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Interview with Entrepreneur David Hassell, CEO of 15Five

John Doherty —  April 17, 2013
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Entrepreneurs are some of the most interesting people in the world. I recently had the pleasure of interviewing David Hassell, who is the CEO and Founder of 15Five, a product built to better enable managers and employees to give and receive quality feedback in less time. Throughout this conversation we talk about not only entrepreneurship, but also productivity, the power of why, and the driving force behind what he does. Have a listen/read!

Here is David’s official biography, and you can read their blog here (including an interview with Simon Sinek on The Power of Why):


David HassellDavid Hassell is a serial entrepreneur and CEO of 15Five, a software company focused on producing transparency and alignment in organizations through structured, efficient and effective communication practices. David has also been named The Most Connected Man You Don’t Know in Silicon Valley by Forbes.




John: All right, so welcome again folks to another interview here on my site johnfdoherty.com. Today I have the great pleasure of interviewing David Hassell who I’ve been connected with, he is currently the CEO and Founder of 15Five, which is a SaaS product basically, to help offices function better to provide good feedback, real time feedback in positive ways to help teams work better. He’s also a long time entrepreneur connected with Dan Martel, who I interviewed here on the site a few weeks ago, as you may remember. So basically today we’re going to be talking about entrepreneurship, going to be talking about 15Five a little bit again, it’s productivity hacks, so it should be a great conversation. So welcome.

David: Yeah, thank you, great to be here.

John: Yeah, so, tell us what you’re currently up to these days. What sort of things are keeping you busy out there on the West Coast?

David: Yeah, right now I’m 100% focused on 15Five. In kind of a past life I billed myself not as a serial entrepreneur, but more of a parallel entrepreneur. I think I had a little bit of entrepreneuritis in doing five things at once and realizing that the only way I could be super productive was to narrow my focus down to not only just one business, but even within that like a few core things at any given time. So, for the past two years I’ve been building 15Five. We launched about a year ago, or we at least announced the product a year ago and launched for public use last June, so it’s been about 10 months. And we just closed a round of financing in January and we’re releasing, hopefully, our 2.0 product toward the end of Q2, so a lot going on.

John: Wow, congratulations.

David: Yeah, thanks.

John: Yeah, how’s that first year been?

David: It’s been pretty amazing. It was, I think the product was a lot more, was better received than I had anticipated. We got a lot of great press. Inc. Magazine wrote about us right off the bat and called us “The most have way to keep track of employees.”

John: Wow.

David: So, that was really fantastic and so, in fact, they just wrote another piece on us a couple of weeks ago, about tying us to the original Inc. Magazine article, but talked about the 15Five concept in March of 1988, which is 25 years ago. So they wrote about how they had originally introduced the concept to the world, how we took it on 25 years later, combined it with modern technology, and are now delivering it to the masses.

John: Wow, very cool. It’s not a bad way to go out the gate with a write up in Inc. Magazine. That’s pretty cool.

David: Exactly.

John: Yeah, but you’ve been an entrepreneur for a long time, right?

David: I have, yeah, ever since second grade.

John: Okay, what was your first entrepreneur adventure?

David: Well, you know, I had a best friend growing up, we created a company in second grade. We actually didn’t do anything until eighth grade when we started selling candy.

John: Okay.

David: It took us about six years to come up with that business plan. I started doing things in college where I would sell time fixing computers and selling RAM when you could actually make a huge amount of, there was a lot of markup in selling upgrades and things to computers. And then right out of college I started a Internet advertising tech company in New York, which is my first, kind of, real venture. I ran that about seven years in New York City with a partner. And then I started, I had a hobby business it was kind of a fun business doing adventure travel for kite surfers in North East Brazil.

John: Wow.

David: And started that company up and around 2004 – 2005 with a couple of partners and that’s also still going today. And then in the past five years I’ve been focused on a consulting practice called Strategy Day; where I work with CEO’s and their executive teams to help them narrow their focus to a few key things that would produce highest leverage in their business in doing these quarterly or annually off-sites. And then also 15Five is the latest venture.

John: Okay, so you still have your hands in multiple things even though your focus is on 15Five, you’re still doing the Strategy Day and all that?

David: Yeah, I still have, I’m still connected to the previous businesses, but I don’t spend any time on them. For Strategy Day I have just a limited number of really close clients that I’ll still do a day or two throughout the year but it’s not a focus.

