Dorie Clark Interview: Strategies of a Successful Entrepreneur

If almost everyone thinks something's important, if almost no one is doing it, first of all, congratulations. Because if you do, it means you have a massive competitive advantage over other people. If we're talking about a growth edge for you and your business, actually carving out time and getting good at strategic thinking and long term thinking is one of the very best investments you can make in your business.

Today we're talking to Dorie Clark. She's been described by the New York Times as an expert at self reinvention and helping others make positive changes in their lives. And that's exactly what she's here to do for you and your business. This is the Launch your Business podcast because we know starting a business is challenging, but it doesn't have to be confusing. Each week we'll give you the tactical advice and the necessary tools to scale your business with without feeling burnt out. I'm Terry Rice, business development consultant and staff writer here at Entrepreneur Magazine. Let's dive in. Today's episode is brought to you by chatterboss, a company that provides entrepreneurs with top notch executive assistance so you can make more money, save time and avoid burnout. Get started today and save $50 off your first month by heading to chatterboss.com launch that's chatterboss.com backslash launch. When I first started my business, I charged a client $250 a month to run their Facebook campaigns. $250. Now keep in mind, I had just left my job at Facebook, so why would I charge so little? Well, I had no clue how to run a business and I just wanted someone to say yes. But here's where things really get interesting. Two months later, another company that was based in Long island offered me $20,000 a month to run their campaigns. I said no. I turned down the offer. So you might be thinking, why would this guy take $250 a month but turn down $20,000? It's because I read a book written by Dorie Clark, reinventing Define youe Brand, Imagine youe Future. And the future I imagine didn't involve commuting from Brooklyn to Long island every day. It would have been about 90 minutes each way. And one reason I started my business was to spend more time with my family. So that just wouldn't work. But beyond that, the job just seemed super boring. And it would take up so much time that I wouldn't be able to work on more interesting projects. Not that people were beating down my door to offering these projects, but I didn't want to lose the ability to say yes if they did. About a year later, I finally made over $20,000 in one month. And I was able to do so on my own terms. I played the long game and it all worked out. So that's what we're talking about today. And we're joined by Dori Clark. She's an executive coach, professor at Duke University, keynote speaker, and the author of several books. And her latest is the Long how to Be a Long Term Thinker in a Short Term World. I know she's going to help you, just like she helped me. In this conversation, we'll discuss the advantages of being strategically patient, how to form a powerful network, why you absolutely must make time for white space, and how to keep moving forward even when you're faced with adversity. Let's hop into the conversation right now.

The Long Game is basically a book about how the subtitle is how to Be a Long Term Thinker in a Short Term World. And ultimately it is about how to apply the lens of strategic thinking on your life and your business and your career when it comes to playing the long game. One of the concepts that I actually talk about in the book is what I call thinking in waves. And what I mean by this is that we have to recognize that there are seasons that all of us need to follow. You can't keep doing the same thing all the time and assuming that that's going to work in any of us who's who've tried marketing, for instance, right. You know, people are like, oh yeah, well, Facebook ads are it. Do Facebook ads. And then, you know, everybody's doing Facebook ads and all of a sudden, wait, it's not working anymore. You can't keep doing the same thing and just assuming, oh yeah, magic will happen. You need to learn when and how to shift strategies. And so if you are early in your entrepreneurial journey, you're exactly right, Terry. The thing you need to do is get clients now, and that is knocking on doors, literally or metaphorically, talking with prospects and getting business in the door. It's all about sales. But ultimately a major mistake that I see a lot of entrepreneurs make is that they keep up with that. That's great. If you're going to have a successful business, do you. Doing sales all the time is amazing, but it becomes a problem if you keep doing it for a really long time and you neglect marketing. And the reason for that is that sales often is not incredibly scalable because the people you know, they might refer you, but they know people like themselves. And if you want to grow exponentially rather than just incrementally. You need marketing in order to expose yourself and your business to a new audience. So over time, as we're thinking in waves, early on, you over index on sales, but eventually you need to level up your marketing as well so that you can grow your business for the long term.

