If you’re not technologically savvy, then calling the IT department can feel like your worst nightmare. Ben Brennan, author of Badass IT Support, believes you can transform your IT team into rock stars who everyone at the company loves.

Ben (@why) has consulted for the top tech firms in the US including Box, Twitter, Yahoo, Jawbone and AOL. By the end of this episode, you’ll learn the simple shifts you can make to revolutionize your IT department.

Note: In case you’re listening with little ones, know that in this conversation with badass Ben Brennan, we’ll use explicit language.

Ben Brennan: I did a few things before IT. I was a psychotherapist, I didn’t mention that I was a janitor in Germany, I did outdoor education at Austin, I was an unpublished writer and I was unsigned singer, traveling through Guatemala for a year. I did a bunch of low paying things that I was mediocre at, that sound cool. But when you’re poor, they’re not as cool as they sound for sure.

When I moved to San Francisco, I was dating this creative executive who was making high six figures, I was living in a co op and making like $40 a month. I was so f’ing poor, I could not tell you.

You eat like butter and noodles and then you run out of butter and you’re just eating noodles and salt, you know? That kind of poor. Not super healthy, as you can imagine.

At that point, my friend who is this amazing guy that I used to hang out with in high school, he was like, “I never thought about this, why don’t you just get into IT?”

I tried to google IT to see what IT was, and IT is a surprisingly hard word to google because it’s IT.

Even googling IT did not—and this is a real story—it did not help. What is it? Information technology. I’m like, okay, that helps. I change my search terms. I was getting the results of every single website in the world that has the word “it” in it.

“Maybe Google has improved their algorithm, but I will tell you, Googling “it” 10 years ago was not very fruitful.”

He’s like, “It’s information technology.”

“What is that?”

“Just fucking come.”

Fake It Til You Make It

So he was working out of this amazing place called Pivotal Labs. Let’s just say he embellished my credentials a bit and got me a contracting gig.

I come on and I get this first job in IT, and it was amazing. 25 bucks an hour, catered breakfast and lunch, right on Market Street in San Francisco. I was blown away, I could not believe it. I made more in a day than I did pretty much the whole month after taxes, right?

“The problem was, I also had to fix computers, which I didn’t know how to do.”

I went back to Google this time, not trying to Google IT, but learning problems. Basically I was like, “Okay, this is my ticket, I have failed at like 19 things in my life, I’m 30.”

It’s a long way to the top if you want to rock and roll.

My plan was, I’m like, I’m not losing this job, this is fucking great. My life as a level one help desk guy is a dream come true.

I just basically ran around and ask people what was broken, wrote it down, you know, five or 6 PM, went home and from 6 PM to midnight, just Googled everything, learned how to fix it and came back that morning was like, “Hey, I fixed your shit, here you go.”

And then I went through for seven hours and got like 10 more problems and went home, Googled it for six hours, learned how to fix it.

It was funny because it was kind of like, working so hard on cheating for a test that you accidentally learned the material. It was hilarious.

Before I was done, I still thought it was a hack. My friend was like, “Dude, you’re like really good at your job now.” Like what?

“Total imposter syndrome.”

But he was like, “No dude, I think somehow you actually became an IT guy, fucking great.”

I think that was really what got me into IT. I’m making really good money and I’m doing really well. To this day, every single morning, no bullshit, I wake up and do a gratitude meditation, and almost like four to five times a week, my job and my career is one of them because I didn’t earn it.

I had zero plan.

My number one plan at that time was writing poetry on Fisherman’s Wharf for like $10 a person. Investing in a typewriter and doing that.

Moving Up in IT

Charlie Hoehn: Are you an anomaly, are you an exception or there are others who have kind of landed themselves in that role and they’re like, “I’m going to learn on the fly”?

Ben Brennan: I think I’m a more common story than I ever thought. At the time, I felt like totally an anomaly, but it’ s not a special story at all.

The beauty of it is, in IT support particularly, you don’t need a degree, you don’t need experience, you really just need to know how to troubleshoot. These days, what are you troubleshooting?You’re troubleshooting consumer electronics, iPhones and MacBooks.

“You’re doing stuff that your little cousin could do.”

If you have social intelligence, I’ve seen outsiders come up, get a foot in the door in IT like companies like Twitter or Box or Yahoo and go on to make a lot of money doing IT or other things.

