381 - Why You’re Stuck In Business (Despite Working Hard)

0:00Someone didn't do the right thing and it created over$250 ,000 loss. it can take the whole ship down. It's the most important trait ever. And that number one trait is Marie Forleo is a leader. One of the top life coaches on the planet. Award-winning entrepreneur. She's an extraordinary woman. Marie Forleo. This is really exciting. One of the things that we have really never done is taken people behind the business in a very real sense. So I'm sitting here with Tana, who is my VP of operations. Hello. And so it's been over 12 years since we're working together. Yeah, we started in 2011. So it's been a long time.

0:50It's a long ass time. I'm always so grateful that you and I get to work together because so many folks that I know don't have someone like you to work with. Oh, thank you. No, I think about it. I was waking up last night. We've been spending this whole week together. By the way, we're doing something that we've always done, and it's kind of gotten more sophisticated as time has gone on. But we spend about a week together, and we dream into what the next year is going to be. I think it's part of our origin story, too. When we met, that's what we did the very first day that we met. Oh, my God. That was so crazy pants.

1:29So I got to say, when I talk about you to people, I'm like, because I basically have two work wives in my life. You're my internal work life. And my best friend, Chris, is like my external work wife. So I basically have two wives. And it's great. And I have no husband. Polygamous. I am. I'm like, look, get out of this over here. I got so much love to give. And I'm not married. And Josh is like, when are we going to marry? I'm like, I already have two marriages. But let's talk about how we met. So, okay, I know this is one of the things that the girls always tell me, especially on social. Like, they want to hear about the early days.

2:02Like, tell us about the early days. So I started my business way back, Y2K, the year 2000, right? So, like, online businesses, social media didn't even friggin' exist. Like, it wasn't even a starlight in the digital parents' eyes. Like, right, right? It was only email and, like, the internet in and of itself was still fairly new. And I remember like about 10 years of my business had gone by and you guys, I was so, I was like crumbling because I was doing everything myself. I had one employee and I had a bunch of freelancers and like different people that I was kind of working with as contractor like basis.

2:39But I remember having this huge insecurity going like, maybe I'm a kind of good coach because I love helping people and I love creating content, but I'm a shitty entrepreneur because I was drowning. and I felt like I had so many ideas and there was so much potential inside of me, but I did not know how to expand the business beyond what I was already doing. And I was at like a personal development event and it was talking about like, what's like the biggest goal that you could set. And I remember I was like, I really, really, really, like my biggest hope and dream was to attract a team member that I could work with that would help me mine kind of the incredible potential that exist and to make bigger change in the world and more people's lives.

3:20And it was like within six months, you showed up. But here's how it happened. You want to tell it? Well, you want to tell your part of how that happened? So I was transitioning out of a role in a similar type of industry with a person who had been a mentor to you in your early days starting your business. So you were friends. He sent you a note saying, hey, are you hiring? I know this girl, Tana. She's transitioning out. I think you guys would actually get along really great. And so you asked me the question. You were like, whoa, OK, what do you do? And it's so funny because you were actually on that trip to Spain with Josh that you talk about.

3:58Yes. And everything is bigger. Yeah. That I did the Oprah talk about. Yeah. Yeah. That was just a pinnacle trip in your life. And you've talked about that in the past. But you were on this trip. You were in Spain. You were really, really trying not to be online. But I think when the email came through, you were like, whoa. You know, when you have that moment of like, okay. ding ding ding yeah the universe is giving me a gift right now so maybe for context um my friend writes like hey are you hiring are you looking for any superstars and I wasn't hiring because I didn't think I had enough money to hire anyone and honestly I was so friggin burned out and I was so burning the candle at both ends that it was like I couldn't even comprehend the idea of hiring even though I knew I needed more help and I was like uh let me meet her like who is she And then when you and I connected via email, I'm like, I don't even know who you are, what you do, but just tell me, like, give me a paragraph or something so I can understand.

