Sequoia CEO coach: Why it’s never been easier to start a company, and never been harder to scale one | Brian Halligan (co-founder, HubSpot)
Brian Halligan co-founded HubSpot, ran it as CEO for about 15 years, and now coaches Sequoia’s fastest-growing founders as their in-house CEO coach.
We discuss:
1. His LOCKS framework for evaluating founders
2. Why you should build your team like the 2004 Red Sox
3. Why hiring “spicy” candidates beats consensus picks
4. Why enterprise sales will be the last white-collar job AI replaces
5. Some of my favorite “Halliganisms”
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Episode transcript: https://www.lennysnewsletter.com/p/sequoia-ceo-coach-why-its-never-been
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Archive of all Lenny's Podcast transcripts: https://www.dropbox.com/scl/fo/yxi4s2w998p1gvtpu4193/AMdNPR8AOw0lMklwtnC0TrQ?rlkey=j06x0nipoti519e0xgm23zsn9&st=ahz0fj11&dl=0
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Where to find Brian Halligan
• X: https://x.com/bhalligan
• LinkedIn: linkedin.com/in/brianhalligan
• Delphi: https://www.delphi.ai/bhalligan
• Podcast: https://sequoiacap.com/series/long-strange-trip
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Where to find Lenny:
• Newsletter: https://www.lennysnewsletter.com
• X: https://twitter.com/lennysan
• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/
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In this episode, we cover:
(00:00) Introduction to Brian Halligan
(03:56) The perpetual state of constructive dissatisfaction
(05:25) Coaching CEOs
(07:49) The art of interviewing and hiring
(11:21) Getting the most out of reference calls
(13:10) Homegrown talent vs. big company hires
(16:31) Traits of successful CEOs
(19:40) Brian’s LOCKS framework for evaluating founders
(21:34) Are great CEO’s born or made?
(23:41) Giving effective feedback
(25:54) The future of go-to-market strategies
(31:56) Understanding forward deployed engineers
(34:17) How the CEO role has evolved over the last 20 years
(38:10) Halliganisms
(01:01:18) The CEO’s role in scaling a company
(01:02:41) Lightning round and final thoughts
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Referenced:
• Dev Ittycheria on LinkedIn: https://www.linkedin.com/in/dittycheria
• HubSpot: https://www.hubspot.com
• Parker Conrad on LinkedIn: https://www.linkedin.com/in/parkerconrad
• McKinsey & Company: https://www.mckinsey.com
• Brian Chesky’s new playbook: https://www.lennysnewsletter.com/p/brian-cheskys-contrarian-approach
• Jensen Huang on LinkedIn: https://www.linkedin.com/in/jenhsunhuang
• Winston Weinberg on LinkedIn: https://www.linkedin.com/in/winston-weinberg
• James Cadwallader on LinkedIn: https://www.linkedin.com/in/jsca
• Gabriel Stengel on LinkedIn: https://www.linkedin.com/in/gabestengel
• He saved OpenAI, invented the “Like” button, and built Google Maps: Bret Taylor on the future of careers, coding, agents, and more: https://www.lennysnewsletter.com/p/he-saved-openai-bret-taylor
• Scaling Entrepreneurial Ventures: https://orbit.mit.edu/classes/scaling-entrepreneurial-ventures-15.392
• OpenClaw: https://openclaw.ai
• Ruth Porat on LinkedIn: https://www.linkedin.com/in/ruth-porat
• Mike Krzyzewski: https://goduke.com/sports/mens-basketball/roster/coaches/mike-krzyzewski/4159
• Dalai Lama’s 18 Rules for Living: https://www.prm.nau.edu/prm205/Dalai-Lama-18-rules-for-living.htm
• Zigging vs. zagging: How HubSpot built a $30B company | Dharmesh Shah (co-founder/CTO): https://www.lennysnewsletter.com/p/lessons-from-30-years-of-building
• Kareem Amin on LinkedIn: https://www.linkedin.com/in/kareemamin
• Glassdoor: https://www.glassdoor.com
• Tobi Lütke’s leadership playbook: Playing infinite games, operating from first principles, and maximizing human potential (founder and CEO of Shopify): https://www.lennysnewsletter.com/p/tobi-lutkes-leadership-playbook
