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Drew D’Agostino of Crystal: “Particular long-form podcasts interviews can be great as well”

Tying your book into a distribution strategy with your business is another excellent way to promote your book. For example, we send our enterprise customers signed copies of our books, and then they have them in their offices, generating lasting value for them. As a part of our series about “How You Can Grow Your Business […]

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Tying your book into a distribution strategy with your business is another excellent way to promote your book. For example, we send our enterprise customers signed copies of our books, and then they have them in their offices, generating lasting value for them.


As a part of our series about “How You Can Grow Your Business or Brand By Writing A Book”, I had the pleasure of interviewing Drew D’Agostino.

Drew D’Agostino is the co-founder of Crystal, the app that tells you anyone’s personality. Using AI, Crystal accurately identifies a person’s motivations, communication style, and other behavioral traits. Thousands of professionals globally use Crystal to communicate more effectively, write more persuasively, and build trust faster with new people. Previously, Drew was CTO of Attend.com, an event management software company. Drew and his company have been featured in Inc, Fortune, CNN, Fast Company, MIT Technology Review, Wired, and The Guardian. He is the co-author of a book published by Wiley in November 2019, Predicting Personality.


Thank you so much for joining us in this interview series! Before we dive into the main focus of our interview, our readers would love to “get to know you” a bit better. Can you share a story about what motivated you to become an expert in the particular area that you are writing about?

I didn’t initially set out to write a book; I set out to start a company. Our company, Crystal, sat at a unique intersection between psychology, data science, and technology. There was a lot of overlap where I could bring in my other interests; while I wasn’t an expert in any of those three areas per se, I knew enough about each: the underlying core psychology of personality frameworks and DISC, machine learning and data science, and SaaS — how to build a software and deliver a product. When you combine those three things, you get Crystal. It was about five years since starting Crystal that we wrote the book. I viewed the book as my “college thesis” because I learned a lot and had been a student of psychology and technology throughout the process. It started as an internal project because I wanted to put all that I had learned into one concise piece of work. The original intent wasn’t to publish a book but an exercise to assemble my unique perspective and all of the lessons learned, knowledge gained, and research gathered over the years. The motivation was very different from the outcome.

Can you share a pivotal story that shaped the course of your career?

I’ve always wanted to be an entrepreneur, and two failures shaped the course of my career.

During my senior year of college, I started my own bed bug extermination business. I became a licensed pesticide applicator, I bought a trailer to carry around all of my equipment, and I had my own bed bug costume, which I wore while passing out flyers to promote my business. After about 3–4 months of working hard at this business and solving peoples’ bed bug problems, I realized I was good at the marketing aspect but not very good at executing it. In the end, there was a moment when I was holding a bed bug between my fingers, squeezed it a little too hard, and it popped. I looked at the mess and realized I didn’t want to do that with my life! I realized that there were a lot of different parts of technology and software that are really appealing (mainly that you don’t have to get on your hands and knees and look for bed bugs all the time), so I went back to building websites and software as a freelancer instead.

About two years later, my business partner Greg and I started a venture-backed software company, Attend.com. We later had a giant conflict with our board and ended up getting fired from our own company. You can read all about that in our book, but needless to say, it was a second major pivotal moment in my career.

Those two moments nudged, maybe even forced, me into the direction I found myself in.

What are some of the most interesting or exciting projects you are working on now? Are you working on any new writing projects?

I’ve been experimenting and prototyping a lot with the new AI technology. I am basically trying to figure out how to use AI to write content automatically. Whereas historically, Crystal is full of content written internally, we are now figuring out how to use this AI tool as an assistant to accelerate our writing. Down the line, we will build it into our product and create content that looks like a human has written it. This has been more of a technology project rather than a writing project.

Thank you for all of that. Let’s now shift to the core focus of our interview. Can you please tell us a bit about your book? Can you please share a specific passage or story that illustrates the main theme of your book?

The book is a comprehensive guide on using DISC as a personality framework to help you communicate and relate to others better. It also takes it a step further to use technology not just to know DISC but also how to predict it and apply it in business. One of my favorite parts of the book to write was a section where I described how group dynamics work because I got to write about and dive into the relational dynamics of my family. It was fun because I was able to map them out on the DISC diagram and describe them more scientifically. This helped me understand the dynamics that had been dominating our communication and relationships for our entire lives. It was illuminating for me personally, and I think many other people get that experience taking DISC assessments when they do a similar exercise with the results. It was fun to write, and it’s also useful as a model for people to start putting this concept into application.

You are a successful author and thought leader. Which three character traits do you feel were most instrumental to your success when launching your book? Can you please share a story or example for each?

