The Poker Episode
THE SHOW - Episode 4.3





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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All Startups Are Scams
THE SHOW - Episode 4.2





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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When Do You Call Yourself An Entrepreneur?
THE SHOW - Episode 4.1





Why do people hesitate calling themselves entrepreneurs? I meet entrepreneurs from all over the country -- these are smart, ambitious, even successful people who having trouble getting the term entrepreneur to roll off the tongue. And more often than not, it's because they feel like they don't know enough about startup to label themselves as an entrepreneur. This is ludicrous. And it makes me furious.

But I can understand the awkwardness of it. It's not like being a doctor or a lawyer -- there's no credentialed association to back up the fact that you studied and worked hard to become what you are. There's also a bit of sketchiness to it, those multi-level marketing and huckster salesmen who go with entrepreneur because it gives them a showy legitimacy.

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THE SHOW: Why You Shouldn't Chase Venture Capital
Episode 3.4: The Last One With Thad Lewis





In our final episode with special guest Thad Lewis, we talk about sales and we talk about funding, the way they're related, and how they're different. Thad Lewis is an NFL quarterback, and in that, he's got a couple of things working in his favor that the average entrepreneur does not, namely, connections and money. But this doesn't necessarily give him a leg up.

We talk about Venture Capital. Thad doesn't need it. Thad doesn't want it. But he could get it, and he can also get money from other sources (friends, the bank, etc.) Outside funding should be the last thing on the entrepreneur's mind until they absolutely know they need it, so we talk about that here.

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THE SHOW: Confidence is Everything
Episode 3.3 featuring 49ers QB and Athlete Entrepreneur Thad Lewis





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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THE SHOW: Hire What You Suck At
Episode 3.2 featuring 49ers QB Thad Lewis





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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THE SHOW: Why Startup is Like Being an NFL Quarterback
Episode 3.1 featuring 49ers QB Thad Lewis





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: How To Build Relationships With Investors
Teaching Startup: The Show - Episode 2.4





Just because your startup landed venture capital, that doesn't mean you're successful. And just because you've been offered investment doesn't mean you should take it.

If you and your investors don't have a solid relationship, it could spell the end of your startup. Or maybe just the end of your leadership there.

What starts as a discussion about emulation versus experimentation (and maybe a little man-crush from Colgan), turns into the finer points of authenticity, honesty, and relationships with investors. Investment means the clock is ticking and the runway is getting shorter, every day. Those relationships are going to get real critical, real quick.

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VIDEO: How To Get Noticed
Teaching Startup: The Show - Episode 2.3





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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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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