Why Successful Serial Founders Choose to Build with Venture Studios

Dianna Lesage
8 min readMar 18, 2022

Matt Blumberg is the kind of person you want to talk to all day.

Easy-going, thoughtful, experienced, and engaging- I can see why his company, Return Path, was consistently named as “Best Place To Work” and placed #2 on Fortune’s “Best Companies to Work For” list. Matt is a true leader who understands the value of human connection and helping people achieve their greatness. His latest venture, Bolster, is on a mission to do just that for CEOs and executives.

Recently, I had the opportunity to talk with Matt about why serial entrepreneurs are choosing to build their next startups with Venture Studios.

I wanted to understand how these founders evaluate their options and, instead of doing it on their own or going the traditional VC route, decide to partner with a Studio. What compels them? What is the experience like? What are the challenges and what major lessons should be shared?

To set the stage for this conversation, you have to understand that Matt is one of those unicorn founders that could have done anything. Prior to founding Return Path- a venture-backed email marketing company doing $100M+ in revenue when sold in 2019- Matt managed the Internet division of MovieFone, Inc. until AOL acquired it, and before that he worked in venture capital and consulting. He literally wrote the book on successfully scaling startups. He’s been building winning internet companies since 1999.

All of this is to establish- without a shred of doubt- that Matt Blumberg could have built Bolster without a Venture Studio. He could have bootstrapped or easily gotten venture backing- but he chose to work with High Alpha, a B2B-SaaS-focused Studio that pioneered the Venture Studio model and is one of the most established in the industry.

Now What?

It all started with the exit of Return Path. The acquiring company, Validity, didn’t really need Matt and his executive team to run the venture- they were free to take on their next challenges.



Dianna Lesage

Venture Studio expert. Creator capitalist. Lover of innovation.