Ray Gillenwater is an entrepreneur, a former executive at BlackBerry, and an Angel investor. He is currently CEO and Co-founder of SpeakUp – an employee innovation and engagement platform that enables anyone within a company to create positive change. An entrepreneur since age 10, Ray is here to share his story.
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- ‘Outsource $10 per hour and above tasks, and insource $100 ones.’ – Unknown click to tweet!
- Ray and his partner tried to hedge their bets, diversify, and launch three startups at once, and it all blew up in their face…
Entrepreneurial AH-HA Moment
- ‘On the verge of being promoted or fired.’ Love this quote by Ray, and he expounds mightily.
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John: Entrepreneur on Fire 777. What's shaking Fire Nation? Johnny Dumas here. And I am fired up to bring you our featured guest today, Ray Gillenwater. Ray, are you prepared to ignite?
Ray: Of course, let’s go.
John: Awesome. Ray’s an entrepreneur, a former executive at BlackBerry and an Angel investor. He is currently CEO and cofounder of SpeakUp: an employee innovation and engagement platform that enables anyone within a company to create positive change. An entrepreneur since age ten, Ray is here to tell his story. And Ray, I've given Fire Nation just a little insight, so share more about you personally, and a little bit about the biz?
Ray: Yeah, for sure. So let’s see, I started my career, probably at 19 with Verizon. And back in those days, I was just doing customer service in a retail store. I found that by putting in a lot more hours and energy than other people around me, I could get more done and get promoted really quickly. And I took that mentality to great heights within Verizon and was promoted very quickly. And then jumped over to BlackBerry, and that was in ’07. So at BlackBerry, I took a similar approach. I set some records in California, and then jumped over to Asia with the company. We built a billion dollar business in Indonesia, and blew up some other emerging markets to great success, which was a lot of fun.
And then, I ended my career with those guys in 2012 as the managing director of Australia and New Zealand. So that’s a bit about me and my career. And then, my current project, my absolutely obsession is called SpeakUp: getspeakup.com. And as you said, we're enabling anyone, any company to create positive change at work. And essentially the way that works is anyone can post problems, they can share ideas and it's all voteable in sort of a read it or stack overflow style, which means that now anyone can have their voice heard at work, and companies can benefit from the collective wisdom of their teams.
So we've been publically released for about two months now. We're growing really nicely. We have a – the who’s who list of amazing companies signed up for us out of Silicone Valley. And also we're in over 180 cities around the world. And really excited about the company and really excited to be here, so thanks John.
John: Well, Ray, thank you my friend for taking time out of your incredibly busy schedule. And I'm excited to talk about SpeakUp. And, you know, really about how it benefits companies and your vision for the future, and all that jazz? And I'm excited to talk about your entrepreneurial journey as whole. I mean, that’s what we do here at Entrepreneur on Fire. And before we do, I do want you to share with us a success quote, Ray. And why you chose this specific quote?
Ray: Yeah, sure. So I put a bit of thought into this. Some of those general wisdom quotes are sort of fluffy and clichéd, but there is one for sure that can help you focus. And that one is one that I apply as often as possible, which is: outsource $10 per hour tasks, and in-source $100 per hour and above tasks. And the simple concept behind that is, you need to value your time and you need to focus on elements of your business that only you can do. And other things – because as an entrepreneur you're always going to have more stuff to do than time in the day. So it's a matter of focusing and prioritizing.
And entrepreneurs that can do that really well and manage those other tasks through other people are more efficient, more affective, and they get more out of their 168 hour week.
John: See, I love that quote. And I know Fire Nation resonates with it, too. I've had my good friend a couple times on this show, Chris Ducker of Virtual Freedom. And, you know, one thing that he says Ray that I'm sure you’ll agree with too is, you know, as an entrepreneur write down the things over the course of a week that you're doing. And then look at that list and say, you know, basically: am I willing to look at what I'm doing, these activities, and pay myself the $5, the $10 an hour that I could be paying somebody else. Like, is my time – am I saying that my time is only worth this $5 or $10?
If I am able to outsource these potentially redundant tasks – and once you kind of look at it that way and say, you know, if I'm not willing to pay somebody else $10, what I'm basically saying is that my time is worth $10 an hour. And as an entrepreneur, you're not going to get very far very fast with that mindset, so. Great stuff Ray. And let’s kind of shift right now. You know, let’s shift to a story of your journey, Ray. And we're gonna talk about the great successes, and the wonderful epiphanies, and ah ha moments that you’ve had, but let’s first start with a failure. You know, let’s start with a struggle, a challenge that you’ve faced. And let’s really talk about that moment and the lessons you learned.
