This month, August 2018, is the 5th anniversary of Trajectify. Words cannot express how grateful and lucky I am to have been able to build this business and accomplish all that we have. But I’m full of words, as many of you know, so how can I not share the stories and lessons learned :-)

How a Business is Born

I decided to leave startup #7, Real Food Works, in April 2013. I had turned 50 a few months earlier and found myself wondering, “what do I want to be when I grow up.” I told myself no more startups. So I embarked on what turned out to be a three month discovery mission that led me to create Trajectify in August 2013.

A week in August 2013, just before Trajectify was born, at the end of the 70+ networking meetings as part of the coaching product-market discovery.

Over the course of the three months, in addition to attending dozens of networking events, I had meetings with about 70 people who helped me shape what came next. In the first month of conversations, I explored what problems there were to be solved. I discovered a pattern in lack of quality mentorship. I love to mentor though it's not a business. It got me thinking about coaching. In 2011 when I had started and built Novotorium, a business incubator, I attended a coaching training program. I knew that could be a business. In the second month of meetings, I explored the opportunity to coach, to determine where coaching might be needed, and how a product-market fit might look. That led me to develop a model. The third month of meetings I tested and refined that model. I launched Trajectify in late Aug 2013 and within five weeks had my first five clients.

This process might be the definition of looking before leaping. It worked. By being patient, consultative and thoughtful — looking at things from the outside-in — I was led to a model that allowed me to hit the ground running. The early successes of having landed clients so quickly helped build my confidence, which I needed given that I had never been part of building a service business.

And So Begins the Learning and Accomplishments

Of those first five clients, we still work with two of them - one continuously (who has grown from $250K to $10M), and one periodically (who exited last year for 5x revenue without outside capital, and we continue to support post-acquisition).

The challenge with achieving traction quickly is that I focused on operations more than sales and marketing. It’s not a terrible problem to have, but it brings in short term revenue and only serves to create a “job” for oneself. Without a repeatable customer acquisition model, you haven’t built a business. It took me a while to get the website up, to consider ways to market and sell, to develop a plan for growth.

Knowing I was going to get stuck, I got myself a coach — because it works and everyone should have a coach. The good thing about being an entrepreneur building a coaching business having a coach who coaches entrepreneurs is that you not only get a coach, but also a role model. Follow that logic? Ivy Slater not only coached me, but I was able to model some of what I did based on how I observed her build her own business.

I added five additional coaching clients in 2014 and realized I was nearing capacity. How do you scale a service business? You either hire service providers and build teams to deliver, or you come up with services that have more leverage. Not ready to hire, I decided to start a peer coaching program as a way to serve more clients with less time. Called Trajectify Acceleration Groups, I recruited 8 business leaders to work together once a month for a half day. It was a lower cost option for them and opened Trajectify to new markets. It was more scalable, coaching 8 companies in four hours. In our first year together, 6 of those 8 companies (75%) doubled revenues. It was working.

Later that year, one of my clients found their way to an exit after six months of our working together. They sold for 25x revenue (and were bootstrapped). I was able to coach them through the transaction. The realization that what I do helps change lives is something that had great impact on me.

In 2014, the Philadelphia Business Journal named me a “Most Admired CEO” of the year, which being in business for one year and having no employees was quite an accomplishment!

Never Say Never

In 2015, the unthinkable happened. Through a serendipitous series of connections, I met a visionary and investor who ultimately became my cofounder for startup #8, IntroNet. This was an opportunity that I didn’t want to let pass, though not an easy decision given Trajectify was going well and I had already sworn off doing another startup. Never say never.

Rather than put Trajectify on the shelf or back burner, I decided to bring in a couple of colleagues to take over the clients. Chuck Hall and Joe Spinelli joined me, we coached together for a few months until I transitioned over most of the clients to them so that I could focus on IntroNet. It was quite seamless, there was little loss in the process. For the next 18 months, Chuck and Joe maintained Trajectify. While they didn’t focus on growth, we continued to deliver incredible services to our clients.

By the end of 2016, it was clear that IntroNet wasn’t going to make it. I wrote about some of the lessons learned. No matter how many times you do it, there are always new things to learn and new mistakes to make.

In early 2017, I stepped back into Trajectify. I decided it wouldn’t be right to take clients back from Chuck and Joe, who had become their trusted advisors. Rather, I’d rebuild a pipeline and new clients for myself in Trajectify, like when I first started the business, but this time at least with some experience and a website.

Discovering Version 2.0 of the Business

As I said, I’m an operator. The challenge for me starting from scratch is that all of your time is spent doing sales and marketing (or at least should be). That didn't make me happy and as a business owner, our happiness should be our top priority. So while I was rebuilding, I reached out to past and current clients to see if they needed any assistance with something that had them stuck. They already had coaches, but I could step into the trenches with them and work side-by-side overcoming a challenge together. Within a few months, I had a few of those engagements. We were helping with organizational development and staffing, process optimization, strategy development, and customer development.

