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Tech insights: How I quit Google and lost $100k - Interview with Jason Grishkoff
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How I quit Google and lost $100k - Interview with Jason Grishkoff

07 March 2019, by Anne Gonschorek

With his brainchild Indie Shuffle, Jason Grishkoff has created a music blog that, eight years after its launch, is still one of the most popular music sites on the web. It has however also cost him $100 000 and many sleepless nights. OfferZen met with the Capetonian to hear about how he bootstrapped Indie Shuffle and kept it (and himself) alive after crashing financially.


Let’s start by introducing you. Tell me about your background before Indie Shuffle?

My name’s Jason. I’m originally from South Africa. I went to high school in the States and then to University in San Diego where I studied history and political science.

I wanted to get really rich so I decided I would become a strategy consultant. I got hired by a firm in Washington DC, doing something called “executive compensation consulting”. Needless to say, I didn’t really enjoy it and was on the verge of being fired after two and a half years.

I had created a music blog on the side and they thought it was distracting me from where my real focus should be. But! As I was going through the final performance review, I got a phone call from Google asking if I wanted to interview with them.

I think the reason they ended up hiring me is the very same music blog my previous job hated. A bunch of the folks I was interviewing with were about to go to a music festival called Coachella. That’s all they were talking and thinking about. When I said, “I run an Indie music blog and we write about those people,” there was suddenly this instant connection. It just clicked.

Indie Shuffle was two years old and still on the up and up. It hadn’t really gained that much traction - we were probably doing around 100 000 pages a month.

So how did the Indie Shuffle music blog come about? Why did you start it?

It started a couple of years before that when I first moved to Washington DC. It was my first time as a young adult moving to a completely new city with no friends or anything. I was feeling really depressed and lonely. Actually, for the first month I was there, the room I was staying in had no windows. That obviously didn’t help with the depression.


To stay in touch with my friends, I started to email new songs that I was torrenting: “Here, check out this. I found a really cool band called Two Door Cinema Club or Phoenix.” Today these bands are considered stalwarts of Indie rock, but at the time they were still emerging.

This went on for a little while until, eventually, I decided it needed to be a little bit more permanent and that’s when I started a WordPress blog.

Was that basically still just you putting up music that you wanted to share with your friends?

Totally. I put a little MP3 player on there and wrote a bit of a post around the catchphrase: “What’s so good?” where I’d explain why I like it. But then, very early on, I received messages like: “Hey, I really like that I can play the song on your website. But I wish it would play something after that song ends.”


I thought that that was a great idea. No one had done that before. This was before Spotify and SoundCloud existed. There was Pandora Radio but very few people in the online music space had tried to create an online playlist.

So you added that as a feature?

Yeah, I guess that’s when I first started coding really rudimentary stuff. I took a WordPress plugin that shows you other posts in the sidebar and hacked that to pick the songs that should play next. It used tags to determine similarity. Then you would do some sort of Ajax call to try and get the songs that were embedded within those posts. I had to hire someone to do it because at the time I was clueless.

Anyways, now this automated play next function is just assumed. It’s also assumed that you can navigate the realm without the music being disrupted. In 2008-2009 that was a groundbreaking idea. I paid some guy $100 to try and build that for me and he sort of did, but I wasn’t happy with it. I tried to tweak it myself and broke it. Then I had to hire someone for a lot more money, $3 000 type of thing, to go: “Okay let’s do this properly.”

What were some of the first big things you started building?

I guess one of the biggest things that happened from a development side was the release of the iPhone and Android apps. This was about 2012, so music apps were all the rage at that point.

I had a contact at a company that would give me a really good discount for building them. They scoped it out to be about $80 000 for both apps and gave them to me for $20 000. The apps were big hits at the time - Spotify still didn’t exist; SoundCloud didn’t have an app yet. We were one of the cool kids on the block.


We were doing something like 500 app installs a day that would accumulate to somewhere around 750 000 installs now. The daily active users have clearly gone down a lot because of a lack of app maintenance so I am starting to rebuild it myself now. In addition, the market has gone to more reliable services like Apple Music and Spotify. It’s a tough market to compete in as an individual.

Did you get any help or were you doing all the blogging by yourself?

Really early on, when I had written about 100 posts, I came to understand that a) I didn’t have the bandwidth to just keep pumping them out, and b) the more I published, the more traffic I got.

So in 2008/2009, I first started bringing on friends. That ended up backfiring because - well, don’t hire your friends. I realised quickly that I needed a proper team. We tried volunteer writers for a while and the first time I made a decision to pay them money was in about 2011.

Indie Shuffle’s ad revenue had grown to be around $40 000 a year so I was able to take that money. I also brought in a friend of mine who came in part time as the editor in chief.

And what was the arrangement?

For the most part they were doing it for the love of the game - and free access to as many shows as they wanted to. We were investing most of the money that the company earned back into business to support an Editor in Chief, hosting expenses, and the occasional big show (SXSW for 3 years). There wasn’t much extra money for developers but as I said, I spent $20k on apps and was starting to dip into my own funds a bit.

When did that turn into the decision to leave Google?

It was a combination of a lot of different things. Google is the perfect place to work but after a few years that loses its glamour: You just don’t have a life outside of Google. Your friends are all Googlers, your girlfriend is a Googler. That is life and there’s nothing else outside of it. That gets to you after a while.

The second thing is more industry specific. In 2012 and 2013, display advertising was going through this massive explosion in awareness and people were getting ripped off heavily. Within the music niche, Spin Magazine merged with a company called Buzz Media and they became the biggest digital agency for music websites. There were tonnes of money flowing in and as part of their merger they wanted to renegotiate all the contracts with their properties.