• Katie Burke on LinkedIn: https://www.linkedin.com/in/katie-burke-965767a
• Jerry Garcia: https://en.wikipedia.org/wiki/Jerry_Garcia
• Bob Weir: https://en.wikipedia.org/wiki/Bob_Weir
• Phil Lesh: https://en.wikipedia.org/wiki/Phil_Lesh
• Ron “Pigpen” McKernan: https://en.wikipedia.org/wiki/Ron_%22Pigpen%22_McKernan
• Marc Andreessen: The real AI boom hasn’t even started yet: https://www.lennysnewsletter.com/p/marc-andreessen-the-real-ai-boom
• The American Revolution: https://www.pbs.org/kenburns/the-american-revolution
• Delphi: https://www.delphi.ai
• Sonos: https://www.sonos.com
• Yamini Rangan on LinkedIn: https://www.linkedin.com/in/yaminirangan
• The Boston Red Sox: https://www.mlb.com/redsox
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Recommended book:
• Marketing Lessons from the Grateful Dead: What Every Business Can Learn from the Most Iconic Band in History: https://www.amazon.com/Marketing-Lessons-Grateful-Dead-Business/dp/0470900520
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Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.
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Lenny may be an investor in the companies discussed.
To hear more, visit www.lennysnewsletter.com
7 Brutal Questions for a $20B Founder
Get Sam's AI Executive Coach Playbook - his exact system for everything from revenue optimization to life decisions: https://clickhubspot.com/dhn
Episode 778: Sam Parr ( https://x.com/theSamParr ) talks to Brian Halligan ( https://x.com/bhalligan ) about the highs and lows of building HubSpot.
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Show Notes:
(0:00) Are you happy?
(2:57) Does it ever stop sucking?
(5:18) Do you have imposter syndrome?
(6:55) Were the trade offs worth it?
(11:53) Is AI a bubble?
(14:47) Do you have to be liked?
(17:02) What would you do if you had to start over?
(29:36) What did you get wrong?
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Links:
• Marketing Lessons From The Grateful Dead - https://tinyurl.com/ydmyh6f9
—
Check Out Shaan's Stuff:
• Shaan's weekly email - https://www.shaanpuri.com
• Visit https://www.somewhere.com/mfm to hire worldwide talent like Shaan and get $500 off for being an MFM listener. Hire developers, assistants, marketing pros, sales teams and more for 80% less than US equivalents.
• Mercury - Need a bank for your company? Go check out Mercury (mercury.com). Shaan uses it for all of his companies!
Mercury is a financial technology company, not an FDIC-insured bank. Banking services provided by Choice Financial Group, Column, N.A., and Evolve Bank & Trust, Members FDIC
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Check Out Sam's Stuff:
• Hampton - https://www.joinhampton.com/
• Ideation Bootcamp - https://www.ideationbootcamp.co/
• Copy That - https://copythat.com
• Hampton Wealth Survey - https://joinhampton.com/wealth
• Sam’s List - http://samslist.co/
My First Million is a HubSpot Original Podcast // Brought to you by HubSpot Media // Production by Arie Desormeaux // Editing by Ezra Bakker Trupiano //
SaaStr 784: What Really Works When Hiring VPs and Executive Teams with HubSpot Co-Founder and Chairman Brian Halligan and SaaStr CEO and Founder Jason Lemkin
SaaStr 784: What Really Works When Hiring VPs and Executive Teams with HubSpot Co-Founder and Chairman Brian Halligan and SaaStr CEO and Founder Jason Lemkin
The success rate for executive hires at high-growth SaaS companies can be surprisingly low - you're often lucky if 50-60% of your management team works out long-term. In a recent conversation between HubSpot Chairman and co-founder Brian Halligan and SaaStr Founder and CEO Jason Lemkin, they shared their advice on what actually works when hiring VPs and building your SaaS executive team.
