David DeWolf

Humble Confidence

In July of 2006, David DeWolf’s need to be part of a high-performing team, to work in a positive corporate culture, and to practice integrity in business led him to strike out on his own as an independent consultant. While he had no idea what the future held, his most recent employer had been acquired, destroying the gratifying and productive atmosphere he had once enjoyed.  “The culture immediately went downhill,” he reflects.  “The investors forgot what had lent the company so much value in the first place, and they let it disintegrate.”

It wasn’t the first time David had witnessed such a transformation, but he knew he wanted it to be the last.  “I decided that, the next time around, I wanted to be in control of the company’s destiny,” he affirms.  With that, he set about incorporating himself and searching for consultancies in the software community, never imagining the success he would find.  “I had no vision of hiring employees.  I didn’t think I was going to do anything but go find great teams and work with great people,” he says.

Six years later, David’s independent consultancy has blossomed into 3Pillar Global, a $25 million dollar, multinational company with 600 employees and offices on four continents.

While this measure of growth is certainly impressive, it’s hardly surprising after taking into account David’s emphasis on innovation, collaborative thinking, and adaptation.  In fact, his decision to become independent was motivated by a desire to seek out the best and brightest to build with.  “It was all about how you write software,” he explains.  “You can write a certain amount of creative, innovative software on your own, but true innovation is the intersection of technology and business, and it comes from a collaborative effort.  Like everyone, I have both strengths and weaknesses.  Success is not about being bull-headed and stubborn and valuing your own ideas above everyone else’s.  It’s about confidence, yes, but equally about humility—about knowing when to listen and when to change.  I call this ‘humble confidence’.”

In other words, success is about trusting one’s self and others, and about changing course when opportunity arises, and the growth of 3Pillar is a perfect example.  As David launched his independent career, he was pleasantly surprised at the ease with which he found his first job—an opportunity he attributes to both his past work in the software community, and his speaking engagements at conferences, where he shared his expertise on agile software development, methodology, process, and how to build collaborative teams.  He quickly signed a 6-month contract with his first client and settled in, thinking he would field more offers as the 6 months came to a close.

As it happened, however, the offers continued to roll in.  David, already busy and happy to pass the work on to other qualified engineers, began making referrals, thanking the clients for their interest and sending them on, until he received an unexpected reaction.  “One day, one of the clients came back to me and said, ‘We’d love to use Joe, what do you want for him?’  I said, ‘I don’t want anything, I was just making an introduction!’  But they said, ‘No, we’d like you to be involved, and leverage your relationship to get him onboard.’  So I subcontracted out, and that was my first opportunity to grow beyond myself.”  Over the next 6 months, he continued to sign small subcontracts, and after 8 months, David hired his first employee.

A few months after that, another major shift occurred—the shift that would get the ball rolling on 3Pillar.  David’s original client began struggling with the team they had outsourced development to, and, following a disastrous audit of practices there, they asked for his help and advice.  He saw his window of opportunity and took it.  “I asked them to give me a shot,” he remembers.  “There were two all-stars on the team working overseas.  I wanted to bring them over to the US and try to build a team that would knock it out of the park for them.”

The client did, in fact, take a bet on David.  He immediately hired five employees, bringing the employee count from three to eight overnight.  With that team in place, they got the product to market and turned things around.

From there, 3Pillar continued along the same vein, identifying opportunities to clean up failed projects and take over from outsourced work.  After 6 months or so, however, David stepped back and reflected on the direction of the business. “There’s something wrong with betting your success on everybody else failing,” he affirms.  “We couldn’t just continue to clean up after everybody else.  I decided at that point in time that I was going to figure out how to do 3Pillar better.”

David didn’t have any interest in setting himself or his team on autopilot.  Instead, he began to look at the market and consider how he could offer something new.  “At that point in time, you had two extremes in the software industry,” he says.  “You had the large, offshore, outsourcing model, or you had the exact opposite, which is what we were—a boutique of high performers that were rapid time-to-market, high innovation, high quality, but hard to sustain.  We had a project-based business.  We’d come in, clean up a mess, and then have to move on to the next thing.  My thought was, what if you could combine these two extremes?”

The result?  A completely unique business model that David refers to as shore-agnostic.  “It’s not off-shore, it’s not on-shore, it’s the right shore,” he avows.  “It’s all about building software products in a way that gets those products to market in a rapid time, leveraging the greatest technologies but also leveraging the global talent base.  If you understand the strengths and weaknesses of each geography and each location, as well as the skill sets, you can build a high-performing team that’s both virtual and global, and you can leverage the cost advantages of different economies without basing your entire value proposition off of it.”  Shortly after he envisioned this model, David acquired a Romanian off-shore company, and the following year, saw 50 percent growth.  “It proved that the market was hungry and ready for that model,” David continues.  His ability to integrate the two existing models in the software development market produced an entirely new animal—one the clients were eager for.

