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I Landed 2 Consecutive Companies on the Inc. 500 List–Without Any Funding. Here’s How

The 2018 Inc. 500/5000 list is announced! Here’s a sneak peak into what it takes to scale a company fast enough to make the cut.

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BY Debbie Madden - 28 Aug 2018

I Landed 2 Consecutive Companies on the Inc. 500 List--Without Any Funding. Here's How

PHOTO CREDIT: Getty Images

The 2018 Inc. 500/5000 list of fastest growing private companies in America was recently announced and I'm honored that my company, Stride Consulting, is no. 256 overall, and is the no. 1 fastest growing bootstrapped software company in New York.

In fact, this my second consecutive bootstrapped company on the Inc 500 list. My first Inc 500 company, Cyrus Innovation, landed on the list in 2009, and was then on the Inc 5000 list five years in a row, from 2009 to 2013. In 2014, I sold that business and started Stride Consulting, which has grown 1,917 percent in four years, earning it spot 256 on the 2018 Inc 500. Both companies were self funded and profitable.

Throughout the years, there have been ups and downs. I ignorantly thought that the bigger my companies got, the easier things would become. The opposite is true -- the bigger the companies get, the bigger the risks become. As I look back, there are four things that I can credit for the success of both Inc 500 wins:

1. "I" didn't do anything. "We" did everything.

The minute you think you can do this on your own is the minute you will fail. Companies succeed because they have strong teams, not because they have strong leaders. I, myself, did very little. The most important things I contributed to our success were:

  1. Hire well and then promote and move around people who are strong culture fits and strong team players so that the best teams are constantly formed and strengthened.

  2. Fire individuals who are not a culture fit or who no longer belong on the team.

The team that gets you to $1 million is not the team that will get you to $10 million, and beyond. In four years, we've grown from $0 to $13 million, and we've changed leadership teams three times. Some of the initial team have stayed. The rest of the team has been built up by promoting internal employees and through hiring. Despite the fact that changing a team is extremely costly, it is a key ingredient to scaling. Always aim to have a leadership team today that can get you where you want to be tomorrow.

2. Listen to Lencioni

If you want to scale a team fast enough to land on the Inc 500 list, read The Advantage by Patrick Lencioni. According to Lencioni, team trust and healthy conflict are the foundation of success. In fact, the single biggest competitive advantage you can give yourself is to build a team that trusts each other.

As simple as this sounds, forming trust is actually really hard. And, it doesn't happen organically. It's a mistake to think that just because two people spend their work week together, they will grow to trust each other.

Instead, proactively and explicitly foster trust. I go as far as setting the expectation with each team member that earning the trust of their team members is a requirement for being on the team.

And then, every quarter at our strategy sessions, we rate ourselves on Lencioni's five pillars of a healthy team: Trust, healthy conflict, commitment, accountability, results.

3. Embrace Mixed Emotions Every Single Day

Every single day, I wake up and instantly feel both utter joy and extreme stress, at the same time. This feeling lasts until I go to sleep, every single day.

It's a mistake to ignore these emotions. If you hesitate to make that tough call because your emotions get in the way, you will fail to capitalize on opportunity. In order to grow, you have to take risks. And the bigger you grow, the bigger the risks you have take.

Recognize that taking risks comes hand in hand with a rainbow of emotions. When emotions arise and they confuse you, ask a trusted co-worker or board member for advice. I often say "I need to decide X and I'm feeling Y. Can you help me separate the two?" Being explicit about my emotions in this way has helped me make better decision quicker, and that's been a key ingredient in our success.

4. Run into change

When you are scaling, you are going to face change -- lots of change. Everything is going to break multiple times: the people, the systems, the processes. Run into change by embracing it and bubbling issues to the surface.

At our quarterly strategy sessions, the most useful question my leadership team asks is "Which processes are least effective and why?" Notice that we don't ask "Which processes are broken?" If we ask the second version, we run the risk of answering "None" and pat ourselves on the back. If we ask the question the first way, we force ourselves to identify our lowest performing processes.

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