Running a Side Venture Fund

What happens when AI turns a $40B legal software market into a $1T opportunity? In this episode, I talk with David Eckstein, CFO of Legora, about scaling one of the fastest growing enterprise AI companies in history. David explains how Legora went from zero to $100M in 18 months, why AI is expanding markets rather than just disrupting them, and how the role of CFO is evolving into a strategic operator across every part of the business. We discuss vertical vs horizontal AI, why AI companies must focus on workflows instead of prompts, and how talent density and culture become the ultimate differentiators in high growth environments.

Highlights:

• How Legora scaled from 0 to $100M in 18 months
• Why legal tech is a $1T opportunity, not just $40B
• Vertical AI vs horizontal AI and why workflows matter
• Why AI expands TAM rather than just disrupting it
• CFO as operator, not just finance leader
• How AI changes pricing, margins, and business models
• Talent density as the most important investment
• Why culture and intensity drive execution speed
• Lessons from Box and transitioning into venture
• The importance of moving fast in emerging markets

Guest Bio:

David Eckstein is the Chief Financial Officer at Legora, where he leads financial strategy, operations, and scaling for one of the fastest growing AI companies globally. Prior to Legora, he served as CFO at Vanta and Menlo Security, helping both companies scale rapidly and raise significant capital. Earlier in his career, he held leadership roles at OpenDNS and Box, including through OpenDNS’s $635M acquisition by Cisco, and began his career in technology investment banking at Barclays Capital.

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Sponsor:

AlphaSense is the AI-powered market intelligence platform trusted by 85% of the S&P 100, helping investment professionals make faster, more confident, data-driven decisions. Built for hedge funds, asset allocators, private venture capital firms, and investment bankers, AlphaSense uses advanced AI and powerful search across premium proprietary content to surface the insights that matter most—before the market moves. Elevate your research and stay ahead of the competition. Visit https://www.alpha-sense.com/howiinvest/ to learn more.

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Stay Connected with David Eckstein:

LinkedIn: https://www.linkedin.com/in/davidneckstein/

Questions or topics you want us to discuss on How I Invest? Email us at david@weisburdcapital.com.

Disclaimer:

This podcast is for informational purposes only and does not constitute investment, financial, legal, or tax advice. Nothing in this episode should be interpreted as an offer to buy or sell any securities or to participate in any investment strategy. All opinions expressed by the host and guests are their own and do not represent the views of Weisburd Capital. Participants may hold positions or have financial interests in the companies, funds, or investments discussed. Any references to specific investments are for illustrative purposes only. Investing involves risk, including the potential loss of capital. Past performance is not indicative of future results, and any forward-looking statements are subject to risks and uncertainties. Any third-party data or opinions have not been independently verified. Listeners should conduct their own research and consult their own advisors before making any investment decisions.

(0:04) How Legora Became the Fastest Growing Enterprise Company Ever (1:50) Why Vertical AI Is Beating the Giants (3:05) The Hidden Upside: When Lower Costs Explode Demand (4:51) Why OpenAI Won’t Replace Companies Like Legora (7:27) Why the Best Founders Ignore Competition Completely (9:17) The “Win at All Costs” Culture Behind Hypergrowth (12:48) Why Raising More Money Can Actually Slow You Down (14:50) The Culture That Benchmark Called “Special” (18:42) Why Working 100 Hours Doesn’t Feel Like Work (22:35) The Biggest Career Risk No One Talks About