Help Me Choose
Jordan Benjamin

By: Jordan Benjamin on January 6th, 2021

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Dan Tyre



Dan Tyre founding team member of HubSpot Employee #6 joining in 2007 and first sales person. Held various positions in sales, management, recruiting, training and more.  He also created the term SMARKETING to help create alignment between sales and marketing.  Dan mentors so many reps aside from asking others to go mentor others and pay it forward.  Check out his best-selling book,Inbound Organization.  Learn from his experience working at 2 person startups to organizations of 45,000 people. 




You’ve had such an interesting career working with so many different people and recently training agency partners at scale on how to sell and grow their businesses. How did you get into sales?


Desperation.  Sold books door to door to work my way through college. Went to Colgate university in 1976 and didn’t have a lot of money, couldn’t go back sophomore year unless he made $5K. Southwestern Corporation, Nashville, TN. 

As long as I can make $5 grand, I’m in! Incredible sales experience.  COMMISSION ONLY! Sent to Bellingham, WA.  95% of people quit. I couldn’t quit because I didn’t have enough money to get back home.  I had to consult with bank Presidents to gas station attendants and it was a fantastic introduction to the sales process. We read Tommy Hopkins and learned consultative selling. I was a slow percolator and it took me a while to get it.  

I was out in the field 2 weeks and I was scared, would fumble through stuff and didn’t have high confidence. 

A lady took me in, gave me a cookie as I stumbled through my sales pitch and said SHE WOULD BUY! Took the $25 and ran to McDonald’s to eat my first meal in a week!


Door to door selling carrying his 2 Dictionaries in a rolling case. 

Building rapport, at the time had to “wait for my husband to come home” DAN → that’s exactly what your neighbor said….Ms Joyce said the same thing, but realized she could spend the $$ because it’s her kids education → now his customers were ready to buy showing proof of sales from their neighbors. 

Last month using that strategy closed 40% of people after everyone knew him and got a deposit from most people! 

First year Individual Contributor $5,000

2nd year 9 guys recruited, got a cut from that , 7 quit, 2 stayed and made $8 grand!

Junior year went to Vegas playing poker

Graduated college in 1980  from Colgate University Played bass in heavy metal rock and roll band 

Being a bass player is a great foundation for being a great business person

1982 tired of making $25/week - 14 computer stores in Boston

Walked in to Computer Store, Roger Lund gave him a shot and Dan became #1 sales person in 3 months because I outworked everybody

Roger left for Startup, wanted to take Dan with him and would pay dan $1,500/year more. Now Dan’s a startup guy!

1983 left for Business Land $3 Million next 9 years grew to $1.4 BILLION 


Dan started as Rep → Sales Manager for 9 months → General Manager → LA ran 6 locations → San Fran training reps → NYC= 35% of corporate revenue

Bible = ART OF SELLING by Tommy Hopkins

“I got addicted to hypergrowth”

Back in the 1980’s and everyone had to buy computers. Talk to accountants and they WOULD CRY seeing how easy it made their life!

The way you sold computers is you would put a sign out and people would come by

Married 31 YEARS! 

Dan all energy and enthusiasm, his wife Amy is the smart one and she was a great seller

After 9 years at Business Land. Started his own company as CEO scaled to $30 Million as a professional services location

Bought training company that went Bankrupt, was AWESOME (learning)! Had to tell employees and their locations and tell people he had no money.  Learned humility at 40 and to always have a contingency plan

4th startup, Groove Networks, bought out by Microsoft, his VP of Sales was Brian Halligan

Got a call when Brian & Dharmesh wanted to start HubSpot because he had great energy and was the best salesperson they met!

Mark Roberge - Sales Acceleration Formula - VP of Sales at HubSpot

Didn’t miss our number for the first 27 months at HubSpot and everything I knew about selling and business changed completely after I joined HubSpot!


“I am by far the luckiest guy in the world, I’ve had dinner with Bob Marley,  taught Steve Tyler how to fire his manager met Muhammed Ali,  and met with  president’s. Things happen to me and it’s because I have a positive Mindset”

“You’re (enter your name here), you can do anything”  It’s my mantra, I say it to 4,000 people in the world! 

Do you have an identical twin? No? Well then YOU ARE THE ONLY YOU OUT THERE!

You can do anything, the key is to figure out what you want to do and WRITE IT DOWN

In 2020 we set goals and work backwards

Mindset- you first need to believe you can do it, then you must know WHAT you want to do

This must be written down

Write out what you want

Succeed: How We Reach Our Goals by Heidi Halverson 

Why Goals?  What Goals?

Written down goals are more effective, people are healthier

Mindset is 99% of Sales

My Prospecting now is usually in front of 100 people down at Stetson University - gotta raise $$ for crew to get a new boat

“I’m Dan Tyre, I can do anything”


“This Guy is Gonna Pickup and make a donation to your crew program!” They think he’s insane for picking up the phone, let alone believing he is going to get the $$!

What kind of donation do you want?  I don’t know, what are you comfortable with? $100! A tremendous and wonderful feeling!

“I look at the phone and say this person is going to pick up and I have some level of skills obviously, but this is MINDSET”

JB: Was there a point where that mindset came about or did you always have it?


What I learned selling books and in my entrepreneurial experience is 99% of success is what we call a Growth Mindset. 

Never had a problem speaking in front of 10 people, even when I was an average speaker I knew I was going to get there, I was Bruce Springsteen early on, because “Nobody outworks Dan Tyre”

All the young people think they can outwork the old man. 

