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TMBA586: The Reformed “Bad Boss”

After a wild and dramatic week in Austin TX, we are excited to return to our regularly scheduled programming and to highlight an entrepreneur with an interesting career trajectory.

Casey von Neumann started out, as many of us do, by freelancing. In her case, teaching music classes to students in Atlanta, G.A.

As her client base grew, she began scaling her services into a full-blown music school called Eclectic Music and has since built multiple businesses in the education space.

It wasn’t long though before Casey discovered that she had trapped herself in the day-to-day operations of her business.

She was forced to come to the difficult realization that she was a “bad boss” who needed to make fundamental changes to the way that she interacted with her team.

Casey has recently begun sharing what she has learned from that experience by coaching entrepreneurs in an area where so many of us struggle – building, keeping, and managing a team.

Casey joins us this week to share her entrepreneurial origin story, what it means to be a “bad boss”, and how we, as entrepreneurs, can take steps at the onset of our business to create a better work environment for ourselves and our employees.

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Do you have ideas for things you’d like Dan and Ian to discuss on future episodes?

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Dan: We’re doing it live Boss Man. Welcome back to the podcast. Take off your snowshoes. It is 80 freakin degrees. We went from not having any power to contemplating turning on the air conditioning. What has happened here in Austin, Texas?

Ian: You mean, you take off my snowshoes that you were wearing? Is that what you mean? Because you stole my shoes.

Dan: I stole everything from you. I was totally unprepared for the snow-VID for the ice apocalypse. I don’t know whether to make fun of it or be sad about it. But for those of you just tuning in, Austin, Texas, had a dramatic week. The grocery store aisles were bare. Many, many acquaintances/friends lost power and lost water. There are still many residents in Austin as we record this, as you listen to this, that do not have clean water in their homes. In fact, I helped deliver some water today. Everybody in Austin, Texas, has sort of pitched in whether it’s via Facebook groups, or Reddit or Twitter or their own private networks to help each other out. So many crazy stories this week, Ian, we could fill up a whole episode with the drama on the ground. We spend so much time on the webs, real life intervened this past week in Austin.

Ian: Well, yeah, the internet was out for many, and power, so really hard to be online. Yeah, lent my boots to you, hope those were of use. Lent my shower to many other people. And it was just a disaster area. This ice apocalypse hasn’t happened in Austin, certainly didn’t happen this severe for over 40 years. So to say that houses and people and infrastructure was not ready at all.

Dan: And, I mean, just to give a little image for those of you who are trying to figure out, hmm, what is it about some ice and six inches of snow? Essentially what happened is city wide, the pipes burst. And then statewide the power grid went off. And so you have like massive flooding across the city. So you can’t just like you know, turn off the water and flip it back on. First off, all the pipes are frozen. Second off, all the pipes are broken. Third off, the power is off. And so people are freezing in their apartments, trying to figure out new places to go, and you go out on the road. And because there’s no salt trucks, there’s no infrastructure to deal with winter storms, you can’t move anywhere. And so now you just have these dominoes going off and off and off. And then you have people with the four by fours rushing out to the stores to get as much equipment as they can, because they know they’re going to be locked down. And I’ll tell you this Ian, honestly, I don’t think I’m exaggerating to say we were 24 to 48 hours away from a full social meltdown, whatever that means, some kind of panic in the streets. It was serious. We were close there. And it just reminded me of how fragile so many of the systems in our society are. And it holds true for business too, so many of the things that we think are just always going to be there. What’s the example right now in business like Amazon S3 will always just be there. Someday it won’t be Bossman.

Ian: Yeah, someday it won’t. Someday that magical power that just gets delivered to your house will not be there. And that was definitely the case in Austin. I do want to shout out because this is a company worth following HEB, which is a local grocery store chain in Austin, Texas. HEB, they’ve made some headlines over the last couple of years. They are what you want your government to be. They’re prepared. They have a disaster plan in place. They pay their employees really well. They make sure that people have food when they need food. The power went off and one of the HEBs and they just told everybody to walk out, with all their food. They were the first company to come back online as this disaster was unfolding. Really interesting company to watch the way that they operate.

Dan: Yeah, the way they do marketing, the way they treat their employees. And I’ll say that one of my favourite on Reddit you call it a ‘s-post’, like is someone posted in the middle of snow COVID or ice apocalypse. There are three certainties in life – death, taxes, and HEB providing more leadership than your local government. And it is such a cool business case study of a group who steps up and really provides a source of leadership in the community. That was comforting to see because we simply weren’t seen a whole lot from our elected officials.

