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VIDEO: What Does Success Look Like? - Episode 2.2
Teaching Startup: The Show





What does a successful entrepreneur look like? That's a pretty good question that shouldn't have an answer, but it does. There are two prototypes, the VC wannabe and the dorm room hoodie. And it's all dudes. And all of that needs to change.

But what about the rest of us? Do we entrepreneurs dress a certain way to stand out? Definitely. You need to cultivate your own look. It helps make people remember you. And the opposite, dressing for success, that doesn't help one iota. That's one of the things I love about startup. The ability to stand out or be contrarian helps you more often than it hurts you.

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VIDEO: How To Market a Startup - Episode 2.1
Teaching Startup: The Show
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I met WedPics co-founder Justin Miller about 10 years ago when he came up with the idea to establish a music festival as a marketing event for his photo-sharing startup DejaMi. You heard me. A music festival. Bands, venues, tickets, the works. I immediately fell in love with the idea for its boldness and its batbleep insanity.

Entrepreneurs are usually terrible at marketing, especially first-time entrepreneurs. And that's the core of this episode -- How To Market Your Startup -- where we dig into offline vs. online marketing tactics and how one must complement the other in order to see any success out of either.

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VIDEO: Survive Or Die
Teaching Startup: The Show - Episode 1.6





You hear this all the time as a cautionary tale in startup -- Survive or Die! There will be times when you have to make the decision to power through all of your mistakes or give up under the weight of them. Unlike a corporate job, in startup, there's no structure to blend into, nothing to hide behind, and no one is going to swoop in and save you.

That's part of the growth process of becoming an entrepreneur. It's hard to do and not always fun to talk about, but we found a way.

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Five Reasons for Startup: Elimination
Job Loss, Opportunity, Youth, Experimentation, Because Startup
At the outset of this series, I stated that there are an unlimited amount of reasons for someone to get into startup. So as we reach the end, the final breakdown of the final reason for startup, you probably won't be shocked that it's kind of a catch-all category. This is by design, because like most good journeys in life, we don't fully realize our reasons for embarking until we're already well on our way.

In some ways, I'm trying to persuade you into startup (or to stay with startup) with this series. I'm trying to convince you, you even might say I'm trying to trick you.

But I'm doing it for the right reasons.

When the startup community talks about startup, it's usually one of two ways. The first is a "go-for-broke" type of pitch -- usually a bunch of slogans you might find hanging on a wall in Successory-style framed image barf. I'm not a big fan of this, because I think it distills something awesome and complex into something pedestrian.

But I dislike the second type of pitch more -- the one that makes startup seem like a business class for people who have already been to business school. The folks that tell you that you're probably not ready, you'll probably hate it, and your cute little extension of the corporate world will lead you to a lot of pain and suffering if your financial projections are off by a few points.

Look, I'm not good at startup -- in the same way I'm not good at golf. The difference is, while I'll never show up on a professional golf tour, I can make a job, a career, even a life out of being an entrepreneur. So I'm going to keep learning, practicing, and playing.

Yeah, I need blind motivation at times, but it's MY blind motivation, not anything you can put a picture of a sailboat or a rainbow under to tell me to hang in there on Mondays. And I need financial projections, pitch decks, and market analysis, but there's NO UNIVERSAL MAP for how to do this. If I don't know the business of my business well enough to know my numbers, I need to focus on my business, not focus on where I put my hands when I'm pitching from a stage to a collection of uninterested VCs.

See? I'm already getting a little heated.

My point is: If you're not interested in startup for the Independence, Wealth, or Common Good that's inherent in it, and if your Personality isn't telling you that being an entrepreneur might be in your blood, startup can still be legitimate, satisfaction-filled way to spend your life. It may just come down to the process of Elimination.

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What's Your Biggest Weakness?
Teaching Startup: The Show - Episode 1.5





In this episode we focus on our weaknesses. Not necessarily our failures, but those pieces of us that we're bad at. Startup doesn't talk about weakness much. Failure stories are great, but 90% of the time they're humblebrags -- "We flew too close to the sun like Icarus!"

Honestly, that's not helpful. What we do is talk about what makes us fail, and succeed, in terms that everybody here can easily understand.

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Five Reasons for Startup: Personality
Contrarian, Type A, Persistence, Risk Tolerance, Leadership
I was built for startup. There's something about my genetic makeup, my upbringing, and my environment that makes startup right for me. It's not a job, it's not a career, it's not a lifestyle. It's what I do.

It may just be what you do too.

I've actually known this about myself my whole life. I've been building companies since the imaginary ones I built as a kid.

Yes, I had friends.

