From $100,000 in Debt to Huge Money: An Interview with Carrie Wilkerson

Carrie Wilkerson, Entrepreneur, Writer, Coach and Mentor

Carrie Wilkerson, Entrepreneur, Writer, Coach and Mentor

Carrie Wilkerson’s initial goal was not to get rich. It was to find a way to get a paycheck so she could stay at home with her two recently adopted children. The beginnings of entrepreneurship were not easy for Carrie. At one point she found herself in a little over $100,000 dollars in debt and over 100 pound overweight. Then one morning she woke up and said, ‘Enough is enough.’ Since then Carrie has lost 110 pounds, sold a business that produced over 5 million dollars and continues to grow and build new businesses today.



Here is a bit of her story.

One of the things I thought was very interesting about your story is when you began this journey you were 110 pounds heavier than you are today and 100s of 1000s of dollars in debt. I am wondering what your thoughts are on how you got to that place?

I think it is the same way we get to any place we are in life when we are not paying extreme attention. I think it is a lack of making smart choices. It is not even like living in reckless abandon. It is not like you are bingeing every day. It is not like you are wearing designer clothes. Some people are, but we weren’t. We were coasting. We were making unintentional choices. I think the change comes when you start living intentionally. When you start thinking about everything that you put in your mouth, about every way you move your body and how you make your financial and spending choices.

How did the transition happen?

I think sometimes it is the frog in the pot where the temperature slowly starts to go up until it is boiling. Sometimes it is eating out one or two times too many. It was a matter of choice. I had two little kids. I was eating what they were eating and doing what they were doing, but it comes to the point where you realize you can take your life back. You can reset it, you can be a victim and be a martyr about it or you can wake up one day and say enough is enough.
At what point did you realize you could go from 100s of 1000s of dollars in debt to mega business owner?
Initially the immediate goal was to meet all of my minimum payments. When I started working at

home my first business was what put me into some of that debt. I started working from home 14 years ago, but it was 10 years ago that we started getting ridiculously profitable. In the beginning it was just a matter of making the minimum payments so I could buy myself some time and get my legs under me.

Within six months I could really see that we were making a big difference in our financial statement. I could really see as a business owner I could work more and make more or I could spend less and make even more which made an even bigger difference or I could have more clients and subcontract to other people and make even more of a cushion to get of debt. It was about four to six months before I really saw the light at the end of the tunnel and saw the power was back in my hands.

What were the different business ideas you tried along the way?

I started out in direct sales, a party plan company. It was 14 years ago and there were not a lot of options to work from home. I needed a turnkey system with low start up costs. I did not have any business knowledge whatsoever. The next business I combined my communication and my publishing skills to start a newsletter business. We had a virtual business before virtual was even cool. We were on dial up Internet. Back then we were kind of pioneers in that. We were paving new ground. Then I evolved into training and online marketing, coaching and mentoring.

One of the other things I thought was really interesting about one of your blog posts is how you talked people who chase more than one rabbit as a metaphor for how people if they want to succeed need to focus on one thing at a time. What are your recommendations for someone who has a lot of business ideas but does not know which one to pick? How do they pick which to do first?

Even as a teenager I always dated more than one boy because I did not want to choose just one until I was sure and I think a lot of people work the same way. I liken people who are chasing so many things to being hesitant to commit to one area. They do not want to pick one thing because they are hesitant to commit. They are afraid it is not going to work or they have been told their whole life not to put all of their eggs in one basket, but as I talk about in my book it is not just about focusing on one business idea it is about focusing on one business model until you start making that profitable and then you can replicate that. For example with my newsletter business I had tons of people saying, ‘Would you also do websites? Would you do your newsletter with our business?’ We worked with one direct sales company only. We did not duplicate it for any other market. We just stuck with that one market. We were a one trick pony in that market. We did 5 million dollars just in that business for focusing. We could have focused on other things, but what happens is it fragments your attention and your resources and then your customers get confused. It is just not a good idea. I have multiple businesses now. But it is because I will get one going and then start another or I will get one stream of income going and then get another stream of income started.

