Matt is a founder and CEO of Bolster, a new talent marketplace for on-demand executives launched in 2020. Before Bolster, he was the CEO of Return Path. 

Matt wrote Startup CEO: A Field Guide to Scaling Up Your Business (Wiley, 2013), a book dedicated to helping entrepreneurs navigate the transition to executive leadership. He also blogs about his experiences as a first-time CEO at Only Once.

In this episode, Matt will take us through his entrepreneurship journey. He will give us in-depth details on how they founded Return-path, how they built the company culture, and their exit from the company. Also, he will tell us how he creates a support system, his journey to learning to say, “no” and how he became a second-time CEO.

Key Talking Points of the Episode:

[01:36] Getting to know Matt

[03:27] Matt’s growth path in leadership

[09:30] How Matt learned to say NO

[12:39] How to build a support system

[13:23] What’s the difference between a coach and a mentor?

[15:10] How Matt handles difficult conversations with his employees

[21:20] Coaching someone is about to get fired

[29:30] How Matt built the company culture at Return Path and how it evolved

[40:16] How Matt deals with difficult setbacks and bad moments in his day-to-day life

[41:57] Transparency and authenticity

[43:27] Matt’s favorite failure

[51:05] How Matt sold Return Path

[56:25] What is it like to be a second-time CEO for Matt?

[01:02:58] The most challenging role for Matt in his current role

[01:04:42] Matt’s book, Startup CXO and why it is important 

[01:10:43] What Matt wishes he knew earlier on his journey

[01:11:15] Matt’s message to other founders, as they embark on their journey to grow into leaders

Quotes from the Episode:

“You’re never done growing as a leader all of us are works in progress.”

“The most important conversation to have with an employee or an executive who is not doing well is the conversation you have before the one you fire them.”

“The best way to deal with a bad moment is to wait a few minutes. Something else is going to come along and replace it.”

“When you make the hard conversation early, that means the later conversation is easier.”

“Don’t be shy about asking for help. There are a lot of people around you who know a lot more than you do about a lot of things that you’re doing.”

Learn more from Matt:

Startup CEO: https://www.amazon.com/Startup-CEO-Website-Scaling-Business/dp/1118548361

Startup CXO: https://www.amazon.com/Startup-CXO-Companys-Functions-Techstars/dp/1119772575