I didn’t set out to study how customer obsession fails. But after watching my third founder friend in two years step down because they couldn’t scale their customer relationships, I started seeing a pattern.
Over drinks last month, Sameer (name changed) told me how his Series A startup was being restructured by the board. “They said I was spending too much time with individual customers and not enough on building systems,” he said. “But those relationships are why we even got this far.”
He’s not wrong. And neither was the board.
After dozens of conversations with founders in similar positions, I’ve realized we’re missing something crucial in how we talk about customer obsession. It’s not one trait but two fundamentally different orientations that often work against each other. And the most painful founder transitions happen when they can’t bridge this gap.
Monica built a fintech app for freelancers that users absolutely loved. Her customers would email her directly with problems, and she’d often stay up until 3am coding fixes. When someone was frustrated, she felt it viscerally. This deep empathy helped her build features her competitors missed entirely.
When they hit 50,000 users, things fell apart. Support tickets piled up. Monica was still personally responding to dozens of customers daily while trying to manage a growing team. Key metrics started slipping. Major bugs went unfixed because she was buried in one-off issues.
“I knew we needed better systems,” she told me. “But every time I tried to pull back from direct customer contact, I’d see problems that nobody else noticed. So I’d jump back in.”
Six months later, they ran out of runway. When I asked what she’d do differently, Monica was blunt: “I’d have hired someone who loves building systems as much as I love talking to customers.”
David’s story is the mirror image. A former McKinsey consultant, he built a B2B workflow tool with meticulous customer feedback processes. Every feature was prioritized through rigorous analysis of support tickets and feature requests. His systems were impeccable.
When they raised their Series B at a $120M valuation, investors were impressed by their operational excellence. Customer satisfaction scores were consistently above industry averages.
But six months later, their biggest enterprise clients started quietly switching to a newer competitor with fewer features but a more intuitive experience. When David finally got on the phone with a former client, the feedback stung: “Your product does everything we asked for, but somehow misses what we actually need.”
The competitor had been founded by a former customer success representative who didn’t have sophisticated systems but had spent thousands of hours directly experiencing customer frustrations. He built from intuition what David couldn’t capture in metrics.
David’s company was acquired in a fire sale for $80M below their previous valuation.
Monica and David’s failures weren’t random—they revealed a fundamental misunderstanding about customer obsession itself. After analyzing these and other cases, a pattern emerged that I’ve now seen repeatedly. There seem to be two fundamentally different modes of customer obsession:
Empathic Obsession: Founders who develop intuitive understanding through direct immersion. They feel customer pain viscerally, often can’t articulate exactly how they know what customers need, and build based on emotional connection more than explicit requests.
Systematic Obsession: Founders who develop comprehensive understanding through careful analysis. They build structured feedback mechanisms, track patterns across large numbers of interactions, and pride themselves on making decisions based on aggregate data rather than individual feedback.
The problem? Most founders are strongly oriented toward one mode and actively resist the other. And different stages of company growth require different modes.
After mapping the trajectories of dozens of startups, I’ve noticed that successful companies navigate three critical phase transitions:
0-1: Customer Discovery Early-stage companies need deep empathic obsession. The founders who excel here are often described as “customer whisperers” – they pick up subtle cues that formal research misses entirely.
Karen, founder of a $400M health tech company, spent six months shadowing nurses before writing a single line of code. “I needed to feel their frustration in real-time,” she explained. “No survey could have shown me what was really happening.”
The systematic founders who succeed here do so by compensating heavily. Alex, an analytically-minded founder who built a $2B enterprise software company, forced himself to handle all customer support for the first year. “It was excruciating,” he admitted. “But I knew I’d build the wrong thing otherwise.”
1-10: PMF Scaling This is where the first painful transition occurs. As customer numbers grow, pure empathic obsession starts breaking down. The founder can’t maintain direct relationships with everyone, yet the systems aren’t mature enough to capture the nuances.
This is where Monica’s startup failed. But others navigate this transition successfully by developing a hybrid approach.
