Finding Mentors: Do you want to feel better or get better?

Wil Reynolds
7 min readJan 3, 2022


I read this passage in Thinking in Bets about creating a group that was built to make each other better at poker.

When one player brought up how unlucky they had gotten, another would nod in assent as a prelude to telling their own hard-luck story, which, in turn, would be nodded at and assented to by the group.

I saw Erik during a break in a tournament, and started moaning to him about my bad luck in losing a big hand…he laid out all the elements of a productive group charter. “I don’t want to hear it…if you have a question about a hand, you can ask me about strategy. I just don’t think there’s much purpose in a poker story if the point is about something you had no control over,,,the rules of being in a pod with him. He discouraged me from confirmatory or biased thought like “I got unlucky.” He encouraged me to find things I might have control over and how to improve decisions about those.

You need to constantly re-evaluate your circle as you grow. Do you wanna feel better or get better? You need to be honest with yourself about that, then ask yourself what is the right mix. Then evaluate the group of people you bring your work or life problems to. You might need to rebalance your advice portfolio.

The types of people around you are likely a mix of 4 types of people, lets assume you are in a “woe is me / this business stuff is tough” spiral.

Type 1: The cheerleader / comforter

When you talk about life being hard, this person tells you how successful you already are. Some days when you are really down on yourself you might need this person, but don’t get it twisted when you look back they never bring you new ways of thinking, their intent is to help you feel better. The things you’ll hear from a cheerleader will make you feel good but might also make you overconfident.

Outlook: The world is happening to you. It’s unfair, and we all hope it gets better. Person XYZ is the problem.


Type 2: The listener

Like the cheerleader, they want you to feel better and while they might not go with “you are crushing it” they listen a lot, they nod heads and maybe offer some advice but the advice is going to be couched in a soft delivery vs a “get your head out of your ass” approach. Keep in mind this person will make you feel great after a session. They might spend real time listening to you, but they likely haven’t contemplated that maybe you suck, and that is why you are in the position you are.

Outlook: You might just need to talk this through with someone, I’m here to listen and help you vent / get it off your chest. I’ll make you feel heard. They won’t hold you accountable


Type 3: The relationship tester

People who have advice hate giving it and spending time with people who don’t take it, so this advisor will give you a bit of their time as a test. They don’t take your calls same day, ever. It’s likely a week or more. This person is likely a deep thinker and when you bring them issues they will spend time thinking about helping you get out of that rut, that is a GREAT thing. They will give advice from a distance, but aren’t likely to dig in too deep (at least not at first).

This type of person is out there but you gotta be asking for feedback and telling them you actually want it and want to change. This person probably gets asked by 10 people a week for their time so they want to find the 1 or 2 worth pouring real time into vs even distribution for 10 people. They can also see when you spiraling / struggling, but they might see telling you that you are spiraling as “too much work” so they might give you things to read or a quick 15 minute meeting to chat it out…next week.

Outlook: I have a lot of people asking me for advice, I want to protect my time while helping so I’m giving advice to people for whom I feel it is helpful. If you show progress — I’ll give more time, and maybe move to the next type. I’m going to ask questions to see if you are taking our chats seriously and making moves, I’ll ask a couple times and hold you accountable.


Type 4: The trainer

A trainer shows up every day you show up, they are there with you during every rep, but they never lift your weights for you. They will spot you at best. They are here to kick your ass a bit, they can be a cheerleader some days and they can be a drill sergeant others. A great trainer will find a time when you are slacking and say “look if you don’t want to put in the work, don’t waste my time.” And they mean it.

This (to me) is the holy grail as we all need people around us in tough times who give it to us straight and they are going to put in the time to help us dig out of the rut (spotting us on that 10th rep). The “putting in the time part” and being willing to give hard advice are what make these people stand out.


When is the last time someone gave you really hard advice you didn’t want to hear? Like really stop and reflect? Then ask yourself when is the last time someone told you how great you are doing, how successful you are, etc? They will embody all the other 4. That is what makes them great they celebrate with you when you are crushing it and help you dig out when you are getting crushed.

I only have had 1 advisor like this in 20 years of running my biz. They will take your call at 8pm, 8am, EST, PST, GMT, never matters. FYI his book is one way for him to scale this approach (he’s also a type 3 for many others).

Steve has said things to me like:

  • “No one in your company understands where you are taking it, want me to go ask the first 15 people I see in your office today?”
  • “Send me your financial statements monthly so I can stay in rhythm with your business which means when you call me for help I’ll be in flow”
  • “I’ll manage your offsites this year (he did for 7 years) and be provocative with you/your leaders…”
  • “leader ABC over division 123 is sharp, are you incentivizing them appropriately, lets go over that next week ok?”
  • “When are you visiting that M&A Firm? Me: in 6 days, Him: OK I’ll take a red eye to be there by your side during those talks. Heck lets meet for breakfast across from their offices and gameplan before, I’ll just stay at the airport hotel, shower, gameplan and get back on the 1st flight out.”
  • “If you talk to me about something on glassdoor one more time! That site is an anonymous platform, it’s the bathroom wall at the truck stop and you can’t shake what anonymous people are writing about you, come on.”
  • “I see how you are talking about XYZ online, I don’t think that is productive to your goals.”

Outlook: Like Type 3, I have very little time, but I’m going to double down with you, that might mean 3–4 times a year I give you advice you might not want to hear but need to hear. If you fight me on it over and over I might learn something, but if you are just making excuses and not progressing, I’m slowly going to be out. I’ve already proved what I have to the world, if you don’t want my advice that’s cool.

Take a look and your “portfolio” keep in mind over a 20 year career I’d say my breakdown is

1000+ in type 1
100 in type 2,
10 in type 3,
Maybe 2 in type 4.

You likely need all of them, but be intentional about your mix based on your needs.

Too many #3’s and #4’s and you can feel hyper unsuccessful and that you are always messing things up (luckily #4’s will put in the work over years and years to help you), too many 1’s and 2’s and you feel better for a while, but after the chats your pipeline is still crap, your margins are still crap, your turnover is too high, and/or your bank account is too low. So you’ll be in the death cycle of talking to people who can’t help you even though they REALLY wish they could.



Wil Reynolds

Serial Underdog @seerinteractive doing SEO, Marketing, & Stuff, I am whatever you say I am.