The Startup Guide to Hollywood

Photo by Milo Baumgartner

Photo by Milo Baumgartner

I wrote a guest post on startups working with the entertainment industry for the 500 Startups Blog. The piece has now been shared thousands of times, featured in newsletters such as MediaREDEF, Mattermark, and StartupDigest, and voted up to the front page on GrowthHackers and 


Thanks to Emily Parris Sandler, Andrew Skotzko, Sam Teller, Patrick Vlaskovits, Joey Flores, Casey Armstrong, Steve Manuel, Rob Ellis, Susan Su, Keyvan Peymani, Matthew Joseph, Kelley McKinney, Nate Redmond, Adam Lilling, and Eric Galen for reading drafts of the piece. Very much appreciated!

Playing the Saxophone – Time to Get Over My BS

Damn, I’ve been really nervous about posting this.

I can publish articles all day. I don’t consider myself a writer. But I find it effing terrifying to post a YouTube video of me playing my horn. Because at one time, I thought I was a “real” musician. Whatever that means.

I spend more time helping musicians these days (which is awesome!), than actually playing. It’s been years since I was able to get in enough practice hours or jam with friends regularly. Now I’m remembering the old days.

But playing the sax is still so fun. Probably moreso than ever.

I was with my buddy Andrew Skotzko a couple years ago, talking about playing the sax. He egged me on to start posting covers to a YouTube channel. I was too chicken then, but it’s about time I got over my BS.

So, to try to knock off some rust, here are my first two posts to YouTube — one’s a Joshua Redman transcription of Eric Clapton’s “Tears in Heaven” and the other’s from the Chromatik Tune of the Day Collection, “Magic” by Coldplay.

I’ll continue posting tunes here via YouTube. Nothing crazy, but hopefully it’ll help keeping me going!

Hope you dig ’em.

A Driving Range for Skipping Stones and 35 Other Product Ideas for the Taking

Skipping Stones

“What do you think about building a driving range for skipping stones in LA?”

– A text I sent to my brothers, Jason and Eric, a few months ago.

James Altucher cranks out posts, talks, and books about “How to Become an Idea Machine.” I love the concept. Being creative requires you to come up with lots and lots of ideas. Many will stink. A few will be great.

So I started putting James’ concept into practice. Every morning, I pick a topic to develop 10 ideas for in under 20 minutes. Sounds silly, but it’s an exercise to get my mind a’moving. I come up with ideas for albums, Chromatik marketing campaigns, products, blog posts, books, movies, and more. It makes my brain sweat.

Ideas are the easy part. Execution is where things get much more difficult.

I put together a few of my favorite product concepts from the last weeks below. My goal here was idea exercise, not company building. Some of the ideas stink. A few have potential. Feel free to grab any of these as your own. Or laugh at them. Whatever you’d like.

1. Nest for Sprinkler Systems

California and many areas around the world experience regular water shortages. Similar to Nest’s energy conservation goals, homeowners would be more conscious about water usage if they saw data around water usage for their lawn or shower. Not to mention, my sprinkler system is a nightmare. Would love to see an elegant solution here. (Influenced by Greg Brandeau)

2. Handyman Lessons

I didn’t ever learn how to build or fix things around my house. Growing up, I was more interested in music, sports, and girls. But I’d love to take handyman lessons now, similar to what you see with music lessons. $40-60/hour to come to my house and spend an hour teaching me how to repair things, build something, use power tools, etc. There’s only so much I can learn from YouTube.

3. Pandora for Alcohol

Like that beer? Cool, here are three others to try. Like that Speyside scotch? Great, here are five others you’d like in a $25-50 price range. The Alcohol Genome Project. I hate depending on the folks at Total Wine or online reviewers.

4. Driving Range for Skipping Stones

A place to skip rocks would be incredible in major cities. Relaxing, peaceful, and lush. $5 for a small bag of perfect skipping stones. Concession stand. Perhaps a yoga studio. Please, someone make this happen.

5. Music Publishing Transparency

Music publishing is a black box. Want to license a track for TV or film? Want to pay out royalties from an online music radio program? Good luck. Publishing catalog ownership data is a nightmare. It’s wildly difficult to access, and it changes regularly. A few companies — MRI, Harry Fox, MediaNet, CrunchDigital — track and hold this information tightly to their chest (for sometimes north of $10k/month). Or you can try to track down rights yourself by calling major music publishers (it’s as fun as it sounds!). Someone will break down these walls.

