20VC: Hubspot Co-Founder Brian Halligan on Leadership Lessons Scaling Hubspot to a $28BN Market Cap | The Best Series A Investment in Venture History & What Makes Sequoia so Successful?

Posted on 15th January 2024 by Harry

Brian Halligan is the Co-Founder and Executive Chairperson of HubSpot. Brian led the business as CEO for 15 years from Day 1 to a $30BN public company with 7,000 employees. Among Brian numerous achievements, Brian is famed for coining the term “inbound marketing”, he is a globally recognised author, he is also an incredible teacher having developed MIT’s popular Scaling Entrepreneurial Ventures class. In addition to all of this, he is also the Co-Founder of Propeller Ventures, a $100 million climate tech venture fund, specializing in ocean innovation investments.

In Today’s Episode with Brian Halligan We Discuss:

1. The Makings of a Generational Defining Entrepreneur:

  • How did the first job as a paperboy lead to the founding of a $30BN company?
  • How does Brian analyse the importance of luck vs skill in success?
  • What is Brian running from? What is he running towards?

2. How to Be the Best Leader from 15 Years as CEO:

  • What are Brian’s biggest lessons in leadership from Elon Musk and Jensen Huang?
  • How has Brian’s leadership style changed over time?
  • Why is the way leaders prioritise what they do today completely broken?
  • How can leaders use quarterly goals to prioritise most effectively?
  • Does Brian believe people are born CEOs? Are MBAs worth it for CEOs?

3. How to Build the Best Team:

  • What is the #1 failure condition of teams today?
  • Why does Brian believe most of your employees are mercenaries and not missionaries? Is that ok?
  • Why do recovery plans never work? Once lost, can trust in teams be regained?
  • Are people destined for certain stages of company growth?
  • Why does culture always break when teams hit 100 people?

4. The Best Deal in VC History:

  • Why did Hubspot sell 47% of the company to General Catalyst in their Series A?
  • How did Sequoia come to lead their Series D?
  • How much of a needle mover is it for companies and founders to have Sequoia invest?
  • Why did Brian sell secondary to Sequoia in the Series D? Is it the most costly mistake he has made?

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