Two weeks into his freshman year at Harvard, David G. Ewing tore his Achilles tendon clean in half. The football career he had been recruited for ended before it started, and he spent the next year learning to run without a limp. That early gut check became the pattern for everything that followed. A cancelled future in his family's Detroit manufacturing plant. A tech startup that imploded in the dot-com winter. A first employee hired on September 10, 2001. Every time a door closed, David figured out what he still had and kept moving.
What You'll Hear
- Why David calls himself a wannabe tech bro and how he runs two companies at once
- The senior-year conversation with his dad that killed his plan to join the family manufacturing business
- How he landed his first consulting client the day after the dot-com crash wiped out his savings
- Hiring his first employee on September 10, 2001, and what he almost did the next morning
- The yoga studio contract that taught him consultants need a system, not just smart opinions
- How a 2008 Oracle road show vaulted his firm from small clients back into the Fortune 500
- What he learned from Molly Bloom about talking back to the voice in your head
- The one habit he says saved him from robbing himself of joy
Two companies, one through line
David Ewing runs two businesses, Motive and Content Lion, and he is candid that the dual CEO routine has given him a new appreciation for how hard that job is. The two companies are not random bets. They share a customer, a technology stack, and a story.
Motive is a software services firm focused on customer lifetime value. Large high-growth companies hire David's team to work the mechanics of getting existing customers to buy more often, spend more per transaction, and stay longer. The work is heavily technical. Most of it sits on top of Oracle's stack, which David picked because it scales cheaply and Oracle spends roughly 4.5 billion dollars a year on research and development.
Content Lion grew directly out of that work. Oracle used to sell a product called Oracle Content Management, which Motive implemented for clients. When Oracle decided to sunset it, David looked at the alternatives, did not like what he saw, and partnered with Oracle to build Content Lion on their cloud infrastructure as the replacement. Motive now uses Content Lion on its customer projects. That is the synergy that makes running two companies possible instead of exhausting.
Harvard, a torn Achilles, and a game he still plays in his head
David grew up in Detroit and was recruited to play football at Harvard. He almost blew the recruiting call because he thought the coach said Haverford and answered like a distracted 18 year old with a video game controller in his hand. Two weeks into freshman year, his Achilles tendon rolled up like a Venetian blind. He was on crutches for ten weeks and it took a year before he could run without a limp.
Instead of spiraling, he ran an exercise he still uses. He imagines he has just parachuted into the body of David G. Ewing, today is day one, and asks what he actually has to work with. The answer at 18 was that he was at Harvard with a cast on his foot, which is not, he points out, the worst place to be stranded. He took classes at Harvard and MIT, met professors like the chemist who discovered the ozone hole over Antarctica, and kept building.
He uses the same trick now. When the present feels overwhelming, wipe the slate, inventory what you have, and move. The practice shows up later in the conversation almost every time a door closes on him.
The senior-year conversation that killed the backup plan
Every summer during college, David worked in the Detroit factory his dad and uncle ran. Heavy metal bending, rapid tension bolts, piston pins, parts for the heartbeat of America. He loved it and assumed he would join the business after graduation. He had three or four years of plant experience by the time he was 21.
Midway through senior year, his dad flew out, knocked on his door, and told him he could not come work at the factory. The reason was simple. His dad planned to sell the business. David would end up a mid-level manager working for whoever bought it, and the specific skills he had built would be worth less than he thought. Find something else.
David describes the moment as his career blowing up before it started. Looking back, the lesson was not about his dad's decision. It was that his plan had been entirely outside his control and he had put every egg in one basket. He tries to skip past what-ifs because they are a waste of time. Take the lesson, leave the regret, move on. He picked up a copy of Popular Mechanics in Harvard Square, started cold-calling cover stories, and ended up at a boutique Silicon Valley venture capital firm called RB Webber that combined investing with hands-on consulting for the companies it backed.
Starting a company with a week of severance and a first employee on 9/10
David wanted to be an operator, not a consultant on the sidelines. In February 2001, the tech startup he had joined imploded along with the rest of the dot-com market. He had a week of severance, a San Francisco rent bill, and not much saved. Angel investors and friends and family all passed on funding a new software company.
Then the phone rang. Someone in his network had heard he was down and asked if he would consult for them. He took it as a sign, started San Francisco Consulting Group the next day, and was cash-flow positive on day one. Two more calls came in that week. He had three clients before the weekend.
He hired his first employee on September 10, 2001. The next morning he had payroll to worry about and a gut-check decision to make. He stayed with the business, betting the response to 9/11 would be shorter than it turned out to be. 2002 and early 2003 were brutally lean. Nobody was investing. He took any contract he could find, including a yoga studio in San Francisco where he helped pack more bodies into classes by staggering mat placement on the floor. The lesson from that stretch was that small advantages, executed consistently for clients who will actually use them, compound.
Why David hires consultants who have a system, and how a 2008 Oracle road show changed everything
The yoga studio story leads into one of the sharper arguments in the conversation. David argues most consultants sell smarts and vibes. The ones worth hiring sell a system. He tells the story of an executive coach he hired in his 30s who had a six-month program built on personality diagnostics and mental modeling. He came out a different operator. When he asked what was next, she offered another six months at the same rate with no system behind it. Same person, same skill, but she was over her skis. The value had come from the system, not the smarts.
His test when a consultant pitches him now is simple. Do you have a system, a tool, an asset that will produce an outsized result that I could not get from hiring another bright employee? Going through the process itself has to deliver value, because no one can guarantee the outcome. If the only thing on offer is a pot of gold at the end of the rainbow, pass.
He used that same discipline on his own business. From 2005 through 2007 he codified what he had been doing on paper into a technology-backed practice built on Oracle. In 2008 Oracle ran a road show to push back on Salesforce and asked partners which cities had happy customers. David was the only partner with a reference in every city on the list. Overnight he went from an obscure partner to a lighthouse partner that Oracle wanted to put in front of its biggest accounts. He was back in the Fortune 500 he had aimed for out of college, this time as the operator.
What makes companies special is the price they are willing to pay
Toward the end of the conversation, David shares two things he wishes someone had told him earlier. The first comes from chapter two of The Subtle Art of Not Giving a F, which he calls one of the best chapters he has ever read. Everyone has the same dream. Money, looks, walking into a room to a round of high fives. That ambition does not make anyone special. What makes someone special is the price they are willing to pay. Nights, weekends, vacations, the work nobody else wants. Not what you want, what you are willing to give.
The second came from meeting Molly Bloom at an Entrepreneurs Organization event in South Florida. Molly was an Olympic skier whose binding popped on a training run, flipping her 17 times and breaking her back. When she tried to compete again, a voice in her head kept telling her it would happen again. She asked her dad, who was her coach, what to do about it. He told her there is nothing wrong with having the voice. The only thing wrong is not talking back to it.
David says that landed hard. He had spent years letting an internal critic tell him the marketing was not good enough, the solution was not the best he could do, the process was late. No success ever felt like enough. Learning to actually refute that voice and acknowledge what had gone right has been a game changer. He closes on a rule he has lived by since high school. Life is 10 percent what happens to you and 90 percent how you react. A lot more sits inside your sphere of control than most people realize.
About David G. Ewing
David G. Ewing is the CEO of Motive, a software services firm that helps large high-growth companies increase customer lifetime value through Oracle-based technology, and the CEO of Content Lion, an AI-enabled digital experience and content management platform built on Oracle cloud infrastructure. He studied engineering at Harvard and MIT, started his consulting career in Silicon Valley, and relocated the business to Austin in 2011. Content Lion