[Podcast]: How To Remove Ego, Find Your True Motivation And Win As A Team

He left Microsoft to start a business with 3 of his friends.

Two years into launching, they knew something was wrong.  They were pushing incredibly hard, but customers just weren’t interested in the product.

They decided to pivot.

With 1 month left of cash, the team realized they needed at least 2 months of coding to fix a bug in their product.  

They hustled their way to an angel investor and the rest is history.

That’s the (quick) story of Manny Medina and Outreach.io, currently valued at $500M+

Before Outreach.io, Manny led sales efforts at Microsoft and was the #4 employee at Amazon Web Services.  He also has an MBA from Harvard Business School and MS in Computer Science from the University of Pennsylvania.

I absolutely LOVED talking to Manny about being an entrepreneur, leadership and sales.

Here are 5 things I learned from my conversation with Manny:

A Lesson From Jeff Bezos

When Manny was at Amazon, Bezos had a mantra: “strategically patient, tactically impatient.”  This is very similar to Gary Vaynerchuk’s motto of micro-speed, macro-patience.

It’s about going all-out every single day, but having the patience to realize that great things take time.  Apply this to business.  Apply this to life. 

Four Levels of Motivation

I asked Manny what pushed him on the days when he wasn’t “feeling it” or if he was going through a rough patch.  He said that there are four sequential steps of motivation that you can have: fear, greed, duty & love.

Love is the goal.  Love for your customers, for your employees, for the product, for the fact that you’re making a difference in the world. That’s what Manny feels and it’s a major reason for Outreach’s success.


Manny places a huge emphasis on teamwork.  That’s probably why he fist bumps every employee in the office every morning (yes, you read that right).  

To most CEOs, that would seem like a time suck. But for Manny, it’s part of building a culture that focuses on team wins and a great camaraderie.


Manny says that the best sales reps (and entrepreneurs) can erase the scoreboard.  After each month, quarter and year, the focus needs to be on what’s next. Nobody cares if you hit quota last year.  What matters is now. He says “winning makes you sloppy” and that complacency is a killer.

“Winning makes you sloppy.”

What Is Selling?

“Selling is educating, empathizing, experimentation and adding value.”  Couldn’t have said it better myself.

Listen Here:

Google Play

Connect with Manny:

Manny’s LinkedIn
Manny’s Twitter

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