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This is a really insightful episode. Whether you’re already a boss, thinking about hiring a team, or actually an employee who is simply wanting to impress a boss, get a raise, or just get noticed, you’re going to love this one.

We talk about the value of taking initiative (yes, I put a real dollar amount on it). The importance of hustling and the direct association between working hard and making money.

My new Learn Lettering 2.0 course just launched yesterday, but since this episode was recorded last week you get to hear the hustle that went into production before it launched and why I worked so hard to produce Learn Lettering in such a relatively short time.

As small business owners, our employees are like our family. Just like if you have a family and kids you do what it takes to take care of them, so does a boss. No matter what it takes, I know that I need to take care of my people.

Matt and I talk about how we go about enabling people to do their best work and what we’re looking for from our employees.

Highlights, Takeaways, Quick Wins
  • There is a direct association between hard work and money.
  • I purposefully make myself poor so I continue hustling as if I was poor.
  • Bosses set the example not only in the hard work, but also in the breaks.
  • When an employee takes initiative, it’s going to show the boss that they’re worth promoting.
  • Don’t expect employees to be altruistic.
  • Bosses aren’t going to notice bursts of hustle—you have to show up consistently over time and hustle.
  • You’re going to hire people who will make mistakes, and it’s not the end of the world.
  • 06:14 Matt: I was talking to a former coworker, and she was asking if I really wanted to stop working my day job, because I get a lot of business from them. I won’t have those connections quite as good anymore, especially when the existing people leave. I’m not really worried about that. It’s like this podcast: it’s nice to talk with you and other people get to hear our conversation and benefit from it—I would go to this day job and learn what other people were doing within their businesses to give me ideas. I was using it as research, not as work. All of them thought I was some genius, so they would listen to me. I’ve just been lucky that different things I’ve worked on in different industries have taken.
  • 07:34 These people all have Masters, and are engineers, doctors, and scientists, so it was a nice group of people and I had access to them whenever I wanted to. It was wonderful to run things by them. At the beginning of this month, I finally decided that it was more of a burden. I have all these businesses and I would like to work on some more seanwes stuff, more Lambo Goal stuff, but I won’t be able to do that if we’re not caught up on all the business stuff. It has to all be done by September. My wife understood, and on paper it made sense to quit.
  • 08:44 I was losing almost $1,200 an hour working there. It made me feel stupid. After I learned that, I knew we couldn’t do it anymore. Not only were we losing that money, but we were losing other things we could add on to the business to make it more successful. Also, some bean bag time would be nice. I officially put in my two weeks, so after next week, I will officially be a full time entrepreneur without the day job.

Do Employees Have to Share Their Boss’ Passion?

  • 15:00 Sean: Kieran says, “I have a question—I work with a young web agency where the directors are still on the front lines with everyone else. This is great, but there’s a weird vibe where you are kind of expected to be as passionate about the company as they are. So my question is, if you are bringing people on to work on ‘your baby,’ should you expect them to be as passionate as you are about it, even though it may just be a job for them at the end of the day? Or is that a moot point because you would likely hire based on passion, amongst other things? Does Matt expect his guys to be super excited about growing the landscaping business for example?”
  • 15:39 Matt: Typically, I’ll ask them upfront whether they like landscaping and mowing yards. Whenever I’m hiring for any of my businesses, they know that I own multiple businesses.
  • 19:19 When I’m hiring someone for the landscaping crew, I don’t think anyone likes cutting lawns a million times a day, and since we typically have no less than ten big lawns a day, it’s a lot of work. Because the employees know that I have multiple other businesses they can grow into, they see the potential of them moving from a lawn tech to managing one of my houses and making $20,000 to $50,000 in a month. That’s a motivation that I strategically planned because I knew it would be difficult finding a low wage employee who would care about my business and be passionate about it. Lot’s of times, they’re not passionate because it is hard work and lots of my guys only get paid $8.50 or $10 an hour.
  • 20:11 It’s hard to care that the boss is making $1,000 or $2,000 a day when I’m making $50 a day. They see that not only are they getting paid, but I buy them lunch and dinner and give them bonuses all the time. I recently bought them all bluetooth headsets that cost me well over $200 per headset. I don’t want everyone thinking that they’re slaving away to make Matt money. Whenever I get new employees, I explain to them that I am not making all this money. I know they think I’m a baller, but I’m not.

I purposefully make myself poor so I continue hustling as if I was poor.

