The 5 Types of Mentors – Kings of Conversion

The 5 Types of Mentors

Everyone says you need a mentor.

But I believe that’s a lie.

You don’t need a mentor.

You need 5.

Very specific types.

Each one fulfills different needs and plays a unique role in your growth.

Choose the wrong mentors (or don’t have enough of them) and you set yourself up for a lot of frustration, disappointment and soured relationships.

But if you know the types you need and choose each one carefully, you set yourself up for continuous, healthy growth for years to come.

I know because I’ve made the painful mistake of choosing bad mentors… or trying to get all my needs met from one person… which only blew up in my face.

I’ve also paid for mentor relationships that were… let’s just say not great.

But over the years, I slowly pieced together the types of relationships I needed to actually reach new levels as a writer, business owner and person (and remain friends with the mentors the process).

I’m nowhere near perfect. But I do think I have a unique perspective on this.

And I’m showing you the 5 different types of mentors you should have in your life. You’ll see the core traits to look for in each mentor type, the purpose they serve, how to interact with them, where to find them and how to use them to help you grow.

Type 1: The Alpha Observer

About: When they enter a room, they are the unspoken leaders. As their name suggests, they are the clear Alpha in the relationship.

Their power stems from a career rich with achievement and years of wisdom. Their experience also gives them the unique ability to spot potential flaws in logic, catch mistakes early and provide deeply insightful tips to grow.

Another core trait of The Alpha Observer is the recognition in their chosen field. They’re often high-ranking employees or founders.

This status gives them a quiet confidence and aura dripping of success.

Because they’ve achieved so much, they need very little from other people. This means money, fame and and gifts have very little influence on their choices.

Instead, what motivates Alpha Observers is the ability to contribute and have their advice followed through.

This is good news for anyone seeking an Alpha Observer as a mentor. Because they are more than willing to coach and can give you powerful direction for years and years.

But improper follow through, bad follow up and not respecting the power dynamics in the relationship will result in an abrupt, swift and possible even brutal ending to this type mentorship.

Their role in your growth: The Alpha Observer’s chief role is to direct without questioning. They have the experience, the power and the foresight in the relationship. So they can best help mentees when the mentees trust that the actions, beliefs and steps that The Alpha Observer has outlined will ultimately work without push back.

For example, an Alpha Observer might tell their mentee to double their rates on a project or completely rewrite a lede.

And you must do it no matter how uncomfortable it makes you.

I know because both of these things actually happened to me!

I was scared to try to charge more for a VSL, but I did it anyways because my Alpha Observer told me to. And it turned into the best decision of my life. That client ended up being one of my best and highest paying to this day. 

And once he told me to rewrite a lede I was really confident in.

I wanted to fight him on it but I made the edits anyways.

And the tweaks we made turned a probable flop into one of my most successful promotions to day.

The key in both of these situations was that I (the mentee) had to do these things even if though it was uncomfortable or disagreed.

I call it trusting in the wisdom of The Alpha.

When you completely let go, they can help you challenge deeply held beliefs, you take proven courses of action and you avoid making the same mistakes over and over again.

Interacting with them: The most important part your relationship with an Alpha Observer is how you interact with them.

They’re willing to tolerate a little push back from time to time. My Alpha even encourages rich discussion!

But (!) you must always remember who’s the Alpha and respect the power dynamic of the relationship.

If you get too fast and loose with your words or start treating them as an equal, Alpha Observers will feel disrespected and lose interest in the relationship.

Remember, they don’t need you. You need them.

Alpha Observers are also very successful at what they do. This means they are very busy. So they have little patience for wasted time and lack of conviction.

If they tell you to do something, do it fast. I like to try to do it within a day or an hour for simple things. And within a month for bigger projects.

But you can NEVER call them with silly questions. And definitely don’t ask to talk if you get stuck. You want to give the Alpha the impression that you are an effortless success machine.

So instead of questions, send them updates on your progress. I like to make a note on my calendar to send my Alpha an update at least 1x per quarter and only ask one deeply, penetrating question at a time. 