John: Sure, gotcha, gotcha. So it sounds like, I hear about, I talk to a lot of entrepreneurs here in New York City that they’re like, “Oh, this is my, you know, this is my fifth start-up the other four didn’t really work out” it sounds like you’ve had some pretty good success. You’ve built companies that are still going. What do you think is the, what’s the key there?

David: Yeah, that’s a good question.

John: I’m sure there are a lot, but I mean it’s obviously not one thing, there’s no silver bullet, but . . .

David: Yeah, and I’ve had varying degrees of success in each one. I read a great quote recently by Paul Coelho, about that “The reward of our work is not what we create, but who we become”. And I think each one of these ventures, who I was at the beginning and who I was at the end were very, very different people. I’ve learned different ways to view the world; different skills, different things that I’ve now been able to parlay into the next enterprise. So my ability to be able to create momentum and success in 15Five is really tied to the things that I’ve done in the past at Indie, at Kite Adventures, at Strategy Day, all learning since.

I often think about in looking back and saying, “Wow it’s so bizarre, I never thought that starting this Kite Surfing company would lead me to being connected with a really powerful network in Silicon Valley, which would lead me to be able to attract the right investors for 15Five.” And, you know, really inspired by what Steve Jobs said in his commencement address about, “How you cannot connect the dots looking forward. You’ve got to follow your heart and do what inspires you and then you realize ten years later that what you were doing is actually perfectly aligned with what you’re creating now.”

John: Right, yeah, that actually really makes sense. So, I mean, which one of the, what’s the biggest lesson that you’ve learned throughout all of these, all these different ventures that you’ve done? I mean you’ve done everything from agency to like an outdoor adventure company to consulting and now you’re doing a SaaS product like . . .

David: Yeah.

John: I mean, it’s still varied right? You’re not like a one, just I do SaaS or I do consulting.

David: Exactly.

John: What’s like the common theme weaving those together?

David: You know, the interesting thing is that, I think ultimately the thing that kind of drive, that drove me previously was like the desire to create something new. And so regardless of whether that was a, you know, an adventure trip along the North East coast of Brazil that people hadn’t experienced or a new type of ad format, there was something there that, you know, I was drawn to create something new. As I got into it I think the biggest lesson was that when I started my first company it was, I was driven a lot by wanting to, you know, create something new and make money. You know, it was all about the money. Then I realized, wow, my heart’s not in this, I’m not really, it’s not really tied to my passion or what I want, or how I want to contribute to the world. And so then I said well let me do something that, I’ll follow my passion. So I said all right I love kite surfing, I’ll start this kite surfing travel company and so I followed my passion, but there is not a lot of money necessarily in that, right? So here I was venture number one follow the money no passion, venture number two follow the passion, no money. Then I realized, wow, I think the ultimate success in life is when you can bring those two things together. And so with 15Five, you know, I really connected to the real, the why that drives me. I don’t know if you’re familiar with Simon Sinek, but he’s pretty, got a great tech talk called: Start With Why, Get A Book.

John: One of my favorites.

David: Yeah, so Simon’s, you know, Simon’s great, dear friend and one of our advisers at 15Five. And for us it’s, you know, my why and our why, is to really help individuals and organizations achieve their highest potential. And so when we think about creating a product that helps organizations achieve whatever potential they’re out to create, you know, that really inspires me. That wakes me up in the morning. That has me have a lot of, like, energy and drive to create the business and know that we’re creating something that is highly scalable that will create, you know, a lot of enterprise value and there’s money in the process as well.

John: Right, yeah, that absolutely makes sense. I mean that I watched the Power of Why probably a year ago. I had been in marketing, I’d been out of school, like, five years at that point, I had been in marketing for a few years and as soon as I watched that I was, like, it was one of those, like, paradigm shifts, that all of a sudden, like, yeah, I get it now.

David: That’s exactly it. And I love when you get those moments, those paradigm shifts in your life and all of a sudden, you know, everything starts to click and make sense and you see the world in a different way. And I had the same experience when I first heard Simon speak.

John: Yeah, that’s awesome, so what is it about 15Five that, I mean, like, I mean, the why, what’s the why about that, why behind that, that inspires you? Like what gets you out of bed everyday with 15Five and tell us a little bit about 15Five, like why, how did you come up with the idea, how did you start it?