6. Disconnect Software

There are some interesting products out there already for desktop (SelfControl being my choice), but nothing that crosses desktop and mobile. We need one disconnect app to rule them all.

7. Investments in Individuals

Most venture capitalists say they invest in people. But they actually invest in companies, where the people are replaceable.

Well, a different approach would be investing in a person. Literally. We’re already seeing public investment in athletes (see Fantex), and it’s only a matter of time before the model expands to movie stars, musicians, entrepreneurs, financial experts, and more.

8. Caffeinated Water Filter

Not sure this is possible, but imagine getting your morning pick-me-up from a glass of water.

9. QA as a Service

Anyone developing software hires testers. Some are great, some stink. It takes certain technical/communication skills and diligence to be a great tester. What if you could hire a firm to be that “fresh set of eyes” to provide full-cycle testing? Could work on nightly builds, bi-weekly releases, or one-off major pushes.

10. AlwaysOn Microphone

Imagine a FitBit-like device that was an HD microphone, always recording. At any moment, you could tap the device, send the last 60 seconds of audio to an app on your phone to save, edit, or share to social. Perhaps some invasion of privacy issues. Perhaps some creepiness. But it would be incredible for songwriters, authors, people with long commutes, entrepreneurs, people in fights, and more. Could you imagine Kanye with this? It’d be huge.

11. Uber for IT Support

The next generation Geek Squad. You could even roll up in a VW Beetle, if you’d like.

12. Food Sensitivity Brand

Gluten is today’s hot topic, but more and more people are learning about food sensitivities. It’s becoming mainstream. There’s still an opportunity for a person/brand to take the helm in this space. YouTube Channel. Blog. Recipes. Book. Food Network show. And more. (Influenced by Patrick Vlaskovits, Eric Sandler, and Lisa Sandler)

13. Personalized Job Search Service

There are just too many places to look for jobs. Job boards, individual company websites, and more. Pay a monthly fee for personalized, aggregated job listings. Upsell for resume writing/review, interview practice, and more.

14. Smart Toilet

Go to the restroom, and the toilet analyzes your urine/fecal matter. This can be for simple data gathering. Or could be a first-detection system that identifies potential issues. If possible, this could actually be a game-changer. (Influenced by James Altucher or Tim Ferriss, I forget)

15. Deli Delivery Service

You can get anything you need from the grocery store delivered nowadays. Except for deli counter items. The logistics of this business are key, but people would love to have turkey, cheese, ham, or chicken salad delivered to their door regularly.

16. Tru-Fit Tshirt

It seems like everyone has issues finding tshirts they love. Different brands, different sizes, different cuts, different materials. It’d be great to get to try a selection of tshirts, delivered by mail. And once I select my brand of choice, I’d get 10-20 tshirts in a range of colors, prints, etc.

17. Woodwind Reeds Subscription Service

Niche, but woodwind musicians need reeds regularly. We always forget to buy more, and when we do, they’re expensive. Just send me a pack of my reeds of choice, monthly. I’ll pre-order for a year.

18. Mailer

Have all mail sent to a PO Box. The company securely picks up all physical mail, scans in each item, and sends you all mail via email. Anything that needs to be physically passed along (think checks, bank cards) does so automagically.

19. Daily Video Newsletter

Folks get dozens of daily newsletters. Some are great, and others they’ve just forgotten to unsubscribe to. None feature the best videos of the day, sent to your inbox based on interests. News, sports, comedy, etc. Would be great. Calling!

20. Columbia House for LPs

Nobody buys CDs anymore. But cool kids with record players still buy LPs. Would love the mail-order record club offering now.

21. Passover Food Line

2013 US matzo sales were $86mm alone. Just saying.

22. The Holodeck

Oculus Rift is just the first step. Someone’s going to crack to code to build a Stark Trek-like holodeck. We want.

23. Audio for Articles

Audiobooks are a $1.2B business. Podcasts are rapidly growing in popularity. This would be a B2B business — work with a content company (The Economist, Rolling Stone, etc), identify top content per week, contract engaging vocal talent, produce the podcast, and distribute/track accordingly. The end result would be “The Economist Podcast,” which features audio readings of the previous week’s top articles.

24. #Cover

Check out #6secondcover on Vine or #15secondcover on Instagram. Wildly entertaining, with some fantastic talents. Something to do here.

25. Hello Music for Sports Gear

Daily deals for sports gear.

