How to make it as a serial entrepreneur

The Sustainable MBA

How to make it as a serial entrepreneur

Video still of the Propsboard tutorial.
Video still of the Propsboard tutorial.

The following Q&A is an edited excerpt from the Bard MBA’s Nov. 18 Sustainable Business Fridays podcast, which brings Bard MBA in Sustainability students together with leaders in business, sustainability and social entrepreneurship.

Adam Kearney, Bard alumnus and founder and CEO of the peer recognition startup Propsboard, is "really, really comfortable with the unknown." Kearney founded the startup, which uses office TVs to amplify companies’ superstars, with no prior experience in the HR space.

Prior to Props, Kearney was CEO of Connectome (now acquired), a music intelligence company that specialized in search, discovery and recommendations. He is also the co-founder of Philly Startup Leaders, a flagship program featuring a fully integrated startup bootcamp and accelerator that helps up-and-coming entrepreneurs with strategy, vision and execution.

Bard MBA in Sustainability student Martin Freeman sat down with Kearney to dive into his successes and failures, and to get advice on becoming a serial entrepreneur.

Adam Kearney of Propsboard.

Martin Freeman: How does one become a serial entrepreneur?

Adam Kearney: For me, there’s the personal side, which is that I just really love building things, solving puzzles and actual problems and trying to help people. Even before this I was a woodworker, so I loved getting my hands dirty and building things.

You also need to be relentless about everything you’re doing. When you’re running into problems or failures, you just need to keep going. You also need to be really, really comfortable with the unknown. This would be where most people pause at the dividing line. If you’re not comfortable with things that you don’t know, or whatever’s around the bend, being an entrepreneur is probably not for you.

If you’re curious what’s behind that next wall, even though it might knock you out, you’re probably well suited to be an entrepreneur. The last thing is just willingness to fail a lot. I didn’t know I had dyslexia until I was 21, so I was never the smartest kid in the classroom. I don’t care about screwing up and learning from that quickly and publicly, which I’ve done over and over again.

There’s a tactical side to becoming a serial entrepreneur. The best tactical way to get into anything is to figure out a way of building a network that will become reusable. Always give before taking. I volunteered at the first boot camp at Philly Startup Leaders. Every mentor who was a part of it was a volunteer; we thought, "Let’s give to the community and then something might come back."

A lot of the companies in Philly benefitted from that process. It worked well for me, because those CEOs were happy that they were getting good employees. From that I was able to build relationships in Philly that now extend into New York and Silicon Valley. The angle is to work harder, give away your time and money and hope it comes back. 

Freeman: One of the most important things you mentioned was being comfortable with failure. When was the last time you failed at something?

Kearney: A big recent failure was with my current company, Props. We inherited the product, so I inherited its problems. I had also never worked in the HR space. The product was primarily an employee recognition platform. We would broadcast the recognition that occurred in the platform up to everyone’s office TVs, so recognition would be visible inside of an organization. It reminds people to be positive and to show appreciation for their fellow employees and teammates.

The biggest problem was that HR is a checkbox industry. They think, "We gave balloons to somebody for doing a good job this year — check." It’s not an industry that’s looking at an ROI of 10 percent more recognition this year over last year for being innovative. It’s very difficult to sell into these organizations because they aren’t looking for new products, since they are using the same product from the past to check their boxes.

We tried so many traction angles to get into these companies. When we did, we completely swept the company; our engagement was insane. We thought we just had to figure out traction. But we spent way too much time thinking about that, and in the end money was getting tight, and I realized I had to figure this out.

We learned that the TVs are important to the engagement, so I made the TVs our product. Then I went to our competitors’ other recognition services and said, "I know that 60 to 90 days in, your engagement drops and people forget to recognize people. We’ll integrate your product into our service and broadcast it to their office TVs, so you’ll get better engagement and a high deployment strategy." We flipped our distribution problem upside down.

I don’t have to do much selling, because the organizations themselves are contacting their current customers about our product. We have very little competition because we’re working with our competitors, and we’re the only company doing this strategy.

It probably took us six months to see that our problem was even a problem. You have to be critical with yourself, about what things are working or not and why, and talk to people and learn as much as you can as fast as possible. Then implement a change, rather than giving up, because it’s easy to just give up when you have to radically change your entire process and product. 

Freeman: What advice do you have about finding and selecting co-founders?

Kearney: Finding a co-founder is important but incredibly difficult. Most co-founders are found via networking and hustling. Try to build things, join a hackathon, make sure to get to know people you’re working with. You never know when things are going to come back around.

My Connectome co-founder was a friend of a friend, but it took me about eight months of courting him. I was the hated guy in the tech world: the guy who had an idea, couldn’t build it himself, had no money and didn’t know anyone who was willing to jump in on the project with him.

So I had to separate myself from pretty much an absolute cliché. I did little things to prove that I was serious and we started working more together. I probably spent just as much, if not more, time with him than with my now-wife.

I always ask of potential co-founders to tell me about the shittiest job they’ve ever had. More important than their answer is where they come from, how they have pushed themselves and their outlook.

Freeman: Are there any courses you would recommend to someone looking to get into the tech world?

Kearney: I would encourage everybody to learn how to code. Self-driving cars will be here in three to five years. Just being able to understand how those systems work is going to become part of a political conversation. To be a good citizen you should understand coding, because it’s entwined with our life. From a career standpoint, you should learn how to code to be able to work with developers.

I would recommend that people learn Ruby on Rails. Websites like the New York Times, Twitter originally and Hulu are all Ruby on Rails. For example, a 19-year-old kid came to my community course in Philly. He couldn’t afford to go to college and he was just so ambitious. He finished the One Month Ruby on Rails course in a day or two, and then devoured anything I gave him. By the third week, he was integrating payment services into a fake website that he built.

He quickly learned basic skill sets and was able to utilize them to control his situation. That morning, he started a company making shelf-stable organic beef bone broth and recycling the used bones by selling them at low cost to dog bone companies. They did $1 million in revenue last year.