David: Yeah, so, you know, like I said, I love paradigm shifting ideas and things that once you learn about them, you know, something clicks. And when I learned about getting things done, for example, about getting everything out of your head and creating these light weight structures, there’s a book called “The Rockefeller Habits”, that’s really popular in this group called: The Entrepreneurs Organization about creating these, you know, these meeting rhythms that you put in place in your company and all of a sudden it becomes the heartbeat of your company. So I heard about the 15Five concepts through a friend who had heard about it through the grapevine and what not. It was originally something the founder of Patagonia, Yvon Chouinard, had come up with as a way to do two things. One, to be able to know what was happening in his company even when he was traveling half the year; testing gear, climbing mountains, following his passion he built his business around his lifestyle. And then also to have his employees feel really engaged in the company that they had a voice, that they were part of a mission. And Patagonia is one of the, premium values driven organizations, the ones that really have strong, strong values, they’re making a difference in the world, they adhere to those values. And here is this great business practice that allowed the CEO to be free and roam around and stay in touch and have the employees feel like they were engaged and had a voice and create this heartbeat of the company.

And, you know, me realizing that I wanted to create a business that had something to do with communication and collaboration, to help organizations to be there best and to achieve their potential. And realizing that communication rhythms, and often times the breakdowns a lot of companies had were breakdowns in communication. So I heard about this super, simple idea to basically put the structure in place that’s so light weight that anybody could do it without much effort. I was just like wow, that’s it, everybody needs this, this is like a baseline. So that was the impetus to start the company. And I see a lot of like, the guys at 37Signals have been really, like, you know, forging the path for creating great, simple, beautiful, easy to use software out there, and we want to be part of that movement. I think often times people when they’re building software they don’t realize they’re building software for human beings, you know?

John: Yes.

David: We talk about the users and the things like this so, instead of saying “Invite a new user”, we say “Invite somebody”, you know. We don’t have a user’s administration, we have a people’s administration. You know, this is really thinking about how do we make the software human-centric for real human beings to use and better their lives? And then make sure that everybody’s on the same page, that people feel engaged, that, you know, we flatten the hierarchies and the distance between a front line employee and an executive or a CEO.

John: Gotcha, gotcha, cool, so you think that, do you think this business could of worked out, you know, ten years ago when people weren’t working as remote? Do you think, you know, would of been as successful and people needed it as badly?

David: I, you know, timings everything. Ten years ago I was working with the Erickson’s Cyber Lab when they first came out with triangulation of cell phones and we were building mobile coupons to push down to the phones when people say, walked by a Starbucks. Little bit too early.

John: Yes.

David: Here we are and all that kind of stuff is happening. So I think the timings right. I think the, what we’re offering in addition to, so first of all, people are familiar with social networking and there are elements of 15Five that are inherently social. You know, people have conversations and there’s avatars and things like that that we’re building into the 2.0. So we’ve got those elements, people already understand how that works, people are more distributed. There’s more information that we’re just being hit with, like, all day long, like, always on social networking, email, news, and all this kind of stuff. So we’re almost a reprieve to that saying, “Hey, we don’t want to be an always on technology. Literally we want you to box this into 15 minutes a week; where you come in and you dump all of the most important things that are going on in the organization from your perspective. Your manager takes no more than five minutes to read, review, and respond and everybody’s synced up.” So it’s almost the antithesis of the overload of information. We want to boil it down to the essence. So I think that it is really timely.

John: Yeah, absolutely, that makes a lot of sense. How did you, how did you first validate the idea? Obviously it’s an older idea, coming from the founder of Patagonia, who’s one of my personal hero’s as well. I love the company. I’m an outdoorsy guy as well, so once I, I love Patagonia gear and then I heard about the company I was like, wow, that’s amazing. But how did you validate the idea for 15Five? What kind of steps that you went through? Eventually you said, like, “Holy crap we need to build this, this has legs.”

David: Yeah, that’s a great question because, you know, what I often see with entrepreneurs doing is they follow kind of a traditional path because that’s the way that it’s always been done. You know, so you run out and you raid friends and family around financing because you have a great idea. Then you use that money to try to validate your idea. And the problem is that’s the highest risk period of the company and your risking your closest friends and family’s money on a guess.

John: Right, right.

