Emerge and Evolve

A Series on the Never-Ending Journey of Leadership and Entrepreneurship

Series Background

In 2006, I founded a company called Three Pillar Software, which would eventually become 3Pillar Global. In the 15+ years since, 3Pillar has grown from 6 team members all located in Northern Virginia to more than 2500 employees living in 9 countries.

My leadership abilities have evolved out of necessity as 3Pillar has experienced rapid growth. I’ve gone from writing code 80 hours a week to spending my time focused on building high-performing teams, developing a long-term vision and strategy for the company, and deliberately crafting a culture that respects the dignity and unique talents of all our team members.

I get asked often how I made the leap from writing code to running a business. My answer? I was lucky enough to surround myself with amazing, talented teammates and mentors, and in this series, I talk with just a few of the people who’ve had a major impact on me over the years.

Why We Created Emerge and Evolve: Becoming the Leader You Were Made to Be

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Episode 1: Why Are We Here?

On the first episode of the podcast, I share some background on why we’ve chosen to develop this series and why leadership is such an important topic to me. I believe there is a vast void of principled leaders in the world today, and this void is contributing to many of the fault lines we see in so many areas of the world today. Tune in to this episode to find out more about why I get fired up to talk about leadership and what’s in store for season 1.

Episode 2: Leadership & the Stages of Growth, Part I

For episode 2 of the series, I talk with one of my earliest mentors, Bobby Christian, about the phases of growth that startups go through and how a leader’s focus must evolve as companies pass through each of the phases. Bobby is a serial entrepreneur who was instrumental in 3Pillar’s growth and my own personal development. Tune in to the first installment of a 2-part interview with Bobby to hear timeless leadership advice like, “Nobody can ride 2 horses.”

Episode 3: Leadership & the Stages of Growth, Part II

Bobby Christian joins us for the second half of our discussion on how and why your leadership focus and capabilities must adapt as your company moves through various phases of revenue growth. We learn in this episode that the entrepreneurial journey isn’t always as rosy as it’s portrayed to be. Tune in for some hard-earned wisdom from Bobby and me around the importance of cash flow, how to deal with the challenges of melding cultures after an acquisition, and learning to accept that people leaving your company, while difficult, can also present opportunities for growth.

Ep. 4: Emotional Intelligence & Evolving as a Leader

Jennifer Stanford joins me for Episode 4 to talk about the necessity of leaders developing and honing their own emotional intelligence. We discuss why self-awareness, authenticity and psychological safety, and a willingness to continually work on oneself are key cornerstones of development for anyone in a leadership position. For me, gaining a deeper understanding from Jen of each of the four stages of emotional intelligence was a revelation for preparing myself to lead others.

Ep. 5: Mastering the Fundamentals of Leadership

Alan Stein, Jr. joins me to talk about the importance of mastering the fundamentals of leadership for episode 5 in the series. Without nailing leadership basics like building trust, developing mutual respect, communicating effectively, and being responsive to a fault, any leader will struggle to take his or her leadership game — and the teams they are charged with leading — to the next level. And they certainly won’t be able to stay there.

Ep. 6: Finding Great Mentors & The Importance of Mentorship

Mark Timm joins me to discuss the importance of mentorship in evolving one’s leadership abilities, as well as how to find the right mentors for each season of your life and career. As Mark says during the episode, “The world is divided into halves. The haves have mentors; the have nots don’t.” Watch this episode for more on why mentorship is such an imperative for leaders to continually grow. You’ll hear about the role mentorship has played in both Mark’s growth and mine, and how we were first got to know one another through a mutual mentor, Michael Hyatt.

Ep. 7: Scaling Culture & Developing a Common Ideology

Jamie Whitacre has been an amazing ambassador for 3Pillar’s values since she joined the company more than 12 years ago. For any leader of a growing company, there comes a time when cultivating your culture through osmosis doesn’t cut it. Whether it’s because you’re adding more team members or expanding to new locations, you have to become purposeful and intentional about your culture. Jamie and I discuss our shared path in taking the 3Pillar culture not just beyond our 4 walls, but international.

Ep. 8: Making & Managing Acquisitions

Acquisitions are important, potentially vital tools for growth that leaders must use judiciously. Dan Henderson joins me to discuss making and managing acquisitions on this episode. Dan is now 3Pillar’s Head of Corporate Development and M&A. He and I go back a number of years, as he watched 3Pillar grow from afar for about a decade, often serving as a sounding board for me when he was helping invest in early-stage technology and life sciences companies at CIT GAP Funds.

Ep. 9: Why Diversity Builds Stronger Leaders

I can’t tell you how valuable it is as a leader to surround yourself with people who are different than you are (and who are willing to challenge you). Heather Combs spent 5+ years as my right hand before graduating to become CEO at StraighterLine. 3Pillar experienced more growth as a company with Heather in this role than we did with any of her predecessors. I could feel myself taking similar strides from a leadership perspective. What was the secret? Partly, it was that Heather and I are very different and see the world differently. We have vastly different backgrounds and career experiences, and we often had debates or discussions over whiteboarding sessions while searching for the best outcomes.

Ep. 10: Connecting the Dots + Season 1 Wrap-Up

For the final episode of season 1, we look back at some of the common threads and leadership themes that emerged in conversations with numerous guests over the course of the season. Among those were the importance of people, humility, and being coachable. Effective leaders truly care about investing in and developing the individuals and teams that they lead. The best leaders know that it’s not all about them, and they think and act accordingly. And for leaders to continually evolve, they must also find ways to get feedback and work on their own weaknesses.

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