what the other parties want out of the deal. In Steve Jobs’ book there was a line about how Steve never went into a meeting without knowing exactly what he wanted from that meeting. I can appreciate that and I think Steve is, obviously, far more successful than I am and maybe than I’ll ever be. There are very few entrepreneurs out there that I respect more and certainly product guys I respect more than someone like Steve Jobs.

That being said, I’m far more agile than that. There are some meetings that I don’t know what I’m going to get out of it. It’s just, as I said in the first sort of conversation…

Andrew: Interview here.

Harley: Exactly, first interview here we talked about the tickle. I do believe in the tickle. I do believe in throwing some shit out there and seeing what sticks. It doesn’t mean wasting anyone’s time it just means sometimes in terms of deals things don’t really become obvious right away. Asking for the objective up front really does help mitigate some of that but it’s still, I think the idea of being agile and being open minded to different things.

On the last interview we did I told you about someone who it kind of started as a bit of a litigious relationship. I sent them a cease and desist letter because they did something that I thought was contravening our intellectual property at Shopify. In the end, you know, a year later these guys are a great partner of ours. Had I gone in there with these are the objectives, here’s what I want, I want to sue you, you want to do this, I never would have had that opportunity. Instead I listened. I like to talk a lot so it’s tougher for someone like me to listen sometimes but I really try very, very hard to listen. Sometimes in that you can hear, in the case of this partner that we sent the cease and desist letter to, I sense that there was some empathy there.

They really put themselves in our shoes and understood why they got that cease and desist letter. And that type of empathy really made me think this is someone I might want to do business with. And had I gone in there and said look, this is all about the cease and desist letter, it’s all about intellectual property, I would have blown a very substantial deal for us. And so I do believe that, while I respect Steve Jobs and I like the fact that he went to every meeting with a clear, very clear objective of what he wanted our of it. Sometimes that initial cannon objective tactic doesn’t work, and in those cases I think it’s really important to listen and be agile and pivot as needed. Oh well I came in to talk to you about a charity I’m working on, oh you also have this company, or vice versa. Well that’s really cool, here’s what I do, I also do some mentorship for students and all of a sudden now you start building a relationship and report and that’s where things get really sexy.

Andrew: OK. So what you’re saying is the need for objective is important, walk in there knowing what you want but also be flexible enough to look at other options as they come up.

Harley: Yeah, you’re not always, you know, hopefully seventy five percent of the time you’re gonna know what your objective is and what their objective is but this idea, this sort of 8th tactic, I think there’s a twenty five percent, or at least that’s the number for us, where we actually don’t know what it is. That’s kind of what happened with Dave and John, I really didn’t know exactly what to do with him. I knew that I loved him, I knew that I was a huge fan of him, and what him and Mark Cuban were doing on Shark’s Tank and Fubu is an amazing story. But I didn’t realize that he can add so much value to the Shopify merchant selling apparel because of his great experience. And it only donned on me once we started to marinate that, so I was really agile about it. There was a centerpiece but I was agile about how I wanted to work with him. And so I think being a little bit loose can help us sometimes too.

Andrew: You know what, let me put this call out. For anyone who’s listening to us, if you’re in biz dev and you’re especially good at it, I want to start doing interviews with business development people about how they do their work. This is a really interesting.

Harley: Yes!

Andrew: Right? We should do more of this. I realize as I talk now to you that I’ve covered so many topics here including failure, from success to failure and everything in between, I thought. But I’m not covering business development enough because I think I’ve fallen into this trap of believing that social is enough for getting customers, and ad buying is enough for getting customers. And I forgot that partnerships like the one you’re talking about can, for no money often, for just reciprocal benefits, can end up sending you a ton of customers all at once. And just before you and I talked I was on Skype with Charles Hudson who is now a venture partner at Softtech but previously he was doing bis dev. And as he told me about his work and the story of how he got partnerships I though, you know what? This is not just useful, it’s fun to hear how business development gets done. So anyway I’m putting a call out there guys, I want to do more of it.

Harley: I agree, and that’s kind of where I said, for me biz dev is the favorite part of my job here, beyond you know, me being general counselor and some of the other responsibilities I have here. I love BD, I think BD is a great way for a sharp businessman to be creative and really do some really cool things. And it allows you to also kind of build on that. So you do one partnership and you kinda say, well that was pretty good, now I can actually, if that worked for a small little postal company in New Zealand, maybe this will work for USPS in the United States. And now I can show them a proof of concept saying look, here are the numbers, here’s how it worked. So I live BD and it’s something that, you know, if I didn’t have hustle on my arm I would have BD on my arm I think.

Andrew: And you know what? And you’ve thought through the process of BD in a way that I think other business development people haven’t. That’s fine guys, if you’re out there and you’ve done a lot of business development and you just want to tell us some of the stories, you don’t have to have it thought out the way that Harley did, you don’t have to have it as organized. You don’t even have to have a team the way that Harley does. I just want to hear more of those stories. I’m getting excited about this. It’s making me realize we don’t do nearly enough business development here at Mixergy and maybe that’s a reflection of my lack of appreciation of the significance of it. And that’s probably why I don’t have enough business development conversations here on Mixergy.
Alright we’ll do more.

