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

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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My Experience at YC Hacks (Y Combinator’s First Hackathon)


YC Hacks I wasn’t quite sure what to expect. At 33 years old, I knew I’d probably be older than the vast majority of the 400+ people attending Y Combinator’s first YC Hacks hackathon. But other than that, I didn’t have many expectations.

YC Hacks was my first real hackathon. Many years ago, I went to the first SuperHappyDevHouse (and then 19 out of the first 20 of them), but I never had built and launched a web app in a weekend. Even though I’ve held down full-time jobs as a developer, I still have trouble telling people “I’m a developer.” I’m not a whiz-kid 19-year-old who grew up programming games in his bedroom, nor do I have a Computer Science degree from a prestigious university (I’m a dropout.) I program because that’s how I get to see my ideas come to life–and because it’s fun and addictive for me. And that’s why I signed up for YC Hacks.

With my startup having been acquired a few months ago, YC Hacks seemed like the perfect opportunity to meet new people and get exposed to the latest Silicon Valley trends.

Team? Team? Will You Join My Team?

My first exposure to the other attendees came through the YC Hacks Facebook group, where people seemed to be in desperate need of other people for their teams. At this point, I wasn’t even sure what I wanted to build, and despite a torrent of private messages and emails from people asking me to be on their team, I didn’t commit to anything prior to the hackathon.

“Are you a designer or a developer?” was a popular refrain on the Facebook group, as well as “What’s your stack?” My response was basically along the lines of “I build shit that makes money” and “Whatever works to get the job done, but probably Javascript.” (Ironically, I would end up building a product at YC Hacks that doesn’t have a monetization strategy. More on that in a bit.) (more…)

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How I Helped Ramit Sethi Break Through Barriers and Earn Millions of Dollars


This post could potentially help you create the next huge online business. I’ll get into that more below, but first, since you’ve been asking, here’s what happened in the aftermath of my last blog post!

It’s been 2 1/2 months since I shared the story of my startup failing here on my blog. And I’m happy to announce I can now share the epilogue to that story: After I wrote the post, Whoosh Traffic was acquired by another local Austin company, OwnLocal. (more…)

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Dear Investors, My Company Failed and We Lost All Your Money. Here’s What Happened.


Something wasn’t right, and I couldn’t put my finger on exactly what it was. On the surface, it seemed like I had the best life. A popular blog with millions of readers. The perfect relationship with Brian, the most adoring fiance in the universe. A great set of supportive friends and a nice social standing in Austin, TX. And, last but not least, an awesome company, making marketing software, with a great team, that was making money and (finally!) shipping products.

Yet something lurked just beneath the surface. It would come out at awkward times, like 3AM, when I would wake up and feel an edge, a discomfort. Something felt broken. But when I looked at my life, I couldn’t spot it. What was going on?

Then, one day, a few weeks ago, an event happened (I’ll save the details of that for some other time.) Suddenly a torrent of emotions poured in. I was overwhelmed. I stayed home from work one day–my best friend Erica sent me some poetry, and I just cried. I wept. It felt like my soul was pouring out of me, one tear at a time.

I reeled from the onslaught of emotions for days, and soon thereafter, I broke off my relationship with Brian. Whatever wasn’t right in my life wasn’t easy to find. It went deep into myself.

Brian was shocked, and as well he should be. I loved Brian. I still love him. But something wasn’t there. It wasn’t right. It was why we weren’t getting married. He was the perfect guy on the surface, but for some reason he wasn’t perfect for me.

I Had to Leave…

That was Friday, April 25. Saturday morning, I woke up and bought a plane ticket to Boulder, CO for six days. It was there that I would kill my company. But at that point, I didn’t know that. All I knew was that I had to leave. I had to get away. Something was so profoundly broken in my life–something I knew I couldn’t see without the perspective that leaving my home in Austin, TX would show me.

Sunday morning, April 27, I arrived in Boulder. I felt a strange sense of unity, peace, and relief. All of the noise in my brain was quiet for the first time in years. I had told Brian this trip was to create my preferences, to help me understand what I wanted in this life. But it was also to fix the pain and the brokenness that I could no longer ignore.

Today is my fourth day in Boulder, and I have not stopped crying. Yesterday, our largest customer, representing 22% of our revenue for Whoosh Traffic, cancelled. Because of their cancellation, we could no longer make payroll next week.

I pinged my friend Andy on Facebook, and I did something that until now has been incredibly difficult for me: I asked for help.

“What Do You Really Want?”

Andy asked me, “What do you really want?” I felt strongly this was the crux of the question that had led me to Boulder, that had led me to drop everything in search of myself. At first, I didn’t know how to answer. But he helped me work through it.

After my conversation with Andy, I got on our company chat room and told Paul (our CTO) and Amanda (my assistant) that there was no more money left, and that we wouldn’t be able to make payroll. I thought they’d be upset, but they were stoic.

Isn’t it interesting how when things are broken in your life, people sense it somehow? I believe that’s why we haven’t raised investment capital in the past 7 months since we got out of Techstars. I knew, somehow, deep inside, that so many things were broken in my life, and that that extended into our business. So how could I ask investors to sink more money in? It would be disingenuous. I couldn’t do it.

The truth was, I didn’t really want to build a huge SEO software company. We knew that coming into Techstars. My cofounder and I split during Techstars, and I decided I really wanted to build a marketing automation platform. That platform would become MarketVibe.

