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.

Guests

Matt Blumberg

Matt Blumberg

Founder and CEO of Bolster

View Bio

Matt Blumberg

Matt Blumberg

Founder and CEO of Bolster

Matt Blumberg is the founder and CEO of Bolster, a marketplace for on-demand executive and board talent launched in 2020. Matt was Chairman & CEO of Return Path, Inc., the company he founded in 1999, until its sale to Validity in 2019. Return Path was the market leader in email optimization, helping thousands of businesses use the email channel more effectively to promote and protect their brands and winning numerous employer of choice awards including #2 on Fortune Magazine’s “Best Companies to Work for” list. Prior to founding Return Path, Matt was founder and General Manager of the Internet division of MovieFone, Inc. (777-FILM) until the company’s acquisition by AOL, and had previously worked in venture capital and management consulting.

In addition to his corporate entrepreneurial work, Matt is co-founder and Chairman of Path Forward, a nonprofit that was spun out of Return Path in 2016, whose mission is to empower women to restart their careers after time spent focused on caregiving, working with more than 75 companies including Apple, Amazon, Wal-Mart, Intuit, Campbell’s Soup, PayPal, Verizon, and Oracle. He is also the author of 3 books: Startup CEO: A field guide to scaling up your business (based on his popular blog on entrepreneurship, StartupCEO.com), Startup CXO: A field guide to scaling up your company’s critical functions and teams, and the forthcoming Startup Boards, all published by Wiley & Sons.

Matt has been recognized as one of New York’s 100 most influential technology leaders by Business Insider, by Crain’s as one of New York’s Top Entrepreneurs, and by Ernst & Young as an Entrepreneur of the Year finalist. He has served as a Board Member of numerous corporate, nonprofit, and community organizations, as well as Chairman of the Board of the Direct Marketing Association, and he completed a brief assignment as founder and leader of the State of Colorado’s COVID-19 Innovation Response Team in 2020. Matt attended Princeton University where he graduated Summa Cum Laude with an A.B. in Urban Planning in 1992. He lives with his wife Mariquita and his three children, Casey, Wilson, and Elyse in Scarsdale, NY.

Find Matt on:

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.

View Transcript

Podcast Topics

Join the Conversation.

We believe that in our work lies the possibility of the full realization of human potential.
Work doesn't have to destroy us. Work can be the way we achieve our fullest selves.