Sam Tarantino: “We Started Grooveshark At 19 We Had Zero Experience So Everything Was Learning On The Fly”

Sam Tarantino is currently the founder of, a personal radio to play and listen to new music broadcasted by real people in real time. Sam’s journey began at the age of 19, when he founded Grooveshark, the disruptive music streaming service that built its following up to 35 million users, and later went on to lay off 140 employees. He is a passionate musician who has found a way to blend it with his entrepreneurial endeavors. I took the time to chat with Sam about how his journey has been touched by success and about the personal struggles that have helped him into the person he is today.


Q: What are some challenges you faced when developing your venture?

I think the more appropriate question is what wasn’t a challenge? Because we started Grooveshark at 19 we had zero experience so everything was learning on the fly and that involved making mistake after mistake. I call it the “hall of mirrors” approach to learning where you keep bumping into a wall and that let’s you know where to turn vs where to go straight. Raising money is a challenge no matter how old or experienced you are. We were raising it in a music industry that was fraught with failed startups so VC’s in general were reticent to invest in our space. Then on top of that we were raising money in the middle of the 2008 financial crises which made it extremely difficult since there was so much fear around that time. Then on top of that we got sued by the major record labels which made it impossible to have any sort of growth or exit despite having gotten as far as 35M users and over $12M/yr in revenue. Ultimately those challenges paled in comparison to having to shut the company down after our lawsuit settled and even more so compared to losing my co-founder and best friend Josh after 9 years of overcoming all those challenges.

Q: Was there any point when you thought it was over? That you were going to fail?

I’d say quarterly if not monthly. So many people kept writing that we were dead within a month that after 3 or 4 years we just stopped listening and focused on building the best product we could. The hardest part was definitely when it actually was over after 9 years and it did fail. I was so afraid of what that process was going to be especially after having all our dreams come true like they were. What I learned though was that you survive it and you keep going. Humans are surprisingly resilient and never was that clearer to me than when we lost it all.


Q: As an entrepreneur how important has flexibility been in developing your venture?

Immensely important. Entrepreneurship is a weird mix of being flexible while being stubborn at the same time. My favorite author Jim Collins calls the process “bullets and cannonballs”. When you’re starting and idea or product you shoot low risk, low cost bullets against the wall and that is where the flexibility comes in. Even the original Grooveshark idea didn’t end up being what eventually resonated with consumers. We started as a p2p Buy, Sell, Trade marketplace and when it became clear that people were just previewing the songs and then the iPhone came out we realized that people would just stream music without the need to download. Once the site started blowing up (about 250–500k users per month growth) that’s when you shoot the “

Cannonball” or the high risk, high cost bets since the product is now proven. That is where the stubbornness comes in. There are so many things that can derail a successful product that it takes discipline and dedication to stick with the vision and see it through to completion. The hard part and the balance is in recognizing when being stubborn is holding you back vs helping. It is a hard thing to recognize because they are disguised as each other.


Q: What was was your spark, where did it come from?

It wasn’t so much a spark as much as a lifestyle decision. After I met my co-founder Josh we decided that we should just take a stab at building a business and product to solve some music industry problems. The spark came from when we saw from the beta that people were not downloading songs but preview streaming them and by huge numbers so it was then we decided to pivot to focus purely on streaming only.

4. What are your non-work habits that help you with your work-life balance?

The outdoors I’d say powers a majority of my creativity. I like to hike, ski, & climb and I have a routine that from 7am-11am I focus on these activities which makes me feel super powerful and energetic for the rest of the day. Some of my best breakthroughs have been on the slopes or trails or crags since nature is an incredible analogy for a lot things we see in business.

5. What is your best tip for entrepreneurs?

Don’t be so attached to outcomes. I spent so much effort and energy willing Grooveshark to succeed and ultimately there was nothing I could do to stop it’s eventually shut down. Most of the moments I remember are the ones with people I loved to work with and projects that we had a blast working on. I liken it to river rafting/kayaking. You can move within the river but you’re stuck following its current and flow. Go with the current and put in the effort to move within it. Mostly though enjoy being on the river because it is a beautiful ride even though the rapids.