Yeah, and that's a really good point because what I found is that often when you first start a business, you get a lot of clients through referrals. And that's great, right? You tell your network, hey, I have this new thing, they come flooding in and you're so busy working in your business, you don't work on, on your business. And then six or nine months later you're like, wait, I don't know how to do sales or marketing because everyone knows my cousin. Right? So I'm glad you brought that up. And you also just need time to, to think because we're so busy doing, doing, doing, you don't have time to be present and just to, just to think strategically. And, and you mentioned this in your book and I don't want to butcher the stats, but these executives in this study said strategic thinking is responsible for like 97% of my success. But 96 said they don't do it or they don't do it often enough. So can you just confirm those stats and unpack the need for making that white space for strategic thinking?

You're exactly right. 96% said they just don't have time to do it, which obviously, you know, strikes, strikes almost all of us on the surface as being pretty problematic. So if, if almost everyone thinks something's important, if almost no one is doing it, first of all, congratulations, because if you do, it means you have a massive competitive advantage over other people. So this is really, if we're talking about a growth edge for you and your business. Actually carving out time and getting good at strategic thinking and long term thinking is one of the very best investments you can make in your business. So a point that I like to make in the long game, it's not that it takes huge amounts of time. Like, let's be clear, I don't have time for strategic thinking does not mean, oh wow, I wish I could take a year off and go meditate because then after the ashram, I would be enlightened. No one has time for that. That is not what we mean. It's just a little time. Right? We need just enough distance and breathing room so that we actually can ask ourselves the right questions, including, should I actually be doing this task, Am I doing the right things to get me to the goals that I want to reach? Is there perhaps a more efficient way to try this? Could I try some something else? Could I outsource this? Could I delegate it? Does it need to be done? If we ask ourselves those questions periodically, we can actually get where we want to go a heck of a lot faster. But most of us are so overbooked and over scheduled, we never even have a breath to do that.

Okay, let's stick with those questions to ask because here's where it gets interesting. Your network is your net worth, right? I'm using air quotes. So it can be challenging to turn down opportunities to connect with people because you never know what can happen. And it can lead to fear of missing out or fomo. Now that's actually wired into our brains because back in the stone ages, being part of a community is how you got access to food and protection. So without it, you're out there fighting saber tooth tigers or whatever by yourself. Now, fortunately, the stakes aren't necessarily as high these days, but it sure can feel like the survival of your business is dependent on who you know. So it can be hard to turn down those virtual or in person coffee meetups. Now, I normally filter out opportunities by saying, well, what do you want to connect about? You know, what made you reach out? But can you just pass on more advice on how to protect that white space but still give yourself opportunity to expand your network?

Yeah, absolutely. And you're right to home in on asking more strategic questions. Right. Early on, when I, you know, when I was like young and early in my career, I didn't have a lot going on. And so literally, if anyone was like, hey, let's have a networking meeting, I'm like, that's so exciting. Yeah, you know, and I was just say yes to everything. But I think it's really important to be explicit if we are still following that strategy of like, hey, anytime anyone says let's do something, if we're still following that when we're five years, when we're 10 years into our career, when we're, God Forbid, when we're 20 years into our career, that is a recipe for disaster. Because what we need to do, much like as we think about thinking in waves, much like as early entrepreneurs, we need to do a lot of sales, but over time ratchet up our marketing so that we're speaking to new audiences. What we need to do in terms of our own time management is early on we need to say yes to everything. Hey, why not? We can meet some people, we can learn some things, but over time, we need to decrease the yeses and increase the nos. Because ultimately, what we are judged on, what our success is judged on, I can tell you, it's not the number of coffees, it's not the number of emails, it's not the number of brain picking zoom calls. It is the projects that we independently create and execute on. And so we need to be protecting that time and guarding it. So our criteria need to tighten. So a big one, as you say, is just sort of asking more information. You can actually weed out probably 50 to 75% of the people looking to do something because they haven't actually put a lot of thought into it. They might misconstrue what it is you do. They might actually have, I will call it a nefarious agenda that they don't want to tell you. You know, so, like, gosh, you know, why do you want to meet? Well, if the answer is, well, I want you to give me money, they're probably not going to say it, so what are they going to do? They're just gonna. They're gonna go away. So that's actually what we want. We want to scare away the people with bad intentions or not useful intentions, because we want the good people, the people that are willing to make the effort, the people that truly want to connect with us. We want to make it easier for them to get in and harder for everybody else to get in.