David: So I said, “Wait a minute, we don’t have to follow that, let’s see with the connections and resources and time that we have, you know, myself and a co-founder, what have we got that we can actually do without going out and raising around? How can we validate it before we do that?” So we actually built a really light weight prototype, I had a bunch of CEO friends and said, “Hey, would you try this out?” Thankfully they’re still my friends, even because it was somewhat of a painful experience early on with their employees and trying to get this to work right, but they were gracious enough to let us really be a part of their company and talk to their employees and figure out what was working and what wasn’t.

And we actually got it to a point, in about ten companies, it was working pretty well and then we went out to a friend’s design firm and he agreed to give us some design services on a convertible basis. So we actually got to a point of having our first paying customer before we had raised any money and it was all done, kind of, on part-time weekends, nights and weekends while we were focusing on our other endeavors. And we got to a pretty reasonable proof of concept, we had, someone say, “Yes, this is really valuable, I’m willing to pay money for this.” And then we went out and raised a small amount of financing to take it to the next level.

John: Gotcha. Yeah, that’s something that Dan and I talked about a few weeks ago. He was basically like, I was like what’s the number one, you know, piece of advice that you would give to entrepreneurs that are, you know, building a product? He was like, get money in hand. You know, don’t just go and ask, don’t just say, “Hey, would you do this?” right, and people were like, “Oh yea, sure I’d do that” like, that’s not good enough. Like, get someone to pay you.

David: Absolutely.

John: And then when someone pays you and then when someone pays you it’s like, all right, let’s go. Will the first person pay me? Will the second person pay me? Will the third person pay me? Okay, let’s make it happen.

David: That’s really good advice. You know, actually in, related to that, so in the exploratory phase, kind of the two years between I left the last company was doing consulting looking for what this next venture would be, you know, I was really in this exploration about what’s my why? What do I share about? Who do I want to help? All this kind of stuff and I had lots of ideas that’s the point, you’re in this ideation phase, right, and I was talking to a lot of people. And every single one of my ideas in looking back they were all pretty terrible, but every single one I would go out to folks and say, “What do you think of this?” and they’d be like, “Ha, that’s a great idea.” All right, people like to tell you that you have great ideas.

John: Right.

David: What I realized though was when I hit on 15Five and I’d go out to CEO’s and tell them that they said something a little bit different. They said, “That’s a great idea, when can I use it?” So it was that “When can I use it?” that indication of oh, I think it’s great and I need that, that’s what you’re looking for and so, you know, you want to be careful when you’re talking to folks, you’re talking to the right people who would use your product, that they, you know, express genuine interest about wanting to use it themselves, and ultimately, yes, paying is the ultimate validation.

John: Gotcha, gotcha. Yeah, that’s really, that’s great advice. That’s kind of like the next, the next step is the people saying, the people you’re talking too directly, like, “Oh yeah, my mom and dad might be interested in that” it’s like, “I want to use this,” right because those are the people that you, I mean, those are the people that you know, that’s the market that you know and it’s easiest and I would say, I would argue best to create something for, in a niche that you’re already familiar with, at least to start there and then you can go broader.

David: Yeah, that’s exactly right and just like anything else if you follow, like, Jeffrey Moore’s model of the Law of Diffusion of Innovations, you want to find those people on the very, very edge of the bell curve who really care about your problem. Don’t try to make it the ultimate solution for everyone right off the bat. Solve a small niche percentage population, you know, problem for that niche percentage with a very clearly defined, pain or world view, and then, you know, ultimately, you know, you want to be able to look at this and say, “Yes, this would be broadly applicable to the mass market eventually,” but you’re not solving, you know, the mass market problem right off the bat.

John: Right, absolutely. Would you say you guys are getting to that point with 15Five?

David: We are, you know, the past year we’ve acquired, you know, hundreds of customers which I didn’t expect we would do in this first year. So pretty happy about that, but we’re still, we’re still really focused on I would say still those early adopters and innovators. In our view, the people who are really focused on are companies who really aspire to be great. Who want to build awesome cultures. Who care about their employees. Who, you know, are mission and value driven. So those are the companies that we’re targeting first and foremost, and we think if we have success in that cohort, then it will, you know, then the idea will easily spread.

John: Yeah, absolutely. So one question I have there is there are, you know, obviously there are a lot of companies that do think that way.

David: Yep.

John: That would be great. That want to invest in quality. There are also a lot of companies out there that don’t or that are afraid to or something like that. How would you, have you come across people like that, and do you have people like that signed up to 15Five?

David: Absolutely, yeah.

John: And how, I mean, how do you, when you come across companies like that what sort of advice do you give them?

