— lyle mckeany

I have played tens of thousands of poker hands. I also played professionally for a couple of years in a row back in 2005 – 2006.

Me @ the WSOP Main Event in 2006.That’s me on Day 2 of the World Series of Poker $10,000 Main Event in 2006.

My usual game of choice is No-Limit Texas Hold’em, the so called Cadillac of poker. It provides the ultimate in risk vs reward. At any point in a hand, you can bet all of the money in front of you. This leads to some stressful decisions on an almost routine basis. All of those thousands of hands and an intimate knowledge of the odds involved in the game provide me with data to tap into when faced with those decisions.

Being a successful poker player requires a healthy disregard for money and the ability to make sound decisions under extreme pressure.

This clip that I shared in my answer to the Quora question, What are some famous poker matches ever played?, is a great example of utilizing that past experience and knowledge:

That is one of the most incredible hands I’ve ever seen and neither player even had a single pair! Phil Ivey is arguably the best poker player in the World and has a database in his brain of hundred of thousands of hands played at the highest levels and stakes that exist. He uses his vast experience in situations like the one in the clip to make the bold decision to go all-in, crippling his opponent. He went on to win the tournament and over $1M shortly after this hand.

So, how does this relate to startups?

As all startup founders can attest to, running a startup company can be incredibly stressful. Too often, startup founders make the decision to pursue an idea for a product without knowing if anyone actually wants it or will even bother to try it, let alone pay for it. In other words, they go all-in before the hand is even dealt to them. Sometimes they get lucky and are able to create a successful product, but the odds are similar to hitting a jackpot on one of the slots on the main casino floor.

By utilizing lean startup methodologies, startup founders can determine if their idea is valid using data as their guide. If you’re a startup founder and you’re not familiar with the lean startup, stop reading this and go read Eric Ries’ book The Lean Startup right now. If you’re a startup founder who is familiar with the lean startup, go pickup/download a copy of Running Lean, by Ash Maurya instead. It is an essential how-to guide for founders who want to stick to lean methodologies in their company. The lean canvas, case studies, and example problem/solution interviews have proved invaluable to many founders.

Startups are highly volatile, especially in the early stages, so remaining focused on a goal and collecting as much data as possible is crucial. The lean startup mantra is build-measure-learn. If done diligently, there will come a time when it becomes obvious whether or not you’re onto something. Imagine how much easier things like funding raising, or even bootstrapping, would be if you could point to data that proves you’re on the right track. If the moment is right, you won’t be afraid to confidently push your proverbial chips into the pot and go all-in.

For an excellent account of what it’s like to play poker for a living, read this great Quora answer from Michael Shinzaki.

I’m always looking to connect and learn from new people. Please follow me on Twitter: http://www.twitter.com/lylemckeany

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I’m going to give this new Quora blogging thing a try. Working on that whole building an audience thing. I plan on cross-posting everything here though. But, if you’re on Quora already, or you’re interested in checking it out (it’s cool, trust me), come check me out there at http://mixingitup.quora.com/.

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Please follow me on Twitter: @lylemckeany

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Virtually everyone thinks that email can be a pain in the ass. Everyone dislikes it so much that it has been relegated to “necessary evil” status. We all continue to use it because everyone else continues to use it and no viable replacement has come along. I’m not even sure what a replacement would look like anyways. Let’s face it. Email’s here to stay for the foreseeable future.

Earlier this year, I was excited to discover Sparrow. I had only used it for a few months when they announced that they had been acquired by Google. I still use the Mac version of the app on my MacBook Air, but I’ve now moved onto the Gmail app on my iPhone since Sparrow never implemented push notifications. My hopes for a “fix” to the email ecosystem had been dashed. Until now.

About a month ago, I somehow stumbled upon Mailbox. It feels strange, but I’m genuinely excited about an email app. The app looks great and the gesture functionality is brilliant. The Mailbox team is trying to change the way their users interact with the inbox by completely transforming it.

I love some of the copywriting from their website:

We’ve come to believe email is here to stay. And while we can’t get away from it, we can change how we interact with it. We can put email in its place.