In general, I’d say your starting IT salary is around 50k. Which for me at the time was amazing but you know, I’m not in the millennial whatever. But really quickly, you can get up to a hundred.

The cool thing about IT is the bar is so low. IT sucks ass so much at companies. If you have social intelligence and like half a brain, you can move up the charts quick.

Boring System, Boring Reputation

Charlie Hoehn: Why does it suck? Would you say the majority of them are just not socially adept at all and so they kind of rub people the wrong way?

Ben Brennan: I think that’s true in some of the cases. To be honest, a lot of them are really well meaning and smart people who you go out and have a beer with them and they’re really awesome.

“But they’re not really motivated to be cool.”

I mean, granted like some of these guys are the old school version of you know, “I’ve never talked to a girl before in person.” But these days, it’s kind of cool to be a nerd. Steve Jobs is like the most recent, like a Greek god that we all worship.

Anyways, it’s really the system too, right? People aren’t really motivated to be their selves at work. It is a hard job.

I didn’t realize this until I started consulting, because I worked at like fun startups where I got to build the team from scratch. So I just hired my artist friends and we just ran IT. When I had the consult and work for like bigger, old school IT wards, it sucked man.

“The whole system was geared towards who can crunch the most tickets.”

They had all these metrics, conferences and books and certifications. They’re all pointless. I came in with zero experience and I’m already better than you in one year. That shows you that you have a problem.

To answer your question, yeah, there are the people that are like, we call them neck beards. They aren’t really good at talking to people. But frankly, a lot of people in IT are awesome, they just aren’t – their job sucks so much that it’s annoying and you can’t help them from being grumpy.

Ben Brennan’s Superpower

Charlie Hoehn: How confident were you going into that, that you could earn some money doing poetry? Were you pretty comfortable doing poetry at that time?

Ben Brennan: Yeah, right before that, I had been a traveling musician for a year in a country where they don’t even speak English. Sometimes it would be an awesome gig, but very often it would be a shit gig that people haven’t even showed up yet but you still have to play. So I just made shit up.

I got really good at freestyling and just making things up on the fly. One of my super powers has been able to freestyle lyrics.

I was pretty confident—I could have been at or slightly below the poverty level with my poetry.

Charlie Hoehn: It truly is a super power. Nothing blows people’s minds faster than making up a good song on the spot.

Ben Brennan: When I worked at Twitter, we had this thing called Twitter’s Got Talent. It’s just like a talent show for the employees. That was my talent. I said that I could solve any problem in 30 seconds through the majesty of song. It was a big hit.

People would just say, “I’ve got a problem…” and then I would set up there with my guitar and did a little cute song. It’s fun.

Learning from Badass IT Support

Charlie Hoehn: What do you think is the main idea that you really want people to take away from this book?

Ben Brennan: Really, I hope that it’s entertaining and fun for anyone to read. That’s why we kind of put a leather clad biker on the front cover and called it Badass IT Support.

We wanted to try to convey that this is not your typical IT manual.

But really, my target focus was CIOs and IT executives. Not because they’re hot shit but because I think if I can change their minds and really show them what IT support can be, it can roll downhill and really affect the whole organization and make everyone’s jobs easier and make everyone have more fun at work.

IT can be really fucking awesome, right? In IT, you have the ability to do amazing things.

IT has a rough reputation for good reason. If you’ve never worked in corporate America, ask a roommate or ask someone in your spin class what IT is like. The response will range from they suck to I didn’t even know we had an IT department.

It’s just a necessary evil. For CIOs, a lot of times it’s a necessary evil too. They’re worried about fending off the Russians and keeping cyber attacks from happening and DDOS attacks happening.

“CIO’s are worried about a lot of big shit.”

The last thing that they really care about is the quality of their help desk or how friendly their IT support is.

But that said, all they hear about in these executive meetings is how the CEO’s assistant in or somebody else’s executive assistant was treated poorly or someone was rude to their marketing leader or something, right?

It’s the most customer-facing part of IT but the least important in a lot of ways. Basically fixing this problem makes it awesome, and the way we fix it is just to be cool, right?

I spent years in the service industry where I worked for tips. How do you please a customer? You just be cool about it. Treat everyone nice, have fun. I learned that from being in a band too, the audience had more fun when we had fun, right?

In IT, we just put up art on the walls, we crank up some cool music, and we listen to our customers.

Ultimately, what the book does is it teaches you ways to listen to your customers and teaches you how have real, actionable data that turns your customers into the judge of your success versus you.

