A successful entrepreneur shares her thoughts on business success and failure.

Posts published in the Ask Erica category:

Ask Erica: “Why Did You Decide to Coach Full-Time?”

In mid-July, I announced my new direction: coaching successful entrepreneurs full-time.

By far, the most popular question I’ve gotten is “Why did you decide to coach full-time?”

The answer, while simple, took me a while to get to. If you’re feeling stuck on your current path, keep reading, as the conclusion I came to (and how I figured it out) may help you, as well!

The Question That Changed Everything

The most motivating factor in my new career path as a CEO coach is contained within my answer to this question: “What’s the most exciting moment you’ve ever had?”

When I opened up and looked back honestly, my most exciting moments were watching people go through breakthroughs, like the story I told about my dinner with Ramit Sethi in my July post. Watching people right in front of me have a powerful emotional transformation–those were the moments I remembered, the moments I lived for as a person.

There were other signs, too. When I first met Jason Seats at Techstars, for instance, I had no intention of going through the Techstars program as a founder (though now I’m very glad I said yes to that and went through the program!) I wanted to be a mentor. I wanted to help other founders.

Then, there was the fact that I just couldn’t seem to stop helping people. Even when I didn’t feel like I had much time, I would always drop what I was doing to help someone out. Especially the rising stars like Ramit–I knew these folks were going places, and it was always so fun to help them get where they were going.

Digging Deep Into Myself

To go from “I like helping people” to coaching full-time, though–that was a transformation! Through the past three months, as I went through the sale of my business, took over a month off, and then spent another 5 weeks in solidarity with the question “What do I really want to do most?”, I dug deep to find out how I really wanted to make an impact on the world.

I’m here to coach because I have been through it all. In the past 13 years, I’ve run several bootstrapped companies and one funded company. In all, I’ve sold three technology companies. I have personally made over $3 million online–all of that being sales from companies I’ve created from nothing.

I’ve hired some of the greatest people I’ve ever had the pleasure of knowing–and hired the worst people I’ve ever dealt with! (All of which I take full responsibility for.) I’ve worked every side of a business from software development/programming to hardware to operations to management to technical support.

Whatever crisis founders of six-figure and seven-figure-a-year businesses are going through–I’ve pretty much been there. I’m not perfect, and as a seasoned entrepreneur, I know you aren’t either. That’s why I became a coach–to help you work through whatever barriers come up as you make the transformation from successful business owner to the huge next level that is waiting for you.

Struggling to Find a Mentor

When I get interviewed by the media, interviewers always love to ask: “Who is your mentor?” I’ve often struggled with that question.

Nearly 10 years ago, I desperately asked on Web Hosting Talk if anyone else knew another woman running a web hosting company that was about to hit 7 figures in annual revenue–and there was silence.

I couldn’t believe I was the only one–but back then there were probably only a handful of female founders of web hosting companies at all, let alone ones making 7 figures a year. I was a pioneer, and for that I was grateful–but it was a searing, raw, emotional experience to feel all alone in that role. I will never forget that experience–calling out, “Where is my mentor?” and hearing only silence.

Today, of course, there are many people who add “Mentor” or “Coach” to their resumes or LinkedIn profiles. But there are scarce few who have actually made millions of dollars online running real businesses–who are now coaching. I know, because I have looked for them! I have begged to be coached by people who are where I want to be, and the answer is often: “No.”

Why Most Successful Entrepreneurs Don’t Coach

Why? Successful entrepreneurs will tell you the answer: There is no leverage in coaching. They don’t have time for it. They are busy running successful companies.

I can tell you, truthfully, that that was the biggest block I had to get over as a coach. I knew that to be a successful coach, I’d have to commit to it full-time. That commitment meant I would not be focused on growing a scalable business (at least for the time being.)

I had a lot of fear around that. Was I basically tying bricks to my feet by creating a business where my income didn’t scale with more products sold?

To really get over the fear, I had to go back to what fulfilled me the most. Did I want to have a little impact on a lot of people (for instance, by writing a book) or did I want to have a huge impact on a few people?

I remembered the feeling I got when I saw people transform and their barriers break down. I decided I wanted more of that–and that was the answer for me. Coach full-time. Make the commitment. Enable the transformations to happen.

Making the commitment was scary for me, but I did it publicly so I couldn’t turn back. And it’s paid off–now, not only do I have amazing paying clients, but I’m excited every day to get up and start working. My coaching calls are transformative for my clients–and they are also transformative for me. In that way, I consider myself deeply blessed.

Who Are Your Customers?

My other huge fear came from the coaching I’ve done in the past. Previously, I’d worked with entrepreneurs who were just getting started, and I hadn’t charged much for coaching. They couldn’t afford it, and I didn’t have the self-confidence at that time to charge more.

Some clients went far. But with others, I’d spend an entire hour 1:1 and we’d never be able to dig deep into their real problems–because we were too busy grappling with “What idea should I work on?” or “How can I get this WordPress theme set up?” It wasn’t fulfilling for me or for my clients!

It was with this concern in mind that I read The Prosperous Coach, a fantastic book written by my friend and successful coach Rich Litvin. In the book, he described clearly the clients he was going after–successful, high-powered women.

While reading his book, I had a complete epiphany. It’s one of those epiphanies that seem so obvious afterward. It went something like, “OH! I can define who I want as a client!”

