Why Successful Serial Founders Choose to Build with Venture Studios

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.

The problem?

Matt didn’t know what that next challenge was.

He knew he wanted to work with his beloved Return Path team and had some ideas for new startups but, to use his words, “ I really didn’t want to start from scratch. I couldn’t imagine sitting across the table from an engineer for two years hoping something works. I didn’t want to go back there.”

And he’s not alone. This is a common sentiment I hear from experienced and repeat founders. They’ve eaten their Ramen noodles and done the things that don’t scale. At this point in their entrepreneurial journey, they want to step up to bat and take a big swing- but they don’t want to start from scratch.

Together with his band of brilliant co-founders Jack Sinclair, Shawn Nussbaum, Cathy Hawley, Ken Takahashi, Nick Badgett, Jen Goldman, and Andrea Ponchione- to name a few- Matt began workshopping potential ideas and running them by investors that backed him on Return Path to gauge interest. Unsurprisingly, many of them wanted to work with him again.

Venture Studio?

As Matt was kicking around ideas, he reached out to an old friend.

Scott Dorsey, now Managing Partner of High Alpha, had been building his breakout venture, ExactTarget, at the same time Matt was building Return Path. They were each other's biggest strategic partners back then and have remained friends over the years.

“ I really didn’t want to start from scratch. I couldn’t imagine sitting across the table from an engineer for two years hoping something works. I didn’t want to go back there.”

— Matt Blumberg

Outside of his connection to Scott, Matt noted he liked High Alpha’s tight focus on B2B SaaS and thinks they do a great job at blending studio services and capital. They also have strong strategic partnerships through their corporate studio arm, High Alpha Innovation.

This is exactly why choosing a focus matters so much. As a Venture Studio advisor, the most important foundational element I help emerging Studios nail down is their thesis. For someone like Matt, who could have worked with any Studio, the fact that High Alpha had a tight focus on B2B and had developed many relevant corporate partnerships, was an important decision-making factor.

Originally, Matt and his team planned to pitch High Alpha Capital- the arm of High Alpha that controls the venture fund. But, the pitch meeting didn’t go exactly as expected (do they ever?) — just as Matt was wrapping up his presentation, the High Alpha team asked him if they could pitch something.

Yes. Venture Studio.

As it turned out, the High Alpha Innovation team had been working on an idea with Silicon Valley Bank as a partner. They were looking for an experienced founder and A-level team to run the venture and the idea just happened to be a lot like Matt’s. Great minds… good fit.

Together, the teams evaluated the opportunity and ultimately decided that some parts from both ideas + SVB as a corporate partner and first customer + Studio services + capital = an unbeatable combination. The teams finalized the deal and got to work.

Needless to say, they were spot on and the resulting company, Bolster, has been incredibly successful.

Speed; Support; Networks

Diving deeper with Matt, I wanted to understand the elements that influenced his ultimate decision to work with a Venture Studio.

In doing so, I learned that there were 3 key factors.

Side note: these 3 factors translate, almost directly, to an article I published recently about the most valuable resources Studios have to offer.

#1 Network

High Alpha came to the table with the perfect partner. If Matt could have drafted a wish list for the ideal corporate partner, it would have been SVB. This factor accounted for major influence in his decision.

“They already had the perfect partner and came with way more formation capital than a studio usually does. I don’t know that I would have done a studio deal without that.”

— Matt Blumberg

This point about network and your Studio’s capability to connect portfolios with customers is not to be taken lightly- this is what experienced founders are looking for and need above almost anything else.

#2 Speed

Studios build startups faster. This simple fact is incredibly enticing to experienced founders who want to hit the ground running. Speed isn’t just about playbooks that help with GTM, it’s about taking tasks and activities off the founder’s plate so he/ she/ they can focus on building the company.

“The Studio came with a bunch of support on the key back office functions like running payroll, shared medical benefits and more. These are things that I could have done and put in place, but didn’t want to.”

— Matt Blumberg

In addition to back office, accelerating the early-stage process also means helping to fundraise quickly. During this stage, all the founder’s attention is diverted from building the actual startup and it’s a mentally exhausting process for founders who have to be in “pitch/ sales” mode 24/7.

Studios are in a good position to speed up this process through their access to investors and perhaps even make it a non-issue by putting in the first round of funding as High Alpha did with Bolster. Instead of spending valuable time fundraising, Matt and his team were able to focus on execution from day 1.

#3 Support & Services

When I asked Matt about the studio services he used in the development of Bolster, he pointed out that he was in a unique position. He came to the table with a full team from his previous venture. For first-time founders, this won’t be the case and studio services will be heavier handed, but for serial entrepreneurs, this is often likely to be the case.

As a studio, you have to understand where your value lies in helping these experienced founders with the things they need and be sure to avoid pushing other offers on them.

As a founder, you really want to do your research and know the strengths of the studio you’re considering working with- what are they world-class at and how can they fill the gaps on your team?

“High Alpha is great at a ton of things, but some of these we never used- like recruitment and product development. What we did need help with was branding and identity which High Alpha is phenomenal at. That was super valuable.” — Matt Blumberg

Onward & Upward

Bolster was launched in 2020 with a $6M seed round and the growing team just raised their $11M Series-B this year (2022).

In their first year of operation, they ran 500 searches for startups and placed 150 people in startups. Their growth is exponential and they’re not slowing down. In just 18 months, they’ve organically scaled to 1000 founders and 7000 executives across every functional area from Heads of Sales, to CHRO, to Product, Tech, and Operations.

Last month they announced the launch of Bolster Prime- a program tailored to founders coming out of an accelerator or studio who need a subscription to mentorship, access to the talent database, and curriculum for how to scale. Esteemed former COO of Techstars, Jenny Lawton, is leading the innovative platform and pioneering new forward-thinking models as she always does. For example, rather than subscribing to the traditional route, Bolster Prime is allowing early-stage founders, who are often on a tight budget, to pay with a mix of cash and equity.

The company also recently launched a venture fund to invest in a subset of Bolster Prime clients.

“When we know that a founder is coachable and we’ve helped to de-risk the organization, we want the opportunity to invest in them.” — Matt Blumberg

Matt is an awesome human being, an exceptional CEO, and his dedicated passion for solving challenges for founders is inspiring. High Alpha Innovation supported his team in this mission and continues to be a leader in the Venture Studio ecosystem.

Through hard work, passion, great leadership, talent, network, and speed, this partnership has been an incredible success and I encourage experienced founders to explore the Venture Studio route as they think about what’s next.

For weekly insights, news, and articles like this, subscribe to the Startup Studio newsletter- stay up to date on everything in the Studio sphere!