The Outsider’s Advantage: How Fresh Eyes Beat Deep Experience

When I was getting Vital off the ground in 2016, I knew nothing about healthcare.  One of the ways I educated myself was by shadowing my co-founder and brother-in-law, Dr. Justin Schrager, who worked nights in the ER at a university hospital. Before my first overnight, I asked him whether I should wear my favorite shirt or if I’d end up with blood on it. I had a TV-inspired vision of chaos: arterial spurts, trauma bays, emergency drama.

Instead, I saw patients hunched in chairs, miserable with colds and stomach bugs. They were in pain, but forced to wait hours because staff were calmly prioritizing more severe cases. What felt like an emergency to patients was routine triage to the clinicians. It was clear to me that I knew absolutely nothing about healthcare.

But that ignorance turned out to be an asset, not a liability.

Eight years later, Vital serves 7 million patients annually across major health systems like CommonSpirit Health, Mercy Health and Emory Healthcare. We’re in the top 1 percent of all health tech startups. True, I still don’t have the kind of industry credibility I earned in three years at Mint. I walk into meetings with a big “V” for vendor on my forehead, while my co-founder gets immediate respect because he has an MD.

But here’s what I’ve learned: Being an outsider forces you to solve problems differently than insiders ever would. And in industries that are fundamentally broken—which certainly describes healthcare—a different perspective is exactly what’s needed.

Why Industries Need Outsiders

Healthcare has four core problems that insiders accept as unsolvable. First, the economics are backwards: Patients don’t know costs, don’t bear costs and can’t shop for better prices. Second, the threat of lawsuits kills innovation because one doctor saying, “What about this one-in-10,000 scenario?” can kill deals that 19 others support. Third, incumbent technology is 20 years behind because giant electronic health record (EHR) companies use Microsoft’s 1990s playbook of copying innovations and bundling them for free. Fourth, people don’t engage with their health the way they engage with their finances.

Every healthcare insider I meet simply accepts the above as immutable. But I spent years at Mint solving similar problems in finance. The psychological challenges are nearly identical—both industries deal with things that are boring, scary and have dire consequences if ignored. The technical challenges are similar, too: regulated environments with messy, heterogeneous data that needs to be unified into consistent experiences.

The difference is that healthcare insiders can’t see past industry constraints. They know too much about why things don’t work to imagine how they could work differently.

How to Break In: Start by Mapping Your Transferrable Assets

The biggest mistake outsiders make is becoming insiders too quickly. You lose your most valuable asset—your outsider perspective—before you understand how to apply it.

When I started Vital, I spent three years trying to learn everything about healthcare before building anything substantial. In addition to overnight shifts in the ER, I sat through medical conferences, talked to experts and tried to absorb decades of institutional knowledge. That was partly necessary, but it also made me less effective.

• Write down your winning playbook before you learn why it won’t work. Document the specific approaches that succeeded in your previous industry before new industry “experts” convince you they’re impossible to replicate.
  
  
• Separate universal human behavior from industry-specific problems. At Mint, we sent an email to customers every Friday at 5 p.m. intentionally to annoy them. It would tell them: This is your spending this week. Here’s where you went over budget and here’s where you’re under budget before you go out and have a big weekend. People loved and hated it.

The emails solved the engagement problem by forcing people to think about their finances regularly, even when they didn’t want to. They kept users connected to their financial data and made them aware of their spending, before they spent more.

Healthcare experts have said that wouldn’t work for health, but they’re wrong. People’s relationship with boring, important information is consistent across domains.

• Map your technical capabilities, not just your solutions. At Mint, we had to connect to 12,000 banks, brokerages, student loans and mortgages—each with different data formats, connection methods and update schedules. That system was constantly breaking and required 50 percent of our company’s effort to maintain. In healthcare, each health system codes lab tests differently, writes notes differently and has different patient flow processes. The data is completely different, but the core challenge of taking heterogeneous, messy data and creating a consistent user experience is identical. Focus on transferring the architectural thinking, not the specific implementations.

Use Your Ignorance as Market Research

That first night in the emergency room, I had no idea what I was looking at. While my brother-in-law moved efficiently through the chaos, I was completely lost. But my ignorance wasn’t an obstacle to overcome quickly; it was a diagnostic tool that exposed where the industry had normalized dysfunction. Lessons learned:

• Measure the empathy gap. I spent nights in emergency rooms watching the same situations from both sides. Patients think: “I’m in the worst pain of my life, why is everyone just walking around?” Staff think: “He’s 47, he looks fit, he can wait, I need to complete this task first.” Both perspectives are rational, but the gap between them explains why the average ER has 2.3 stars on Google Reviews, worse than restaurants that give you food poisoning. Map these perception gaps across every customer touchpoint. The bigger the gap, the bigger the innovation opportunity.
  
