YFTC 001 | Entrepreneurial Journey

01: Embrace the Entrepreneurial Journey with Dorie Clark

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Dorie Clark is a frequent contributor to the Harvard Business Review, Time and Entrepreneur magazine. She is recognized as a branding expert by the associated press and fortune. She is a marketing strategy consultant and speaker for clients including Google, Microsoft, Yale University, Fidelity, US State Department and the World Bank. She’s also the author of Reinventing You and Stand Out.

Embrace the Entrepreneurial Journey with Dorie Clark

How about if I introduced you to a frequent contributor to the Harvard Business Review, Time, and Entrepreneur Magazine? She is recognized as a branding expert by the Associated Press and Fortune. She is a marketing strategy consultant and speaker for clients including Google, Microsoft, Yale University, Fidelity, U.S. State Department, and the World Bank. Dorie, welcome to the show.

Thank you for having me.

YFTC 001 | Entrepreneurial Journey
Entrepreneurial Journey: Reinventing You: Define Your Brand, Imagine Your Future

I love your work. Reinventing You was such a cool book. When I got a hold of that, I said “You’re right. Nobody knows who the heck I am. I got to reinvent myself.” I know some of the work you’re doing. It’s never an easy journey to go from where people see you as an overnight success from the very beginning to have gotten to that point. Like all of the entrepreneurs that I get to speak with who have been successful in the past, they always seem to have a very interesting start. It’s always colorful and interesting, and I can’t wait to hear yours. Tell me about how you got started building your company.  

Eleven years ago, I launched my business. Part of the motivation for that was that I was a nonprofit executive director immediately prior to becoming a consultant, author, and speaker. I realized during the course of running this little small bicycling advocacy nonprofit that what I was doing, even though I hadn’t really thought about it in these terms, I was running an actual business. I was essentially being an entrepreneur. At a certain point, it hit me, “I could be doing this for myself.” I spent another year after having that revelation continuing to serve as the ED. I wanted to make sure there was a really good smooth transition into the next leader. I also used that time to continue to build up my skills and read a bunch of books on entrepreneurship and take some classes. That was where the light bulb went off for me. I never thought about starting a business before, but I eventually just realized that I was already doing it and I might as well do it for myself.

How many people are sitting at a job dreaming about that period of time when they might break away from the job and become an entrepreneur in a sense and have their own business? How did you finally make that decision to act on that year of thinking?

Running the nonprofit was probably the most stressful job that I’ve ever had. I say that advisedly, in the sense that the job immediately prior to it was I was working as a presidential campaign spokesperson. That’s high stress. You constantly have the national media coming at you for comments, it’s a 24-hour-a -day job. I remember getting phone calls sometimes at 3:00 AM from reporters that had heard some rumor and they wanted confirmation. We worked seven days a week for months on end, and it was very high intensity and fast paced. Even so, running this little nonprofit was far more stressful to me at an existential level. I was responsible single handedly because my board was not very active with fundraising, for bringing dollars in the door. It was not just me. I was responsible for other staffers, and I took the weight of that very seriously.

The organization, even though it was tiny, had been around for 30 years before me. I would wake up in the middle of the night just so paranoid that somehow I would screw things up and that this organization would collapse because of me and people would lose their jobs. I wasn’t being paid very well for doing it. What really sealed the deal for me was realizing that I had almost infinite upside being an entrepreneur. I It would not be hard for me to be paid more than I was running the nonprofit, and my stress levels would go down exponentially. I felt confident that no matter what I did, I could find a way to not be homeless and I wouldn’t have to be responsible for these other staffers. Many people think entrepreneur ship is risky. For me, it was a lot less risky.

Nonprofit executives are notoriously underpaid. I know that you were supporting your lifestyle when you think it probably didn’t seem stressful. Was it all stressful, or was just such a no brainer? You just said, “I’m leaving.”