4:53And I remember the email that you sent back. And this is like a great sign for anyone who's thinking about, like, are you going to meet with someone? Are they worth your time? All that good stuff. Can there be a love match there? Tana, your email back about what you did in your historic career and like what you were interested in. And everything in my body was like a frigging hell yes. I'm like, this is exactly who I need to meet. And I didn't know anything else. I had no idea of salary requirement. My mind wasn't even to all that yet. I'm just like, can you come to New York? Are you willing to consult with me for a day or two?

5:28Let's just get to know each other and then see what unfolds from there. And it's so funny because nowadays it's really hard for me to picture you doing something like that. So I think there was just this cosmic connection that I just happened to be figuring things out at that time. We met. Our friend connected us. And you came to New York. I was like, sure. Yeah. So I flew Tana to New York. And I didn't know what the hell that we would do for over two days. But all I knew is I had a ton of potential. I had a ton of dreams, a ton of ideas for, like, products and services that I wanted to create.

6:00And no idea how to make all of that happen and continue to do all the things I was already doing. without cloning myself. Do you know what I mean? It was like, AI did not exist at that point. By the way, y 'all, so she's from California and she comes to New York City and we had had this like really great breakfast in the West Village. And then she was staying in this Airbnb in the West Village, not far from my house. And we were like starting this planning session where she was helping me get all of my ideas kind of out of my head and onto paper to understand like where I was spending my time, where the money was coming in and the business, like all the stuff was so fun.

6:34and then a earthquake happened. Like, when does that ever happen in New York? And for me, I was like, whatever. Yeah, this happens all the time. Everything was rumbling and shaking. And I was like, this never happens. But it was fun. But anyway, so one day went by and we were going to do two days of planning together. And I remember at the end of one day, I was like, oh my God, this is my person. Like, this is my person. But here's where it's so effed up. You had already taken another job with someone else, but it hadn't started yet. Right. So we got along great. And that was actually part of the win for me is that there was no expectation.

7:13It was just like, here, I have this skill set. It seems to be really aligned with what you need. I'm just going to give you everything I got and let's see how far we can get in two days. Totally. I was like so smitten. I was like, I cannot not imagine working with this person. And so, you know, this is like one of my methodologies. Like I'm a woo person. I love when you do not quit. I do not something you go for. I love like a friggin bulldog. Right. I mean, that's why I wrote the book. I was like, I am relentless in it. I did this with Josh, actually, which that's a whole conversation for another day.

7:50But I was like, nope, him. I was like, I don't care what it friggin takes. Like that is my human. And I was aggressive, like, you know, not in a bad way, but just in a really transparent way. I think I did the same thing with you, but I did have a wooing method. So I took Tana out to like a really great Italian restaurant in the West Village. We polished off one bottle of wine and a great meal. And then I was like, are you down to keep going? And she was like, am I down? Like, let's roll. Yeah. It was so then we went to this other great Italian restaurant called Aria, which has since moved. But over now, our second bottle of wine, we started crafting all of these evil schemes, and they're not evil at all.

8:31They were super fun. We were talking about all these opportunities, and I just laid it out on the table. I was like, I want to work with you. I know you have this other thing, but I'm going to be bold. I don't think you actually really want to do that. I don't think that's the right fit. I think this is the right fit. This is your home. It's all up to you, whatever you feel in your bones, but this is what I feel. And I just was unabashed. Well, Well, I think that's a lesson, too, is just like if you really, really want something, just be bold. Yeah. What do you have to lose? Like in that moment, what did you have to lose?

9:00We were already cool with each other. We were tight. No matter what happened. There's nothing wrong with you saying what you want. Yeah. And I even said, I was like, look, I don't want to be a total dick to this other company that you said yes to. I said, but you haven't even started yet. So you go home. You think on it. You sleep on it. You see what you genuinely feel. Because I am 100 % clear. I'm like so certain. And then honestly, the choice is up to you. Like you have a huge opportunity here. This offer is not going anywhere. But I'm telling you, I want this to happen. And now the ball is in your court.

9:32So I just left it with Tana. I was like, you're going home. Just keep me posted and let me know either way if it is or it ain't. Yeah, it's funny. My first impression of you was just like, I like this person. She cool, right? And it's funny because we actually had met years before at a tiny little event in LA. and it was just a blip of a little meeting. And so I knew who you were, but I wasn't super in your world at all. Yeah. And so just looking back now, it's so funny because I don't think either one of us now in this day and age would have taken the risk that we did then, but it seems so normal and like, okay, sure, why not at that point?

