County Executive Rich Fitzgerald with Twitter CEO Jack Dorsey. Photo by Tracy Certo.

The elevator ride to the 17th floor of the William Penn Hotel hinted that this wasn’t your standard Pittsburgh technology event. With each stop, young adults wearing Twitter T-shirts entered and continued to focus and tap on their phone screens. The elevator emptied into the crowded hallway and ballroom where a diverse crowd was eagerly awaiting the event: Breakfast with Jack Dorsey, (@jack), co-founder and CEO of Twitter.

Accompanying him was the dynamic Candi Castleberry Singleton, (@candi), a popular figure in Pittsburgh who led the Dignity & Respect campaign here and who recently  moved to San Francisco to become Twitter’s VP of Inclusion and Diversity.

Castleberry Singleton interviewed her boss Dorsey on topics ranging from personal social media use to diversity in the workplace and how Twitter’s @TwitterTogether program is approaching the issues. Dorsey was in town for the Black Engineers Convention underway at the same time.

The event was hosted by the Pittsburgh Technology Council, Vibrant Pittsburgh and Morgan Lewis.

The pair shared that Twitter is focused on intersectionality and culture, which they defined respectively as “making connections with people unlike us” and “where people of  different backgrounds feel welcome.”

Twitter has been in existence for 12 years, noted Castleberry Singleton. So what makes Dorsey the proudest?

“We have seen so many grassroots movements arise and use the [Twitter] platform to amplify those movements,” said Dorsey in a low-key delivery. “Although there have been dark moments, every week, we see something we never expect to see.”

Tweet by Kenny Chen of Ascender/Thrival during the Dorsey event.

As examples, he mentioned Saturday’s March for Our Lives which grew out of a small group of students who survived the shooting at Marjory Stoneman Douglas High School in Florida. Another example he cited: Golden State Warriors center Draymond Green’s mom, who according to Dorsey, provides some of the best perspectives on NBA games by trash talking the competition and her own son.

Dorsey’s own mom, @marciadorsey, is his favorite follow because she has developed a group of followers who treat Twitter as a big text messaging system, offering morning greetings with photos of sunrises to one another.

Candi Castleton Singleberry taking a group selfie of the Twitter crew. Photo by Tracy Certo.

Other questions came in about growing Pittsburgh’s tech economy, how Dorsey and Castleberry Singleton manage their social media and how Dorsey successfully runs two billion-dollar companies concurrently (Twitter and Square, where is also CEO).

When asked whether Dorsey thinks Pittsburgh will evolve into a tech hub that will draw Silicon Valley companies to migrate here, he said he often gets the question about how to replicate Silicon Valley in various cities. His advice to Pittsburgh: Don’t replicate Silicon Valley, but use Pittsburgh’s unique strengths instead to grow the economic base.

On their social media usage, Castleberry Singleton and Dorsey were far apart. She said she has trouble putting down her phone and disconnecting from social media’s constant draw; he said he has ditched his computer and his iPad in favor of only an iPhone and puts his phone in the kitchen each night at 9:30. He does not pick it up again until the next day after he has meditated and exercised.

For entrepreneurs who are looking for guidance on how to grow their companies when their schedules seem out of control, Dorsey shared that he changes his technique from time to time. Currently, he starts his days with meditation, then exercise, then coffee.  He then walks five miles to work while listening to podcasts or audiobooks. That way, no matter how bad his day might be, he has already won because he has exercised, learned something and given himself personal time.

As one entrepreneur said, “If Jack Dorsey can do this, why can’t I?”

David Radin is CEO of Confirmed ( For decades, he has been leveraging technology and techniques to transform the way his audiences and clients succeed.