SaaStr 783: HubSpot Co-Founder and Chairman Brian Halligan on SaaS Markets and AI (Part 1)
SaaStr 783: HubSpot Co-Founder and Chairman Brian Halligan on SaaS Markets and AI (Part 1)
SaaStr CEO and Founder Jason Lemkin recently sat down with HubSpot Chairman and co-founder Brian Halligan, who shared valuable insights on the current state of SaaS, evolving board meeting formats, and how AI is reshaping the industry. Here are the key takeaways from part 1 of this interview.
00:00 Introduction and Guest Overview 01:00 Early Days and Growth of HubSpot 02:41 IPO Reflections and Market Insights 04:06 Regrets and Lessons Learned 06:38 Public Company Challenges and Board Dynamics 14:03 Innovative Board Meeting Formats 21:15 The Dreaded Monday Morning Meeting 22:10 Meta Learnings and SaaS Market Vibe Check 22:55 Navigating the SaaS Downturn 24:35 Challenges for SaaS Companies in 2024 29:11 AI in B2B: Who Wins? 32:46 The Future of AI and Pricing Models 36:18 AI Parity and Customer Support 40:31 Real-World AI Implementation Challenges --------------------------------------------------------------------------------------------
SaaStr hosts the largest SaaS community events on the planet.
Hey everybody - thanks to the 10,000 of you who came out to SaaStr Annual. We had a blast and big news -- we'll be back in MAY of 2025. That's right, the SaaStr Annual will be a bit earlier next year, May 13-15 2025. We'll still be back in the same venue, in the SF bay area at the 40+ acre sprawling san mateo county events center. Grab your tickets at saastrannual.com with code JASON50 for an extra discount on our very best pricing.
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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?
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?
From App to Suite to Platform, with HubSpot's Co-Founder Brian Halligan
Startups aren't the only companies racing to build the new world of AI. This week, Sarah Guo talks with Brian Halligan, the co-founder, longtime CEO and now executive chairperson of HubSpot, the fastest growing CRM. He talks about category creation, coining the term ‘inbound marketing,’ lessons in scaling from an app to a suite to a platform, staying innovative at scale, and how they're navigating the AI disruption. Brian also describes the life-threatening moment he decided to step back from the CEO role. Plus, what he’s up to at Propeller Ventures and why he’s banking on the ocean to save us from climate change.
Brian coined the term "inbound marketing" and together with Dharmesh Shah built a movement around the concept, which included organizing the industry-leading INBOUND event and co-authoring the book Inbound Marketing. Now, as the founder of Propeller Ventures, Brian directs a $100 million climate tech venture fund, specializing in ocean investments. He also serves on the boards of Navier and Aquatic Labs. Brian developed MIT’s popular Scaling Entrepreneurial Ventures class, which he’s taught for over a decade.
Show Links:
Brian Halligan | LinkedIn
Propeller VC
WHOI Partnership
HubSpot Culture Code
Read his books: Inbound Marketing and Marketing Lessons From the Grateful Dead
Sign up for new podcasts every week. Email feedback to show@no-priors.com
Follow us on Twitter: @NoPriorsPod | @Saranormous | @EladGil |@BHalligan
Show Notes:
(0:00:00) - HubSpot's Journey from Unlikely Startup to Industry Incumbent
(0:05:32) - The End of Cold Calling (and the Birth of Inbound)
(0:16:40) - Building a Multi-Product Company
(0:22:07) - How to Stay Innovative and Hungry after Going Public
(0:29:12) - AI Workflows in CRM and the Incumbent Data Advantage
(0:36:09) - Creating a Culture Code for HubSpot
(0:40:24) - Propeller Venture Fund, Ours Oceans and Climate Investing
EP 57: Brian Halligan (Co-founder, HubSpot) - The Path to Building a $20B Business
In the 57th episode of The Logan Bartlett Show, HubSpot Co-founder Brian Halligan joins to discuss his near-death experience, building a $20B company, and how Apple and Grateful Dead have influenced HubSpot.