26. Musicians’ Music Podcast

I love Marc Maron’s WTF Podcast, The Nerdist, and more. They do incredible interviews with comedians and entertainers. But there doesn’t seem to be a podcast that hosts major music acts with any regularity. A podcast would be an incredible format to chat with musicians about the recording process, how they make music, and more. This could end up being Nerdist for music. (Influenced by Corey Richardson)

27. Reliable Wireless Internet for Airplanes

For eff’s sake, I’m tired of paying $25 for 3 hours of airplane internet access that’s worse than my 1999 AOL dial-up connection. Someone please fix this.

28. IMDB for Music

Pretty straightforward model. It would be a data gathering nightmare (tracking session musicians, band members, etc), but would be an incredible resource to the music community.

29. Connected Black Box

There could be a way to securely sync an airplane’s black box data to the cloud. It would require a hardware and software solution, sold directly to airlines and/or airline manufacturers. There are incredible complexities here, without a doubt, but this could prevent worst-case scenarios.

30. App Marketing Consulting

There are hundreds of thousands of app developers, producing millions of apps across iOS and Android. Mobile distribution is a very different beast than web or desktop software. There seems to be a niche for an app distribution consultancy that mixes marketing, growth hacking, and PR for apps. Similar to 500 Startups’ Distribution Team, but for any app developer.

31. On-Demand Mental Health Assistance

Digital mental health practice, connecting patients with US licensed therapists and/or psychologists via video. Available via web or your mobile device.

32. Safe Religious Community

There should be a safe place online where people can ask religious questions. A respectful community, where you can feel free to ask questions and have faith-based conversations with community members and experts alike.

33. SMB Insurance

Make buying business insurance not suck for SMBs. Please.

34. Creator Analytics

Go ask anyone under 18, they’re not using Facebook or Twitter. It’s Instagram, Vine, Snapchat, and others. While creators continue to build out distribution on those channels, it’s still early days for multi-channel business intelligence.

35. Coin for Loyalty Cards

The tech industry went gaga for Coin last year. Cool, sure. But I’d much rather hang on to my credit cards, and have a Coin for all my loyalty cards (Costco, Ralphs, etc). Those take up much more space, and I wouldn’t really have any security concerns.

36. Noise-Cancelling Perimeter

Make a silence bubble around me, without having to put on noise-cancelling headphones. It would be a modern miracle for anyone working in an office, coffee shop, or even library. (Influenced by Andrew Skotzko)

The Basics of Sales vs. Business Development

Sales and Business Development

Too many folks use the terms “sales” and “business development” interchangeably. BD and sales are different beasts, so I thought it would be helpful to lay out the basics…


Convincing a potential customer to purchase your product.


Creating long-term value for your company via partners and relationships.


Focused on customers.


Focused on channels.


Numbers-driven 24/7.


Sacrifices short-term bumps for long-term value creation.


Measured by sales quotas, with expected quarter-by-quarter growth.


Measured by business objectives, whether that be distribution, marketing, or otherwise.


A scalable business function to drive revenue.


Regularly testing non-scalable things to drive exponential growth.


Cold calls are the lifeblood of success.


Cold calling means you’re not connected enough.


Measure, measure, measure. How many calls can you do in a day? What’s your sales conversion rate? What communication method converts best to a sale? How do we drive customer acquisition prices lower?


Calculate value constantly. Where can we get our biggest bang-for-buck in a partnership? What value do we create for our partner? What value does the partner bring to us?


Make a sale, hand it off to customer onboarding and support.


Manage a partnership through its lifecycle.


Sales team training, onboarding, and growth is expected with company growth.


BD teams are amorphous and rarely look the same from business-to-business.


Always be closing.


Always be hustling.


The best salespeople come from the school of hard knocks, rigorous on-the-job sales training, can think big picture, and have exceptional strategic quantitative skills.


The best business development people are well-connected, know how to navigate partner organizations, can craft a story, and have an exceptional eye for value potential.


A dirty word in Silicon Valley.


A catch-all title for every MBA grad coming to a startup.


Glengarry Glenn Ross. The Wolf of Wall Street. Tommy Boy. Mad Men.


Moneyball. Jerry Maguire. Entourage. Risky Business.

Sure, there are plenty of similarities. But sales and business development fundamentally aim for different goals. They take different people and approaches. Get it right, or pay the price.

Spotify vs. Beats – Making Sense of The Echo Nest and Topspin Acquisitions


Two acquisitions in one week by the major players in music streaming. Beats v. Spotify. And interestingly, they characterize the different strategies each company is taking.

“Beats Music Acquires Topspin.”

“Spotify Acquires The Echo Nest.”

