Startup CEO: A Field Guide to Scaling Up Your Business Kindle Edition

I am the CEO of a startup; I've been doing it for a few months and have a dozen employees. Before that I was a Director of software development at a company that successfully IPOed; I lead a distributed team of about 50 developers and was regularly involved in strategy and leadership discussions for my product family.

This is just to give you some context when I—like another, earlier reviewer—say I found this overly basic without much that was useful for me. I understand that many startup founders have no substantial management or leadership experience when they get started and perhaps the book is more useful for them.

Why do I say it was too basic?

Take the chapter on hiring, "Fielding a Great Team". If you've done any hiring before the advice it gives won't blow your mind: pay attention to cultural fit, find outstanding specialists, complement your weaknesses, don't get suckered in by resumes, let your team have input, on-boarding new hires is important.

There are sections on running a productive offsite, on having skip-level meetings, on weekly 1-1s, on how to run a great meeting (have an agenda, start & stop on time, have clear next steps at the end), on OKRs, on terminating employees, on managing remote employees, on how to handle promotions, and more.

The advice given isn't bad at all but it is all things that I think most people with previous non-startup leadership experience will already know. If you've lead a team of 50 then chances are you've had remote employees, you've been to many offsites, you've had to fire underperformers, etc.

What I would like to see improved or changed to bring more value? Startups change rapidly so the structures and processes you put in place this month may not be the rights ones in three months. What do those changes look like? What does the timeline look like for various things? What is it like when you go from having 1-1s with everyone in the company (because there are only 6 of you) to have having your first level of management? What is it like as your "executive committee" evolves and goes from you and and your co-founder to (eventually) 20 people from a variety of functions.

In the section on CEO communication it says, "hire a head of communications you can trust". Okay, but should I do that when I have 10 employees, 50, 100, or 500? What should their team look like? Return Path (the author's company) has around 500 staff and a "Senior Director of Global Corporate Communications". The title of director means they have managers reporting to them. Assume a span of control of 5—the director has 5 reports, each manager has 5 reports—so does that means a team of 25 in corporate communication for Return Path's 500 employees? How does that team grow over time? How do their roles and responsibilities change over the years as the company grows?

I would have also liked to have seen more guidance or rules of thumb—based on the author's experience—for the hard decisions leaders need to make. In the section on growth vs. profit he says, "you should be investing money in growth only if you are reasonably confident the investments you make will pay off". Is there anyone who doesn't believe that when they make those investments? The problems are that people delude themselves or look at partial evidence or misread the evidence. How does someone become "reasonably confident"?

Random note: probably the weirdest passage in the book is the section on "how to impress your boss" that closes by saying, "you will get a raise and a promotion sooner than your friends". Isn't this book for the CEO? Who is going to give them a promotion? Who is going to give them a raise?

All in all, if you're an experienced leader you probably won't find enough meat here to satisfy you.

I could not put the book down, the last week I was suppose to be on vacation but I was itching to get back to work (I know I know it is bad behavior, but the book was really that exciting) obviously I felt like Matt was talking to me throughout the book. I could relate to everything. A wonderful read for every startup founder, first time CEO or even all leaders, Matt shows how to organize and execute around priorities, how to define priorities as a CEO. I have read my share of getting organized, leadership and startup books. But this was so in tune to what I am personally going through it was uncanny, thank you Brad Feld for connecting the dots :) I would recommend it to everyone. Great book Matt! it is going to a become a classic.

Bala
CEO, GreenQloud

Often, the art and science of how to be the CEO of a startup gets overlooked in the rush and haste to working day-to-day, dealing with all the fires and challenges. Startup CEO details the HOW of being the CEO. It's an important guide in approaching the CEO role in a strategic manner. Matt is not telling you what to do. This isn't a book about checklists, but he's giving very helpful insight in how to think about the job of being CEO -- the best kind of startup advice. This is learning how to fish, not being given a fish.

The book is well laid out, from starting the company to dealing with the surprise issues that come up and the unexpected priority changes as a company grows (believe me, there are many). Matt's been a startup CEO for a long time (since 1999) and survived 2 recessions and many changes to his company. His approach is solid yet at times unconventional, but all stem from his real life experiences and looking at problem-solving in his company through a fresh perspective, leaving no conventional wisdom unchecked.

Even if you are not a CEO in a startup, I would recommend reading this book. You might want to be one someday.

Matt's a veteran entrepreneur and his book is a gift to CEO's everywhere. Many management books only focus on big company leadership issues. Many entrepreneurship books focus only on very early stage startups. Startup CEO walks you through the entire growth lifecycle of running a business. Plus, it's organized in easily digestible, standalone chapters that contain concise and actionable perspective and recommendations. If you're leading a company, this is a book worth making time for.