May 9, 2025 · 1h 9m · 20vc
20VC: Four Traits of the Most Successful Founders | How to Hunt and Close Talent Like a Pro and Where All Founders Go Wrong | Lessons Raising $397M From the Best Investors in the World with Eléonore Crespo @ Pigment
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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: The Memo, host Harry Stebbings interviews Eléonore Crespo, co-founder and CEO of Pigment, to explore her journey from VC investor to building a high-growth enterprise software company. Crespo shares actionable insights on co-leadership mechanics, executive talent scouting, managing board relationships, US expansion, and maintaining a long-term $100 billion vision.
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 29.5% of the talking time here. How this is scored →
Harry as informed peer 4.7 Guest teaching 4.9 Guest disagreement 3.1 Harry pushing back 3.7
speaking balance: gold is Harry, purple is the guest (3 minute bins)
Sharpest disagreement ▶ 36:05 Rejection of Dilution Optimization
Eleonore forcefully rejects Harry's premise that raising excess capital buffers is bad due to dilution, stating she could not care less about personal financial outcomes compared to building a massive company.
Hardest push from Harry ▶ 16:43 Revolut Counterexample ChallengeHarry directly refuses Yuri Milner's founder framework, using Nick Storonsky and Revolut as explicit counterevidence against the necessity of psychology and storytelling in founder success.
Biggest teaching moment ▶ 52:15 Parenthood and Happiness ReframingEleonore calls Harry nuts for fearing parenthood will degrade his work performance, re-centering the conversation around fundamental human happiness versus pure output metrics.
Harry holds his own ▶ 17:05 Insider Knowledge on Revolut HiringHarry demonstrates deep insider domain knowledge regarding Revolut's early talent acquisition strategy, noting that Storonsky hires and trains young talent rather than recruiting traditional executives.
the scores for every segment, with the reasoning behind each
| Chapter | Topic | Harry as informed peer | Guest teaching | Guest disagreement | Harry pushing back | Why |
|---|---|---|---|---|---|---|
| The Bed-Rest Catalyst: Founding Pigment and Transitioning from VC | 5 | 6 | 4 | 5 | Harry asks a sharp question about why Index Ventures isn't on Pigment's cap table and challenges Eleonore on whether board members should push founders. Eleonore explicitly tells Harry he is wrong, reframing investor challenge as exposing overlooked blind spots rather than just pushing for bigger scale. | |
| Co-Founder Sourcing and Masterclass on the Co-CEO Model | 4 | 5 | 3 | 4 | Harry challenges the wisdom of co-CEO structures and 20-year co-founder commitments. Eleonore counters traditional VC consensus, explaining that co-CEOs provide a superpower by doubling customer-facing bandwidth and serving as a built-in truth mechanism. | |
| The Four Core Traits of Generational Founders | 7 | 4 | 4 | 7 | Harry aggressively challenges Yuri Milner's core founder traits, using Revolut and Nick Storonsky as a direct counterexample to the necessity of storytelling or psychology. Eleonore defends the framework by reframing storytelling to include investor pitch mechanics and public marketing team execution. | |
| Hunting and Closing World-Class Executive Talent | 5 | 4 | 1 | 2 | Harry shares his own candidate sourcing tactics while asking Eleonore how she identifies and closes top talent. Eleonore delivers a structured overview on tracking trigger events like PE buyouts and constructing tailored interview rubrics. | |
| Compensation, Cultural Alignment, and Removing Bureaucratic Friction | 4 | 3 | 1 | 2 | Harry and Eleonore discuss compensation, title inflation, and organizational scaling. Eleonore highlights her strategy of presenting potential hires with a pitch deck detailing company flaws and upcoming challenges to filter out ego-driven candidates. | |
| Board Selection, Dilution Mindset, and Managing Through Crisis | 6 | 6 | 5 | 5 | Harry challenges Pigment's preemptive fundraising strategy as dilution-inefficient. Eleonore dismisses optimization for equity dilution, emphasizing long-term business building and performing deep CIA-style due diligence on prospective board members. | |
| Winning the US Market and the 2 AM Olympic Deal | 4 | 5 | 3 | 3 | Harry notes that entering the US market in year one contradicts standard VC advice to establish local European dominance first. Eleonore explains why US CFOs move faster and shares a story of closing a seven-figure deal during a 2 AM call at the Olympics. | |
| Perspective on Parenthood, Optimism, and Bringing 'Play' to Leadership | 3 | 7 | 4 | 3 | Harry expresses concern that parenthood might reduce his competitive edge, prompting Eleonore to call him nuts. She educates him on integrating play, maintaining personal balance, and finding true joy outside of work metrics. | |
| Quickfire Round: AI Strategy, Ideal Board Members, and a $100B Vision | 4 | 4 | 3 | 2 | In a rapid-fire exchange, Harry asks about market size ceilings and AI disruptions. Eleonore playfully rejects a $10B outcome ceiling, asserting a $200B to trillion-dollar multi-act vision for Pigment. |
Statements from this episode (25)
Crespo: Pigment is being built to scale over 30 years
“I'm here to build a big company, a massive business. I want to build a company that scales for the next 30 years, and I want the best people around the table.”