In starting my own business, certainly there were stressors. One thing that I did that I would not recommend other people do is that I left my job without any clients in hand. I would recommend other people line up clients first and then depart. I was so paranoid about making sure that I had an orderly transition at the nonprofit. We were just so small and fragile that I gave them six months’ notice. I was much more concerned about leaving well than I was about starting my own business. I certainly was eager to get clients, but I didn’t have any in place before actually leaving the job. It took me two months to get my first clients.

That was a stressful period, when nothing is coming in the door and you’re just not sure how to how to make it work. Another factor that was stressful for most nascent entrepreneurs is learning pricing. If you’re transitioning into an industry that is very similar to what you were doing before working for someone else, then maybe you have a better grasp on it. For me, I had never hired freelance consultants. I didn’t really know what the going rates were, and so I was paranoid about overcharging and that I would get turned down or lose opportunities if I overpriced myself. Meanwhile, you often for years underprice yourself as a consequence. Those pieces were a little bit intimidating for sure.

You knew what you wanted to do though. You were clear about when you left this job, that you were going to offer your services to clients.

I was clear about what I wanted to do, although the caveat is that it changed multiple times in the first few years. I am a believer in iteration and the Lean Startup Method. I went out there and my initial vision was that I would do political consulting. My immediate past job was being a presidential campaign spokesperson. I had previously been a press secretary on a gubernatorial campaign, so I had a lot of experience that was marketable. I went out there, hang my shingle as it were. I realized almost immediately that it was much easier for me to get a nonprofit or government clients as opposed to political campaigns. I had thought I would be purely a political consultant, and then I realized that’s not going to be a good business model, it’s a lot easier to do the other stuff. I reconfigured myself initially from being a political consultant to being a marketing and communications consultant.

The second big switch was that early on, I was mostly doing PR for clients. I had a lot of media contacts because of having worked doing press. I knew all the reporters, I knew how to get people in the papers, and that was a certainly a marketable skill and one that people wanted. At the time that this was happening, which was the mid-2000s, it was an inflection point for two things. One was the rise of social media, the second was the decline of traditional media. What clients wanted and what they still valued was getting on the front page of The Boston Globe, or at least the front page of a section of the Boston Globe. The things that worked even five years before was not happening, because they were not grasping that a third of the reporting staff had been laid off.

There weren’t bodies to go to these things anymore, so the standard of newsworthiness had risen dramatically and the page count had declined. The thing that the clients wanted was no longer available in the same way, and so they were just perennially disappointed no matter how much you tried to set the context. I realized I needed to adapt my business model, because I didn’t want to be in a place where I was constantly disappointing clients even though I was working incredibly hard to do so. I shifted away from straight up PR consulting into doing more marketing consulting even though I had never really done that before.

What is the first thing you started to do? I’ll give you an ABC. A) Ran out and printed business cards and brochures. B) Created a brand new website and all of the auto responder that go with it. C) Got on the phone and started calling people trying to get clients.

The wrong thing to do is to waste a ton of time creating logos or doing all of these ridiculous exercises in branding before you even validate whether you have a business. I actually was decent about that. I certainly didn’t have that knowledge at the time. I wasn’t nearly so schooled in the ways of business literature, but I didn’t have that much savings, and so I knew that I did need to get money in the door somehow. That was how I was able to pivot rapidly from positioning myself as a political consultant to being a communications consultant, based on that market feedback that from those first emails that I sent out to friends and colleagues letting them know that I was starting a business venture. The people who were biting most frequently were people that I had previously worked with who now were running nonprofits or were in charge of government agencies that could requisition some contract. That was where I was able to get my first bit of business.

Sometimes we tend to focus on the wrong things when we get started. Everybody listening to the show probably can tell us about an experience where they did focus on the wrong things. Now that you’re at a point in your career where you’re starting to make solicitations and maybe even signing a few clients, what was that first year like? Was it an instant success and you zoomed up to eight figures overnight, or was a little rougher going than that?

