During the Dot.com bust and Great Recession, David Dioli was driving business at Ernst & Young and the New York Stock Exchange while his brother, Morgan, was at Georgetown’s Graduate School of Business, running the global financial model for Mercury Interactive and rolling the dice with startup, Sage Systems.

High flying exits make the headlines in Silicon Valley as do unicorns falling from lofty heights. What about the thousands of other companies? What happens to them?

More than 25 years of working with businesses — from software and eSports to equipment rental, auto upholstery, and wastewater disposal — have provided a litany of lessons learned. Board meetings, sales kickoffs, planning sessions, and break room conversations added valuable insights. One could say the Diolis are a seemingly endless databank of know-how and perspective.

That’s the backdrop of the newly released eBook, “Never Startup Alone,” penned by the Dioli Bros., who grew up in Daly City, just south of San Francisco. The 182-pager, sold on Amazon.com, identifies warning signs and red flags that often ground a business before launch.

“The overriding theme is failure,” says Morgan, who became a financial modeling wizard before ascending to finance leadership roles. “We tell the reader where the pitfalls are and what they need to do. We also tell the reader to embrace failure as an outcome.”

The introduction centers on the life cycle of a business — from ideas and leadership to funding and exits. “Mind the odds,” Morgan says. “Failure will be the toughest opponent you’ll ever face.”

The U.S. Bureau of Labor Statistics estimates that 20% of startups fizzle out after their first year and by the end of year five half of the businesses that survived one year are belly up.

“This gives you an idea of what you’re up against,” says David, who spent half his career in financial services and the other half in sales before founding the San Mateo-based consultancy firm, Azzurri Finance in 2007. “I made a decision to start a business in a vacuum,” he recalls. “I had one client and a sense that I could do it.”

Then Morgan hopped on board in 2008.

“It’s lonely at the top,” David says. “Not all outcomes are favorable. As an entrepreneur, how do you stay motivated in the face of seemingly insurmountable odds?”

In 2016, the Diolis merged their firm into Ravix Group, a financial resources consulting firm that has served early-stage, venture-backed startups in Silicon Valley for 20+ years.

In 2019, over Labor Day weekend, Morgan sketched out an outline and ran it by David. “It was time to write a book,” he told his brother.

“Never Startup Alone” is fast-paced and written in a conversational style. Although the authors took a tough-love approach, they did it with a twist of humor and a dose of pop culture. The chapters are lined with famous quotes from an array of influencers, including Albert Einstein, Sun Tzu, Yoda, and “A Clock Work Orange.”

“There’s no question about whether or not the subject matter is dry. The challenge for us was converting this material into something engaging,” says David, who has experienced all aspects of the exit spectrum via the likes of Intuit, Twitter, Avi Networks and Sol Focus.

The body of the e-book is somewhat technical as the authors explore operational issues, such as formation, cash management, gross margin and unit economics.

“Never Startup Alone” doesn’t just cater to venture capitalists and entrepreneurs. The tenets, they say, are translatable to any industry, including flower shops or restaurants.

“We grounded the book in as many areas as possible that are familiar to people,” David says. “Anyone who has ever started anything will relate to this book.”

The editorial process came together quickly. The brothers, born six minutes apart, began weaving their life experiences on nights and weekends. They solicited feedback from friends and family and made revisions. This process repeated itself for several weeks until they brought in professional proofreaders and editors, consisting of former colleagues and their referrals.

Within five months, what began as disjointed bullet points in a Google doc, was ready for download. The authors weren’t interested in a tell-all expose, a memoir or a case study. “Our goal was to create a useful guide,” Morgan says.

The most intensive aspect of the project was finding and selecting relevant quotes, according to the Diolis, who aimed to provide a sobering, yet thought-provoking, account of the challenges facing startups and entrepreneurs.

This article was edited and published by Rick Weinberg, California Business Journal’s Founder and Editor-in-Chief. Click here for Rick Weinberg’s biography.

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