Ian: You didn’t hear anything. It was interesting. You know, Ted Cruz famously got on a plane to Cancun until the paparazzi caught them. Mayor Adler who’s the mayor here in Austin, was on a news conference, a zoom news conference and he didn’t have a sweater on and he had this like picture lighting going on in the background.

Dan: Warm, bright light in the background.

Ian: Non essential lighting. And someone was like, ‘Hey, dude, get a clue, man. People haven’t had power for like seven days’.

Dan: Look, I hate to gesture in crazy pathways, Ian, but it hasn’t been a great run for government on this continent. What me and you should have done is been on that plane with Ted Cruz going to Cancun. I can’t wait. But anyway, let’s get moving on to the meat of this week’s episode, it is a conversation with someone who is an amazing contributor to our online forum, the DC. In fact, reading a thread there, Ian, is what inspired us to invite her onto the programme today. Or, of course, the DC stands for the Dynamite Circle. She has a really interesting trajectory that personally I related to as an entrepreneur. And specifically, she’s pivoted several times, as we all do.

Casey So I started out with Eclectic music. I have a music school in Atlanta called ‘Eclectic Music’. And we do camps, classes, lessons for kids and adults. Even during COVID, we have about 300 students. Then I also have a small private school. It’s a tiny homeschool group in Atlanta, called ‘The Little Middle School’. And so that usually has between 25 and 27 students every year, and a handful of teachers. I’ve started an online school, but I’ve definitely kind of moved away from that, it has a handful of students. And then I moved into coaching and consulting for business.

Dan: That is the amazing Casey Von Neumann. And as she says, she started as a teacher pivoted into being a small business owner in the education space, and is now feeling out coaching, particularly in an area where we know, in many business owners struggle, building, keeping and managing a team. We’re gonna go into all that on the show. And along the way, you’ll hear me refer to some notes that Casey sent me ahead of the recording, which I appreciated. So let’s get going. We started with Casey’s first entrepreneurial play, which was probably in her genes.

Casey: I do have a degree in music education. But I was really doomed to be an entrepreneur, from the get go. Both my parents are really entrepreneurial. My dad was the balloon man in my hometown, where he would dress up as a clown and bring his guitar around with bouquets of balloons and sing to people for you know, birthdays, and anniversaries, graduations, that kind of stuff. So, you know, for years, I was ‘the balloon man’s daughter’. So I just saw that I just kind of saw always that you could just create something out of thin air. And that’s really what I grew up with far more than the narrative of, ‘you go to college, you get a good job’. That was something we never talked about. So even when I did have a job, it was always sort of jobs where we have a lot of autonomy, like being a server, being a teacher where you have your own classroom. Then, I started teaching music lessons, moved to a new city started teaching music lessons.

Dan: Which city was it?

Casey: I moved to Atlanta, from Maine where I’d grown up I you know, spent a little time in California, you know, like in our twenties, moved around.

Dan: Why did you move to Atlanta, a strange choice. That’s you and John Mayer, huh?

Casey: Two New Englanders trying to get out of the cold, I guess. It was an affordable city. It had good weather. I had some family there and what I found too was that it was a little bit like Austin is now where it wasn’t entrenched. Like if I’d gone to Boston and started teaching music lessons, people would be like, ‘Oh, we’ll be taking music lessons at this place that was founded in 1849’. But Atlanta had nothing, Atlanta really didn’t get going until air conditioning came along, and like the 60s and 70s, so it’s basically a new city. So I was able to just go and hustle, you know, put up the classic flyers and coffee shops that had my website on them and I got phone calls.

Dan: Your game plan – you drove down to Atlanta, which is like, a 15 hour drive or something. And you literally your game plan is to teach music lessons to pay your rent.

Casey: Yeah, yeah so stupid. And it totally worked.

Dan: So how much do you charge for them? What are you teaching?

Casey: I lived in this terrible apartment, didn’t even have central air conditioning, tonnes of cockroaches, the classic. Of course, I fell in love with it, because it’s like, ‘Oh, my first apartment’. And I taught piano lessons in the bedroom, because that’s where I had my rinky dink digital piano. And then I taught guitar lessons in the living room. And then I would also go to people’s houses. I was driving a really old Pontiac Bonneville at the time that just barely made the trip down from Maine. Going to all these like million dollar houses with these $50,000 cars and like I parked my thing out front, like, ‘I’ll park down the block for you’. But, but people really liked it, I was good at it. And I was good at building relationships. And I was good at leveraging those relationships to get referrals and build it up.