  1. An important character trait would be “curiosity,” or the willingness to go down a rabbit hole without really knowing where it leads. When we were first approached to write the book, we initially declined. A year later, I started the project and, after writing 30,000 words in a draft, realized I had the beginnings of a book and sent it off to that same publisher. The writing project was a rabbit hole I went down, and it ended up in a book deal.
  2. Another instrumental trait would be “openness,” or transparency. The parts that people connect to most in this book, the ones I always hear about, are when people are learning about our personal and business stories. We are very open about our flaws, shortcomings, and what worked and what didn’t — I think when you are vulnerable in front of an audience, it helps them connect.
  3. A third important trait would be a willingness to have “fun” with technical concepts. You can read psychology and business books, and they tend to be dry. With our book, we were willing to have fun with the concept. At one point, we take all the characters from The Office, map them, and talk about different scenes from the show and how the personalities work together. We also use a lot of metaphors that make the information more accessible and fun.

In my work, I have found that writing a book can be a great way to grow a brand. Can you share some stories or examples from your own experience about how you helped your own business or brand grow by writing a book? What was the “before and after picture?” What were things like before, and how did things change after the book?

Writing the book forced us to consolidate our ideas and articulate our brand and mission in a much more specific way. It also helped us develop the concept of Personality AI, define what the purpose of Crystal is, and explain why people are excited about it. Having this book gives us credibility and authority, and it serves as an excellent resource for our customers.

If a friend came to you and said “I’m considering writing a book but I’m on the fence if it is worth the effort and expense” what would you answer? Can you explain how writing a book in particular, and thought leadership in general, can create lucrative opportunities and help a business or brand grow?

If you have something to say, you should write a book. You should not write a book just for the sake of writing one. If you are on the fence, that could indicate that you don’t actually want to write a book; you just think that you should. I wouldn’t look at a book as a silver bullet to grow a business, but rather if your company has a lot of thoughts coming out of it, a book can be a core asset to help articulate your mission, vision, and goals.

What are the things that you wish you knew about promoting a book before you started? What did you learn the hard way? Can you share some stories about that which other aspiring writers can learn from?

We haven’t done much outward promotion with our book, as we’ve used it as an asset to be the core layer of Crystal thinking and to start and maintain conversations with our customers. We give the books out to our enterprise clients, so they generate returns, but over a slower and steadier pace. If your goal is to make money off your book, the promotion strategy would be much different. Writing the book, I learned that it is crucial to have extra sets of eyes and a small network of people who are highly invested in your project to read it over and give you feedback. For editing the book, you are primarily on your own to communicate your ideas properly and organize your writing well.

Based on your experience, which promotional elements would you recommend to an author to cover on their own, and when would you recommend engaging an expert?

You can’t outsource the reason for writing the book — the core meat of the book has to be your own. If you don’t have that, you’ve got to go live some life, write things down, and then you’ll have something to say. You can outsource almost everything else. I’ve needed a lot of help editing, both in terms of grammatical, technical stuff but also organization and figuring out where ideas should go. It is also super helpful to have a designer for graphics and someone to handle the logistics, list-building, and promotion. Lean on your network as much as possible for outsourcing, but the author should own the core ideas and writing style.

Wonderful. Here is the main question of our interview. Based on your own experience and success, what are the “five things an author needs to know to successfully promote and market a book?” If you can, please share a story or example for each.

  1. One of the things that have paid off for us is shooting high for endorsements — you never know who will say yes. Imagine the ideal person you’d want to have on your back cover — in our case, it was Tony Robbins, and he said yes! You have nothing to lose by aiming high.
  2. Involving influential people within the book’s content can be very helpful because they will promote it themselves if they are in the book. Doing that for a non-fiction book can be very helpful. Organic word-of-mouth, as opposed to blasting out promotions, is long-lasting.
  3. Tying your book into a distribution strategy with your business is another excellent way to promote your book. For example, we send our enterprise customers signed copies of our books, and then they have them in their offices, generating lasting value for them.
  4. Particular long-form podcasts interviews can be great as well. They can sometimes be a hit or miss, but they can provide a lot of long-lasting value if you hit one. We’ve had a couple of NPR shows that had a lot of traction and worked well.
  5. And finally, a great launch party!

We are very blessed that some of the biggest names in Business, VC funding, Sports, and Entertainment read this column. Is there a person in the world, or in the US, with whom you would love to have a private breakfast or lunch, and why? He or she might just see this, especially if we both tag them 🙂

I would love to sit down with psychologist Jordan Peterson. Before he became famous for all of his books, he was a leader in personality psychology. His work has inspired a lot of my thinking on this subject. He focuses more on self-improvement and development now, but much of his previous work has been pretty influential for our book.

How can our readers further follow your work online?

You can learn more about our product and book at https://www.crystalknows.com/!

Thank you for these excellent insights, and we greatly appreciate the time you spent. We wish you continued success with your book promotion and growing your brand.


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