Masters in Business – Bloomberg

Episode: Carta CEO Henry Ward on Private Credit & Private Markets

Release Date: October 17, 2025
Host: Barry Ritholtz
Guest: Henry Ward, CEO & Co-Founder of Carta

Episode Overview

This episode features an in-depth conversation with Henry Ward, CEO and co-founder of Carta, the company transforming the management and digitization of private company equity infrastructure. Barry and Henry delve into the evolution of Carta from a niche software tool into a crucial underpinning of the private markets ecosystem, discuss the challenges unique to private data and liquidity, and explore the dynamics of entrepreneurship, scaling, and the changing landscape of private capital.

Key Discussion Points & Insights

1. Henry Ward’s Unconventional Path: Education, Military, and Early Career

• Education & Language Woes:
  • Began at Univ. of Michigan as a Math major, ended up with a General Studies degree after struggling with foreign languages, but deeply passionate about math and computers.
  • ("So it was me and 13 football players that graduated with a general studies degree that year. But my passion had always been math." — Henry Ward, 03:19)
• Brief Military Path:
  • Joined the Marines out of high school; later decided against a longer military career, opting instead to pay back GI Bill debt with a signing bonus.
  • "At the time, four years. Four more years in the Marines seemed like an eternity. Now it seems like nothing..." (04:20)
• Early Professional Experience:
  • Joined Trilogy in Austin, Texas, a formative stint in a high-powered tech company.

2. Path to Entrepreneurship—Lessons from Failure

• Second Site Failure and Motivation:
  • Ran robo-advisor startup Second Site (like Wealthfront/Betterment—the company failed but instilled a love for entrepreneurship).
  • "I couldn't imagine doing anything else as a completely failed founder. I just wanted to do it again. And Carta came out of that experience." (07:28)
• Love the Game, or the Problem?:
  • Discusses which motivates founders: passion for problem versus love of entrepreneurship. Cautions each path brings distinct strengths and weaknesses. (08:19-09:02)

3. Birth of Carta—Solving Cap Table Chaos

• Origin Story:

  • Inspired by direct experience and investor feedback, began by aiming to digitize the handling of stock certificates.
  • “The first version actually was PayPal for equity... We realized companies didn't care that much... but they said, well, hey, can you just put all of it into a table and show it to me? ...And that was the thing that had product market fit.” (09:36-10:53)

• Scaling Up & Technology Challenges:

  • Grew by focusing on solving actual customer problems, eventually building out from cap tables to a suite of related financial tools.

4. Digitizing Private Markets—Overcoming Skepticism

• Resistance to Change:
  • Venture capitalists and lawyers were initially reluctant to drop paper stock certificates in favor of digital, even in tech-forward Silicon Valley.
  • “Lawyers were like, no, but you have to have a green stock certificate... Like, that's what we've been doing literally for 200 years.” (13:25)
• Grassroots Adoption and Network Effects:
  • Startups adopted Carta for practical reasons (“1/10th the cost”), setting network effects in motion.
  • “Come for the tool, stay for the network... Once everybody started converging on the cap tables, it became the new standard.” (15:34)

5. Challenges in Scaling — Trials and Growth Pains

• Why Wasn’t It Done Before?
  • The “innovator’s dilemma”: Incumbents (investment banks, exchanges) didn’t see or seize the opportunity.
  • “The kind of person that would be filing paper stock certificates, would never come up with the idea of replacing them... There’s a certain level of intelligence and a certain level of stupidity that you need…” (20:34)
• Investor Skepticism and Market Expansion:
  • Early investors underestimated the market (“how many cap tables can you actually manage?”); saw the broader potential in building private market infrastructure.
  • Transitioned from a per-certificate fee to a more sustainable subscription model by candidly communicating with customers.
  • “I made a mistake, I priced this wrong...I hope, I understand if you decide to leave us, but I hope, I hope you won’t. And it was remarkable. We lost almost no customers.” (23:10-25:10)

6. Evolving the Carta Platform & Brand

• Category Expansion:
  • From legal tech to fintech to core infrastructure (including fund administration, benchmarking, compensation analytics, and more).
  • “I think over the first five years we transitioned the concept of cap table from a legal solution to a financial solution.” (26:17)
• Rebranding to Carta:
  • Needed broader identity and better domain than “E Shares”; purchased 'Carta.com' for $75K.
  • “As soon as we raised more money it became $10 million... so we decided we needed to change the name and we came up with Carta…” (27:47)

7. Entrepreneurship: Realities, Hardships, and the Role of Luck

• Scaling Lessons and Founder Grit:
  • Even as CEO, faces same challenges as early days, just “bigger, faster, harder.”
  • "It’s eating glass until you enjoy the taste of your own blood.” — quoting Marc Andreessen (29:14)
• The Luck Factor:
  • Ward emphatically acknowledges luck as a huge factor in successful entrepreneurship.
  • “Smart and hard work is just table stakes, you really have to get lucky. And people don’t understand the role of serendipity…” (31:38)
• Advice to Founders:
  • Urges founders to “love the game”—money is a poor motivator due to long periods of uncertainty and financial scarcity.
  • “If you do it for the money...you kind of quickly lose motivation because you’re poor for years...” (32:12)

8. Private Data & Why Software Firms Aren’t Data Vendors

• The Data Dilemma:
  • Carta maintains massive private market data but does NOT sell it, prioritizing client trust over monetizing data.
  • "Software businesses cannot be data businesses...if they monetize that data...customers won't trust them." (34:26-36:02)
  • Uses example of Salesforce as a firm that’s never become a data vendor despite having ample opportunity.

