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?
The Twenty Minute VC (20VC): Venture Capital | Startup Funding | The Pitch
The Twenty Minute VC
4.4 • 637 Ratings
🗓️ 15 January 2024
⏱️ 76 minutes
🧾️ Download transcript
Summary
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?
Transcript
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| 0:00.0 | When we did our Series A, it was a $5 million round on a $6 million pre-money valuation. So we sold 40, 70% of our company in Series A. That was standard, Harry. We had a half a million dollars from revenue growing fast or maybe even a million. It was doing all right. Series D. Our last meeting was a guy named Jim Gets. Jim Gets is kind of a legendary VC at Sequoia, sitting in a conference and I was nervous. And Jim walks in and as I'm shaking his hand, like my hand is moving up and down like this. He says to me, hey, Brian, what's it going to take for Sequoia to own a piece of hub spot? And I said, really not much. Just give me a turbship. I'm ready to go. I had no other options. This is 20 VC with me, Harry Stebbings, and I've wanted to have this guest on for a long time. |
| 0:41.4 | For years, VCs said SMBs, ah, it's a bad market, they churn, they don't pay much. |
| 0:47.7 | Well, this guest today went against all odds and built a $28 billion juggernaut selling purely to SMBs, HubSpot. |
| 0:56.0 | I'm so excited to welcome Brian Halligan, co-founder and exec chairperson. |
| 1:00.0 | Brian led the business as CEO for 15 years, from day one to a $30 billion public company with 7,000 employees. |
| 1:09.0 | Fun fact, Brian is also famed for coining the term |
| 1:11.9 | inbound marketing. Following a horrific skiing accident, which we do discuss in the show, |
| 1:16.7 | Brian stepped down as CEO of HubSpot, and today is the co-founder of Propeller Ventures, |
| 1:21.6 | a $100 million climate tech venture fund, specialising in ocean innovation investments. |
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