10:08But yeah, my first impression was just like, you're a cool girl. Like we just get along and I could instantly be myself and it felt like you were instantly yourself, which is really comfortable. Was that shocking when we were at Aria and it was like, I know it was a couple of bottles in, but when I was just like, I want to work with you, like, was it coming on? Were you like, holy, she's aggressive or no? Or did it feel comfortable? It felt normal and natural. And I think that that's a good sign. Right. I mean, I think we all have instincts. And and if something does feel aggressive, you're like, oh, and you want to take a step back.

10:39But if you listen to your body and you're like, oh, yeah, yeah, yeah, yeah. If you if you are leaning into something right instead of being stepping back, that's a good sign that it's something worth exploring. Yeah. So cut to is like a couple of weeks later. And, you know, we had kept in touch or whatever. And I remember I was actually out at our place in SAG. And I get this. First of all, I called my accountant because I knew I had a feeling that you were going to be like, maybe. and I called my accountant to see if I could make her what I felt like was a really strong offer at that time so that you would feel safe and that you knew it was real and legitimate.

11:19And he was like, yeah, you can totally afford to do this. I was like, okay, thank God. And then I remember I talked to you and I felt like, and correct me if I remember this wrong, but you were like, is this real? Like, are you, are you a hundred percent? And there's a chance. Yeah. Like, are you like everything that we talked about over two bottles? Is that still? And I was like, Like it is 100 % a solid offer right now. It's still there. It's like, let's go. Like if you're ready to do this, it's like we start whenever you want to start. And I feel like I remember being on my deck in my bare feet and I was like jumping up and down and the sun was shining like, yes, yes, yes.

11:53Like I was so pretty. And same, over in Cali, I'm just like, okay, well, there's a change. Yes. I didn't expect that one. Yeah. Yeah. So that's how this whole thing started back in 2011. You had a successful business already, but there was so much potential to take it further. That was untapped. Yeah. And I think that that's actually a great time for other business owners to tap into where they're at. And if they're feeling overwhelmed, but there is, you know, a business that's happening and it's making money and it's helping people, then that could be a time to hire someone with a different set of skills to help you take it to the next level.

12:30Well, let's talk about that because I knew very clearly that, and by the way, I knew very clearly that I was incapable of taking it further on my own. So that was very clear to me. And I also was becoming so clear on the fact that I was like, my God, like I know I have gifts, but there's this whole other thing that's needed that I am so shitty at, that I'm not good at. Like the organization and saying no and like packaging things. And I was just like, oh, like, you know, it was it was and it kept feeding into this insecurity that I think I've had probably my whole life, which was not feeling smart enough, not feeling smart enough and always feeling like, especially as a business owner, I always kind of felt out of place because I don't I have a business degree, but not an MBA.

13:13You know, I just have a bachelor. And and I just always felt like I didn't like I didn't belong because I didn't have that fancy degree. And, you know, I never went for venture capital. I never got investment. I don't know. I don't know anything about that world. So I just kept thinking to myself, I was like, maybe I'm not meant to be an entrepreneur because it seems like I can't handle this. It seems like I can't get it beyond where I got it. rather than just stepping back and being like, dude, you just need more help. And you need someone with a complementary skill set that can use their genius zones and their gifts and you can stay in yours.

13:45Well, I think that's something important for people to understand, too. I think it's our natural human instinct to want to hire people just like us. And I think that there are instances where there's elements that make sense, right? So when you and I got together that first time, we had a ton of fun and we obviously got along. I think that's really important. Yeah. You got to jive with the person. Yeah. And I think that element of having fun is really important to us as people, as friends, and also, you know, running a business. We want it to be fun as often as possible. But I think playing into hiring people that have complementary skill sets, like maybe you have some of the same.

