Raphael Crawford-Marks, Cofounder and CEO of Bonus.ly, talks with host Justin Gray about dropping out of high school to work in tech, his experience bootstrapping a company, and his advice for aspiring entrepreneurs –– all on the the latest episode of Driven & Co.
Tell us a little bit about your current gig and what a typical day looks like for you.
Bonus.ly is a platform for employee recognition rewards and engagement. My typical day consists of a wide variety of things from sales to operations to strategy to product. We’re still a very small company. I have 18 people now, so I am involved in a number of different things. But more and more I’m involved at a higher, more strategic level and I’m less involved in day to day tactical decisions.
When you were a kid, what did you want to be when you grew up?
I wanted to be a professional baseball player. As I got older, my passion for technology and computer programming began to emerge, so in my early adolescence that switched to being a programmer on the NASA Mars missions. I had the great fortune of growing up in San Francisco, and in the mid-90’s there were a bunch of companies like Adobe and Macromedia developing CD-ROMs and multimedia applications. I ended up dropping out of high school and started working at some of these companies, initially as a software tester and then later the software engineer.
When the whole dot com bust took place, was that your queue to exit the tech space?
Yes. After having spent basically all of my teenage years working rather than doing what most normal teenagers do, I felt like it was time to go back and do something normal for a change. It was kind of coincidental that the dot com bust happened at right around the same time. The startup I was working for actually survived the bust and went onto be pretty successful. I ended up going to Hampshire College, which is an experimental liberal arts school. They don’t have grades and everyone designs their own major, which was right up my alley.
How did Bonusly come about?
Bonusly was founded in 2012. I had gone back to school in 2001, graduated in 2004, and did a variety of things. At the time I was in New York City working as a software engineer. An old colleague of mine back from the dot com boom days moved to the same neighborhood I lived in. We were hanging out and he was musing about an idea he had about being frustrated with the current ways that employers very often recognize employees. It’s typically done in a top down fashion or with years of service awards. He felt like there was a tremendous amount of wisdom and knowledge locked up in teams in terms of knowing who’s doing what, who’s bringing what strengths and so forth. We talked about wanting to unlock that knowledge and leverage it to better engage and motivate and reward employees. There was nothing out there at the time to do that, so we decided to just build it working nights and weekends as a side project. I didn’t know if it would grow into anything larger than that.
How did you decide which one of you was going to play that pivotal CEO role?
It was borne out of necessity. We knew this role needed to be fulfilled as we grew, and I basically I had more interest in it than John did. John really is passionate about product and technology and wanted to stay focused on that. I am really passionate about learning new things and taking on new challenges, and taking on this first time CEO role was certainly a way to do that.
How critical do you think it is to truly be invested in the software solution that your company is offering?
I think it’s critical. And so we, of course, are huge believers in recognition and the power that it has to help create a healthy and productive workplace. Everyday there are bonuses flying around the office that are getting announced on our slack channel. I think it’s essential to anyone building software that you’re using that software yourself and using it very passionately. That’s where a lot of the product insights come from, it’s from using it ourselves.
If you could go back to those early days and give yourself a piece of advice, what advice would you want to impart?
In a way, I’m very glad to have not known what was coming, because in a way that fueled the curiosity and the exploration that led to some fortuitous, serendipitous things happening that ended up being really good for the company. I think the one piece of advice would be getting a CEO coach. I found tremendously helpful. Find someone who’s done the journey before, who’s worked with other CEOs, who has a lot more knowledge and can help guide your thinking and provide advice and expertise.
Meet Justin Gray
Justin is a serial entrepreneur and the CEO and founder of LeadMD, the world’s largest revenue operations agency having implemented over half of the Marketo user base. Justin has made a career of launching successful companies and scaling them, with successful exits of over 200MM+ in the last decade. Justin’s latest endeavor launched in 2016 when he co-founded Six Bricks an online learning startup designed to combat employee and customer churn through experience-based education. Over the past 10 years, Justin has emerged as a strong voice for entrepreneurship, marketing and culture. As a recognized speaker, Justin has been published over 350 times in industry publications and holds his own column, Tribal Knowledge in Inc., while writing for Entrepreneur, Tech Crunch and others. Justin and his wife Jennifer met over marketing and three years later welcomed their son, Grayson, into the world in April of 2017.