  • 21:18 I don’t want to get comfortable. I don’t want to fall back and say, “I already have a Lamborghini. I don’t want to make videos and encourage other people. I’m living the dream all by myself. I don’t need to try and help other people or hustle.” That’s not the point. I tell them, all that money goes into a pot, and that pot helps all the businesses grow. If they want to move up, the businesses have the money because I’m not buying mansions for myself.
  • 21:43 If I wanted to give a bonus or help out in certain things, I can. I don’t expect my employees to be passionate about my “babies.”

Bosses Expect Selfishness

  • 22:21 Sean: Kieran follows up with a second part: “I’m super passionate about helping the company grow, but more for selfish reasons if I’m being honest.” That’s to be expected.
  • 22:33 Matt: The employer knows that, and that’s understandable. You have to be a little bit selfish.
  • 22:39 Sean: We’re not expecting employees to be altruistic. There are selfish motives, and we’re purposefully incentivizing them. Everyone’s working hard for their own reasons. I try to find people who have the kind of values I appreciate, and I try and employ them where their strengths and passions are—doing work they enjoy and giving them the resources to do that.
  • 23:14 Matt: That is the hardest part—moving my employees to where I see that they’ll grow. Maybe they start in the landscape business, but I see that they’re really good at talking to customers, giving quotes, and bringing me in triple numbers. I had a guy from Wisconsin come work for me out of the blue. He was working as a lawn guy, but he charged three times what we usually charge and getting the business.
  • 23:59 He wasn’t just bringing in $1,000 a day like everyone else; he was bringing in $5,000 to $6,000 a day. We moved him up into running three other businesses to give quotes. The carpet cleaning business just hit $100,000 in it’s anniversary. From last year to this one. I put a little over $50,000 into that business and made it all back in a year. I haven’t met anyone else that put that little amount in and got the growth we’ve gotten.
  • 24:47 I felt pretty good to make another business make $100,000 in under two years. I think your employer knows that you’re going to be a little bit selfish, but that’s good.

When an employee takes initiative, it’s going to show the boss that they’re worth promoting.

  • 25:08 Sean: So many people don’t take initiative. “This is my job, I’m an employee. I show up and do my job and that’s it.” That’s how they think. You can do that, but don’t be surprised when you stay in the same place.
  • 25:24 Matt: The employer is always watching. They might act like you’re not going to get a raise or you’re not going to move up, but if you show that initiative, you will get that bonus. You will get that promotion you’ve been wanting. You just have to hustle. You’re not hustling for no reason.

Setting an Example

  • 25:53 Sean: The employees will look to the boss for how to act, how to work, everything. Cory McCabe wouldn’t come in and work 12 plus hour days just because—he does that because it’s the ethic, culture, and vibe here. He sees me doing it. You set the pace for people. You set the stage; you set the precedent. They’re following you. They’re watching you. I don’t want Cory working those kinds of hours all the time. Right now, we are in a season of hustle. I’m appreciating that, and that’s why I’m rewarding it with a $2,000 bonus.
  • 26:51 That’s why I set an example with taking sabbaticals. Every seven weeks, we take the week off. Not only are my employees relieved of their duties, but they are paid to take a break. I realize I have to set that example. In the early days, I wondered how I was going to hire people while I had my sabbaticals. Should I find work for them to do while I’m gone? I realized that I had to set the example, that this needs to be a team thing, a culture thing. It became the heartbeat of the company. We’re on the same rhythm: we work hard together, we take the break together.

Bosses set the example not only in the hard work, but also in the breaks.

  • 27:43 Matt: I honestly have been trying to take off the seventh week and let my employees do that, but we’re in that season where we have to hustle and it’s so hard to take time off. Two weeks ago, I let everybody have three days off. It felt like forever. I asked my employees on Monday how they felt, and they were feeling sluggish. It’s not that they didn’t rest, but when they see my pace they see where they need to be. I’ve had plenty of employees that we’ve had to let go because they can’t keep up and they don’t understand why they’re doing this. They think they’re just helping me get to my Lambo Goal
  • 28:38 It’s a whole lot more than that. This year is going to be the first year that, come the end of the year, everyone will get at least a month off paid. They’ll be getting bonuses this year as well, because we did really good. Even if you have a day job or you’re an employee, work hard. It doesn’t matter what position you’re at. If you’re an entrepreneur or you’re still doing the Overlap Technique and you’re at your day job, work hard because people are watching you, and they will judge you based on how you work hard and hustle.
  • 29:22 Sean: Ryan says, “In my past experience with a company that was trying to make us ‘passionate’ about the work, it was a very manipulative tactic on their part. They would use it as a way to say, ‘If you were truly passionate and dedicated you would work on the weekends for free without pay when we need it.’ That’s ridiculous.
  • 29:39 Matt: That’s called taking advantage. That’s a bit much.

