Reboot Podcast Episode #153 – Everyone Is Scalable – with Matt Blumberg

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.


Matt Blumberg

Matt Blumberg

Founder and CEO of Bolster

View Bio

Episode Description

For our first episode of 2022, Jerry sits down with Matt Blumberg, founder and CEO of Bolster, a marketplace for on-demand executive and board talent. In this conversation, Matt describes how the knowledge and insight he gained during his 20 year run as the founder and CEO at Return Path, Inc. prepared him for the uncertainty that comes with being a second-time founder. The pair discuss Matt’s latest book, Startup CXO, which serves as a handbook for defining the functional competencies and skills needed in various roles within an organization, and explore what companies can do to support their employees in scaling to meet the needs of the business.

Show Highlights

Top Quotes:

“I had kind of felt like I had really built a pretty solid skill set in managing a midsize organization, which is totally different skill set than a startup.” – Matt Blumberg

“Startups fundamentally need three things: they need a good idea, they need money, and they need the right people to bring that idea to life.” – Matt Blumberg

“No one teaches you how to be a CEO unless you are working at a giant company and you’re being groomed for it for 20 years.” – Matt Blumberg

“I think good advice for a first-time founder is, you might love the next one [company] even more.” – Matt Blumberg

“Is the company doing well? Is it having an impact? Is it vibrant? Are employees engaged? Is it solving customers’ problems? Are shareholders happy? Those are a really different set of questions from, am I as the founder thriving?” – Matt Blumberg

“I have a set of questions that I ask myself every year, which is: am I learning and growing still in year 5, 10, 15, 20? Am I having fun? Am I having an impact? And am I making enough money?” – Matt Blumberg

“Scaling a business has a lot of operational challenges. I always refer to it as the art of the teardown. All of a sudden all the systems and processes that have been in place for the last two years don’t work anymore and you gotta tear them down and it’s kind of a bummer ’cause you were the one that built them.” – Matt Blumberg

“What we’re trying to build at Bolster is an agile way of scaling your leadership team and an agile way of scaling your board. And that means it matches the tempo and the needs of a startup, which are quick, which are fluid, which are not necessarily the same thing in every seat all the time.” – Matt Blumberg

“Mentors are a great way of bringing expertise and talent into an organization without hiring people.” – Matt Blumberg

“One of the things I learned over the last 25 years is that everyone can scale further than you think. They may not scale infinitely, but everyone can scale further than you think if they’re intentional about it.” – Matt Blumberg

Leave us a review on Itunes! Follow our step by step guides:

How To: Leave a Review on Your Computer

How To: Leave a Review on Your iPhone

Never miss an episode! Sign up for our newsletter to stay up to date on all our episode releases.