Beats is your artist-friendly, human-curated music service. Super Bowl ads with Ellen. Artist endorsements. AT&T family pricing.

Spotify is your all-encompassing music platform, with great recommendations and social connectivity. Biggest catalog. Free options. Current market leader.

The paths make sense.

Beats has a competitive advantage with artists. It was a gaping void in the market left by Spotify, Rdio, and others.

Spotify was first-to-market and is scaling towards their IPO and beyond.

Similarly, the acquisitions make sense.

Beats acquired direct-to-fan platform Topspin to increase their offerings to artists. They’re aiming to be the artist-friendly music streaming service. The hope is that as more artists love Beats, more music listeners will follow.

Spotify is trying to scale. They have free options for music consumers, they’re available across any device, and they have the most robust catalog. The Echo Nest developed best-of-class music intelligence APIs, used for curation to drive music discovery. If Spotify can make a huge leap forward in music curation/discovery and broaden its’ developer community tools, it’s a game-changer.

But don’t be naive. Both acquisitions were a shot across the bow.

Spotify integrated Topspin’s ArtistLink less than a year ago. Now that Beats owns Topspin, will that continue?

The Echo Nest powered Rdio, iHeartRadio, XBOX Music, VEVO, and more. Do you think Spotify will allow direct competitors full access to APIs that they spent $100mm+ on?

Who knows? But things are heating up.

Spotify. Beats. Pandora. Rdio. Songza. Deezer. Grooveshark. Slacker. Earbits. The list goes on and on.

Is this a winner-take-all market? Or is there room for more than one?

Acquisitions. Consolidation. Mobile carriers. And more. Coming soon to a music streaming service near you.

What Tim Tebow Taught Me About Playing Music

Tebow Music

I should not be thinking about Tim Tebow anymore. We are a couple years removed from Tebowmania, his late game heroics, and that ridiculous Tebow touchdown stance.

He joined the New York Jets last year and got cut. Then the New England Patriots. Cut again.

Heck, I’m a Dallas Cowboys fan. I should be worrying about Tony Romo this offseason.

But when I saw Tim Tebow’s Super Bowl commercial last month, it reminded me why he is still part of the conversation today — he smiles through the struggle.

Seriously. Think about it. Though winning a few games with the Denver Broncos, he has all but failed as a starting NFL quarterback. No team will sign him. But he is still working hard, struggling, and smiling for the cameras.

I’m sure Tim Tebow would love to be a Super Bowl-winning quarterback. Maybe he will be some day, who knows?

But his journey highlights important lessons that any musician or creative can relate to.


Tim Tebow was a high school football star. He led Florida to two NCAA national championships and won college football’s biggest award, the Heisman Trophy. And though scouts questioned his ability to play at the highest levels, the Denver Broncos selected Tebow in the first round of the NFL draft.

Big fish, small pond.

I can relate. Growing up, I was the best saxophone player around. I won national awards, got all the solos in jazz band, and gigged around LA. I then went to UCLA on a saxophone scholarship, thinking that I was going to be a professional musician.

Big fish, small pond.

You may already know Tim’s story. He won the starting gig with the Denver Broncos. Struggled. Squeaked out a few fourth quarter wins and limped into the playoffs. Pulled of a miraculous win in overtime against the Pittsburgh Steelers. Crumbled against the Patriots in the next game. Soon thereafter, the Broncos cut Tebow. And he hasn’t started an NFL game since. He is currently unsigned.

My story is less exciting. I was fortunate enough to go on the road with some incredible musicians, playing the US’ biggest venues. But I rarely got the solos or accolades. I got a taste of being a gigging musician, fighting for work, and struggling to make money. It became much less sexy. I didn’t love the life. So I left and found another path.

Being a big fish in a small pond can feed you false signals. Awards, beating local competition, and praise make you feel great. Sure. But you need to put it in perspective.

There is always someone bigger, better, stronger, faster, better-looking, or more skilled than you.

Entertainment has never been more accessible. Everything is global.

If you want to perform professionally, you have to figure out how you stack up against the best. How do you stand out? What unique skills can you acquire? What competitive advantages do you have? How are you going to develop an audience?


People love Tim Tebow. I mean, really love him. He developed a sports following only rivaled recently by Jeremy Lin. His fans idolize him on and off the field.

If he hadn’t cultivated that audience, would we still be talking about him? I’m honestly not sure. Some folks say that his fans are a liability. Some say that his fans are the reason a team should sign him (i.e. Jacksonville, to fill those empty seats!).