We’re taking the very best experiences from the apps we use everyday and applying them to this archaic medium. It’s a new way of looking at your email, but when you use Mailbox for the first time, we believe you’ll say “of course.”

My absolute favorite thing they’ve done with their landing page is the call-to-action. When you click the blue “Sign Up” button, a popup box appears where you enter your phone number, rather than your email. Well played Mailbox, well played.

Look for the app at some point in “the New Year,” as it says on their site. I’m looking forward to saying “of course” then.

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Back in August, I wrote about my experience in my old band, Pressure 4-5. It was mostly about how I came to start playing the bass and the whole story around my subsequent music career. In the post, I briefly described how a record deal works. Here’s an excerpt:

When an artist signs to a major label, they typically receive a signing bonus of some sort and an advance of cash, all of which the artist must contractually pay back through album sales.

Here’s a more succinct description of a recording deal via Earbits:

A recording advance (record deal) is financial capital provided to early-stage, high-potential, high risk, musical artists or bands.

Now, let’s compare that to a typical definition of venture capital from Wikipedia:

Venture capital (VC) is financial capital provided to early-stage, high-potential, high risk, growth startup companies.

They sound remarkably similar and there’s a reason for that. The business models for both are virtually the same. Bet big on companies/bands the firm or label thinks are promising and hope that 1 out of every 10 or so become the next AirBnB or Bruno Mars and make up for the 9 failures that didn’t work out.

Not surprisingly, the internet has changed everything.

The demise of record companies has long been predicted. With the rise of digital downloads, the increasing popularity of streaming services like Spotify, and the closing of brick and mortar record stores, the need for massive physical distribution is declining rapidly. That being said, I don’t think they’re going anywhere any time soon since the model works well for trying to create superstar artists. While I think VCs are doing much better than record companies, they’re certainly being threatened by crowdfunding sites like Kickstarter. And if the JOBS Act ever gets fully enacted, it will allow government registered crowdfunding sites to let people who aren’t accredited investors help fund companies in exchange for equity.

I remember telling one of my co-founders, Terry, about how similar the business models are. It was the day before I attended TEDxSonomaCounty. At the event, Pomplamoose performed and bandmember Jack Conte broke it all down better than I ever could.

Pomplamoose epitomizes the new internet economy that’s empowering up and coming artists, performers, and entrepreneurs. Their quirky style has garnered themselves a loyal following on YouTube. Singer Nataly Dawn even leveraged that fan base to fund a solo album on Kickstarter.

The new internet economy is here to stay. Record companies and VCs need to adapt or risk becoming another statistic just like 90% of the projects they fund.

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What Street Artists Can Teach Us About Marketing

I’m a sucker for street art. I’m not really sure why that is. Maybe it stems from my high school days and listening to hip hop. Who knows. While street art (a.k.a. graffiti) has been around for ages, it has only recently broken into mainstream culture and high-end art galleries as a legitimate artform. It can also teach us a lot about a company’s marketing efforts both online and offline.

The most well-known street artists are fetching six and seven-figure amounts for their pieces and one artist even booked a nice payout after the Facebook IPO.

What are these street artists doing right and what can marketing professionals learn from them?

Consistent themes, styles, and point of view

Take a look at the piece at the top of this post by Banksy. It creates a visceral reaction in me and that is also why it is one of the most popular pieces he has made. Almost all of his pieces give me that same feeling. They all make a statement and portray his worldview unequivocally.

“We can’t do anything to change the world until capitalism crumbles. In the meantime we should all go shopping to console ourselves.” — Banksy

Artists such as Edgar Mueller go for the wow factor. Many of his massive 3D creations have gone viral online, even “old school” viral via chain emails. Even the most fervent graffiti opponent’s jaw would drop at the sight of some of his pieces.

Marketing professionals should adopt a consistent branding approach and it starts with the culture and core values of the business. Always check to make sure campaigns fall within the purview of the company’s overall brand. If your company has a customer base filled with enterprise level customers, it’s probably not the best idea to film a Gangnam Style parody video and slap it on the front page of your website.