Okay, we're gonna take a quick break, and when we come back, Dory's gonna answer an extremely important question. To win the long game, what should you be focusing on? Let's take a quick moment here to talk about Chatterboss. Chatterboss is a company that helps entrepreneurs make more money, save time, and avoid burnout by providing top notch executive assistance. And I got to tell you, I've been using the service for the past several months now, and I have no idea how I got by without them before. My assistant, Megan handles everything from prepping my newsletter, designing social media posts, sending out invoices, and even finding local activities for my four kids. But here's one of the most important things. She's not just an order taker. She's also a thought partner who presents new ideas and even challenges. Some of my bad ones. But here's what makes Chatterboss as a company so unique. You have one assistant who can handle your entire remote team. This includes other specialists within the Chatterboss network, as well as Independent experts that can be found elsewhere. But either way, you have one point of contact who knows you, your business and can anticipate your needs while you're focusing on other high impact activities. Get started today and save $50 off your first month by heading to chatterboss.com launch that's chatterboss.com launch okay, we're back and we're talking to Dori Clark. She's a best selling author, consultant and executive coach. And we're talking about the need for white space so you can do more strategic thinking. White space is essential to the success of your business. If you're too busy doing stuff all the time, you won't be able to just exist and think about the powerful actions you can take to grow your business over time. We also talked about the need to remove distractions so we can focus on impact. The goal here or one of the goals here is to be able to focus more. And focusing is harder than filtering. You can easily filter out a horrible idea, but the big thing about focusing is the ability to say no. This is what's really important to me. And you have to say no to everything else, even some really good ideas, some really good opportunities, even if they're revenue generating because you care more about the long term, not the short term. So you might be asking yourself, well, what should I focus on? Dori's going to answer that right now.

Yeah. So when it comes to figuring out where we want to focus and how, how all this works, and there's a few principles that we can keep in mind. I mean, one that I think is really useful is something that I talk about in the long game, which I call optimized for interesting and kind of, you know, a little rule of thumb that we can use. Years ago I made a documentary film and the, it was an environmental documentary and the Heroine was this 80something woman who years before had helped successfully lead the cleanup of one of America's most polluted rivers. And she was, you know, we were doing these early interviews with her about her life and what shaped her life and she was telling the story about when she was heading off to college and her mother's advice to her. And her mother said, whenever you have a choice of what to do, pick the more interesting option. And I thought, oh well that's, that's helpful. Yes. Like, you know, let's, let's try that. Because sometimes, you know, you really are in a situation where it's like, well, where, you know, where should I vacation? Should I vacation in the place that like my family has gone every year for the past five years, or should I try something new and see, see what happens and see what we learn and see what we discover? Or oh, I have a chance to see, to go to the movies or I have a chance to see a Broadway show. What should I do that can be.

A helpful lens, optimize for Interesting. I like this approach because it gives you the freedom to explore different paths, but without the risk of being bored. And along those lines of trying something different. Online courses is something that a lot of knowledge based entrepreneurs consider. I know I've done it and it's not easy. It takes time to create an outline, record the content. I actually self recorded my content during the pandemic and after four hours of recording, that's when I realized my microphone was not plugged in. So I had to be patient. And in your book you talk about the concept of strategic patience, which I'm guessing came in handy for you since I know it took you a while to get traction with your online courses as well. I remember looking at your website for one of your courses and it said over 300 students have taken this course. And I was like, that's it. So I do appreciate your honesty there, but can you just unpack what you mean by strategic patience and how it can be applied to a new business venture?