14:24You don't have to, but you, in order to grow, you need to hire people that are different than you. But the key thing you do have to be aligned on are your values. And I think that you should share some of that, right? Yeah. So I think one of the things that I loved about T-Bird when we first got together, and I love talking about money, right? First of all, I love money and I love talking about it, especially with people that I trust. So when Tana and I first started talking about all the potential from a revenue and profit perspective, I knew I was sitting on a gold mine with this business. And we just started talking about money and what's possible, where to spend it, how we feel about it.

14:59And instantly I could tell that you treated money the same way I did and that you and I were so aligned on our value system in terms of where is it important to spend and where is it important to save and how to take risks. And it actually reminded me a lot about my relationship with Josh because we have very, very similar values when it comes with money. We don't think about it exactly the same, but we're totally aligned on what's important to spend on, what's not important to spend on. And even though we don't mix money, like we have shared expenses, but we don't blend our bank accounts, we're so aligned.

15:35And I think it's been a huge part of why we've been together. And I think it's a huge part of why our working relationship in the business is so easy because you have to have values alignment, especially with the people that you allow into the deepest, most intimate parts of your business and that you trust with the money. Because otherwise, it's a freaking nightmare. Like scary. It's scary. It can take the whole ship down. Right. Before you came on board, I had worked with different freelancers and different assistants. And again, I was doing the best that I could with my understanding and my capability at that time.

16:12And so before you came around, you know, I had had this like pretty high ticket adventure mastermind, right? And so this is very expensive. I think it was anywhere between 20 and$25 ,000 a year in terms of what the investment was for that experience. And it was awesome. And a person that I was working with, who was setting up all of the kind of back end, so was in charge of all of the payments and stuff. And you have to understand at that time, I was so busy coaching, delivering, writing the content, like doing all of the things to actually outwardly make the business run and take care of our audience and my clients that I assumed that everything was okay.

16:56And this is actually a testament also to about money. I don't spend a lot of money in my life and in our business. I'm always like trying to keep things nice and lean and we invest where it makes sense, but I don't, you know, I value it greatly. And so I remember like feeling like something was off and I was like, wait a minute, I feel like something's not right. And I dug deeper. I talked to my accountant and I ran the numbers and it turned out that someone that was on my team didn't do the right thing when it came to the back end. And it created a 200 over a$250 ,000 loss, like a quarter million dollars.

17:38And I just remember the moment that I did the math and I saw that. And all that did T was feed into this already insecure part of myself that I suck at this, that I must be like the shittiest entrepreneur on the planet because like, okay, I was able to generate or do you know what I mean? And my customers were happy and the client, like everybody was happy, but like, I am such a f*** up because that happened on my watch. And it was a really painful experience. But especially at that time, I mean, look, a quarter million dollars is always that's a ton of money anytime, anyplace. And at that particular point in the business, I was like, it was 10 times even more significant than it would be now.

18:24And I just remember that feeling like, oh, my gosh, this person didn't pay attention to the details. And they weren't checking the back end often enough to catch it early enough, if that makes any kind of sense. And so I just remembered your attention to detail, even like the follow up from our meeting, like there wasn't a note that you missed. There wasn't an aspect of anything that we discussed that you didn't recap. There were things that you caught on to and that you mentioned that was like, I didn't even remember I said that, but you had it in your mind. And I was like, details matter, dude.

18:52Well, I think details matter too. And for people that really care about what they're doing, it just becomes like, oh, well, of course I care. Of course I'm going to pay attention. Of course, I'm going to follow up. And I think that that's an important part when people are looking to hire is like, try to hire people who you can't really tell, right? I mean, we've made lots. Oh my God, we've made so many hire mistakes. But I want to talk about this because we talked about this actually just before, which is so freaking great. And like one of the things that I pay the closest attention to, and I know you do too.

19:25So we had tons of applications and over the years now, God, I must have hundreds, if not thousands of applications for people to work with. And one of the biggest things I look for is like, did you answer all of the questions in the application? And you would be frigging shocked at how many people f***ed up the first part. They leave like, and there's not many. It's not like there's a thousand questions. It's like six or something like that. And they're pretty detailed. Or they call me Maria. And I'm like, are you f***ing kidding me? It's like people that even pay me a lot of money. I'm like, how are you still calling me?

