Jun 2, 2021 · 40m · 20vc
20VC: Ramp's Eric Glyman on Why You Should Never Take The Highest Price, Working With Venture Funds vs Crossover Funds and How To Determine What To Buy vs Build as a Founder Today?
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gold bands on the timeline = statements, start to end. Hover to read, click to jump. CC turns on captions
In this episode of 20VC, host Harry Stebbings chats with Eric Glyman, co-founder and CEO of Ramp, about the strategy, fundraising principles, and operational cadence behind Ramp's rapid growth. Glyman shares critical insights on why founders shouldn't optimize for peak valuations, how to balance building versus borrowing technology, and how to maintain high decision velocity while scaling.
How this conversation actually went
Every chapter scored 0–10 on four independent dynamics. Hover any point for the reasoning behind the score. Harry holds 26% of the talking time here. How this is scored →
Harry as informed peer 2.3 Guest teaching 3.3 Guest disagreement 1.0 Harry pushing back 2.2
speaking balance: gold is Harry, purple is the guest (3 minute bins)
Sharpest disagreement ▶ 29:44 Rejecting Crossover Signaling Risk
Eric directly reframes Harry's premise about crossover fund signaling, explaining that low ownership targets prevent dominant equity positions and eliminate traditional signaling risks.
Hardest push from Harry ▶ 20:56 Challenging Loss of Creative ConstraintsHarry forcefully challenges Eric on whether raising over $300 million lifts necessary constraints and undermines the disciplined science-experiment mindset of earlier rounds.
Biggest teaching moment ▶ 23:16 Masterclass on Refusing the Highest ValuationEric educates Harry on total enterprise value optimization, detailing how taking a lower price reduces 409A exercise costs for employees and turns investors into enthusiastic promoters.
Harry holds his own ▶ 17:00 Calling Out Core Business Model TensionHarry demonstrates domain expertise by challenging Eric on the structural conflict between earning interchange fees on spend volume while advising clients to spend less.
the scores for every segment, with the reasoning behind each
| Chapter | Topic | Harry as informed peer | Guest teaching | Guest disagreement | Harry pushing back | Why |
|---|---|---|---|---|---|---|
| Sponsorship Announcements | 0 | 0 | 0 | 0 | Host monologue introducing the guest and reading sponsor advertisements with no guest involvement. | |
| The Power of a Unified Core Narrative | 2 | 3 | 1 | 2 | Harry asks open questions about Paribus and handling stress, playfully teasing that Eric sold his first startup too early. Eric details how fixing a core narrative early accelerates company velocity and how living in China taught him emotional stoicism. | |
| Co-Founder Dynamics and High-Velocity Decision-Making | 1 | 3 | 0 | 1 | Harry asks about decision-making framework updates. Eric elaborates on his complementary dynamic with co-founder Kareem Atiyah and how accountability to others drives high-velocity execution. | |
| Operational Cadence, Speed, and Compounding Growth | 2 | 4 | 1 | 2 | Harry references Ramp's board deck metric of tracking company age in days and asks how to balance speed versus precision. Eric explains that core financial infrastructure requires months of exact execution, while growth tactics demand rapid iterative testing. | |
| Deciding What to Build vs. Borrow | 3 | 3 | 0 | 1 | Harry probes the build versus borrow decision matrix, linking Ramp's architecture back to Paribus's pain points. Eric outlines using Marquetta's API to launch within 45 days while keeping expense data models proprietary. | |
| Business Model Alignment in Spend Management | 3 | 5 | 2 | 4 | Harry challenges Eric on the tension between generating revenue via interchange volume and trying to reduce customer spend. Eric invokes the Innovator's Dilemma to explain why legacy incumbents like Amex are structurally unable to align with customers this way. | |
| Framing Fundraising Rounds as Science Experiments | 3 | 3 | 1 | 4 | Harry pushes Eric on whether raising hundreds of millions lifts the creative constraints that drove earlier lean execution. Eric responds by explaining how operational burn discipline and system training preserve focus despite capital abundance. | |
| Capital Allocation and Strategic Burn Management | 3 | 5 | 1 | 2 | Harry asks about valuation dynamics and Eric's ethos of never accepting the highest price. Eric delivers a detailed breakdown showing how leaving upside on the table lowers employee 409A stock costs and builds long-term investor advocacy. | |
| Venture Funds vs. Crossover Funds | 3 | 4 | 1 | 3 | Harry asks if investors genuinely add value and contrasts crossover funds with early-stage venture firms. Eric contrasts Keith Raboy's focus on product compounding with Coatue and D1's focus on public-market scale and unit economics. | |
| Ownership Targets and Signaling Dynamics in Growth Capital | 4 | 5 | 3 | 4 | Harry pushes hard on whether crossover funds participating in B and C rounds create negative signaling if they skip later rounds. Eric reframes the premise by pointing out crossover funds take smaller 2-5% ownership targets, which eliminates traditional VC signaling traps. | |
| Leadership Scaling Challenges and Operator Mentors | 2 | 3 | 0 | 2 | Harry prompts Eric on personal scaling pain points and operator mentors. Eric discusses the rapid evolution required of a CEO every three months as team headcount doubles and cites coach John Wooden's principles. | |
| Quickfire Round | 2 | 2 | 2 | 1 | Harry conducts a quickfire segment covering venture industry gossip, favorite board members, and competitive strategy. Eric warns against competitive arrogance and defends the strength of the New York tech ecosystem. |
Statements from this episode (29)
Ramp has raised over $390 million in funding
“To date, Eric has raised over three hundred and ninety million dollars for the company from some of the best, including Thrive, Stripe, Founders Fund, Code Two, and Box Group, to name a few.”
