The Exchanges

Q I want to discuss then the time as a restaurateur. Of all that, that was an interesting bit for me to choose. But I want to discuss the time as a restaurateur, and you said there were many lessons that you took from that. What were the big lessons that you took from that very hard physical time as a restaurateur, and how did you apply that to Hootsuite today?

A Yeah, so, you know, working as a restaurateur or a small business owner in general, you know, I talk about small businesses are fantastic because ultimately full accountability rolls up to you, one person. You have to Ultimately develop a skill set. You have to be good at a lot of different things. So you have to be, you know, the, the marketer, the salesperson, the operations person, the janitor, you know, ultimately everything when you're, when you are a small business. And so that is a mini MBA. I think what you, you do also learn out of it is, you know, what are your core competencies? What do you like doing the most? How do you ultimately find people and backfill people into areas that, that you're not passionate about? And as I've looked at what I'm doing today in terms of managing a nearly thousand person company, I did develop a holistic skill set in running my restaurant. I figured out the areas that I am passionate about and areas that I need to backfill and to get other specialists in. Look, in terms of, like, just take finance. I know how to read an income statement, a balance sheet, a cap table. But it's not my passion. If I, if I had to do that every day, you know, I wouldn't be the happiest Ryan, but I have a CFO and guess what? He loves doing that. And, and the finance team, they love doing that. That's their passion. And so the great thing about humans is that …

AI assessment note: “I figured out the areas that I am passionate about and areas that I need to backfill”

Q myself am having, and it's As the boss of a small business, and as it grows, how do you look to then retain that same creativity? You said about a thousand people. Insanely busy, I'm sure, your schedule. How do you look to retain the same creativity and entrepreneurial mojo that you had at the beginning of the journey? Are there any elements that really allow you to retain this?

A Yeah, well, I think when companies lose that entrepreneurial spark, that's the day that they start to die, and if you think about, there are so many large organizations, you search and search for what people call a cash cow, you know, what is a great economic engine to fuel your business, and what I believe happens is once you find that cash cow, that economic engine, you bring in systems to make sure that the The engine stays healthy. You bring in processes to make sure that it doesn't get accidentally turned off. So you bring in legal aspects, policy, compliance, security, and all of these other great parts of a business that are important. But the risk of that is that you over systemize and you ultimately, I think, demotivate people that are more entrepreneurial thinkers. And so you need to create an area, I believe, where the Those types of people can think outside of the box and, and not get punished for that or not get chastised for that. You know, we have in our business, we started at a, I think an early age, we started a labs division of our company. Everybody is responsible and accountable for, for some innovation. And we don't tell everybody, you know, that isn't in the labs group to turn off your entrepreneurial mind or your, your innovative mind. But people that work in that division get a little bit of extra You know, that we don't demand the same legal compliance…

AI assessment note: “we started a labs division of our company. Everybody is responsible and accountable for, for some innovation.”

Q I want to discuss then the time as a restaurateur. Of all that, that was an interesting bit for me to choose. But I want to discuss the time as a restaurateur, and you said there were many lessons that you took from that. What were the big lessons that you took from that very hard physical time as a restaurateur, and how did you apply that to Hootsuite today?

A Yeah, so, you know, working as a restaurateur or a small business owner in general, you know, I talk about small businesses are fantastic because ultimately full accountability rolls up to you, one person. You have to Ultimately develop a skill set. You have to be good at a lot of different things. So you have to be, you know, the, the marketer, the salesperson, the operations person, the janitor, you know, ultimately everything when you're, when you are a small business. And so that is a mini MBA. I think what you, you do also learn out of it is, you know, what are your core competencies? What do you like doing the most? How do you ultimately find people and backfill people into areas that, that you're not passionate about? And as I've looked at what I'm doing today in terms of managing a nearly thousand person company, I did develop a holistic skill set in running my restaurant. I figured out the areas that I am passionate about and areas that I need to backfill and to get other specialists in. Look, in terms of, like, just take finance. I know how to read an income statement, a balance sheet, a cap table. But it's not my passion. If I, if I had to do that every day, you know, I wouldn't be the happiest Ryan, but I have a CFO and guess what? He loves doing that. And, and the finance team, they love doing that. That's their passion. And so the great thing about humans is that …

AI assessment note: “I figured out the areas that I am passionate about and areas that I need to backfill”

Q myself am having, and it's As the boss of a small business, and as it grows, how do you look to then retain that same creativity? You said about a thousand people. Insanely busy, I'm sure, your schedule. How do you look to retain the same creativity and entrepreneurial mojo that you had at the beginning of the journey? Are there any elements that really allow you to retain this?