The Industry is Stale

Charlie Hoehn: Why don’t IT people do this now?

Ben Brennan: We’ve gotten a few companies to do it, but in general, there’s such a history of not doing this, and there’ a system setup where they don’t have a lot of power to make changes. That’s another reason I’m angling for the CIOs. IT doesn’t have a lot of respect in the companies. It really doesn’t.

It’s from years of frankly, not being good at our jobs.

We talked about Steve Jobs being the, whatever, the IT Jesus or the tech Jesus or whatever. For IT support guys, they have a bible, and it’s called ITIL. That stands for Information Technology Infrastructure Library, which was originally going to be the title of my book.

“The whole industry, no shit, is focused around this, and it’s super boring.”

It’s process driven. It’s like a whole religion with all these dogmas about how you crunch tickets and how you handle things, and it barely mentions the customer experience. It’s just like – here’s how you do it.

And everyone is just in love with ITIL. I was like, that’s fascinating because I think it sucks.

I wasn’t alone. I remember talking with some guys at Square and they showed me when they were small it said must be allergic to ITIL for their IT managers.

I’m not crazy, this is stupid. On Wikipedia, it was invented in like the ‘80s by the British government—possibly the most uptight organization of all time, and this is what people run IT with.

“Nobody really cared enough to change it.”

The reason me and my friends did so well in IT was because we had failed at other areas in life. We came into IT and we’re like, dude, we can make this fucking awesome.

It’s like walking into a boring party and we’re like, “My god dude, we’re going to about to make this shit blow up. This shit is going to blow up, this is so easy.”

The bar was so low that once we started doing awesome shit, word spread and then we have jobs for life.

Foundations of the Vision

Charlie Hoehn: You talk about in the book, you have to start with defining a vision for what badass IT support looks like, is this different from company to company?

Ben Brennan: It can be in a sense, but one thing I share in the book is that everyone has mission statements and core values. If you have this as your one mantra, you will succeed. This is what we do at Yahoo, this is what several other companies that I found works too:

“Badass customer experience is always priority number one.”

Drill that into your employees and into your leadership, and to your company too. A badass customer experience is always priority number one. It influences all your decisions.

If you really get on board with that and everyone’s on board with that, there are no arguments. You know, should we do this thing that’s awesome for us or do these thing that’s awesome for our customers?

Well, a badass customer experience is priority number one, so let’s take care of them first and worry about us later.

Becoming Badass IT

Charlie Hoehn: Can you tell me a story about a badass customer experience?

Ben Brennan: There’s so many of them, this is why I’m still in IT. Because as unsexy as a job as it can be, when you’re doing it right, it’s so fun.

I’ll tell you a couple, this is my favorite thing to talk about.

One of my favorite’s at Jawbone. I worked at Jawbone, it was my second job—so after I did the job where I kind of faked it till I made it and cheated so much that I learned how to be an IT guy.

I go to jaw bone which is a consumer electronics company, they made like the jam box, those Bluetooth earbuds, they made the UP. This is back when they were just a Bluetooth earpiece company. They’re tiny, like 45 people, nothing, you know?

Right after I landed the job, all of a sudden they blew up. They got a shit ton of sequoia venture capital, started building the UP and Jawbone and we were in hyper growth.

“The company quintupled in a year or two.”

My first job was a startup in hyper growth with a bunch of EC money. I was the only guy. They only needed one at first, so I got to hire a bunch of people under me, and that was also my first IT management gig.

Anyways, my first job was to move everyone from Windows to Mac, which was great for me because I hated Windows anyways. We go through and we make a big deal about it, we image the machines, which just means that we get it ready to use for on a corporate network. We put them back in the packaging, we take big red bows, we put them on everyone’s desk, you know?

We’re having a blast. Our team at Jawbone was so fun.

But what happened shortly thereafter was cause for concern. Apple came out with this computer that you might remember called the MacBook Air. This was a sexy, shiny, thinner than ever computer that was a total piece of garbage. One USB port, I think like maximum 64 gigs of storage maybe, no backlit keyboard. It was confusing, it was hard to figure out how to turn it on and if you were an executive in Silicon Valley, you had to have one yesterday.

Showing up at a meeting without a MacBook Air that week would be like showing up with like a cellphone holster.

Get Him the Air

Charlie Hoehn: It was like a status symbol?