Dan: Was Atlanta a culture shock for you?

Casey: In some ways, yeah. Because I was not used to a culture in which people spent money on their kids, I grew up in a really small town in Maine, it was a tourist town, it was really dead during the winter. It was the kind of place where it’s like, ‘Mom, I want to play the guitar’, ‘Great’. ‘Play the guitar. Here’s one’, you know, ‘Have fun’. And it wasn’t like in Atlanta, where it’s like, ‘Oh, let’s get you you know, hundreds of dollars a month worth of lessons and anything your heart desires, sweetie’. The pressure that was on these kids was like nothing I’ve ever seen. And the culture of spending money on kids and investing in them investing in their development was like nothing I’d seen, as well. So I would say within five, six months, I was pretty much making it. I had enough work to get going. My standards were really low. But I was able to pay my rent, and make it work.

Dan: When did it become more than just paying for the rent for you?

Casey: So after a few years, and it wasn’t intentional, but after a few years, I really did quite have quite a big referral base. So I was at this point where I had people coming to me and I was having to either turn them away or I would say, ‘Well, the is summer slow. I can take you for this summer. But then after that, I don’t have any space in my schedule and I don’t have anyone to refer you to’. And they were like, ‘Okay’, and I was like ‘That’s strange. It’s strange that they’re not going to go look for someone else, for another music teacher’. So I thought, oh, maybe I can bring other teachers into this neighbourhood. And I can set them up with a place to teach, I can set them up with referrals. And so then I started to grow it beyond just me. I guess that was probably about five years after I got going..

Dan: At the time, you’re like, ‘I’m just gonna teach these kids guitar for the rest of my life’.

Casey: The actual teaching is something I really loved doing, but I was unsatisfied with it for the obvious reasons that most of us are dissatisfied with freelance gigs after a while. You’re always having to hustle for the next gig one person’s decision to change something, you know, they’ve got soccer practice now. Well, now you’re out that money. And I didn’t like working through dinner. Because you start working at 3pm. And then you work through till eight. And then of course, like a lot of us. I read ‘The Four Hour Workweek’. And I was like, I want that life. I want it.

Dan: Describe to be me what specifically appealed to you about ‘The Four Hour Workweek’.

Casey: It was just the audacity of the four hour workweek that really appealed to me. It was something about just the way he questioned everything. The way that he was framing certain operational challenges that I had run into, like the endless email. And the way that he pushed back against expectations. The thing that I thought of, the thing that still sticks with me from that book that I quote a lot, is the idea that you have to be willing to let little bad things happen in order to have the upside.

Dan: That’s a really powerful idea, especially like a lot of freelancers or crafts people. And the art of letting little bad things happen is like antithetical to being a good craftsperson. And I see a lot of folks struggle with that idea. So what did you do about it, though?

Casey: Mostly, at first, I just kind of listened to the audiobook while I was walking around and just let just thought and let things percolate. And I had started to bring on people and I had started to look at different ways of creating leverage for myself. But I didn’t have the courage really to stop doing what I was doing. I didn’t really know how to get out of it. And even when I started my second business, which came a few years later, it was still something that had me very tied down.

Dan: So describe the first business. Did you like start renting a location and doing lessons at a leased location or how did it work?

Casey: We rented first one then a year later, we rented another and then another. We’re back down at two ish right now but yeah, I kind of let it grow.

Dan: At this time, we’re not doing lessons anymore?

Casey: I was still teaching a bunch of lessons on top of being an administrator.

Dan: Were you making good money?

Casey: No, no, Dan. No, I was not.

Dan: Why not?

Casey: Because that was not the first thing that I started with. And that was a fatal mistake. So instead of thinking about – here’s how I get paid. But while it’s still on paper, and you know, really getting that proof of concept down, while it’s still on paper, the way that you guys talk about these ideas every single week, it was like, ‘Here’s this thing that people want. And here’s this thing that I can offer’. And I left out that part about really making sure that I get paid for it, and really valuing what I was bringing, In fact, I tended to undervalue what I was bringing, because I kind of assumed because it was easy for me, ‘Oh, everybody can do this’. Everybody can go out and find business. Everybody can get repeat business, because they’re good at what they’re doing. Everybody can go out and find the place to teach and the materials to use and all that stuff. And it turns out, no, that was actually a skill set that I had developed. And that was valuable. But I just did not set myself up so I paid myself for that.