  
• Ask the stupid questions that insiders ignore. When I first saw my physician brother-in-law writing medical notes on Thanksgiving, I asked why he was using Windows 98 software. He said his hospital had just paid millions for a “brand new” EHR system. That led to deeper questions: Why do medical notes read “cerebral infarction of the left hemisphere” instead of “your mom had a stroke”? Why can’t patients see their ER wait times when every pizza delivery app shows exactly where your order is? Industry veterans stop asking these questions because they’ve been trained that “it’s always been this way” or “regulations require it.” Most of the time, neither is true.
  
  
• Test with outsiders, not industry experts. Healthcare software companies routinely achieve 10-15 percent patient usage rates and consider that normal. We get 65-70 percent because we test with people who’ve never seen a medical interface before and who don’t know industry jargon. When someone’s grandmother can’t figure out how to view her lab results, that’s not a training problem—it’s a design flaw. Document every moment of confusion, every abandoned task, every place where users give up. Domain experts will rationalize these friction points; outsiders will expose them as unnecessary complexity.

Build Credibility Through Results, Not Credentials

I still don’t have the credibility in healthcare that I had in finance, despite eight years of work and millions of patients served. But I’ve learned to work around that limitation instead of fighting it.

• Partner with credible insiders from day one. At Vital, Dr. Schrager handles conversations where industry credibility matters; I handle everything else. This division of labor maximizes our strengths. Don’t wait until you hit credibility walls to find an insider partner; add an insider to your founding team or advisory structure early. The right insider can open doors that would take you years to crack, while you bring the outside perspective they need to see past industry limitations.
  
  
• Plan for 3x longer sales cycles than your previous industry. In healthcare, deals that would close in six months elsewhere take two to three years. Budget your runway accordingly and don’t mistake slow progress for no progress. Building that initial reference base takes time, but it becomes your most valuable sales asset.
  
  
• Lead with outcomes, not innovation. Insiders are skeptical of claims about breakthrough technology because they’ve been burned by vendors before. Instead of saying, “we’ve revolutionized patient engagement with AI-powered communications,” we say, “we helped Hospital X retain enough additional patients to generate $38 million in extra revenue and gain 2 percent market share in one year.” Bring documentation, third-party validation and reference customers willing to take calls. Make your track record do the selling.

Design for the Industry’s Psychological Reality

Every industry has its own psychological dynamics that outsiders initially miss. In finance, consumers make decisions daily but hate thinking about them. In healthcare, patients avoid thinking about their health until they’re forced to by a crisis.

• Find the core anxiety that drives all decisions. In healthcare, it’s not just fear of lawsuits, but fear of being responsible for bad outcomes. Design systems that make good outcomes feel inevitable rather than dependent on perfect execution.
  
  
• Design for actual engagement patterns, not ideal ones. We can’t replicate Mint’s weekly spending emails in healthcare, but we can engage people around family health (kids, aging parents) where motivation already exists.
  
  
• Build around existing workflows, not better workflows. Healthcare workers won’t adopt systems that require changing fundamental habits, no matter how much better those systems are.

Turn Your Outsider Status Into a Market Position

The moment I stopped trying to become a healthcare insider and started positioning Vital as bringing proven consumer technology approaches to healthcare, everything changed. We weren’t trying to be better healthcare software—we were bringing outside innovation to a broken industry.

This positioning works with the market because:

• It explains why you’re different without requiring deep industry knowledge to understand. “We approach patient engagement like successful financial apps” makes immediate sense to decision-makers.
  
  
• It leverages proof from your previous industry. Mint’s 25 million users became validation that our approach to boring, important information actually works at scale.
  
  
• It attracts customers who want innovation, not just improvement. Health systems dealing with 2.3-star patient satisfaction scores want breakthrough thinking, not incremental software improvements.

Protect Your Outsider Perspective

The biggest risk for successful outsiders is gaining too much acceptance and losing the perspective that makes you valuable.

After eight years in healthcare, I could probably get industry credibility if I focused on it. But when incumbent competitors copy our innovations, it forces us to think beyond traditional healthcare vendor approaches toward direct-to-consumer models that bypass industry gatekeepers entirely.

• Maintain bridges to your previous industry. The patterns that worked at Mint continue to inform Vital’s development. Don’t cut those ties completely—they’re your source of fresh thinking.
  
  
• Hire outsiders systematically, not just industry veterans. Balance domain expertise with fresh perspectives. Too much insider knowledge makes teams forget why outsider thinking is valuable.
  
  
• Use industry resistance as an innovation compass. The stronger the “that won’t work here” response, the bigger the opportunity might be.

The industries most desperate for outsider innovation are usually the ones most resistant to it. Your job as CEO isn’t to become an industry insider. It’s to stay enough of an outsider to see solutions that insiders can’t, while building enough insider credibility to implement them.