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Stoic Street Smarts

Never be afraid to ask for help: The Book Proposal Story

Published about 1 month ago • 8 min read

This past week, I submitted my first manuscript, "Hard Lessons From The Hurt Business." This is a tremendous occasion because now I get feedback directly from the person who will sign off on my book. I celebrated by having tacos and reflecting on the challenges of writing this book over the past year.

I've already talked about those challenges, but for people new to the newsletter, the abridged version is "new baby and moving." I made it happen, and most importantly, I made it happen without sacrificing my family time or health.

As my wife put it, "You never made us feel like we were a distraction."

In today's newsletter, I want to walk you guys through my process of getting the book deal. I'm writing this out for a few reasons.

  1. I've been meaning to document this entire process for a while. This newsletter also serves as a diary of my thoughts and experiences. While writing my book, I referenced several newsletters to ensure I got the details and ideas correct.
  2. This process is a valuable lesson in the power of networks, goodwill, and persistence. If you are considering getting a traditional book deal, you can learn a few things from my experience that might surprise you. If you aren't looking to get a book deal, there are a lot of valuable lessons here, both in the story and what I will explicitly state.
  3. There are a lot of people who helped me. While I went through and thanked every one of them personally a year ago when I got the deal, I want to thank them again. This gives me a chance to do that.

Before we get into that, I want to let you know I'm back to writing and social media coaching. Now that the book is (mostly) complete, I'm back to all things related to social media writing. I've got 9 spots left for my Engagement for Growth group.

In the group, I and others will engage with your content, and you will receive direct coaching on how to use the algorithm to grow faster, make more money, and gain a bigger reach. This three-month engagement program is a huge discount from what I charge for my one-on-one coaching.

Enrollment ends this Friday, the 24th OR whenever the remaining spots are filled, but the sooner you get in there, the sooner I can start working with you. Learn more below.


Never be afraid to ask for help: The Book Proposal Story

In 2021, I hired a PR firm. My primary goal was to generate enough press to get a blue checkmark (this was before you could buy them for $8), and the secondary one was just to get my name out there even more. I wasn't sure what my next direction was, but I've always believed in Jack Butcher's idea: "Build the distribution, then build whatever you want." I figured that by increasing my reach, I'd always have options.

The PR firm pitched me to various podcasts, but one, in particular, wanted to interview me before booking me. I've done these before, so I figured it was no big deal. I'm a cool dude with an interesting story, so I treated the interview as a formality. I still put my best foot forward but knew I was a shoo-in.

Well, it turns out that Dov Baron, the host of Loyalty and Leadership, did not think I was a good fit for his podcast. However, he told me that he liked me and wanted to help me, so he offered me a deal: I write up a strategy to improve his Twitter engagement, and he'll have me on another show he hosts called "Curiosity Bites."

My goal was to continue beefing up my distribution, so I made the plan, got on the podcast, and went on about my business. Then, almost a year later, I heard from Dov again via text. He just wanted to catch up because that's the type of cool person that Dov is.

While on the call, he asked me what my next steps were. I typically hate this question, as I often don't know, but I knew I wanted to write a book. He told me about his friend Wendy Keller, a book agent, who was running a class in September teaching aspiring authors how to write a book proposal. The class also included feedback from her editors on each section.

A short primer on the book proposal

In case you didn't know, a book proposal is what you need to get a book deal from a publishing house. Non-fiction books are not sold as complete works. That's reserved for the world of fiction. Rather, a detailed layout of a non-fiction book is what gets publishers interested. This is where book proposals come in.

Think of this analogy:

A book proposal is to a book as a business plan is to a business.

A business plan is used to lure potential investors who will provide capital to launch your business idea, and a book proposal is used to secure the backing of a publishing house for your book.

I won't go into all of the positives about getting a publishing deal from one of the major houses (Nat Elison and Tiago Forte have great articles on that already), but I will say that anyone who tells you that you should self-publish instead of taking a book deal has never been in a position to choose. In other words, they don't know what they're talking about.

The Power of Your Network

About halfway through Wendy Keller's class, I remembered I had a massive network of published authors, so I began asking them for pointers on getting a book deal.

I talked to everyone from James Clear and Mark Manson to Rob Henderson, who, at the time, had just finished writing his first book (it's excellent. You should pick it up; I'll be doing a full review on it shortly).

One of the authors I talked to was Jimmy Soni, the author of excellent books about ancient Rome, mathematicians, and Paypal. I was connected to Jimmy through my long-term web designer, Jon Persson, who also designed Jimmy's website. (If you're looking for a web designer and you dig my website, then I strongly recommend hitting Jon up. Let him know I sent you to recieve a special discount.)

