Endeavor Fellow Flaviu Simihaian – From Tennis to Tech, A Serial Entrepreneur’s Journey
Endeavor Romania Fellows are role models for our young entrepreneurs and are critical to the development of our entrepreneurial ecosystem. They are well rounded entrepreneurs, business professionals or thought leaders, whose experience and expertise are relevant to the needs of early stage startup founders. The Fellows personify our values — they dream big, are generous with their time and connections, and contribute to our network.
Flaviu Simihaian is a serial entrepreneur and technology innovator with a background in tennis and economics. He moved to the US at 14 and transitioned from building websites in college to co-founding two successful healthcare technology startups.
Flaviu is also strongly passionate about leveraging technology to bridge the gap between generations of people, particularly in healthcare.
Tell us about your journey from tennis to tech to becoming a serial entrepreneur.
Tennis is what I did every day for four hours from when I was five until I was 21. I do think they’re both related, because it’s an individual sport, and it’s very entrepreneurial in a way. It definitely prepared me for a path in entrepreneurship.
Plus, my dad was an entrepreneur in Romania, which, in the ‘90s after the communist regime, it was a difficult profession to have. I would watch him build his business amidst moving legislation and a country finding itself. That experience, along with maybe some predisposition, pushed me towards entrepreneurship in tech. I often tell people in the US that there’s just something in the water in Romania when it comes to tech.
While kids in the US were playing American football or in the yard, kids in Romania were in internet cafes trying to hack each other’s computers, at least when I was growing up. I wasn’t that great at tech, but when I came to the US, relative to the standard here in both tennis and tech, I found myself in a higher percentile than before.
I started building websites and I did this until college. After college, when I was trying to find a job in economics, it was 2008, which was a historically bad time to find a job in that field.
That’s when I started considering tech, even though I didn’t have much professional experience. It was kind of nice to have a blank slate. I eventually got a job in tech, met a co-founder, and fell into it one step at a time.
What drew you towards the healthcare industry?
When I was around 12 or 13 in Bucharest, in Piata Romana at the subway station, I remember seeing an old woman begging. She reminded me of my grandmother, whom I was very close to. The woman seemed very old and weak, and it made me cry. I gave her all the money I had, which wasn’t much, and that moment left a lasting impression on me. I felt that the younger generation should take care of the older generation because they often can’t take care of themselves.
This feeling became more pronounced as I thought about technology. Even today, the older generation—particularly those 80 and above—are often disconnected from the world of technology. I felt a responsibility to bridge that gap. Growing up with my grandmother in Romania reinforced this mindset.
Health is a very specific vertical to be in. Are there any key factors that contribute to the success of a startup in this industry?
Health is definitely more challenging. A lot of people talk about healthcare and education, saying they’re broken and need fixing, but in every country, it seems like healthcare and education are considered flawed and in need of improvement. These are huge markets—in the US, healthcare is a $3 trillion industry, and education is another $1.5 trillion, making up a significant portion of the economy.
Innovation in healthcare is hard because it’s often government-driven, with huge incumbent players who aren’t easily displaced. In software, you had companies like AOL and Netscape, which became obsolete quickly because technology moves fast. But in healthcare, innovation isn’t encouraged, and the most innovative company doesn’t always win.
The most important factor in succeeding in healthcare, which took me a long time to understand, is that sales are 10 times more important than the product. My co-founder and I were both technically inclined, so we built the product, but we struggled with sales. Sales in healthcare can take years, and investors often expect revenue before they invest, so you can’t wait years to start generating sales.
We had to teach ourselves sales, and I was fortunate to have some mentors who helped us along the way. Figuring out how to generate any amount of revenue is crucial. In our case, we had a small business sales process—boots on the ground, driving to pharmacies, attending conferences, and doing phone and webinar sales. That’s 10 times more important than having a great product with no sales.
People often look at exceptions like Instagram, which sold for a billion dollars with no sales, but those are outliers. The reality is that you need sales to survive. Without sales, a good product alone won’t work.
Was there any decisive moment in your entrepreneurial journey that had a huge impact on your career path?
There have been many moments. One that stands out is when the Democratic National Convention was held in Charlotte, North Carolina, where I lived at the time. They were looking for startups to showcase, and we were struggling to survive. I spent all day chasing investors like Arianna Huffington and Andrew Yang, hoping to make connections. None of those panned out, but I met a lot of people in a short time, which maximized those opportunities.
One encounter that seemed minor at the time was with a startup accelerator. They mentioned they were looking for startups and offered us $10,000 or $20,000 if we moved to New York. I told my co-founder about it, and we decided to record a quick one-minute video submission at 3 AM after a long night of work.
We ended up getting accepted into the accelerator, which gave us some money and moved us to New York. That changed our trajectory, allowing us to raise more money and become better entrepreneurs. It became more real when someone believed in us and gave us advice. It was a random meeting, but it had a significant impact.
The takeaway is to put yourself out there. Especially now, when you can work from home, it’s important to expose yourself to opportunities in-person.
How do you stay motivated throughout this entire process?
That’s where having a co-founder is really important. A lot of people think they don’t need a co-founder, but when things get tough, having someone to lean on is invaluable. It might sound cliché, but having someone to call when you’re down is worth 50% of your company, because otherwise, you might shut down due to lack of motivation.
There are other criteria for choosing a co-founder, but motivation is the most crucial. Another key to staying motivated is having a clear belief in what you’re doing. If you’re just in it for passive income, you’ll give up when it gets tough. Building a company for passive income is one of the hardest ways to achieve that goal. Most people need some kind of human connection or purpose to stay motivated. In our case, we were motivated by the idea of helping seniors. You need to believe that what you’re doing is impacting other humans, and that’s how I stay motivated.
What piece of advice would you give to entrepreneurs in Romania or other developing markets who are looking to scale their businesses globally?
Choosing your market carefully. I see entrepreneurs in Romania who get a little traction then try to expand to the US. This is something that needs to be decided early on. I would like to see entrepreneurs starting with a different market in mind, because every state in the CEE is too small to single handedly power a high impact company.
Pick your end market from the beginning and start there directly. Showing some traction in a larger market is more important than lots of traction in a small market , and skipping the local market phase gives you a strategic advantage over your competitors.