I often get asked what you might think is a simple question: “What kind of business should I start?”

For the first time in many years, I find myself in the same boat as the folks who ask me that question. I (surprisingly) don’t have a concrete answer to this question for myself right now–but, as I’ll show you in this post, I have a way to figure it out. (more…)

When I decided to become a coach in July, I sought out several experienced coaches for advice. After all, if I was going to make this my new business, I wanted to know what to do–and what not to do–to make my business successful!

One coach I spoke to advised me, “Charge less so you can build up a client base.” At the time, I had an almost visceral reaction to it. I replied, “No, I’m going to charge more.” She looked at me with surprise. (more…)

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.

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…)

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…)