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Five Roles of Startup: Vision
Founding, Leadership, Management, Product, Future
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One of the truest descriptions of an entrepreneur is a person who has to do a lot of different things at the same time. The term for this has always been "wearing a lot of different hats." I don't like this term, mostly because it implies that you have to take your leader hat off to put your builder hat on.

The truth is you have to stack several hats on your head at once. Like Bartholomew Cubbins.

On any given day, an entrepreneur must be a leader, a builder, a salesperson, an accountant, and do several other jobs. As the company grows, you can hire other people to do some of these jobs for you. Hopefully, the people you hire will be better at these things than you are.

If you think about all the things an entrepreneur has to do, it can be overwhelming. Maybe you're an expert at one or two of them, or maybe none of them, and that's OK. Maybe you're good at a few others. Maybe you stink at finance, or sales, but if nobody is paying the bills or bringing in money to pay those bills, your company is not going to last long.

I'm not going to talk about every job at once. Much like when I wrote about the Five Stages of Startup and broke the timeline down into a simplified roadmap, I'll reduce the dozens of jobs an entrepreneur needs to do down to five basic roles you have to fill.

The five roles I'm discussing are general, but intended to identify everyone inside and outside the startup's organization. You must have someone playing all five roles, and most of the time two or more of these roles are going to be played by the same person.

First off, here are all five roles, because before you dig deeper into any of them, you should be aware of what they all are:

Vision -- Founding, Leadership, Management, Product, Future. This is the one I'm talking about now. There is also:

Build -- Design, Engineer, Perform, Deliver, Support

Sales -- Salespeople, Marketing, Business Development, Public Relations

Operations -- Human Resources, Finance, Legal, Administration

Growth -- Investor, Advisor, Mentor, Service Provider, Community

Vision determines company direction and momentum, primarily focused on making the product better, the sales stronger, and the company bigger.

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The Summer of Startup 2017
You Don't Need a Break, You Have a Mission
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The Summer of Startup 2017 is underway. Here's how you can follow along and get a shot of motivation and education every day in June and July. Be a better entrepreneur at the end.

Join the Teaching Startup beta for access to all the content and interaction with other entrepreneurs.

Follow us on Facebook or Twitter for daily updates.

No strings. No BS.


For the last several years, I've been writing about the Summer of Startup. The idea developed around finding an entrepreneurial summer activity for my pre-teen kids, but it has since evolved into a theme for everyone I talk to.

Summer is just a different time. When you're in school, it's a huge downshift, of course. But even when you've moved on into the working world, everything still slows down from Memorial Day to Labor Day. Vacations are taken across your organization, kids have to be entertained and accounted for, and life just generally eases up a bit.

It's downtime, regardless of who you are or what you do.

Take advantage of it.

I'll tell you how in a second.

For us here at Teaching Startup, the Summer of Startup is going to be about turning this nice little niche we've carved out into a real, live thing. I've got four objectives:

1. Opening up the beta to those entrepreneurs who have been on the waiting list seemingly forever, which will conclude with opening up the beta to the public.

2. Building a more robust and useful website experience, making membership mean something more than access to all of the content.

3. Holding off on new episodes of The Show while we tighten up the definition of it, the chemistry, and the production.

4. Spreading the word of the mission to people who can help turn this into a business, including creating a deck for partners and investors.

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The Crumbling of Corporate Culture
Teaching Startup: The Show - Episode 1.4
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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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THE SHOW: Why Startup is Like Being an NFL Quarterback
Episode 3.1 featuring 49ers QB Thad Lewis
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This episode features a very special guest and extremely cool human being: San Francisco 49er quarterback and entrepreneur Thad Lewis. Aside from being a working NFL QB, Thad founded TL9 for his future after football and as a way to give back to the system that got him where he is. He's not alone as an athlete entrepreneur, and that's because there are a ridiculous number of parallels between sports and startup. We start covering them here.

Thad is funding TL9 himself. He's also overseeing all production, marketing the company -- hell, he's even shipping hats himself at the moment. You need to go to thadlewis.com and buy a hat, if just because Thad will be the one sending it to you.

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VIDEO: What Does Success Look Like? - Episode 2.2
Teaching Startup: The Show
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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 Get Noticed
Teaching Startup: The Show - Episode 2.3
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Getting noticed in startup is all about building relationships -- with your investors, with your customers, and with your potential investors and customers. Cultivating these relationships is one of the most important jobs for every founder, and it's a shame that a lot of entrepreneurs don't do it right.