Dan: It is powerful. Once you get introduced to the entrepreneurial skill set, you realise that like, it’s not as widespread, just pulling together a profitable system, on top of a very common thing like music, education, or whatever it isn’t. It’s not that common actually, like a lot most people do in commerce aren’t figuring out economics at scale, or even like, it’s just a small medium scale.

Casey: Right and, tT=o be honest, I really learned how to do that. And I learned how to think that way listening to this podcast. Because I wasn’t having that conversation with people that I knew in my day to day life.

Dan: So I’m just reading. ‘I started listening to the show in 2014, I was an administrator and teacher at two different schools that I had founded and didn’t know how to escape’. And then you said it took until 2017, so three years for you to be able to leave the business for one month. So what were the things that were tying into the business? And how did you begin to extract yourself?

Casey: I guess I had a little bit of that hero complex that some of us have, where it’s like, ‘This is the thing that I made. Therefore, I have the unique genius that keeps it running, nobody else can do but me’. And it wasn’t until I was willing to put that ego aside a little bit and invite other people to be part of it that there was some room for me to have a little space and freedom to do the next thing or to just not work 14 hours a day.

Dan: It’s like that lone wolf genius complex is like really good through years one through two or whatever. And then it really sucks year three through whatever.

Casey: There’s this weird shift that we have to make because like for the first couple years, where you’re just hustling and you’re just doing everything because it’s easier to pay yourself to do it, makes more sense to yourself to do it, or sense to pay yourself to do it.

Dan: And because no one else is willing to do it

Casey: And you can’t afford to have somebody do it. So you’re just like, ‘Okay, I’m going to learn how to do all these things’. That’s how you talk yourself up is like, Yes, I can do this, yes, I can figure this out. And then at a certain point, you have to pivot. And you have to say, ‘I’m not the best person to do this, Nope, I’m not the best person to do this’. And you have to systematically hand everything off. And so that that’s a really big mindset shift that I had to get through.

Dan: What happened?

Casey: Well, the vision for what could be was really important. And so I came across the TMBA in 2014. Believe it or not, it wasn’t even through the podcast, it was through the blog. And that was like, ‘Oh, okay, these people are doing it’. And you had such credibility with me because you and Ian weren’t like the typical online business thing where you’re like teaching people how to make money, by teaching people how to make money by teaching people how to make money and on and on.

Dan: It’s because we’re not smart enough for that stuff.

Casey: But the fact that you actually like, ‘Oh, these guys are living in Bali, with a manufacturing business’, it blew my mind. And I loved that. That was how that was the sort of oblique way that you all implemented ‘The Four Hour Workweek’ and took those ideas and ran with them. And so even though I’m the only one I know, in my world who wants this, there are other people out there who want this who have figured out how to do it, it’s real. It’s not just this fantasy. And so getting into listening, and then eventually becoming a member of the DC like, finally meeting people face to face, who had these types of businesses and had designed their businesses, not just that they would were able to escape them, but with the intent of having that location freedom and that time freedom that really spoke to me. So once I could see it happening and see like, ‘It is no big deal. This is just this is just the business that I started, you know, that winter in Chiang Mai’. It’s like, ‘Oh, okay’. Like, that’s, that’s, that’s how to do it and then it was a lot easier for me to see that path for myself.

Dan: That’s a huge deal. And like we talked about, like validation in the startup world. Validation, it’s not as available as you think even in successful businesses. It’s not always the case that people are just like chucking money at you from day one. And I can remember in multiple businesses, I was starting where I was getting the opposite of validation from intelligent peers sometimes too. You feel like you’re crazy sometimes when you’re doing some of this stuff. I think it’s like, well, just worth underlining that, you know, even things that are on the path of great success, like you can feel a lot of negative feedback while you’re doing it. Even if it’s not overt negative feedback, just people – they don’t buy it, they don’t see it. They don’t disapprove of it. Not a big deal, but just that kind of stuff wears on you when you’re not getting positive feedback. People aren’t dumping money, like rolling up the Brinks truck into your bank account. That’s a real thing.

Casey: You got to know who’s safe to talk to. My dad said something to me a long time ago that stuck with me, he said you don’t you don’t give everyone your good stuff. Really there’s a level of trust there, that not everybody gets to be privy to. And that doesn’t mean that you can’t be real with people or that you try to project this facade of invincibility or something. But it just means that for those things that are kind of the fragile, tender shoots of like, ‘I’m thinking about doing this’, or ‘I’m thinking about starting a business that’s called this’, it’s like, be very careful who you share that stuff with. And it doesn’t maybe go out to the real world, or to everybody until it’s good and ready until you don’t care what people think about it.

