CEO Shehzad Daredia’s “Incremental Path To Entrepreneurship”

Shehzad Daredia at Le Web (Photo courtesy Kmeron)

Shehzad Daredia is CEO of, a music tech startup with a music player that allows one to share music while giving the listener the ability to listen on the music streaming service of their choice. Daredia and cofounder Stefan Gomez (CTO) successfully built on a journey that has taken them through Y Combinator and on to receive $2 million in funding and media partnerships with such companies as Billboard and Twitter.

I recently spoke with Daredia about his learning process from student days at the University of Pennsylvania, where he began his education in entrepreneurship in earnest, to the present, where he has experienced investors to whom he can turn for advice. It’s the first of a series of interviews I’m conducting focused on how startup CEOs learn to do what they do in an often chaotic environment absent the long grooming period of established corporate CEOs. To Date

When launched out of beta in late 2013 their music player already showed great promise with the ability to stream songs from YouTube, SoundCloud, Rdio and Spotify. went on to receive $2 million in funding by 2014. They also grew rapidly gaining not only new music listeners but also building relationships with a wide range of musicians, including verified artist pages from artists like Tiësto, Lil Wayne, Snoop Dogg, and Paul McCartney, and with additional music services such as Pandora, Xbox Music, Rhapsody, and Napster.

2015 has already been a great year for with the launch of a mobile app at Le Web, a partnership with Billboard and Twitter to use their player on charts and whitelisted status on Facebook:

“Starting off we did a partnership with Billboard and Twitter where we power music playback on a few different Billboard charts on the web…realtime trending charts where Twitter powers the data on which songs are moving the fastest on Twitter. Billboard hosts the charts and then we power the music playback.”

“Billboard was previously going to go with Spotify but then they ended up replacing Spotify with Bop because it’s a much better user experience. It incorporates Spotify but also plays through every other music service as well…”

“We followed that up with the partnership with Facebook where we now have whitelisted inline playback access on the newsfeed and artist pages. So when someone shares a Bop link on Facebook it now renders our HTML5 player for inline playback.”

“Which is really cool because when the countless number of artists that are sharing Bop links to singles or playlists every week, when they do that now their fans can listen inline without having to leave the newsfeed.”

Though plenty of challenges lie ahead, this stage of development seems a good one for Daredia to look back and reflect on how he learned to do what he does as CEO.

An Incremental Path to Entrepreneurship

To get to this point, Daredia took what he describes as an “incremental path to entrepreneurship.” It began at the University of Pennsylvania where he studied both engineering and business. In addition, he immersed himself in entrepreneurship opportunities that helped him “get on a path towards jumping into tech startups in general.”

Such opportunities included “business plan competitions and in-house student VC groups.” He “also dabbled in a couple of entrepreneurial projects while in school, such as a precursor to Slingbox, but those projects didn’t really go anywhere commercially.”

This rich educational environment, that includes the Weiss Tech House, allowed Daredia to begin a journey that was not about becoming a CEO but about becoming a founder:

“My desire going back to college has been entrepreneurship specifically because I found that to be a vehicle for being able to enact change in a sustainable scalable way although obviously with a very high degree of risk. But if it pays off then it pays off in spades and you’re able to implement great change that can impact a lot of people.”

One might think such a desire would lead to CEO dreams but Daredia actually is somewhat repelled by the “halo effect that we place on not just leadership but also titles that come with it.”

More than once he shared his mixed feelings about titles and labels like CEO and entrepreneur, due to the rising tide of hype associated with such terms, and revealed that he is prepared to give up the role of CEO if that’s what or any future company he helms requires.

Daredia confirmed that, for him, the bigger picture is about building a successful company that can have significant impact.

From Going To School To Having A Job

After graduating from U Penn in 2006, Daredia continued his “incremental path” in the workplace with an awareness of this bigger picture:

“I wanted to progressively add more and more skills to my skillset and arm myself with all the things that I would need to best prepare myself for when I was ready to take that plunge.”

“I started my career in VC. Then went and joined a midstage startup called which had at the time the body of an early stage startup, early to mid, and was able to get some responsibility and experience that way.”

“[I] then joined another startup called BillShrink [now Truaxis] which was earlier stage and joined as a different role [becoming director of product]. So I started out getting some marketing chops and then I got some product chops and rounded out my skillset as best as I could before this particular opportunity struck me and my coworker at the time, [Stefan Gomez], and we decided to take the plunge.”

“At that time we thought we had…a good foundation of experience in the Valley that we were able to apply towards this challenge.”

Learning About The Music Industry

Though neither Daredia nor Gomez had worked in music, they did have experience related to the architecture of

“Neither my cofounder nor I had a background in music. We did have a background in consumer tech and startups and search, in particular. My cofounder and I had 11 different search engine verticals of experience between the two of us and music is effectively our 12th quote unquote search engine…”

“The user experience is a little bit different. It’s not a search oriented experience. But the architecture of it, the underpinnings of it are similar to search.”

So Daredia set out to learn more about the music industry:

“One of the things that I did was study a lot about what came before us and how the industry works. And then went and sought out experts in that industry to be able to get feedback from them and bounce our approach off them and create what I called a win-win-win value proposition for all the key stakeholders.”

“We ultimately came to the idea that Bop could be a win-win-win for users, artists and labels, music services and then even web publishers.”

“Users get this comprehensive tier of music that is easy to share with anyone. Music services get a performance based marketing channel for acquiring new users. Artists and labels win because we promote the healthy paid legal adoption of music in a way that promotes monetization rather than piracy.”

“And then even web publishers win because they get an easy way to add music playback, legal music playback, for their audience in a way that doesn’t erect barriers in front of them.”

