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
🎯 Summary
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
This episode features Harry Stebbings (20VC) in conversation with Eléonore Crespo, Co-founder and CEO of Pigment, a rapidly scaling European business planning platform that has raised over $397M from top-tier investors. The discussion centers on Eléonore’s journey from VC (Index Ventures) to founder, the critical traits of successful founders, the unique dynamics of her co-CEO structure, and her rigorous, proactive approach to talent acquisition.
1. Focus Area
The discussion is firmly rooted in General Tech/SaaS Entrepreneurship and Scaling. Key themes include founder psychology, strategic hiring, board dynamics, the transition from investing to founding, and building a generational company.
2. Key Technical Insights
- Co-CEO Superpower for Customer Focus: The co-CEO structure (Eléonore focusing on the business/GTM, Roma on product/engineering) allows the leadership team to dedicate twice the time to customer interaction, which Eléonore views as the ultimate competitive advantage for building a customer-first product.
- Valuing Experienced Operators: Eléonore strongly advocates for hiring executives who have “seen the movie”—specifically, those who have scaled a company from the current ARR stage to multiple billions, as they bring invaluable learned lessons to avoid common pitfalls.
- The “Never Settle” Mindset: The most crucial trait in experienced hires (like her co-founder Roma) is an ingrained curiosity and a commitment to never settling, ensuring continuous adaptation even after achieving success.
3. Market/Investment Angle
- Board Power Dynamics: Eléonore emphasizes that founders must respect the power of the board, noting that the board ultimately has the authority to remove the CEO, underscoring the need for strong alignment.
- VC as Founder Training: Her experience at Index Ventures is framed as the “best college of life” for a founder, providing unparalleled insight into what “amazing” looks like in execution and scale.
- Investor Alignment: Eléonore intentionally sought investors who would challenge her, valuing those who push leaders to think harder rather than simply agreeing with the status quo.
4. Notable Companies/People
- Pigment: The focus company, a rapidly growing business planning platform.
- Roma (Co-founder/Co-CEO): Highlighted for his complementary technical leadership, humility despite prior success (Criteo IPO), and ability to challenge Eléonore constructively.
- Index Ventures: Eléonore’s former firm, cited as crucial for learning operational excellence.
- Top Founders Traits (as learned from VCs): Psychology/Human Understanding, Incredible Storytelling (especially for investors/public), Having a Truth-Telling Partner, and Relentlessness/Ambition.
5. Regulatory/Policy Discussion
None explicitly discussed. The focus remained strictly on business building, talent, and fundraising strategy.
6. Future Implications
The conversation suggests that in the current market, storytelling and human psychology are as critical to success as product excellence, especially for attracting top talent and securing investment. Furthermore, the success of the co-CEO model implies that rigid, traditional governance structures may be suboptimal for companies prioritizing deep customer immersion.
7. Target Audience
This episode is highly valuable for Founders (especially early to mid-stage SaaS CEOs), Executive Recruiters, and Venture Capital Professionals interested in operational excellence, talent strategy, and founder psychology.
Comprehensive Summary
Eléonore Crespo’s discussion with Harry Stebbings provides a deep dive into the strategic mindset required to build a “generational defining business,” drawing heavily on her transition from a successful investor at Index Ventures to the CEO of Pigment.
The narrative arc begins with the unlikely origin of Pigment: Eléonore’s year-long recovery from back surgery, which provided the necessary space to crystallize her ambition to found a company and meticulously select her co-founder, Roma. She stresses that co-founder selection is a multi-year sourcing exercise, prioritizing complementary skills, shared values, and the ability to maintain a strong partnership for 20+ years. Key traits she sought included humility (even after prior success like Criteo’s IPO) and a commitment to continuous self-improvement.
A major point of contention with conventional wisdom is Pigment’s co-CEO structure. Eléonore argues this works because it allows both leaders to dedicate maximum time to their respective domains—Roma to product vision and Eléonore to business building and, crucially, customer obsession. This dual focus grants them a “superpower” in gathering customer insights that single CEOs often lack due to time constraints.
Eléonore outlines a rigorous, four-part framework for identifying the Four Traits of the Most Successful Founders, derived from her time observing top performers at Index: 1) Mastery of Psychology (understanding people), 2) Exceptional Storytelling (essential for investors and marketing), 3) Having a Truth-Telling Partner (someone unafraid to challenge), and 4) Relentlessness/Ambition.
The most detailed section covers Talent Acquisition, which Eléonore calls the number one job. Her process is proactive and continuous:
- Constant Sourcing: Actively scouting talent everywhere (e.g., asking competitors who the best rep on
🏢 Companies Mentioned
💬 Key Insights
"I receive an email. And it's probably about 1:00 AM from one of the biggest tech CEOs in the Valley... Is that can I call you now? I'm like, sure. And he calls me, and it's 2:00 AM. He says, I don't know, I want to do the biggest rep and replace of one of your competitors right now, and I want you to start tomorrow. And by you right now, I don't care, like let's go. And literally, this idea was done in not even 15 days."
"A lot of people say it's harder than you think, where I think it's actually easier than you think [winning in the US]. Because they say it's hard, yes, but it's easier than Europe. People buy faster. People buy and are very brave to have the courage to actually go in front of the leadership team and say, in order to be successful, I need the best technology."
"Yes, I would say not only marketing, but innovation more importantly. What is that? Innovation are indeed investing engineers, invest in spending more time when it's crazy, smooth building the best of the best product, when it's the end of the crisis, you go out and you just kill the market."
"What, what you see is that the most experienced investors have seen that movie before, and they know that maybe the market is shaking now, but in three years, it's going to get better again. And so, for instance, I have Rob Waite around the table, and Rob has seen the movies so many times, and Rob is arresting me when there is a crisis. It's time to invest. Let's go. Let's go because your competitors cannot invest right now."
"CIA due diligence on the person, as many back channels as you can, is spending as much time as you can understanding what is wrong about that person, deep diving into what is wrong, what is wrong..."
"People think about the brand before thinking about the person, and at your board you get one person, you don't get a brand."