“More than anything, ours is a story about continuing to adapt and continuing to refine our strategy,” says David, reflecting on the company’s unexpected genesis.  Initially, he hated the concept of off-shore development, having seen it fail often.  But instead of rejecting it out of hand, he instead found a way to do it better.  “It’s about being confident in your ability to get to the next level, but humble enough to listen to what people around you are saying, filtering it to the extent you need to without being so proud that you think you’ve got the solution,” he says.  “With outsourcing, I started to see that there was a real business reason to leverage the global economy.”  Keeping his ears and eyes open, he was again able to integrate two opposing ideas to produce a viable solution.

David’s unique approach to leadership, success, and adaptability stem from his childhood, which was rife with constant change.  His father was an officer in the Air Force for thirty years, which meant the young boy changed schools more often than he changed grades.  “I probably attended 9 or 10 different schools in total, and an astonishing 5 high schools,” he muses.  “This upbringing cultivated in me a strong sense of leadership and integrity, but at the same time, the ability to be agile and to respond quickly to changes in my surroundings.”

David also developed a precocious maturity that grew out of necessity.  “I remember hosting a Senator at our house at one point in time, and I remember meeting Vice President Bush as a kid,” he explains.  The middle of three children, he also took on a fatherly role to the youngest of the DeWolf children—his baby sister, 15 years his junior.  And though his father certainly honed his leadership skills, David is quick to credit his mother as well.  “I think the biggest thing I learned from my mother was compassion,” he avows.  “It has truly shaped the culture of our organization.  One of the values that is absolutely critical to me is how we treat our employees, respecting the dignity of each person.”

David’s leadership skills were further honed during his years at Franciscan University, a Catholic college in Stubenville, Ohio.  With its emphasis on faith and charity, the school reinforced his parents’ teachings, affirming the tenets of compassion, adaptability, and integrity that would become so vital to 3Pillar down the road.  David majored in communication and audio/visual productions, vaguely hoping to go into music production, but when he graduated, he quickly reassessed that career path.  He was six months from being married, and he realized he needed a more reliable profession to support a family on, so with his trademark ability to reorient and adapt, he found a job with an advertising agency.  There, he began building a website for a software company, where he fell in love with writing software and found a mentor, John Fowler.  “He was the strongest software engineer I’d ever worked with, and for whatever reason, he took me under his wing and taught me the ropes of that industry,” says David.  “Within three months, I went to work for that company.”

A few years later, with two small children in tow, David and his wife moved to the DC Metropolitan area in search of a strong Catholic and home-schooling community.  Now the proud father of six, David maintains that his life is about integration, not balance.  “Balance is a term that really has no meaning to me,” he explains.  “It implies a division between the different aspects of one’s character that I find unhelpful.  I’m a father at all times during the day.  I’m a husband even when I’m in the middle of a meeting.  I’m a CEO even when I’m at home, at bedtime.  Integrating the spheres of one’s life enriches them.  I’ve taken my two oldest children on business trips and had them sit in on meetings, which in turn helps them grow.  And always, we care about people as people.  Our employees can count on 3Pillar to take care of them and stand by them even if they fall on hard times.  That’s just who we are.”

At the end of the day, these are the crucial values David hopes to promote in the world—an effort he continues through serving on the Board of Trustees at Franciscan University and assisting the Catholic Church with leveraging technology and media.  He’s also on the Board of Advisors for a convent in Ohio and, together with his wife, supports philanthropic causes such as an outreach ministry that works to help Catholic students navigate the challenges of college life and a healthcare organization that provides integrated healthcare services to those in need, including underprivileged mothers.  In the future, he hopes to devote more time to training business leaders and entrepreneurs, imbuing them with the same commitment to integrity and humility he practices at 3Pillar.

To those young people entering the working world today, David’s advice is simple.  “Follow your heart,” he says.  “Do what you’re passionate about.  You should wake up every morning and be excited about the day.  If you’re an artist and you love art, go be an artist.  You might not make the most money, but then again, you just might!  What you’re passionate about will be what you’re most successful at.  My wife makes fun of me because I don’t have a hobby, and I tell her, I do have a hobby—I just get to do it as a full time job.”

David’s reliance on a humble confidence took him on a strange but wildly successful adventure, and with that in mind, he also stresses the importance of listening to what others have to say.  “A lot of people will talk about how entrepreneurs have to be hard-headed and stubborn, not listening to the naysayers, but I think that misses a really big part of what it is to be successful.  You absolutely have to have confidence, but you have to be humble enough to listen, to hear the feedback out there in the world, to filter it and apply what’s necessary, and to adjust as necessary.  It’s not all about you—it’s about the team you create and what you can achieve together.”

David DeWolf

Gordon J Bernhardt


President and founder of Bernhardt Wealth Management and author of Profiles in Success: Inspiration from Executive Leaders in the Washington D.C. Area. Gordon provides financial planning and wealth management services to affluent individuals, families and business owners throughout the Washington, DC area. Since establishing his firm in 1994, he and his team have been focused on providing high quality service and independent financial advice to help clients make informed decisions about their money.

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