David: That’s a good question. Ultimately, here’s the interesting thing, you know, in my work with Strategy Day, you know, I worked with dozens and dozens of companies and, you know, just run of the mill companies that you wouldn’t think that they’ve got a strong purpose that’s driving them. And one of the things that I would do with every company who hadn’t seen it, is I would show them Simon Sinek’s video. And there is not a single person left who isn’t inspired by that message, and realizing that they were in their business for some deeper purpose, right? So I believe it’s in every body to connect with that and we have companies who maybe aren’t in that perfect niche that I just described who are using 15Five, but we want, we want to not only provide the tools, but provide education and resources and, and things that can help them now as a customer move along that path. And so long term I do want to see 15Five move into the mass market. I want to see it as a mass market tool and really help the, kind of, part of that cause to get people to look a little bit deeper about what’s the purpose of why they are in in business? What are they really trying to do?

I mean, you look at Zappo’s, you know, they were a shoe company, but they realized no, we want to provide WOW experiences for our customers. That was, the first thing was, we want to be the most shoes you can buy online. Then it was, we want to delight our customers. Then it was like, no, we want to delight everybody, and they eventually kept peeling back the onion and realized that they’re whole reason for being in the world is to just deliver happiness to everybody who touches the company, and they just happen to sell shoes. And, you know, had a hugely successful company as a result. And so I think that that is possible for every company and every person and so we just want to provide a great service that will work for any company, but also be a source of inspiration for people to look a little deeper.

John: Right, absolutely. So, this has come up a couple of times, but I guess this is the best time to bring it up. You talked about the founder of Patagonia and how he built a company, kind of, for him it was kind of a lifestyle business, but he also wanted to keep up with what was going on.

David: Yep.

John: You mentioned these different CEO’s that you talked to that, you know, they have a very strong vision, they, you know, they have their “why.” I think about, and there’s been a lot of talk recently, you know, like, in tech blogging circles about company culture like Dharmesh Shah from HubSpot recently had a presentation that went, it was like number one in Hacker News for a while I think, and went hot on Slide Share. It was, like featured as probably 50 to 100,000 views now.

David: Yep.

John: You talked about HubSpots culture, my friend Rand Fishkin, you know, talks about culture all the time at his company SEOmoz .

David: Yes.

John: Is it the CEO’s job to drive culture? Is it their job to drive that “why?”

David: It absolutely is.

John: Okay.

David: It absolutely is. I believe that if you look close enough, often times you’ll find that the companies “why” is the founder’s “why” or at least very, very closely aligned. You know, Steve Jobs is an example, Simon Sinek’s is an example about his “why” was really to challenge the status quo and the company was an expression of that. And so the, what caused the founder and co-founders to start the company was something about the company, right? There was some purpose there for them, and so often times they don’t even know it. I mean, we only got to a deeper level of clarity, like, last week, I mean, we’ve been in this for two years and we keep peeling back the onion, right?

John: Yeah.

David: And, but once you get it clear, then it really is your job to make sure that everybody you bring on to the team is aligned with that. Because the difference between an employee who’s inspired by the “why” and who’s not is enormous. Like, we have such a high caliber team even though we’re such a small team, because everyone is so bought into the mission, the vision. And then the value piece is also really important, what HubSpot has done is an excellent example, HubSpot and Zappo’s are two great examples of companies who have clearly defined their values that drive them; and it’s not enough just to write them down. The key thing is to make sure that you’re hiring people who already believe those values, not trying to push them out to somebody. So you bring people who already share that mentality and these become like, these become like points you can reference back to. One of our design values is this concept of elegant simplicity. It comes up in conversations all the time. You know, one of our culture, on piece on values and I think it’s really important to know is that the, the, kind of, definition of values just in its basic form, is like something you value. Like I value accountability or I value health. I value, these are things I value, like actionable verb statements, Zappo’s has done this, Hub Spot has done this so, for example one of our, one of our core values is: Hold and Be Accountable. So I’m going to hold my team accountable. I expect my team to hold me accountable and I agree to be held accountable for my work.