Jimmy gave me some great advice, but one of the more interesting things he suggested was that I read an article by Financial Samurai about the pros and cons of self-publishing vs. traditional publishing. Jimmy thought I was at the right place in my career to switch to stepping up to a book deal, but he suggested I take a look at the article, just in case I couldn't get an agent.

After I read Financial Samurai's article, I praised it on Twitter and sent him a message asking if he could give me any advice. We had a quick phone call, during which he dispensed some valuable advice and asked what my book was about. After I gave him the rundown, he offered to introduce me to his agent.

Or, at least, that's what I thought he said.

I got an email from the agent, but when I read the email signature, I realized I had not been introduced to his agent. I had actually been connected with the executive editor at Penguin Randomhouse's Portfolio imprint. He researched me, asked for samples of my most popular Twitter threads, and told me to hang tight for a few days while he talked to his bosses.

A few days came and went, and I got a phone call telling me everyone at Penguin would be thrilled to have me on.

Afterward, Noah and I had a phone call, during which he strongly suggested I get an agent. It wasn't mandatory, but he explained that an agent could do things I couldn't and that although Penguin was interested in working with me already, an agent would be much more likely to increase my chances of success. I agreed, and he introduced me to Howard Yoon.

Noah thought Howard and I would be an excellent match because of the type of projects he'd worked on before, and he also thought that Howard was a great agent.

Well, Howard certainly lived up to the expectation. When I sent Howard the proposal I'd been working on in Wendy Keller's class, he told me, "This isn't the type of book you need to be writing."

Howard reviewed everything I had done and the parts of my story that had resonated with people. From there, he helped me craft a proposal that got me a book deal and a $210k advance.

You never know who is watching.

This order or operation—a publisher introducing a potential author to an agent—is relatively unusual. Usually, an author pitches an agent, and the agent then pitches the publisher.

I highlight this because I was able to skip many of the more grueling parts of the process by reaching out through my network. Granted, this network took a decade to build, but this entire process was the first time I'd ever contacted people in my internet network for help.

Throughout this process, I was reminded that you never know who is watching. Not only is there nothing to gain by being rude online, but you can cost yourself opportunities that have yet to materialize.

You have no idea who is following who or who is watching a conversation.

While I generally believe that most comments made on Twitter have a short half-life, they still exist, and people take screenshots. Carry yourself in the DMs as if everything is a screenshot.

This article tells the tale of a young man who had a volatile interaction with me Twitter, and he learned this the hard way.

I'd later learn that Howard was also in the midst of becoming a partner with the William Morris Endeavor (WME) talent agency. To save you the Google searches, WME is the largest talent agency in Hollywood.

All your major A-listers are either with WME or Creative Artist Agency (CAA). WME also handles the who's who of the music, sports, and writing worlds. Howard believed enough in me as a writer to still be interested in signing me, knowing this would happen.

I don't know how this will help me when the book is released, but I know it will.

Don't be afraid to ask the tough questions

There is one more person in this process who helped me out. Early in the process, after connecting with Howard but before being officially offered a deal, I got a subscription to Publisher's Weekly.

This site is mostly read by publishing industry professionals, and it's a great place to find agents and authors they represent. My years of dealing with the internet marketing space have made me independently verify anyone I choose to work with, so I did some digging on Howard. During this process, I discovered that my friend Nat Eliason (mentioned earlier in the newsletter) had his book acquired by the same editor who introduced me to Howard.

I asked Nat about the process and if he could send me his proposal to help me recraft mine. I also wanted to know what he got for his advance, and he didn't mind telling me.

I didn't accept Penguin's first offer for my book because he told me what they paid him and because I knew his audience size was only a little larger than mine. I was able to confidently counter, citing that I was aware of what Nat got and the respectable sizes of our audience.

That move—a move I wouldn't have felt comfortable making had it not been for Nat disclosing what he got—got me an extra $35k, a $40k incentive bonus (So I potentially will earn $250,000), and some rights that are not typically granted to first-time authors.

While I have no idea what my book's sales and future will be, I know that the relationships and network I've built over the last 10 years will tremendously help the promotion department. At the very least, I haven't set up any barriers that will make promoting my book more difficult than it needs to be.

In summary, don't make enemies for free, and don't be afraid to ask for help. Generally speaking, people are excited to share what they know and help you IF you've shown yourself competent and relatable.

Stoic Street Smarts

Teaching hard lessons from the hurt business

Teaching what I've learned from the hood, the ring, and everything in between. Join 35k other readers to learn how to manage risk, build relationships, and confront reality.

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