Ray: Yep. And it's hard to think of just one because as an entrepreneur I fail at something all the time, probably every week. When I started to do PR, I failed at it. When I started social media marketing, I failed at it. If you asked me for my biggest failure, it's probably after I left BlackBerry and decided to become an entrepreneur. And I was really fortunate to join forces with my cofounder Keith Barney, who’s a really amazing individual and always keeps me motivated. But we were a bit over ambitious and probably naive. We wanted to do three products at the same time. And we thought by sharing the efficiencies of a common code base and infrastructure that we could build, market, and grow three different products simultaneously.
And perhaps we fell victim of looking from the outside in and thinking it was easier than it actually is. But it ended up being probably five times harder and five times more expensive to build a product and a company around it. So yeah, we ended up folding up that business and that effort. And late last year, we decided of those three endeavors, SpeakUp was for sure the highest potential. And that for us to be successful, we had to focus not just full time, but more than full time on that product specifically in building an awesome company around it.
John: So Ray, you’ve mentioned my favorite word a number of times: focus. You know, the acronym that I love with this word is: follow one course until success. You know, not follow three courses. And, you know, it's pretty interesting that you went in with the mindset number one that: hey, you know, we're gonna try these three different opportunity. You know, we're going to diversify. We're going to hedge our bets. You know, maybe one of these will take off. But the reality was is that none of them were able to take off because none of them were able to get the focus from the two of you that was necessary to make that happen.
And that’s a mistake that so many entrepreneurs make when they first start. You know, they just don’t have that focus and they just try to hedge their bets and spread it out. You know, what would you say Ray, to entrepreneurs right now that are saying, “You know, I have a couple great ideas. You know, I really want to maybe test them out and see what works.” Like, what would you say to that entrepreneur that’s listening right now?
Ray: First of all, don’t do a damn thing until you read The Lean Startup.
John: Right. Or listen to the interview that we did with Eric Ries that was very powerful, too.
Ray: There you go. So that’s number one. Number two is: don’t start building, start learning. And you really have to validate the concept. Go look at the market. Go look at the competition. Go do some stuff that entrepreneurs aren’t good at doing, which is discipline research and analysis, necessarily. Entrepreneurs, a lot of times, myself included, just want to go, go, go. But when you're thinking and in you're in the ideation stage, before you invest time and money in building something, it's really important to look at all of the factors that can lead to your success or failure. Be super objective about your chances.
Don’t fall in love with an idea, and then go after the one that makes the most sense and that you're the most excited about, both. It has to be a blend. It can't be one or the other.
John: So here’s the interesting question. You know, and this something that I actually get fairly often, you know, from my listeners when they write in about an idea they’ve had, or about something that they're pursuing. You know, that’s always one of my first questions is: well, did you go check out the competition? You know, did you really study them? You know, what are they lacking in? Where are their flaws? And I sometimes get the response back, “Well, John, this is actually so blue ocean. There's just no competition.” Like, what are your thoughts when you hear people say things along those lines?
Ray: It's – it's – yeah, I think it's naive. I mean, there's always competition. You can execute better. You can do a different flavor of something. But it's just starry eyed interests, or passion for an idea and it's just not real. So I think it's a disciplined mental endeavor to go through and think: okay, this is what I want to do. How do I stop and actually evaluate the marketplace, the circumstances, and then properly think about what our chances of success are, and then pursue it or not accordingly. And in fact, I knew a really analytical entrepreneur that was about to start his own endeavor.
He went through that exercise and decided not pursue it. So think how amazing that it? Think how much time and money he would have wasted if he didn’t do that exercise and pursued it without it being viable. So I think it's worthwhile for sure.
John: Now, and if you are in that very tiny percentile, you know, somehow, someway, where there's just really that much, or any competition, you know, that in of itself in my opinion is a red flag, Fire Nation. There's probably a reason why there's no or little competition because there's not really a viable business there. Because if there was a viable business, believe me there would be some competition. And so often Ray, I get emails from entrepreneur that say, “John, like I had this great idea. I'm so excited about it. And then I Googled it and somebody’s already doing it.”
Like, ho hum, like my life’s over, like back to the drawing board. And the reality is: listen, that’s actually a good thing. That’s proof of concept. That means that there's people out there paying for it, now you go find what those mistakes are. You know, go read the reviews, the 1-2-3 star reviews about that company, if there are any. You know, and get the knowledge of what's lacking. You know, use those products and services, see what you want, and see how you can bring something unique and different to the market. And Ray, what I want to do with you now is go to another story. Go to the other end of the spectrum, away from a failure, and talk about an epiphany, an ah ha moment, a light bulb that you’ve had at some point in your journey?