Bosses Notice & Reward Hard Work

  • 29:43 Sean: Kieran says, “I think there’s a science to working hard in such a way that your boss will notice, which sound underhanded, but it really isn’t.” That kind of makes sense.
  • 29:59 Matt: It does make sense. A lot of my employees won’t start hustling until I walk up. They should be working hard like I’m here all the time, not because of me, but because we’re working toward the same goal of completing this job so we can move on to the next one. We’re all going to benefit from this.
  • 30:30 Sean: If you’re thinking, “I hustle, but my boss doesn’t see,” then you don’t hustle enough. You need to keep hustling. If you’re thinking that you just need to do it while he’s around, you need to do it all the time. I say that people don’t notice announcements, they notice consistency. This is the same thing.

Bosses aren’t going to notice bursts of hustle—you have to show up consistently over time and hustle.

  • 31:02 Matt: One of the biggest surprises for me was when I visited my employees while they were working, and I was let down by some of them who thought they could goof off and nap while I was away. They got demoted. Others who worked hard to finish early got the next day off and a bonus on top of that. The employer is always watching you. He’s not going to tell you ahead of time and he might not reward you every single time, but he’s not there to reward you every time you do something correct. That is your job. If you want to move up the ladder, you have to keep pushing.
  • 31:48 Sean: I feel bad sometimes. Late last night, I recorded that podcast episode. It’s crazy because we’re doing all this stuff and it’s not scheduled out like it normally is. I’m not able to do shows with Ben. I did the show, wrote up a few hundred words, made an image, and then it’s Laci’s job to set up the newsletter for the next morning. She duplicated the last campaign and changed the title of it in the dashboard but not the email subject. The email subject was the wrong subject from the last email that went out to 20,000 people.
  • 32:41 In minutes, I start getting replies from people and I had to send another campaign with the correct title and put a message inside apologizing. I had to send that out to 20,000 people and of course, I haven’t checked unsubscribe rates because it’s unproductive. If you’re doing things right, don’t check. I had to learn that. The only metric that you care about is the replies. Are people replying to you saying, “This changed my life”? That’s all I care about now. That’s all I tune into.
  • 33:27 I am aware that sending double messages back to back like that will get you more unsubscribes. That sucks. One little mistaken skip in procedure where you didn’t check something caused a problem. It’s frustrating, because I had to say, “Alright, I’m not mad at you, I’m disappointed at the situation because it has consequences. We need to prevent this in the future. What is the procedure that we’re going to implement that will keep this problem from happening?” None of that’s fun. What sucks about that is that she’s done her job perfectly all the other times. You’re an employee, you’re working hard.
  • 34:15 Some people have different personalities where they need to be told they’re doing a good job, but at the end of the day, your paycheck is what’s telling you you’re doing a good job. If you’re performing your function, that’s why you get paid. You’re not going above and beyond; that’s your requirement. It’s tough when you’re working hard and doing everything right, but you only hear something when you mess up.
  • 34:42 Matt: That’s kind of sad. Sitting in the employee’s seat and seeing that you messed up one time when you’ve done so well every other time is tough, but it’s reality. Don’t get hurt from it, but take it and try not to do it again.

The Cost & Reality of Mistakes

  • 34:59 Sean: I try to balance equally. I am harsh and kind of a slave driver. I’m a perfectionist, we have really high standards here, we work hard and we hustle, but also we’re very positive. I tell people all the time, “You did good work today.” I mean it, because I know that’s important. Most people don’t get that from their boss, so I try and offset it. Cory lost footage from the Learn Lettering shoot. This is the most mentally intense thing I’ve ever done. I’m writing daily 1,500 word blog posts on hand lettering to promote this launch to the separate 30,000 people on that list.
  • 36:02 The actual course is 75 lessons, at least 1,000 words each. I’ve been cranking that stuff out, delivering it on camera, each one 1,000 words, so many takes, multiple cameras—it’s mental gymnastics. I’m still doing podcasts and working with people and all the insane technical stuff behind the scenes. It’s a mental marathon, and the hardest part is flipping the switch. Now I need to create this, write this, do that. The hardest thing is now, after we’re supposed to be done with all of the talking videos and I need to be doing so many things, I also need to go back and find the transcripts from the two takes we need re-create, make sure I’m wearing the same shirt, and get back in the game and deliver it the same way that I did. That’s hard. It’s like digging a ditch and having someone fill it in and say, “Dig it again.”
  • 37:31 Matt: What’s the percentage of people who get into entrepreneurship that stay entrepreneurs? It’s so difficult. There are so many things, even little things, that you have to remember for your whole business to stay successful. It is overbearing and can be mentally draining. That’s been kicking my butt this time of year, the mental drain. Do we have to do this? Do we have to dig this ditch all over again after someone threw the dirt back in?
  • 38:16 Sean: Cory spent some time making sure this was really the case before he let me know because he didn’t want to let me know. It’s 100% unrelated in terms of a bonus. He messed up, and I said, “Cory, we can’t have this. I can’t be going back and doing these videos again. Do you have any idea what I need to be working on? We don’t have time for this.” I’m hard on him, but at the end of the same day, I already had this bonus prepared and I gave it to him and said, “You did good work today.” He did do good work, and the mistakes don’t mean that he didn’t do good work. Mistakes happen because we’re human. It’s two separate things:

