The Start-Up CEO Field Guide - with Matthew Blumberg, Founder and CEO Bolster

Matthew Blumberg, author of the Start-Up CEO Field Guide and founder of Bolster provides his insights and highlights from his series of books for start-up executives. Our host, Ray Rike, and Matthew discuss many of the main topics in the Start-Up CEO and directly from Matthew's experience as a multiple-time founder and CEO including:

• Lessons from being the founder & CEO at the same company for ~ 20 years
• Importance of Authentic Leadership in Changing Times
• Moving beyond Storytelling to Execution to Selling your company

Each book in the "Start-Up" series was written specifically to help founders and CEOs use each book as a guide along their journey as a founder and as a CEO.

What are the unique experiences gained from founding and running the company for almost 20 years? Learning how to pace yourself for the long term is key. Moreover, if you want an organization that is engaged and vibrant it starts with YOU...keeping yourself engaged and vibrant is served well by viewing each day, month, and year as a new opportunity to learn grow, and evolve as a leader. This is especially important as each stage of growth requires a different skill set than what got you there.

One of the challenges of leading a company for an extended period is keeping those employees who have also been around for a long time to keep them fresh and get good at rotating people into different departments. One of the advantages of this approach is that they already have tribal knowledge and share the company's values.

The Start-Up CEO is broken into six sections, and one is "Managing yourself so you can manage others". Why was this an important topic to Matthew? One was his journey to learning how to receive feedback gracefully, which is hard for everyone, and took Matthew a while to become good at receiving feedback. One of the key lessons Matthew learned was the need to "act upon" the input to make sure the person sharing the feedback is assured it was heard and accepted.

Another learning was that Matthew's orientation to "think by talking" and "manage by walking around" could be a double-edged sword. Sometimes employees will take a conversation that the CEO thinks is an idea vetting opportunity that can be viewed as a "decision" versus "discussion", especially with people lower in the organization.

Another example of needing to be careful of your natural orientation is being a "pacesetter", who is more focused on getting stuff done versus building long-term relationship capital.

Why did Matt write a second edition of the "Start-Up CEO"? It was because he had recently sold Return Path, and he wanted to finish the book including his company being sold, and he also wanted to capture many of the social learnings from leading a company during COVID and the resultant change in the workforce that evolved during the remote work era.

One of the final topics Matthew and Ray discussed was the value of collecting data from both internal resources and external sources, especially customers. Matthew highlighted his use of "active eavesdropping" to hear how employees communicated the company messaging to prospects and customers, and also hear what customers were saying to the rank and file that may not be shared with the CEO.

If you are a first-time CEO or preparing for the next phase of growth in leading your company, this episode and conversation is a great listen!

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