Where to find them: Alpha Observers are often easy to spot. They’re the most successful people in your company or top-ranking pros in your field. For me, my Alpha was the president of sales for a company I used to work for. He was the most successful salesperson in the company by lightyears so I knew I wanted to learn from him.

But your copywriting Alpha Observer can also be an editor or copy chief in your company. Or someone who’s copy you really respect and admire online. 

While spotting them is easy, getting the attention of them is very difficult. 

In my experience, the best ways to find them are in person at places you work. 

Or by trying to start the relationship digitally by emailing them a really targeted question.

And if they answer, act on their advice as fast as humanly possible.

Then, follow up letting them know what you did and the results you got.

This will put you on their radar. If you repeat that a few more times, you’ll establish an unofficial mentorship that can grow into much more over time.

I got the attention of the president of sales by being the fastest to execute on every idea he had… and just sending him updates when it was done.

Famous examples of this type of relationship: Warren Buffett and Charlie Munger. Mr. Miyagi and Daniel San. Ramit Sethi and Jay Abraham.

Type 2: The Indestructible Optimist

About:

You ever meet those people that always look for the bright side in every scenario? When it rains, they’re thankful the plants get water. If you get a flat tire, they’re happy to get to spend more time together when you change it on the side of the road.

They live in a world where there are no glasses half empty – only half full! (and actually if you look closer it might be MORE than half full! LOL).

These are the actions and beliefs that many in our next mentor group embody – The Indestructible Optimist.

As their name suggests, they have an undying, unending and unrelenting cheerfulness, hope and confidence that things will work out.

They often have an infectious energy that spreads to everyone in their circle.

When you’re around them, you know.

It’s common to feel better, lighter, and clearer-headed.

Their power stems from their ability to see the good in anything.

If a celebrity falls out of the limelight and onto dark times, these are the people ROOTING for them to make a comeback.

They’re the first ones who forgive after a fight.

And it’s common to find inspirational quotes littered around their houses. 

Problems seem to disappear when they appear.

Because in their eyes, problems do not exist…

Only blessings in disguise.

What motivates The Indestructible Optimist more than anything is giving their light, their joy, and their optimism to others. 

This is good news for anyone seeking an Indestructible Optimist as a mentor. Because they, more than any other type of mentor, are willing to pour their heart and soul into you for a lifetime.

But …

Too much negative energy, expecting them to engage in non-optimistic thinking, and expressing deep doubts in their logic will result in a nearly instant, painful and and possible even brutal ending to this type mentorship.

Their role in your growth: The Indestructible Optimist’s chief role is to empower you belief in yourself.

They are a shining white light of brightness, joy and possibilities. So they can best help mentees when the mentees are in need of inspiration and motivation.

They have the unique ability crush limiting beliefs and inspire you to take action. 

For example, an Indestructible Optimist might tell their mentee something like: “Sometimes when you’re in a dark place you think you’ve been buried, but you’ve actually been planted.'”

Or “You may not have gone where you intended to go, but I think you have ended up where you needed to be.”

Or “Keep your head up. You can’t see the moon if you’re only looking at the ground.”

While these sayings might seem trite, The Indestructible Optimist knows precisely when to deliver them, giving them power.

And if you trust in the phrases and look for the meaning behind what they say, they can be significant catalysts to grow.

I know because my Indestructible Optimist mentor has said all 3 to me!

When I was 12, I was diagnosed with a major heart issue.

Basically, my heart was too big for my chest. It pumped too much blood and if I wasn’t careful when I did normal stuff, I could faint.

Because the blood in my body wouldn’t get where it needed to go. Which meant I had to stop playing sports (even though baseball was EVERYTHING to me).

It was a really scary time. But my Indestructible Optimist mentor (my mom) told me, “Sweetie, I know this seems scary. But sometimes when you’re in a dark place you think you’ve been buried, but you’ve actually been planted.”

So I looked for the bright side and used the time I used to spend playing sports to practice things like math and… You guessed it writing. 