(0:00) Intro
(2:15) Snowmobile Accident
(15:36) HubSpot Going Public
(26:57) Inbound vs. Outbound
(32:54) HubSpot vs. Salesforce
(39:10) iPod Influence
(43:10) Grateful Dead and Black Licorice
(58:01) HubSpot Culture
(1:04:44) Learning from Mistakes
(1:11:02) Brian’s Schedule
(1:14:45) Climate
Mixed and edited: Sam Dewees
Produced: Rashad Assir
Executive Producer: Josh Machiz
Music: Griff Lawson
🎙 Listen to the show
Apple Podcasts: https://podcasts.apple.com/us/podcast/three-cartoon-avatars/id1606770839
Spotify: https://open.spotify.com/show/5WqBqDb4br3LlyVrdqOYYb?si=3076e6c1b5c94d63&nd=1
Google Podcasts: https://podcasts.google.com/feed/aHR0cHM6Ly9mZWVkcy5zaW1wbGVjYXN0LmNvbS9zb0hJZkhWbg
🎥 Subscribe on YouTube: https://www.youtube.com/channel/UCugS0jD5IAdoqzjaNYzns7w?sub_confirmation=1
Follow on Socials
📸 Instagram - https://www.instagram.com/theloganbartlettshow
🐦 Twitter - https://twitter.com/loganbartshow
🎬 Clips on TikTok - https://www.tiktok.com/@theloganbartlettshow
About the Show
Logan Bartlett is a Software Investor at Redpoint Ventures - a Silicon Valley-based VC with $6B AUM and investments in Snowflake, DraftKings, Twilio, Netflix. In each episode, Logan goes behind the scenes with world-class entrepreneurs and investors. If you're interested in the real inside baseball of tech, entrepreneurship, and start-up investing, tune in every Friday for new episodes.
Executive Producer: Rashad Assir
Producer: Leah Clapper
Mixing and editing: Justin Hrabovsky
Check out Unsupervised Learning, Redpoint's AI Podcast: https://www.youtube.com/@UCUl-s_Vp-Kkk_XVyDylNwLA
🎥 Subscribe on YouTube: https://www.youtube.com/channel/UCugS0jD5IAdoqzjaNYzns7w?sub_confirmation=1
Follow on Socials
📸 Instagram - https://www.instagram.com/theloganbartlettshow
📱 X - https://twitter.com/loganbartshow
🎬 Clips on TikTok - https://www.tiktok.com/@theloganbartlettshow
About the Show
Logan Bartlett is a Software Investor at Redpoint Ventures - a Silicon Valley-based VC with $6B AUM and investments in Snowflake, DraftKings, Twilio, and Netflix. In each episode of The Logan Bartlett Show, we sit down with the people behind today’s most important startups and extract the tactics, lessons, and frameworks they’ve learned the hard way. Conversations span hiring to GTM, product, growth, fundraising and everything in between - collectively forming the ultimate playbook to make you a better CEO, investor or board member.
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How to calculate "Bottom-up TAM" + Hubspot Co-Founder Brian Halligan on his new climate fund | E1634
J+M kick off the show discussing TAM, SAM, and SOM on this week’s edition of VCSS. (2:40) Then, HubSpot Co-Founder and Partner at Propeller Brian Halligan joins Molly to discuss his $100M venture fund to invest in protecting the world’s oceans. (26:00)
(0:00) J+M tee up today's segments!
(2:40) Exceeding your TAM + overestimating your TAM
(7:39) House of Macadamias - Get 20% off at https://houseofmacadamias.com/twist by using code TWIST20
(9:07) Inducing a market and Bottom-up TAM
(21:15) AgeTech Collaborative - Find out more and apply at https://agetechcollaborative.org/twist
(22:49) Molly introduces Brian Halligan
(26:00) Why the ocean + from founder to investor
(38:00) AgeTech Collaborative - Find out more and apply at https://agetechcollaborative.org/twist
(39:39) Propeller’s investments, their EIR program & thesis
FOLLOW Brian: https://twitter.com/bhalligan
FOLLOW Jason: https://linktr.ee/calacanis
FOLLOW Molly: https://twitter.com/mollywood
Subscribe to our YouTube to watch all full episodes:
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SaaStr 600: Founder Confidential with HubSpot Founder and CTO Dharmesh Shah, & Founder and Executive Chairperson Brian Halligan
Tune into Founder Confidential with SaaStr CEO Jason Lemkin and Hubspot Founders Dharmesh Shah and Brian Halligan to hear their key learnings and considerations of what it takes to be a Founder in today's SaaS landscape.