Dan: I’m feeling a little bit of that right now. That’s a real thing in business, I just want to underline that idea.

Casey: Right. At Christmas you get, ‘What are you doing again? What’s your business again? What are you doing now?’ Because it’s because it’s not the typical thing. And so for me, that was an identity, like people like ‘Cool. Are you still teaching music?’ It’s like, ‘Well, the answer to that is complicated’. You know, it was so it’s like, yeah, I’m just gonna smile, a nod. You go to the dentist and they ask you occupation. I don’t know what to put for that anymore.

Dan: Okay, so the next phase now is like, you’re starting to identify more as a founder. And it sounds like you start to realise that you need to diversify your income streams. You mentioned some problems you’ve had with the school business. How did you begin to address your concern about that primary business?

Casey: Maybe I was reading too much Taylor Pearson or something but I really started to get this feeling that …

Dan: So Taylor Pearson writes a wonderful blog, essentially about the fragility of the economy, or, you know, any business basically.

Casey: Right, so I didn’t know when there was gonna be a ‘black swan’ type event. And so there I was, it was 2018. ish. And I was like, you know, I’ve got all my eggs in one basket here. Everything that I’m doing, even though technically, it’s two businesses. It’s all involving education and kids and families in one metropolitan area in the United States. And so imagine if something were to happen to disrupt that economy in some way, what would happen?

Dan: This is a clear phase of entrepreneurship: paranoia,

Casey: Little did I know, it was completely well founded. Who could have known right, but I’m probably Taylor. But it was this moment where I was – I’ve got to figure out what the next thing is that I’m going to do, I’ve got to be moving away a little bit from this. So I just kind of thought about another book that’s been a real influence on me is Cal Newport, ‘So Good They Can’t Ignore You’, where he really talks about this idea of leveraging your career capital, you don’t make this flying leap, ‘I’m going to quit everything and jump over here. I’m going to take what I’ve learned so far, and then use that to make my next pivot’. So the next obvious step was going to be an online school where I was going to work with families from all over, which I didn’t know that COVID was also going to disrupt that. But so I got that started. Then I started getting into business coaching, which was a leap for me, so I’ve been doing a lot of that. And so by the time that a year or so had gone by I was in a pretty good position where I was ready to diversify.

Dan: It seems so obvious to start an online school, was that a bigger challenge than you suspected?

Casey: I really wanted to take a boutique approach to it. And ironically, when everything went online, then it actually set back the enterprise because part of what I was trying to assert was that school doesn’t have to take all day, online school can be a lot of offline experiences – you can have time for your family, you can have time to study and volunteer in the community and do all the little fun activities. And I was just going to be a smaller part of that.

Dan: So this isn’t a music school, this is a middle school.

Casey: Right this is math, science. Everything and so, but I came up against a couple challenges. The first is COVID, basically, because then online school meant something different to everybody. Like everybody went., ‘Online school, this is horrible’. But it’s like, well, no, it’s just they’re doing it wrong. It doesn’t have to be this terrible. And then the second piece was a values conflict that I really wanted to sort of create this bespoke experience for people. But then I realised that I had come up against a values conflict where I needed to figure out, what do I stand for with this? And so I think it’s still something that I want to invest in. But right now, the education space, and with COVID, and everything my schools have been doing, ‘Okay’, but I just want to stabilise those things, and, and then I’m working on some other projects more in the b2b space. Where, where there’s a little more, a little more leverage and ROI and I can pivot back to the education space when I feel I can make a contribution.

Dan: So rather than seizing on the online education business opportunity, Casey is now starting a new business, drawing on her experience in both creating businesses and fulfilling teams, something I know a lot of us struggle with.