Let people talk, share, and spread the word

Street artists are very good at putting something out there and letting the word spread organically. Of course, this is done mostly out of necessity since what they’re doing isn’t exactly legal in most instances. In fact, some street artists would probably argue that a piece doesn’t qualify as street art unless there’s a certain amount of illegality involved.

One of the best examples of manufactured virality comes from Shepard Fairey. I’m sure many of you have seen the image to the right. What Street Artists Can Teach Us About MarketingIt’s what has become an iconic image of the wrestler Andre the Giant that Shepard created and plastered all over Los Angeles and the surrounding areas. I remember when I first saw the stickers back in the late 90′s in Santa Barbara. At the time I assumed, incorrectly, that it was some sort of skateboard related brand. Turns out, it was just Shepard trying to prove a point. He pulled off a massive branding joke and it paid off in a huge way for him. He now has a very successful clothing line and became famous for his painting of President Obama, even though it resulted in a very public lawsuit.

The moral of his story is that a great brand can be powerful. The designs and images used to convey your company’s point of view help you attract the type of customers you’re looking for. Here’s a simple example. When my startup company was looking for an email marketing company, I compared MailChimp to Constant Contact. Guess which one I ended up using. If you guessed MailChimp, you would be correct. The branding on the two sites is complete different. MailChimp comes across as more lighthearted and fun. I mean, their name is MailChimp, for starters. Constant Contact is a successful email marketing company, but they’re clearly going for a different, more corporate, client than a marketing guy like myself from a small tech startup company.

Create great content (or a great product if you’re a business)

The best street artists are masters at their craft. They’ve spent countless hours honing their style and techniques so they can reproduce them quickly in order to not get caught by the authorities. Some of the huge pieces they get away with are absolutely mind boggling. They are dedicated to their brand and will stop at nothing to have their voices be heard. That type of dedication to perfection is contagious and it’s part of the reason why art collectors have swarmed to that artistic style of late.

Creating great content or a great product for a business is similar. Whether it’s publishing great articles in the New Yorker or building the world’s first gyroscopically-stabilized “rolling smart phone,” the goal is the same. Create something that your customers love and want to flock to.

Marketing is a tough game. All marketing professionals are vying for their customers’ and potential customers’ time and money. You usually only get a few seconds to capture someone’s attention, make it count.

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For many years I was convinced that two spaces after a period and before the next sentence was correct. However, I discovered this article on Slate back when it was published in January 2011, which made me realize the error in my ways.

Here’s an excerpt:

Every modern typographer agrees on the one-space rule. It’s one of the canonical rules of the profession, in the same way that waiters know that the salad fork goes to the left of the dinner fork and fashion designers know to put men’s shirt buttons on the right and women’s on the left. Every major style guide—including the Modern Language Association Style Manual and the Chicago Manual of Style—prescribes a single space after a period. (The Publications Manual of the American Psychological Association, used widely in the social sciences, allows for two spaces in draft manuscripts but recommends one space in published work.) Most ordinary people would know the one-space rule, too, if it weren’t for a quirk of history. In the middle of the last century, a now-outmoded technology—the manual typewriter—invaded the American workplace. To accommodate that machine’s shortcomings, everyone began to type wrong. And even though we no longer use typewriters, we all still type like we do.

While it took me awhile to get used to not tapping the spacebar twice, I can’t imagine doing it now. Just think of all the spacebar presses I’ve saved. How much time saved it equates to over the course of an average person’s life is anyone’s guess, but it’s not inconsequential I’m sure.

These days I immediately notice writing with two spaces as it looks like the prose is filled with gaping holes. It’s distracting and, sadly, it takes my mind off what I’m actually reading. I’m sure I sound like a crotchety old stickler for the rules, but I don’t care. I need to spread the word!

I have referenced this article multiple times since reading it and I am always amazed by the pushback I get from my serial two-space offending friends and family.

Another excerpt:

What galls me about two-spacers isn’t just their numbers. It’s their certainty that they’re right.

