Raw. Humorous. Aggressive. Harsh. Bold. Honest. Jason Calacanis, entrepreneur, blogger, and current angel investor was invited to speak for The Phat Startup’s #BossUp series.

Hosted at the AlleyNYC on June 17, an audience of 100 made this experience an intimate one. It was great meeting Anthony and James(co-founders of The Phat Startup). They were really dope hosts and really made me feel at home.

Entrepreneurs from all over the City and as far as Los Angeles, CA were in attendance. Many of us were eager to soak in the information Jason had to offer us and to hopefully be able to execute on his guidance.

Jason’s rise to success today is the validation of his persistence and hustle. His main attribute is one that we all could do well to learn from: learning, learning, and more learning. Most of his business skills came from him going to the bookstore, buying a book, and sitting down teaching himself until he was perfect at it. Being average in anything is not in Jason’s self-manual. He truly is a self-made hustler.

The event entitled “Digital Hustle: Monetizing on Your Idea & Efforts w/ Jason Calacanis,” blew my whole mind. Personally, I have never seen someone deliver a discussion like that ever. He took us on long ride and we were in the passenger’s seat. Jason made us feel what he felt: the pain, the glory, the fall, and the rising to where he is today. Here’s my perspective of what I learned and what is essential to the grind of the digital hustle.

James Lopez was in charge of handling the discussion. You could see how eager he was to ask questions. After James asked Jason to give a two to three minute intro of who he was, actually eluded to a 40-50 minute lecture of his struggle, grind, and success of how he got to where he is today. James could barely squeeze questions in, but to his patience admitted that Jason answered a majority of the questions he was going to ask. Here are some topics that were discussed.

Jason really had a stream consciousness during his talk — you could feel the passion in his tone, gestures, and gaze. When asked what does it take to make it as an entrepreneur/start-up, his answer was simple:

[Tweet ““The person that writes and communicates has all the power. You have to come in the game and make your own lane.””]

He taught us that failure will ensue, but with failure comes exciting opportunities. Opportunities that are greater than your primitive ideas you had with starting your company. He instructed us to “stay crisp and sharp—keep acquiring skills, it’s all about product today.”

He really hit it home in all of us when he said that “all you need is one person to say yes” in getting someone to invest in your start-up. (Side-note: Jason says to invest more of your time in Twitter than Facebook, on the topic of building your audience.)

A question was raised on the topic of what’s exciting in the digital world today He countered with another question for food for thought. He asked “looking at aspects of our life, how we can make those more delightful?” A pause lingered, then came a succinct statement. “There is lots of room in the mobile…and efficiency in apps is most important.” He then stated that Google Glass is a disaster, and they’re not focusing on what the consumers want, and can afford.

Jason stretched this point out in discussing how he has some slight beef with Google. He said from being a content provider with them, that they treated him as a commodity. He ended with saying “that your company needs to build a direct audience.”

At the end of the discussion, the audience had a chance to come up and ask questions about anything to him. Here are some of the notable ones!

Q. How should product appear in the tech field?

A. Product needs to be beautiful, elegant, and simple.

Q. What makes you the A++ learner?

A. All that matters is skills, keep learning!

Q. What is your take on education and how important is it?

A. Hip-hop artists are the greatest entrepreneurs…Jay Z…Kanye. [Tweet “Value proposition for college is wack.”]

The way they’re teaching is wack! All of the greatest coders are self-taught…If you’re parents are rich enough, why not have them invest $50,000 a year for you in your vision in building your start-up.

Q. What is the difference between blind optimism and what “blind” millennials believe?

A. Finding motivation and building resiliency. Most days are a grind, it’s broken, you’re losing—you will get a break at some point. The difference is skill building.

Q. What is your formula for success?

A.You have to be willing to fail. A lot of people start now and don’t finish. A lot of things don’t get good ‘til year three or four. Keep expenses light. Make something that is crafted well. The world only cares about product that is a 9 or better. You can beat people by making better quality. It takes me 10 seconds to get interested in a startup. Logos are important. It’s either diamonds or coal.

Curious what Jason Calacanis is up to today? Follow him on Google+, Twitter and check out his blog!

Stay up to date and connected with The Phat Startup via their blog, Google+ and Twitter. Also, check out the dope events the AlleyNYC have to offer on their their Twitter and Eventbrite.

A HUGE thank you to the whole Phat Startup Team, AlleyNYC for hosting, and of course Jason Calacanis for keeping it real and teaching us what the digital hustle is all about. #BossUp!

Jason Calacanis

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