Casey: Well, I love talking about this stuff. Because I feel like I’m a reformed bad boss. Like a lot of us, I started with the best of intentions. And I had this vision. And of course, I wanted to be a place where people wanted to come to work. I wanted to collaborate, I wanted to give people freedom. But I didn’t know how to see things from the perspective of my employees. So there was a lot of stuff that I just thought, ‘This is the right way to do it’. And didn’t realise that I had an identity. And I had a set of values that I just wasn’t expressing. And so I would just expect my employees to be able to read my mind about specific things, but also the sort of general overall way that we wanted things to feel. I got involved in Seth Godin’s Akimbo workshops. So I got into coaching there. And a lot of it is around people being stuck, you know, they have a vision for a thing that they want to create, but they don’t really know how to move it forward. They don’t know how to organise all the pieces and parts. And they’re stuck on like, what do I call it, and what’s my URL and, and my logo, and I’m really having the job of helping them figure out how to take action. As you guys talked about so often, it’s like really though, you just find someone who’s willing to pay you money, and solve a problem for them. And then you do it again, and you do it again. And then you will figure out where you fit. We’ll figure out what was more you will figure out the answers to all those big high level questions maybe two years in three years in, six months in maybe but yeah, you don’t have to start with like the lofty stuff you can start with like the scrappy stuff, and just taking the action moving it forward.

Dan: So were people getting stuck because they’ve got head trash or are they don’t really understand what entrepreneurship is all about? Where’s the sticking point that you’re seeing?

Casey: I think some of its head trash. And I think a lot of it too, is that people have more than one idea. And they get stuck in this sort of solopreneur mindset where like, and whoever invented that word, I don’t I really don’t know about that word. Because it’s like, if your business is not you, and so if you can, like if you have a business that you want to not be you if you don’t want to be a freelancer, then you can decide to be an entrepreneur, but let’s not conflate the two, they’re not the same. Not that I haven’t up on my soapbox here, but, um,

Dan: Well describe that a little further, what’s the problem with being a soloprenuer?

Casey: Yeah, if you get stuck in this sort of this fantasy of the solopreneur, hashtag, ‘girl boss’ kind of thing, where you believe that your business is meant to fulfil this personal mission for you, and that you your identity, like you set up your URL, it’s your name, and your identity is wrapped up in this business. So then your choice about which colours to use in your logo becomes a choice about your own identity. And I think that’s a place where a lot of people fail, and where people get stuck, because they have to be able to let go of the business as an entity and recognise that it’s this thing that is separate from them. And it is meant to make money, it is meant to fulfil a specific purpose. But that purpose is not necessarily your own personal fulfilment. So just figure out why you’re doing it. If you’re doing it to make money, figure out how to make money, if you want to foster a fulfilling thing, let go, the idea that it needs to make you money so people get all twisted up.

Dan: Wow, people are coming with their pitchforks. ‘Your business, if your intention is for it to fulfil you, is going to make it problematic for you both to have a business and be fulfilled’.

Casey: I think that that’s true. I’m not saying you can’t be fulfilled through a business, but just know which thing you’re prioritizing in the moment, you can’t prioritise both on day one.

Dan: Yeah, I agree, there was a version of what you’re saying that motivated my comment, which is – I noticed a lot of people, they’re trying to solve their own problems in other words, like, instead of, like, truly doing the thing that entrepreneurs do, which is, for example, collect money to solve problems, it’s just that simple. And once you have that skill, it’s cool, too, because then you feel like I feel insulated from ever having to, like, do things I don’t really want to do again, because there’s a lot of ways to collect money to solve problems. So, you know, that sense in my early 20s, I had of like, being so so stuck. There is this conflation, entrepreneurship has become like a consumable. It’s become like an Instagram lifestyle, or whatever that you can purchase and participate in and it’ll solve for things like meaning. That’s a dangerous game to play.

Casey: Right, exactly. And to your point earlier, like being paid to solve problems great, I also had to figure out the line between the ‘done for you, done with you versus DIY’, like where I want it to be and where my sweet spot is in that turns out that strategy is my passion, I’m not interested in starting an agency to actually do the execution. But I also do love collaborating with people and collaborating with business owners to kind of show them the ropes. Looking at that, a couple different places: that first scary place where you, maybe you’ve hired the one VA, and you’ve automated as much as you possibly can. And it’s not fixing the problem anymore. So many of us are really good at the hustle. So we’ve got the sales and marketing engine in place. So then how do you go from that really busy thing where you’re the head line cook the headline cook calling all the orders in the kitchen? And like you don’t you need someone to serve the food. But how do you train that person? How do you hire that person? Like, how do you take the time out to hire that person. You guys are doing a really good job of solving that particular problem, which I think is really needed in the marketplace with Dynamite Jobs.