Truthfully, I might not be a writer today without that advice.

I call this believing in The Proverbs of The Optimist.

When you completely let go and truly believe, they can help you see new possibilities, believe in yourself and take actions even when you’re scared of where to go next.

Interacting with them: Engaging with an Indestructible Optimist is easy. 

Just don’t stomp out their light and you’ll be fine.

They don’t like gossip, doubt or negativity (save those things for other types of mentors).

So if you don’t agree with what they say and crave a dose of realism, just bite your tongue. You risk losing far more than you’ll gain by speaking those things around an Indestructible Optimist.

You should structure your relationship with them so that you see them at regular intervals.

Their positive bursts of energy will keep you motivated and inspired through even the darkest days.

But save your most in-depth meetings and calls with them for particularly devastating moments or setbacks. 

I keep my Indestructible Optimist mentor on speed dial for when I’m facing a really difficult problem or challenge. 

Where to find them: Indestructible Optimist are all around us.

They’re the friend who always makes you feel better after seeing them.

They’re the co-worker who always looks for ways to turn lemons into lemonade.

They’re the family member who believes in you no matter what.

For me, my Indestructible Optimist is my mom.

Yes! I consider my mom one of my mentors. She’ve very wise. 

She’s always believed in me and empowered me to tackle some of my biggest life goals … before I believed I could.

In my experience, the best ways to find this category of mentor is monitor your energy after leaving certain people.

Do you feel inspired and good? Or do they make you feel drained and bad?

We all need optimists in our lives for when we inevitably face setbacks.

Famous example of this type of relationship: Daymond John and his mom.

Type 3: The Honesty Broker

About:

Ready or not … you might need a stiff drink for today’s mentor type.

Because as their name suggests, they deal in the world of honesty. 

Their currency? Straight truths.

Where others are fine to tell a little “white lie” from time to time or whisper what they think you want to hear in your ear, this is a foreign concept to The Honesty Broker. 

They speak their mind and are unapologetic about it.

They’re not so worried about hurting feelings that they’re unwilling to be direct with you.

On first contact, this can give them an abrasive exterior, like steel mesh.

And some people are scared away by their blunt takes and complete disregard for avoiding conflict. 

But don’t let their tough exterior fool you.

Behind their honest takes is a deep desire to help others in a way that most won’t: By saying what others are afraid to say aloud.

So what they say is never meant to be mean. It’s always meant to be clear.

This makes them the first person their friends call when they have a problem they actually want a solution to.

Because when you bring an Honesty Broker a problem, they won’t give you any sugar-coating.

They will cut straight to the heart of the issue. 

Also like steel mesh, their frank, truthful, and candid feedback can help polish, remove rust and erode tarnish that would have stayed in place for years.

This is good news for anyone seeking an Honesty Broker as a mentor. Because they, more than any other type of mentor, can be a source of real, deep meaning feedback that’s needed to grow and improve.

If you want to do the best work of your life, you need an Honesty Broker in your life.

It’s for this reason they are often in leadership roles in companies or crucial partners in a business venture.

Because while intimidating, they are vital to truth-givers to almost every endeavor and deeply respected amongst their peers.

But …

Denying facts in their face, asking for coddling, and giving in too easily when they push for the truth will result in a nearly instant, painful and and possible even brutal ending to this type mentorship.

Their role in your growth: The Honesty Broker’s chief role is to tell you the truths others are afraid to say. 

They are a refreshing dose of realism in world of fake compliments and false praise. You can accuse them of being blunt but you can never say they weren’t real with you.

They can best help mentees when the mentees are open and willing to listen to feedback. 

They have the unique ability cut the crap, listen to problems and tell you exactly what you need to do to improve. 

For example, a mentee might come to an Honesty Broker with a problem about writing truly great copy. 

The mentee might say, “I’ve been practicing a lot! But still other people tell me my copy isn’t good! How do I know when my copy is good enough?”

Let’s pause and think about the typical answer someone might give.

Something like… “You’re doing great! Just keep practicing!”