If you’re one of these over-confident offenders, stop reading this and go read the article now

Now if I could only get better at typing and eliminate the ridiculous amount of times I hit the delete/backspace button.

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Watching movies is inherently a social experience. Most people enjoy telling their friends and family about the latest movie they rented or went to the movie theater to watch.

For over a year now, Netflix has been trying to change a law that prevents people from automatically sharing what they watch with their Facebook friends, even if they opt-in. The amendment is currently stuck in committee in Congress.

While I understand why Netflix wants to partner with Facebook, I don’t think their current approach is worth it for a couple of reasons.

The case for case-by-case

I don’t know about you, but I don’t feel comfortable sharing every single Netflix movie I watch on Facebook. The partnership seems great on the surface, but I think it would ultimately create a negative reaction from Netflix users, and probably some funny/tragic stories as well.

Netflix should instead make it easy for their users to share what they’re streaming on a case-by-case basis.

As Senator Al Franken said:

It’s a really good thing that people can easily tell their video company, “Sure, go ahead and tell people I watched The Godfather, but no, don’t tell them I watched Yoga for Health: Depression and Gastrointestinal Problems.”

All Netflix needs to do is incorporate the ubiquitous social sharing buttons in various places on their website, as well as during streaming, perhaps down where the volume control is, and at the end of the movie. I’m sure their growth hackers would have a great time doing A/B split testing to see which locations perform the best.

Facebook isn’t the only game in town

Sure Facebook owns the largest social media audience at nearly 1 billion people, but there are many others that would be ignored. Twitter has 500+ million users, Google+ has 400+ million, and LinkedIn has 175+ million.

Ignoring the other social media platforms is short-sighted. If I were to watch a good documentary on entrepreneurship, I might decide to share it with my LinkedIn business contacts. However, if I watch The Big Lebowski for the umpteenth time, I’d probably go with Twitter or Facebook.

A new metric?

If Netflix were to incorporate the social sharing buttons, it would create a new “most shared” category on the Netflix site. Social sharing would bring even more attention to the most popular movies and drive more traffic to Netflix in general. This would be a big win for both Netflix, the filmmakers, and the studios.

One of the biggest problems Netflix has had with their streaming service is getting their hands on great content. The reasons for not subscribing I hear the most are that they don’t have any new releases in the streaming section and that most of the streaming movies are crap. I agree with those reasons for the most part, but I’m still a subscriber for the hidden gems I find from time to time.

Netflix can leverage social sharing to not only increase the size of their subscriber base, but to get more studios on board after they see the amount of shares that people make. If more and more filmmakers and studios see the potential for exposure to their films, then they are more likely to come back to the negotiating table with Netflix.

Sounds like a win-win for everyone involved to me.

Edit: Come join the lively discussion on Hacker News.

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Over the years I have put myself out there quite a bit. As a result, my career has taken some interesting twists and turns. I’ve gone from professional musician, to assistant golf professional, to professional poker player, to insurance underwriter, to sales, and now entrepreneur (my official title is Chief Marketing Officer, but like any startup entrepreneur knows, all of us founders wear multiple hats).

My career has been eclectic, to say the least.

Some people have said I seem to jump from career to career every few years, the implication being that I need to pick something and stick to it. In my mind, every one of those choices was made for a valid reason at the time and I don’t regret any of them. However, I am absolutely shocked that I didn’t decide to take the entrepreneurial plunge much earlier in life.

I’ve always been one to take risks. Calculated risks. Some of which have been the most rewarding and exciting decisions I’ve ever made.

Even though the band ultimately didn’t work out and I never got as good at golf or poker as I would’ve liked, all of those experiences were hugely beneficial and have helped shape me as a person and business professional. I wouldn’t trade them for anything.

Now it’s time to shape the future.

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When in doubt, don’t settle.

When in doubt, ask questions.

When in doubt, choose the high road.

When in doubt, proofread.

When in doubt, raise.

When in doubt, be pragmatic.

When in doubt, surround yourself with friends.

When in doubt, tear down obstacles.

When in doubt, go for it.

When in doubt, win.

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