I had a Professor in College who taught The Psychology of Drug Abuse. He opened the class with a pretty powerful statement to provide context for his qualifications. He said: “I started my career as a Pharmacist. I did that because it was best place for drug addicts like me to get easy access to quality drugs”.

After mouths hit the floor and everyone looked around wondering if this was legit/true or just for the shock value, he went on to describe how this TRUE set of experiences gave him a unique ability to help other addicts (after he personally recovered, of course). He went from that awful position of a drug addict with access to pharmaceutical grade drugs, to an addiction counselor, to the head of the State’s addiction programs, to being a Professor, Speaker, and devoting his life to helping others. He has certainly saved lives and positively impacted thousands…

But the thing that struck me from that moment was that he was in a unique position to help, as he’d legitimately been in their shoes.

The Value of Having a Tour Guides

In my last post, I talked about the value of swinging for the fences and sometimes, if not often times, striking out so that you could in fact hit home runs. Post here if you missed it. The motivation for that post came from a powerful meeting with my mentor where we talked about removing the shellac we tend to post on social media (by highlighting only the wins), The other thing that kept coming to mind after our meeting was the concept of great TOUR GUIDES. Mentors are kinda like tour guides. Rehab counselors are kinda like tour guides. Great teachers are kinda like tour guides, and the best guides are always the ones who have been in your shoes. They can relate to you. They know how you feel. The emotions you likely have. The mistakes you are likely to make.

Imagine you are dropped in a foreign city for the first time and are looking for a famous statue. A city where there are no signs in your language. You stumble around with emotions oscillating from excitement to nervous to outright panicked and back. Wrong turns, dead-ends, bad directions from locals who don’t understand you, and on and on you go. Eventually, you find your way to the statue, and you are reminded WHY you came. You take a picture, post it on social media, and move on with life.

Now imagine you go back to the city again. You can get to the statue a little faster. You are a little more comfortable, and, since you are calm, you enjoy the scenery along the journey. You still make wrong turns but recognize a few landmarks that served you well on the first journey, so there really is no panic. It is deja vu experiences, smiles, adventure, and, importantly, achievement (as you make it to the statue again).

So the third time, you take a friend who has never been. Guess what, you are now an incredibly valuable tour-guide. Not only because you can find the statue, but because you know where the dead ends are, which streets to avoid, and what landmarks to look for. You can point out some cool things along the way. Your friend is relaxed because you have been there before. You are a great tour guide because of your mistakes and your FULL set of experiences, not just the ability to find the statue. 

Entrepreneurs as Tour Guides

The worst thing that we as entrepreneurs and tour guides can do is exclusively focus on our pictures by the famous statues (proving we’ve been there), when what makes us such good adventurers ourselves and tour guides to others isn’t really the statue… It is our ability to navigate the backstreets of the cities people want to visit because we’ve been there before.

So, go explore the foreign cities of entrepreneurship but take a tour-guide. Find mentors, advisors, and people who can help you along your journey. 



I am (after a bunch of wrong turns, a few pictures with statues, and some really cool experiences in the backstreets) now working as an Entrepreneurial tour guide.  So if you need help navigating, I make a pretty good guide. Engage with me as a friend on the journey: maclackey.com/friend

Yours in startups,


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