While there is a time and place for that kind of feedback (see mentor type 2), there’s no chance in H-E 🏒🏒 that an Honesty Broker is doing that.

They’re going to say, “Let me see something you wrote!”

And proceed to go line by line through the mistakes they seen, one by one, unfiltered.

While this might seem extreme and really hurt at the time, this is the kind of honest truth that’s needed for growth.

And if you actually listen to what an Honesty Broker tells you, they will do you the one of the greatest favors you can get in life: Be told the truth… that other people won’t tell you. 

I call this embracing in The Bite of The Broker.

In my life, my business partner, Amanda, actually serves this function.

Every major decision I make goes through her. 

Why? Because I know she’ll be honest with me.

Sometimes it stings to hear the truth. Sometimes I get frustrated with myself for not thinking things through enough.

But I’m always appreciate of honest feedback. 

For example, back when I was working on the copywriting challenge (comparing Upwork and Cold Email), there was one point when I was getting really stressed with all the work I had to do!

I could feel myself making all sorts of justifications and practicing mental jiu jitsu. I even thought about quitting.

That’s when I knew I needed my Honesty Broker.

Amanda asked me to map out how I was structuring my day. I showed her.

10 minutes later she was like.

“Look, 90% of your problem is your own fault. Just stop doing [x] and [y] and you can calm down.”

After that, I was able to finish the challenge (with a lot less stress).

That’s the power of an Honesty Broker.

When you embrace their truths, they can help you get clarity, take decisive action and stop making the same mistakes over and over again.

Interacting with them: Engaging with an Honesty Broker is more challenging than other mentor types. 

But if don’t expect coddling and see their commentary as helpful NOT hateful,  you’ll be fine.

The big thing is that you should structure your relationship with them so that you are always prepared for truths.

Remember, at their core, they are deeply caring.

But if you go into a conversation thinking their intentions are off, you risk being deeply offended.

If you’re in need of a good dose of undying positivity or unwilling to confront other options, consider bringing your problem to a different mentor type. 

The Honesty Broker’s refreshing realism can serve as a powerful wake up call and even constant sounding board for problems (if you’re in need of true solutions and don’t just want to vent).

I (obviously) am in constant contact with my Honesty Broker mentor. 

And I recommend you bring them into your life often. Because they will help you do the very best work of your life.

Where to find them: Honesty Brokers are one of the most difficult to find mentor types.

Why?

Because the level of honesty they give is not immediately rewarded in society.

So the behavior is much more rare to find.

But..  you can still find them.

They’re the friend who will tell you “how it is” without fear of backlash.

They’re the co-worker who speaks their mind in meetings no matter who’s at the table.

They’re the family member who’s known for giving “tough love.”

In my experience, the best ways to find this category of mentor is watch how people handle problems.

Do they immediately jump to comforting phrases? Or do they first seek to address the core issues?

Famous example of this type of relationship: Ray Dalio and his associates at Bridgewater (they practice radical candor). Sheryl Sandberg and Mark Zuckerberg. 

Type 4: The Limitless Dreamer

About:

Have you ever been around those people that suck the fun out of everything?

You share an idea or talk about a project that you’re excited about and they immediately tell you the reasons why it won’t work?

Well those people are the EXACT opposite of today’s mentor type: The Limitless Dreamer.

As their name suggests, they live a world of limitless possibilities.

They are idea people through and through.

In fact, their notion of fun is grabbing a coffee or drink and spending hours discussing business ideas.

Where others are quick to disqualify and make excuses, those words aren’t even in a Dreamers’ vocabulary.

They are wired to think without restraints and live in a world where anything is possible.

To some, their never-ending stream of ideas can be a little annoying (especially when it’s not paired with action).

But when they work with a person who takes action, a Dreamer can be one of the most powerful types of mentors.

This is good news for anyone seeking a Limitless Dreamer as a mentor. Because they, more than any other type of mentor, can guide a young, hungry or ambitious person to success…

Like a rocket ship.