In addition to this new “management consulting” practice that began to develop, the coaching pipeline grew and we began to add new clients. I started another peer coaching program. And we were also doing career coaching for exited entrepreneurs and executives in transition — for people like ourselves who had to figure out what they wanted to be when we grew up. And we held our first Trajectify Leadership Retreat. And we helped another client find their way to an exit (the bootstrapped one at 5x revenue), creating more millionaires.

Later that year I had heard that a Product leader who I admired was leaving his job, Joe Cotellese. Introducing top people at my clients is one of the greatest value-adds we can provide. I could quickly get Joe hired by at least two of our clients, so I reached out to Joe and offered to make the introductions for him. It turns out that Joe isn't looking for another job, he wanted to consult. That led to a discussion that brought Joe on as Trajectify’s fourth coach. Now a total of 110 years of experience combined.

In 2017, we quadrupled revenues and doubled profits. The growth was organic, meaning mostly without goals or a plan. I had to re-ask myself the question (with guidance from all our coaches) — was I building a job for myself (lifestyle) or building a business?

Now We’re Really Building a Business

I decided that I was building a business. We are a coaching business. The management consulting follows the coaching. I had a strategy, set some goals, and started a plan.

I would be making investments into the business to make it happen. I invested in training and studied other coaching practices. We decided to hire a content marketer and Jamie Walsh joined us this Summer. We wanted a more strategic presence in NYC and started to host events there and align ourselves with local partners. Through one of those partners I met Lauren Kaplan, who, like Joe, was leaving a job and wanted to start a consulting practice. She became our fifth coach, further establishing Trajectify in NYC and giving us deeper perspectives to a new generation of leaders as well as the differences in the challenges and issues that women leaders and entrepreneurs might face.

We’re now working on building a repeatable model for customer acquisition. Content is king. (You’re reading this, right? Email. Blog.) You’ve seen some of my videos? (They are more effective than any other content we’ve produced.) And we’re doing our first BIG event, the Trajectify Live Business Growth Conference, bringing together Trajectify coaches with sales and marketing experts to help grow 100 professionals meet bigger and bolder goals. We’ll schedule a Leadership Retreat for later this year (the one we did in 2017 not only helped leaders prepare for 2018, but also helped Trajectify land two new clients). Is it working? We got more prospects in the last three months than I did in all of 2017. I’m now learning more about the other end of the sales funnel. While I may be a keynote speaker at the Trajectify Live conference, I am going to learn a lot there, too. (And like this article, there will be no secrets at the conference. If you want to learn with us, register to be there September 13th in Philadelphia!)

We also wanted to make our peer groups more scalable, so you’ve likely seen that I got certified by The Alternative Board. We’re now building peer advisory groups as part of their system (The Business Builders Blueprint) and community (of over 3000 business owners). Our first group launches next month.

Five Years, But We’ve Only Just Begun

We have a Trajectify Highlights page on our website. These kind of accomplishments motivate me to keep working on Trajectify, investing in and building it. Even if this is as good as I could do, and have only created a job for myself, it’s still the best job that I’ve ever had. I have bigger goals to accomplish for Trajectify, so in some sense, I’m still at the beginning.

In 2014, 75% of our clients more than doubled their revenues for the calendar year. Mike was named A Most Admired CEO for his work at Trajectify by the Philadelphia Business Journal.

In 2015, two clients received offers acquisition offers. One sold for 25x revenue, too rich to turn down. The other had so much confidence, that they didn't accept the offer and have continued to double revenues each year.

In 2016, 5 of the top 25 companies ranked in the Philadelphia 100 worked with Trajectify. Presented by the Wharton SBDC and The Entrepreneurs' Forum of Greater Philadelphia, the program identifies and honors the 100 fastest growing, privately held entrepreneurial companies in the Greater Philadelphia Region.

In 2017, 5 Trajectify clients were on the Inc. 5000 list of fastest-growing private companies in America. One of our clients exits for 5x revenue. Joe Cotellese joined us as Product Management coach.

In 2018, Trajectify client My Independence at Home was named SBA Minority-owned business of the year. We increased programming in NYC, including Bootstrappers Breakfasts. We launched The Alternative Board (TAB) peer advisory boards. Lauren Kaplan joined us as Operations coach. Jamie Walsh joined us as Content Marketer. The Trajectify Live Business Growth Conference is in September.

Somewhat Embarrassing Fun Facts

Even after five years, I still keep our books (financials) in a Google Sheet, against every recommendation I’ve made for others to not do.
I’m willing to delegate a lot, but happen to be a control freak about our website, which I foolishly built and maintain myself.
I still use the logo we got from 99designs for $300. Startup blood runs deep.
We’ve worked out of nearly every coworking space in the Northeast and Mid-Atlantic. I still carry my office around in a very heavy backpack.
I have 4 t-shirts (XL) left over from the 2017 Trajectify CEO Leadership Retreat which I will give to the first four people who comment on this article sharing how wonderful it is.

I’ll keep adding to this list as people remind me about them…