Brian Halligan | Crain's

In this ongoing series, we ask executives, entrepreneurs and business leaders about mistakes that have shaped their business philosophy.

Brian Halligan


HubSpot's marketing platform is designed to draw customers in through content marketing, email marketing, social media and analytics, among other services.

The Mistake:

When we started the idea, we were in business school and very much inspired by Steve Jobs at Apple. We had a field trip to California and a few of us got to meet with Jobs, the messiah, and sit in the audience and listen to him. He described how he built the iPod — this was before the iPhone and all that other stuff, years ago — and he got into a lot of detail. He spent a couple hours with us. The way he described the problem he was solving was similar to the way we were trying to solve some problems at Hubspot. So he was in our mind and in our vernacular as we started the company.

I grew enamored with Jobs, like probably 90 percent of business leaders. I read everything that ever came out about him, watched every one of his keynotes, read every article. Since he died, I've watched every movie about him, every documentary, read the book twice. I was quite convinced that I was Steve Jobs. I convinced myself that I can do this, it's not that hard. I can get up on stage and give a presentation. I convinced myself that I have brilliant design skills and that I am a brilliant product person.

I lean in around my strengths, and hire around my weaknesses.

And so I spent a lot of time on the product. Hours and hours, days and days, really involved with product development and design, and directly managing those people. It took a solid four years to figure out that I have no talent when it comes to design, and no talent when it comes to product management, and any of the stuff Steve Jobs is brilliant at, I am the exact opposite of what Steve Jobs is. In fact, we share no DNA in terms of our skillset. I guess my "ah-ha" cost Hubspot a lot of opportunity and money before we hired real product design people that knew what they were doing.

The Lesson:

It had a lot of impact. We hired a COO who actually knows how to run a company, which is helpful. The mechanics of the rest of the business, I'm aware of it, I know about it, I've got ideas about it, but for the most part, I find other people who can manage much better than I can. I lean in around my strengths, and hire around my weaknesses. A lot of people say, "What are your strengths and weaknesses? You gotta work on your weaknesses." Ah, forget it. Hire somebody who can cover up for your weaknesses and get good at your strengths. Because if I can put a calorie into my strengths, I'll get a much higher return than if I put a calorie into my weaknesses.

Follow Brian Halligan on Twitter at @bhalligan.

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