Ryan Westwood: The Entrepreneur’s Entrepreneur

I love helping other entrepreneurs.

Ryan Westwood exudes passion like Mark Zuckerberg writes billion dollar acquisition checks. It’s awe-inspiring, exhilarating, and never-ending. Westwood is the founder and CEO of two successful Utah-based companies — PcCareSupport and Outbox Systems — which sounds exhausting, yet he manages to muster up more energy than a budding entrepreneur still trying to prove himself.

More than anything, though, it’s Westwood’s willingness to help foster Utah’s startup ecosystem and mentor up-and-coming entrepreneurs that made us want to tell his story.

We caught up with Westwood over burgers recently to learn more about PcCareSupport, Outbox Systems, and his background.

In 2010, while working as the Senior Director of Sales for AtTask, Westwood decided it was time to start his own company.

“Since I was a little kid I wanted to be an entrepreneur,” said Westwood. “We had a bit of a fantastic fourth quarter. Everything was going well at AtTask, and I got to the point where I had built up enough of a runway that I thought I’ve got to go do this.”

Although the company has since pivoted, the original idea behind PcCare Support was to provide technical support to companies with less than 50 employees.

“When we started out, we only had $5,000. We really had no marketing budget, and we had some really crazy things happen,” said Westwood. “At one point we decided the only way we’re going to grow is through trade, so we went out and we traded with radio stations. The radio stations ran the ads and we supported their computers.

“One day we got a call from this old lady who had heard the radio ad. At this time I was at home on my cell phone and we used a phone booth, or one of those systems that make it sound like you’ve got more than one employee — callers are asked to press one for sales, press two for something else, and it’s really just me on the other end of each button; there were only three or four of us. Anyway, I helped this lady for 30 minutes for just $15 a month. I remember getting off the phone thinking, oh my gosh. This isn’t going to happen. If it takes that long to get $15 a month, we’ve got a problem.

“About a month later we got a call from this guy who said, ‘You really helped out my mom. You spent a lot of time with her. Your service was awesome. I’m the Vice President of Operations for the largest wireless provider in America and we want to work with you.’

“He actually started out by saying, ‘I want to buy you.’ I had to explain to him there wasn’t anything to buy, but that we wanted to partner. We put our heads together and worked out an agreement, and that partnership was the catalyst for massive growth for PcCareSupport.”

Ernest Hemingway famously once told his son Gregory, “You make your own luck, Gig. You know what makes a good loser? Practice.” It’s hard to get lucky as an entrepreneur. You have to put yourself out there and be willing to do almost anything to sell your product or service. At some point you have to stop talking, begin doing, forget about the term “beta version,” and take a risk on yourself and your company. Westwood’s story may sound like pure luck, but it’s important to understand how difficult it is to put yourself in a position to receive a lucky break.

“It was a combination of providing a really good service, a little bit of luck, but at the same time we could have given up without a marketing budget and put our hands up and said there’s nothing we can do. Instead we decided we’re going to go after this, and if it means trading with every radio station out there we’ll do it,” said Westwood.

Like most startup stories, PcCareSupport came about because Westwood saw a need that wasn’t being fulfilled by somebody else and decided to do something about it.

“We really did see that small business was neglected,” said Westwood. “There was phenomenal support for companies with more than 50 employees and the consumer. But if you were a small business owner and you couldn’t afford an IT guy, but you really needed top notch support it just wasn’t … we didn’t see it readily available. Since then we felt like the consumer side was also neglected. Geek Squad, no one nowadays wants to leave their computer at a Best Buy for a week. Nobody even wants to wait 24 hours for one of their cars to show up. People want instant help.

“The other stigma with the industry is people did not want to be overseas. The two things we did is we said no hold times — our customers do not wait on hold, and it’s going to be U.S.-based. We charge a premium, but our customers get U.S.-based, no-hold-time tech support. I think that people have enough frustration with the technology, let alone the language, that they’re more than happy to have someone right here, right now, with no hold time to help solve the problem.”

Most of PcCareSupport’s customers are older than 45, which allows the company to focus not just on support but also education.

“We provide ongoing webinars. We have a platform they can log-in to and watch videos. We educate them and support them. We’re trying to just help the older generation learn how to use their technology. They see these cool tools, and we want to help them use them,” said Westwood.

Marketing to the older demographic is currently working extremely well for PcCareSupport, but what happens when the younger generation becomes the older generation?

“We’re seeing that with the complexities of technology, more and more there’s still opportunities in younger markets,” said Westwood. “We’ve had to make some pivots. We’ve had to move into mobile phones and tablets. But the amount of support, the amount of problems caused by people, hackers, or whatever doesn’t seem to be letting up. It seems to be getting worse. I do think it has a shelf life. The business plan has a shelf life. Thirty years from now it’s not going to look the same. It would either have to be heavily evolved or sell.”

To this point PcCareSupport hasn’t raised any venture or private equity capital. To get the company off the ground they utilized debt financing and angel investors.

“We have angel investors. The way we did it is we had a strategic partner that we had worked with for quite some time who decided to invest in the business based on the success they saw. So we took a good investment from a company that was a strategic partner that owned an ISP,” said Westwood.

Last year, after launching Outbox Systems, a SaaS consulting and development firm, Westwood quickly began to look for strategic partners because he understood the value they bring to a company.

“With Outbox Systems it was easy to look at it and say, ‘Okay, where’s a problem in the market?’ We quickly realized we should focus on helping to build-up AtTask. They built project management software. So if a customer wanted to integrate their software with Salesforce that’s not what they do. We saw that opportunity. I think with learning from PcCareSupport, and the strategic partnerships we’ve developed, we immediately turned around and applied those same principles to Outbox, which was let’s find the right strategic partners that will help us grow. We signed three partners and all of a sudden it’s just catapulting. The business is quickly becoming as large as PcCareSupport,” said Westwood.

While he’s been incredibly successful at building and running two companies, what seems to excite Westwood most is working with fellow entrepreneurs to help them achieve their goals.

“I love helping other entrepreneurs,” said Westwood. “I just get stoked by that. I want to help other entrepreneurs get to market. I think a lot of entrepreneurs have great ideas, but they don’t know how to get them to market. I think that’s a pivotal piece in being a successful entrepreneur — getting your ideas to market.”

Westwood serves as the Entrepreneur-in-Residence at Utah Valley University, which allows him to speak to a lot of startups and founders.

“When I talk to startups their issues are usually 1) they don’t know how to get to market, 2) they don’t have the money or know how to get the money, and 3) they don’t know how to get the talent that they need. They don’t understand how operating agreements work. They really don’t understand how employee stock plans work. I think that if they could understand those things it would really help. If they can pitch their vision and know how to give up the equity in an appropriate way, but they have problems with those areas. I love being able to help them out anyway I can,” said Westwood.

Spend any amount of time with Westwood and you’ll quickly come to understand he’s an entrepreneur’s entrepreneur. You may walk away feeling like you just downed a dozen 5-Hour Energy drinks, but his passion for startups and Utah’s entrepreneurial ecosystem is contagious and irresistible.

We can’t wait to work with Ryan Westwood to help cultivate Utah’s startup scene, and we’re looking forward to covering the continued success and growth of PcCareSupport and Outbox Systems.

Published 4/3/2014