  1. I don’t drink so I’m full of energy
  2. I’ve got the positive mindset while young people are still working on it

When I was growing up, when you turned 60, you died

Now Warren Buffet is 90, so he’s my new model and I have 18 years left, it’s going to be awesome!

Dan Tyre 2.0 = Smart, empathetic, willing to help

My Mantra = Do The Most Good For the Universe

There’s nothing that’s better than having gratitude for where we are


I’m still at HubSpot because I love working with these young people straight out of college

The key is Proper Mindset, define what you want to do

I’m not the smartest, wow there are so many smart people I’ve learned from and been supported by!

How to engage sales people if they need re-engagement 

I’m your confidence before you have confidence

Everyone goes through their twists and turns 

When you eat the big dog, CELEBRATE YOUR SUCCESSES! 

When the big dog eats you, you can’t wallow, you have to do recovery and understand this is a part of anyone's sales life

The Mental Mindset is; I’m at the top of the charts all the time and Nobody is going to outwork me

We’re top 2% because we will outwork everyone 

At a certain place in my life it wasn’t competitive with anyone else and it was being competitive with myself

Growth mindset, you’re always improving.  There are things I can always be doing better and learning

“I’m like a teenage girl, I just talk on the phone everyday”

The great thing 


5 things  Make sure you:

  1. Take Care of the Basics; Eat, Sleep & Exercise
  2. Get a good playlist!
  3. You have to have a Vision Board
  4. SSP = Shameless Self Promotion
  5. Find 3 people  that will tell you 10 great things about yourself when the big dog eats you!

I can be your confidence before you have it. 

Some people are mental giants that can do things that I can’t do. 

My best attribute is I’m stubborn, you can’t beat someone that won’t quit


JB: As you’ve had a chance to train, mentor, coach thousands of sales people over the years.  What is the biggest hurdle you’ve seen?


People don’t understand how important it is.  If you don’t have your mindset ready it’s hard to win. 

You’re gonna stink for 30,60 sometimes 6 months.  Roleplay can accelerate it. But the only way you get good is PRACTICE.

Once slow percolators get it, and they have a good process, the are locked in!

The whole foundation of HubSpot & Inbound Revolution is sales has changed, used to be all about sales people and now it’s all about the customer

Always Be Closing is Dead, How To Always Be Helping

If someone calls you to sell you something, or help you with something. Which one would you like to talk to?


The Riches are in the niches

Back in the old days you could be OK as a generalist, now it’s time to be a specialist

  • Start with a niche
  • Do your research
  • Now you can figure out what they need
  • What’s the 3 things I can help you solve that you’d buy me a breakfast sandwich next time I’m there? If I can help with 3 things, then we’ll do business or I can send them to someone who will help better


You mention empathy, how do people build that?


Women are better at empathy than me.  

Women are better at life than men!

Give $10 to a man, they buy beer and get drunk.  

Give $10 to a woman they buy diapers for the whole village. Women are better listeners

Guys are taught to BS and push through, women are taught to socialize and are better

Empathy builds better alignment. You can be encouraging when you know what they’re trying to accomplish. 

“I don’t care if you buy.  What can I do to help?”

Empathy of understanding what it’s like to be in your prospects shoes. 


It’s harder to be a young adult now. When I was growing up I did so many dopey things and nobody knew about it.  It’s so hard now because everyone is judging and can see everything you’ve done.

“Once you get to be 62 you realize none of this shit matters!”

The only thing that matters is your relationships

“The secret of life is strong relationships” - Warren Buffett

Realize the more you help people, the more gratitude you have for your situation

I made the decision I want to help people because that turns me on

It used to be; have fun, make money and learn stuff. NOW what I want to do is doing that for others!

JB: More women coming into sales is so helpful and so many that helped me


Sales has always paid women similar to men because it would be crazy not to!  There are so many women who are great in sales and HubSpot is working so hard to reflect the demographics of women we sell to.  The folks from HubSpot like Katie Burke and others are doing so much good for the universe. I stole my mantra from my kid, Eli. 

JB: What should someone do as a first time sales manager?



It’s like being a new parent, there are new skills you’ve got to learn. 

You’re working with human beings

Go back to the beginning; learn about recruiting, interviewing, motivation, management, building trust, forecasting,  product, managing up/down and there is a TON of stuff you’ve got to learn. 

Sales management is the most difficult position in the company because sales people are weird.  They are numbers driven, highly emotional and all in their brain. 

In sales I always want HIGH TRUST.  How do I build trust with you? 

What kind of manager do you want me to be? → GO FIGURE IT OUT

One Minute Manager

You don’t have trust in any relationship, you don’t have squat

Got a problem. Do you have good problem definition? What’s your solution? → Go figure it out

New reps MY POTHOLE LIST - 3 things getting in your way?

Secret of life, define what you want to do and then work as hard as you can with the right people.



Dan Tyre

Inbound Organization

Dan on HubSpot Blog


Twitter: @dantyre

Instagram: Dtyre1

One Minute Manager

Always Be Closing is Dead, How To Always Be Helping

How to engage sales people if they need re-engagement 


ART OF SELLING by Tommy Hopkins

About Jordan Benjamin

Jordan is the founder of My Core OS. After spending years in sales, working with sellers and studying peak performance he found an opportunity to help sellers level up to not only build peak performance at work, but to also create harmony between work and life so you can sustain performance over the long term.