The reality is, he has not proven himself a reliable NFL starting quarterback. But his fans support him tirelessly. Perhaps there is a religious undertone, yes. But more than that, he spent years building his fan base. Meeting them off the field. Doing charity work. Speaking engagements. Interacting on social media. Shaking hands and kissing babies.

Tebow Baby

Apply this to music. Do you have 10 people Tebow-excited about your music? 100? 1,000?

Kevin Kelly’s concept of 1,000 true fans rings true across any entertainment medium. If you have a following, you can make a business. If you have a following, you will get opportunities. If you have a following, they will support your through the good times and bad.


After being cut by the Denver Broncos, Tebow and his agent had conversations with nearly every NFL team.

He was comfortable with getting NOs from almost everyone, so that he could find at least one YES.

Willingness to get 30 NOs for every YES is daunting. But that willingness also landed him a gig with the New York Jets.

Did you call thirty venues to land a showcase spot? What about thirty music schools for a teaching position? Thirty managers? Thirty agents? Thirty lawyers? Thirty investors?

Truth is, most people do not put themselves in the position to get a YES. It takes persistence and a willingness to hear many NOs.

“If you aren’t getting rejected on a daily basis, your goals aren’t ambitious enough.” Chris Dixon


Moral of the story, don’t take yourself too seriously.


I purposefully neglected religion thus far.

The truth is though, Tim Tebow is deeply religious. He talks about it regularly. But more interesting to me, he seems to have his priorities in order.

He balances personal with professional obligations. He seems to keep himself grounded, amidst 24/7 news coverage and more publicity than anyone could ask for. People close to him heap kudos on his character, integrity, and outlook.

I have made a lot of mistakes professionally and personally. I am still learning and growing. But when things get difficult, I lean on my family and friends for support. Nothing is more important to me.

For some people it’s family. For others it’s faith. It doesn’t matter what it is. You need something.

As demonstrated by Tebow and others, you cannot build self-worth solely on your career. Professional stumbles should not crumble your self-worth.

There’s more to life than your job. There’s more to life than music. There’s more to life than being creative. Everything in balance.

Tim Tebow obviously isn’t struggling for money, exposure, or opportunities. I know. The guy has millions of dollars and fans that could fill stadiums.

But he is unemployed. He is still struggling to make it back to the peak of his profession.

And Tebow’s struggle has been very public. Maybe it will have a happy ending. Maybe it won’t. But I do know that it has taught many of us lessons about “the journey.”

Folks always talk about achieving your goals. But goals are lofty. It may take thirty years. Or change along the way. Or never even happen.

Are you supposed to just put your head down for thirty years, hoping that one day you’ll achieve your goal and supreme happiness?

No. That’s ridiculous.

Smile through the struggle. Enjoy the journey.

The Artist CEO, Part II

Continued from The Artist CEO, Part I

Jay-Z Artist CEO

The best creatives are part artist, part CEO. You’re creating a business. You need to choose your path forward.

In Part I, we discussed finding product-market fit. It may take a few months, or a few years. But the road towards product-market fit is essential to finding your artistic voice and community.

Once you’ve nailed your product, then it’s time to build a business, which means dealing with your finances, team, building your platform, and having real goals. That’s what we’ll cover here.


A CEO is responsible for overseeing the financial operations of a business. You need to manage the bottom line.

Now’s the time to find a path to sustainable cash flow.

Cash flow positive is a position that every business owner dreams about. It’s the point when your business net revenue exceeds your monthly expenses. Meaning, you can live off your business without needing additional capital.

Let’s look at expenses first.

How much money do you need to live every month? Not how much are you making now. Not how much do you wish you had in your bank account. But how much, given your current circumstances, do you need to live?

If you’re a single person living in a major city, I’d guess that you can sustain on $2,000 – $3,000 per month.

Rent – $1,000

Internet, Phone, and Utilities – $200

Food – $500

Fun – $250

= $1,950 per month

That can fluctuate, depending on bills or circumstances. But you get the picture. Break down your spending every month to set a target revenue goal. It doesn’t matter whether that’s $2,000 or $10,000 per month. Just know your magic number.

The equation is simple from there. Your art needs to generate more income than your magic number. Until then, you’ll lose money every month and need investment capital (from another job, parents, loans, selling a kidney, etc).

We’re not covering how to make money here. How you generate income from your art is up to you. But, know that if you’ve taken the product-market fit and 1,000 true fans concepts seriously, there are plenty of ways to monetize your audience.

