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Most who live in the startup world have a very intimate relationship with failure. The overwhelming majority of startups are forced to shut their doors before they accomplish their goals. This is the law of the land, and it is part of why working at a startup can be especially exciting and intense.

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Seattle startup veteran Dan Shapiro, currently the founder and CEO of 3D laser-printing company Glowforge, has experienced the ups and downs of the startup world first-hand. He has founded and led four successful startups, and he shows no sign of slowing down.

With his new book, “Hot Seat: The Startup CEO Guidebook,” Shapiro has synthesized his many years of experience as founder-CEO of startups Ontela, Sparkbuy, RobotTurtles, and Glowforge into a cohesive, practically-oriented, and insightful guide to the startup world. “Hot Seat” is pragmatic but not cynical, and empathetic without condescension. Shapiro’s desire for his readers to avoid his mistakes and learn from his successes permeates the book and seems wholly genuine.

Dan Shapiro, if this article reaches you, let me assure you: If ever I need to incorporate, I promise to do so in Delaware.

Hot Seat is divided into five sections, each discussing one stage of a company’s life. The first segment, Founding, is filled with the assorted do’s and dont’s of starting a company. As he should, Shapiro draws repeatedly on his personal experience. Among many other topics, Shapiro talks about the process behind his decision to found and run RobotTurtles on his own, and concludes the first section by telling the reader the inside scoop on his only startup ever to fail (you’ll have to read the book for more details on this!).

Shapiro goes on to discuss all things money in his second section, Finance. He goes over the different ways that eager entrepreneurs botch their investor pitches, pivots to a detailed discussion of angel investors and venture capitalists, and has the variety of experience to go into detail about the crowdfunding strategies he used to make RobotTurtles the (as of then) most backed board game in Kickstarter history.

Dan Shapiro himself.
Dan Shapiro

Shapiro astutely realizes that the best Kickstarter campaigns aren’t the ones that simply market a cool, new gizmo; there’s more to it than that. Rather, the Kickstarter products that really end up being winners are the ones that make the backers feel like they are helping to bring something special and important into the world, in addition to being just plain awesome. Shapiro articulates this as “80% preorder, 20% community and altruism.”

Shapiro’s third section, Leadership, starts off with a concise explanation of “The Six Things You Cannot Delegate.” Shapiro gave a talk on this material in 2014. Any CEO who can successfully execute these six broad tasks (which include things such as managing the investors, setting company culture, and owning critical relationships), is doing a lot of things right.

But my favorite chapter of Hot Seat is “Contrarian Segmentation.” Contrarian segmentation is when a startup deliberately decides to go against the grain to avoid competition, and gain more control in a less crowded market. Shapiro tells the story of Chris Zacharias, founder of Imgix.com. Zacharias graduated from Y Combinator in 2011, and deliberately chose to accept millions of dollars less in funding than his fellow Y Combinator peers to coax out the untapped pool of investors hesitant to bet too big. Shapiro quotes a blog post from Zacharias himself:

“The results were amazing. We had verbal commitments for half of the round within three days and the rest of the round was closed out over a 45-minute conversation at a coffee shop in Lower Manhattan … While I had expect to be spending weeks or months trying to fundraise, the whole process was basically over before I knew it and I was back in my seat coding.”

All in all, I enjoyed Dan Shapiro’s book, I got a lot out of it, and I would recommend it to anyone who needs to navigate this crazy startup world. “Hot Seat: The Startup CEO Guidebook,” published by O’Reilly Media, is available in Kindle and paperback.

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