Yeah, it's a great question. So basically what you're referring to is I actually started experimenting with online courses in 2014 and I did my first course then with a different partner, sort of educational partner. And you know, early on I, there was so much I didn't know. I'm like, how do I put this together? Like, how does this work? I don't know about the marketing. There were a million things. But my attitude early on was, okay, I'm just going to experiment and I'm going to learn. I'm going to do it with an entity because I want to understand and kind of, you know, like almost apprentice. Like I want to learn under their tutelage how to structure something like this. And so in 2014 I made one online course. In 2015 I made another online course with a different partner. And you know, I have to say for each of these courses, like, I mean they took, they took hours. Like the one that I made in 2014, I had to like fly across the country to do it. I was, it was, I think 12 hours of live in front of a camera instruction. I mean it was, it was enormous. And of course you have to prepare for all of that. And, and within a few years afterwards, I had, you know, for each of these courses, made a couple thousand bucks. I mean, it was just like completely a bust, you could say. I mean, it's like, okay, it's not nothing, but for the amount of effort that it was, it just was like preposterous. But one of the themes that I really sound a lot in the long game is that it's about times at bat. You need to be trying lots of different things. And so the crucial thing was that for seven years now, I have been learning about online courses and all the different, you know, ups and downs and variables and, you know, what I liked and what I didn't like. And so those particular things, they've never been especially lucrative. I mean, one of them now has probably brought in about ten grand over a seven year period. I mean, I'm grateful for it. But again, it was a lot of effort and a lot of time to do that. But what it did was that learning enabled me to try other things. And so in 2016, I started launching my own online course. And I now had, you know, on the sort of the backs of other people and working with them. I had learned enough that I'm like, oh yeah, I'll try it for myself. And I ended up launching my flagship course, which is called Recognized Expert. And over the past five years that's brought in well over a million dollars. And you know, this is money that, you know, it's not with a partner, I'm able to access it, which is fantastic. I would never have been able to do it if I hadn't done the kind of unsuccessful ones before. And as you're alluding to, Terry, I am a big fan. This was actually the topic of my previous book, Entrepreneurial you, about creating multiple revenue streams in your business. I'm a big fan of diversification because we just do not know what's coming down the pike. I used to make a ton of money from keynote speaking. I was traveling every week, every other week, probably 30 to 50 keynote talks per year that, as you might imagine, completely evaporated during COVID But also interest in online courses shot through the roof. And so I had the most successful launch ever for the Recognized Expert program because of that groundwork having been laid.

Right. And in regard to online courses, I already talked about my experience forgetting to plug my mic in. But in my head I was thinking, well, at least I get more practice and it will be even better when I actually turn my mic on. And fortunately it was, but you know, it still was a bit of a bummer because every time I left to record, my wife had to watch all of our kids. So I came home after being gone for several hours with nothing to show for it. And, you know, I get it. That's all part of playing the long game. And luckily, she's super patient. But what advice would you give to people in regard to experiencing these setbacks?

We all, you know, on the entrepreneurial journey have tons, tons of setbacks. Right? I mean, I wish we didn't. That's the thing. You know, you asked earlier about strategic patience, which is a concept that I talk about in the long game. I wish we didn't have to be patient. That would be so nice if we could just, like, get all the things. It is not that I am valorizing things taking a long time. I am not. I would much rather they happen quickly, but just the reality is that they often take a long time. And so if we want to deal with that, rather than, you know, just being like, you know, negative jerks that no one wants to be around, we have to find a way to reconcile ourselves to the. That things take a while. And that is where strategic patience comes in for me. You know, when. When you hear the advice, you know, the kind of like, mom advice, but like, just be patient. So often to me, with that connoted was just like, you know, pat you on the head. Like, just sit back, it'll be okay. Just work hard. It'll take care of itself. And I'm like, no, it won't. Like, that's not, you know, like, how do you know that I don't know that, you know, like, I want to do something. And so strategic patience is about placing little bets and watching them and monitoring them. It's not like you just sit back on your barca lounger and let life come to you. That's not how life works. You place a bet, you put your money down, you see what happens, and then you adjust and you pivot as necessary. I think that's really what we need is patience with an understanding. Okay, this might take a while, but I'm going to watch this thing and I'm going to make sure that. That it's heading in the direction that I want. So how do we stay resilient? How do we come back if we're having setbacks? And I'll say, as you saw, Terry, I have an entire chapter in the book where I talk about specifically for me, because I wanted to put this out there no matter where you are in your career. I mean, this is now like my fourth book. I've done plenty of stuff, but I continue to get rejected all the time. It's just you kind of get rejected by better and better things. But I mean, that's like Cold comfort. Like, oh, good, I got rejected by a real class A operation. And so I write about, you know, like in 2019. So pre. Pre Covid all these rejections. There was this major media outlet I was gonna write for. They put me through a million hoops. Finally, they're just like, no, I was gonna co write a book with a famous author. And in the end, like, no, that didn't work. I was going to. I was hoping to speak at a big conference and they like totally blew me off and never got back to me. You know, all these things. So how do we do it? I think probably the most. There's a lot of ways. But the most important thing, the most important message is that I think too many of us give away our power by assuming that the gatekeepers actually know what they're doing. I think too many of us. If one person says no, we never try again, or we back off, or we say, oh, God, I guess I'm not good enough. I guess that's not going to work. One person telling you no is never enough to back off. There's a million reasons, including just their inbox is too busy or whatever, they had a bad day, that they're saying no to something. It does not mean you're not good enough. Fine, if 100 people tell you no. But if you're giving up after one or two or half a dozen, you have not even started. And it is wrong, it is absolutely wrong to listen to those people and derive some kind of a judgment about yourself.