“So we created this multipronged value proposition.”

What Would Dalton Caldwell Think?

Daredia and Gomez talked with a number of people in music and tech as they educated themselves. One in particular stuck out in our discussion:

“We also talked with folks like Dalton Caldwell. He’s a founder of iMeem which is a big poster child of why not to start a music startup. It rapidly ascended and rapidly crashed and burned. And Dalton subsequently gives this very famous talk at startup school every year called “so you’re thinking of starting a music startup?

“He tells you all of the reasons why you shouldn’t. And so I saw that and thought man, this guy, really smart guy, great experience, notoriously bearish on doing a music startup, if I can reach him and convince him that we have gone about this in a thoughtful way that avoids all the pitfalls of music startups, then I think we’re on to something here and we will continue to pursue it.”

“So that’s what we did. Chased him down, tried to get his attention. Obviously he’s a very busy guy. Finally got through to him. Pitched him and he not only liked our approach but he also is a part-time YC partner and ended up being one of the guys that facilitated us getting into YC.”

“And he’s a mentor for us till this day.”

Attending Y Combinator

Having developed a prototype and received “validation” from “smart folks in the industry,” the two managed to gain entry to the renowned Y Combinator accelerator in the summer of 2013. Daredia clarifies that he didn’t see YC as a place to learn about being a CEO:

“While you’re in YC the focus is…less so on management advice and more so on just getting off the ground.”

But the experience and what he learned in the process seems a crucial component of a startup CEO’s education:

“YC is great for a number of reasons.”

“One thing that it does is that it has seen so many different early stage companies that it creates its framework for all the things that you need to think about when you’re getting started so that you don’t have to reinvent the wheel every time. It’s very very helpful in avoiding a lot of the mistakes that first time founders make when they start a company.”

“So whether it be things like incorporating properly, getting your affairs in order from an administrative standpoint to also knowing what to focus on in the early days and setting milestones and having a pressure cooker environment to reach those milestones quickly so that you can build momentum and use it for raising money…”

“Probably the most valuable aspect of it was that pressure cooker atmosphere. It’s a short period of time where it’s very, very highly leveraged and we’re just heads down cranking away but also being singularly focused on really just two things, which is building product, talking to users.”

“We got a lot of value out of that, from the mentorship, from the peer community, the community aspect, and then of course the halo affect and the fact that they bring in a bunch of investors on demo day, kind of a captive audience for you.”

But after graduation YC does organize events more directly relevant to the education of a startup CEO:

“They do a really good job of keeping the alumni community engaged on a periodic basis with more educational events that include panels where other alumni who are at more advanced stages or later stages of their companies will come in and talk about a different set of challenges than the ones that companies that are actually going through the 3 month Y Combinator program at that time were focusing on.”

Said challenges include “building a team and scaling.”

Turning To Investors For Insight

Occasional events are not enough to cover all the issues with which a startup CEO grapples. Daredia says he now has investors with impressive operating experience who help him figure things out:

“I turn to some of the investors in my company that are kind of handpicked or chosen to back us based on their experiences. I really value our relationships with our individual investors, our angel investors, in addition to, of course, our institutional investors.”

“But the one thing the institutional investors don’t have is very recent, up to date operational experience. For example, Bop has, as investors, two cofounders and one VP of biz dev from the last company I worked at…a company called Truaxis.”

“So the CEO and the other cofounder are investors in Bop and then also…at, my boss in that job, the founding VP of marketing, is also an investor in Bop.”

“In addition, not only do we have people who are former bosses, former founders and execs, at the company that me and my cofounder used to work for but also a few other individual investors as well.”

“We have the former head of digital from EMI as an investor and we also have a guy who has a very, very deep level of experience in the media and publishing world as an investor as well. So he provides a lot of great relationships and contacts into the web publishers’ side of the business.”

“These guys have been fighting the good fight for a long time and continue to do so and have had successful exits and have been through the whole cycle a number of times.”

“So, for example, one of our investors has built and sold two companies already. One of them has filed for an IPO and the other company of his was sold to Mastercard. So he’s already 2 for 2 on his ventures, seen this multiple times. And the other one, the guy that was founding VP of marketing, is now a second time CEO at another startup.”

“These guys are incredibly helpful for us. I reach out to them on a pretty regular basis with questions on all sorts of tactical and strategic things.”

At The End Of The Day

As Shehzad Daredia noted, he “highly recommends” taking such an incremental path while acknowledging that “it’s not for everyone.” He also pointed out that he still made plenty of mistakes and had much to learn after launching with Stefan Gomez.

Though he hasn’t had kids, Daredia believes that experience may be an excellent analogy and sums up a key point about learning to run a startup:

“From what I hear you can’t truly be completely ready for having kids. It kind of happens and you end up learning on the go and trying to talk to your own parents and in-laws and read books and try to figure out how best to be able to handle this new situation that’s thrust upon you.”

“But at the end of the day, it’s kind of a trial by fire, right?”

Learning To Be A Startup CEO: CEO Shehzad Daredia’s “Incremental Path To Entrepreneurship”
Nico Perez On Where Mixcloud’s Founders Turn When They Have Startup Questions

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Clyde Smith is a freelance writer and web publisher with a doctorate in Cultural Studies from The Ohio State University. He began building websites and creating content in 2000 eventually launching ProHipHop, the first hip hop trade blog, in 2005. From 2011 to 2014 Clyde wrote about music tech and the DIY music biz at Hypebot. He is currently planning a relaunch of DanceLand.

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Clyde F. Smith, founder of and, can be found at or at

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Clyde F. Smith

Clyde F. Smith

Clyde F. Smith, founder of and, can be found at or at

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