9. Shifts in Capital Markets: The Rise of Private Markets

• Private vs. Public Expansion:
  • Number of public companies shrinking; private markets booming, and most new job growth is in the private sector.
  • "Public markets is actually a shrinking industry...private companies is growing astronomically.” (37:28)
• Need for Broader Access:
  • Advocates for safe retail access to private markets rather than pushing companies to go public.
  • "I think the answer is to create safe access for everyday Americans into private capital." (39:07)

10. Private Market Liquidity: Myths & Realities

• Limits of Secondary Liquidity:
  • Skeptical that large-scale, public-style secondary trading for private startups is achievable; structural market differences impede it.
  • "Private markets are so different from public...In private markets, easier to sell $100 million block than it is to sell one share." (42:12)
  • Attempts to create liquidity at scale have generally been niche, not consolidated.
  • “In private markets...liquidity does not beget liquidity. As soon as one of these companies starts to scale...it devolves back down to a niche business.” (44:03)

11. Expansion Opportunities & Adjacent Markets

• Decision Framework:
  • Criteria for Carta’s expansion: right to win, and speed to win.
  • Sometimes leads to less obvious adjacencies, e.g., cap tables → valuations, cap tables → fund accounting.
  • "We have a really strict framework...do we have a right to win? ...can we win that market quickly?" (48:13)

12. Compensation Analytics & Startup Employee Mindset

• Salary vs. Equity:
  • Partnership with Morgan Stanley aims to fill the gap in financial advisory for employees with substantial but illiquid equity.
  • "If I'm an employee and...I'm sitting on a million or $2 million of equity, illiquid equity. How do I think about that? There is no industry for that." (51:38)
  • Many startup employees now prioritize reliable cash over potential equity windfalls.

Notable Quotes & Memorable Moments

• On the Joy (and Pain) of Building
  "It’s eating glass until you enjoy the taste of your own blood."
  — Henry Ward (quoting Marc Andreessen), (29:14)

• On Luck in Entrepreneurship with Humility
  "I had to flip tails 32 times in a row to get to where I am."
  — Henry Ward (30:41)

• On Investment Market Size Miscalculations
  "Early investors said... the market size is too small. ...We were wrong. It turned out the cap table business was way bigger than we and investors thought."
  — Henry Ward (21:18)

• On Trust and Data Business Models
  “If they monetize that data on the other side...it cannibalizes their software business because the customers won't trust them now...”
  — Henry Ward (34:26)

• On Private Market Access
  "I think it will be weird in 20 or 30 years, it will be weird that we locked out 99% of Americans out of private capital."
  — Henry Ward (46:12)

Timestamps for Key Segments

• 03:00 — Henry’s educational journey, military detour, and first jobs
• 07:17 — Learning from startup failure, differences in founder motivation
• 09:20 — “Aha” moment: digitizing equity management
• 13:25 — Overcoming industry skepticism to digitize equity
• 20:34 — Why incumbents missed the opportunity (the innovator’s dilemma)
• 23:10 — Pricing model pivot: adopting subscriptions, communicating with customers
• 26:17 — From legal-tech to fintech to infrastructure
• 27:22 — Rebranding from E Shares to Carta
• 29:14 — The pain and chance of scaling as an entrepreneur
• 34:26 — Why Carta doesn’t (and won’t) sell private market data
• 37:28 — Testifying before Congress: growth, access, and private markets
• 42:12 — Why public-style liquidity will not likely happen for private startup equity
• 48:13 — Decision structure for pursuing new lines of business
• 51:38 — The challenge of providing employee financial advice for illiquid assets

Rapid-Fire: Mentor & Advice Section (54:06+)

• Mentors: Highlights various personal and industry mentors, stresses learning from many sources (boxing coach, Marines, Marc Andreessen, John Waldron at Goldman).
• Books: "Amp it Up" (recent read with Carta leadership team)
• Advice to Grads: Encourages “mountain jumping”—trying different career paths to maximize potential.
  • "I encourage people early to jump mountains to figure out which mountain they want to be on." (57:51)
• Big Epiphany: Success needs both high skill and luck; increased competition makes entrepreneurship harder, not easier.

Final Thoughts

Henry Ward’s journey—from college, the military, and startup failures to building Carta as private market infrastructure—offers a candid look at the quirks and core obstacles of entrepreneurship and fintech innovation. The episode is an essential listen for anyone interested in private markets, startup life, or the evolution of financial infrastructure.

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