The Top 5 Mentors Every Entrepreneur Should Have

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.

two coffee cups

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.

  • Ryan McLaughlin

    Yes. #2. I’m going to guess many people reading this post are marketers. For us, I think the most powerful group to connect with are a few awesome developers. In my experience most devs are working on side projects but don’t know how to get the word out. When I’ve offered to help for free, they are almost always willing (and proud) to show you how it works and how they built it. Invaluable IMO.

  • Doc Sheldon

    Great stuff, Joanna. I think #3 is especially productive – perhaps the most important of all, because it makes us justify our positions. If left to our own devices, we can get caught up in doing something because we WANT to, rather than because we SHOULD. It’s always good to have someone of an opposite mindset to keep you grounded, as well as to help you learn to get long with anyone.

    One thing you didn’t touch on in this post is the flip-side… mentoring someone else. You might be surprised to learn who the people are that already view you as a mentor. Just because you admit you’re still learning doesn’t mean you should short-change yourself on what you’ve already learned. We can’t pay back those that have mentored us, but we can certainly pay it forward. ;)

  • alanbleiweiss

    Joanna, this is an excellent article on mentorship.  It’s traditional to think of mentors as someone who has achieved the goals you want to achieve.  Yet your five are all critical to anyone’s ability to succeed going from just “potential” into “reality” while simultaneously allowing the journey to be absolutely more stable, less stressful, and much much more enjoyable.  Which means you’re infinitely more likely to get where you’re going on that journey. 

    I’m definitely going to refer this to people I mentor in business. 

  • Joanna Lord

    You are so right. Not too long ago when I wanted to find a mentor I was looking for a CMO, or a female co-founder, or something like that. I wanted to find someone I could emulate, and over years I’ve realized there is a lot to learn outside the path you are most likely to take. 

    Really appreciate you passing this on, it would be great to what other “types” of mentors people have found useful. Maybe newbs in the industry to keep a fresh perspective? Maybe people in different industries in similar positions? Lots of good stuff out there.

  • Joanna Lord

    See what I mean about selling ourselves short?! ha. I have made it a 2013 professional goal to seek out mentoring opportunities. I think that because I have so much left to learn, I don’t have much to give back yet. I think you are right though–there is always something to offer up…at every stage of growth :)

  • Mackenzie Fogelson

    Love, love, love the discussions about entrepreneurship. This is a really powerful one for me as I didn’t know shit about being an entrepreneur until I had mentors. I’ve learned everything there is to know about the ride from so many great people who’ve been there, or are doing that, and that really helps. Because you know you’d give up without ‘em.

    I’m going to marinate on your thoughts about getting a mentor who is a colleague that you don’t particularly care to work with. I can see how their perspective would be valuable and probably also open your eyes up to things unseen.

    Thanks for the thoughts and ideas :)

  • alanbleiweiss

     something else this speaks to is the concept that we can’t / shouldn’t attempt to rely on just one or two people – whether it’s purely from a business perspective or in life in general.  The more people we have in our inner circle, or look to for unique perspective, the better in that regard.  Of course we can’t /shouldn’t attempt to have too big a circle, yet if there’s a core group spread across a variety of unique values they contribute, it leads to a much stronger foundation there for us when we need it. 

    And too, it’s as much about the fact that when we initially “think” any one of them needs to be the person we reach out to, they could very well be busy with their own life in that moment.  So whoever the individuals are, and whatever they uniquely bring to the equation, your article speaks as much about the value of a diverse group…

  • Dev Basu

    Great post Joanna. I’d add “a person who isn’t part of the echo-chamber”. This could be a friend but interestingly enough, I’ve found that parents provide sage advice too. Often, they are able to simply a complex situation down the bare essentials and make you see things in a different light. 

  • mattcoffy

    Great stuff.  I need to build out my network of mentors ASAP.  I think the tough part is wading through the  process of who to select.

  • Jess Hill

    Good stuff, Joanna!

    This might be implied, but I like having one mentor who is smarter than me (at least I think they are!). This person definitely fits one or more of the profiles you described above too. It’s always humbling talking to someone who flat out impresses you.

  • Sonia Anand

    Great post Joanna !!!! A very well thought note. I must say i am very fortunate to work with Synechron, founded by 3 friends and has reached great heights. Being naive to this world, I must say they must have had some  of the mentors mentioned above. Its always great reading your articles Joanna.


  • Tim Cook

    This is some great perspective Joanna. I never would have thought to include #3 but it does make sense. We should never be so arrogant as to think we can’t learn something from smart people we don’t easily get along with. After all what we learn might not have so much to do with what they say but rather how they say it and how we listen.

    I would also like to add that having a spiritual mentor is really important. It gets back to your #5 and having someone to ancor you. I have tried to have spiritual advisor and it has helped remind me that there is more to life then business.