Mentoring entrepreneurs on a hike

Mentoring Entrepreneurs? Try Hiking a Mountain Together

I just got back from a hike up Mt. Sanitas with Yoav Lurie, CEO of Simple Energy (Techstars Boulder 2011), and Techstars Boulder 2013 company Shopventory. Shopventory provides simple, mobile inventory management for companies that use PayPal or Square. They just released their first product, and they are doing awesome – it hits a real pain point for small businesses.

This summer, Yoav and I have been taking different Techstars companies on morning hikes up Mt. Sanitas. Yoav leaves his house at 6:30 AM. I leave my house at 6:32 AM. We meet at 9th and Mapleton at 6:35 AM. We meet the Techstars companies at the Mt. Sanitas trailhead at exactly 6:43 AM.

In addition to Shopventory, we’ve hiked with BrandfolderKatoSnow Shoe Stamp, and Good April.

I’ve found the experience incredibly rewarding and it’s something I plan on doing every summer from now on.

As I thought about it on my way into work this morning, I identified several reasons why I enjoy it so much:


This is a big one. Too many entrepreneurs forget to take care of themselves. I am no exception. I’m turning 34 next month and I’m nowhere near where I’d like to be in terms of physical fitness. Living in Boulder constantly reminds me of that – world class athletes and healthy people are in abundance.

I find that getting a little morning exercise drastically improves my mental clarity and focus, preparing me for the challenges of the day ahead.

There’s a joke about the “Techstars Twenty” – the twenty pounds that Techstars founders put on while working 18 hour days for ninety days straight. It’s funny because it’s true. It’s an incredibly difficult time for an entrepreneur and the long hours take their toll.

By getting founders on a hike, they get some much needed exercise. There’s also nothing like standing on top of a mountain, looking down on beautiful Boulder, to put things in perspective.

Time Savings

As a CEO of a startup myself, my time is very precious and valuable. I get emailed about ten times a day for “a 15 minute coffee to get advice” – but unfortunately, I simply can’t fulfill all the requests. I use when I can, which is an awesome service for giving and receiving advice that Dan Martell and Co. have put together.

However, if the entrepreneur is local, I counter with, “want to go on a hike?” I’ve found that it filters out entrepreneurs who aren’t really committed to getting out the building and doing something.

In addition, I get to spend  time doing something I enjoy while spending time with one of my best friends (Yoav ).

Walking the Path Together

In a traditional meeting setting – like a conference room or a coffee shop – you are typically sitting across from and in opposition to the person you are meeting with.

On a hike, you’re both walking the same direction – literally. You’re also working together to achieve something – the summit of a mountain.

I believe this simple physical act of walking together helps align people in a collaborative mode.

Shared Values

As a Techstars alum myself, I particularly enjoy working with Techstars companies – specifically because they know the rules of the game and share a certain set of values.

Techstars founders don’t take anything personal – “It’s just data” – is the mantra and they understand Mentor Whiplash.

As a result, Yoav and I are able to give extremely candid feedback without worrying about offending anyone. And if you know Yoav and I, you know that we have no problem expressing our opinions.

I’ve also been through the program, can let them know what to expect, and can give them candid, actionable advice that can help their businesses in the future.

So, the next time someone asks you for a meeting over coffee, counter with an offer for a hike – or even a walk – instead. If you’re an entrepreneur, ask mentors to get outdoors with you – they’ll appreciate the freshness.

Have other interesting venues for meetings? I’d love to hear about them below.


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