Entrepreneur. It’s a tough word…both to spell and to call yourself. It feels like one of those words that is so big and so bold. I almost feel cocky calling myself an entrepreneur. I am one though. I have been one for almost a decade now. I’ve started, and built, and innovated, and challenged the status quo across a variety of industries and mediums. Sometimes successfully, sometimes not.

Even today, inside a company of 100+ employees, I feel like an entrepreneur at times. I’ve also launched a side project to create a mobile app for social shopping. I am constantly thinking up ideas, then scratching them, then thinking of new ones, then scratching them. So is the way.

I think being an entrepreneur brings with it a love of leaping. Some of the most amazing people I know, including my current CEO, leap a lot. They leap into the unknown so much, I’m not sure they even notice. That’s a nature that I aspire to have more of in my life. It’s a muscle I hope to strengthen over the next few years so its a “gut-driven, somewhat calculated, well-justified, beautifully executed, value-providing” leap. Those are the leaps few of us ever get really good at taking, because they take practice. They take years of practice at times. They also take mentorship.

I was having coffee with my CEO the other day and he brought up mentorship. I’ve been super fortunate to have a variety of mentors over the years, and I simply can’t imagine standing where I am today if it wasn’t for them.

Our conversation dabbled on challenges that are well beyond my tenure in business, and growth challenges I’m feeling right now that stretch everything I know about who I am and what I offer as a startup lover.

This year has been, by far, my biggest challenge professionally as we grow SEOmoz both in customers, and in team. Things like culture, structures, mission, and more run through my head as I try to sleep–often unsuccessfully.

But perhaps the biggest constant in my life is those mentors, and their advice. I started thinking about the different voices I am lucky enough to have in my life, and I realized they really do come from different roads, and offer different perspectives. I thought I would run through the different types of mentors I believe every entrepreneur should have in their life. These are the ones that have helped me over the years.

#5. A friend that knew you before you started your own thing.

Perhaps no voice matters more than the one that knew you before you found startups. There is a realness there that is hard to find in anyone else. They knew you when all this was just a dream, or when you didn’t even know what a startup was. They can speak to your roots, and ground you when get lost in the startup haze. My friends back East are my anchors. When I go back they ask me about family, friends, and everything BUT tech. They tell me how impressed they are but what I’ve done, and remind me that I need to slow down.

Chances are good you are also doing amazing things, and you too need to slow down. It’s the way of our world, and this sort of conversation is critical to have on a regular basis. It keep us from losing touch with the whole point of this — to live the life we want, doing what we love, with other passionate people. No entrepreneur should lose sight of that, because most brilliant companies are rooted in a sentence as simple as that.

#4. A person with your similar skill set at your point of learning.

It’s the buddy system friends! I think having regular coffee dates, or Skype chats with people that are in your similar phase of growth is an incredibly valuable relationship. I am super fortunate to have come across these amazing women — Kristy, Kate, and Ruth– and for years we have pushed each other. We have questioned each other’s job opportunities, moves, and decisions. We have been there when things fell through, and when our “big days” happened.

There is a confidence that comes with a camaraderie like that. As they get written up for successes, I am there to congratulate them and it helps me strive for more of my own. We pass on leads, ideas, and more. I can’t imagine taking on some of the challenges I have without their support. They just get it.

#3. A colleague you don’t particularly love working with.

You might think I’m crazy, but it’s true. Finding someone who you just don’t click with and then committing to meet enough times to push through it is huge. One of the biggest challenges that face any entrepreneur is justifying what you want to do and why it’s going to disrupt the status quo–whether it be to investors, future co-founders, team members, press, etc. You better get good at talking to just about anyone, and explaining your side. You better fine tune your ability to take feedback, and get good at turning it into positive results. There is no quicker way then to push forward with a relationship that isn’t particularly enjoyable or easy at first.

If you can get good at working with just about anyone, you are going to be so much better off in the chaos of startups. We are a crazy bunch and we are a passionate lot…which can be an interestingggg combination. 

#2. A person with the exact opposite skill set than yours.

This one is probably one of the more obvious ones. I can’t say this enough — seek out those that are most unlike yourself. For me its been coffees with product managers, and tech leads. I’ve met with COOs and have standing chats with our office manager. Do I know much about any of that? Not really. Do I know more now than I did before I met with them? Sure as heck I do. It’s enlightening to hear their challenges, and see where me or my team can help. It’s motivated me to take classes in coding and financials, and it’s humbling to see just how much you don’t know. It reminds me life-long learning is critical to success, and particularly to those that have bought into a career founded on innovation.

How can you possibly be set to recreate something if you aren’t constantly recreating yourself? Learning from those with opposite skills from you is a key piece in the constantly self-evolution required.

#1.  A friend who always knew you’d be an entrepreneur.

Yup. This sure might seem like a strange one to be on the list, but you should absolutely be meeting consistently with someone who knows you as “your entrepreneurial self.” They don’t know you any other way, so they are the most likely to feed your startup self soul. They are the ones to most likely say “you got this” and “this is what you do” — even when you are doubting it yourself. They can’t imagine you ever taking the safe option, or stepping down. They would never tell you it’s okay if something is half assed, and frankly they will high five the shit out of you for every one of your accomplishments.

Entrepreneurs are funny. We love to hate on ourselves. We never did good enough. We could have done more, we could have done it better, we could have… we should have… damn it. For the love of good startups people — find someone who can remind you just how great this moving and shaking you are doing is. Get coffee with them often, and cheers to the wins.

So there you have it. You might be thinking — that sure is a lot of chats and coffees and talking. Well yeah, it is. Learning, and stretching does not happen in a vacuum. For me at least  meeting with people who push me, and challenge me have been the one constant in the madness. I wonder sometimes if I would have ended up in this city, at this company, with these skills if it weren’t for the people around me.

I’ve chosen to play the part of sponge as long as I can. I don’t know when my next big leap will happen, but I’ve come to accept there will be another big leap…someday. I want to be ready for it. I am surrounded by brilliant, passionate people and that’s a gift. So go…email that person and ask them out for coffee. Ask them to mentor you, or just ask them a few questions. Start small and see where it takes you…you never know. You just never know.