Hey, my name is Scott Smith and I’m the CEO at CloudApp. We're a business that started in 2016, and our focus is on visual communication. So the idea is that most of the time, it can be really difficult to explain your point or get your point across using just text-based messaging like Slack or email, and you end up writing long emails or long messages that nobody wants to read and also similarly, we're all burned out from video meetings like Zoom and teams other kinds of tools. So if you could capture what you see on your screen and share it as a quick video, screenshot, or annotation, it'll show what you're talking about much faster. And so our business builds software for companies like Qualtrix and Zendesk, and Atlassian, as well as small startups of 1-2 people.
What is your long-term vision for CloudApp?
So we started off by building a simple and, over time, more powerful capture product that could capture anything that you saw on your computer and would be able to integrate in any workflow that you have. So we have integrations with Github, Atlassian, Zendesk, Slack, and quite a few others. Then, as you capture more of this information and these videos and put them into tools you care about, we want that information to start coming alive. We want it to be searchable. We want it to be transcribable. We want our information to inform how you work and be a more superhuman version of yourself. So basically, the vision of the product is to help people become super versions of themselves, get work done faster and be more productive and try to make work a more friendly, happy place rather than feeling tired, exhausted, and burnt out.
What inspired you to start your own company?
When I was working at Facebook, I'd been there through an acquisition of a company called Parse, and I was working on a new product, and the product was called Facebook At Work or Workplace. So it was basically like using Facebook as you would, but in a work environment - so messaging, communication, all that kind of stuff. And I would go out and I would talk to the CTO of a 5,000, 20,000, 100,000 person company, and they would say, "Hey, I'd love to try the product. Can you send me some more information?" And anytime that I wanted to show what we were working on, my process would be - take a product like Quicktime, record a huge video, like 5 or 6 GB, try to figure out how to compress it and I would go to the tools available at Facebook like Box, Dropbox, maybe Zoho and a couple of others and upload it to that tool and then try to share that content out and make it external. And every time the videos were huge, they weren't transcoded, meaning you couldn't watch them on whatever platform you wanted to be on - mobile, web, or desktop. So sharing the files became kind of complex and cumbersome. So anyway, what was really, to me, was part of the idea with CloudApp was that every aspect of that flow I mentioned was instantaneous and easy to do for just about anybody. So that was a big reason that I thought, "Hey, this could be really cool," and I think as we developed it over time, we saw more and more people had similar problems - just wanting to get their point across and be clear, consistent, and very fast.
What advice would you go back in time and give yourself when starting your own company?
I think it's hard to appreciate even now, but I think the one piece of advice I would give is to work just as hard still but understand and realize that the time horizon for making things work and work really well can often be longer than I would want. So the early version of Scott would be frustrated and annoyed and pained at the progress that I was making or seeing the company make. And I think the reality is knowing how long the company takes to make it work really well, be successful, get great customers, do the marketing exactly as you want, and eliminate the bugs in UX and UI problems, is just going to take a lot of effort and perseverance and a lot of persistence. So I would go back to early Scott and say, "Hey man, look, it's going to take longer than you think; keep working hard and keep chasing after this dream."
What part of building a successful startup do you think is the most difficult?
I think there are two things:
So I think the first one is - given the time horizon that I mentioned, it could take five years, it could take ten years, but if it's something that you're truly excited about and feel like is meeting the vision of your expectations, it's worth it. I think the hardest part is probably that every day, every week, is full of this sign wave experience where you wake up in the morning, and you have an email from an excited customer. Then you have an email from a customer later that afternoon that hates you and wants you to refund all their money and cancel their account. Then that evening, you're trying to either settle down and relax and get back some focus on your own time, and you get pulled into something that is pressing or important or life and death (or seems like life and death to the person working on it). And so the hardest part is navigating that up-and-down experience, maintaining your sanity, emotional well-being, and health, and still having the energy to go back the next day. So Mike Tyson likes to talk about how everybody has a plan until you get punched in the face. And I think that's like every day you wake up, and you get punched in the face, and you have to go back the next day and say, I'm ready for more, and that's kind of how I think about it.
Which CEO, past or present, inspires you most?
More recently, the CEO that I'm inspired by is Scott O'Neil. He is the former president of Madison Square Garden. He was the president of the 76'ers for a while, and one of the things that he said that I've continued to hold on to as something really important for our team, is when asked what (company) culture is, he says it's what we tolerate and celebrate. I don't think he came up with the idea, but he attributes that as his focus to help him determine what the right things for his team to be doing and what the wrong things are. Who should he focus on giving accolades to, and who should he think about moving away from? I think, ultimately, as CEO, you have your customers and your team, and both are like your customers. Your team needs to buy into and support and care about whatever you're doing. If you don't have any customers, you don't have any money, and then you can't pay your team, and if you don't have a great team, then making money doesn't matter because you can't build anything exceptional without them.
What do you think is the most important trait for entrepreneurs?
Persistence amidst adversity. So things are going to come up all of the time that are just really hard. You know - somebody is going to quit, there is going to be COVID, and you will have to navigate work from home, there will be a potential recession, and there will be a lot of questions. And you need to be someone who has the ability to keep going, has an even keel, and the ability to navigate smoothly through this experience. You know, when the waters are rocky, and you're being flung all over the place, you have to be like, "Hey, we're going to get through this," and tell the team that realistically, we can do it if we have a good plan and a strategy. So it's definitely just persistence. You've just got to keep going and don't quit. I mean, at some point, you might have to quit, but I think most of the time you're going to think should I quit every day, every week, or every month and most of the time, the answer is no, keep going.
What advice do you have for aspiring entrepreneurs?
So for aspiring entrepreneurs, I've talked to a bunch of them, and there are so many people who are right at the precipice of making the decision to leave their job at Facebook (or other huge company) or to leave their job at a later stage startup and do their own thing. And a lot of the time, I feel like we get back to this idea: Are you willing to be uncomfortable, and are you willing to take a leap of faith and trust yourself? If you understand that it's going to be hard and you have to do it for a long time, you should just do it. And like I love the Nike slogan of "Just do it." And really, that's it. Every part of being an entrepreneur is just taking that step.
So one of my favorite comic book characters is Batman; I think either he or one of the writers of the comic book series said, "Everything is impossible until someone does it." So that's how you have to think about your business and your idea. It's going to seem impossible. But as you take one step toward setting up your business, buying a domain, or talking to customers, it's going to make things feel easier. Then eventually, you're going to do it, and you're going to be successful.