Dec 6, 2019 · 38m · 20vc
20VC: Why Raising A Mega-Round Makes Your Life Harder Not Easier, Why Your Board Is Not Your Boss and Lessons on Successful Board Management & The Biggest Breakpoints in Company Scaling with Emmanuel Schalit, Founder & CEO @ Dashlane
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gold bands on the timeline = statements, start to end. Hover to read, click to jump. CC turns on captions
On this episode of The 20 Minute VC, Harry Stebbings interviews Emmanuel Schalit, Founder and CEO of Dashlane, about the realities of mega-fundraising rounds, startup capital efficiency, effective board governance, and managing organizational scaling breakpoints.
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 27.8% of the talking time here. How this is scored →
Harry as informed peer 3.0 Guest teaching 4.9 Guest disagreement 1.9 Harry pushing back 1.6
speaking balance: gold is Harry, purple is the guest (3 minute bins)
Sharpest disagreement ▶ 19:47 Rejecting cash warehousing as a growth strategy
Emmanuel forcefully rejects the common founder belief that holding cash for long runway is safe, pointing out that without rapid growth it leaves company equity underwater.
Hardest push from Harry ▶ 19:25 Harry citing 12-year runway angel investmentHarry pushes back on aggressive capital deployment by bringing up his own angel investment that stockpiled 12 years of runway to weather market downturns.
Biggest teaching moment ▶ 23:16 Board governance masterclass: 'Your board is not your boss'Emmanuel educates the host and listeners on VC board dynamics, declaring that boards exist for advice and consent rather than operational management.
Harry holds his own ▶ 8:29 Harry framing mega-round macro environmentHarry demonstrates industry expertise by citing six $100M mega-rounds occurring on a single day to challenge the guest on capital excess.
the scores for every segment, with the reasoning behind each
| Chapter | Topic | Harry as informed peer | Guest teaching | Guest disagreement | Harry pushing back | Why |
|---|---|---|---|---|---|---|
| Emmanuel Schalit's Unconventional Path to Dashlane | 2 | 3 | 1 | 1 | Harry asks open conversational questions about Emmanuel's transition from running CBS Outdoor in France to joining Dashlane. Emmanuel shares a detailed personal story about a headhunter on a Eurostar train changing his mind about joining an early-stage startup. | |
| Why Raising Mega-Rounds Makes Life Harder, Not Easier | 3 | 6 | 3 | 2 | Harry introduces market context regarding recent $100M mega-rounds. Emmanuel reframes the founder narrative by arguing that mega-rounds raise exit hurdles and break middle management, culture, and internal infrastructure rather than making life easier. | |
| Navigating Internal Growth Pressure and Scaling Signals | 3 | 5 | 2 | 2 | Harry probes how pressure is managed within the team and when to switch from frugality to aggressive capital deployment. Emmanuel educates on pure software gross margin fundamentals compared to tech-enabled physical businesses like Uber or WeWork. | |
| Capital Efficiency and the Pitfalls of Warehousing Cash | 4 | 6 | 3 | 3 | Harry offers a counter-perspective from one of his angel portfolio companies holding 12 years of runway as a safety buffer. Emmanuel corrects this logic, explaining that holding idle capital without rapid growth risks putting equity permanently underwater due to inflated valuations. | |
| Effective Board Management and Working with VCs | 4 | 7 | 3 | 2 | Harry relays questions from existing VCs on investor helpfulness and governance. Emmanuel delivers a strong masterclass on VC governance, asserting that 'your board is not your boss' and outlining how to separate board advice from operational control. | |
| Quickfire Round: Books, Scaling Breakpoints, and Pitching | 3 | 5 | 1 | 1 | In a rapid-fire sequence, Harry prompts Emmanuel on reading, diversity, investor pitches, and organizational scaling points. Emmanuel provides structured breakdowns of organizational friction at 10, 50, 150, and 300 employees. | |
| Dashlane's Five-Year Vision and Interview Conclusion | 2 | 2 | 0 | 0 | The conversation concludes warmly as Harry asks for Dashlane's five-year outlook. Emmanuel outlines the goal to fix the user experience of web authentication and build a mainstream consumer brand. |
Statements from this episode (15)
Schalit: Macro excess capital driving venture funding will persist long term
“So the thing that is fueling that excess of capital Is not about to go away anytime soon, whether we find it good or bad.”
Schalit: Dashlane needs multi-billion dollar exit to justify $110M Sequoia round
“For us, you know, we need to build a multi-billion dollar company for this to make any sense, and when you look at the history of companies, not many people succeed doing that, so that's the first part.”
Schalit: Dashlane headcount projected to reach 450 employees within a year
“Now, suddenly you're talking about a company that's going to go from a year ago, we were eight people to today. We are 250 in a year. We'll be 450.”
Schalit: Pressure to raise Dashlane's mega-round came internally, not from board
“The pressure is not coming from the board and the investors. If you are A self-motivated executive. That pressure comes from inside. It's, you've just made the decision to take that round, and so as such, you have created that pressure for yourself. Nobody has…”
Schalit: Pure SaaS margins beat tech-enabled physical businesses on profitability
“When you think about some of the very large public or non-public companies like, you know, ride sharing and office space sharing, these are tech-enabled companies for which technology is somewhat important, but that structurally have very low gross margins bec…”
Schalit: Dashlane is adapting its culture to take higher risk
“And for us, it's a challenging shift because we've been frugal over the years, and now we have to relearn how we do things. We have to learn how to take a level of risk we're not used to taking. All the ingredients are there, the market, the leadership team, t…”
Stebbings: One angel portfolio company has 12 years of runway
“One of my angel investments has got 12 years of runway.”
Schalit: Warehousing cash without fast growth puts equity underwater
“If you're not growing at an incredible rate, if you are not guaranteed to be worth way more money without using that capital, then you must deploy it because otherwise you will have raised your exit bar. You will have a lot of money in the bank, but you will n…”
Schalit: A startup board is not the CEO's boss
“With VCs, because your board is not your boss. You are running the company and you're running the board and you have to really understand that because you become effective at working with your board and your VCs. The moment you understand that the board is the…”
Dashlane sends board decks 10 days early to focus meetings on strategy
“I'd say the second advice is to prepare the board materials a long time in advance. Send to, send them to your board members a long time in advance. We do that 10 days before our boards, and have individual discussions with each of them in advance of the meeti…”
Schalit: 150 employees is the breakpoint where implicit trust fails
“Obviously, you have that number or that 150 limit, which is really, really very palpable because it essentially means when you are in an organization where you can't know everyone enough to trust them implicitly, and this is where vision and culture become so …”
Schalit: Lack of diversity in tech is a hard-to-cure cancer
“Diversity. More women, more people of color. That is a cancer running through the tech ecosystem today, and it's one that's really hard to cure.”
Schalit: Sequoia's Jim Goetz convinced Dashlane to raise equity over debt
“You know, we had just raised a thirty million round of debt with no plan on taking equity, and in the meeting, Jim made me see the opportunity I was potentially missing by not considering an investment from Sequoia, and he convinced me in that meeting to rethi…”
Schalit: New York is the top US hub for European entrepreneurs
“But today, the New York ecosystem, thanks to, you know, some of the investors we're fortunate to have, Has become, for me, the best destination for European entrepreneurs that want to expand or start in the US for the reasons I just mentioned.”