19:59All right. You're still sending me big checks, but seriously, get the details right. And that's probably one of the biggest things. If like I, if your first impression is you're not getting the details right and you want me to pay you and trust you with my brand, it's, it's a non-starter. Makes sense. Yeah. And I mean, I make mistakes all the time. Just to be clear, I f***ed it up. I will send stuff to my friends. I will send stuff to colleagues. Autocorrect gets my ass every time. And I wind up sending like the face smacking thing and saying, I'm sorry. I remember it was just the other day. Actually, we were out someplace and I called a woman, Maria, who was married.

20:34I'm like, holy shit, that happens to me all the time. I am so sorry. But it's like sometimes the applicants are like nobody even owns it. Like, oh my God, I just sent this. I'm so sorry. It was autocorrect or I didn't realize I didn't catch it. It was just like, they don't care about the details. Yeah. I think another thing we were talking about this week is there's one thing in particular that is the number one thing we look for when we're hiring. And it's the number one thing we tell people when they're onboarding us. It's this one trait that's so important to us. I think you should talk about it.

21:03It's the most important trait ever if you want to hire A players and people need to show up like this. And that number one trait is resourcefulness. I wrote the book, Everything is Figureoutable. It's like in business, 99 % of what you and your team will need to do to grow the business is going to be things that you've never done before, right? Because all the shit you've already done has gotten you to where you are. And now if you want to get to where you want to go, you got to innovate, you've got to take risks, you got to figure new things out, you're going to have to experiment, you're going to have to go outside of your comfort zone into your discomfort zone in order to reach those new vistas.

21:39And in order to do that, the people on your team might not have that expertise or experience yet. Or you as an entrepreneur, you don't have the experience yet. So you need people around you who are resourceful, who are not going to be like, I don't know. It's like, dude, Google it or get up and figure it out or make some phone calls or whatever. And I swear, I mean, I see this just out on the internet in general. It's like people asking questions of like that you can just easily Google. And if folks don't have that resourcefulness, at least on our team and our call, it's like, you're not going to make it here because I, as a CEO, I'm constantly coming up with new ideas.

22:16We're constantly coming up with new things that we want to try. Like, is this possible? Can we do this? And if you don't have that, everything is figureoutable DNA in your, if that's not like a natural go-to, like, oh, we don't know how to do this, but we're going to figure it out. Like, we're going to go find out. We're going to experiment. It's just, the train's going to leave the station or I'm going to get so frustrated. I just can't be around those people. Bless them. I want them to be happy and at peace and have a wonderful life, but I don't want to work with them. Right. I get it. Yeah.

22:45And especially too, it's like we, I think on our team specifically, like I, I only desire at this point in the game. And at this point in my life, I only want to be around a players. Like I only want to be around people that live into what's possible. And that doesn't mean burning yourself out. And that doesn't mean pushing yourself in a way that's unhealthy or anything like that. But I want to be around people who are like, if we come up with something great and we're like, oh my God, that seems amazing. And we're all like, how the hell do we do that? We're like, let's do it. Like, we're going to go find out.

23:19If someone's like, I don't know. And they're just, it's just like the cock block parade. I'm sorry. I know that's terrible, but it is. It's just like, it's a bunch of Debbie Downers like, I don't think so. It's just constantly pumping the brakes. That's, I can't live like that. Yeah. Another thing that I think just in terms of getting into the juicy content, right, a big reason why you and I get together, we get together fairly often in person, but every October we get together to talk about not only planning for the next year, but we also always have at least one big problem to solve. Oh my God.

23:56There are always problems to solve. Yeah. Always, always, always problems to solve. And so I think it would be fun for us to talk about maybe a story from the past or something, one of the juiciest things we've had to overcome or deal with that people might not know about. Well, I'm just thinking about the shit that goes wrong in a business. Almost everyone I know that is really good at what they do and they've done it for a while and they've reached some level of success that they're really proud of has had the most shit-tastic days that you would never know about. And this may not be what you're thinking of, but I'm just thinking of, you know, there was this time when we had a really big, it was like B-School launch.