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Sharpening Startup Skills Through Mentoring and Advising

I became an innovator at a young age, developing my first digital publication as a bulletin board system at age fourteen, iterated until I graduated. During college, I worked in university information technology, then after college, I joined a startup. Soon thereafter, I started my first company, working toward making money from my innovations. My career after that point has alternated between starting my own ventures and working with other companies — mostly startups, but not all.

Then a few years ago, I took a break to write a book, that turned into speaking engagements and other writing opportunities, and one day I woke up and realized I felt somewhat removed from the startup community, even though I was still living right in the middle of it in Silicon Valley. I was still working directly with people in startups, but I wasn’t involved in one myself. So I decided to start advising some startups and doing some mentoring. It was one of the best professional decisions I’ve made in a while.

Here’s the thing: the tech industry can be a grind just like any other. It’s easy to get stuck in a rut and to do what you’re good at and not to stretch yourself — even in one of the most innovative places in the world. But when you’re faced with talking directly to other entrepreneurs and to put yourself back into their shoes, starting at square one, it brings a lot about that world back into focus.

Over the past year and a half, I’ve mentored entrepreneurs from all over the world through four different programs, I’ve been an entrepreneur-in-residence for entrepreneurship students, and I’ve advised startups in the US and overseas. Seeing these entrepreneurs — an incredibly diverse group — and observing what they all have in common and all of the excitement they have for their ideas, products, and services, has not only provided me with a lot of satisfaction from a giving back standpoint, but it has also helped me hone my own knowledge and skills as an entrepreneur. Why? I always have to be prepared because they ask great questions.

Today, I had the opportunity to speak with a group of entrepreneurs from multiple continents. They asked questions about everything from pitching to business models to market research to pricing to customer acquisition. And I think — I hope, anyway — that I answered the questions with enough context that it will be helpful. That remains to be seen, of course. It’s always difficult to know how much gets through, but I provided a detailed presentation and put a lot of thought into it.

This was just one in a series of these types of speaking and mentoring opportunities I’ve had in the past year and a half, but I feel like I’ve made some progress and improved in how I engage with these entrepreneurs as I’ve learned about their needs. While I’ve always been a big advocate for mentoring for the sake of mentoring to help others, I’m now also an advocate for mentoring, lecturing, and advising for the sake of your own development as well. The old saying goes that when you teach something, you have to know it even better than when you’re doing it yourself. I believe that’s true. So if you have the opportunity to give back in this way, I highly recommend it.

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