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The UnCollege Blog

13 Hacks for Getting and Keeping Great Mentors

Timothy Kenny is the author of "Accelerated Learning for Entrepreneurs" and blogs about accelerated learning at If you are interested in learning more about getting your first mentor, Timothy is giving UnCollegians free access to his $97 course "How to Get Your First Mentor." You can get a free invite code by sending him an email at: with "Free Mentor Class" in the subject line.

Most people have never had a real mentor in their entire lives. And it makes sense; you never take a class in school about how to find a mentor. A mentor is not just someone who gives you advice (that's an advisor), a mentor is someone who cares about you and wants to see you succeed.

Video Summary Pt. 1

In our culture we have this idealized picture of what a mentor should be: someone who can give you sage advice on any problem you face in any area of your life. But the truth is these types of mentors are the hardest to find and you can waste years of your life searching for that one magical person instead of deciding to pick different mentors for each area of your life. By having multiple mentors you avoid the mistake of overwhelming one mentor with all your needs and problems.

The Advantage of Younger Mentors

Another myth is that a mentor has to be someone who is much older than you and much more successful. I thought this too for the longest time, until I interviewed Brian Wong, CEO of Kiip (graduated college at 18, 10M + company) about his experience with mentors. He told me that he looks for mentors that are 6-12 months ahead of him in the development of their company. Often these entrepreneurs are only a few years older than him. Why?

Because a younger mentor who has done what you want to do so recently has more recent and up to date advice than a guy who is the CEO of a company and only works on high level strategic planning, hiring and management. Avoid the mistake of trying to get a "celebrity" mentor. Once you realize the value of having a younger, less sought after mentor, you will see that these kinds of mentors are both easier to find and easier to convince to be your mentor.

You have to realize going in that unless someone is very famous on the internet, or are extremely busy or over-contacted for some other reason, they probably don't have a single mentee and are probably interested in being a mentor to the right person. One of the greatest tasks for an expert or thought leader as they approach middle/old age is finding a single person that they can pass the torch onto.This is a BIG problem that MANY potential mentors face and its one that you are perfectly equipped to solve if you follow a few basic principles outlined below.

A Mentor Needs You Just as Much as You Need Them

Never make the mistake of thinking that you need a mentor more than they need you. A mentor who wants something from you is not someone you want as a mentor. Their reward for mentoring is intrinsic -- meaning they are getting just as much if not more out of it than you are because they enjoy the process of mentoring. Being a mentor is also an ego-stroke for some people, because it validates their worth as a teacher and someone to look up to as a role model.

Young entrepreneurs get a lot of false ideas about mentoring from "Startup Accelerator Land." These "mentors" are not real mentors. They are really advisors who in some rare cases become mentors. It's a mostly professional, not personal, relationship, and there is oftentimes some form of quid pro quo involved. A real mentor is someone who you choose and who chooses you because you are a good fit for each other. You need to really internalize that they are there to serve you and they have just as much to gain from the relationship by teaching as you do by learning.

So -- Why Would a Mentor be so Interested in YOU?

Because they see themselves in you, they want to live vicariously through you, they want to re-experience the energy of youth, they admire your courage and youthful enthusiasm, they see helping you as a way to improve the world, your success validates their knowledge and wisdom as an entrepreneur. In many ways the best mentor-mentee relationships resemble an adult father-son relationship in which there is a combination of respect and friendship. Great mentors know that all great mentees will eventually have much to teach them...and the relationship will evolve into a co-mentoring one where they learn as much as they teach.

Remember: a mentor who has already achieved the success you dream of still has something to prove: were they just lucky or can they duplicate their success in another person? An entrepreneur can only achieve the true height of success if they can pass the torch onto someone else who they can help make even more successful than they are themselves.

Your job is to be that right person by being an exceptional student who takes action on what they tell you to do. For most potential mentors, an ambitious, fearless UnCollegian like yourself is the perfect person to pass their torch onto and guide along the path of life. Be fearless in your quest to find and contact mentors and you will be surprised at how rich your life becomes.

Video Summary Pt. 2


1. Use Voxer to Stay in Touch with Busy Mentors

If you have a busy mentor they may only have time to talk to you once or twice a month. Use Voxer to keep in touch more often and avoid a lot of the awkwardness and planning that come with scheduled phone calls. If you plan to set up a personal board of advisors or mastermind, Voxer has group chats as well. It's a great way to do a mastermind without trying to get everyone to show up at one place and one time.

