Startup CEO

Founder's Bookshelf / Book

Startup CEO

A Field Guide to Scaling Up Your Business

Book by Matt Blumberg

Blumberg, who ran Return Path for 20 years from founding through sale, wrote a reference manual covering every aspect of the CEO job at a startup: board management, executive hiring, culture building, fundraising, M&A, and managing your own psychology.

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About Startup CEO

Startup CEO is organized as a reference manual rather than a narrative. Blumberg covers the CEO role in sections: storytelling (vision, pitch, company narrative), building the team (hiring executives, managing the board, developing culture), running the company (meetings, decision-making, strategy, communication), and managing yourself (time management, self-awareness, dealing with stress and loneliness).

The book benefits from Blumberg’s 20-year tenure at Return Path, an email deliverability company he ran from founding in 1999 through its sale in 2019. Two decades at one company gave him an unusually long perspective on how the CEO role changes as a company grows. The problems of a 10-person startup are different from the problems of a 50-person company, which are different from the problems of a 300-person company. Blumberg covers all three stages.

The sections on board management are particularly useful. Most first-time CEOs have no idea how to run a board meeting, manage board expectations, or handle the relationship with investors who have a different timeline than the founder. Blumberg covers these topics with the specificity of someone who ran hundreds of board meetings.

The writing is practical and structured. Each section has clear takeaways. Blumberg is not a flashy writer, but he is thorough. The book includes contributions from other CEOs, board members, and executives who add perspectives Blumberg could not provide from his own experience alone.

For first-time founders who have raised capital and are scaling, this is one of the most complete guides to the CEO role available. It addresses questions that most founder books ignore: how to fire an executive you hired, how to handle a board member who disagrees with your strategy, how to maintain your own mental health when the company depends on you.

The second edition (2020) is updated with new material. At about 430 pages, the book is long. It works best as a reference you consult when facing specific situations rather than a book you read cover to cover.