Should You Start a Company? The Honest Truth
Executive Summary
My First Million episode 778 in which Sam Parr talks with Brian Halligan, co-founder and former CEO of HubSpot, about the highs and lows of building the company. Brian grades his own enjoyment by company size, saying he had what he calls CEO market fit between 10 and a thousand employees and enjoyed the larger stage less. He says founder work is at least a 996 schedule, that about 90 percent of the time things are broken, and that he still feels imposter syndrome. Chapters in the description also cover whether it ever stops sucking, whether the trade offs were worth it, whether AI is a bubble, whether you have to be liked, what he would do if he had to start over, and what he got wrong. Sponsors named in the description: HubSpot, Somewhere, Mercury and Beehiiv. PARTIAL COVERAGE: the captions cover the opening chapters in detail, and later chapters such as starting over and what he got wrong are named by title only. All views are Brian's and Sam's own and are not independently checked. Nothing here is medical, mental-health, financial or legal advice.
Key Takeaways
Happiness by company size
Brian says he rated himself a C at 2 to 10 employees, an A at 10 to 100 and a minus at 100 to a thousand.
CEO market fit
He says he had CEO market fit between 10 and a thousand employees.
Enjoying the passage of time
He says the secret of life is enjoying the passage of time, which he did not at the largest stage.
996 and beyond
He says founders work at least 996, and if they were not working they were thinking about working.
Mostly broken
He says about 90 percent of the time stuff is broken and the inbox is mostly bad news at any size.
Competitor paranoia
He says they tend to overestimate competitors and underestimate themselves.
Worth the trade-off
He says he would take the trade-off, that it was a lot of fun, though he is single and gave up family years.
The Conversation Breakdown
Happiness by company size
⏱ Untimed topicBrian says he rated himself a C at 2 to 10 employees, an A at 10 to 100 and a minus at 100 to a thousand.
CEO market fit
⏱ Untimed topicHe says he had CEO market fit between 10 and a thousand employees.
Enjoying the passage of time
⏱ Untimed topicHe says the secret of life is enjoying the passage of time, which he did not at the largest stage.
996 and beyond
⏱ Untimed topicHe says founders work at least 996, and if they were not working they were thinking about working.
Mostly broken
⏱ Untimed topicHe says about 90 percent of the time stuff is broken and the inbox is mostly bad news at any size.
Competitor paranoia
⏱ Untimed topicHe says they tend to overestimate competitors and underestimate themselves.
Worth the trade-off
⏱ Untimed topicHe says he would take the trade-off, that it was a lot of fun, though he is single and gave up family years.
Core Frameworks & Ideas
CEO market fit - Brian's idea
Notice which company size fits you and what work you enjoy.
Same ratio of bad news - Brian's view
Expect most days to bring problems at every size.
Uncertainty is the hard part - Sam's view
The harder part of founding is not risk but uncertainty about where time is going.
Actionable Next Steps
- ✓Write down which stage of work you enjoy most and why.
- ✓Notice if you overrate competitors and underrate your own team.
- ✓List what you gave up and what you got, to judge the trade-off for yourself.
- ✓Treat these founder views as personal accounts, not mental-health or career advice.
Notable Quotes
“the secret of life is enjoying the passage of time”
“90% of the time stuff's broken”
“We tend to overestimate where our competitors do and underestimate what we do”
The One Thing to Remember
Brian Halligan tells Sam Parr that building HubSpot meant constant work and mostly bad news, that his sweet spot was a company of 10 to a thousand people, and that he would take the trade-off again.