I’d love it if I if I did zoom eight figures immediately or even eight figures now would be would be amazing, but no. I had a plan for myself. I felt like this was a reasonable plan, and I was when I was able to exceed it. My plan was that year one, my goal was not to go bankrupt. Year two, my goal was to make as much money as I had made at my nonprofit, and then year three, was to break six figures. That was that was my plan. Fortunately, I was able to go even faster than that. By my second year in business, I was bringing in six figures and which was dramatic for me. Running the nonprofit, my first year on the job I got $36,000 a year. My second year I got $45,000 a year, which seemed like a big raise, but the truth was I had to bring in all that money. I wasn’t that excited to have a raise, because it was like you can have this money if you somehow figure out how to raise this money. It was more of a burden than anything. I was not living large. To be able as a solopreneur to bring in six figures by my second year at business was definitely a relief to me in doing it.

One thing that I did early on, which is part of the necessary progression but one that you want to move past as rapidly as possible, was the “I can do everything” syndrome. I was intent on getting as many clients in as much experience as possible, I would do any project under the sun that people offered me. I was often wasting time working for clients where ultimately I’d build them $300. A $300-client is great if you have some digital product you can sell them once that requires no marginal costs to create, but everything that I was doing was bespoke consulting. We’d have meetings and prep calls. I was just racing around oftentimes for low margin business and exhausted me.

Let’s go back to year two. It’s not that particularly interesting that you made six figures in year two. It’s the underlying systems you must have put in place to allow that to happen and some of the decisions around how you would then decide what clients to take and what not. Can we talk a little bit about that?

My business model has continued to evolve in it and it looks different even today, but in those earliest days, what I came to realize was one-off engagements were just going to kill me because they involved so much time of courting and getting to know clients. I wanted to get as many retainer ongoing contracts as I could. What enabled me to be able to boost things up was finding some organizations where I could get on a monthly retainer for them. These were relatively low dollar sums in the scheme of things, maybe it was $3,000 a month, maybe it was $4,000 a month, but getting a few of those in place so that I knew that I had guaranteed income coming in. That became a lot of my work, but I continued to hustle on the side to cultivate and do new leads and new contacts and to tip it over six figures.

This must bring you to around 2006, maybe early 2007, where you were working on retainer for some larger organizations and still hustling a bit to try and figure out what else you can do. When did the move that changed it all take place, and what was it? Was it the book? Was it the webinar? What for you shifted things dramatically, and what part of your career did that happen?

Between 2006 when I started my business and early 2009, I was concentrated on getting clients in the door, making money, and trying to build a sustainable business so I felt confident that things could be a going concern over time. Once I got to that place around 2009, that was the financial crisis as well, but by that point I had established enough confidence in my business that I felt like things were going to be fine. In early 2009, I decided that I was going to really focus on trying to take my business to the next level by writing a book. That was something that had been both a personal ambition of mine and also something that I thought would be useful from a branding perspective.

I decided to zero in on that. I spent six months writing three different book proposals. The truth was, the proposals themselves were not the issue. What the issue was that after the crash in 2008, the publishing industry got very timid, and they decided that they were not going to take very many chances on new authors. What they wanted was as close to a sure thing as you could get. What makes something a sure thing is if the author has a preexisting platform, meaning they are already famous on their own and have a built-in audience. That means the publisher doesn’t have to do any work.

YFTC 001 | Entrepreneurial Journey
Entrepreneurial Journey: I decided that I was going to focus on trying to take my business to the next level by writing a book.

I tried to get a publishing deal and I couldn’t because I did not have a sufficient platform. I was frustrated about that, but I figured I’m just going to have to do that. I spent the next eighteen months concentrating on trying to get that platform. That became my new focus. I began trying to break in to various publications as a blogger. That was my vehicle of choice, and eventually I was able to do that.

In late 2010, I started blogging for The Harvard Business Review, and that became the lucky break for me. First I was blogging for them, then they reached out to me and asked me if I would turn one of my blogs into a magazine piece for them.

