0:00
/
0:00
Transcript

Tim Huelskamp | The Curious Connector | The Flywheel of Employee Delight

By Johnny Levy, Workplace Delight

I sat down with Tim Huelskamp, co-founder of 1440—the wildly successful daily newsletter with over 4 million subscribers—and walked away convinced: the man sees business through a radically human lens. His secret? Build a culture of delight by obsessively caring for your people—and then get out of their way.

Curiosity as Core Strategy

Tim's passion for learning is the engine behind 1440. “We love diving in and going down the rabbit hole... then serving others by sharing what we learned,” he told me. The company’s internal principles reflect that, including mandates like be a lifelong learner and obsessively know, serve, and delight the customer—which, as Tim points out, “really is just another form of curiosity.”

Three Qualities They Hire For

When I asked what he looks for in new hires, Tim gave it to me straight: “We call it intellectual horsepower, loving the work, and cultural fit.” And he lives it. “I interview every person we hire,” he said. “I want to feel their passion through the Zoom.”

Profits Follow People (The Flywheel)

Tim flipped the old business playbook on its head. Instead of squeezing people for profit, 1440 invests in their people—and the profits follow. “You can’t deliver for your customers unless your employees are delighted and inspired to do their best work,” he said. “If we’re profitable, we reinvest it into our people—and it becomes a flywheel.”

A Benefit Package That’s Built With Love

My jaw dropped when he listed just a few of the benefits:

  • Proactive raises before anyone has to ask

  • Body scans for early detection of health issues

  • $500 for every child’s 529 college fund on their birthday

  • 16 weeks paid parental leave

  • Sabbaticals after five years

  • Happiness check-ins each quarter where the employee reviews the company

As Tim put it, “We’re constantly trying to create the kind of workplace we’d want to work at ourselves.”

The Human Factor

Tim's leadership model is rooted in personal connection. “I know everyone’s name, their kids’ names, their dreams,” he told me. “It’s not scalable forever, but it’s critical now.” And even as they grow, he wants to maintain that sense of care and clarity. “We call ourselves ‘froleagues’—friend-colleagues—because we like each other and we love the work.”

Long-Term Thinking Wins

His final insight struck deep: “Taking care of people is the best way to do business. Maybe not for 2024 profit margins—but for 2029, 100%.” The old transactional, zero-sum model of leadership is shortsighted. Long term profitability comes form delighted people who delight the customer.

To Tim and the team at 1440: thank you for reminding us that employee delight isn’t fluff—it’s the foundation of thriving companies.

Subscribe at workplacedelight.substack.com/subscribe if you are a business leader, consultant, provider, or HR professional devoted to surpassing employee success and creating employee delight.

Discussion about this video