If you want to have leapfrog ideas and make true breakthroughs in your career, you need a Limitless Dreamer in your life.

It’s for this reason they are often the head of companies, managers of venture capital businesses and investors. 

They have a unique ability to see the future and are willing to take lots of bets on making their dreams a reality… even if they’re not always the one DOING it themselves.

But …

Showing a lack of creativity or being unwilling to follow through will result in a swift, sudden and melodramatic ending to this type mentorship.

Their role in your growth: The Limitless Dreamers’ chief role is to encourage creativity and push you to think bigger. 

They have powerful minds and are a potent source of ideas.

This often makes them great predictors of trends and impeccable brainstormers. 

They can best help mentees when the mentees execute on their ideas.

For example, a mentee might come to a Limitless Dreamer to discuss a problem with the conversion rate of a funnel. 

And rather than discussing specifics, the Limitless Dreamer might come up with a totally new approach to the entire campaign.

It’s up to the mentee to execute on this plan.

And it might not work.

But if it does, it could lead to explosive growth in sales.

This actually happened to me.

I brought a problem with a webinar funnel to my Limitless Dreamer mentor. 

They took one look at it, suggested I remove 4 steps of the process and cut the webinar down from 1hr to 15 minutes.

It was a bold move. 

And if you show this to a traditional thinker, they will give you feedback on the current webinar and flow.

But not a Limitless Dreamers.

They refuse to think linearly.

In this case, the idea increased the ROAS on the campaign from 1.2 to 5.6.

Which meant we went from barely profitable to scaling to the moon.

That’s the thing about Dreamers. They approach problems radically.

Sometimes their ideas won’t pay off.

But when they do, it can be so huge that more than makes up for the losses.

I call this The Jackpot of The Dreamer.

And that’s what makes them one of the most potent forces in your life.

Because when you actually listen to their ideas and one hits, it can pay off massively and lead to huge leaps in your career. 

Interacting with them: Engaging with a Limitless Dreamers is fun!

They love to talk ideas and discuss possibilities.

If you never fault them for NOT taking action on their own ideas, you’ll be fine.

Also remember, at their core, they do not live in a world with constraint.

So when it comes to money, resources, time, none are a factor in what they say.

So it can make some of their ideas completely unfeasible.

But if you go into a conversation open to new ideas and filter for what’s actually actionable, you can walk away with game changing lessons.

The Limitless Dreamer’s best trait is that they challenge traditional thinking and encourage you to consider a new perspective you might not ordinarily see.

I make a practice of reconnecting with my Limitless Dreamer mentor 2-3x per year.

When we hangout, I fully intend to spend at least half the time brainstorming and discussing things that we’ll never actually do. 

Then, once the ideas are flowing, I ask for feedback on one big pressing issue in my business or life. 

Then, I make sure to actually try their idea out.

No matter how radical it is. Actually especially when it’s radical.

I remember once my Limitless Dreamer mentor and asked how I could get promoted at my job.

I expected him to tell me to focus on a specific type of writing to improve. 

But he suggested I stop acting like I was just a copywriter altogether.

And instead to start sticking my nose in every aspect of the business.

From ads to customer service to the email program, he encouraged me to start attending their meetings and start finding ways that I could help them with copy and playbooks.

I learned A LOT by interacting with customer support.

And I discovered even more by hanging out with the traffic guys.

Suddenly, I started seeing the business in a whole new light and began bringing even bigger ideas to the table.

Overnight, I got promoted.

Not by focusing on writing, but by taking a look at the bigger picture of the business. This is the power of Dreamer. 

Where to find them: Limitless Dreamers are tougher to find. 

But most of us have at least one in our lives. 

They’re the friend who LOVES talking about big ideas and business plans.

They’re the co-worker who refuses to think small about a project.

They’re the person who’s always two steps ahead of the trend.

In my experience, the best ways to find this category of mentor is look for people who LOVE ideas and want to think big. 

Do they love to dream and empower you to do the same? Chances are, you’ve got a dreamer on your hands.