Why You Should Use It:

  • You have more time to structure your thoughts and think of questions
  • You can text or send pictures as well as send audio messages
  • All messages are recorded so you can go back and listen again later
  • Voxer has a "bunny button" that allows you to speed up the other person's message by up to 3x, so you can listen to a 9 minute message in half or a third of the time. People speak at 100 - 150 wpm but your brain can process audio up to 450 wpm.
  • Helps avoid the feeling of obligation associated with scheduled weekly or monthly calls
  • No stress from leading the conversation, dealing with awkward silences or starting/ending the chat.

2. Use Shared Google Docs and/or Spreadsheets to Keep Track of Your Mentor's Advice

A lot of people get intimidated by spreadsheets. You shouldn't be. Spreadsheets allow you to organize a ton of information in ways you can't with a normal Word document or shared Google Doc.

In fact, "Spreadsheet Fear" is a dead giveaway that you are an amateur entrepreneur because most people don't start using spreadsheets until their old paper or Word document system starts to fail them. Basically, you only need to be comfortable using spreadsheets if you are working on big things which require handling lots of information. Having spreadsheet fear is like having an AOL email address, if you have it, at least don't tell anyone.

Use this sheet, created just for UnCollegians, to get started.

Why You Should Use It:

  • You can keep track of months worth of advice and recommendations in one place
  • Keep track of advice or book recommendations that you won't be able to take action on for months
  • You'll have a standard format you can use to prepare for each call
  • Your mentor can add their comments to the sheet during the call
  • You can prioritize advice from months of conversations in a single place so you don't get overwhelmed
  • Take and organize notes from each conversation in one place

3. Use Nudgemail to Keep Tabs on All Your Mentors' Emails

Keeping track of what emails you need to respond to or remember to check can be a big pain. Nudgemail is a free service that makes it easy to keep up with your email threads with many different people.

Sending Emails:

If you add to the BCC field when sending your mentor an email, you will get an email from Nudgemail in 2 weeks reminding you to recheck the email. This is handy if you batch your emails on a certain day and want to get a reminder if someone doesn't respond to your email.

Receiving Emails:

If you get an email on your phone and can't handle it till later, forward the email to and you will get a reminder to respond to the email same time tomorrow. This is one advantage Nudgemail has over other email reminder services because only Nudgemail works inside your email app on your phone. Other services like Contactually require a separate app that you need to install on your phone.

Tip: If you want something even more simple, create two new labels in gmail: .ToReply and .To Followup. The period before the label is important because it will cause these 2 labels to show up at the top of your labels menu so you can use it easily on your phone and don't have to scroll through a bunch of other labels. Make it a habit to check on these labels on a certain day each week. My day for doing email checkup is Wednesday.

4. Use Contactually to Build and Maintain a Large Network of Advisors and Mentors

Contactually is a more feature rich version of Nudgemail that integrates with Gmail as a plugin for Firefox or Chrome and allows you to get reminders to contact people. It was designed for sales people who need to keep in touch with hundreds of people but you can use it to keep tabs on lots of people if you want to build a large network. If you have tons of contacts you can get daily reminders to catch up with people depending on what "bucket" you put that person in.

You have to manually put each of your contacts into a bucket (thought they make this fun by gamifying it, and then you can set how often you want to be reminded of people in each bucket (so you can get a reminder to contact advisors once every 2 months and mentors every 3 weeks). This tool costs $20 per month but is well worth it if you want to keep in touch with dozens or hundreds of people.

5. Get Free Learning Resources From your Mentor...Their Library is a Goldmine

Your mentor either owns or has access to very high value educational materials that you are probably completely unaware of. Some conferences or seminars allow a person to bring a guest for free or at a discount - you can be that guest. If your mentor is part of a mastermind you may be allowed to tag along.

Your mentor may also have bought high priced business courses worth hundreds or thousands of dollars that are just sitting on his bookshelf somewhere. Be proactive about asking if your mentor has good stuff they can send you and offer to pay for the postage. Your mentor may also have taken notes from a book, course or seminar that they have sitting on their hard drive that they could easily send you. Treat your mentor's library like the goldmine it is.

6. Learn to Lead a Conversation on the Phone

One of the drawbacks of texting and email is that our generation has gotten less and less skilled at the simple art of having a real time conversation. I have been surprised to talk to many successful businessmen in their 40's and 50's who are extremely awkward on the phone... so you should expect to lead the conversation with your mentor or advisor.

Here are a few tips that help your get comfortable fast.

1. Don't be afraid of a little silence - In some Asian cultures (like Japan) silence is the most respectful response after someone says something signals that the thought is important enough to stop and reflect on. Silence may also indicate that you should wrap up the call, or that you should have prepared more for the call or written down some questions.

