HubSpot CEO Brian Halligan on the Difficulty of Scaling Up

Updated On: September 10, 2019

Starting a business is no longer difficult, but scaling a business has become intensely tough. You not only need to be insanely great at basically everything, but you can't make many mistakes - or at least any of them twice. 

On this episode of Protect the Hustle, we talk to HubSpot's CEO and Co-Founder Brian Halligan about the process of scaling up, staying motivated with lofty goals, and tackling big meaty problems. Brian's used these skills to scale HubSpot to the #1 spot in the marketing automation market with a $4.7B market cap and is now taking on the sales and help desk markets. He also shares the story of getting "Wolf", the guitar made famous by Jerry Garcia of The Grateful Dead.

You can listen to Protect the Hustle on Apple Podcasts, Spotify, Google Podcasts, Overcast, Stitcher, Radio Public, or wherever you listen to podcasts. There's also a full video version below. The choice is yours. Choose wisely!

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Topics covered in this episode

  • The saga of Brian Halligan's purchase of Jerry Garcia's guitar

  • The differences of running a company with 2 to 20 people, 20 to 200 people, 200 to 2,000 people, and beyond

  • Recognizing that mistakes happen but ensuring that mistakes do not happen more than once

  • Maintaining high-performance, and how slacking in one area can lead to the downfall of the entire company

  • One person can't do everything in a scale-up; it's all about the team

  • Death by overeating vs starvation by not executing

  • Going into other markets after championing marketing automation

  • Maintaining focus on the long arduous journey of creating a great company

  • The hunger to be a pillar company in Boston that makes your children proud

  • Staying motivated by going after big meaty problems with horizon planning

Special thanks to Brian Halligan, whose book, "Inbound Marketing", is available now on Amazon or wherever you typically buy books.

We're giving away 25 copies of his book to the first 25 folks who leave a 5 star rating and comment on iTunes. Screenshot your review and email it to and we'll ship you out a copy.

Tags: interview, protect the hustle

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