September 13, 2025
Jeff Schumann spent years as a CIA contractor hunting terrorists in the dark web before joining a corporate job he hated. That frustration sparked a weekend project with three engineer co-founders that became Aware, a cybersecurity platform protecting enterprise communications. Starting with zero fundraising experience, they bootstrapped to $1.2 million ARR through a brutal first sale in India, strategic pricing lessons, and relentless customer focus before raising over $100 million from Goldman Sachs and eventually exiting to a $10 billion company.
Follow Jeff: LinkedIn
Jeff Schumann's first customer came from the most unlikely place: a cold email to 55,000 Microsoft users yielded 8 clicks, 2 demos, and 1 customer in India. That $150,000 deal took a full year to close, involving international business law, tax treaties, and brutal price negotiations down to 10 cents per user.
The customer kept walking them down in price because they had no benchmarks for what their cybersecurity software was worth. But two months after closing that deal, something magical happened: the customer introduced them to another company down the street, and that second deal closed in under three months for $350,000.
"We didn't know what to charge for the software. I entered into a brutal back and forth with the buyer. They kept walking us down in price all the way to the point where we were talking about each user being worth cents, like 10 cents per user. We didn't know if that was the value of our software because they were the first conversation."
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After struggling with that first pricing negotiation, Jeff called Travis Vander, former head of sales at Yammer (which sold for $1.2 billion to Microsoft). Travis gave him advice that seemed insane: charge 10 times more than your last deal as your starting point.
For their second customer, instead of starting negotiations around $150K, they opened at $1.5 million and worked down. The result? They closed at $350K for the same number of users, more than doubling their per-user value simply by anchoring higher.
"He was like, no, just for your next one, just charge 10 times more at the first conversation. If you ended the last deal for a company at 150K, start this next one at $1.5 million and then work down from there. And it was amazing because it worked arguably three times better than the prior deal."
When their first VC asked which of the four co-founders was CEO, they all spontaneously pointed to Jeff without any prior discussion. This coffee shop moment became the foundation of their seven-year partnership because it revealed their natural dynamics and mutual trust.
Jeff had been using "VP of Sales" as his title when selling to appear more established, but instantly became CEO for investor conversations. The seamless transition happened because the co-founders organically recognized his communication skills and customer-facing abilities, even though he was an engineer by training.
"A VC asked us at the coffee shop, there's four of us, he's like which one of you is the CEO and they're like oh he is. That's how that played out. We never had the chat but they all were like Jeff's the CEO and suddenly I became the CEO."
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The Challenge: Building a company while maintaining financial stability and testing market demand.
Jeff's Solution: All four co-founders kept full-time jobs while building Aware on weekends at coffee shops. They treated their W-2 salaries as "the best non-dilutive investor ever" providing steady income, benefits, and flexibility to build without pressure.
How to Apply: Use your current job as your bootstrap funding. Dedicate specific times (weekends, evenings) to building your MVP. Don't quit until you have paying customers and clear market demand.
The Challenge: Not knowing how to price your product in early sales conversations.
Jeff's Solution: After learning from pricing mistakes, start every new deal at 10X your last closed deal, then negotiate down. This sets a much higher anchor point and typically results in 2-3X higher final prices.
How to Apply: Research what customers in adjacent markets pay for similar solutions. Start high and justify value rather than starting low and trying to increase. Your software's value is "in the eye of the beholder."
Unlock 2 More Proven Frameworks + Full Webinar Video
Jeff Schumann shared four battle-tested frameworks from bootstrapping to $1.2M ARR and raising $100M. Get immediate access to the remaining frameworks:
✅ The Four-Founder Balance System
✅ The Customer-Driven Roadmap Strategy
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