America at work
Be a Mediocre Entrepreneur in a Great Market
Free Enterprise Staff | February 29, 2016

The vast majority of businesses fail. That fact makes Justin Smithline, who has started three successful companies—including one that he sold to SoundCloud—all the more impressive.

Smithline has taken an unconventional road from the start of his career to where he is today. “I definitely did not map out my career path,” Smithline tells Free Enterprise. “I think if you try to over-script your life, you close yourself off from opportunities.” After a stint at Fidelity Investments, Smithline transitioned into the startup ecosystem, working at two firms; one thrived while the other failed.

From there, he founded Linguaflex, a medical device for the treatment of sleep apnea that is currently in Phase III clinical trials; the music management and recommendation platform Instinctiv, which he sold to SoundCloud; and FunnelFire, a real-time data platform that enables sales and account people to automatically research, track, and engage with their enterprise customers.

What makes Smithline successful, and what has he learned over the course of his still-young career? We posed those and other questions to the serious entrepreneur.

Talk briefly about your background and what led you to work for yourself instead of working for other people.

I’d always been pretty entrepreneurial from an early age, from having a t-shirt business in high school to selling jewelry in college. My dad was a business owner, and his father was an artist during the Great Depression, so I guess you could say that independent streak was in my blood. That being said, I also appreciate working for great people and have valued those opportunities over the years.

What are some of the lessons you’ve learned?

First, who you are working with is more important than what you’re working on.

That being said, being in the right market at the right time plays a huge role in how successful you’re going to be. I’d rather be a mediocre entrepreneur in a great market at the right time, than a brilliant entrepreneur in a small or contracting market. It’s better to have wind at your back than wind in your face, and entrepreneurs should try to figure out which way the wind is blowing before jumping in.

Lastly, don’t waste your time working on “nice to have” ideas. If it’s not a “must have” for somebody, don’t bother.

What advice do you have for choosing a co-founder? 

Choose someone who is trustworthy, has a different set of skills and personality traits, and can provide a different perspective. I’d also really think through if you need a co-founder if the type of business you want to start doesn’t necessarily warrant it. Whatever you do, if you do take on one or more co-founders, make sure you have vesting schedules in place for all co-founders, so people can’t quit one month after you started the company and walk away with large chunks of equity.

What did you learn through selling Instinctiv to SoundCloud?

It’s very important to build relationships in the industry you’re working in, as you never know when the opportunities to partner may arise.

What’s the biggest misconception about being an entrepreneur? 

That it’s a glamorous existence. It’s very difficult and often lonely work, which is why most businesses fail.  You have to work incredibly hard every single day to create success.

Looking back on your career, what do you wish you had known in the past that you know now? t:

Great opportunities in business don’t present themselves very often. It’s often a confluence of a variety of factors, including luck and timing. If you get presented with a great opportunity, take it.