For An Entrepreneur To Succeed, They Need Confidence

Teaching Startup builds confidence by answering tough entrepreneur questions

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Last week I took a call from a director of entrepreneurship at a small but well-known west coast University. She’s putting together her annual startup workshop program for the spring semester, and for the first time in the program’s history, it’s going to be all digital.

So naturally, she was curious about how Teaching Startup had bridged the digital learning gap, becoming an entrepreneur’s “continuing education” — in affordable bite-size pieces.

Her students, while talented and awesome, were also young, and the top entrepreneurial skill they lacked was confidence.

Not knowledge, not experience, not connections, not money — Confidence.

Her students learned confidence by spending the program shoulder-to-shoulder with mentors, advisors, and founders, exchanging ideas about the kinds of companies to start, what those companies could accomplish, and most importantly, how they operated.

Her fear was that with the program now forced to be 100% digital, it would, like most of the current educational experience — as she was witnessing it firsthand — feel much less than life-changing.

I laid out Teaching Startup’s approach of stripping away the traditional advisor process (and conventional startup bullshit), which in turn led to offering the most value, delivered in a novel and incredibly useful question and answer format.

She had one concern.

She was focused on the nuts-and-bolts, question-and-answer format of the Teaching Startup newsletter, and wondered if the insider nature of the content would drive away her already skeptical student population.

Absolutely not. In fact, all our data points to the opposite.

Over the last two months, I’ve had over a dozen inbound conversations with entrepreneurship directors at major and minor Universities (and also incubators, and coworking spaces). All of these conversations were sparked by the forced transition from a traditional learning environment to Zoom classes. All of them have started out at least a little bit skeptical of Teaching Startup and the newsletter.

But here’s the thing. If you want to learn about startup, would you rather get the opportunity for a quick Zoom call with an expert entrepreneur, or would you rather get multiple opportunities to listen in on working entrepreneurs asking expert entrepreneurs about real issues they were facing and next steps for success?

For one, it saves the “embarrassment” of not knowing which questions to ask, which stems from a lack of confidence. And also, all the answers are documented so when you do have a question that pertains to an issue you’re having right now, you don’t need to wait for the opportunity to Zoom with an expert.

And then you also have the opportunity to ask your own question when you’re ready.

This strategy doesn’t just apply to students. Entrepreneur confidence isn’t just about the courage to go out on your own, it’s the courage to make decisions for your startup without any roadmap.

Because when you’re an entrepreneur, you’re doing stuff no one has ever done before.

Try Teaching Startup for 30 days for free. If you don’t come away smarter and more confident about all the nuts and bolts of being an entrepreneur, just cancel. If you do see the value, use invite code LISTEN and you’ll get your first paid month after the trial for just $5.

After the free trial and the first month, Teaching Startup settles in at just $10 a month, meant to be affordable and useful to all entrepreneurs.

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