So take us to that story, Ray. Share with us that moment in time of that ah ha moment, and then walk us through the steps you took to turn it into success.
Ray: Sure. So both – there's actually two ah ha moments. And one lead to the other and they both culminated in SpeakUp. So as I mentioned, SpeakUp is all about employees being able to create a positive change at work on one hand, and then on the other hand management being able to make better decisions and improve the company based on that input. So on the employee side of things; I remember a situation where we were launching a new Smartphone at Blackberry. And was building the sales plan, and about to go collect purchase orders for a huge amount of money and a huge amount of units. I came to find out that we did not have a marketing plan, so not that there wasn’t a good plan, like we literally had no plan.
And it seemed like no one really was paying attention to this, and no one really drew any attention to that matter. So I literally chased down my boss’ boss in the airport after sending him an instant message. And then had coffee with him and let him know. And it was news to him as well. So I just wondered what would have happened to my sales results, the result of the profit and loss for that region if I hadn’t flagged that, if we hadn’t resolved it in time, and what would have happened, you know, if I didn’t. So that was me, and I was always sort of on the verge of either being promoted or fired because I had that aggressive attitude at work.
But not everybody one else does, so that kind of was sitting at the back of my head. How do we make it easier for people to flag problems with the higher-ups? How do we make it easier to share great ideas? Nothing really became concrete at that point in time, but where it really did come together for me was when I was in the position as leader of a business. So coming into the role in Australia and New Zealand as the new MD, I wanted to change the culture. And I wanted the team to provide me with great feedback and to help me make better decisions with their, you know, collective wisdom, and with their awesome input.
I was wasting tons of time doing things the old way; calling meetings, having off sites, doing all these very manual endeavors. And over the course of a couple of months I did change the culture, but the only problem that occurred after that was I was absolutely inundated with feedback. And I had no way of sorting through it, and it became an administrative nightmare. Ad I thought to myself: why is there no systematic way to capture and curate the best thinking from my team? Why is there no software that can help me do this in a really simple way, where everyone can participate?
And then, I can in a very transparent manor, let people know what decisions I'm making when and why? And that’s when it really struck me: okay, SpeakUp, we've got to pursue this idea. The name wasn’t SpeakUp. The idea was really rough. Keith Barney, my cofounder, contributed hugely to, you know, solidifying the idea and helping us brand it, and market it, and build it into what it is today. But that’s where the ah ha moment came from.
John: Wow. I just love that phrase: on the verge of being promoted or fired. I mean, it's so funny because in that scenario, I mean, we're definitely brothers from another mother. Because it seems like my entire corporate stint that I had in many different industries, that was always me, you know. It was either my boss, who was singing my praises, or just like: John, are you serious? Like, what? And it's just like – that was just always me. Like, I was always hard charging straight ahead, and it was either a homerun, or it was an absolute strikeout. And I'm actually the same way today. I mean, Kate will tell you that, you know, I either hit a homerun, or it's an absolute strikeout, and she deals with it, so that’s cool.
But it's kind of funny that that just seems to be a lot of times that type A entrepreneurial personality that, you know, you're just on that verge of wither just knocking it out of the park or just falling flat on your face. And you know what? That’s okay because we can get up when we fall on our face, Fire Nation. And Ray, what I want to do with you now, is have you share another story. This is going to be your last story. But take us to the moment in time that you consider your proudest entrepreneur moment.
Ray: That’s easy. Probably the proudest moment in my life is when SpeakUp became reality. So I remember the day very specifically. I remember the goose bumps that I had, the adrenaline dump when we on boarded our first beta customer for Speak Up. It was months and hundreds, if not thousands of hours of work, and tens and hundreds of thousands of dollars all coming together into one moment, to see if what we did actually works technically and functionally. So imagine what that felt like when it did on both fronts.
And not only was the system working and things weren’t breaking and crashing and falling apart, but people within our first beta company were for the first time having their voice heard across continents, from Northern Europe, to Canada, to the U.S., and sharing ideas that no one had talked about before within their company. And this is a company that we did a case study about called DDS. They're in the digital dispatch service industry, which is, you know, they're the ones that do the hardware and software for taxi cab companies. And needless to say, they’ve got a challenge at the moment with the, you know, Ubergs and Lists of the world coming into play, so they need great new ideas, so they can stay relevant.
And in terms of building their app, and being able to take payment mobile, and being able to book from mobile, all those ideas are being discussed and voted upon within SpeakUp, and it was so awesome to see that for the first time.
