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6 Tips to Mentoring Entrepreneurs and Building Long Lasting Relationships

You’ve spent the last 10 years killin’ it in your field, and now you’re ready to pay it forward and mentor the next generation of lean, mean entrepreneur machines. But even with all of your experience, it’s not quite a simple as doing a brain dump while holding a founder in a headlock. Here are 6 tips that will help you become Yoda for business leaders and founders.

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Mentoring is hard work and not a one-size-fits-all endeavor. This is why we’ve put together a best practices guide to help soon-to-be-mentors through their first few appointments and create strong foundations with their mentees.

  • Do Your Research

You’ve made a connection, had an entrepreneur ask for your advice, and put a meeting on the calendar. Don’t go into that first meeting cold. It’s important to go into the session knowing about the individual and company you’re mentoring. A visit to their company website, LinkedIn page, and social media accounts can frame your conversation and cut down on precious mentoring time getting acquainted.

  • Create a Loose Agenda

As much as we hate to admit it, agendas make meetings more productive. Don’t hesitate to reach out to companies a few days before the meeting to get a sense of what they’re hoping to accomplish during the session. Not only will that help you break the ice, but it’ll provide you with a game plan as well.

  • Listen More, Talk Less 

You’ve been around the block more than a dozen times and everything you know about sales can fill an encyclopedia volume. But you don’t know the particular background and struggles of the startup that you’re meeting with. Before providing any advice, make sure to listen and really understand their business challenges. You can only deliver effective feedback after first understanding your mentee and their challenges.

  • Enter the Entrepreneurial Mindset

It’s hard to be an entrepreneur; after all, around 90% of companies fail. The entrepreneurs you’re meeting are putting their livelihoods on the line to create meaningful contributions to business, technology, and our society. Put yourself in their shoes and empathize with the hustle.

  • Use Your Network. 

If a startup is looking for a lawyer that specializes in contracts and you know just the guy or gal -- make the intro! Most founders are a-ok with cold introductions and, when in doubt, it doesn’t hurt to run the option by them. Entrepreneurs are always looking to expand their network so make sure they can tap into yours.

  • Follow Up 

You had a great meeting but now what? Don’t hesitate to forward an interesting article you read or a resource you found to companies you’ve mentored. If your mentor meeting included action items, follow up in a month to check on the company’s progress. That one-off meeting can turn into a long-term relationship, a referral, and perhaps even business. And hey, maybe equity is Chicago’s next unicorn.


Interested in becoming a mentor or teaching a workshop at 1871?  You can apply here.

Topics: Insights

Read the 1871 Blog for news about the Chicago technology and entrepreneurship community, as well as helpful tips, guides, and insights into the startup and investment world.

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