February 4, 2019

How The Son of Black IBM Engineers From the ’60s Became a Tech CEO, Who Helped Fix Healthcare.gov

Truss.works are hiring on pocitjobs.com

Everett Harper’s story in tech began long before he helped healthcare.gov achieve its ambitious mandate of registering 1 million Americans by the end of 2013. At the start of the interview, Everett talks fondly about his parent’s career trajectories. 

“I was raised in a family of IBM engineers back in the ’60s. Neither of my parents went to college. They were programmers. IBM was one of the first companies to hire African Americans in any kind of white-collar technical role – at any scale or number.

As Everett wrote on Forbes, his mother, Jackie Harper, had an illustrious programming career spanning 25 years. Everett’s father – Jim Harper – was a systems engineer guy who started of in the navy. Both of them faced incredible odds as African Americans. 

But Everett’s story isn’t one of emulation. ‘There are born engineers and I’m not one of them’ he says. ‘I finished the degree, but I couldn’t see the patterns like other people could.’  After graduating, Everett worked at Bain & Company, a prestigious management consulting company in Boston, for two years. ‘But that wasn’t it either,’ Everett says.


What followed was a period of trial-and-error in different industries that would equip him with the rare ability to empathize and work with very different people, and to identify business opportunities everywhere .

‘We were innovating in some loan products,’ Everett says, having found his way into a community development finance company. Self-help Credit Union was a pioneer in enabling low- and middle-income families access to financial tools, especially on housing. ‘I got a chance to lobby for a year,’ he says. ‘I learned more about human nature, about how to understand the complexity of doing a deal or making something happen.’

In 1991, he founded his first company, Harper Associates, a diversity consultancy in North Carolina – a hard job, which consisted of merging previously segregated schools together in North Carolina, where the legacy of the Ku Klux Klan remains. ‘There were death threats’, Everett says. ‘So you have to figure out how to work with people that have histories that you don’t agree with.’

After the consultancy, he went to do an MBA at Stanford University graduating in the middle of the first dot com boom. Having decided to venture into tech, he got a job at Second Life, a virtual reality social platform very popular between 2005-08.

When he left in 2008, he readily jumped on the iOS app economy boom and co-found a wine app called Bottlenotes. With both founders being non-technical, they relied on outsourced consultants. The first consultant, Everett recalls, ‘literally didn’t even show up for a super important meeting’.  Eventually, both co-founders burned out from the experience called it quits. ‘We had such high hopes,’ Everett exclaims. ‘And we realized we did not know what we were doing in so many ways.’

Fixing Healthcare.gov

Mark Ferlatte [his co-founder and lead engineer] called Everett at 7 pm on a Sunday. Mark was one of his co-founders for Tetherpad [a bootstrapped mobile travel managment app], Everett’s next venture after Bottlenotes. They had been colleagues in Second Life.

“Everett, the CTO of the United States wants me to go work on healthcare.gov.

Mark just had received a call from USA’s CTO. Healthcare.gov was in crisis. The government had spent $200 million on a system that remained unusable since its launch. 

“Obama had bet his second term on this. If this had failed, then his whole presidency would have been put to question.

This telephone call between Mark and Everett lasted 90 seconds. ‘You gotta go,’ Everett responded to Mark. ‘We got your back man. We’ll figure it out’

‘This was important for society. That made it easy to decide. Even though we didn’t know what the answer were…’  Everett recalls

Pivoting & Building Truss

Soon after there experience helping healthcare.gov Everett and his team pivoted Tetherpad into what Truss is today: a Software Engineering, DevOps and Infrastrucutre consultancy, helping companies and government agencies navigate the complex challenges of growth and transformation.

Pulling from his experience at Self-Help Credit Union, Everett says:

“One thing I learned from that was about leverage. About how you can take a small company, apply knowledge in a very specific way, demonstrate it, and then hand that off to a larger entity that can take that innovation and really blow it out to the wider world.

To Everett, an infrastructure-first approach is not only optimal in technology, but also in life.

As he penned on Forbes, a culture of innovation is not enough. The real innovation is in the process, not the product.

Tips for young people who want to start a career in tech

Everett imparts some tips and advice to young people who want to begin a career in tech.

1. Networking matters and you need to do it right

‘Networks matter,’ Everett says. ‘especially when you want to start a company.’ Indeed, he met his Truss co-founders during his time in Second Life.

Everett gives out important advice to young people of color in particular: ‘The POC and black community network is strong,’ he says, ‘but you also have to reach outside of that network.’

But Everett warns that networking in a transactional way [pitching etc]  mostly never works. Rather connect with them as humans first. ‘Connect with people on something that they actually care about’.

2. Dive into the deep end

Everett wants young people to take more risks by showcasing themselves and be more entrepreneurial:

So even if it’s a small risk to say, “I’m going to give a talk,” or, “I’m going to do a side project,” or, “I’m going to try and go for this position that I’m not sure I can get.” What it’s doing is training you to be in the arena, as Brené Brown likes to talk about. Being in the arena doing your best, getting knocked down, because you’re going to get knocked down, hard, and learning how to get back up again.

3. Stay resilient

Everett has also faced a series of personal struggles, in addition to his professional ones. In the face of adversity, Everett encourages people to stay resilient but to also give themselves to face things at their own time. If feeling grief is necessary, then grieve. But get back up. As he says:

If you’ve gotten knocked down and you get back up, by the time you go find a company, or take on a really serious role, there’s a lot of confidence that comes from, “You know what? I know how to get back up again.” So find ways to put yourself in that position, and then create the support network around, and then people can pick you up the first couple times.

4. Do something that keeps you curious

He encourages people to find and master a craft that interests them:

“You don’t have to know it for the rest of your life. Do one thing that’s so compelling, so interesting, that you’re probably going to get pretty good at it.

Truss.works are hiring on pocitjobs.com.
Julian Canlas

Julian is a tech writer, specialising in community-first SaaS content strategy and narrative journalism

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