It is better to focus on one path. If you are going to focus on throwing five things against the wall and see which one sticks the fact of the matter is your eyes are darting back and forth between these five things. I was talking to an energy guy the other day. He told me, ‘You have to choose between whether you are going to be a disco ball or a laser beam.’ Both use the exact same amount of electricity, but their results are very different. One can cut through steel and the other is just pretty to look at and I thought, ‘Wow that kind of sums up the whole concept behind what is wrong with having a scattered focus.’

If people had 10 business ideas, do you have any recommendations on how they say, ‘Option A is better for me to start with than Option B.’

I teach this a lot with my personal coaching clients. I can’t go into all of it. What I tell them is to honor every idea. I have an idea book and I write down every idea I have. Sometimes the idea does not fit into my model or what I am doing at all. What I will do is email a friend or post it on Facebook or Twitter, so I will find a way to honor that idea and then I will cross it off in my book. I actually give myself permission not to be responsible for that idea anymore. It may sounds silly, but we feel so responsible for our creativity it is actually nice to give it away.

I also go through what I consider the motive matrix and I look at it and think, ‘What is my primary goal for my business right now?’ Your motives fall into a couple of different areas: profit, leads, products, platform, or infrastructure. You need to know for this month or for this quarter what is my priority? Am I building up cash? Am I building up infrastructure? What is it? If those ideas don’t directly benefit that goal right now then they focusing on them will take you away from your ultimate goal or just leave you stagnant. Therefore you cannot use that idea right now. Give yourself permission to look at it next quarter.

You have written about ‘knowing your value’. I see a lot of new businesses starting out that are charging a lot less than what their competitors are to get clients and grow momentum. Do you at all support having lower rates in the beginning as a means to get clients in the door?

With my newsletter publishing business I took on one client pro bono and I told her that I would like her to be a guinea pig, a beta tester if you will, for two months. I told her I wanted to do it as a testimonial and to use her newsletter as a sample when I got ready to go live. I put a timeframe on it. We had a written agreement. I let her know there would be flaws and it would not be perfect. I also let her know that if after two months if she wanted to continue working with me what my fees would be. After 10 years she is still my client. When I was ready to go live I was able to use her newsletter and her testimonial as a reference. I do not think it is a bad thing to do, but you have to put very clear boundaries on it and the expectations you have of them. For example, you have to tell them that this is in beta and I am going to screw up a few times and this is why I am giving you my lower rate. Then after such and such date my rates are going to be a full market rate. In exchange for the low rate I would like your testimony and to use you as a sample client. I think that is where we get in trouble. We give low rates to get new clients, but there is no expectation that the rates are going to go up. There has to be clear boundaries and clear expectations. If you said on August 1st your rates are going up. You need to enforce that. If the client goes away then they are a price tag shopper and you didn’t want them anyway.

I think one of the things small businesses get confused by is which marketing channel to select. These days the marketing channels are seemingly growing exponentially. Do you have any recommendations on how people should choose the marketing channel that is best for them?

I learned this answer from a friend of mine that teaches video classes. People ask him all the time, ‘What is the best camera?’ His response is, ‘The one you want to use.’ I feel the same about marketing channels. I know people who love Pinterest and love direct mail. Those are not my favorites. But they are faithful to them that is what they use and they are successful using them. I like email marketing and Twitter. Do I have the best response from Twitter? Do I convert to a lot of immediate sales? Sometimes. But the best thing about Twitter is credibility, top of mind awareness and connectivity with my audience. For me email marketing and Twitter are key. The other thing I love is video although I don’t know if you can call that a channel.  I do love having a video presence. I would never give up my email auto responder. I can do newsletters on video and then direct them through PayPal and boom you have all the business architecture you need. You don’t have to over complicate it.

Do you have any best practices for using Facebook and Twitter?

