The SaaS Podcast: Founder Interviews - Page 12

Reilly Chase, HostiFi

From Getting Fired to $10K MRR With a Bootstrapped SaaS

Reilly Chase is the founder of HostiFi, a SaaS platform that helps IT providers manage all their customers' networks from a single server. In early 2018, a listener of this show mentioned me in a tweet. He told me how the podcast was such an inspiration for him and that he was about to start his own SaaS business. He was a single founder, bootstrapping a SaaS business for the first time and he was learning to code as he went. And over the next few months, he started sharing what he was doing. I'd often see tweets or LinkedIn posts from him about what he had just tried, what worked and what didn't work. He was a completely open book and you couldn't help but root for him. Once he shipped his product, he got a few early customers but wasn't making a lot of money. But it was interesting to watch him from the sideline as he tried all kinds of things to grow. Around December 2018, he tweeted that one of his goals for 2019 was to be a guest on The SaaS Podcast. So I told him, get to $100K annual run rate and I'll invite you on the show. He told me that at his current growth rate, he could probably get there in about 2 years time. But I told him that based on what I'd seen of him, I was pretty sure he'd get there sooner. So that was the new year resolution he set on January 1st, 2019. But a week later, his life turned upside down. He was fired from his job because his employer didn't like him moonlighting. And he had some tough decisions to make. Eventually, he decided to go all-in with his SaaS business. He even sold his house to give him a longer runway. Now his SaaS product wasn't just a side-project, it was everything to him. And it was amazing to see how getting fired from his job gave him even more motivation to succeed with his SaaS. And in 8 months, he achieved the goal that we set together. His business is currently doing over $10K in monthly recurring revenue. And I'm delighted to have Reilly join me on the show.

Tope Awotona, Calendly

Calendly Founder Tope Awotona: Product-Market Fit After 3 Failed Startups

Tope Awotona is the founder and CEO of Calendly, a scheduling platform that eliminates the back-and-forth emails required to book meetings. Tope Awotona grew up in Nigeria and moved to the US as a teenager. After graduating from the University of Georgia, he landed a sales job at IBM and spent the next seven years in enterprise software sales. But he always wanted to be an entrepreneur. So he spent his evenings and weekends trying to build businesses. First, he read an article about PlentyOfFish.com making millions and decided to build a dating site. He bought domains, created a holding company, and purchased dating software—but never launched it because he lacked the skills and resources. His second startup was an e-commerce site selling projectors. He made some sales, but the margins were terrible and he had zero interest in projectors. His third startup was another e-commerce site, this time selling grills. Same problems: thin margins, no passion, no traction. Tope realized he was focused on "ways to make money" instead of solving problems he cared about. He told himself he wouldn't succeed unless he found a problem he was passionate about solving. It took another year before he found that problem. After wasting an entire day trading emails to schedule a single meeting, he searched for a scheduling tool. Everything on the market was slow, clunky, and poorly designed. He spent six months researching competitors, studying their user communities, and identifying what they did well and where they failed. Unlike his previous attempts, this time he went all in. He emptied his bank account, flew to Ukraine to hire engineers, and committed everything to building a better product. The bet paid off. Calendly launched in 2013 as a free product (not by choice—they ran out of money before building billing). That accident turned into one of the best decisions they never made. The freemium model combined with viral sharing made it easy for users to spread the product. At the time of this interview, Calendly was generating $30M ARR and serving 4 million users, largely bootstrapped. Tope's journey from three failed startups to finding product-market fit offers a masterclass in patience, persistence, and solving problems you actually care about.