When the magazine piece came out, I realized that that was the place that literary agents looked for potential clients. I got approached by three different literary agents when my piece in HBR came out, saying, “Have you written a book? Are you interested in writing a book? Are you interested in having me represent you?” I suddenly realize, this is what it feels like when it’s easy. This is what it feels like when the wind is at your back. I was in fact able to turn that article, which is about reinventing your personal brand, into my first book Reinventing You. I sold the contract for it in 2011and it was released in 2013. It took a lot longer than I wanted it to, but it did happen.

It’s interesting how circumstanced drops you in the exact place you’re supposed to be, which I never think about as accidental. My viewpoint is that these things happen exactly as they’re supposed to, but they don’t happen without you getting out there and you doing the work, and clearly you were doing that. The odds of somebody high up at Harvard Business Review asking you to do a magazine piece, that was the wild card, because you didn’t know that that would have done it.

In my own life, I always look for the signs that the universe is giving me, that the next step is right in front of me and then somehow I’m either too oblivious to see it or too busy to see or not focusing enough on what is happening to see it. Luckily, it just showed up that way for you, which was wonderful. Your book went on to be a terrific success. At this point in your business, are you still focused on taking clients or had that shifted?

I was definitely still focused on taking clients. When the book came out, this was 2013, seven years after I started my business, I decided that was the point where I was able to begin to shift my business model a little bit. For the first time, as a result of the credibility that the book generated, I was able to start getting paid for speaking, so that became a new revenue stream. Also the book itself was aimed at the individual market. It was a book about how to reinvent yourself professionally. What I have been doing up to that point was corporate level and enterprise level consulting, and so I started getting a lot more inquiries from people who were interested in private executive coaching.

At first I said no because I wasn’t used to doing that. That wasn’t my model. Eventually, I thought, “This is silly, people are asking for this,” so I began doing that. Today, I’ve begun diversifying proactively my revenue model. I am making money these days from a mix of a little bit of consulting, executive coaching, some adjunct business school teaching, keynote speeches, creating my own online courses, doing some affiliate sales with my email list which I’ve worked on growing. There is a lot of diversification, which I like, because that’s the secret truth of entrepreneurs. We’re actually risk averse.

What you have done is constructed multiple streams of recurring revenue. Even though some of it is passive, some of it is non-passive, which means you need to get out there and perform in order to get paid, but this is the way a true entrepreneur lifestyle can be built. A lot of people who are listening to the show are somewhere between their first and second possibly and third type of recurring revenue or business model. You said yes to something that you were uncomfortable doing, and that’s where we get to experience some transitions in our world. It’s by saying yes to those uncomfortable moments. Was it a big deal for you when you started getting these requests to do executive coaching? How did that make you feel? Was it uncomfortable at first?

It was not uncomfortable per se, but it was something that I definitely wasn’t used to. I had not trained for it. Some people have gone to coaching academies. It took me a while to begin to conceptualize exactly how I could help people. The typical ways that people do management coaching was not something that I felt necessarily experienced in or qualified for. I could certainly do a 360-interview or give people feedback on how to be a better leader, but I didn’t think I had better advice than other people about it. It took me some time to realize what my angle could be, where I felt confident that I could help people.

As I began to write and formulate the ideas around my second book, Stand Out, which is about how to become recognized expert in your field, that was when I realized that what I actually could do that was very different than most executive coaches were not counsel people about a better way to relate to your employees, but specifically to provide coaching for people about how they can become thought leaders in their field. That is something that a typical management consultant or an executive coach does not do. It was something that I felt both based on the process of writing Stand Out and my own experience fighting my way to increased prominence was something that I thought I could legitimately help people with.

People are sold a bill of goods when they are sold a coaching certificate. Coaching certificates are good only after you’ve had the experience of building or growing a business or a life, if that’s what you’re coaching on, and then later putting some structure around it with a course or with a program. Unfortunately, people are brought into these programs and they’re told to ask silly questions at times when they’re supposed to ask them, but because they’ve never been there, they’re not successful, which is why the average income of coaches in this country is below the poverty line.