Indie Shuffle was one of those. I don’t know how I pulled it off but I negotiated $180 000 a year guaranteed before they sold any ads.

For Indie Shuffle?

Yeah. I said: “If you want 100% control of our ad space, you’re going to have to pay us $180 000 a year.” My expenses were around $40 000. That leaves $140 000.

So I was like: “Maybe, if I take $80 000 of that and put that into a full-time dev team so that I can just really ramp things up, I’m still left with $60 000 for running my own business. That’s enough to live on and maybe travel around and then I’m free of the shackles of corporate life.” So I quit.


How did that post-Google life look like?

When I was finally free, I moved to Europe for eight months and it was fantastic. But the money didn’t come. I mean, I was spending it. I had hired a team of 6 developers in Bangladesh. Then I moved down to Cape Town, rolling out new iPhone/Android apps. I was like: “We’re done with WordPress, it’s holding us back, let’s rebuild everything from scratch in PHP framework!”

Still no money. After a year, I said: “Gosh where’s the money? This is ridiculous.” I was calling them now, I was demanding meetings with their CFO. Finally, they gave me $10 000. I was like: “Cool, that’s almost one month. We’re 12 months behind schedule.” A week later they called me to tell me they were bankrupt and I had to pay back the money because they were actually supposed to redistribute it to the investors first.

I said no and then came the lawsuit. By then, I had dug myself an $80 000 ditch. Fortunately, my editor in chief’s father has 40 years of law experience behind him and was able to step in. But, for all of 2013, I made a total of $10 000 with a net operating loss of about $100 000.

Wow. But you clearly didn’t throw in the towel at this point.

It was a bit of a wake-up call. It was kind of like going back to step one. But I think it’s the best thing that could have happened because it forced me to fire the Bangladeshi developers and do it all myself.

This is the start of 2014. You’ve just lost a heck load of money and probably spirits. What did you do?

The website was still generating good traffic. Spotify had only just launched in the States.

My first step was to switch advertisers to get rid of the guys that had gotten me into this shit. This time, I diversified by country so that if one of them were to end up not paying, at least I would still have other countries owing me money.

That was step one: Trying to get the revenue coming in again.

I was fairly successful on that but there definitely was some panic and I think that’s why I started freelancing as a developer. I put my name out there to try to get a couple of jobs. This was fairly easy because of Indie Shuffle’s reputation. There were a number of people who wanted to emulate that experience. They wanted to be able to navigate and listen and have a player that lines up songs. I said: “Cool, I know how to do that, so for $100 an hour I’ll do it.”


In step two, I basically started coding in earnest for Indie Shuffle. I had five years of tinkering behind me. I had learned CSS, understood HTML and was familiar with PHP through WordPress. I couldn’t touch the iPhone and Android app because those are completely different languages so I just focused on the website.

And what has happened to the site since 2014?

I guess there are multiple ways to answer that. Indie Shuffle has gone through a lot of different experiences in the last couple of years.

One regards our traffic: As with most music blogs, our traffic’s diminishing pretty steadily. If the average day to day user has signed up for Spotify or Apple Music, they’re now paying $10 a month for a service. All your music’s on the computer, on your phone; it’s everything you could want and you’re generally not going out there to look for new music anymore. So that’s how, at this point, we’re at about 200 000 uniques.

These lower views also meant that advertising revenue started to diminish. In addition, the whole ad industry has seen a huge shift, they’ve completely moved away from these high premium agencies because I think everyone realised that’s a terrible idea. They’ve all gone towards ad exchange networks like Ad Nexus, Rubicon and of course, Ad Ex, which is Google’s. They’re these exchanges where you’re basically bidding on impressions and you’re paying a fraction of the cost. Advertisers are typically paying about 40-50 cents CPM in dollars.

What that meant was I was suddenly going from making $8 per thousand impressions down to 40 cents per thousand impressions. That assumes that you’re actually selling all of your thousand impressions. I certainly wasn’t when I was doing it for $8 but I also wasn’t doing it when I was doing it myself. You’re selling a third of your impressions at 50 cents a pop which means the other two-thirds are really not filled so our revenue just started trickling down and down and down and down.

Luckily I’ve turned that around in the last six months or so.

How did you do that?

We’ve really bolstered up Indie Shuffle’s news offerings. Modern day SEO is a lot less about targeting broader, long-term keywords and more about being on top of the trends.

I’ll give you an example: Let’s say the Gorillaz are coming out with a new album, there’s a lot of news about them. It’s very hard to compete in that niche, we’re going up against Pitchfork, BBC and Huffington Post. These guys are writing about Gorillaz because they’re huge. They’re trying to get a piece of the pie.

What you need to do from an SEO standpoint is go and look at what people are searching for around the Gorillaz and try to find an offshoot of that. We identified that people kept searching for what the Gorillaz look like in real life. There was no real good article about that so we published a post on Indie Shuffle. We just matched that keyword.

In addition, I launched SubmitHub last year. That’s just an easy way for people to send me music, upload it using a form, artist name, song title, streaming link. Then I would just get a dashboard with a play button where I could hit a thumbs up or a thumbs down with my decision. Thumbs up means I’m going to blog it, thumbs down means ‘nah’.

We’ve since signed up over 300 music blogs, Youtube Channels and radio stations and are making pretty good revenue. In total, we’re paying the media on the platform around $38 000 every month.

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