WedPics co-founder Justin Miller is an entrepreneur you should try to be like, and not just because Jon Colgan and everyone he's ever met has said so. In this episode, Justin details how he establishes and maintains those relationships, and why they're so important. Getting noticed is about the long game, the slow burn, and there's rarely such a thing as overnight success.

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THE SHOW: Hire What You Suck At
Episode 3.2 featuring 49ers QB Thad Lewis
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As an NFL quarterback, Thad Lewis has a couple of things working in his favor that translate well to becoming an entrepreneur, including available capital and great connections. But there are also areas he's not 100% versed on, like technology and marketing. Oh yeah, he also doesn't have a lot of time on his hands. His day job is a little more than 40 hours a week.

Even the best entrepreneurs aren't going to be good at everything. And even the most well-funded entrepreneurs don't want to lose too much control by farming out too many parts of the business. Startup is be a constant struggle of learn versus hire, no matter how long you've been at it.

So where do you start? And how do you start?

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When You're an Entrepreneur, Confidence is Everything
Episode 3.3 featuring 49ers QB and Athlete Entrepreneur Thad Lewis
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We continue our discussion with NFL QB and entrepreneur Thad Lewis. Here's another way startup and sports run parallel. When you're an entrepreneur, confidence is everything. When you're an athlete, confidence is everything. Talent can only take you so far, it's confidence that's going to give you just enough of a boost to separate you from the pack.

But if a lack of confidence will kill you, overconfidence will kill you just as quickly. Finding the right mix, and how to go about getting to that mix, is one of the things we talk about in this episode.

On your startup journey, you're going to come across a lot of people who will tell you you're doing it wrong. What exactly will they tell you you're doing wrong? Just about everything. Wrong product, wrong market, wrong time, wrong place, wrong team. You need to have the wisdom to listen and adapt but still keep enough backbone to follow your mission when you know you're right.

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All Startups Are Scams
THE SHOW - Episode 4.2
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There's a fine line between being a dreamer and being an entrepreneur. Don't get me wrong, I mean this in the best light possible. Without dreams, without suspension of disbelief, without the ignorance of what can't be done, the entrepreneur is no different than the cubicle drone. One thing separates the entrepreneur from the dreamer: Execution.

There's also a fine line between being an entrepreneur and being a scam artist. Let's face it, if you're doing startup right, you're doing something no one has ever done before with no proof it will work, much less succeed. And you're trying to sell that vaporware, that dream, those magic beans, to customers or investors or both.

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One Bad Early Hire Can Kill a Startup
It Comes Down to Managing Expectations and Staying Agile
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Two years ago, an entrepreneur came to me with a dilemma. She had been approached by another entrepreneur who was being forced to wind down his own fledgling startup as his funding dried up. He was a one-person shop, he had made a decent run of it, but time was up.

Now he wanted to go to work for her.

I walked her through the dilemma. The guy had great tech and had been able to do a lot in a short amount of time with limited funds and resources. His was a tragic and all-too-common story. He raised a small seed round, crushed his milestones, a lot of investors were saying "maybe," and he just ran out of runway.

Happens.

So I asked her: Where's the dilemma? He didn't want a lot of money or equity. He wasn't looking for a specific role, but he came with ideas. He had connections, experience, and he filled a gap in a place she wasn't super strong. He came with zero baggage. He wasn't a jerk, no blemishes on his personal record.

She then explained, in a long, roundabout way, that he didn't fit the plan.

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The Poker Episode
THE SHOW - Episode 4.3
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In startup, everyone talks about failure and a lot of folks even encourage it -- Fail fast and fail often, they say. There's nothing wrong with this mantra, on its face, but it's rare that someone will actually walk you through what failure looks like and how to prepare for it. In startup, failure isn't the loss of your startup, failure is a long parade of pain.

In corporate life, failure is the loss of your job, maybe the loss of your house, your car, your family, everything you've worked so hard for. A lot of folks avoid startup because it seems like the risk is much higher to wind up in that aforementioned nightmare situation. But contrary to conventional wisdom, entrepreneurs don't love risk, they love to stare down risk, tolerate it, and mitigate it. If they're good, they eliminate it.

That got us talking about poker.

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