Harley: By the way that’s the best part of Mixergy, Andrew, is the fact hat Mixergy is sort of, it’s dynamic. It’s a living tree and it evolves and stuff, that’s one of the reasons why I think your show is so great.

Andrew: Thank you. It’s surprising how much of my own, and I shouldn’t be admitting this publicly but screw it, I’ll do it, how much of my own prejudices and awareness influence the interviews that get done here and the message here. And I want to be aware of what I’m not aware of. And that’s why I want to be open about it so that other people can feel free to say, you know what Andrew? Here’s another thing that you are not recognizing and you should do it, and call me out on it so that we can make a much better program here on Mixergy. OK last big idea is…

Harley: So the last, do you want to into it or do you want me to do it?

Andrew: You tell me. Tell me about rejections. This is something that I thought was so important that I mentioned it at the top of the interview and we had people hang on I think just for this, because it’s a very serious, very painful fact of business.

Harley: So early on in my life, before Shopify, before the MBA and law school, as you mentioned earlier, I started this company selling t-shirts to universities. And we did a lot of the orientation, the first day of school stuff, and the bookstore payroll. In that process, I started…I didn’t have any mentors when I was 17 years old, other than my dad. He was a great guy, but he wasn’t able to give me the mentorship I needed, the hard skills. He was able to give me soft skills, but he didn’t give me the hard skills.

But I knew there were guys out there, guys like Dov Charney, who is the founder of American Apparel, and guys that were in the t-shirt business – Chip Wilson, who is the founder of Lululemon out of Vancouver – guys that were in the apparel business that were just so amazing and had such great stories, but I didn’t know how to reach them. And like the 19 year old kid that Gary talks about, I sent out these emails saying, “Dude, I love you. You’re amazing. I’m going to be in Vancouver”, even though I wasn’t going to be in Vancouver, “I’m going to be in Vancouver. Give me 10 minutes of your time. Please, please, please. Bye, Harley”. And that was it.

For a long time, I couldn’t figure out why I wasn’t getting any replies whatsoever. It wasn’t working out. As I got older and a little more mature, turned 20 years old, and I was an old 20 year old – I’m certainly an old 28 year old now – but was certainly an old 20 year old, I started realizing what I was doing wrong. What I didn’t do was I wasn’t giving people the ability to reject my offer in a very polite way. What I started doing was I started saying kind of the same thing, ‘I’m going to be in Vancouver’ – again, even though I’m not going to be. I’d fly there to meet this guy – “I’d love to steal 5 minutes of your time. However, I know that you are super, super busy, so I would not be offended if you can’t meet with me”.

Time and time again after doing that, people would respond saying, “You’re right, I am super busy. We’re about to go public”, or about to do this, or, you know, “I’m traveling the world, but thanks for your email”. What usually happened at that point was I would kind of diarize it for about a month or two and then write back and say, “Hey, I’m going to be back there again. Remember me?”, and right away – I shouldn’t say right away – for the most part, I would usually get an immediate response saying, “I actually am available now”.

I gave these guys a way out, a way of rejecting my offer that didn’t make them feel uncomfortable and didn’t make them feel like they were losing face. It wasn’t embarrassing for them, whereas because I was so forceful, and again, I think force and being assertive is really important in BD and business in general, but because I wasn’t overly forceful and I gave them a ticket out to say no, to decline and not make it uncomfortable, that changed everything. So, for the last 8 years or so almost every one of my reach out emails, be it to a great mentor or someone I admire, someone I want to speak to and I want to connect with, I always provide some sort of ticket out of it, usually in the email saying, ‘I’m totally aware that you are a rock star and you travel the world and I realize you probably won’t be able to meet with me. If you can, cool, if you can’t, that’s okay too’.

I find that works so much better. So I think the idea is – I’m just going to read it out because I think the way I wrote it down, I like the articulation of it. Give new leads an opportunity to say ‘No thanks’ without making it awkward or uncomfortable. That may lead to a deal at a later date. This is especially true, by the way, for things like media. I’ve gotten pretty close to some of the reporters at places like TechCrunch and Mashable and GigaOM and a lot of those great reporters there. In some cases, I’m friends with them on a personal level, and to be honest with you, I’ve heard horror stories about people just slamming the Mashable help desk, and obviously cc’ing Pete Cashmore and everything saying, ‘I have the best company in the world. If you don’t report on me, you are so stupid’. I have news for you. These guys have memory. They remember all these things. They live and die in email and relationships.

Often, even today, Shopify is doing pretty good and people know about us, but even today when we launch something, be it the contest or the Shopify fund where we raise money, and I want to get some media attention, I will usually say at the end of the email, “By the way, I know this may not be relevant given your current scope, but if it is, cool, and if it’s not, see you in [??] next year. Can’t wait to buy you a beer”. I find it so much better, so much easier. The relationships grow and foster and marinate. So I really believe in providing a little disclaimer at the end just to allow them to circle the ‘No thank you, but please try again’ box as opposed to the ‘Ignore’ box.