2. Preparation is very underrated but extremely valuable - I was at dinner after a conference with a group of very successful entrepreneurs a few weeks ago and one of them was telling us about his experience spending a day with Dan Kennedy, a hugely successful business teacher and consultant (Tim Ferriss read and was inspired to be an entrepreneur by his book "How to Make Millions with Your Ideas"

Front Cover

which he read when he was still in high school) , who charges $20,000+ to spend a day with him and pick his brain. This entrepreneur told us that the process of preparing for the day of consulting was just as beneficial to him as the consulting itself.

Prepare for your conversations by writing out questions, going over the various aspects of your life and your business, and by going over your notes from your previous conversations. Use your shared spreadsheet to make this process a lot easier. And make sure to tell your mentor what you have taken action on from your previous conversation and what challenges your have run into.

3. Don’t be afraid to interrupt - Especially in the beginning of your relationship your mentor will not know how much or what you know. You can end up wasting their precious time by letting them go on and on about things you are already familiar with. Your mentor is helping you because they want to see you succeed, not so you can listen to their war stories or ramblings (though these are fun sometimes too).

If you feel like interrupting would be disrespectful, just bring it up in one of your first conversations, and say something like: "I noticed sometimes when I ask you about something and I know what you're talking about I feel weird about interrupting you. Is it OK to interrupt you if I already know what you're talking about?" In general people will be willing to accommodate most of your preferences in a relationship if you are upfront and proactive about setting expectations instead of waiting for misunderstandings and assumptions to boil over.

4. Don't feel obligated to talk - Just because you usually talk for 30 minutes doesn't mean you should drag it on past the 10 minute mark if you don't have anything to talk about. You can always send a follow up email or call again or Vox them. You also shouldn't feel bad about going over time if the conversation is going well; your mentor will let you know if they really need to go.

5. The Past-Present-Future Model - Conversations follow a basic pattern of two people first catching up on the past, then talking about present issues/problems, and then making future plans. If you ever feel lost in the conversation just thing about which stage you are in and either move to the next stage or switch the focus to them instead of yourself or vice versa.

7. Create a Monthly Review Newsletter

You only have so much time to keep in touch with all your advisors, mentors, friends, acquaintances and other business people you know. So how do you know who will be able to help you with all the different projects you are working on?

A few months ago I created a simple email with a description of my progress on my various projects and sent it out to my family, friends, advisors, mentors and some business acquaintances. It's a good habit to reflect on your progress each month, and sending it out as an email takes very little extra work.

Just recently one advisor I barely ever talk to out of the blue responded that he would be able to partner with me on a small side project I'm working on how to deconstruct how humor works that could end up making a lot of money. This would have never happened if I wasn't sending out my monthly newsletter.

Its also a great way to keep in touch with mentors or advisors that you don't have as much to talk about with anymore. And it keeps you accountable because you know everyone is going to see what progress you make each month.

Send the email to yourself and then put all the emails in the BCC field and send it out. If you want to get fancy (for advanced users only) you can do a mail merge so they don't know they are getting BCC'd.

8. Take More Action and Be More Aggressive

To put it bluntly: most of you are not going after what you want hard enough or aggressively enough. You are wasting time and finding ways to not take action. I remember a quote from Arnold Schwarzenegger, who said something along the lines of "if you have never done curls until you puked, you don't know the meaning of hard work." I only started going to the gym regularly last year, but I started to understand what he was talking about a few weeks ago when I biked so hard that I puked and kept going until I got back home.

My biggest inspiration from bicycling came years ago when I read an article about Jure Robic, a long distance bicyclist from Slovenia:

His five victories in the Race Across America, an approximately 3,000-mile transcontinental ride that has been held annually since 1982, are unequaled...

Unlike the Tour de France...there is no respite for riders until they give up or cross the finish line...The winner generally sleeps less than two hours out of 24 and finishes in less than nine days.

In 2005, Robic won the race and two weeks later won Le Tour Direct...a course derived from Tour de France routes that included 140,000 feet of climbing — almost the equivalent of starting at sea level and ascending Mt. Everest five times.

Robic became accustomed to both the physical and mental stress that pushing himself to extremes brought on... He was prone to hallucinations. More than once he leapt off his bicycle to do battle with threatening attackers who turned out to be mailboxes. Once he imagined he was being pursued by men with black beards on horseback — mujahedeen, he explained to his support team, who encouraged him to ride faster and keep ahead of them.

Very few things will impress your mentor more than taking tons of action and being aggressive about achieving your goals.

