The Practices Fueling Chartbeat’s Tony Haile to Scale as a Founder

The Practices Fueling Chartbeat’s Tony Haile to Scale as a Founder

The Practices Fueling Chartbeat’s Tony Haile to Scale as a Founder 1600 900 33Voices

Despite running a successful venture-backed startup, being a karaoke champion, and even competing in a round the world yacht race, Tony Haile has unfinished business. An extreme adventurer at heart, he needs to achieve his goal of walking to the South Pole. 

I was shocked when I first read about Tony’s quest. After spending time with him, it quickly became clear that the inexplicable challenge is fitting to his relentless commitment to self-improvement. 

Whether it’s embarking on a polar expedition, or leading his startup Chartbeat on the audacious journey to “save journalism,” as  Alexis Sobel Fitts highlighted in the Columbia Journalism Review, Tony’s highest goal is to be better, faster. 

“It’s not about 10,000 hours of doing something,” he explained, citing Dr. K Anders Ericsson. 

“It’s about 10,000 hours of deliberate practice where you do something, you observe what you did, and adapt to be different next time.”

“That’s what I am trying to do with my job. I need to get better.”

The people who work at this company require and deserve that I am better than I am today.

The only way to navigate that evolution is exercising “constant vigilance” as CEO. 

As Chartbeat aims to hire their 101st team member, Tony’s highest responsibility is that each individual feels excited, reassured, and prepared for growth.           


“The 50th employee hired is worried about how the culture will change when the 60th person comes through. What they don’t realize is that the previous 49 people were worried about how they would change the culture,” he said. 

Culture is never static. If culture is static, it’s dead.

“It’s not about becoming homogeneous. It’s about people coming in and giving their very best.” 

“Culture changes, becomes richer, and more nuanced. Every single person adds a thread to that tapestry.”

To ignite your team’s potential each individual needs feels that his or voice is heard as the company scales. 

This is especially important for cultures that are strongly driven by a single department like product, design, or engineering. 

“It’s great to have a product or engineering driven culture, but it means that other parts of the company are lessened.”

Every single part of the company has an important voice.

For example, your sales team is “radar for product. They know things you can’t know sitting in the office.”

Your job as CEO is “to make sure there is a good balance.” 

Numerous operational changes will occur through the lifecycle of your company. It’s important to keep meaningful traditions and procedures constant.

At Chartbeat, every six weeks the team has a company-wide hack day.  The creative and collaborative events inspire some of the team’s best ideas. 

Additionally, conversations are still held in open spaces. Whether physically or on a digital platform like Slack, this promotes accessibility and transparency. 

Honesty is the foundation of Chartbeat’s culture and Tony’s leadership style. 

His first conversation with every new team member emphasizes the influence they possess shaping the organization and their personal role. 

While it’s telling to encourage your team members to share challenges and celebrations with you, assert when you have insufficient information, or that the team should be going in a different direction, the sentiment is meaningless unless you listen to and evaluate their feedback. 

“Your job is not only to do your job it’s to help me do mine,” he expresses to them. 

In Tony’s seven years leading Chartbeat his most profound leadership lesson is “is the importance of shutting up.”  

“When you’re first starting you have this deep sense that you should be in every meeting and immediately have an answer or opinion.”

50% to 75% of the time you’re saying something for the hell of it.

“Calm down. Have more security. Listen to people and say thank you when they are finished.” 

“You don’t need to add your two cents.” 

Listening, digesting feedback, and preparing to address a situation is the difference between responding and reacting.

Whether it’s a product feature or Chartbeat’s annual goals, Tony’s adamant about thinking through plans and possibilities before making decisions. He even asks team members to provide an in-depth agenda before meetings so he can give them his best. 

“We have two modes of thinking,” he explained. 

“System one: Our fast, reactive thoughts. And, system two, which is our deep computing power.” 

“If you haven’t thought through something before, your system one is going to be doing the thinking when you need it to be your system two.” 

To combat his system one thoughts he writes down the challenges, goals, and situations he faces on a daily basis to gain a broader perspective and consider long term possibilities.

Writing fuels your system two thinking and enables you to make thoughtful decisions. This is especially important during stressful situations when Tony cites that after writing and revisiting his thoughts his response is “180 degrees different.” 

“I have 100 people who I love and care about. I don’t have the luxury to aimlessly react.”

The only way to ask someone for their very best is to give them yours.

To gain deeper insight into Tony’s efforts leading Chartbeat – including his extensive reading list and details on his polar expeditions – tune into his episode of Beyond the Headline and follow him on Twitter here.

Images retrieved from The Muse.