Raphael Akinsipe is a serial entrepreneur, and former Chief Growth Officer of the health-tech startup Casetabs, which was sold in 2020 to Bain Capital. In addition, he is a former Google product manager and has served as a growth strategy consultant for brands such as Marvel, Southwest Airlines, and Brinks. Currently, Raphael serves as the Senior Vice President of Marketing & Strategy at HST Pathways and leads the Akinsipe Family Scholarship Foundation.
I’m the son of Nigerian immigrants, and I grew up in Houston, Texas. I had a variety of interests growing up, and I worked on tons of different projects as a kid.
I went to Texas Tech University to get a degree in Civil Engineering. While I was in college, I got into tech and entrepreneurship. I started my first company as a freshman selling wristbands - if you remember those Livestrong wristbands, we were selling wristbands similar to those. We took the profits from that company to start another company called Glow Station. Here we developed a proprietary line of shirts that would light up to the sound of your voice. From there we developed light-up sportswear for a number of colleges and universities. We wanted to scale that, so we eventually raised money from investors in our university network, and that was my first experience with venture capital. With that money, we scaled the business and continued to work on it in college, but we eventually hit an inflection point where we had to decide if we wanted to raise more money or try to move on, and we decided to sell our patents and move on to the next thing.
From there, I worked on a series of other things like web apps, and I worked with a number of startups building apps for them. I didn’t think about it at the time, but this was my first foray into product management. I did that until I got out of college, and then I went into a consulting role with Sabre helping clients grow their businesses faster. From there, I did product management at a couple of different companies, and I eventually got into product management at Google.
Throughout all of this, I kept working on different side projects, and that’s what led me to Casetabs. I met the CFO of Casetabs playing basketball. He threw me an alley-oop in a game, and we got together afterward to just talk about what we were working on. We got lunch later that week and he told me about what he was doing with Casetabs. I soon started consulting with them on the side while working my day job at Google. They eventually asked me to come on full-time, and I was hesitant because I had just started at Google, but I eventually decided to leave Google to work with them.
Casetabs is a software company that makes scheduling solutions for surgeons, surgery centers, and hospitals. It was a new challenge, but it was awesome to be in it full-time. I tell people that was the first time that my side hustle became my main hustle.
Towards the end of 2020, Bain Capital approached us saying that they were interested in merging us with another health-tech company - HST Pathways. It was exciting to get to an exit, and I decided to stay on at HST Pathways to drive growth.
My parents are immigrants, and we didn’t have a ton growing up. That’s always been a motivator for me, and from a young age that instilled a work ethic in me. I think it’s lost on people that immigrants cross an ocean to start a new life somewhere. Hence, there is a great deal of ambition and perseverance that has been in me that drives me every day.
Another part of it is that I’ve had the opportunity to see a lot of different things. I launched a new website (RaphaelAkinsipe.com) around career acceleration. The first part of that is what I call “finding your superpower.” By that, I mean go out and try lots of different things. That was hugely impactful for me because it opened me up to things that I wouldn’t have otherwise been aware of.
Lastly, I’ve just been really blessed in my life, and I think God has been a big factor in how things have played out for me.
A lot of people make the assumption that the only way to build a business is to be all-in from the beginning. They think that you have to quit your job, put in all of your savings, etc. With a lot of my first companies, I was going to school full-time. With all of my side hustles, I was working a day job while building it. You can do the nights and weekends and make your business a reality before going all in.
There are two tracks that I recommend to people.
The first is to build something yourself. When I was interviewing at Google, it was good that I had product management experience, but the thing they were most interested in was that I had built something myself. So my advice is to just go build something. It doesn’t have to be anything amazing or fancy; you could build a website. Just start making something that people care about, and set goals for yourself.
The second track is to be a product owner or project manager at other companies or in other roles. That gives you experience leading something in development, and it’s a good transition into being a product manager.
Treat the early part of your career as a series of internships. Focus on gaining several high-value experiences where you can learn and absorb the skills around you. People are overly concerned with getting tenure. Diverse skills and experience will take you much further and more quickly than several years of one thing.
There’s a saying that goes: if you put value into the world, the world will put value into you. Everyone is focused on trying to make the next cool thing or the next version of something that’s already out. I think that if you’re focused on putting value into the world and you’re solving real problems, you’ll have a very successful startup.
Look around the world and your life to see what problems people are having. By looking at those problems, and focusing on solutions that make people’s lives easier the world will put value into you. Put the problem first. Too many people just jump into building a feature. Build a real application that solves a real problem.
Something I tell younger people like students and young entrepreneurs is to leverage your universities as much as possible. Every school is trying to find its next Mark Zuckerberg. At Texas Tech, the president of the university was super invested in startups and entrepreneurship. There are lots of successful alumni at universities who want to connect with students doing cool things. If your school has an alumni network, reach out to them and ask for access to people that are willing to work with student entrepreneurs, and you’ll be surprised at how many people get back to you. I recommend this even more for people after they’ve graduated because schools always want to hear about alumni trying to do new things.
I also recommend listening to the This Week in Startups podcast by Jason Calcanis. That’s been super formative for me because Jason knows everyone. It taught me a lot about startups and entrepreneurship. There’s a quote that always stuck with me; it’s something to the effect of: consumers are people with more time than money, investors are people with more money than time, and entrepreneurs are somewhere in between.
One example of a hack that I used was for a startup I was working on called Resumakers.com. It was an AI-tool like Siri that would make your resume. We wanted to find ways to market the app without spending money. So what we did was go on Google and register a local office with our apartment as the address, and then when people searched “resumes” that were within our region, we showed up on the organic search results. This was really easy to scale because we could use a co-working space as our address in different cities, so we had Resumakers in San Diego, New York, and a lot of other cities. That was a really easy way for us to grow our business and establish ourselves in other markets because we would show up in the organic google search results. Finding hacks like this is an easy way to scale your business.
it’s easy to get so caught up in the grind that you ignore how far you’ve come. When I asked Raphael why he decided to close his Glow Station despite the success and growth he was having, he said that there were a couple reasons (they weren’t profitable, unit economics weren’t great) but the biggest reason was because he wanted to go do other things. We need to understand that just because we’re good at something doesn’t mean we have to keep doing that forever. In every phase of your career. keep your finish line in mind and when you get there, don’t be afraid to move on to the next big thing.
Without even thinking about it, Raphael’s early career experiences really set him up to be in a position to join Casetabs and lead growth there. He got some growth marketing and fundraising experience during his time working on his startups, and consulting for various brands. He got product management experience during his days building applications for other startups. He learned about leading teams during his time at Google.
Raphael said that he treated every part of his early career as a series of internships. That is such great advice. Everything that you do at work right now contributes to where you want to go down the road. Look for opportunities - both big and small - to get into different fields at work. Always be on the hunt for other projects and gigs to grow your expertise; you never know when it will come in handy to be able to speak to those experiences.
Raphael said that his biggest piece of advice to aspiring founders is not to go all-in too early. It seems like every success story we hear is one that involves founders quitting their day jobs as soon as they have an idea and bootstrapping it for months before they find success. These stories are popular because they’re sexy. Working your day job and building your company nights and weekends isn’t sexy, but it’s practical.
Take your time and give yourself grace. When it’s time to go full-time on your idea (either because you’re getting traction, you no longer have time to do double-duty, or for other reasons), you’ll know.