Crespo: Startup board members hold more power than CEOs realize
“The power of the board is bigger than you think. If the board wants to fire you one day, probably they can.”
Crespo: Pigment excluded Index Ventures to bring fresh perspectives
“All of the people at Index are my friends and they were already helping me. And in a way, I already knew the way they were thinking. And so for me, it was really important to bring new people, fresh ideas to the table.”
Crespo: Pigment refuses to hire friends to ensure novel perspectives
“I'm not hiring my friends at Pigment. I'm hiring people that I don't know about that can bring things that I don't know.”
Crespo: Co-CEO Model Lets Companies Spend Double Time With Customers
“Well, when you are co-CEO, you actually have that superpower of being able to spend twice as much time with your customer, listening to them.”
Crespo Advises Founders to Spend Time Working in Venture Capital
“It's something I would advise to any founder, pretty much being a VC, because it created so many things.”
Crespo: U.S. Tech Dominance Driven by Superior Storytelling and Marketing
“The reality is that you can see the power of many U.S. Companies out there is a power of marketing, how much they have understood the importance of marketing and storytelling, and that's what I'm learned, like, that's what I've learned at INDEX, the importance…”
Crespo: Revolut Has One of the World's Best Marketing Teams
“And the stories to the public are not necessarily coming from Nick, but again, he has one of the best marketing team in the world, full stop.”
Crespo: Pigment recruited top talent directly from Paris Olympic Games CFO
“I lose a deal against another company, I always ask the name of the rep. I do something, you know, where I hear that there is, giving you a recent example, we had the Olympic Games in Paris last year, and I met the other day the CFO of the Olympic Games, the o…”
Crespo: Interview 20 top executives to learn to hire for unknown roles
“For me, the biggest advice is go human to human. Ask, when you're hiring your CRO, ask the 20 best CROs out there. Best CROs, again, in your category. What have they done so great? What makes them so different? That's really my number one advice to anyone.”
Crespo: European Employees Understand Equity Less Well Than US Peers
“I think we could be more appreciative of equity. Employees, a lot of employees do not understand equity as well as US employees.”
Crespo Shows Candidates a 'Hardships Deck' Before Hiring Them
“Now I do something that I didn't know in the past is putting in front of my candidates a deck to show them what's going to be hard at Pigment and make it very clear to them. Saying you're going to work harder than ever in your life here. These are the impossib…”
Crespo: 60% of Pigment's business and half its team are in the US
“Half of the team today of Pigment is in the US. Most of our business, 60% of our business is in the US. Our largest customers are all in the US.”
Crespo: Pigment will never prioritize term sheet terms over board quality
“I will never, you know, take the best term sheet based on, on whatever is written in there, because you just want the best people on your board.”
Crespo: Startups get individual board members, not VC fund brands
“And at your board, you get one person. You don't get a brand.”
Pigment targeted US enterprise buyers during its first year of sales
“First, we went very early to find customers in the US. First year of selling, pretty much we went to the US.”
Crespo: Incumbent FP&A software competitors lost their innovation velocity
“It's a world where a lot of companies out there are private equity owned. And so unfortunately not innovating at the pace at which they used to innovate. And most of our competitors are, you know, 20 years old plus, 15 years old plus, and have lost this speed …”
Crespo: Winning US enterprise software buyers is easier than in Europe
“A lot of people say it's harder than you think, where I think it's actually easier than you think. Because I said it's hard, yes, but it's easier than in Europe. People buy faster.”
Pigment closed a major US tech CEO deal in under 15 days
“Literally this deal was done in not even 15 days. He called me, it's two AM.”
Stebbings: Building a $10B company requires prioritizing work over relationships
“I always start, like, dating someone, I'm like, listen, number one is my company. Always. Always. That is always how it's gonna be. And I think you have to if you're gonna build a ten billion dollar business.”
Crespo: Her husband knows nothing about Pigment as they never discuss work
“I'm going to tell you something, maybe you won't believe me, but it's true, he doesn't know anything about Pigment. We never talk about work together.”
Crespo: Thin AI wrappers will die; deep workflow SaaS will win
“If you are building a layer, like a marketing tool that is just a layer, probably you can be killed by AI. If you're building something more fundamental that, you know, requires like, for instance, at Pigment, you know, we have this huge database, huge compute…”
Crespo: Pigment aims for $1T, but current platform won't get them there
“Nothing is preventing me from thinking how can I create a trillion dollar company out there? So what I am constantly thinking about, and this is where you need to think slow, is what is the second, the third, the fourth act of pigment? Because the platform we …”