Three of my favorite recent examples are…

  • Patreon – Web platform that enables fans and sponsors to support the artists they love. Patrons pledge support to creators on a recoccurring basis for each work created, empowering a new generation of creators the ability to (hopefully) make a living off their passions.

  • LeanPub – Web platform for authors to write, publish, and monetize in-progress books.

  • See.Me – An artist-focused community of over 1 million people, across web and mobile. Creators post what they love and earn money from their creations.

You’re the CEO. Manage the budget.


We can only do so much alone. Once you hit an inflection point, surround yourself with the right people — whether that be a manager, lawyer, or street team of friends and interns. Build your team.

But — don’t just hire to hire.

Go through this week marking down every task someone else can or should do. Write down every opportunity that falls through the cracks. Note any projects or ideas that aren’t being completed.

When you have a meaningful list, identify the skills you need on your team. Only then can you hire intelligently.

Nothing is more important than the people you bring a’board. A business lives and dies by the folks involved.

Take hiring seriously, and follow these three rules:

  1. No assholes. Life’s too short.
  2. Hires must be willing to work harder or more efficiently than anyone. (*This doesn’t mean more hours. As legendary UCLA basketball coach John Wooden would say, “don’t mistake activity for achievement.”)
  3. Hires must be the best, or striving to be the best at what they do.

Remember, you’re the CEO. You want to build a brilliant, trustworthy team. If you have folks 10x smarter working with you, you’ll have more creative time. And fun. Yes, fun.

I’m still a work-in-progress when it comes to management, so I’ll defer to the best readings I know…

You’re the CEO. Build your team. Lead.

Boss vs Leader


Major entertainment companies — record labels, book publishers, movie studios — don’t invest in artist development anymore. Gatekeepers look for creatives with an existing audience and platform.

In years past, these same gatekeepers prided themselves on finding and developing talent early. But with social media and direct-to-fan platforms at our fingertips, gatekeepers now expect artists to do the work themselves before signing.

Do you have 250,000 YouTube Subscribers? A recording contract is in your inbox.

Can you prove that you can sell 10,000 books? Publishers are blowing up your phone.

Did you just raise $750,000 on Kickstarter for your indie film? An agent is already at your doorstep.

Only expect a major entertainment company to invest once you’ve already proven that you can move product. Plain and simple. They are not in the business of artistic risk, they are in the business of financing artistic expansion and distribution.

The point? Developing a distribution platform is half the battle in your creative business.

As I said before, building an audience and making money are different per artist. But I’m more concerned about your line of thinking.

You’re the CEO. Develop your platform.


What are your goals?


What do you want to accomplish? Making a living from your work? Win a Grammy? Make an hour standup special for HBO? Write a New York Times Bestseller?

Have vision, but don’t start by creating a five year plan. You’ll just be writing BS.

Instead of five years, look ahead five months. Where do you want to be? What do you want your business to look like? What are your revenue goals? Audience engagement goals?

Now look at your team. Have you articulated your goals clearly to them? Do they buy into the gameplan?

You’re the one leading this ship. Ultimately, you’re responsible. Start thinking like a CEO. Set goals. Go execute. Nobody else will do it for you.

To paraphrase one of my favorite writers on CEOs, Ben Horowitz — if you are a CEO and you feel awkward or incompetent when doing some of these things and believe there is no way that you’ll be able to do it, welcome to the club. That’s exactly how I felt.  So did every CEO that I’ve ever met. This is the process. This is how you get made.

The Artist CEO – Part I

Artists rarely think they’re starting a business.

Building something is difficult in any setting. But more than other industries, creatives struggle with the ambiguous path to success. The economics of creativity are dizzying. Most artists know how to create, but fail to recognize that art is only one part of their job.

“If you build, they will come” is a dangerous myth. Comedians believe it’s all about the jokes. Musicians believe it’s all about the music. Writers believe it’s all about the words. And it is…until it isn’t.

Talent and great art only gets you so far. Even (and especially!) the best artists put substantial work into customer development, audience engagement, marketing, and ultimately monetizing their creative output.

Making an analogy to the corporate world – your art is the product, and you are the company’s CEO.



Before anything else, you need confidence that your product is good enough to support a business.

You’ve recorded music, painted, or written jokes. Great. But that art was made in a vacuum. How do you know your product is good enough? What data tells you that you should be building a business?

In technology, we frequently talk about product-market fit. Meaning, you need to make a great product that satisfies the needs/wants/desires of a market. Enough to get them to part with dollars.

