How to find and get the most out of an entrepreneurial mentor

I don't know where I'd be today without my entrepreneurial mentors. A lot of successful entrepreneurs will tell you the same thing.

Every 20-something entering the job market should have a mentor that can help her navigate the business world, but the bond between an entrepreneur and her mentor is unique. There aren't a lot of tougher mountains to climb than starting a company from scratch, and the emotional stress of a startup can be overwhelming. Being able to learn from somebody who's gone through the ups and downs is invaluable.

"Mentorship is a critical part of building an entrepreneurial community," says TechStars Chicago Managing Director (and one of my entrepreneurial mentors) Troy Henikoff. "Having successful entrepreneurs helping newer ones creates a sustainable culture were everyone participates and gives back."

I've written about this topic before, but I wanted to expand on the subject with some thoughts and advice on how to find and get the most out of an entrepreneurial mentor. Naturally, I turned to my mentors (Troy Henikoff and Redbox SVP Mark Achler), as well as a few friends, for some sagelike advice.

Here are the five lessons I recommend remembering:

1. Like any strong relationship, mentorship isn't forced

You can't force a relationship, whether it's love or business. It took me years to learn this lesson. While you may want something out of somebody new you meet (an investment, an introduction, advice, mentorship, and so on), coming out of the gate with that will only turn people off.

More importantly, you won't know whether somebody will be a great mentor for you until you've had time to get to know them and work with them. Mentorship is a lifetime relationship, so don't rush in.

2. Lawyers and accountants are surprisingly well connected

When it comes to finding a mentor, the first place you should be looking is your existing network. But when that fails, you should talk to your fellow entrepreneurs.

"One of the best ways to find a great mentor, if you haven't encountered and built these personal relationships up over time through your previous work history, is to talk to fellow entrepreneurs/CEOs and ask them who have they worked with and recommend," says Redbox SVP of New Business (and my longtime entrepreneurial mentor) Mark Achler.

CEOs and founders aren't the only people who are connected to potential mentors, though. Trades that cater to entrepreneurs -- lawyers, accountants, advisors, and the like -- are also great resources.

"I have also found that attorneys and accountants who specialize in the startup world often already have these relationships and can provide the right access and recommendations to the appropriate mentors," Achler adds.

3. Keep your mentors in the loop

While mentors are there to help you when you're dealing with a crisis, this should not be the only time you reach out to them.

"Keep your mentors and advisers updated with regular e-mails monthly on your progress," says Henikoff. "Then when you need their advice, you don't have to waste time updating them on the basics, but keep them focused on the issue at hand."

Just like the investor update (which every entrepreneur should be sending to their investors quarterly), the mentor update keeps the lines of communications fresh.

4. Open up!

In Silicon Valley, there is a tendency for entrepreneurs (and VCs) to say that "Everything is awesome!" when asked about how their company is doing. Entrepreneurs don't want to show any weakness publicly, lest it hurt their chances for a Series A.

These barriers must come down when it comes to your mentor, though. If you can't tell your mentor exactly what's happening, both the good and bad, then you aren't getting the most out of your mentor. You're just going through the motions and doing a disservice to your company and your team.

"The right mentor is a father confessor," Achler argues, "allowing the entrepreneur to let down their walls and share the emotions -- both high and low. The right mentor is an invaluable sounding board of advice."

Achler also says that the right mentor is a trusted friend, "who will tell you both the good (and let's face it everyone needs a pat on the back every once in a while) as well as give you the honest swift kick in the rear end when appropriate."

5. Take your mentor's advice to heart

The mentor-mentee relationship is built not just on trust and friendship, but on learning. One must be open to hard lessons and be humble enough to recognize the gaps in his or her knowledge.

"The biggest mentor I've had has been [Y Combinator founder] Paul Graham," says Justin.tv and Exec founder Justin Kan. "His number one piece of advice was simply 'make something people want.' -- which is pretty good advice, because if you don't make something people want, you have no product, and no sales."

I'd say that Kan has done a good job following his mentor's advice. And while not everything a mentor advises you to do will be the right course of action, more often than not they are right and you are wrong. So go into the relationship willing to learn and humbled by the fact that you still have a lot more to learn.