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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.

Every week at Seer we ask people 1 question:
What are you most proud of accomplishing last week.

We implemented this for 3 reasons:

• As a company gets bigger it gets harder for us to stay on top of the great things people do.
• It gives everyone’s work equal opportunity to have their work seen.
• Culturally it serves as a reminder that we WANT you share your successes. IMHO: Too many people don’t share wins b/c they don’t want to look like they are bragging.

I’m a pretty positive guy, and throughout this pandemic and the roller coaster of emotions have been there but I’ve always been pretty positive throughout — never fully realizing that it was the support system around me that helped me deal with the pandemic with a good attitude, energy, etc. Wife, grandparents, nanny, work is 3 blocks away, amazing leadership team, calendar flexibility, etc. I always realize it to some extent because I focus on gratitude, but I found out just how much that support system has been getting me through when my kid got a positive test.

Last week I filled this out for what I accomplished to the team, I recognized man do I have a lot of privileges…

Team,

It’s what I didn’t accomplish. 🙂

Last week I was proud of the team we have assembled to help me run this business.
Had a COVID case hit my family and I was able to accomplish NOTHING, because so many people stepped up for me.

Last week I am thankful for my ability to gain perspective and look for the value in all situations.

My 6 YO got COVID, so I got to feel that worry that so many people have had throughout this pandemic.

Then because my wife and younger son were negative they left the house, leaving me to be solo with my COVID positive son, Rio. I recognized a lot of privilege I have. My nanny had to stay away too, so I was solo, no wife, no support system, no grandparents.

It caused me to reflect a lot of single parents (and heck even 2 parent households where both parents have busy jobs) are like this, and while I was only 6 days or so, I felt the drain. It was helpful to feel that and I hope make me a more empathetic leader.

Perspective #1: Working with kids, from home during a pandemic
I tried my best to be available for work, but I failed time and time again to be as available as I thought. I didn’t want my kid watching TV all day so found myself playing a little bit during the day — many nights working from 8pm-12am (or beyond) just to try to get people the answers they needed so they could do their jobs. This is tough and what a LOT of our teammates have gone through. When I played with my son , I found myself feeling guilty that I wasn’t getting people answers they could use, felt like I was always behind.

#2: This house is a MESS, but I can’t find time to clean it
From the time I founded Seer I knew working from home didn’t fit my work style. But being forced to for a week+ helped me feel what it felt like to not only not have time during the day to manage my kid and work, but also I had to SEE the mess my house was becoming. At work I can separate my spaces and I have always been appreciative of that, but having to see my house a mess several times a day, but not getting to cleaning it until the wee hours helped me gain more understanding of how seeing the mess of your house hour after hour and know you can’t get to it is DRAINING. You feel a bit like a failure like “how can I not get to these basic housekeeping tasks?”.

I did try to make my bed every morning, and largely did that as my “I am going to at least start this day off right” approach.

#3 Having an awesome nanny + private school is a major stress relief
Anyone who ever asked me how I’m doing — you always get real answers with me, and I’ve largely recognized that I’ve “been really good” almost every day b/c I have an amazing support system.

My kid was able to be in school almost the whole time during the pandemic and our nanny managed the school drop offs and even when school shut down for 2 weeks, she managed most of the zoom class work and balance that enabled me to be super present for you all, my teammates which helped us as a company get through. Last week if you aske me how I was doing, you would have heard me happy that my kid didn’t have symptoms, but I was BEAT the eff up after only 1 week.

#4 — Air conditioning is awesome
So I kept all our windows open to maximize ventilation and some days it felt like 104 degrees. Reminded me that a lot of people going through the same thing I am throughout my city don’t have AC, yet they gotta work, manage kids with covid, and all the other stuff too. Having those windows open all week, zapped my energy — I would sit around the house just sweating — by the time I got to put my kid down to start work, I was ZAPPED my shirt was sweat soaked and I realized all that sweating took even more energy outta me.

I’m grateful for the people we work with and for the experience as I think it will make me a better leader and a more empathetic human. So I took some good even out of my kid getting Covid, thankfully he is safe and sound now and my kids are back together, playing and by playing I mean…being annoying and fighting — I’ll take it. 🙂

“Business is my hobby” by Gary Vaynerchuk resonated with me 4 years ago when I first saw it.

I hustle. I’m unapologetic about it.

When I tell people how much joy I find in my work and so often the response is “well yeah now that you have a big successful company and people to help you run it, and you are financially independent, I bet it’s enjoyable.”

That is fair. So I dug deep and looked within and questioned myself — Am I only saying I love work and I love my job because I’m now at this point?

Here’s the secret — For every job I’ve had, paperboy to telemarketing to warehouse worker (3 years) to CEO, I tried to find joy in it or a game somewhere in there to turn the work into a way to compete, with someone or with myself.

I picked a few jobs I’ve had (I skipped 3 just to keep this article short) and how I turned them into games / challenges.

Age 12:

I had a paper route. This gave my mom an opportunity to teach me about money, customer service, etc. I wanted to get maximum tips and spend the least time doing it. So I learned how to “optimize” my route to get thing done fast but with integrity so I could get those big tips at Christmas. Also when it rained my mom never drove me around (for Sunday papers, the big heavy ones w/ all the inserts and coupons, she worked full time)…this is YOUR money she would say. Why should I have to work on my day off (sunday) so you can make money to spend on baseball cards? Noted mom & I hope to be this way with my kids, but it’s going to be hard.

(I will never forget the day she drove me b/c it snowed a foot on a sunday).

