What Founders Get Wrong About Scaling – With Carta’s CEO

a16z Podcast

a16z

Science, Innovation, Business, Entrepreneurship, Culture, Disruption, Software Eating The World, Technology

4.4 • 1.1K Ratings

🗓️ 7 March 2025

⏱️ 41 minutes

🔗️ Recording | iTunes | RSS

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Summary

Henry Ward, cofounder and CEO of Carta, has spent over a decade scaling his company from an early-stage startup to a 2,000-person industry leader. In this Speedrun conversation with a16z Games partner Josh Lu, Henry shares hard-earned lessons on: -Hiring missionaries vs. mercenaries — and how to keep company culture intact as you scale -The reality of product-market fit and why many founders try to sell too soon -The evolution of a CEO — from building a product to building a system around you -Inputs vs. outputs, and why companies should focus on the right leading indicators -Transparency in leadership, including when (and when not) to share This episode is packed with candid insights and lessons on company building. Recorded live at the a16z Speedrun program, you can learn more at a16z.com/games/speedrun.

Transcript

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0:00.0	I remember my first pitch and it was so bad they walked me out the back door.
0:06.0	By design, transparent to a fault.
0:08.0	So as transparent as I can be until something bad happens.
0:12.0	The biggest difference is it's the first time in your career you work for somebody that knows less than you do about what you do.
0:18.0	That was Henry Ward, co-founder and CEO of Carter, a company that started reinventing
0:23.8	the cap table way back in 2012.
0:27.1	Since then, the company's grown to about 2,000 people and is trusted by over 40,000 companies.
0:33.2	13 years in, it's safe to say that Henry has just about seen it all, and he is not shy about his learnings.
0:39.3	So in today's wide-ranging conversation with A16C games partner, Josh Liu, they discuss when to hire missionaries versus mercenaries.
0:47.3	When you're hiring early, you tend to want to hire missionaries because they're in love with the problem by definition.
0:53.3	They're just like in love with the mission and they'll ride the highs and lows and no problem's too low for them and beneath them.
1:00.0	Knowing when you found product market fit.
1:02.0	I've been trying to buy cap table software for me for like two weeks and nobody will pick up what's going on.
1:08.0	The problem was selling too quickly.
1:10.0	The problem is if you start selling before you figured out product market fit,
1:14.6	good GTM can actually hide bad product market fit for a while.
1:18.6	And then what happens is GTM's expensive, fucking expensive.
1:23.6	And the difference between an inputs versus outputs-driven culture.
1:32.0	It is very easy for a company to become outputs-driven.
1:33.5	How much did we book?
1:36.6	And I always tell him, revenue's lagging indicator.
1:39.1	That's the last thing we should look at.
	...

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