Mentor Madness

Mentors help entrepreneurs without asking for anything in return.

These diamonds in the rough may be hard to find and the vulnerability to ask others for help can feel heavy, but don’t be afraid. Most entrepreneurs and intrapreneurs enjoy helping others. Not everyone is graced with extra time, but there are good mentors in every community. Local mentors provide huge in-person value and the online universe offers infinitely more ways to find good fits. The wider your engaged network is, the more strategic you can be when selecting mentors as well. Even with a wide spectrum of options, take time to consider whom you trust and who will trust you in return. Be respectful of everyone’s time, but don’t be afraid to approach the giants you admire most.

As an entrepreneur talking with potential mentors, be transparent about your situation, concise with storytelling, and clear with specific needs. Spell out your vision, the current state of your business, what makes you a pain reliever vs. a vitamin, and how this mentor’s experience could help you navigate the fog.

As you explore mentor relationships, it’s unlikely one person can support you on all fronts. This means you must get comfortable working with multiple mentors.

The more one mentor can help, the more attention they deserve. When you give a mentor more attention, it should not feel like they need to do the same. Approach each exchange with composure. Make it convenient for people who aren’t required to care. Go out of your way to be effective and efficient. Learn how someone likes to communicate and make detailed emails concise. Answer questions directly and find ways to keep connecting new dots. Think about deliberate deliverables. As things come together, slow play the delivery of assets and things you want to discuss. This will keep progress from feeling too heavy. It also creates space for concentrated feedback on more specific topics. A mentor who helps you in a meaningful way will rarely disappear, so there’s no need to overload them with too much at once. This practice helps you stay on top of ongoing conversations, while also allowing mentors to add more precise value. Optimizing mentor relationships this way will inspires trust, action fueled by accountability, and solidify a lasting sense of accomplishment for everyone interested in your success.

Along with learning from mentors, consider being a mentor yourself! Success (and failure) leaves clues so no matter what you’ve achieved in life, you have wisdom to share.

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Interested in mentorship? Here are characteristics to consider.

If you decide to offer your time in this way, be generous, but also realistic about how you can help. Mentoring can become a nagging task if you’re stretched too thin and the moment you feel resentment, the quality of your support diminishes. To avoid this pitfall, be upfront with the time you’re willing to commit and deliver whatever is promised. When volunteering a significant amount of time, be sure to feel at peace about the impact you’re making.

Your time spent mentoring should feel easy, efficient, and fun, yet challenging and rewarding as well. A #GiveFirst mindset paired with an authentic connection to founders you care about creates space for honest feedback and a magical experience for those who learn, earn, and then give back.

Weekend Sprint

We just wrapped up Startup Weekend Iowa.

This was an online event, so our organizing team compressed what is normally a 54-hour, localized, in-person hackathon… into just 26 hours of people talking, typing, working and connecting together without the barrier of location.

Thanks to our own Wizard of Oz, virtual interactions were seamless and I was set free to creatively facilitate this high stress, no risk experience. It was energizing to have 25 participants and 15 mentors connecting to build two companies that pitched head-to-head for esteemed judges on demo day. This was a statewide event for Iowa, but the international element was in full effect as we also had new friends teleporting in from Canada and India to participate. While most of the event was hosted in a private platform that we called “the venue”, here’s a YouTube link to “the stage” where our keynote kickoffs and demo day were live streamed.

These weekly reflections, which I’ve been calling Roasted Reflections, are purposely timeless, but I share this brief event recap because it reminds me how easy it is to build when only a few people decide to work together. Yes, in-person gatherings create more random, serendipitous interactions, but I continue to marvel at how new interactions can be so efficiently ignited through these online interactions.

This was actually my first Startup Weekend experience! In the past, I convinced myself that my career portfolio was too full to build yet another new company. The infrequency of a local event and the anticipated time required were also factors in my past decisions, but now I realize, this combination of considerations led to a misguided assumption.

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You hear this tweetable thought often, but smart people change their minds all the time.

Startup Weekend can be a place where participants come together to build a business idea into reality, but it can also be a wonderful chance to catch up with friends, learn a new trick, mentor people exploring their own entrepreneurial spirit and/or simply observe some magic in action.

As one of the organizers and lead facilitators, I enjoyed a front row seat that allowed me to commentate the weekend while helping two teams build ideas into reality.

The energy of this weekend sprint was remarkable, but I noticed something as we all sat back and virtually celebrated demo day over a few brews during afties. It felt like the last day of summer camp. Everyone had been working alongside each other and while closing things down felt bittersweet, you could tell everyone appreciated the opportunity. This group had done something they were proud of and there seemed to be an unspoken premonition that Startup Weekend was not the last time these starters, makers, doers, and dreamers would come together to collaborate.

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Building alone is easy. Find friends to make it fun.