Ben Brennan: It would be like driving up to the parking lot and not be in a Tesla, if you didn’t have a MacBook Air. That’s how important it was, right? Anyways, obviously, if you’re badass IT support, you know your executives have to have one.

We were friends with the Apple business team, and we had two CEOs, which was awesome but in this case, it was annoying. We had our founder in San Francisco and we had a cofounder who was in the UK.

We get the email, hey, obviously, we need MacBook Airs yesterday, please let them know when they’ve arrived and ready to go. We call our guys, we get them delivered, and then we reached out to Alex who is in the UK, we’re like, “Man, when do you need that?”

He’s like, “Actually, I’m leaving for Asia tomorrow, so I guess you guys probably can’t get it but it would be really cool if you did.”

We were like, “Shit,” right? “What do we do?” We call our girlfriends, cancelled dinner, I go and I start imaging and configuring Alex’s MacBook Air before he went on this big trip. And then my buddy gets on the phone and on the internet and just called all of his contacts in courier services to figure something out.

He came into the room and I’m like, typing furiously trying to get all these email loaded and shit like that and figure out how to get all his email on a 64 gig hard drive with the shittiest –it wasn’t fast either, the MacBook Air.

Anyways, I’m getting all that stuff in and he comes in and he’s like, “There is a service that will pickup a package, drive it on to the tarmac in SFO and put it on the last FedEx plane leaving.”

I’m like, “No way, how much is it?” He’s like, “It’s fucking expensive.” And I’m like, “So we’re going to do it?” He’s like, “Yeah, we’re going to do it.”

So, this was amazing. Now I’m working faster, he calls it up, “Can you have it ready in 20 minutes?” And I’m like, “I guess so.” I’m working like crazy. 18 minutes later, ping, the elevator door opens, you know, this greasy pony tail guy with a biker motorcycle helmet comes in, picks up the thing, we hand it to him, we’re like, “You’re going to make it?” He’s like, “Yeah, no problem.”

“If you’ve ever been on the 110 and seen like the motorcycles splitting lanes, that’s the only way that this guy did it.”

It would be an unbelievable story how fast he got to SFO unless you’ve been on that road and you’ve seen those guys fly by everyone.

I swear, it was like less than – it was like 18 minutes later, both of our phone’s like, because of course we had notifications, “Your package is en route London,” and we’re like, “No way.” You have to beat the time zones there too, right?

I’m sorry, this is a long story but it was so fun.

Your Customers Decide

Charlie Hoehn: No, don’t apologize, by the way, what you’re describing is truly badass IT.

Ben Brennan: I thought so, we just did it because it was dope, we just needed to do it, right? We send it, it’s across time zones—reminding you, we’re in California and that shit has to go east. Somehow it gets there, and then I get a number. The +44 on my caller ID. I pick it up the next day, you know, probably hungover as shit.

It’s Alex. “Dude, I don’t know how you guys did this but fucking awesome, thank you. You guys are” – he probably said badass or awesome or whatever. We’ll say he said, “You guys are fucking badass.”

It really stuck with me, because first of all, it’s awesome for your second job to get props from the founder. Second of all, it was awesome.

I still can’t believe that service even exists. What I try to tell people now, I always remember that story.

“You’re not badass when you say you are, you’re badass when your customers say you are.”

ACDC’s not badass because they said, listen to this badass song. They played that riff and everyone else said it was badass. That’s I think one of the core messages in the book.

You don’t get to decide when you’re awesome.

Every IT company in the world has “world class” somewhere in their offering, right? Providing, world class support. That word is fucking meaningless. If your customers say that you’re badass, then you are. They get to choose, not you.

There’s a million days where you go to work and just untangle Ethernet cables all day but that was a fun one.

Ben Brennan’s Badass IT Team

Charlie Hoehn: I was just thinking like how awesome it would be to have a badass IT support service where it’s guys wearing leather jackets, driving around on Harleys from place to place. Kind of like the Geek Squad does but edgy.

Ben Brennan: Charlie, no bullshit, we have that. It’s called my special ops team. So props to my special ops team based out of New York City.

So we have this ragtag group of New Yorkers, it’s like a boy genius, the nerdiest dude that you have ever met in your life. It’s like this 40 year old Polish guy with every network certification ever done and this Puerto Rican guy who is also related to half our New York office. It’s very New York in the sense that it’s all Polish and Puerto Rican.