Becoming a Better Coach by Defining Who I Want as a Customer

I don’t know why that hadn’t occurred to me in the context of coaching before. In the marketing world, defining your customer avatar is an integral part of setting up a marketing plan. But I hadn’t thought to apply that concept here.

I thought deeply about who I’d had the best results with, and a pattern quickly emerged, with Ramit circa 2008 being my defining avatar. Someone whom I know is going to be successful. They’ve already set up a website. They have a product with customers. They’re making well into 6 figures or 7 figures and they’re facing a huge pivot point in their business–do I sell the company? Who do I hire to help me out? How do I raise my next round of capital?

That’s the point at which hiring a coach delivers huge results, and where my expertise becomes most valuable. Selling your company? I’d be happy to help you navigate those tricky waters; I’ve sold three. Raising a round of funding? I’ve seen hundreds of pitch decks, raised $640,000 for my own company, and won a pitch competition. Hiring or firing the right person? We could spend hours on that alone!

Those are the inflection points where having someone to talk to who’s been there are most critical in your business. How much equity do you give your new COO to make sure he or she sticks around but you’re not “giving up the house”? What’s the best process to find a buyer for your company? Which investors should you talk to and how much should you raise (or should you even raise at all)? Or: You’re working 70 hours a week and you feel like you’re drowning, but you don’t know who to hire or where to outsource first. These are all scenarios for which the answer may mean a 7-figure swing in your business either way. And it’s those areas where I deliver the most impact as a coach.

Why Only Four People?

In my July blog post, I mentioned I would be taking 4 clients. Why only 4 clients? (Another popular question!) I always smile when I give the answer: Because, for the first time in my life, I’m undercommitting myself so I can serve those 4 people with my full attention. With only 4 clients, I have time to look over paying clients’ pitch decks, make intros, and help guide them through selling and/or financing companies. I doubt it will surprise you to read: It’s been the best decision I’ve made so far!

I currently have 30 applications in, and I’ve already filled 2 of my 4 available slots with paying clients. I’m continuing to do coaching with applicants over the next few weeks, and I expect the other 2 slots will fill quickly. If you meet the criteria (6-figure or 7-figure business at a pivot point; looking for your next steps) and would like to be considered, please apply here.

Going full-time into coaching was a gutsy move, and an unexpected one. But, in a way I haven’t felt in a long time, it feels right. I got off my coaching call recently with a new client and told my roommate, “I can’t believe I get paid to do this!”

I help create miracles in successful entrepreneurs’ lives, and at this time, there’s nothing I’d rather be doing.

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How To Become A Writer

How To Become A Writer Through a sort of strange coincidence, I found myself reading Tucker Max’s blog today.

If you know who Tucker Max is (and many people do), you may think I was reading his famous “asshole” blog. Interestingly enough, though, Tucker seems to have matured lately, and is now writing a more thoughtful blog on how to become a writer, run a startup, and get published.

He highlights a thought-provoking question on his post “How To: Find A Mentor”:

“‘Why do you want to be a writer?’ 99% of [people who tell me they want to become a writer] have no fucking concept of how to answer that question. They’ve never even asked themselves this most basic and fundamental question. They stutter and stammer and can’t come up with even one concrete reason. [And BTW--there is only ONE correct answer to that question, I will cover that in another thing I'm writing.]“

Interested, I thumbed through the rest of his blog, but I never found where he followed up with the answer. Since I’ve gotten this question too (although it more often comes in the form of “How do I become a blogger?” with me), I figured I’d answer it from my perspective.

I Struggle to Answer the Question

And then…something strange happened. I struggled to answer the question. I had a momentary panic attack: Was I one of those awful 99% of people who “wanted to be a writer” yet “had no fucking concept of how to answer that question”? But no, that didn’t feel quite right. (more…)

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Why Most Internet Marketers Fail

Why most Internet marketers fail.
Richard writes in with a question: “When can a person tell a blog is just about making money with affiliate sales vs. truly helping a person or business? Sometimes they sound really alike.”

This is a great question. Many bloggers–myself included–run promotions for both our own and other products on a regular basis. Some blogs are heavily promotional, with an affiliate link in nearly every post, whereas other bloggers make their money mostly through advertising and only rarely include affiliate links in their posts.

First, let’s look at things from a blogger’s perspective. Then, I’ll give you a few metrics to help you decide which marketers to follow online. (more…)

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oDesk Review: Is Outsourcing Worth the Effort?

oDesk review: Outsourcing.
oDesk review from a real user. Does oDesk work?
I wrote about how to outsource around-the-house tasks earlier, but many of you (including, most recently, Christine) wanted more detail on how to outsource jobs that can be done online.

I’ve definitely had success outsourcing jobs online. In this blog post, I’ll show you which tasks I recommend you outsource, how much you can expect to pay, and where to find good workers. When you’ve read this post, you can immediately take action and start taking some work off your own shoulders. (more…)

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Overwhelmed by "Getting Things Done"? Try This Instead…

overwhelmed by getting things done If you feel like you’re not getting enough done in your business, but complex systems like “Getting Things Done” feel like too much of a production, I completely understand. Here’s my simple to-do system–an alternative to “Getting Things Done”–that I have been using for years. Try it yourself and you just may notice a sea change in your productivity. (more…)

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I'm Erica Douglass.
After selling my online business at age 26 for over $1 million, I created this blog to help you grow your own business quickly.

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