So you can’t remember what it was like to be an employee. So now you’ve hired this person, it’s like, ‘Oh, good, this is on fire, here, take it’. And I’ve been in that position so many times where it’s like, I don’t even know how to onboard this person. Because I just don’t even have time to slow down. Like we’re just running, running. And that’s just a recipe for unfulfillment for you for the person who you’ve hired, like, they’re not going to be able to perform at the level that they are capable of under those conditions. And what they want is to do a good job, like their job fulfilment doesn’t come the same way that ours does, an employee has a different set of metrics most of the time, and if like, ‘Cool you’re here so I can now ignore you so I can do my job’, that’s a lonely place to be, for that person.

Dan: I think a lot of people listening to the show traditionally would have balked at the idea of management, because they believe it’s primarily about task management. And what they want to do is be builders. So they then say, ‘Okay, every time I’m explaining, like, my SEO strategy to you is like a moment, I’m not doing one myself or whatever’. But the reality is, I don’t think good management is mostly about walking through tasks with people.

Casey: No, no, the people listening to this podcast, if they are builders of businesses, they’re investing time right this minute in their professional skills. And there are so many things that are going to be relevant to the people on their teams that they can pass along in various ways. It might not be the highest of high level strategy. But there’s a lot of stuff like the productivity things that we invest in, and the books on leadership that we might read or the books on just thinking big that we get into. I think for a lot of people, they’re assuming that maybe their employees are not interested in that, are not going to be on board with that or that it’s not worth it to share those resources or to, to give them that information. And I have found that it absolutely is, maybe not with every single person. But there’s a lot of people that I’ve worked with who are really hungry for growth. They’re hungry to learn more. If I’m levelling up, how does that create space for them? I have conversations with people on my team that are every bit as fun and fulfilling as the kinds of conversations I have with other entrepreneurs. So it’s really ironic that I felt so lonely for so long thinking didn’t have anybody to talk business with, when actually the people on my team could have been those people, and are those people now.

If you mentor your people, then that will come back for you. And it isn’t this thing that you have to do all these 360 interviews, and spend all of this time in a conference room, building your culture. It’s something that you can do day by day, but it’s really just about investing in the people that you’re working with. And understanding that the people who come work for you, as an entrepreneur, don’t necessarily have the same needs. Like, I don’t want to have a boss. I’m a terrible employee. I’m not good at having a boss, but somebody else who’s working for me really wants to hear that they did a good job, and they really want an opportunity for growth, and it’s my job to provide that for them. I have one employee in particular, who’s amazing. Her name is Jen, and she said to me, ‘I didn’t realise this, but I only work at a company for two years. Because after two years, I outgrow the position, there’s no room for growth, I get bored, I move on’. And now she’s been in my company for three years. And she attributes that directly to the fact that she has these opportunities for growth. She has direct mentorship, and I’ve invested a lot in her skills, her ability to be productive, a lot of the things that I’ve learned, I pass that on directly to her. But then when I talk to another entrepreneur, it’s like, ‘Oh, cool, I’d like to have that too. Yeah, you’ve got really great people, I’d hire those people’. It’s like, ‘Yes, they are amazing people. And I’ve invested a lot in them’.

Dan: It is financially rewarding, potentially. That’s the hard work for the entrepreneur, it’s kind of your job to find the margin. If you can find a highly profitable cash flow, then you can typically hire people who have already managed those sorts of cash flows in the past. And so then the conversation tends to be purely about values, and they’re teaching you stuff. Whereas if your cash flow is more meagre, or if you’re an earlier stage of business, typically you’re bringing in people, unless you have startup funds or some other sort of source of funding, you’re typically bringing in people with low levels of experience managing those sorts of cash flows. That’s really challenging. I think a lot of times, that’s what people are essentially complaining about is the fact that like, it’s hard enough to have the values conversation. Now we’re also having the SOP conversation. And now I’m also basically training them on everything. And often the reason for that is you’re just not making enough margin.

Casey: Yeah, I think there’s a tendency that, that, that I know, that I had, where I’m like the Grinch, you know, with handing everything to his little dog, ‘Here, you’re gonna pull this sleigh’. And the reality is like, just because the entrepreneur was willing to wear a million hats and learn how to do a million different things like whoever hire, I need to give them a much more circumscribed and defined role. But I have found that I can hire someone with a relatively low level of experience, who is still that A player. And they’re a quick learner, they’re excited for growth, and they are receptive to even learning some skills that aren’t in the domain that they may have specialised in up to this point. I think that there are ways to make the most of what somebody’s capabilities are by not trying to hand everything off to that one person and not giving them more responsibility than they can handle.