So we’ve got Jessie, Martin, and Sean, and they’re our special ops team. That’s what it says on their business card.

“They fly all over the country and sometimes the world and fix shit for us.”

I think one of them is in Boston today, three of them are going to Dallas. They love going to Florida so they all go to Florida when they get a chance. But they are a crazy bunch of drinking, super smart guys that just come in and blow everyone’s mind and leave. They are hilarious.

This is how awesome they are: I’m a musician, so one time they were in Chicago doing something, and on eBay I found a Fender Rhodes piano. If you know what those are, hard to find in good condition, hard to shop. I was like, “Hey guys, you don’t have to do this because I am your boss’s boss, but I’ve got this piano I need and it’s only set up for home pick up. Any chance you can go and pick up a 300 pound piano for me?”

No, it’s like 85 pounds. They did it and it arrived two days later after their shift. They’re amazing.

About Badass IT Support

Ben Brennan: So the book really kind of scares me because the book gets way better as it goes. The first chapter is the least exciting chapter I think.

This is not a humble brag or whatever, but my father in law had flown us into Italy over Thanksgiving and I was skipping all these day trips to go see whatever to sit there on this gorgeous villa and finish writing my book.

I finished writing it, and I’d just written the last chapter, and I was like, “Wow I am inspired by my own writing. This is amazing!” And then I read chapter one I’m like, “Oh it needs some work.”

So I had to rewrite the whole thing again. But the good news is if you stick with the book it gets better.

“It’s like The Shawshank Redemption of IT books for sure.”

So the last part of the book is cool because it’s more like, “Here’s the real shit. Here’s what you do.” So the easy part is the strategy writes itself.

Usually IT strategy is like six IT guys sitting around the table deciding in their beautiful well rounded minds what people in marketing or sales or creatives want. They come up with a strategy based on what they think their customers want.

I came up with a great idea: why don’t we just ask the customers what they want and skip that step?

So I found that when you base your strategy on what you think your customers think is dope versus what you think is dope, they tend to respond better to it. Yeah, it was novel.

I mean I didn’t think of it right away either. It took me a few years.

The Customers Know

Charlie Hoehn: It’s not an intuitive thing, oddly enough and as soon as you say it you’re like, “Well yeah, duh,” but no one does it. Very few people are really good at listening.

Ben Brennan: Yeah, it’s totally true, and the funny thing, speaking of intuitively, it’s so important to listen because very often the best ideas are counter intuitive.

In IT, when you’re building a strategy, you’re like, “Okay well, obviously we want people to have these awesome tickets from IT to have this cool formatting,” “They want us to have these cool prize drawings and stuff.” And then counter intuitively turns out they don’t even want to talk to IT.

“They want to do their jobs and have shit that works.”

It’s amazing what you find. I remember when we started implementing this at Yahoo, when we’ve really asked our customers, we found out so much low hanging fruit that no one had ever thought of.

Like it turns out, our biggest feedback was people were not saying, “Hi,” when people walked in. So our IT guys were so focused on their jobs, when you walk in for help they would ignore you until it’s your turn.

But then when it was your turn, they were like super nice and friendly. In their eyes, they were like, “Well people know that you’re giving focus to that person and you’ll be with them.” But I’m like, “Dude going to IT is weird if you’re not in IT.” You guys look weird, you have a weird reputation…

So based on that feedback, we trained everyone, and this was a very short training: say hello when people come in. And our scores went up like 10 points.

I never would have thought of that. It turns out that was a biggy. It just showed the power of listening to what people say, asking your customers first, and like you said, they’re the experts.

Sorry, famous-entrepreneur-who-has-the-world’s-best-idea. The customers are the experts at what’s going to be cool.

Real Life Challenges

Charlie Hoehn: Now the hard part comes down to firing, hiring and managing culture, right? So can you talk a bit about that?

Ben Brennan: Yeah, that’s really easy to talk about because it’s the one thing in the book I’m not an expert in. I mean hiring, firing and managing culture…I was a psychotherapist. I’ve spent 5,000 hours talking to people about their feelings. I still everyday have to work on managing culture.

I’d always worked at startups with hyper growth where we were hiring 50 employees a week. When I started at Yahoo and started consulting for these big companies, I went through my first round of layoffs and was like, “Oh this sucks,” you know?