But I didn't discover an opportunity to get involved with startup until I had already been out of college for a year. In my world, you studied hard, you got good grades, you went to the job fair, you tried to get the job that everybody else wanted.

I did that. I hated the result. I didn't know startup was an option. I just didn't know any better. This shouldn't be.

There are a lot of personality traits that will lead someone to self-identify as an entrepreneur. Now, I should point out that even if it's in their blood, so to speak, it doesn't necessarily mean they're meant to be an entrepreneur, and it doesn't mean they'll be a good entrepreneur. It just means they need to test the waters at some point.

There are a lot of personality-based reasons for startup. Tons. So this isn't an exhaustive list of all the personality traits that might drive someone to become an entrepreneur. Your reasons will be your own, but the ones I've chosen here are the ones I see in a lot of great entrepreneurs, and when I ask them, these are the traits that they believe make them successful.

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The Crumbling of Corporate Culture
Teaching Startup: The Show - Episode 1.4





I founded Teaching Startup because I believe we're on the verge of a new era of entrepreneurship.

Those jobs we lost in the Great Recession? They're not coming back. They're being automated and streamlined out of existence. Then you've got all these kids coming out of higher education, hundreds of thousands of dollars in debt in some cases, who can't find a job worth their degree.

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Five Reasons for Startup: Common Good
Social Entrepreneurship, Profit First, Head vs Heart, Inherent Good, Always Be Good
I like good people. And I love people who do good. But I'm not going to come out and be all Yeah, go for it. Make the world a better place through startup.

If you were expecting that, I apologize in advance.

I've always been skeptical of social entrepreneurship or startup for the sake of doing good works. Startup with a cause? Awesome. Startup FOR a cause? Raised eyebrow.

Look, I'm a good person, too. Just like you. I do good things. I'm not saying don't blend your personal causes with your startup. I'm saying don't build a startup around a personal cause and expect that the magic of good to be what gets you over the finish line. It very well may and I hope it does. Just don't be naive. All the rules for survival still apply. All of them. You can still waste people's money in the name of charity. If you build something to help others and it fails, that's not OK.

As an entrepreneur, you have to separate business from personal. Always.

But I'll also be the first to tell you that common good should be a big part of your startup from day one. Because if it isn't, then you're no better than the powers-that-be you're trying to take down.

I know. It's a paradox. So let's dive in.

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Why Do We Make Startup So Damn Boring?
The Show - Episode 1.3





That time we talked about sucking all the fun out of startup, keeping people out of the club, and Joe's cut-rate accelerator idea.

Startup can be like a club where the people who are behind the velvet rope keep talking about how much it sucks in order to keep people from wanting to get in. It shouldn't be like that. We should keep preaching about how awesome being an entrepreneur is.

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Five Reasons for Startup: Wealth
The Lottery, Your Career, Investment vs Revenue, Foundation First, Don't Blow It
Let's talk about money. A lot of money. Big money. The root of all evil.

So you want to get into startup for the money. I get it. I'm not going to waste your time debating the merits of capitalism, morality, ethics, or throw a bunch of biblical tales at you. I actually admire your ambition. But there are some things you need to know.

Wealth is a legitimate reason for becoming an entrepreneur. As I discussed in the last installment, startup is full of unlimited possibilities, and in a lot of ways, startup makes it easier to get to where you want to be financially, once you throw out the conventional timetables and status symbols of the traditional American dream.

On the other hand, it's never easy to make money with startup, especially at first. Because unlike the corporate path, your mistakes won't get covered, you can't coast, and there's no large organization to get your back when your own personal results flag or you hit a slump.

And it's expensive to get your business to a point where the money coming in is both recurring and something you can count from month to month and year to year. That expense equates to either money out of your own pocket (or someone else's pocket who you'll have to repay before you get paid), or time, during which you won't be getting paid very much if at all.

But except for those two points on the near and far end, the rest of the Wealth equation for startup looks a lot like the Wealth equation for anything else. Work hard. Be frugal. Plan right. And if you're chasing startup only to chase Wealth, I mean, if you're chasing anything only to chase Wealth, you're probably headed into a world of hurt.

So don't do that.

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Welcome to Teaching Startup

Entrepreneurial mentoring at scale

If 99% of a startup’s success is based on team, why aren’t we identifying and educating potentially great founders at scale?

Teaching Startup is an educational network that delivers entrepreneurial mentoring at scale and in a unique, easily-consumable manner, to people of all ages and backgrounds. Using quality, tested content and an unstructured learning framework, Teaching Startup creates valuable new paths for anyone, regardless of experience, connections, or access, to embark on an entrepreneurial career. In short, Teaching Startup builds great entrepreneurs.

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