But how do you know if you’ve hit product-market fit? I contend that for artists, it’s a balance between gut feelings and data:


  • How does the audience react at your shows?
  • What do artist peers say about your product?
  • What do fans tell you via YouTube, Soundcloud, or DeviantArt comments?


  • How many audience members come to shows specifically for you? Are those numbers consistent, growing, or declining?
  • How are your social, newsletter, and/or website metrics trending? Have you surveyed fans to get a sense of their affinity to your product?
  • What do your online conversion rates of email capture or content sales look like?

The list goes on and on. It boils down to whether you’ve proven that people want and will pay for your product. That’s the golden ticket.

Be willing to do anything and everything to find product-market fit. Hold down a fulltime job, while practicing every night. Perform as a street musician in the downtown area every weekend. Show up to four open mic nights a week, ready to jump in with a ten minute set. Keep learning, iterating, honing your craft, gathering more data, and producing better content.

It’s worth mentioning that there are also a couple services to help in this process – Fluence and Clarity. Both are marketplaces for advice and constructive feedback from industry experts. Fluence is focused on creators and artists. And though Clarity is dedicated to business experts, you can find fantastic advisors in music, art, comedy, writing, and more to connect with. Get a fresh set of eyes on your project.

Be real with yourself – can you honestly say that you’ve hit product-market fit? If so, let’s talk about building a business…

Continued in Part 2, where we’ll discuss making money, putting a team together, and setting up a sustainable business. Dig this post and want more? Subscribe to get notified about new releases.

For Musicians: 8 Steps to A Million YouTube Views

YouTube Audience

I get at least a dozen emails a month from musician friends who want to build out their YouTube presence.

I don’t claim to be a YouTube expert, but I spend a good amount of time at Chromatik working with artists and the YouTube ecosystem. We’ve built the Chromatik channel to over a million views (led by the extraordinary Kelley McKinney), and I’ve worked on musician friends’ channels with over 50 million collective views.

Through the process, I’ve noticed some clear do’s and don’ts when trying to build a quality YouTube presence. If your goal is fame and fortune without hard work, move along. But if your goal is to build a lasting community for your music, then follow the general guidelines below to a million views and beyond…


Failure isn’t your biggest obstacle to success, it’s not even starting. Most people talk the talk, but never actually walk the walk. You want a great YouTube presence? Start making videos…today.

I know that there’s a tune you can crush. Maybe it’s Classical Gas, maybe it’s Twinkle, Twinkle Little Star. Perhaps 15 seconds of a popular chart? It doesn’t matter. Spend 30 minutes recording and uploading it to YouTube…today.

Start viewing YouTube as a sandbox for playing, performing, and sharing. Not everything you upload to YouTube needs to be perfect or professional quality initially. We’ll get there. But as a relative unknown in the YouTube ecosystem, you’ll want to just get comfortable with the recording and upload process first.


One of the YouTube myths I hear all of the time is – “I just need ONE video to strike it big.”

So what do folks do? Pour a tremendous amount of time, effort, and money into producing an incredible video. Cool. Assuming that you rocked and it miraculously went to the front page of Reddit, you now have 100,000 views and a couple hundred subscribers. Now what? Can you replicate that?

The unfortunate reality is that 100,000 views and a couple hundred subscribers doesn’t get you very far in the YouTube ecosystem. Not to mention, with over 100 hours of video uploaded to YouTube every minute, there’s a 1/1,000,000 chance of you achieving that result.

The myth is dangerous because it forces you into an assumption that “if you build, they will come.” Which, as many creatives – from musicians to tech startup founders – learn quickly, just isn’t the case.

So let’s focus on starting small and building a community. Without a miracle, the only replicable way I’ve seen to build a successful YouTube channel is by being prolific and regimented with content production. One of my favorites, Gabe Bondoc – now with 272k subscribers and 48 million views! – was phenomenal at this early on (thanks for the recco, Corey!).

You’re learning or writing new tunes every week, right? Great. Set up a regimen. Chose two or three days a week, every week that you’re going to spend 30-60 minutes recording a new tune and posting to YouTube. Not every tune needs to get 100,000 views. Rather, start with a goal of fifty views on each video, and work your way up. We’ll talk growing viewership shortly.


Your videos do not need to be professional quality, but they should look somewhat polished. Here are a few quick tips:

  • Don’t record in your messy bedroom, for goodness’ sake. Find a space that looks hip, or at minimum, neutral. You want to be the focal point.
  • Backing tracks are clutch when playing popular tunes. If you’re a solo instrumental artist, it adds a tremendous amount to your video performance to play the melody in context. You can find almost any backing track you need on iTunes.
  • Many YouTubers record audio first, and then mime/sync the video to get the visual right. Not saying that it’s the best way, but think about how you can most effectively record videos for quality and time investment.
  • If you’re not great at AV editing, I suggest investing some time into learning. If you need some help along the way, Fiverr has great folks who edit videos, design intros, and more for just $5.