What I hear you doing and what most of those of us that are successful with this are doing is we focus on what we did and what worked for us and forget about the process itself, allow other people to become part of our world, and hopefully our biggest benefit is in helping them do what we now know how to do. Here you are, you’re past that 1,000 clients and you’re doing all these cool things and you’re showing up on people’s stages. I’ve seen you speak live. How does that work? How does somebody who wants to be a speaker get out there and find speaking gigs?

In almost all cases, you don’t find speaking gigs, at least if we’re talking about paid speaking gigs. They find you. It is true that cold calling and pitching yourself can work, but the hit rate is almost improbably low. It’s just vanishingly small. If that’s the best way legitimately for you to spend your time, then great, but for most professionals that are running businesses, there’s a lot better ways that you can spend your time than just aimlessly calling people. For almost every speaking engagement that I’ve had, it comes about in one of two ways. One is that you have a warm lead. That warm lead may be someone who is on the board of an association that can recommend you. Maybe it is a past speaker in an event that will suggest you.

You can ask that person to recommend you. That will often turn the dial in a positive way.

The other alternative that has worked for me is creating content or somehow making yourself visible so that the organizers of these events come to you and find you. In this weird and warped way, it’s important for the organizers of the event to feel that they are making the choice, that it’s not just someone’s throwing themselves at the organizer and the organizer says, “You’re just what we’re looking for.” They want to be choosing. If they feel that they are choosing you based on some article that you’ve written or video you’ve made, that is so much more powerful and so much more valuable and enables you to name your price and all the things that you would want to do as a speaker.

I would like to go back to and focus on systems. It’s a mistake that many of us make when we start out to either go overboard and build crazy systems, or don’t have any. Would you mind telling us a little bit about the systems that evolved for you and what you do today?

Systems are critically important. Probably the biggest system that I have in place is guided by the principles laid out in an essay by a gentleman named Paul Graham who is the founder of the famed Y Combinatory in Silicon Valley. He wrote an essay called The Manager’s Schedule Versus the Maker’s Schedule. He lays out what the optimal schedule is for two types of functions. The manager is in charge of a bunch projects. For that person, you need to be having meetings and phone calls all the time because you need to stay on top of what’s happening. You need to answer questions, you need to uncover hidden roadblocks, you need to make sure the wheels are turning. That person will probably have every hour a different phone call or meeting, just to keep the wheels turning.

Meanwhile, there are the makers. The makers are the people who are expected to create stuff. In the world of Silicon Valley, that’s usually engineers who are doing programming, an author, someone who’s having to do a creative project like writing a book, or maybe it’s a blogger, anything that that requires sustained focus where you really have to create something. It could even be a speech or a presentation. If you try to do that in half-hour-long increments, you are probably going to fail miserably because your flow gets interrupted by all of these problems. You might look at your schedule and say, “I have all these blocks in between my five meetings.” No you don’t. It doesn’t work that way.

What I try to do religiously is schedule what I call manager days and maker days. I strive to protect my schedule where I have nothing on the schedule until evening if I have social plans. It’s during those days I’m able to really immerse myself in depth in the meaningful creative processes that enable me to make legitimate long-term progress on something. The other days, fine. If I have a phone call, I can do emails around the phone call. That doesn’t take a lot of brain power. If I’m actually going to be writing the outline for my next book, that takes a lot of brainpower. You need to carve out and protect time for that, otherwise you really run into trouble.

This is the mindset issue that a lot of us as entrepreneurs don’t quite get. You have articulated it so perfectly and so beautifully. It’s a time management skill that is more focus management as well as time management. I do set aside hold days to do nothing but work on my content. In other days, I’m booked solid almost hour to hour with phone calls and interviews and strategy sessions. It’s so important for people to get the fact that these things need to be in separate places so that you could be best at both. Next thing I want to ask you about is your passion. I know that you’re passionate about your business, but is there anything else that is your passion today, something that you’re excited about, maybe a new book or some other project? 