Dan: Do you have a couple of quick tips like how do you manage your team supporting the new superior to what we’re seeing out there in client land. Some small things that people can sink their teeth into the another you do that really works?

Casey: I think there’s a really heavy emphasis that we have on process, and really learning some best practices, not in the spirit of, ‘I want to monitor you and make sure that you’re like, you know, wringing the most out of every hour, but so the you can find more satisfaction in your work’. So we teach people exactly how to process their email and how to organise their time, organise their calendar, we’re GTD nerds, that’s David Allen’s ‘Getting things done’. I read that book three times to try to figure out what the heck he was talking about. But I don’t expect my team to. So I’m going to train them. But they’re going to train their teams. And then deliberately scheduling conversations that are just for the purpose of mentorship. So that would be me with all of the people who are directly reporting to me. And then also the people who are directly reporting to each of my leaders have those conversations too, that’s just part of the culture that we’ve set up, where it’s like, hey, we’ve got this hour, however, often once a week or whatever, where, ‘This is just for you’. This is for you to talk or it’s just coaching, like exactly the way that I would do with a client, it’s just that the domain is slightly different, because I’m talking to an employee, but it’s still about, like, what’s working for you? what’s not working for you?

Dan: If you think about the levers there, for me it’s like, if you choose between business partners and key employees, say that, four hours a week – you have five direct contacts, you know, you speak with four of them every week, and you rotate. So you’re talking about like, one day, half your day. And think about the lever that that is, everybody there is working six to eight hours a day. That’s a huge lever. I love that Steve Jobs thing. It’s like, ‘Well, how do you, you know, manage 10,000 employees’, whatever, it’s like, ‘I only talked to five of them’. So this like investment, it matters, like the quality of those interactions matters, because it’s always happening, regardless of whether you acknowledge it or not, you’re speaking with five key people in your business every week regardless. So if you can uplevel the quality of the people you’re talking to and the conversations, you can experience some extraordinary leavers.

Casey: Exactly, I think that the return on investing in your own skills of leadership is often worth it. And some people who are in a front facing business, where maybe you’re working in the wellness industry or something, you want the people who are working in your business to get the good stuff that you’re giving to your clients. There’s got to be this harmony with the culture that the people who are working for you have are representing the brand that you’re outwardly saying that you believe in.

Dan: I’m feeling how difficult is – the initial frustrations of getting the wrong people and not knowing what’s going wrong or why isn’t it going as well. It’s messy for most of us.

Casey: And who do you ask for help with that. So that’s where I want to step into is being able to be a source of support that’s scaled appropriately to where the business is ,that you’re not going to hire some management consultant who’s going to come do 360 interviews with everybody and sit them all down at a big giant conference table. Can you use improving the operations as the mechanism for finding the places where things are breaking down?

Dan: You’ve quoted a lot of concepts from the TMBA catalogue that were contributed by listeners or guests over the years, I want to ask you a difficult question and ask you to make a couple contributions yourself. What would you like to emphasise in the entrepreneurial catalogue, so to speak that you would encourage people to think about a little bit more?

Casey: It’s really important to build in the beginning, the kind of business that you want to have. And so before we talked about this choice between the fulfilment and the money, but I think there’s a piece that connects those, which is – what do you want to be doing in the day to day? And is this headed in the direction that you want it to go? When I think about my first business, the music school that really didn’t pass the test, because I didn’t build in the financial margin to be able to make choices, to be able to market appropriately, to be able to develop the team appropriately. It kind of got stuck. So knowing what I know now, while I still don’t think we have to go, ‘Cool, but now we’re going to spend 15 grand on a website logo’. I do think that before I even start I want to say what are the non negotiables – how much time am I going to devote to this? What am I looking for for an outcome and if I can’t see a reasonable plan of like, ‘Cool, I’m willing to do this work every single day to get here based on the plan’, then it’s okay to walk away from that. I can rip, pivot, jam in some other space, I don’t have to be attached to this particular one, there’s always going to be another idea. And if you listen to this podcast long enough, you will hear the free ideas being doled out. So I think that that’s a really important one for me is – make sure you’re building a business that you actually want to be part of, at every stage of the game.

Dan: Big shout out to Casey for dropping by the show. You can follow her on her blog, ‘we are rulerless dot com’. What an incredible week. Thanks for hanging in there with us last week and this week. Me and the boss man, you know, we’re still dusting off those winter boots. Just wonderful to be with you during these crazy times, bound to get crazier. All that said we will be back next Thursday morning. 8am Eastern Standard Time.

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