Remember: just because your mentor has connections and resources doesn't mean he is going to share them with you. You have to earn those introductions and special favors. Your mentor doesn't want your wasting his time or money or embarrassing him by introducing you to someone and then having you drop the ball -- because that will all end up tracing back to him and tarnishing his reputation.

On the other hand, if you are super passionate about your projects and going beyond your mentor's expectations, that will get him excited and even more interested in finding ways to help you achieve your goals faster.

9. Learn Your Mentor's Personal and Professional Network

A lot of success comes down to knowing the right people. And I have noticed in my conversations with my mentors over the years that many won't proactively volunteer information about themselves or their friends or business associates unless you ask. There are several reasons for this. Sometimes it is because the person is just a private person, but other times it is because they think you wouldn't care about their other relationships, or they don't see the relevance to your projects or they think it would be self indulgent or because your time together is limited.

So what should you do? First, whenever your mentor mentions a person, either by name or not, immediately ask for that persons full name. Take it down in your notes and look them up later. If you don't want to interrupt the flow of the conversation you can email them about it later or on your next call. Add them on Facebook and Linkedin and check out who they follow on Twitter. If they are on Angel List (a social network for VCs and startup founders to connect) check that out also.

If you haven't already, install Rapportive in your browser so when you get or send email to your mentor you can see all their social activity online.

Use MentionMapp, an awesome Twitter app to see who your mentor spends the most time talking to and retweeting on Twitter, in visual form.

10. You Probably Aren't Asking for Enough

My mentee's don't ask me for enough help. I am guilty of not asking for enough help as well. You have probably noticed something similar: most people don't raise their hand and ask for help in class when they need it. Most people don't speak up at conferences when they can ask a speaker a question.

People are embarrassed to ask for help. Don't be. You should be embarrassed if you are scared to ask for help.

How do you know if you are asking for enough help? You will only find the line by crossing it a few times. The same is true with anything in life. You can always apologize later and if they stop responding to your emails or calls that usually means you should switch up your approach. It may also be a sign that you are putting all your eggs in one basket with a single mentor and you should look to get more mentors so you can spread out your asking to multiple people.

11. How to Build Trust (The Bedrock of a Relationship)

A good, strong relationship with a mentor is going to come down to two things. Shared interests and shared experiences. Shared interests usually means they have an interest in you as well as the problems you are facing and the project you are working on. Shared experiences mean doing things together like having a meal together, playing golf or talking on the phone.

A great relationship with your mentor includes one final ingredient: Your mentor sees themselves in you in some way. My best mentors have been older guys who saw me as in some way a younger version of themselves.

Lots of people will tell you that you need to give value to your mentor and other BS. There is some truth to this - Ryan Holiday (insanely prodigious reader, author of "Trust Me, I'm Lying," Marketing Director at American Apparel and majorly successful college dropout) is a great example of someone who took on an apprenticeship role with a master (Tucker Max and Robert Greene) but the master apprentice relationship is really not the same animal as the mentor mentee relationship because of the time commitment involved.

The key difference is in the motivation of your mentor: is it intrinsic or extrinsic?

Intrinsic means they enjoy helping you in and of itself, extrinsic means they are helping you for some other external reward. If all your relationships involve extrinsic motivation only that means that you have a recipe for flaky relationships and fair weather friends.

To a certain extent you can accentuate the sides of yourself that most resemble your mentor. The best way to do this is to ask your mentor to tell you stories about their life -- growing up and their early business life and how their interests in their various hobbies and business ventures were developed. You can then relate these back to your own experiences and interests.

Building trust also involves sharing stories that make you feel vulnerable, and asking your mentor to do the same. Don't be afraid to ask really deep, personal, intimate questions but also be willing to go first and expose your flaws and insecurities. If you are with the right mentor they will immediately identify with what you are feeling and going through because they have already dealt with those challenges and this is one of the best ways to bond closer with your mentor.

A few years ago I created a one hour Radical Honesty film about all the deepest darkest secrets of my life and shared it with my family, my girlfriend and my closest friends and mentors. But the person it impacted most was my first mentor I ever had, Mr. Einstein (no relation to Albert). When we watched it with his wife on their 18" TV screen at his house it brought tears to his eyes and he told me afterwards it was the best thing I had ever created.

For the most part finding great mentors comes down to contacting enough (of the right) people that you eventually meet potential mentors who are the right match for you. Then all the other tactics and hacks for getting and keeping a mentor won't really be necessary because there will be so much natural chemistry.

12. Dumping (or "Transitioning") a Mentor

Generally burning bridges is not a good idea, especially if there is nothing to gain from it. Ending a relationship with a mentor can often mean being cut off from anyone else in your mentor's social circle. However there will be times, especially if you are growing quickly, when you may outgrow a mentor or find mentors who are more suited to your current challenges.