Jamie, founder of a popular consumer app, explained her solution: “I still spend 20% of my time with individual users, but I’ve built a structure where those insights feed directly into our product process rather than becoming one-off fixes.”
10-100: Experience Systematization As companies scale further, systematic customer obsession becomes essential. But the most successful companies find ways to maintain the empathic connection that got them started.
Stripe is the master case here. Despite serving millions of customers, they’ve retained their empathic obsession through creative systems. Their “support shadowing” program requires every employee—including executives—to regularly handle support tickets. This keeps customer pain visceral while still allowing for systematic improvement.
This is where David’s company failed. His systems were excellent but had become disconnected from emotional reality.
These aren’t minor optimization problems. The stakes are existential.
In my analysis of 19 founder journeys from my network and investor portfolio between 2019-2023, I found that 83% of those who raised a Series A but failed to raise a Series B cited the same core issue: they couldn’t transition their customer approach to match their company’s growth stage.
Either they:
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Remained too immersed in individual customer relationships and couldn’t build repeatable systems (Monica’s problem)
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Built sophisticated systems that lost touch with the emotional core of customer needs (David’s problem)
The founders who successfully navigate these transitions don’t magically become ambidextrous. Instead, they develop specific bridging strategies:
For Empathic Founders
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The Customer Council: Sara, founder of a $300M D2C brand, created a formal customer council that meets monthly. “It lets me maintain the deep connections I need while creating a system around those insights,” she explained.
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The Interpreter Partner: Raj, founder of a fast-growing fintech, partnered with a COO who excels at systematization. “I still do what I’m best at—feeling customer pain—but Tom translates my intuitions into scalable processes.”
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The Immersion Schedule: Wei, founder of a B2B SaaS unicorn, blocks every Thursday for direct customer interaction, no matter what. “It’s sacred time. The company knows those days I’m unreachable for anything else.”
For Systematic Founders
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The Empathy Injection: Carlos, founder of an analytics platform, hired former customers into key product roles. “They bring the visceral understanding I struggle to develop naturally,” he admitted.
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The Unfiltered Feed: Lisa, founder of an enterprise software company, created a Slack channel where customer-facing employees share raw customer comments daily. “I needed emotional contact with customer reality, not just the sanitized metrics.”
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The Beginner’s Mind Practice: Michael, founder of a successful API company, does quarterly “customer shadowing” where he watches new users interact with his product without intervention. “It’s painful to watch them struggle, but that pain keeps me honest.”
The most striking pattern in my conversations? The profound resistance founders have to acknowledging their weaker mode of customer obsession.
Empathic founders often view systematization as “corporate” or “losing touch.” Systematic founders often see empathic approaches as “anecdotal” or “lacking rigor.”
This blind spot becomes increasingly expensive as the company grows.
Mark Zuckerberg may be the ultimate case study in overcoming this resistance. Naturally systematic in his approach, he realized Facebook was losing touch with user experience. His solution was radical: he mandated that every employee (including himself) must use Android phones to experience the app as most global users did—often with slower connections and different interfaces.
This wasn’t just symbolic. It created visceral empathy that metrics couldn’t capture, all within a systematized framework.
After seeing these patterns, I’ve started asking founder friends these questions:
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Which customer obsession mode feels natural to you? Which feels like work?
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What’s one concrete way your current stage requires the mode that’s unnatural to you?
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Who on your team excels at the opposite mode from you? Are they empowered?
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What systems or practices have you built to compensate for your natural orientation?
The most successful founders I know can answer these clearly. The struggling ones often can’t.
I’m still learning here. My sample size is limited to my personal network and the founders willing to share their struggles.
I’d love to hear from more founders about how you’ve navigated these transitions. Did you naturally excel at both modes? Did you find a bridging strategy I haven’t covered? Or did you struggle with exactly this challenge?
The stakes are too high for us to keep pretending that “customer obsession” is a single skill rather than two fundamentally different orientations that often work against each other.
Let me know your experiences by sending me a DM or leaving a comment.
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