You Gotta Hustle

A Slice on Dan Tyre, Angel Investor and Sales Director at Hubspot

Did you know that lions only succeed 25% of the time when hunting? This was one of the first questions Dan Tyre asked me. After I shook my head “no”, he proceeded to ask me a few more lion-based facts and threw in some anecdotal parallels between lions and life in general. If lions (the kings of the jungle) only succeed 25% of the time, what does that mean for us?

This fully stumped me, but turned out to be a bit of a foreshadowing into the rest of our conversation regarding success, and what it takes to get there. Having founded five startups in 40 years, he has experienced many notable successes and a few notable failures (i.e bankruptcy).

The first startup grew to a $1.5 billion IPO, the second one (co-founded by Tyre and where he served as CEO) grew to $30 million before it was sold, and the third one went bankrupt. Tyre went on to describe how he survived the bankruptcy emotionally. “It was so hard, my beautiful wife had to walk me through it. I was throwing up all the time and had emotional problems.” Even when faced with an obviously grim outlook, Tyre said he realized that once you go through an experience that difficult, you come out the other side saying “well, that wasn’t so bad”. No one threatened to punch him throughout the ordeal, which he was stated he was very grateful for. Having done it “all wrong” in that company it’s his mission now to help others avoid his mistakes.

The next phase of Tyre’s life began when he got a phone call from Brian Halligan and Dharmesh Shah in 2007, the co-founders of HubSpot. They asked him to be the first salesperson on their team. This was back when SaaS was just starting out, and HubSpot was working to be different from their competition. Tyre relayed that oftentimes in meetings they would look at what competitors were doing, and actively chose to do the opposite. At the time of his hire, he was the only employee out of the initial 10 that didn’t hold an MBA from MIT. This was a bit intimidating to Tyre, but he went on to add that he believes there are a few characteristics that make a great salesman, and coincidentally the same things he looks for when hiring.

1. Be Smart. This doesn’t have to be in the traditional book smart way, it could also mean street smart.
2. Have a Natural Curiosity. Someone who asks “why”, someone naturally curious, and who wants to truly understand people.
3. Take Personal Responsibility. Take responsibility for your own success, have a sense of ownership in the company and in the work. “You gotta hustle.”
4. Coachability. Be able to think on the fly, and innovate on a dime.
5. Optimism. No one wants to work with a Debbie Downer.

HubSpot present day now employs 4,500 people and has 3,500 companies using the platform.
Tyre explained that he feels everything that happens in the startup scene is all in a person’s brain. “You’re never as good as you think you are, you’re never as bad as you think you are. That’s why co-founders are better than individual founders, according to the statistics, because it’s a mental game. The most important thing is to keep going, even when it sucks because sometimes it’s gonna suck.”

A final piece of knowledge Tyre shared came from Laurie Norrington, a HubSpot board member and “brilliant” inventor of the Norrington Decision Matrix. The Matrix consists of four quadrants: A type of decision (easy or hard) and how easy or hard it would be to reverse or “roll back” that decision.

Of the four, Norrington believed that only one of these is really the type of decision you should spend time on, and that’s Quadrant 4. The hard decisions to make, which also are the hardest decisions to roll back.

In the vein of hard decisions, Tyre told me that “for an entrepreneur, if you get 52% of your decisions right it’s awesome. If you make a mistake, you’re not wrong, you just say, ‘I’m not going to do that again.’ The reason why I’m a successful entrepreneur is because I screwed up so many times (that bankruptcy, are you kidding me!) but after you get through it, you’re like, that wasn’t that hard.”

In closing, Tyre stressed there are three things he tells everybody: have a plan, always be branded (he was wearing a HubSpot t-shirt) and you gotta hustle. To add to the third point, he explained how as an angel investor he sees the same pitch 40 times, and according to HubSpot statistics the average company in 2014 had 6 competitors. Today, that number has quadrupled times 10 to be 44 competitors per company! So, in the words of Dan, always be hustling and get to work.

Founder Bio

Dan Tyre has a background in sales and entrepreneurship. He joined the HubSpot team early on as its first salesperson and is now the company’s Sales Director. Outside of his sales role, Tyre is an Angel Investor and Motivational Speaker. Connect with Tyre on LinkedIn.

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