One of our values is to embrace freedom and flexibility. So that I’m here in Sedonna and I’m just as productive as if I’m with my team in San Fransico. Another one is find the leverage, we’re a small team, we’ve got like, we can’t just be, you know, going through the motions. We’ve got to have high leverage with our work. And cultivating health and vitality. So these are things that we can keep going back to in every one of our conversations about how we really want to be in the world. There are commitments. There are what we care about. And ultimately if we live the sum of our values and we all do it together, we’re going to create an extraordinary organization. And so that’s why Hub Spot’s culture stand that they put out there is so popular because it really does paint a picture about what an amazing organization it would be to work there.

John: Yeah, yeah, it’s funny to me that you talk, that you say, “We’ll build an amazing organization, not an amazing product.” Because amazing products come out of amazing organizations, right?

David: That’s exactly right, yeah, that’s the key. I think that 15Five and the product that we built is a great product and I don’t, I don’t think that’s where we’re going to stop. You know, if we keep focusing on our “why”; which is to help individuals and organizations to reach their highest potential, and we keep focusing on our, kind of, our sweet spot, which is super, simple, software as a service for human beings who aspire to be great, that’s where we focus on. So it’s like those two things in concert, I mean, there are lots of different directions we can go on and it may be three, four, five years before we actually branch out and do other things, but we want to build an amazing group of people, an amazing culture that inspires innovation, that inspires keeping, looking out at our customers like where they’re struggling and where we can help and what other services and products and whatever else we can deliver, you know, to help them do that.

John: Gotcha, that really, that really makes sense. Look at, I feel like I mention these guys in every interview that I do, but look at Ever Note, right?

David: Yep.

John: It’s a product that you probably use it, I definitely use it, I use it for everything. I write blog posts on the subway on my cell phone, right? EverNote, you think about it, it’s crazy.

David: Yep.

John: But like I saw an interview, or read in an interview with their founder awhile ago and someone is basically like, are you going to, when are you going to sell? He’s like, what are you talking about? Like, I want to build EverNote into a $100 million company, right? I want it to be a company that lasts for a hundred years.

David: Yes.

John: And obviously they branched out into different things and they have like, the desktop client and the mobile client and the thick client and what have you, are what they’re known for, but they also all these other apps that are also popular.

David: Yep, one of my favorites.

John: Yep, so yeah, I think that’s really interesting and then it doesn’t, I mean, markets change. So then you’re not kept into just one, you know, into one market, into one product. You can start with something small and then you, kind of, dominate that. Then all right, what’s next? You still have that entrepreneurial or intrepreneurial spirit..

David: That’s right.

John: Going on.

David: And balancing that with focus, right? So we were talking a little bit about productivity earlier, you know, I’m a big believer in, in extreme focus. You know and sacrificing the good for the great. Sometimes you have to, you have to let go of the 50 things that you want to do to really get the five things that really matter done. You know, when Steve Jobs came back to Apple, he drew like a cross on the board and said, you know, “Consumer, business, desktop, laptop that’s all we’re going to do.” He cut out the printers and all this other stuff and said, “We’ve got four products.” And they went, it was a huge backlash, but it was a brilliant strategy because it forced the company to narrow their focus to just the essentials, and then of course they built back out from there. And, you know, hugely successful today, here’s a company with 55,000 employees that decided to put the iPad on hold for three or four years to launch the iPhone because the iPad was actually in development first. You know, to have that kind of level of extreme focus, you know, shows you that even at that scale, that size of organization how important it is. So we’re big believers in staying really, really focused and only branching out when you have the capacity to do so. Because if you over reach, if you reach to far and you don’t have a solid base, you know, you can easily get knocked off. And so, you know, I think it’s great to have the “why” to keep referencing back to and to decide yes, what’s next, but also make sure that you’ve built a solid base before you talk on too many things.

John: Right, yeah, that solid base is really interesting to me because you talk about focus obviously you’re focusing on 15Five, but you’ve done a bunch of other things in the past, right? Which you focused on for a time and then move on, you know, so how, I have so many different questions about this because I love this topic. But, I mean, what is, how, how do you get there as a person to be able to do this? I mean I love Inbox Zero. I love, you know, getting things done. You know I have my, I have my checklists, I basically set it out the day before everything that I’m getting done tomorrow.

David: Yeah.

John: You know, focus, obviously sometimes something slips through, you know, managing people it happens, but like, how, what do you do to keep yourself focused? As a person, as an entrepreneur, as a boss, as a CEO?

