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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?

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Jan 15, 2024

Brian Halligan, Co-founder and Executive Chairperson of HubSpot, shares insights from his journey scaling the company to a $30 billion powerhouse. He discusses the balance of luck and skill in entrepreneurship, revealing how his early job as a paperboy shaped his leadership approach. Halligan reflects on invaluable lessons learned from leaders like Elon Musk, the importance of effective team dynamics, and the evolving role of CEOs in today's business landscape. He also critiques the venture capital space, offering wisdom from HubSpot's fundraising adventures.

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ANECDOTE

Paperboy to CEO

Brian Halligan's first job was as a paperboy, where he met the Harrisons.
This connection led to his first real job after college, highlighting the unexpected benefits of early work experiences.

INSIGHT

Luck Favors the Prepared

Luck plays a significant role in success, but preparation is key.
Being well-prepared increases the chances of being at the right place at the right time.

ANECDOTE

Choosing the Right Rocket Ship

Halligan chose a lower-paying job at PTC over higher-paying sales positions.
This decision, based on the company's growth potential, significantly benefited his career trajectory.

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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?