A Yeah, well, I think when companies lose that entrepreneurial spark, that's the day that they start to die, and if you think about, there are so many large organizations, you search and search for what people call a cash cow, you know, what is a great economic engine to fuel your business, and what I believe happens is once you find that cash cow, that economic engine, you bring in systems to make sure that the The engine stays healthy. You bring in processes to make sure that it doesn't get accidentally turned off. So you bring in legal aspects, policy, compliance, security, and all of these other great parts of a business that are important. But the risk of that is that you over systemize and you ultimately, I think, demotivate people that are more entrepreneurial thinkers. And so you need to create an area, I believe, where the Those types of people can think outside of the box and, and not get punished for that or not get chastised for that. You know, we have in our business, we started at a, I think an early age, we started a labs division of our company. Everybody is responsible and accountable for, for some innovation. And we don't tell everybody, you know, that isn't in the labs group to turn off your entrepreneurial mind or your, your innovative mind. But people that work in that division get a little bit of extra You know, that we don't demand the same legal compliance…

AI assessment note: “we started a labs division of our company. Everybody is responsible and accountable for, for some innovation.”

Q mold into. And I'd love to hear your take on, on Reid Hoffman's statement of, if you're not embarrassed of your first ship, shipping of the product, then it's too late. So, so to what extent do you agree with this? Uh, and then I'm intrigued to hear how easy it is to build a business model around a product that's not built to scale kind of from the start.

A Yeah, you know, I, I really believe in that statement. You know, early days, you have nothing to risk. Do you, Are scrappy. You're iterating quick. You should be getting something out the door and testing that people are using it and loving it. That's effectively, you know, what we did for, for Hoosuite one point. Oh, I, I actually should ask my team if we have any screenshots around, but we would, you know, today we would be, I'm sure, embarrassed by it. As you grow user base, we have an accountability for dependability, reliability to them. We have an accountability, uh, you know, we have effectively Provided our customers with a product and a workflow that they're familiar with, and so rapid shifts in product, turning the big ship on a dime is less possible, and also, I think, maybe irresponsible. And so, you have to think about strategies in terms of how you can do things like dark launches, A-B testing, segmenting, and other strategies like that, where you're able to, you know, get insight and allow a few, you know, users, you know, beta releases to To, to play with product without effectively unveiling it to your, your whole customer base and user base. We have a lot of strategies that we do for this because we are dealing with a very broad user base. We do do things like dark launches and, and also beta upgrades, which are a hugely successful strategy for us. Letting our…

AI assessment note: “I really believe in that statement. You know, early days, you have nothing to risk.”

Q mold into. And I'd love to hear your take on, on Reid Hoffman's statement of, if you're not embarrassed of your first ship, shipping of the product, then it's too late. So, so to what extent do you agree with this? Uh, and then I'm intrigued to hear how easy it is to build a business model around a product that's not built to scale kind of from the start.

A Yeah, you know, I, I really believe in that statement. You know, early days, you have nothing to risk. Do you, Are scrappy. You're iterating quick. You should be getting something out the door and testing that people are using it and loving it. That's effectively, you know, what we did for, for Hoosuite one point. Oh, I, I actually should ask my team if we have any screenshots around, but we would, you know, today we would be, I'm sure, embarrassed by it. As you grow user base, we have an accountability for dependability, reliability to them. We have an accountability, uh, you know, we have effectively Provided our customers with a product and a workflow that they're familiar with, and so rapid shifts in product, turning the big ship on a dime is less possible, and also, I think, maybe irresponsible. And so, you have to think about strategies in terms of how you can do things like dark launches, A-B testing, segmenting, and other strategies like that, where you're able to, you know, get insight and allow a few, you know, users, you know, beta releases to To, to play with product without effectively unveiling it to your, your whole customer base and user base. We have a lot of strategies that we do for this because we are dealing with a very broad user base. We do do things like dark launches and, and also beta upgrades, which are a hugely successful strategy for us. Letting our…

AI assessment note: “I really believe in that statement. You know, early days, you have nothing to risk.”

Q about constraints, I'm intrigued to hear with a company like Hootsuite, how do you approach product in terms of, there's numerous amounts of features that you would like to do and push through the funnel. How do you choose which ones go through the funnel and which ones don't? And then once out in the market, which have product market fit and which don't? How do you approach that element?