Glyman: Online shoppers leave billions on table from price drops
“Consumers were leaving billions of dollars on the table, literally, whenever prices would drop, like, a day, two days, a week after they bought items online.”
Glyman: Defining a startup's core narrative early enables faster operational execution
“And so by fixing early in the life of a company, really what's the bigger story? What are you about? It allows you to move much faster on the other questions. So we can get into that, but I think actually fixing the core of the company early is really key.”
Glyman: Paribus lost 80% of its revenue overnight in a single month
“There was one month when 80% of our revenue disappeared basically overnight.”
Glyman: High leadership stress directly causes a startup's worst decisions
“Whenever we really were truly stressed, that was when a lot of the worst decisions were made.”
Glyman: Ramp spent its first 120 days building core infrastructure
“We didn't ship anything to customers, I think, in the first 120 days in the life of the company, and we were building the core ledger, and we were building the core financial infrastructure, and a lot of the core accounting integrations, all that”
Glyman: Teams should be judged by the slope of their progress
“I do very deeply believe that that speed is everything. Like, what is the shape of slope in terms of what you're doing always is like how you should judge teams. And their output.”
Glyman: The API revolution was hype five years ago, but is now real
“Five, six years ago, there was this early talk of this API revolution. You could tap into different APIs and building services, and it was talked about a lot then. I don't think it was really true, but now it is.”
Glyman: Ramp launched with Visa in 55 days using Marqeta
“Within 45 days, we were able to be live with our partner bank, within 55 with Visa, within 65 internally, we were able to go and start Doing internal transactions.”
Glyman: Ramp aims to build Waze for business expenses and Shopify for CFOs
“I think that a lot of really the North star of where we're headed as a business is, can you actually go understand what things cost and build, let's say like a ways for all sorts of business expenses, a Shopify suite for the CFO.”
Glyman: Credit card issuers are misaligned with business customer profitability
“I think the problem in the credit card industry is that the issuers are so misaligned. They're often trying to like outsmart their customers, tell them we'll give you eight X points on this five X points on this incentivize your customers to spend more and eff…”
Glyman: Amex cannot launch spend-reduction tools due to Innovator's Dilemma
“So first, there's this question of, like, why isn't Amex doing this? Like, why isn't Amex going saying, let's go apply, like, a savings algorithm? And for them, it's a really, like, this is true, like, Clay Christensen, innovator's dilemma. It's like, yes, you…”
Glyman: Ramp's burn rate is nearly unchanged, giving a 10-year runway
“So right now, our burn rate is not far from what it was, like even, like a year ago. And so there's an element of, we now just have a lot more time before the expiration, call it like a decade, you know, versus like, we can run out of stuff in two years.”
Glyman: Ramp spent $50K on marketing while processing $1B annually
“I think we spent Like 50,000 dollars on marketing last month, but are doing like a billion dollars in transactions a year.”
Glyman: Founders should optimize for total enterprise value, not single-round price
“It's not on the single round price. It's on total enterprise value.”
Glyman: Leaving valuation on the table creates enthusiastic investor advocates
“If you leave value on the table, you start to have really happy investors who go to bat, tell their people about this. They tell other companies about it because they're excited and feel like it can go up even more from there.”
Glyman: Lower fundraising valuations make employee equity more affordable and valuable
“By raising at a lower price, you actually make your stock more a Affordable for your employees, and they can enjoy more upside”
Glyman: Venture investors add real value in B2B, unlike other sectors
“In some categories, I would say absolutely not. I think that in B to B, I really think that they can.”
Glyman: B2B founders can drive customer sales using cap table strategy
“And if you've got great people around the table, actually, and you structure it well, you can actually build Part of your book of business through your cap table strategy.”
Glyman: Crossover funds filled a critical financing gap for capital-intensive startups
“Crossover funds were this really interesting, compelling answer that didn't quite exist years ago.”
Glyman: D1 Capital prioritizes unit economics over early product and team
“I think with D one, a lot of this is like, how do you build a great business? So forget a great product and a great team, but flash forward a few years, how do you think about the financial innards that will actually make the unit economics The performance. Gr…”
Glyman: Strong performance renders investor signaling risks largely irrelevant
“If you've got great performance and things are working, no one can really hurt you, and I think that if things are really not working, no one can Really, truly help you all that much.”
Glyman: Crossover funds do not enforce strict venture ownership targets
“One of the under talked about attributes of crossover funds in particular is they don't have these, they're like throw out ownership targets. That's not nearly as important as call it Valley venture funds, make them out to be, and they could be perfectly fine …”
Glyman: Ramp shares full board meeting decks with all 100 employees
“We actually go Back to the company. All a hundred people at ramp can see what was in the board meeting and his chance to actually distill down the strategy itself.”
Glyman: Effective leadership habits become liabilities as startups double every three months
“What made you good two months ago probably would be holding you back, and if you really are growing at a compounding rate, and suddenly three months later, your company is twice the size, and three months after that, or you're four X the size, and then eight X…”
Glyman: Venture capital is overly gossipy rather than future-focused
“It's so gossipy. For all this talk about being focused on the future, I feel like half the industry is wondering what are the other people working on or thinking about at this very moment.”
Glyman: Founders must assume competitors are at their best because arrogance spreads fast
“I think internally, you have to think about them and view them at their best. Arrogance is super contagious. You know, if people see, like, the founders or other people at the team are like, oh, the Competition is fine, or they don't understand this or that. I…”
Glyman: CFO software and spend management will yield multiple $100B+ companies
“And look, I think that there are many hundred billion dollar plus companies in this space. I know Amex It's had since 1850 to work on it, and there are a number of others, but I think that if you can truly do that, and if you can create differentiated value in…”