Podcast

Bearchats by Bearworks #1: David Lanstein's Lessons from Chamber Music, the NFL & Silicon Valley

Luis M.

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Bearchats by Bearworks #1: David Lanstein's Lessons from Chamber Music, the NFL & Silicon Valley

Sales isn’t just about closing deals. It’s about resilience. The top performers know how to handle rejection, adapt fast, and turn every challenge into an opportunity.

In this kickoff episode of Bearchats by Bearworks, Albert sits down with David Lanstein and Sarah Hoskin to break down:

  • The mental toughness needed to thrive in sales.
  • How top sales reps turn setbacks into stepping stones.
  • Why airplanes might be the best sales tool you’ve never considered.

Tune in now to learn how to build a winning sales mindset.

From Chamber Music to Sales Mastery

David Lanstein’s journey into sales is anything but typical. Starting as an orchestra musician, David’s early career revolved around high-stakes performances with world-class ensembles. But as he explored his next steps, a childhood exposure to programming led him into Silicon Valley. After a technical role at Splunk, a logging company that was acquired by Cisco for $28B in 2023, he made an unconventional leap—diving headfirst into sales.

His motivation? Sales wasn’t just about persuasion—it was about knowing the product inside out and solving real problems. David believed that a deeply technical sales team could outperform traditional models, and his career as the first salesperson at PagerDuty (NYSE: PD) proved that theory right. With his co-founder, he spearheaded the company’s first $7 million in revenue, eventually scaling it to IPO.

Grit, Rejection, and the Art of Selling

One of David’s most defining traits is his relentless resilience—something he saw mirrored in unexpected places, like the NFL.

He shares the story of hiring Eric, a former pro football player with no sales experience. What Eric lacked in traditional training, he made up for in grit, adaptability, and work ethic—traits honed by surviving NFL training camps. Under David’s mentorship, Eric became a standout enterprise sales rep, proving that mental toughness often outweighs industry experience.

His takeaway? Talent can be taught, but resilience and curiosity separate the best from the rest.

Why Airplanes Might Be the Ultimate Sales Tool

David swears by in-person meetings, traveling nearly 48 weeks a year to close deals. His philosophy? Strong business relationships are built face-to-face.

“Hard negotiations or building rapport—nothing replaces being in the same room,” he says.

For David, sales isn’t just about pitching—it’s about understanding what both sides truly want and crafting win-win solutions.

Key Takeaways from Episode #1:

  • Sales is a mindset. Whether you come from a technical background, sports, or music, resilience is your greatest asset.
  • Hard work beats natural talent. Grit, adaptability, and curiosity are the true differentiators in sales success.
  • Face-to-face matters. In an increasingly digital world, human connection still wins deals.

Show Transcript

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