So one thing you share in your book is that you could be grinding for several years before you hit a big breakthrough. But the cool thing is, once you do, the outcomes aren't linear. They're exponentially better than you could have imagined. And here's a game I like to play, and I'm just wondering if you do the same thing. When I land a big opportunity, maybe it's a paid partnership or a speaking gig. I'll reverse engineer what got me there. Like, why am I here right now? So, for example, I spoke at south by Southwest before, and I'm like, why am I on this stage? How'd I get here? I'm going to reverse engineer it. And it goes back to me being super desperate to land a job teaching at General assembly and back Then I was a WeWork member, and they had this, like, this virtual message board. So I put up a post saying, hey, can someone help me get a job at this company called General Assembly? I want to start teaching there. Here's my resume. And luckily, one random person saw it and was willing to help me out. And she didn't promise me a job, but she promised me a shot at getting in front of the right people. But I got the job. And from there, I taught hundreds of classes. And eventually they're like, hey, do you want to go speak at south by Southwest? But again, it all started with that one person who responded to my random message and took a shot on me. So have you ever done the same thing where you're like, wait, why am I here? You know, how did this even happen?

I love that you did that, Terry. I think that's so smart. And I really would encourage everybody to do it because it helps you understand. You know, this is very much like, you know, the butterfly, you know, flapping the wings, right? And, you know, creates the monsoon. But it's true. And we often just don't recognize it, but it helps us to understand, okay, what are the things we can control? We can't control the outcome, but we can control the process. And so what are the things that we are doing that's putting us in the right zone to receive good opportunities? So, actually, in the long game, I break down kind of a cool thing. This might even be one of the coolest things that I've had the opportunity to experience. I was a producer on a GRA Jazz album that ended up winning two Grammys. And as a result, you know, we're nominated for these Grammys. I got to go to the Grammys. I got to be on stage at the Grammys, helping to accept this award, which is so wild. It's not anything that I had ever anticipated. But so in the book, I actually break down the process of how did I get there? You know, I mean, it's not. It's not like I'm even a jazz musician or anything like that. But it all came from, actually a series of six or seven people through which I had connected to a guy that was the lead producer on the album and then brought me in. So tracing all of it back and where it started again, this is the part you can control is a number of years ago, when I first started writing for a particular publication, I decided, oh, you know, I want to get to know all the other people who write for this publication. Like, these seem like Cool people. This seems like a good, you know, kind of tribe for me to be part of. So I was just reaching out to folks and I had just moved to New York and so there was a guy that I knew lived in New York, and so I sent him a message. I'm like, hey, we both write for this place. Do you want to get coffee? And he was like, okay. And so he got coffee and he literally said, oh, hey, you know, like in two days I'm speaking at this conference and they told me they need another panelist. Do you want to do it? And I was like, okay. Like, I didn't know it. I literally had just moved the city. So I, I went to speak at this, at this panel. And so I met a guy which then led on this chain to me helping be a producer on a Grammy winning jazz album.

