Recently I got the opportunity to interview 6-time entrepreneur and Hubspot's Former Chief Product Officer David Cancel. David is one of those few entrepreneurs who has built and exited multiple companies including BuyerZone.com (acquired), Compete (acquired), Lookery (acquired), Ghostery (acquired) and Performable (acquired by Hubspot). Today, he currently serves as the CEO of Drift, a customer engagement, and tracking platform. David now hopes to share some of these lessons he has learned throughout the years in his recently launched podcast called Seeking Wisdom.

In our one hour interview, we covered all sorts of topics ranging from what it takes to build a successful startup to war stories during the dot-com bubble to how to build a great product that users love. Here are a few of the top insights I gained from our interview.

1. It's a marathon, not a sprint

One of the first things we talked about was David's experience building Compete despite the dot-com crash and how it took him 4 years to really get the startup running off the ground.

"Once we had started the company, we were already pregnant. There was no turning back. We had started a company, we raised money, we had a team. The world was crumbling around us and there was nothing we could do but continue. It's clich now but starting a startup is a marathon and not a sprint. It really hit home because it was a really long journey. It's a 5-10 year commitment and you have to be ready for that."

2. Take it one day at a time

While there were a lot of sleepless nights, painful layoffs and countless of other challenges during the dot-com bubble, David and his team were able to overcome all these by taking them on one day at a time.

"It was one day at a time. It was so hard. There were a lot of days and nights full of anxiety. Just being nervous and freaked out, not knowing what was going to happen. We had two rounds of layoffs and it was heart-breaking because some of them, the reason they had joined the company was me convincing them to join. How were we going to turn this company around? Then eventually the market changed in 2004 but it was a really hard time and it really came down to personal relationships with the team, investors and early customers and not letting anybody down."

3. Solve for your customers

Having been the CTO of multiple startups and the former Chief Product Officer of Hubspot, David has learned some of the best practices of building something that users love.

"For the last three years, I've been really focused on this idea of building customer-driven companies and teams which is to basically make everyone in the company understand that any idea that one of us have is wrong by default. By default, we should expect that all of our ideas are wrong and because they're wrong, we want to get out of the building and understand is it 10% or 100% wrong."

"Everyone in any of our companies has had a tight integration of customers and this idea that we're here to solve problems for our customers and not necessarily for ourselves. So building customer-driven teams has really helped in building these companies."

4. Only pursue an idea if you can't stop thinking about it

Given all the ideas David has pursued, I knew I had to ask him about how he decides what idea to pursue.

"The answer is simple but it's not obvious. For people like me who has ideas every single day, I'm drowning with ideas. The way that I know that an idea is worth pursuing is if you keep coming back to the idea. For me, I have a long list of ideas and it's the idea that I keep going back to that I end up pursuing. It's almost like I have no choice but to do it because I can't get it out of my head."

5. Surround yourself with people who compliment your strengths

Throughout his journey, David has learned that you can never be the best in everything so it's better to find people who can do things better than you.

"As an engineer product type of person, I always thought that the perfect and best product will sell itself and always win. We all know that this is not true but I still have this bias in me. I've made the mistake of not bringing in sales and marketing people early enough. So today, I try to bring in a lot of marketing people into the business as early as possible. They bring you a different perspective, and they give you different feedback. And in most cases, they end up becoming internal customers."

6. Seek out advice from mentors and advisors

David is a big believer in finding mentors and advisors who can really help you avoid making common mistakes.

"One mistake that I see other startups make is that they usually don't bring in advisors for various reasons because they may not want to invest in that area or they're too cheap with their equity. However, I'm a real believer in bringing in a lot of advisors you respect early on to give you fresh perspectives and domain expertise so that no matter how much ego you have, you can be humble enough to listen to them."

"You also want to have mentors because you always have to be learning from people who are five, ten, twenty years ahead of you and learn from the experiences that they're having. These are experiences you're going to have at some point so if you want to hack your learning, why not bring in mentors and advisors who can accelerate your learning."

7. Being a leader is all about serving

The biggest lesson I took away from David was this concept of servant leadership.

"Basically, the idea is to invert the pyramid that usually exists within companies where the CEOs and different VPs at the top and the individual contributor and people in the team are at the bottom so everything flows down and people want to rise within the organization because they want to be a boss or manager. I leaned into this idea of inverting this pyramid so that the higher your title, the lower you are and the more you have to spend time helping the people above you. At the very top of the pyramid are the customers. I want to make your life easier and make sure that you succeed."

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Published on: Feb 16, 2016