You have to choose people and then you have to talk to people and this is their livelihood. This is, like, returning the Air Jordan’s they bought their kids for Christmas because they just got laid off in December.

“This is real life shit, and it’s really hard.”

So basically I tried to give an overview and say, “Here’s how to hire, here’s how to fire and when to fire.” The good news is, the one nugget and piece of value that I think comes from this chapter is encouraging people that sometimes firing people is the best thing you can do for your company.

As a leader, it’s hard. I’ve got like 50 or 60 guys under me whose livelihood depends on conversations I have, you know?

I negotiate, I help them get raises, I pay the rent, and I take that very, very seriously. When it’s time to fire someone, it could be hard.

I’ve even included a flow charge just to make it easier. But when it’s time to get rid of somebody, if someone’s negative, I really let people know in this book—get rid of them yesterday.

“Put down the book, call HR, and get rid of them.”

Really try to give people a big picture. When you are firing someone you’ve worked with for two years, it can be hard, but if you step back and think about the 11 other people on your team that will be better off and we’ll make more money and enjoy their lives better if that person is gone, then it helps.

Making Choices for the Team

Charlie Hoehn: So how do you know when they’ve hit the threshold of, “Okay this is now problematic”?

Ben Brennan: Right, basically you talk to your team and find out, right? The cool thing is when you’re doing badass IT, you start to get close to your team. If you have ever been on a winning team, it’s really fun. There’s a lot more celebration and a lot more happy hour drinks, you know? So you get to know your people. But you have to ask them and you have to be connected and you have to frankly just like hear the conversation behind the conversation.

“The real conversations are always not what’s talked about in the meeting but what people are texting underneath the table.”

You need to really find out about that and just be like, “Listen dude, I am trying to lead the team, what’s really going on?”

And the keyword is just negativity. If someone is not doing good at their job, maybe their boyfriend broke up with them or their cat passed away. It’s understandable if they are going through a rough patch.

But if it’s negativity—to be honest, if you’ve established the reputation of being a negative person at work, you need to update your LinkedIn and go find another job and start fresh. That stuff does not go away.

Stupid Enough to Challenge the System

Charlie Hoehn: Okay, so we covered the easy part, the hard part, let’s talk about the fun part. What does that entail?

Ben Brennan: I didn’t start doing badass IT support because I knew about this stuff, I learned this over time. I did this just because I thought if you are going to be an IT why not be really dope and have a blast doing it? It turns out that paid well, too. But as I systematized it and learned over time, I started winning with bigger and bigger companies.

“The fun part is just building dope shit and paying it forward.”

When I came to Yahoo, it was hilarious. Their IT was how you would expect a 20 year old IT company to be. If you needed IT support, you had 30 minute, 40 minute wait times on phone and chat. You couldn’t email because they decided to take email away as an option. So they were removing channels of support.

Basically you had no choice but to literally wait.

There is no voicemail, so you had to find a time where you can wait for 45 minutes hopefully and talk to somebody.

But yeah, in the bowels of that data center or whatever, like in Silicon Valley, that’s how it can be.

At Yahoo I was like, “Why can’t people email?” It was 2010 and I was fighting for email. We should be fighting to get rid of email. We had to go to email first just to start innovating.

“I had to almost get in a brawl with this tall guy with braces who’s so pissed at me I thought his braces would fly off.”

It was hilarious. It was my first week at the company and I’m like, “Dude you guys are like hell bent on not being good at your jobs.”

And it wasn’t their fault. It was just years of bad management. When shit rolls downhill, what are you going to do? Spend every day fighting the powers that be as a low level IT guy?

I was stupid enough to do that just because I didn’t know any better. But it doesn’t make a lot of sense. So we slowly started just fixing that and becoming more customer centric. We got rid of a lot of the negative people to be honest, and now that same team is doing awesome shit.

We have a mobile app where you can just pull out your phone and click and be talking to IT instantly. You can look at your tickets on your mobile app. We are working on bots and AI, bringing that in as a new channel.

We’ve got this really cool team, our special ops team actually is going to be working on the voice activated conference room. So hopefully they can get that going where you can just walk in and say, “Yo, start the meeting,” or, “Let’s do this,” or whatever.

That’s why a lot of people got into IT in the first place. It wasn’t to crunch tickets.

Let’s Find What You’re Good At

Ben Brennan: I think the coolest fucking thing about badass IT support and the most fun part is paying it forward.

