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20VC: How To Drop The BS and Relationship Build With Investors, What Investors Can vs Cannot Help Your Company With & Why When There Is Doubt There Is No Doubt In Hiring

Oct 4, 2019

Jason Boehmig, Founder and CEO of Ironclad, dives into the intersection of law and tech. He shares insights on transitioning from a corporate attorney to leading a successful startup, emphasizing the importance of conviction and customer discovery in product development. His approach to hiring challenges the norms; he believes in prioritizing cultural fit and intuition over traditional metrics. Jason also discusses the invaluable lessons learned during his time at Lehman Brothers and how they shape his leadership style today.

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ANECDOTE

The Importance of Contracts

Jason Boehmig's interest in contracts stemmed from his belief that they are the most important business technology ever invented.
He wanted to bring contracts into the digital age and help restore the legal profession.

INSIGHT

Independent Thinking

Jason's experience at Lehman Brothers taught him the importance of independent thinking and managing one's own psychology.
He learned to question assumptions and develop his own convictions.

ADVICE

Customer Obsession

Focus on a small geographic area when starting product development.
This allows for rapid iteration and direct customer feedback.

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Jason Boehmig is the Founder & CEO @ Ironclad, the startup that provides powerful legal contracting for modern legal teams. To date, Jason has raised over $84m with Ironclad from some of the best in the business including Sequoia, Accel, Greylock, Emergence, IA Ventures, Semil Shah's Haystack and Ali Rowghani who led their recent $50m Series C from Y Combinator Continuity Fund. As for Jason, prior to founding Ironclad, he was both a corporate attorney with Fenwick & West and then also an adjunct professor of Law at the University of Notre Dame.

In Today’s Episode You Will Learn:

1.) How Jason left the world of law and made his way into the world of startups and came to be founder of one of Silicon Valley's hottest startups, Ironclad? How did Jason's experience at Lehmann Brothers impact his operating mentality today as a founder? What were his big lessons on personal conviction from seeing Lehmann unravel?

2.) Ironclad is famed for their customer discovery process, so how does Jason think about product development in the early days? What core questions does Jason ask to understand customer needs and desires? How does Jason determine what to implement and what to prioritise? How does Jason think about the balance between data vs gut in product decision-making? What have been his lessons here?

3.) When it comes to hiring, how does Jason approach keeping top of funnel constantly full? Why does Jason believe that when hiring, "when there is doubt, there is no doubt"? What are the common reasons that Jason does not hire a potentially strong candidate? How does Jason determine between a stretch VP and a stretch too far?

4.) How does Jason think about relationship building with VCs? Where do so many founders make mistakes in this process? What advice does Jason have on successfully negotiating with VCs? What works? What does not? What value-add has Jason realised VCs really can and do provide? Where is there a suggestion that they do but rarely do?

Items Mentioned In Today’s Show:

Jason’s Fave Book: Meditations by Marcus Aurelius

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