All right, I did not think that story was going to end with her winning a Grammy at all. We're going to take a quick break, but when we come back, we'll go deeper into how you can develop a powerful network as well. And who knows, you might just win a Grammy. Just get started. If you've ever looked for tips on launching a business, just get started seems to come up a lot. And while that's vaguely motivational, it does not provide any real direction. Because the next logical question for anyone would be, well, how do I get started? What specifically should I do? Well, if you're looking to quickly start a business without the confusion, risk and pressure of doing something entirely new, I've got a solution for you. It's called the Solopreneur's Fast Track, a step by step process on how to start a business using the skills you already have and actually enjoy using. So let's say your favorite part of a previous job was email marketing. You'll learn how to start a business offering other companies advice on how they can improve their email marketing. Or maybe you are really good at integrating complicated tech tools. You can help other organizations do the same thing without the need to bring on a full time hire. So the main point here is that everything you need to start a business is already within you. You don't need a cool website or fancy tools. And by completing the course, you'll also discover a simpler approach for attracting clients without using complicated funnels or cheesy sales tactics. You can finish it over a weekend and start making money in as little as 30 days. You'll gain the clarity and confidence you need to start your business and receive a one page business plan. So you can immediately apply what you've learned. Get started today and receive a 20% discount by heading to TerryRice co. That's TerryRice co. Fast. We're back with Dori Clark and we left off discussing the need to develop relationships. And I always say the three most powerful things you can share in a business relationship are your knowledge, your network and your ongoing support. But I think too often people focus on what they can take from someone as opposed to what they can create with them or just learn from them. And this may be entirely unintentional, but there will still be negative consequences. Dori is going to enlighten us on how we can avoid that mistake.

Relationships are a key part of your long term right. We are shaped profoundly by the people that we know. And you know, it controls everything. It impacts what we know, it impacts what opportunities we hear about, etc. And so one of the strategies that I propound is something that I call infinite horizon networking. Because, you know, what gives networking a bad name is exactly what you described, right? Like, oh, hey Terry, I see, you know, so and so can you introduce me? And it's like, you know, you're, I call it like sneak attack networking. Like, ah, you know, they, I thought they wanted to be friends and then ah, you know, they got me. But infinite horizon networking is deliberately networking with people that seem useless to you. Let's just put it that way. There are people where you're like, okay, like in a million years would I, would I need anything from this person? I mean, you know, like they're an astronaut and you're a lawyer or something like that, like just completely random. And if you were only operating on the principle of like, who can do something for me? Then you wouldn't talk to them. But number one part, you can actually have a, probably a better relationship with them if there's nothing on the table that they can do for you, quote unquote, because you actually get to know them as a person. Number two, life is long and people's paths tend to kind of converge in weird and different ways that are interesting over time. So you never know. And number three, you actually, your path might change because of them because they are exposing you to new ideas and connections and information that other people in your network are not. And so that's actually precisely the reason that you should be thinking about networking through that infinite horizon lens.

Infinite horizon, that's such a cool name. And you make a good point. If you only hang out with people who are similar to you, it's likely you're voluntarily living in an echo chamber. So before I let you go, I do want to ask you one more question. For anyone out there who's still feeling anxious about their future or caught up with their day to day grind, why is it so important to focus on the long game?

Why is it so important? It is so important, I believe, because there are small actions that we can take today that will make tomorrow. And I say tomorrow, I mean literally, I mean metaphorically, all the tomorrows better and easier. And why wouldn't we do that? It's not about taking some huge onerous hard action. Nobody has time for that. It's about making small strategic shifts so that we can make everything downstream a little easier, a little better. If anyone's interested in like really turning the lens on themselves, go to doryclark.com thelongame you can get a free self assessment and figure out how to be a more long term thinker in your own life, your own career and your own entrepreneurial venture.

So I hope that reinforces why it's so important to play the long game and gives you the tools to do so. And look, I know it's tough, especially when you're in the early stages of your business. But if you'll notice, it all starts with being more present in the current moment. You can make good long term decisions as opposed to being anxious or concerned about the future. And I wish I had learned that lesson sooner because my daughter was a newborn when I first started my business and I missed out on a lot. Now I was there every day but I was constantly distracted because I was so worried about her future. And that's because her future was dependent on success of my business. But in the end it all worked out and within 18 months I was able to make $20,000 in one month without a three hour commute. So if you're ready to start playing the long game, take that assessment on Dory's site. That's doryclark.com Dori the Long Game and I highly recommend reading her books as well. I know she'll help you just like she helped me. Apply what you've learned on today's show. You'll find the show notes and more resources at Terryrice Co. Podcast. Again, that's Terryrice Co Podcast and the best way to support this podcast is by subscribing, telling a friend and leaving a review. Also, you can get more information tips by following me on Instagram terryrice or follow me on LinkedIn. This episode was produced by Josh Wilcox of Brooklyn Podcasting Studio and edited by Dan Lardy. Special thanks to my wife, Dominique, for keeping our kids relatively quiet as I recorded. Thanks again for listening. I'll see you next time.