My friend got me a job at IT and I just worked my fucking ass off and now, I have an amazing career that pays more than anyone in my family has ever made. I’ve got 50 or 60 guys under me that I’m able to get them paid more, and I’m able to make their career something fun.

Whether you’ve dreamed of being an IT guy for your whole life or whether you just failed at something or a bunch of things like I did and fell ass backwards into it, I think that we create a cool place to work.

I hope more companies will adopt this. It’s easy, read the book, it’s super easy. It’s free. And when you start listening to your customers and create this badass army of IT professionals, everyone gets more money. Everyone gets more Air Jordan’s for Christmas. Your kids get fancier braces, they can go to private schools if you want, you know?

It creates this awesome thing. Every single day I wake up into a gratitude meditation, and four, five times a week the number one thing on that list is the fact that I have a career.

I pulled it out of my ass, and it was the result of a lot of people caring about me when I had no plan. I just feel so lucky dude.

My wife is a resident, I am able to pay her bills. I am able to have dogs and a house. That was never in the fucking cards for me, man.

“I didn’t earn it. I got lucky and I worked my ass off and I love paying it forward.”

When you meet other people like you and like me who weren’t quite sure how to be an adult and they have their first cool boss and you’re like, “Hey dude just stick with me here. We are going to fix your salary. In the meantime, you go out and do your thing. Let’s find out what you’re good at.”

It feels so good to pay it forward, because I never thought I would have anything to pay forward.

Tough Shit

Charlie Hoehn: Can you finish that up with a story you told me before we started off when you emailed your friend and asked them for help?

Ben Brennan: Right, so this came when I just finished with grad school and I had no idea what I was going to do. I guess this was supposed to be a therapist, like a licensed professional councilor they call it.

I could not find a job. I was living in College Station, Texas, with my old college roommate. I was three months behind in rent. I was eating peanut butter and jelly—you ran out of bread and are eating just peanut butter and jelly without the bread.

Anyways, it was really fucking depressing.

“You don’t feel like much of a man at that point, whatever it means to be a man.”

You just don’t feel great about yourself.

Then I meet this guy who’s like a Harvard psychiatrist. So he went to Harvard Medical School, he’s got the Harvard hoodie that he wears everywhere, super cool dude.

His name was Adam, and my friend introduced me to him and I’m like, oh this is awesome. This guy is going to be my fucking ticket. He knows everyone in town, he’s totally going to hook me up with a job. This is dope—this is the stuff you read about.

So I played cool during lunch with him, and then afterwards I email him and I just put it on the line. I’m like, “Adam, listen man, it was great meeting you. I’m in a bad place, dude. I have zero money. I have no connections, I owe Keith three months of rent, I am not doing good, man. I was just wondering, do you know anyone and any ideas about how to get a job in the city? I know you know a lot of people. I’m just bearing my soul now, I appreciate it, anything you could do would be great.”

I sent that, and then I go probably eat some peanut butter with no bread or whatever. I wasn’t doing a lot at the time.

I think it was probably like next day or whatever. I see an email come back from Adam. All it said was:

“It’s a long way to the top if you want to rock and roll. Adam.”

I was like, “Fuck, dude.” I think I had too much childhood issues to cry, but if I could cry, I would have fucking cried at that time.

To this day, it’s a source of power and a talisman. It is something that I carry around and I remember it. But I would tell you, it was not my favorite email.

It neither paid the bills nor made me feel good. All I could think of was like, “You fucking dick!”

But meanwhile, life is hard. He knew that. And I don’t know if he just had a preternatural understanding of how life worked as a psychiatrist or if he was just being lazy, but I remember it to this day. It’s my motivating factor. That’s why that’s my favorite ACDC song, or one of them. Just because it is a long way to the top if you want to rock and roll, dude.

Tough shit.

Oh, this guy was from the Barrio. Like super low, like in Brian, Texas, way outside, history of gangs, and he went to Harvard. So I guess he knew what he was talking about. But at the time, let’s just say I went to a dark place and leave it at that.

Connect with Ben Brennan

Charlie Hoehn: How can our listeners get in touch with you and follow your journey?

Ben Brennan: Okay, you can go to badassitsupport.com or benbrennan.com, whatever is easier to remember.

I’m sure I will be cross promoting by the time this podcast comes out. Or if you are a Twitter person you can follow me @why, which is one of the benefits of working at Twitter at an early stage. There are a lot of cool handles floating around.