John: So Ray, you talked about The Lean Startup and the MVP, that minimally viable product, you know, what did you do to actually prove the concept of SpeakUp, you know, before spending these hundreds of thousands of dollars and all these hundreds of hours, like what did you guys do?
Ray: So I first – I have to be honest firstly, we did not stick to The Lean Startup as well as we could have. It is a very difficult and disciplined thing to do. We had too many features in the first product. Luckily it worked, and it was a bigger bet than it should have been, and so far we're off to the races and things are going great, but we for sure could have been leaner. So I’ll just get that out there, so I'm clear. The other thing is we did go through the process before starting to build, of talking to really smart people. And making sure that from an industry analysts’ perspective, we are hitting an area that needs to be served, it's currently being underserved, which we validated by talking to smart people at Gala, The Engagement Kings, and McKenzie, really brilliant consultants, and even Korn Ferry HR pros.
So we did that, and then beyond talking to we also talked to companies and customers. So hey, guys, am I alone in this in that as a leader I want better ways to capture and curate information from my team? And employees that work for companies: would you like a form by which you can have your best ideas heard and solve company problems? And the answer was a resounding yes, yes, yes, and so much excitement. And not just from people we knew that wanted to be polite, but from strangers as well. So all of those things helped us validate the concept before we started building, but as I said, we could have built in a more efficient way.
And down the road, when we do our next endeavor many years from now, we certainly will be more frugal with the way we build, and measure, and learn.
John: So Ray, you dint follow The Lean Startup principles as close as you could, but let’s just be honest, there's not always every situation where you're able to do that because things do need to get built out. And when you're looking at as big a scale as you are, that’s just a reality. You know, sometimes you just need to make some assumptions and hope for the best. You know, we're not always going to be able to prove every single model before we launch. I mean, before I launched Entrepreneur on Fire, like I couldn’t prove that people wanted a seven day a week podcast.
Like, it had to actually be out there for people to say: you know, yeah, I'm gonna listen every single day, for me to actually see that because, you know, people will say one thing, but they vote with their actions. They vote with their wallets. And that’s just a reality Fire Nation. So do what you can, but don’t hold yourself, you know, to this impossible goal of being 100 percent MVP. And Ray, I want to bring things to today and talk to you right now about the one thing that’s most exciting you today?
Ray: It is such an incredible journey to run a company. It is a wild ride. It is up and down, in terms of an emotional rollercoaster. At the moment we're riding really high because things are going great. And we've been publically released now for about two months. And we've been growing really nicely. So I think the most exciting part about business right now is when I wake up in the morning, and I pull out my phone, and I open up an email from Intercom. And I look at all the people that signed up the day before, and all of the awesome brands that we're attracting to SpeakUp because it's validation every single morning that we're on to something, and companies want what we're offering, and they're signing up in droves, so it feels fantastic.
John: I love that. So Ray, we're gonna enter the lightning round, but before we do, let’s take a minute to thank our sponsors. Ray, welcome to the lightning round, where you everything to share incredible resource sand mind blowing answers. Sound like a plan?
Ray: Sounds good.
John: What was holding you back from becoming entrepreneur?
Ray: Well, I've always been an entrepreneur in my opinion. You might have called me an intrapreneur at my past company in my past roles. But the fact is, at BlackBerry I was able to dream up wild stuff. I would take massive budgets and I would build new businesses. And my needs were being met. I was learning a lot. I was making a massive impact on the business and I was making great money. So I kept at it and it worked out really well for both parties. But as soon as one or more of things dissipated, and two of them in fact, I left BlackBerry and decided to move on and start my own business.
John: What is the best advice you’ve ever received?
Ray: I don't know if anyone has given me this advice directly, but I do love The Golden Rule, and I do apply it to business, and I think it's really important. I especially learned this in Asia, where the legal system and legal recourse isn’t as common in countries like Indonesia and Philippines because it's a bureaucratic mess. You are your word and your reputation and your history. So if you treat other people the way you wanted to be treated in business, and you never try and screw someone over, and you always give them a fair deal, and you're always looking out for win-win, people want to do business with you.
And that’s treated me really well over the years and I recommend that everybody operate in the same fair manor.
John: The Golden Rule, Fire Nation. Ray, share one of your personal habits that you believe contributed to your success.
Ray: I’ll share two. So one is maybe a bit controversial, but it works for me. I don’t drink alcohol. I don’t get wrapped up in partying. I don’t do things that are detrimental to my personal health goals, or my goals in my business. And for me, alcohol has always been a distraction, so I completely avoid it 100 percent. I'm always clear minded and I'm always in control as a result of that, and I can spend my time on ultimate productivity, so that’s number one. And then speaking of being productive, I don’t look at the work week as a 9:00 to 5:00 Monday through Friday. I look at available chunks of time to get stuff done. And that could be six days a week, seven days a week.