Just because somebody agrees to be on your Facebook or Twitter list does not mean that they agree to be on your email list. Don’t do it. It is spammy. It is gross and people don’t like it. As far as best practice, treat it like a party. Don’t stand on the table and shout at people and promote yourself. Walk around. Work the room. Connect with people. Care about people. Ask how their families are and then when they ask what you do or when there is a conversation that comes up where you can be a valuable resource then you can chime in on it. Don’t go in there looking at it as a captive audience that you can promote, promote, promote to. Don’t scrape information and don’t overly promote. I like to say a 15% promotional rate to an 85% conversational, resource and informational rate.

Can you talk about some of the mistakes you have made and the lessons you have learned along the way?

I have made a ton. I always tell people the secret to my success is that I am not afraid to try. I am not afraid to mess up. You have to get to the point where you are more afraid of not trying than you are to try and fail. Sometimes I have already tried two or three different things before the indecisive people have made a move.

The other mistake I made was waiting for so long to hire a coach. Hire somebody that has been there before you. Learn from somebody who is where you want to be. Learn from somebody who has made mistakes. There is no reason why you need those scars that they already have.

Another mistake is hiring somebody too quickly. Hiring someone is a decision that takes a little more time. You need to hire slowly and fire quickly and too often we hire quickly and fire slowly. I also have over invested in short cuts or systems which I thought would be great which I did not have a great ROI on.

People also make the mistake in trying to handle their own books and their own finances. I don’t even care if you are not making a lot of money. Get somebody in your in family who is amazing with money to do your books. Somebody you need to be accountable to. Not someone who will let you embezzle from yourself. Someone who will not let you have an overinflated idea of what you are making and an underinflated idea of what you are spending. Somebody who will be brutally honest with you about the books.

Do you see differences between those who succeed and those that fail in starting their own business?

Yes, one of the things is they don’t focus on one area. That is a huge, huge thing when people won’t focus in one place. They are jumping all over the place. It is a sure path to failure. People think being your own boss is all about working when you want to and not working when you don’t want to. The fact is working for yourself is harder than working for anybody else. You don’t have anybody telling you when you have to show up and what you have to do and in what order. People have to discipline themselves. I have a flexible schedule, but I do put the time in. Somebody told me, ‘When I started using the hours that nobody else wanted that is when I started making progress.’ It is not sexy. It is not fun necessarily, but the results are amazing when you can really strap yourself into a schedule. Not being disciplined is a huge failure factor. I think trying to blame other people or other systems or other things when you lack of results is really because of your lack of discipline and your lack of effort. People who are excuse oriented need to work for somebody else. They need to not start their own business. It is not going to work for them.

You recommend people stick with the skills that they have to start a business. I know a lot of people who have been doing the same thing for 10 or 15 years and have developed a strong skill set in one area but no longer like it. They want to do something different. Do you have any advice for them on how to find a different path?

I always recommend people stick with their initial skills to start and this is for profitability. This is to encourage your skills, get

your legs and get your confidence good and steady. And then when you are at a good level of profitability then I recommend they take a course on the side that lets them pursue their passion. For example, I had a degree in Journalism. I had experience with direct sales. I did not love that work, but I was good at it. I had experience with it, but I did not love it. I did not love it to the tune of 5 million dollars and then we sold the company. It served a purpose for me. It paid off all my debt. It allowed my husband to leave corporate America. It allowed me to give birth to two more kids. It allowed me to provide a lot of opportunity for my kids. It funded my foray into online marketing and into this new amazing space. Writing the book came to me because I was able to put my time in with what I was skilled at. What I recommend to people is do not throw the baby out with the bath water. Even if you hate it right now don’t worry about whether you loving what you are doing right now look at what why you love doing it and then look for ways you can transition out of it.

Make sure you have a transition plan. Maybe you only have hobby time to work on the new interest and new passion but you can use the other skill to fund you so you do not have the pressure or the desperation of the dollar sing in your eyes. It is a hard thing to make a business work when you are working at it from the perspective of desperation. That is why I recommend people stick with that instead of saying, ‘I am going to do something totally different, so I am going to real estate school and I am going to start from scratch again.’ That is good, but let’s make sure we have a profit margin behind it first.
Learn more about Carrie Wilkerson, The Barefoot Executive, on her website:


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