Andrew: That’s counter-intuitive. Most of us think well, if you want something, you have to go after it. You can’t give yourself or anyone else a way out or else you’re going to go out, and you’re saying, “You know what? If you give them a way out graciously now, they might come back in later on”.

Harley: I mean, look, again, going back to the [??] my arm. You know me a little bit now, I’m a hustler. I push and push and I’m assertive and sometimes I’m overly aggressive, but I’m not stupid. I do know that people recognize that if you push too hard, eventually you’re going to break the relationship. I believe that by being a little bit softer, you can still be aggressive, you can still be a hustler and you can still be assertive, but by giving a way out, it kind of just diffuses the whole situation.

Going back to that thing about the Steve Jobs comment, even if you don’t know, if you’re emailing someone cold and you don’t know what the objective is, maybe even say, “Look, I don’t actually know what the big picture looks like. I know that I admire you. I hope you admire us. I think we can do something together. If not, check [??], we’ll have a beer together”. So I think that’s a really great way to soften the blow when you’re making a hard pitch is just giving them a way out.

Andrew: I want to read something from… a comment on the website, recommend a site, and then look around your office. So here’s the comment, and you guys can all read this along with me or confirm this with me. It’s on the interview that I did for SkillPages, how the best marketplace you never heard of was built. Jesse Peacock wrote one of the best comments on the site. He said, ‘Andrew, I don’t want to mess around with emailing you, and I wanted people to see this. Everything you teach on Mixergy works. I tried two different startups, and now one of them has struck. I’m now making triple what I used to earn, and I wanted to say thank you. I just subscribed to Premium, and I couldn’t be happier’. And he has his message up there.

It’s because of interviews like this. We could do an interview about a popular television show – I don’t know what’s popular – Dancing with the Stars. We get triple, quadruple the traffic, like that. But I don’t care about that. What I care about are real entrepreneurs who are really building businesses, and that’s why this kind of interview works for them because it gives them the tools to build their companies. Jesse Peacock, thank you for saying that.

If you want to join Jesse Peacock and be a Mixergy Premium member, go to and sign up. And if you do, and when you do, I should say, I’m going to recommend that you check out the course that I mentioned earlier today with Amit Kumar of Lexity. He teaches how to create a marketing plan that will ship customers to you. Specifically, he walks you through how to get your first customers, your next customers, how to get on platforms, and as you can see from this interview, Harley at Shopify got his product on their platform and helped them get lots of customers. So he has the track record, and frankly, that’s very important to us here at Mixergy. The people who teach courses on Mixergy Premium have that track record.

And then he says, “Here’s how to get your customers to become evangelists, and how to get them to become repeat customers of yours”.

Harley: I can vouch, by the way, he’s the real deal. I know what he’s built, I know his character. He’s the real deal, so I can vouch for his effectiveness.

Andrew: I love hearing that. And that’s really where a lot of the revenue here at Mixergy goes, to research. And it’s not just research you guys see in the interviews. What we do is we research everyone, well, not everyone, but as many people who ask us to be interviewed as possible to make sure that it’s real.

I remember once, Harley, I was running in to work, and my text goes off. It was a text message from one of our researchers who says, ‘Hey, this guest who you’re going to have on in about an hour, later today when you get in the office, he’s not really ready. The company maybe one day will be ready, but it’s not really ready to do an interview. You’re going to embarrass him and you’re going to embarrass yourself’. If it wasn’t for the researcher, I wouldn’t have known this. So we had a conversation with him, very frank, and we found a way to do something else together.

The Mixergy Premium members, in addition to helping themselves grow their businesses, they’re really helping me create a better product here on Mixergy, and I thank them. So, that’s where you can see the courses if you’re a member, and that’s where you can join if you’d like to be a member and take this conversation and this relationship to the next level.

Harley, what do you got around your office?

Harley: All right, so how should we…

Andrew: Have you turned your computer on? You’ve got a nice setup here.

Harley: I do. I’m using the 27-inch screen right now, but I will kind of turn it around and show you what I’m working with here. So, I have my bookshelf with all my books, I have my scotch bar. But actually, maybe what we should do is…Andrew, can I take you on my laptop and just take you on a walk?

Andrew: You want to do it on another computer?


Andrew: Well, that experiment didn’t work. It’s been a few days since we shot that interview, and actually, I’m looking at the video and realizing that the video of the walk-through of the office just didn’t come out right. In fact, it didn’t come out at all. If you’ve ever walked with your laptop through your office or through your house while you’re talking to someone on Skype, you know that it can be undependable and sometimes just unusable at all, and in this case it was unusable.

So, here’s what we’ll do. Harley put together a set of pictures of the office. You can see what he was showing us on the webcam. It’ll be part of this post, and you can click over and take a look at it at your own pace, if you want to. If not, I still hope you’ll do what I do, which is to say, “Thank you, Harley, thank you Shopify, for doing this interview”, and I’m also going to thank you guys for being a part of Mixergy and for watching. Thanks.

Who should we feature on Mixergy? Let us know who you think would make a great interviewee.