How One Entrepreneur's Self-Published Book Established Him as an Authority: An Interview with Entrepreneur and Author Tim Cooley

For over a decade, Tim Cooley—author of The Pitch Deck Book—has been in the entrepreneurship space on both sides of the table.

“I got involved in fundraising when I was in college. We would get money from a big bank and give it out to students to try ideas,” he shares. “Basically, I ran a little grant money fund. I got to hear hundreds of pitches, maybe thousands.” In the years that followed, Cooley tried raising capital himself, in addition to continuing to meet entrepreneurs and hear pitches. “What was cool about being on both sides of the table was I actually got to see what was getting funded, and more importantly what was going to due diligence,” he says. “I said wow, there are a lot more commonalities between the people who are getting funded and through to due diligence than people realize. And it’s more about what’s being said and not being said and the order in which they do it. And I was like, I have to help people do this.”

That drive turned into an hour-long talk on pitching, which a friend and investor urged Cooley to turn into a book. The result was The Pitch Deck Book, which he self-published in January of 2021. Cooley took some time to speak with Raab & Co. about the process of writing and publishing, his goals for the book, and how it has bolstered his business.

Planting the Seed

After the initial talk Cooley gave about how to put together a successful pitch, he was approached by a friend and colleague about it. “He said, ‘there are very few books like this that are just resources. I want a how-to and the way you presented it was so good, you have to do something with it. You have to turn this into a book,’” Cooley recalls. From the start, the impetus for the book project and its place in the market was clear. “So many people raise money, and the pitch is so important to the process and very few people put enough time into it. And they don’t even know what to do or what to say or why to say it, so that’s why I put together the book.”

Writing the Book

To get started, Cooley, took the talk he had given and began to build it out. “The talk and the book are probably 80% the same. I just added to it,” he says. “So the core of the book is what the slides should be, what should be on them. Then I added things that most people don’t think about. For example, what to do differently if you’re going to pitch on a Zoom call.” One of the benefits of self-publishing that Cooley utilized was the ability to continuously edit, adjust and add to his manuscript right up to publication. “I would get feedback and add more to it. Or after I started writing, I would go in and hear pitches, and someone would make a mistake, and I would start making notes and keep updating the book,” he recalls. “I did this until I got to the point where I hit 98% of all use cases.”

For that additional content, Cooley used text-to-speech to write the first draft. “I think the hardest part about writing is getting words on the page. Text to speech is a really clean way of doing that.” Once he had a completed draft that he had read through countless times, he let it sit for a little while before sharing the manuscript with his first editor: his mom. “She and I went through it I don’t know how many times,” he shares.

The next step was hiring an editor, who he connected with via referral from a colleague who had written many books. “I got to where I wanted an outsourced editor, so I used his person, who was really good but not good for me,” Cooley says. “They didn’t speak how I spoke. Very British, very different style of communication where I wanted to be very informal like we were just having a chat.” Nonetheless, they gave helpful content editing notes, pointing out sections that needed additional explanation. “I learned from that and hired a second person, to whom I said ‘I’m looking for a very conversational tone, but I also don’t want grammar errors.’ That kills credibility,” says Cooley. The second editor helped him polish the book to exactly how he wanted it. Finally, he hired a cover designer. “I kind of knew what I wanted from a visual perspective so what I said was I just need colors, and they gave me a good idea there.”

Becoming an Authority

“I wrote the book for two reasons. One is that I had this knowledge that I wanted to share. The second is that now, I’m the author of The Pitch Deck Book,” says Cooley, of how he wrote the book to establish himself as a credible authority in his industry. “A few years ago, I went to this conference in Utah that had Gary V and Kevin O’Leary and some other big names. This dude gets up there and says ‘if you want to be an authority, be an author.’ And I said that makes sense. He gave out thousands of copies of his book.” Cooley wrote his book with hopes of using it the same way.

But there was also a second lesson he learned from that same conference attendee: If you’re going to take the time to become an author, you need to put in the effort to produce a high-quality book. “It was sitting on my shelf, and I thought about the phrase ‘if you want to be an authority, be an author.’ So I said okay, I’ll read this book. And it was so terrible,” Cooley shares. “Grammar was bad, a third of the book was pictures. It was just enough pages for him to call himself an author, it gave him the spine of the book, so if you put it on the shelf, you see his name.” When he set out to write The Pitch Deck Book, Cooley did so with this bad experience in the back of his mind. “Writing a book takes a long time, and it should,” he says.

“It’s a business card,
and if somebody reads it,
you don’t want to come off unintelligible.”

Cooley also has a larger goal for his book to become a go-to resource for the entrepreneurial community. “In every industry, there are like five resources, five books that everybody reads. My goal is to be one of those books,” he says. “I want it to be the book that gets recommended by the small business development center.” While he is also pursuing consulting with the book, Cooley is most excited about his new podcast that has grown out of it, called Pitch Us, where he hears pitches from companies seeking capital and offers advice.

If the reviews of his book are any indication, Cooley is well on his way. “Tim is a master. He’s clearly seen it all. You can tell whenever someone is truly great at something because of how easily they can boil it down and articulate it. Read this before you do any raising!!” urges one recent reviewer. “Having done many pitches myself, I can tell you that ignoring his advice is at your own peril,” writes another. “Follow Tim's recipe and your odds of succeeding increase exponentially.”

There are a few things Cooley wishes he knew more about before becoming an author: the order in which publishing milestones need to happen, the best way to plan ahead, how intense fact-checking and proofreading is, and the most effective way of marketing and publishing.

For all these reasons and more, it's best you get in touch with a company like Raab & Co. to help you streamline the whole book publishing process!