David: That’s a great question. You know what you’re talking about, you know all these things Inbox Zero, about, you know, doing your To Do list, all these types of things, you know, ultimately you’ve got to cultivate great habits. So a lot of people think, oh I need, I wish I had more discipline. I wish I had more discipline to get my email or my Inbox to zero or to stay focused or this and stuff. The problem is that every single day we only get a very, very, very limited amount of will power that we can use towards discipline. So if you try to use up that will power to, just by keeping to all the things that you think you should be doing, you’re never actually, you’re never actually going to make any difference. Instead, it’s better to channel that will power into developing one great habit at a time. And then those habits just become automatic. So there’s a concept that I heard once, it was brilliant, it said, you know, “People wish they had more discipline, but if you look at every single person, they’re 100% disciplined to their existing set of habits.” So I’m really big into creating great habits for yourself and creating great habits for your organization. So one habit that we have as an organization is that every three months we get in a room for a whole day and we list all the possible things that we could do over the next three months. And we narrow it down to just five. There are five things that we are really going to focus our attention about all else, and we actually put everything else on what we call an avoidance list.

These are things that we’d love to work on, but we’re not allowed to touch them until we get the top five done. Because it’s not all the stuff that you think that is getting in the way, like all these errands that you have to do and the emails and stuff that’s keeping you from, you know, the five most important things, it’s actually the 35 other things that you kind of want to get done to that you think are important, so you dabble in those and you can’t channel your energy into the most important stuff. So it’s an organizational habit for us to create our top five, as an organization, and then each one of us has our own top five. And we only get no more, each person in the company, gets no more than five big rocks to work on, on any given time and once a week we all get on the phone together and update our status on our five rocks, green, yellow, red, help each other if we’re behind. And as we knock one off the list we go back to our avoidance list and we pull one off. So that’s an example of how we maintain focus.

John: Gotcha, so it’s kind of like, it’s like a super drawn out Scrum agile methodology, you basically do three month sprints and then once a week you get together and basically have a stand up.

David: Yeah, basically, that’s right, yep.

John: Very interesting. I actually, I really like that idea, I’ve never thought about taking that and just focusing down into five key things like, you know, we’re focused on making our customers happy. We’re focused on, whatever it is like, version 2.0 but not just the admin section of the product, that sort of thing that . . .

David: Exactly.

John: And so then, I heard something interesting, it was awhile ago, I don’t remember the exact quote or even where I read it, or if I read it or heard it or whatever, but it was basically talking about, like, you know, the power of focus allows you to say no. So once you figure out where you are going, it becomes very, very easy to say no if someone’s like, “Hey can you do this?” It’s like, “No, that’s not what I’m focused on. That’s not what I’m doing.”

David: That’s exactly right.

John: That’s not one of my five.

David: Yep, yeah, that’s exactly right. So I have, I have some pretty extreme practices around my own personal productivity and really blocking out my time. I don’t know if you ever heard the rocks analogy where, you know, you have a glass jar. So a professor walks into the room and he’s got this big glass jar on the table, and next to it he’s got a big pile of giant rocks. And he starts putting the rocks into the glass jar until he fills it all the way to the top. And he asks the class, you know, “Is the jar full?” And they say, “Yeah, definitely full.” So he pulls out a bag of gravel and he pours it all into there or smaller rocks and gravel, fills it up. Asks again is it full? And the class says, “Yes.” And he pulls out a thing of sand and he fills the glass up with sand and he fills it up to the top, asks the question again and then he pulls out a picture of water and fills all that in. And so if had started out with putting in the sand, the gravel, and whatever there’s no way you can fit the big rocks in, right? But if you put them in first, you know, the rest of your life, the smaller things and the secondary priorities all fit in around them. So I have a practice every week, you know, looking out at my calendar and scheduling big 90 minutes blocks for all of my top five rocks and make sure those are handled first. And I have one day a week that I do phone calls. And, generally I only do phone calls if they’re related to my top five. I have one day a month that if I want to have an exploratory conversation with someone, it might be a great future, I don’t know, who knows, it might be a great potential partner down the line or an employee or something like that, I don’t want to just say no forever. I think it really is important to have those conversations, but I limit it to one work day a month and I book myself from morning till night, all, what I call my exploratory meetings and phone calls and I just sit in a place either in San Francisco or at my office and they come to me and we go for walks and we have coffee and we have lunch, but I limit that to one day a month, because there are only 22 work days in a month and I can’t really, if I keep breaking up my workdays with things that aren’t tied to my top five, you know, I’d never get those rocks done.