But something still wasn’t right. If MarketVibe was what I really wanted to do, why wasn’t I launching it on my blog? Why wasn’t I doing whatever it took to get paying customers and make it successful?

The Brokenness…

The brokenness pervaded my dreams, leaving me exhausted when I woke up in the morning. I developed a sugar addiction and a video game addiction. I gained so much weight that many of my clothes stopped fitting. It’s hard to explain the contrast between the abject depression that ate at me in the middle of the night when I was alone and vulnerable, and the “everything is OK” smile I’d put on as my “public face.” It was why I stopped blogging.

Today I write this, still in Boulder, still reeling emotionally from the large volume of changes in my life in the past week. I write this humbly, with a complete lack of ego. My business failed and it took my savings, and $640,000 of investor capital on top of that, with it. I let my blog income sources dry up while I focused on the business, and now I must figure out what’s next, from an awkward place I haven’t been in in many years: no money, no salary, and some credit card debt on top of that.

Sometimes you have to rip everything apart to find the core of yourself, the beauty inside you. And this is where I am today.

For so many years, I was the rock, the glue that held my friends together. I was the one who was always there, always ready to listen and give a hug. I was the nice one, the one who rarely judged, who smiled and wished everyone well.

When I tore my life apart, I found an inner core of myself–a twin core of vulnerability and strength, the masculine and the feminine, sitting together peacefully inside myself for the first time. My business failed, but I am not a failure. That’s the key difference that going into myself enabled me to acknowledge on a deep and personal level.

Am I Upset?

Am I upset that I lost my investors’ money? Only in the sense that many of our investors were my friends and I didn’t want to disappoint them. But the me coming out from this hurricane of chaos is a much stronger me, able to acknowledge the mistakes I’ve made, able to open up and be emotionally raw with my friends and my team–qualities that every great leader must possess.

This is what puts one on the path to success–true, authentic success with deep happiness and fulfillment. From where I stand today, I can see why so many leaders are unhappy. They are afraid to be themselves. They are afraid to be vulnerable, to let down their guard, to take the help that their friends and family offer. This is what breaks relationships, both personal and professional.

And now I can share with you what shifts for me this week: I know that this is what I have to offer the world. The twin cores of vulnerability and strength, standing together. As more women enter our workforce, and we as female leaders struggle to find our voices and our innate leadership qualities, we must not forget that the feminine side of ourselves is not a weakness. It is, in fact, our greatest strength as the leaders of this world. We are vulnerable, and we are beautiful, and that’s not just okay–it’s needed in our society.

And as it broke down with me, so it will with others, as we learn how as a society to be authentic, to be raw, to be emotional, to cry it out and hug our friends and tell them we love them. To deal with the pain as it comes instead of bottling it up, taking anti-depressants, and committing suicide (in the worst of cases.) To love without fearing the loss.

The people who embrace that vulnerable core of themselves are our true next generation of leaders, and today I get to stand up and say: That’s me. That’s not just who I want to be–it’s who I am now. I had to break my entire world to find it in myself, but now I stand before you, humbled, having failed in a way but having found something even better from that breakdown.

The world is quiet. The noise in my head is gone. For the first time in many years, I am at peace.

So What Comes Next?

There are a few things that are clear:

I want to keep our team together. Paul, Amanda, and I work together well. So we may form a new company, or rearrange the current one. I think I may do some consulting for a month or two, recovering my finances and helping other authentic leaders of larger companies find their voices and build better teams. (Email me at erica at erica dot biz if you’re interested in talking about this further–it won’t be cheap, but it will be worth it for you.)

And I would like to do MarketVibe, but I think it is time to explore some funding options that buy us some time, instead of feeling rushed to half-ass a product out to market. I no longer sense the perfectionism inside me that was causing us to not launch a product–but I do feel a need to give our product the time and attention it deserves to get the user experience to a state similar to the beauty I see inherent in this world.

Some of our current investors may come along for the ride. Some won’t, and that’s okay. As a person, I am worlds apart from the one who raised money back in 2012. I was not confident in myself back then. I had a gritty edge. I was scared.

Today I’m embracing myself as a leader not just in business, but in our world. I am “in flow” and I know the right people will show up to help me along and support my journey. It is time to show the world that the feminine and the masculine can work together; that neither is inferior, that both are needed. It is time to embrace my own vulnerability and lead by example.

And it’s time to redesign my blog. (Forthcoming!)

if this post compels you to reach out, by all means, do so. (Email, Facebook, Twitter) And if it’s not your cup of tea, feel free to unsubscribe. I am no longer concerned. This is who I am. This is why I’m here. And I’m excited to have you along on this journey with me, through my blog and social media, if you’d like to be a part. (Subscribe to my email list and/or follow me on Facebook.)

Thanks for reading. I’m sorry I lost your money.

With love,
Erica
#500strong #techstars and now… #failed. :)

Update (May 6): We were able to make payroll. My next blog post will have more details.

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My Personal Transformation: 6 Life Lessons From 6 Years of Blogging


6 Life Lessons I launched erica.biz on December 4, 2007. This week, I’m celebrating 6 years of blogging here. Wow!

It’s been just over 6 years since I sold my last company, as well, and I’m amazed at how much I’ve grown. This week, I figured I’d do something special, and share some of the deep, heartfelt lessons I’ve learned in the past 6 years. Some of these were tough for me to grok. All of them have changed me as a person. This may be a tough read for some of you…but I hope these lessons will have as much of an impact on your life as they did mine!
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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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