YFTC 001 | Entrepreneurial Journey
Entrepreneurial Journey: Entrepreneurial You: Monetize Your Expertise, Create Multiple Income Streams, and Thrive

I do have some things that are exciting. On the professional front, I have a new book that’s coming. It’s called Entrepreneurial You: Monetize Your Expertise, Create Multiple Income Streams, and Thrive. It’s a book about how people can actually make money as consultants and coaches and entrepreneurs. For a lot of people who are consultants or speakers, they’re making these poverty level wages because they just don’t know how to monetize. This is a book about that process. How do you make money being in business for yourself? I’m hopeful that that would be a tool that is helpful for other folks. I started taking some classes in standup comedy, and that’s been really fun. I’ve done a number of performances here in New York and that’s been a terrific creative outlet that I’ve really welcomed.

I don’t know if I have the nerve to stand up on stage and do that, although I used to be a guitar player for a rock band so I do have a little bit of stage experience but it goes back a long way. How do you think you’re doing with the comedy stuff? Are you getting a lot of laughs?

I’m doing well. I have been seeing friendly crowds. I’m working on it. I know from my own experience doing a ton of keynote speaking, now well over 200 keynote speaking engagements over the last few years, that you’re often decent to start and then you see yourself get better. You can see that progress. It’s gratifying for me because I wouldn’t claim to be a perfect self-actualized speaker, but I’ve reached a level of proficiency where I feel good about it. It’s not like I’m improving by leaps and bounds every time because I have achieved a certain degree of mastery over the presentation and the subject matter, but because I’m just so far at the other end of the learning spectrum, you can see rapid progress which is a gratifying process.

It sounds like a fun project and I hope someday I get to see you on stage after you’ve perfected your comedy act. I have one more question. What is it that you are doing or would like to do that truly has the potential to change the world?

Over the course of the books that I’ve written, Reinventing You, Stand Out, and now the new Entrepreneurial You, I think of them as a trilogy. This trilogy is in a lot of ways the entrepreneurial life cycle, but also the life cycle of self-actualization as a business person and as a person who is trying to do something meaningful with your life. The first one, Reinventing You, is about how do you reinvent yourself into the career and into the life that you want? The second book, Stand Out, is about how then you become known as one of the recognized experts in your field. How do you really get people to see your true worth? The third book, the final part of the trilogy with Entrepreneurial You, is how do you get paid for it? How do you make it sustainable and earn a good income that you deserve based on your expertise? By putting these things out there, it’s my hope that it can unlock the potential of a lot of people.

There are people that we know that are very talented, they’re very smart, they’re very good at what they do, and yet they seem to struggle to gain traction in the marketplace as a consultant and entrepreneur or a small business owner because they don’t know how to market themselves. It’s a crowded field. They haven’t necessarily spent as much time getting good at selling themselves as they have doing the thing that they do. What is sad about that is that it means that these ideas and that potential languishes oftentimes. The world doesn’t get to see it or experience it because no one ever hears about it. I would like to give people the tools so that their best ideas can be heard. If we do that, hopefully that leads to a chain reaction that unleashes a lot more potential in the world and makes the world better and also makes life a lot better for the people who are being fulfilled to see their ideas in action.

Making life better one entrepreneur at a time. What a pleasure it was having you. How can people connect with you? Your books Reinventing You and Stand Out are available on Amazon, but is there some way that someone could go to one of your websites and learn more about you or even send you a note?

If they are interested in diving and learning more, go to my website,DorieClark.com. I have more than 400 free articles that I’ve written there for places like Forbes and Harvard Business Review. I have a free resource, which is the Standout Self-Assessment Tool Kit, and that helps professionals walk them through the steps of how to identify your breakthrough idea and build a following around it. If you’re in the process of thinking about getting your first 1,000 clients or even taking it to the next level and getting your first 10,000 clients, hopefully this 42-page self-assessment would be helpful to you and it could get it for free at DorieClark.com.

Thank you for this time together. Have a great day and thank you again.  

Thank you so much. It’s great to talk with you.

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