Startup Advice from Bolster CEO and Co-Founder Matt Blumberg

by Lauren Becker

On July 22nd, 2021, Bolster Co-Founder and CEO Matt Blumberg joined High Alpha Managing Partner Scott Dorsey to unpack lessons learned throughout his career and key themes from his new book, Startup CXO.

Unlike other business books, Startup CXO is designed to help each functional leader understand how their function scales, what to anticipate as they scale, and what things to avoid. Matt approaches this topic with deep domain expertise in creating startups and scaling them. Before Bolster, Matt was the Founder and CEO of Return Path, which he sold to Validity in 2019.

While we could unpack a lot from this insightful conversation, these are the top three takeaways that I think every software entrepreneur can learn from.

1. There is no instruction manual when you start your first company.

As startups navigate new challenges, it’s key that they don’t just rely on outside resources to grow. Instead, they should also focus their attention inward on their internal operations. 

By regularly reflecting internally, leaders will develop a deep understanding of where they are, where they want to go, and how they can achieve their goals. 

Why? Every startup is different. Each one has different strengths, challenges, talent, and milestones that shape their company along the way. Though there are a handful of books, articles, and videos on entrepreneurship, there is no one way to start a business. 

2.  Startup CEOs should be cross-functional supervisors.

Many CEOs start as domain experts by leading a team in their most knowledgeable function.  The transition to CEO is typically difficult because rather than only focusing on one function, they now have to oversee every function of the business.

Learning all aspects of the business is crucial to better understand the ins and outs of the company. For example, a CEO that doesn’t have a good grasp of the company’s finances can easily miss a cash flow problem that is detrimental to their success. 

This is why Matt likes to think of startup CEOs as cross-functional supervisors because they have to possess a deep knowledge of each function in order to do the best job possible.

“If you don’t know enough about a function, you could wake up and be in terrible shape without seeing it coming.” – Matt Blumberg

3. It’s never too early to add independent thinkers to your board of directors.

When Matt surveyed startups boards, he found that a majority of CEOs only included board members with extensive experience on boards or as a CEO. This method fails to grant them diverse perspectives. 

Instead, Startup CEOs should ask themselves what skills they are missing and what industry experience would be most helpful to them. Once they gather these data points, they can pinpoint who has done this in the past and identify potential independent board members. 

When building out your board of directors, he recommends following the rule of one. 

“The rule of ones”: Each board should have one founder, one member for every investor, and one independent member on the board.

If you missed the event, you can watch the entire conversation with Matt here. Every month, we sit down with leaders and entrepreneurs like Matt and dig into learnings from their backgrounds and careers. You can learn more about the High Alpha Speaker Series here.