Reboot Podcast Episode #54 – Hearts Broken Open: The Case for Conscious Leadership and Entrepreneurship – with Matt Munson

The Reboot podcast showcases the heart and soul, the wins and losses, the ups and downs of startup leadership. On the show, Entrepreneurs, CEO’s, and Startup Leaders discuss with Jerry Colonna the emotional and psychological challenges they face daily as leaders.

Episode 54 // February 3, 2017

A disciple asks the rebbe: “Why does Torah tell us to ‘place these words upon your hearts’? Why does it not tell us to place these holy words in our hearts?” The rebbe answers: “It is because as we are, our hearts are closed, and we cannot place the holy words in our hearts. So we place them on top of our hearts. And there they stay until, one day, the heart breaks and the words fall in.”


Matt Munson

Matt Munson

Co-Founder & Chief Executive Officer at Twenty20

View Bio

Episode Description

Every entrepreneur hears the call of an inner voice. We may call it drive, intuition, or our guiding voice. Regardless of name it pushes us forward. This voice can be our most powerful ally in the pursuit of authentic leadership, or become our greatest enemy when clouded by fear, anxiety, or self-judgment. Most of us equate struggle as a bad or wasted experience. But as we find in this episode, that association is far from the truth. Instead, heartbreak holds our greatest potential to allow true transformation to be possible.

Fresh off an $8M round, Matt Munson led his team at Twenty20, a crowd-sourced commercial photography catalogue, in a radical pivot– changing the business model from B2C to B2B. The business seemed to be moving in the right direction, yet Matt began to feel crippling pressure to achieve more growth. This pressure, perhaps better defined as anxiety, quickly became all consuming, permeating through the entire Twenty20 team. It wasn’t long until the company had reached another tipping point to survive. With the support of his board, Matt made the difficult decision to layoff nearly 80% of his staff and embrace a new path– one centered around simplicity, transparency, and embracing the open-hearted warrior within.

Episode Links:

Matt Munson on Twitter | Twenty20 on Twitter | Twenty20 |   How I burned 10 Million Dollars so you don’t have to | Getting Real

Show Highlights

Top Quotes

The human side to the journey has been tough. – @mattmuns

This is my first time running a venture backed company where the pressure for growth becomes kind of an all-consuming thing. – @mattmuns

The expectations on ourselves of these folks really took a big bet on us. – @mattmuns

I’ve carried a burden of a need to do big things. – @mattmuns

The voice that has always said you better do great things or else, you are nothing. – @jerrycolonna

I’m either great and living up to my potential or I’m a piece of shit. – @jerrycolonna

The true strength of a leader has both a strong back of a warrior and the open heart. – @jerrycolonna

A really successful leader embodies a whole bunch of things that may seem to be in conflict. – @jerrycolonna

Companies are hard to rebuild mid-flight. – @mattmuns

Profitable businesses create optionality for themselves. – @jerrycolonna

It’s been really powerful return to different team size and gets to rebuild with the lessons learned. – @mattmuns

I spent the first couple of years running this business feeling like I had to show up for board meetings with the answers to the problems. – @mattmuns

Maybe we can redefine a little bit the definition of success. – @mattmuns

Leaders are not born in easy times. – @jerrycolonna

Key Takeaways

Matt Munson is a co-founder and the CEO of Twenty20, a marketplace for authentic stock photography.

Twenty20 recently made a strategic decision and a personal decision to open up the company’s inner story and share it publicly hopefully for the greater good.

Prior to the recording Matt published a piece on Medium called I Burned 10 Million Dollars So You Don’t Have To. It is the story of how Twenty20 raised over $8M in capital in 2014 and then spent that capital without reaching profitability/sustainability.

The original impetus to raise the money was that despite some success, the company had been unable to reach profitability. They decided that to move forward would require drastic measures, changing the business plan from a B2C model to a B2B model. The team raised the capital on the precipice of this pivot.