A That's, you know, an age old question and something that we love. And I think in the world of social, the, the transparency, customer transparency is so incredible. You know, we, we push updates and we hear back immediately from our customers, whether they love and hate it. And, and, you know, we, we do always try to get informed customer decision and feedback at, at the forefront of releasing new product. But sometimes when you're working with an agile and rapid release environment, you just want to get it out and, and let people play with it. And, you know, there also is this friction of done perfect or, or done. And sometimes you, you know, we want to do something that we believe is a, is a bit of an epic and it's going to take a lot of time to get that out. And it's not going to be possible to get a micro release out around it to gauge what the, you know, what customer's response to it is. So, you know, I, I think it's a blended approach. I don't think that there's any one right philosophy. I think sometimes we'll, we'll do longer sprints on, on projects or multiple sprints on projects. And, and other times we'll do, you know, tighter, quick release, validate and, and feedback. I think we also, you know, want to bucket into, is this a feature? Is it a usability, uh, issue and, and trying to figure out which, which kind of balancing we put into, like, do our customers concer…

AI assessment note: “I think it's a blended approach. I don't think that there's any one right”

Q you realized that you had to fund the machine that is Hoosuite. So I'm intrigued to hear how the fundraising game was for you, and what you think you did particularly well at, and where you'd like to improve with, with another startup, be it the, the standing desk, or another startup in the future. So, so what did you do well, and what would you like to improve on?

A So the time that we were fundraising, you know, it was 2008, nine. It was, you know, in terms of the capital markets, I think that it was an all right time. I think over the, you know, the last year was one of the best times ever. And I still think that it's a fairly good time to be fundraising. I think that there right now is an appetite and a theme around profitability path The profitability. I think that people are battening down the hatches a little bit. Cashflow breakeven is important for a lot of larger and later stage companies like ourselves. But, you know, I think that it is a, is a great time. So when we were fundraising in 2008, nine, I ended up, we were headquartered in Vancouver, Canada. There were not, and was not a level of sophistication in Vancouver around social media, let alone cloud and SaaS. So ultimately ended up going to San Francisco and New York. There were a number of early day competitors that had recently gone through, done their tour, and got funded up. So unfortunately, we were kind of like the number fourth coming along, and a lot of people just were, they had already seen the show and talked to people. You know, our slant on it was a little different. A lot of people, uh, you know, early competitors, TweetDeck, Seismic, CoTweet, those were, as I said, early, early competitors. They were more focused on building a social browser, a consumer-based …

AI assessment note: “our slant on it was a little different”

Q about constraints, I'm intrigued to hear with a company like Hootsuite, how do you approach product in terms of, there's numerous amounts of features that you would like to do and push through the funnel. How do you choose which ones go through the funnel and which ones don't? And then once out in the market, which have product market fit and which don't? How do you approach that element?

A That's, you know, an age old question and something that we love. And I think in the world of social, the, the transparency, customer transparency is so incredible. You know, we, we push updates and we hear back immediately from our customers, whether they love and hate it. And, and, you know, we, we do always try to get informed customer decision and feedback at, at the forefront of releasing new product. But sometimes when you're working with an agile and rapid release environment, you just want to get it out and, and let people play with it. And, you know, there also is this friction of done perfect or, or done. And sometimes you, you know, we want to do something that we believe is a, is a bit of an epic and it's going to take a lot of time to get that out. And it's not going to be possible to get a micro release out around it to gauge what the, you know, what customer's response to it is. So, you know, I, I think it's a blended approach. I don't think that there's any one right philosophy. I think sometimes we'll, we'll do longer sprints on, on projects or multiple sprints on projects. And, and other times we'll do, you know, tighter, quick release, validate and, and feedback. I think we also, you know, want to bucket into, is this a feature? Is it a usability, uh, issue and, and trying to figure out which, which kind of balancing we put into, like, do our customers concer…

AI assessment note: “I think it's a blended approach. I don't think that there's any one right philosophy.”

Q And then talk to me about the next five years for you and for Hootsuite. What's in the roadmap ahead?

A Yeah, next five years, you know, we're, it's, it's kind of mind-boggling to think, you know, we're just over seven years old. Next five, where does this go? And, and we couldn't have imagined getting to where we are today, uh, on the product. You know, I think we just continue to help Service our customers. And with regards to the ecosystem, I think that we've seen the customer now, every interaction point is in social. So whether it's from discovery through marketing, through sales and social selling, or on the other end, customer support and creating customer advocates, that is, you know, where people are gravitating towards is social. And so brands need to go there to help their customers. And so we want to help them with that The full journey, the full customer experience, and that's really just where we're focused.

AI assessment note: “we want to help them with that The full journey, the full customer experience”