YouTube is currently the second most popular search engine in the world. While bloggers and websites spend a lot of time thinking about search engine optimization (aka, how to appear at the top of Google search results), many YouTube creators don’t give the same amount of thought to their videos.

What if, when you typed in “Katy Perry Roar,” your video was the first search result? You’d get millions of views. Obviously that’s unrealistic, but you get the point. Where you fall in search results matters.

Check out the YouTube Playbook for some basic details on how to title and tag your videos. It’s important.


We’ve established that you’re posting great videos to YouTube regularly. Now’s time to build an audience.

Simply put, passively posting to Facebook and Twitter will only get you so far. Your video will get viewed by a few of your friends and family, and then disappear from the stream/newsfeed after a couple hours.

Before anything else, read 1,000 True Fans by Kevin Kelly.

To build a sustainable YouTube channel, you need to drive conversion to channel subscribers. And that’s going to take some hustle, both inside and outside the walls of YouTube. Most folks will never just happen upon your content and share it to their friends. So for the sake of brevity (another post on building an audience to come), here are a few thoughts to get your brain a’moving…

  • Regular, personal communication paths to friends and family, asking them to check out your videos and subscribe. Email Newsletter, Facebook messages, Twitter DMs, Instagram Direct, Snapchat, and more are all potential communication paths.
  • Make a clear call-to-action in your video and video description.
  • Sharing on video communities like wimp, Reddit, and Remember to respect the rules and community.
  • Outreach to bloggers who feature “Top YouTube Videos of the Week” or write about music closely related to your style/influences.
  • Work with friends and other YouTubers. See “Work With Friends” below.

The point being, you likely will not build a lasting YouTube channel by simply posting to Facebook and Twitter. Get hustling.


We talked briefly about SEO for YouTube. But the core variable with SEO is building content interesting to a target search audience.

People use YouTube search just as they do Google. They type in “Katy Perry Roar” or “Lorde Royals covers” with far more regularity than your name or “jazz saxophone.”

So, game that user behavior by covering the most popular music, happening right now.

Let’s take an example — if you were to create content on Michael Jackson’s “Beat It,” there are thousands of back-catalog videos already there that you’re competing with. Many with thousands, or millions of views. Hard to win, especially if you consider the low search volume today for MJ’s “Beat It.” Regardless of how popular the tune is in pop culture.

But if you create a video today for Katy Perry’s “Dark Horse” (or any other tune that spiked on the charts this week), you’re entering the search competition with the same amount of views, time, and opportunity as anyone. And the search volume for a tune like this is 100x that of Michael Jackson in its first four weeks atop the Billboard Hot 100 charts.

You may not love the most recent tune by Katy or Beyonce, that’s fine. Find a way into one of the top tunes, by layering in your performance style, technique, or a full-on remix to make it your own. If you hit the right cover and timing, I promise it will pay dividends in views and subscribers.


You’re only one person. You’ve tapped your network, hustled to get additional coverage, and done great thus far. But how do you expand your reach even further? Work with friends.

Pretty simple equation. More people involved = most potential reach. Collaborate on a few videos, and ask them to share to their friends. Or better yet, have their friends subscribe to check out future collaborations.

If you have YouTuber friends, there are a plenty of cross-promotional things you can do together too. YouTube’s written a great primer on this, so I won’t re-create the wheel.


This process is going to take a serious investment of time and effort. Building an audience for your music is not simple, but hopefully I laid out pretty straightforward guidelines for success. You going to need patience and resiliency. 1 million views won’t come overnight.

As a musician, most of our dreams circle around playing for an audience. But we all wish that we could get more stage time with a captivated crowd. YouTube can be that vehicle for you. You have the talent. Now put it into motion.

And if I can be helpful in any way, please feel free to send me an email (mdsandler at gmail dot com) or message on Twitter (@mattdsandler).

Guitar Center: Interview with Metallica’s James Hetfield

Great interview and quick jams with Metallica’s James Hetfield at Guitar Center.

On his early decision to play music — “It was one of these forks in the road, that was pretty pivotal to my life. Do I want to be second string playing football, or do I want to be up on stage, with a mission, speaking through music?” (2:55)