My Limitless Dreamer Mentor is a direct report from a former job who always encouraged me to think big. 

Famous example of this type of relationship: Steve Jobs (idea guy) and Woz (the executor). 

Type 5: The Idol Who Becomes A Rival

About: Why is it that athletes rarely break records during practice?

But records get broken left and right during the heat of competition.

Because competition brings out the best in their work. 

When we compete, we push ourselves harder, we stay sharper and we want to achieve more when we have a rival to go up against.

This is the role of our 5th and final mentor type: The Idol Who Becomes A Rival. 

As their name suggests, they are people who we first admire and then use as fuel for our own achievement. 

It’s common for people in this mentor type to be responsible in some way for success early in your career. 

They can be bosses who gave you a shot, mentors who you looked up to for years, or friends who work in a similar field.  

But overtime, as your skill improves, you aren’t the mentee anymore. 

You are an equal. 

A competitor. A rival, who deserves respect.

And that’s what makes Idols Who Become Rivals one of the most powerful types of mentors.

Because they, more than any other type of mentor, will push you to reach new milestones in your career.

It’s for this reason they are often former bosses, people who we grew up admiring, and friends who work in similar fields as us.

They are people who were instrumental to our start but inevitable competitors as time goes on.

As long as you never make things personal, this type of mentorship can be a friendly, fiery competition for years to come.

Their role in your growth: The Idol Who Becomes A Rival’s chief role is to keep you sharp and push you to achieve more than you thought possible.

Since they often work in the same field as you, it’s common for them to be competing for the same awards and go after the same achievements as you do. 

As long as you maintain respect and friendly levels of competition, it’s beneficial to both parties.

At times they will frustrate you and make you mad, but at the core of your relationship, the competition with them is key to growth.

They can best help mentees when the mentees never take things personally.

For example, a mentee might have needed their Idol’s feedback on their work for years. 

But eventually, the mentee will be capable of producing work of equal or better caliber on their own.

It’s rare that the Mentor will ever cede their position as the dominant force. So they will almost always think their ideas are better.

It’s wise to listen or take their feedback to make your copy even better. 

As long as it never gets personal or too contested about who is right, this can be fruitful for your growth.

This exact thing happened with my idol who became a rival.

For years, he saw every piece of copy I shipped and his notes were critical to my success.

But eventually I wrote a VSL, I knew was dang good.

I showed it to him and he had lots of notes. It made me really ANGRY!

But instead of taking it personally, I took a step back and tried to use the notes he shared to make my VSL even better. 

I used the feedback as FUEL to put out something even better.

To this day, it’s still the most successful promotion I’ve ever written.

Interacting with them: Engaging with an Idol Who Becomes a rival is tricky.  

Since they are responsible for so much of your success, they will never truly view you as an equal. 

Even when your skills are progressing rapidly (or even on par with theirs). 

You have to know this is the foundation of the relationship and never take things personally when they make you feel like what you do is not good enough. 

Instead, use it as fuel and fire to keep growing.

I make a practice of keeping in nearly constant contact with my Idol Who Became a Rival. 

I want them to see my work, know what they are doing and for them to keep me on my toes.

I remember one time my Idol Who Became A Rival made a comment about how little I was doing to promote my personal brand. 

And set a fire on me to work 10x harder to grow. 

I call this the Reboot of The Rival. They have the uncanny ability to reset your clarity and focus to achieve new milestones suddenly and rapidly.

Where to find them: Idols Who Become Rivals have been with us our whole lives.

They’re the boss who took a big shot on us and made us into the marketer we are.

They’re the people whose work we studied from a far.

They’re friends who work in the same industry as us and keep pushing us to grow.

In my experience, the best way to find this category of mentor is to follow your emotions of jealousy.

Who is someone who you really respect but makes you really jealous when they do something you wish you could also do?

My Idol Who Became A Rival Mentor is my first and longest standing copy chief.

Famous examples of this type of relationship: Kobe Bryant and Michael Jordan. Tony Robbins and Jim Rohn.

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