Ramp and the Discipline of Obsession

It Starts With a Gap

Like most inflection points, it doesn’t begin with a grand plan.

It begins with noticing something broken.

A system everyone tolerates but no one questions.

An inefficiency hiding in plain sight.

Listen to Eric Glyman on The Biography Podcastand you’ll hear more than a how-to of scaling Ramp into a $22 billion juggernaut in under six years.

What comes through is obsession—an instinct for optimization, a habit of reading between industry lines, and a refusal to let frustration pass without turning it into leverage.

Vegas Lessons

Eric’s path isn’t a straight climb. It’s messy, shaped by early exposure to Las Vegas—the churn, the reinvention, the boom from half a million to two million people.

As a kid, he watched people build. Watched the city bend, expand, and reset. He learned that real building meant living with uncertainty. Rolling with change. Accepting chaos, sometimes, as catalyst.

His first job at Express—selling fast fashion for $8.50 an hour—sounds trivial. It isn’t. It’s a seed in the Ramp story.

There, he noticed something deeper than discounts: the misalignment between price, value, and perception. Every shopper left thinking they’d won. Few realized how elastic the system really was. Eric logged the insight quietly: every system is designed for someone’s benefit. The work of an entrepreneur is to see who.

Harvard in a Crisis

At Harvard during the financial crash, Eric sat among peers chasing default paths—banking, consulting, grad school. The safe routes.

A Brazilian friend, Thomas, and a chance meeting with Kareem, his future co-founder, pulled him elsewhere. Together, they hinted at a truth: stepping off the default track—out of curiosity or necessity—forces learning. Creates constraint. Sparks invention.

Exposure abroad—China’s rise, the World Fair, learning languages—left him restless. He wanted lessons not in textbooks, but in lived detours. In side bets. In deviations.

Frustration as Genesis

The real professional insight didn’t arrive as a clean epiphany.

It came as irritation.

Paribus, his first company with Kareem, was born from losing $100 to dynamic pricing. Airline fares dropping. Retail prices shifting.

The pain was personal. The question was simple: if it annoys me, who else feels this? Could it be automated?

Paul Graham calls it “noticing.”

Not brainstorming a big idea. Not chasing a hot market.

But watching the grain of reality closely, and carving along it.

The Paribus Grind

The Paribus years hardened Eric’s edge.

Rejected by Y Combinator. Question marks around product-market fit. Legal ambiguity in scanning receipts.

Instead of fixating on outcomes, Eric focused on inputs. Breaking funnels apart. Obsessing over what could be controlled. Running feedback loops fast.

Marketing didn’t come from whiteboards, but from listening to how users described value: it saves you money on things you already bought online.

Friction was hunted down—onboarding, trust points, payoff moments.

A tweak in referral framing—avoid paying 5%versus gain 5%—drove growth tenfold. Psychology mattered as much as math.

Golden Handcuffs

After the acquisition, Eric tasted banking and restructuring. The money was good. The identity was not.

He saw how “golden handcuffs” work—how easy it is to drift into a life you never designed.

Starting Ramp wasn’t just opportunity. It was self-respect. A refusal to drift.

Every rejection—jobs, YC, status—became fuel, not friction.

Ramp’s Spark

Ramp began with the same posture as Paribus: a slow day at work, an eye for inefficiency.

Not a SaaS clone. Not a hot trend.

Eric had seen firsthand: most business spending isn’t just sloppy. It’s unintelligent.

The real tax isn’t missed refunds or subscription creep. It’s time. Hours lost to expense reports. To approvals. To manual finance.

Ramp’s thesis was clear:

Automate the mundane.

Align incentives.

Root out waste.

Give teams back their attention.

The culture locked in from day one: maximize customer value, reflect hard, build in public. Share playbooks. Share mistakes. Ship fast enough to make even a Superbowl ad in a week.

The Repeatable Legacies

Eric’s style, and Ramp’s story, distill into five legacies worth carrying:

1. Obsession With Inputs, Not Just Outputs

Charts matter, but behaviors matter more. Eric’s teams pulled levers weekly, asking which latch points controlled conversion, loops, or churn. Downturns weren’t panic—they were prompts to re-examine growth mechanics.

2. Decomposition and Feedback Loops

Every piece of Ramp—onboarding, viral triggers, delight moments—was decomposed and stress-tested. A referral tweak proved how small framing shifts could bend growth disproportionately. The company behaved less like a fortress, more like a living system. Probe, adjust, repeat.

3. Building Trust as Architecture

Trust wasn’t a feature. It was foundation. From design to messaging, every touchpoint was engineered to reduce friction, tell the truth, and earn confidence. In a culture of “move fast and break things,” Ramp found advantage in doing the opposite: move fast, but build what you’d want yourself.

4. Grit in Downturns

Cease-and-desists. 80% drops in revenue. Each one echoed the same mantra: keep going, keep solving. The founder’s job isn’t a perfect run. It’s survival through indifference, volatility, and chaos—by turning every setback into iteration.

5. Relentless Customer Evangelism

Ramp’s viral sparks—Today Show crashes, bold referral schemes—weren’t marketing tricks. They came from thinking like a hurried user, not a dashboard-driven marketer. Product-led growth at its rawest: find the moments of truth, then let users carry the message.

The Parable

Tomorrow, when you sit down to build, Eric’s story reads less like biography and more like blueprint.

Start from pain you’ve lived.

Iterate at the speed of curiosity.

Stay close to first principles.

Optimize the few things that compound.

And when the world throws friction at you, meet it by solving harder, trusting your loops, and stacking small disciplines into outlier outcomes.

Because billion-dollar companies rarely come from chasing trends. They come from obsessing over basics. Shipping fast. Surviving chaos.

And above all, from giving back hours—first to yourself, then to your customers, and finally, if you’re lucky, to civilization itself.