I loved connecting with my customers, I liked managing my books on who paid and who was past due, I enjoyed knowing that I could both optimize my route and maximize customer satisfaction at the same time, some how it gave me joy, I was 12 years old.

At age 13:

I was packing bloodborne pathogen kits in a warehouse in New Jersey, I found a way to turn it into a game, how many could I do in a day? Age 13, I wanted to be a high performer, better than the rest, and I think I did pretty well. I outlasted almost everyone else in that hot ass warehouse. This is the first time I realized that I got joy from lasting longer than others did, my best friend quit half way through. I finished.

This year I learned how to set up a “database” on my Packard Bell 386 to track my baseball cards, so I could manage their values and I played “games” where I sold them to people to maximize return.

At age 15:

I worked at an independent sneaker shop, I sold shoes to people, helped them try them on, I smelled feet ALL. DAMN. DAY.

I was working with adults for whom this was their livelihood, for me it was my high school spending money, how I bought hockey pads, cleats, and gas. But if you saw us working, you would have thought the opposite.

I loved working the closing shifts because every day for the owners to print out the daily sales by associate to see the “data” on how I did. Man those dot matrix printers were slow, I couldn’t wait to see that ink hit the sheet one line at a time watch my name come off and see how I did.

Most days I put a whooping on everyone. I wasn’t motivated by the money, was motivated to be a high performer, top “compete at the highest level” as Cory Henke would say, and I was only 15. I treated work like sports. You ain’t beating me, and when you do I’mma watch you, learn from you and add what you are doing to my style.

At age 19:

I worked in an amazon warehouse. Same thing, I found joy in speed, optimization, and quality. I was surrounded by people who complained… “this place sucks”, “it’s too hot”, “the food in the vending machines is stale”. I instead started challenging myself to speed up my times, optimize my route, and keep quality high. The same challenge I had 7 years earlier as a paper boy. I spent 2 years optimizing routes, figuring out ways to do things better.

When I say “I love my job” it’s because it fits what I like to do. It’s not about the “commercial success” Seer has had or financial independence … I loved the hustle, paperboy, to warehouse job, to telemarketing, to warehouse job, to Seer. Same shit.

Age 44 — The right work + the right people = motivation

Here are just 2 people who have been with me when we were single digit number of employees, I would be lying if I didn’t recognize that working with talented people is also tremendously important in me loving my job today, I get so much joy watching people @ Seer “win”. That I find that’s the difference in most of those jobs above it was on me to “win” — with Seer its different, the joy comes from helping others to win and I’m finding that is quite joyous 🙂

Today my motivation comes from both the work and the people I want to help win.

My motivation isn’t to get acquired or have an exit, it is to have a meaningful impact on the trajectory of my teammates lives and careers and in doing that I think we get to impact our industry and most importantly the lives of people in our community in a meaningful way, that just might continue to be “fun” for me.

I have the ability to trick my mind into “enjoying” any job / turn it into a game, which can help me perform at that high level, even if I am “only” packing books in a warehouse.

As Gary says in the video…some people get joy from watching game of thrones and that is awesome, no one judges for you for that. Just be open to the fact that for some people their “game of thrones” is business or a data problem (mine).

Managers, firing sucks. It does, we do it hoping it is the best end state for the company and the individual. A good manager wants to see someone win, but a good manager also knows when someone isn’t going to win at this time, in this company, that it is time to part ways.

8 years ago I wrote a post about loving the employees who leave, it all still holds true.

I had to share this email I got from someone I had to let go, 9 years ago.

I’m sharing this for every manager who will never get a message like this…most of us don’t. I’ve only gotten 1, in an 18 year career but I bet somewhere there are more of these that just haven’t been written. So keep your head up.

If you’ve ever been let go and in reflection it helped you to be on the path you are on now, consider dropping your own email to that person, it might help make them a better manager.

It took him 9 years to write this…

Subj: Thank you wil

Hey Wil,

This is an email I’ve written many many times. I’m not sure if you remember me but I worked at SEER, very briefly, around 2012? I think. I don’t even know anymore.

I just wanted to thank you for giving me that opportunity and teaching me the most valuable skills in my professional life.

You ended up firing me, in a frightening upset tone that left me absolutely crushed afterward. It took me almost ten years now to realize that was the best thing you could have ever done for me. SEO was not my passion. Development was. And you encouraged me to build cool shit and explore the unknown when I showed you Fusion Tables (RIP).

I am so very grateful for your time and to have met you. I’ve now worked my way up as a full stack developer working on [redacted]. And because of you , I ALWAYS keep detailed meeting notes and send them afterward. Every part of me hates it but I couldn’t ever stop.

So, in all sincerity, thank you Wil.

(Sorry I know you hate long emails)

This email is touching for so many reasons. I’m busy so I’m going to rip these quick and hit publish.

• It took him 9 years and many re-writes to send this, this was a great reminder that letting people go from your company can have LONG term effects on how people feel about themselves. Reaching back out can be scary / difficult.
• Getting to work in your company for some people is validation that they are good / good enough. The opposite is true for some people you have to let go, it’s even more devastating when it doesn’t work. I got this from someone we let got 2–3 years ago, it was a new perspective to me.
• Firings sometimes are just what people needed to do that soul searching and deep questioning, but we rarely hear that feedback, which for this person helped them to see that he is a super high performer when in a different role altogether (he’s working on satellite technology).
• Firings sometimes “nudge people” in a direction that they know is right but were unwilling to do. The better you get at those nudges, the sooner someone can go find where they can be successful, you owe it to them.