Full video: https://youtu.be/gn01HIUyE9M
Want to join the SaaStr community? We're the 🌎largest community for B2B software.
Subscribe for weekly updates: https://www.saastr.com/subscribeform
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Near Death Accidents, Hitting $1B ARR, and Selling Like the Grateful Dead with Brian Halligan, Founder & Executive Chairman of HubSpot
Brian Halligan (@BHalligan), founder & executive chairman (and former CEO) of HubSpot, joins Sam (@TheSamParr) and Shaan (@ShaanVP) to discuss what he learned from nearly dying in a snowmobile accident, how he took HubSpot from nothing to $1 billion in ARR, and what he learned about marketing from the Grateful Dead. He also discusses what he does day-to-day, why he has always preferred inbound marketing, how to manage creatives, and much more.
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Show Notes:
* (1:37) Brian’s snowmobiling accident that nearly killed him
* (7:18) How Brian’s life has changed since
* (13:07) What Brian actually does day-to-day
* (28:39) Why has always Brian preferred inbound marketing
* (32:00) Businesses that can be built on top of HubSpot
* (33:34) Org chart business opportunities
* (36:14) Climate Tech Opportunities
* (50:50) How to Manage Creatives
* (55:35) What the Grateful Dead can teach us about marketing
SaaStr 430: The Secrets to $1B ARR and 100,000 Happy Customers with Brian Halligan, CEO and Co-Founder @ HubSpot, and Jason Lemkin, CEO and Founder @ SaaStr
In today's SaaStr insider episode, SaaStr CEO and Founder, Jason Lemkin catches up with Brian Halligan, CEO and Co-founder of HubSpot. Together they discuss: why partners are a moat, why HubSpot avoided going more enterprise, building vs. buying, and building an eco-system.
Video + blog post: https://www.saastr.com/brian-halligan-ceo-and-co-founder-at-hubspot-the-secrets-to-1b-arr-and-beyond/
E997: HubSpot CEO & Co-founder Brian Halligan shares insights on the origin of inbound marketing, how The Grateful Dead inspired HubSpot, importance of customer experience, managing employees in the Glassdoor Era & more
0:52 Jason intros Brian Halligan
1:35 Brian describes how his job has changed as HubSpot has scaled
3:33 Jason asks Brian about buying Jerry Garcia's guitar "Wolf"
4:42 Jason & Brian reminisce over Grateful Dead shows at Giants Stadium
6:36 How the Grateful Dead pioneered "Inbound Marketing" & inspired HubSpot
15:24 How Brian met his Co-founder Dharmesh Shah
17:04 The original idea behind HubSpot
19:18 Ray Ozzie's impact on HubSpot & Brian
25:34 Benefits of introversion
30:06 Succession planning in tech
33:24 Avoiding pot-holes as CEO
35:18 Importance of customer experience in 2019
38:45 Examples of creating a great end-to-end customer experience
49:43 How Brian keeps himself sharp & motivated
52:45 Managing employees from different generations in the "Glassdoor Era"
SaaStr 254: HubSpot CEO Brian Halligan on The Funnel is Dead, Long Live the Flywheel.
The age-old sales funnel has worked fine for decades…until now. Flaws are being exposed, and a new model is imminent. Why is the sales funnel alone no longer an appropriate way thinking about customers? What will emerge to supplement or replace it? HubSpot CEO Brian Halligan and NEA's Hilarie Koplow-McAdams explore the evolution of the marketing and sales funnel you've been using for decades to generate traffic and convert and leads into customers.
Missed the session? Here's what Brian talks about:
Why a flywheel instead of a funnel?
What does the Grateful Dead have to do with Marketing…?
What role do T shaped people play?
If you would like to find out more about the show and the guests presented, you can follow us on Twitter here:
Jason Lemkin
SaaStr
Brian Halligan