John: Right, yeah, that’s really, that’s really interesting. I mean, that takes, that obviously takes a ton of discipline, where this is planned like, you know, we were just talking about . . .

David: Actually it doesn’t. Yeah, if it took a lot of discipline I wouldn’t be able to do it. It’s actually, it’s actually taking the time to reflect, to step back and say here’s how I’m going to structure my calendar. And then my assistant actually handles that, so she handles, she knows which day of the month that is and he schedules them all out. But, you know, it’s taking me, like, you know, eight years to get to this point where I’ve got the structures in place to let me focus and the right habits. But it’s a journey. It’s not easy to get there.

John: Got it, yeah. So, maybe it’s not discipline, but it’s intentionality. You’re being very intentional and focused on what you’re . . .

David: That’s it.

John: On what your setting out to do.

David: Yeah.

John: Okay.

David: And practicing, it’s like we all fall off the bucket or the wagon, you know, it’s like, so it’s realizing okay, I’ve got to keep bringing my focus back and practice and every time you, self-reflection once a week, taking a step back and saying was I focused this week? Where wasn’t I focused? What can I do better next week? What new habits should I be taking on?

John: Right, right, absolutely, cool. So, I mean we’re starting to kind of run out of time, I want to be very cognizant of your time as well, but hopefully there are going to be a lot of entrepreneurs looking at, you know, watching this and gleaning a lot of value from this conversation. I know I’ve gotten a ton from it, but as a long time entrepreneur, what would you say is the biggest thing that’s influenced you, what’s the biggest thing that you’ve learned in all your time as an entrepreneur?

David: You know, I, the biggest thing, I think, is life’s too short not to work on something that matters, right?

John: Dan said the same thing.

David: Is that right?

John: Yeah.

David: That’s great. Find something that really matters because if you, anytime you start one of these things, you know, you’re in it for like a minimum of three years, could be in it for a decade. If you got four decades of your work career, that’s like four opportunities to do something. And so, do something that matters. I was actually watching, I can’t remember the name of the guy, he was a former SAP guy I think, who started something called: Better World or it’s this network of, of battery powered car replacement stations that he built across Israel, I can’t remember the name of the company, but he spoke at a conference called Summit Series that I attended and he spoke out to the audience and said, “Hey, you’re all working on something, you know, maybe it’s free, maybe it’s not” he said, “But when you’re done I want you to look around and ask yourself the question, like, what needs to change in the world? What do I really care about? How can I solve some big problem?” And he said, “Find your question.” So, his company has raised a billion dollars in venture capital. He’s making a huge change, he’s now built infrastructure to drive all the way across the country of Israel without having to stop the electric vehicle because the batteries get replaced, there is no charging.

John: Wow.

David: And that’s a huge concept, and I think it costs them, basically what it would cost for a week worth of oil in the country. And the question he said he asked was how could we get Israel off of oil? I mean that’s a big question.

John: Yeah.

David: And he realized to put that same infrastructure across the country in the United States would basically cost one week of what we spend on oil in the U.S., to create the infrastructure of these charging replacement stations. So, start out with, that was a great, I mean, a great frame of start out with the question, like, how could we do this and let the ideas flow from there. Find a question that matters to you and follow that.

John: Yeah, it’s kind of the biggest boulder, right? I mean we talk about, you talk about sands or stones or rocks, I mean, that’s basically a boulder.

David: A boulder, yeah.

John: How do we end homelessness, you know?

David: Right.

John: It makes you dream huge.

David: Exactly.

John: Cool, very cool. Well David, I really appreciate your time. It’s been a pleasure talking to you, connecting with you. If you’re ever in New York City, you know, look me up, I’d love to meet up, you know, beers are on me.

David: That would be great. I’ve really enjoyed this. I love talking about this stuff and it’s great to connect.

John: Wonderful. All right, you have a great evening.

David: You too, take care.

John Doherty

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I'm the Senior Marketing Manager of HotPads.com, based in San Francisco. Previous to Hotpads I worked at Distilled for 2 years as an online marketing consultant. In my spare time I shoot lifestyle photography, ski, rock climb, and update my Twitter and Google+ accounts.

2 responses to Interview with Entrepreneur David Hassell, CEO of 15Five

  1. Great interview. Thanks for mentioning the HubSpot Culture Code deck (which is now up to 375,000+ views on slideshare).

    Readers can find it here: http://CultureCode.com