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

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.

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

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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.

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Episode Transcript

Sarah Hoskin:
Let's just jump into it. Hi David, how are you? Welcome to the podcast.

David Lanstein:
Doing great, doing great. Thanks for having me.

Sarah Hoskin:
So happy to have you here! Let’s start at the beginning—can you tell me a little bit about your sales journey and how you got to where you are today?

David Lanstein:
For sure. I’m not even entirely sure myself—it’s been quite a ride...

(David shares his origin story – musician to programmer to Splunk)

Albert Wang:
So from Splunk, you made the leap into sales—which is not the most obvious jump. What drew you into that world?

David Lanstein:
Yeah, I felt sales was a skill worth having. Especially if you’re technical and understand the product...

(David explains his transition to PagerDuty, working with Mark, building the first $7M in revenue)

Sarah Hoskin:
That’s such a fascinating path—musician to coder to sales! Did it feel like a natural fit once you were in it, or were there moments of serious doubt?

David Lanstein:
Oh, it definitely didn’t feel “natural” at first. It was a big risk...

(David talks about ditching the traditional SE path, combining roles, early motivation)

Albert Wang:
I'm curious—how did you know PagerDuty was the right team to join? Of all the opportunities, why them?

David Lanstein:
It was honestly pretty random. Between Splunk and PagerDuty, I joined Blogly...

(David tells the story of integrating with PagerDuty, being recruited by Alex, the “coffee trap”)

Sarah Hoskin:
Once you made the jump into sales, how did you actually learn? Were you just figuring it out as you went?

David Lanstein:
Oh yeah—tons of mistakes. But it felt like what I was supposed to be doing...

(David shares how technical knowledge helped him sell, CIO meetings at Andreessen, overcoming imposter syndrome)

Albert Wang:
That kind of confidence in the room is huge—especially in enterprise sales. But I’m wondering: how important is it for a seller to be the persona they’re selling to?

David Lanstein:
Great question. I don’t think you have to be super technical. You just have to know what your strengths are...

(David tells story of hiring Eric from the NFL, betting on grit over experience)

Sarah Hoskin:
That’s such a powerful story. What made you believe Eric had what it takes?

David Lanstein:
He wasn’t flashy—he just had grit. Got cut multiple times, stuck with it...

(David explains how Eric learned fast, asked questions, and reinvented himself)

Albert Wang:
Let’s fast forward to what you’re building now. What’s the problem you and your team are solving at Atolio?

David Lanstein:
We’re building the thing we always wanted: Google at work...

(David shares vision: knowledge discovery, secure enterprise search, unifying across platforms)

Sarah Hoskin:
That’s incredibly powerful. Especially when you think about new hires or people leaving and taking knowledge with them.

David Lanstein:
Exactly. Enterprises lose so much tribal knowledge. The system has to be private, flexible, and actually usable...

(David elaborates on product-market fit, security, private cloud, relevance, and why Google/Microsoft failed)

Albert Wang:
You mentioned talking to hundreds of CIOs and CTOs—how did that shape the product?

David Lanstein:
It shaped everything. We realized people don’t just want text or documents—they want answers, and they want to know who to talk to...

Lightning Round

Sarah Hoskin:
Alright David—lightning round time! What’s your favorite beer?

David Lanstein:
Partake Non-Alcoholic Pale Ale. Out of Canada. 10 calories. Delicious.

Albert Wang:
What’s one sales tool you can’t live without?

David Lanstein:
Airplanes. Seriously. I’m probably on a plane 48 weeks a year.

Sarah Hoskin:
Favorite airline?

David Lanstein:
I fly United a lot, so… United.

Albert Wang:
In-person or virtual meetings?

David Lanstein:
In-person. Hard to beat for building rapport and closing hard negotiations.

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