We have high standards but mistakes happen.

  • 39:35 Matt: Being a boss, that is one thing that sucks. You started this business by yourself, so you kept a high standard and if you made a mistake you knew how to fix it quick. When I first started my businesses and I was the sole owner, worker, and marketer, if I messed anything up, I fixed it quick. It was my baby. An employee shuts down because they’re thinking, “Sean’s going to kill me. He’s got to re-shoot these.”
  • 40:10 Sean: You’ve got to remember that you’re easier on yourself. If you mess up, you’ll be frustrated and think, “I’ll have to do this again, waste of time,” but when someone else messes up, you’re thinking, “I could have done that.” They could have, too. That’s the hardest thing about hiring. You’re going to hire people who will make mistakes, and it’s not the end of the world. It would have been you, and you would have forgiven yourself.
  • 40:50 Matt: That’s all part of being a boss. You told me one time that when you hire employees, you hope to get 90% if you’re shooting for 99%. I was struggling to hire employees and you were telling me that I needed to just do it and the standard would only go down if I let it go down.
  • 41:31 Sean: My thing is, if you set a high standard, no one’s going to live up to it in the beginning—but if your standard is high enough, whatever they’re going to come close to is good enough. In some cases, they can eventually surpass you because it is their sole focus.

The Future of seanwes

  • 43:47 It’s kind of weird, because we invest really hard to grow, invest again to grow at a fast pace, and then invest everything again. Not only do you have recurring revenue covering payroll, but now you have a massive team and revenue that will grow way faster in the last year to the goal. If we make $100,000 to $200,000 in the next week or so, to me that’s not play money—it’s payroll runway. Now we can take care of the team for this many months, so what are we going to hustle on next?
  • 44:34 We’re building up these assets, courses and different things that generate revenue without us having to work on them anymore. Earlier in the show, you said that you wanted to work on more seanwes stuff. Seanwes is a network of shows right now, but it’s also a platform. I’m rebranding it as a network; we’re working on a big website overhaul and a heavier focus on the Community, because it’s the hub of everything here. It’s where the magic happens, where the live shows happen, where people connect. Around that, it’s all these different shows. We have several new shows we’re going to be bringing on, but seanwes is a little more than that.
  • 45:28 It’s not just a network of podcasts, but it has roots underneath that. The people I’m selectively bringing on our team will eventually have courses. Matt, you’re eventually going to have some business courses. Those will be on seanwes. We’re working on Learn Lettering, we’re going to be working on Value Based Pricing, Audience Building, Aaron Dowd’s going to be doing a podcasting course, Cory Miller is going to be doing a show and eventually a course, Cory McCabe wants to do a show and a course on videos, and there are other things coming. That’s the big plan.
  • 46:09 Moving toward the Lambo Goal, in the spirit of the show, over the next couple of years I’m going to be investing a lot, but we’re building something. We keep putting all the money back in, resetting back to zero, though hopefully we’ll have a padding this time. Ideally, I’d like to build up three to six months of payroll and have that set aside. That’s my immediate goal, the zoomed-out look.
  • 46:43 Matt: That’s kind of the same focus we have at M Corp. All the money goes right back into the “mothership” and all the other businesses are under that. Any business I’d like to expand borrows money from the mother, and it grows. That’s what allows me to start all these businesses. It sounds insane, but it really isn’t. When you have 15 different income streams, you can easily fund other businesses.
  • 47:37 I try to tell my employees that we’re looking toward the future. We’re not caring about the here and now, or going to Fiji for a couple of days. Anyone can get a loan and do that, but we want to have six to twelve months of reserves so people can take off half a year at a time if they want. It’s a ridiculous goal, but it’s doable if we hustle.
  • 48:19 Sean: I’m still holding out hope Matt; I want 2017 to be the year of the Lambo. 2020 was if I was going to do a sabbatical year, it would be in 2020. That would be the soonest.