It could be at 11:00 a.m., it could be at 1:00 a.m. So I just think having that mindset of getting stuff done based on your plan and based on your objectives and priorities is super crucial.
John: Ray, do you have an internet resource like Evernote that you can share with our listeners?
Ray: Yeah. There's this tool out there called intercom.io, which I'm sure a lot of you have heard about. It was kind of unclear to me at first what it did, but when we started using it up for SpeakUp, definitely decided it was the right tool and we picked the right one. It enables you to manage your customer base essentially. So I mentioned an email that I get in the morning about new users, it's from Intercom. They tell you who signed up from what company, how many from that company? And you can send them messages on an automated or manual basis based on preset conditions that tie into your app. So it's just a really awesome clean and simple way to manage your customer base.
John: Cool. If you could recommend one book for our listeners Ray, what would it be and why?
Ray: I have to give you two, I'm sorry. The first one would be The Burned-Out Blogger’s Guide to PR. X-tech crunch blogger called Jason Kincaid wrote this, and it is spot on. I'm reading this book just nodding the whole time about the PR pitfalls you're going to encounter, and the ones you should avoid as you're building your business. So love it, it's a quick read. Jason’s a good guy. I definitely recommend that one. The second one is a bit old school, but it's such a brilliant book. It's by Larry Bossidy, I think, it's called Execution. And it's all about focusing on people, your strategy, and operations that connect people to strategy in business. So in terms of honing the way you think big picture, Execution is a great way to do that.
John: Well, Fire Nation, I know that you love audio, so if you haven’t already, you can get an amazing audio book like this for free at eofirebook.com. That’s eofirebook.com. And Ray, this next question is the last of the lighting round, but it’s a doozy. Imagine you woke up tomorrow morning in a brand new world, identical to earth, but you knew no one. You still have all the experience and knowledge you currently have, your food and shelter taken care of. But all you have is a laptop and $500. What would you do in the next seven days?
Ray: Well, assuming that I'm in Orange County, which is where I am now. I would go to the airport and I’d buy a ticket to San Francisco. And I would go there, and I would attend as many meetings as I could in the startup community. And I would meet really smart advisors, I’d meet developers, and I’d meet designers. What people say online about San Francisco being a very special place to start a business is absolutely true. To the point where my first couple of trips prompted me to get a second place up there and now I spend half of my time in San Francisco. There's just a really special vibe up there, and a lot of awesome smart people doing interesting things that genuinely want to help you out.
So it's such a great place to be if you're trying to start a new company. I would go there first thing and I would meet an awesome designer, meet an awesome developer if possible. Get together and build a team and then decide on which idea to pursue after careful analysis, and then I would start another company.
John: Well, Ray, let’s end today literally on fire, with you sharing one parting piece of guidance, the best way that we can connect with you, and then we’ll say goodbye.
Ray: Yep, let’s see. I – my piece of guidance is to not be a paycheck collector, or to not be a mercenary, and they're kind of the same thing. So it's a matter of caring about what you do. You're only on this planet for so long. There's only 168 hours in a week. If you're looking at a job as a means to an end, you show up, you punch in, you do the work, you get paid, then you can enjoy your time off. You're wasting over half your time, in my opinion. So if you can find some way to get some value out of that, or to actually make a contribution. Make yourself feel good, make others feel good, have an impact in some way on business or on the world.
I would definitely recommend doing that, whether that’s working for someone else or working for yourself. So that’s my piece of guidance. Don’t just show up and put in the time, really work hard. And part of that also, by the way is, nowadays especially, hard work is a trait that’s becoming harder and harder to come by, and so if you can outwork people, even if they're smarter than you, you can excel and you can accomplish more than them. So work hard and work on stuff that matters, I guess, is the summary of my advice.
John: And what's the best way we can connect with you?
Ray: You can email me directly. My email address is email@example.com. And you can also checkout our website and signup for SpeakUp for free at getspeakup.com.
John: So Fire Nation, you are the average of the five people that you spend the most time with. And you have been hanging out with Ray and myself today, so keep up the heat and head over to eofire.com, type Ray in the search bar. His show notes page will pop right up with all of his greatness. And of course, check out getspeakup.com, or Ray very generously offered firstname.lastname@example.org, his email. So Ray, thank you my friend for sharing your journey with Fire Nation today and for that we salute you, and we’ll catch you on the flipside.
Ray: My pleasure John, thank you.
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