I started my first garden this spring, and one thing my gardening mentor taught me is that sometimes to nurture the growth of a young plant, you have to cut off the dead or dying limbs. If you don't, they will take away precious resources from the thriving parts of the plant and stunt it's growth.

One of my first mentors was a great aid in many of my early projects but he was not business minded and eventually his feedback started to chip away at my confidence in my early ventures. Each time our conversations ended I was filled with doubt about my future and it killed my confidence because I took his advice to seriously. I decided to continue our relationship with less frequent contact and to avoid telling him about my business ventures.

Most mentors will not go out of their way to contact you or knock down your will be the one contacting them and leading the relationship. One of the benefits of not having regularly scheduled calls or meetings is that you avoid setting the expectation (avoiding setting the wrong expectations and proactively setting the right ones is one of the most important keys in having great relationships) in your mentor's mind that you will be contacting them regularly.

Here are a few ways to do it:

1. Fade to black - contact your mentor less and less often, and talk for less time. If they contact you respond less quickly.

2. Flip the script - focus on your mentor instead of yourself. You may be aware of your mentor's problems and you can talk about those without talking about or asking for help with your own. This is a good way of hinting you no longer need (or want) their help.

3. Mention other actors - drop some hints that you have other mentors that are helping you and that you have already asked for their opinions.

4. Don't talk about personal stories - you can always transition your mentor into more of an advisor role if you don't want to continue with a personal relationship.

5. Be honest - get comfortable having uncomfortable conversations. You are going to have to have a lot of them if you want to be a successful entrepreneur. Tell your mentor how you feel and why you think a change is best for you...they will ultimately respect you more for it and you will grow from the experience.

13. The Real Mentor is Within

How can you tell the quality of your mentor, and how good of an influence they are on you?

One of the best signals is to see how much they encourage you to trust yourself and your own judgment. For you to ever be successful as an entrepreneur you have to learn to trust yourself so that you aren't constantly knocked around emotionally by what other people think of you or your idea. Why didn't Steve Jobs do any market research before creating the iPad? Because he trusted his inner mentor enough that he was on to something big.

Another cool way to get answers to difficult questions is to ask questions to your future self. Imagine you are 10 years older and do an interview with your current teenage or 20-something self. You will be surprised at what you have locked away in your mind if you just switch perspectives. You can also do this with a role model. Ask yourself: "What would Steve Jobs say?" "What would ____ do in this situation?"

The more you know about the person, the better your answers will be. You can create an imaginary cabinet of your favorite role models from all through history and "meet" with them every week or month as you do your weekly/monthly planning. As you allow yourself to momentarily "become" that person while planning, you will over time get better at solving problems because you will develop the ability to attack a problem from multiple different angles.

Bonus: Power Tools for Cold Contacting Potential Mentors and Advisors

Finding a person's email address can sometimes be a real pain. Fortunately, there are companies out there who's entire job involves cold contacting blog owners to write guest posts on their blog. The tools below are a collection of the most powerful tools for finding a person's email address online.

Side note: This is the best way to publicize your newly minted learning blog - contact people with blogs who have similar interests and ask to do a guest post.

1. Install Rapportive - This tool shows you all the social media profiles your potential mentor has. You can find something they tweeted or shared on Facebook and then mention that in your email.

2. Use the Email Permutator - This tool creates 20 different possible email addresses that you can then copy and paste into Gmail. Make sure you have Rapportive installed and then click on each email to check to see which one is their working address. Click here for a video of how to do this.

3. Search their Twitter -Search Snapbird, a free service that searches someone's twitter history, to see if they ever mentioned their email. Type in their username and "gmail" in the search box and see what comes up.

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4. Do a Reverse Who-is Lookup - Every website is required to have information including name, phone number, email and street address of the person who owns the website. You can find this information by plugging in their website address here.

5. Search Google - Try "Joe Smith" If you get too many results add "filetype:pdf" to the end. Sometime people will have their email address in a press release or other PDF document.

6. Create a Spreadsheet for organizing your contact information - This comes in handy as you meet more and more people. Use this sheet, based off the one I use to organize all my contacts.

7. Check out Dale's book - Hacking Your Education for more tips on how to contact people once you find their email.

Timothy Kenny is the author of "Accelerated Learning for Entrepreneurs" and blogs about accelerated learning at If you are interested in learning more about getting your first mentor, Timothy is giving UnCollegians free access to his $97 course "How to Get Your First Mentor." You can get a free invite code by sending him an email at: with "Free Mentor Class" in the subject line.