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Welcome to The Book Marketing Action Podcast with Becky Robinson and Christy Kirk. We are happy to reconnect with David Greer, an old friend, and client in the early years of our business.  During the episode, David shares his passion for holiday letters and the process of how he’s incorporated book marketing into each letter he sends. 

Becky: Before we get started, I want to give David a chance to introduce himself. David, could you tell us a little bit about yourself, your work in the world, and about your book?

David: Thanks, Becky! I’m an entrepreneurial coach. So when I was still at University, 22 years old, I joined a young software startup and built that into a very successful software company. After that, I become an angel investor for startups. And then for the last 5 years, I’ve been an entrepreneurial coach, working 1 on 1 with entrepreneurs and their senior teams on strategic planning. 

What I’ve discovered in 35 plus years of being an entrepreneur is that there are a lot of patterns that get repeated. I eventually decided that I really wanted entrepreneurs who haven’t been through it before to have a resource where they didn’t have to wear or earn all the scar tissue that I earned. So I conceived my book, Wind In Your Sails: Vital Strategies That Accelerate Your Entrepreneurial Growth. I’m a very passionate sailer, so I used sailing analogies throughout the book. I interviewed 45 entrepreneurs for the book and featured 10 entrepreneur case studies. Over a third of the book is other people’s stories, so you not only get the advantage of my scar tissue, you get the advantage of 10 other people’s scar tissues. I definitely wrote it as an evergreen book, so it’s intended to have a lot of ways to think about your business, but very practical ways to apply it for a long period of time. 

Holiday Letters

Becky: If we have any entrepreneurs listening to this podcast, I hope you’ll check out David’s book and his work. 

David, I reached out to you about this podcast because this month we are focusing on holiday book promotions and how you can use the holidays as a means to get the word out about your book. I know by being on your email list for many years, that one of the things you do is send out a holiday letter. Let’s talk for a moment about holiday letters. Some people call them brag letters, what are other names we use for letters that come at the end of the year? 

David: Yeah, other names used are the Christmas letter, holiday letter, holiday newsletter, and family letter. 

Becky: Because it’s been so long since I’ve last sent one, I especially wanted to invite someone on the podcast who’s been sending holiday letters. David, share with us, how long have you been sending them? 

David: I can’t remember exactly, but at least 30 years. 

Becky: Wow! Tell us a little bit about your process, the types of information you include, and who the letters go to. 

David: For me, the Christmas letter is a very personal letter, so it goes to family and friends. It also goes to a few entrepreneurial friends who I have a close, personal relationship with or I feel I’ve connected to them in some way. 

The way we’ve written them is fairly consistent for 30 years. My wife and I always write them together. I always write the first draft and think of any photographs to include, because I’m a photographer. Part of the process is getting the whole family together for a picture. I usually keep it to two typewritten pages so single sheet, double-sided. After I write the first draft, my wife adds her part and then edits and revises it. 

Becky: Wonderful. David, you did say you send these in both a print and digital format? Talk to me about that. 

David: I love getting Christmas cards and letters. Especially from the people who I don’t keep in touch with enough, and people who I see on social media on a regular basis but they don’t share details such as their husbands changing jobs, their moving in a new direction, different stage of life, etc. I have some people who’ve sent me their family letter for 30 years. It really helps me stay connected to those people, and I always read the letters when they first come in. It’s something that’s very special to me. 

Becky: It sounds like a very important tradition in your life. As I’m listening to you, I’m wondering if our listeners are thinking, well what does this have to do with book marketing? So let’s talk about why we are bringing this topic of holiday letters into a book marketing podcast. To do that David, tell us about how you’ve incorporated your book and business offerings into the holiday letter. 

David: So we have three children and there is always a section about each of them. And then, the section on my wife and I almost always has an aspect that talks about our work, what we are doing, and what’s new or different. In 2015, the Christmas letter definitely included the announcement of the launch of Wind In Your Sails. I’m sure the digital version of the letter included links to Amazon. Last year in the Christmas letter, I had openings for more clients so I let everyone know, and actually had a personal friend reach out to me and became a client of mine. We also mention our daughter and son-in-law’s landscaping business in the letter, which generates them more clients. 

Becky: That’s amazing and so great you’ve been able to help fuel that success for your kids. I love what you’re saying about making sure there is awareness so that your family and connections really understand what you’re up to in the world. I think sometimes we make the assumption that if we include something about our new book or work in our letter, that it’s self-promotional. I always try to reframe that with authors on a few different levels. One is that if you have a book that can make a difference, you’re not promoting yourself, you’re promoting your message. I think one thing that we underestimate is the way that our letters are received. And what I hear you saying, David, is that you love to receive these letters and are hungry for insights into your friends and family’s lives. If we can imagine the recipient of our holiday letter, well, of course, your book deserves a place in that letter because it’s a huge accomplishment. 

David: That’s correct. Absolutely! Why would you not include something so significant in your life? How many people can say they’ve written a book? Yes, a lot of people have written books, but in the huge scheme of the global population, it’s still this massive, massive achievement to get a book finished and published. 

Becky: Yes! And so would your connections want to celebrate that with you? 

David: Yes! And then for me, there is also a cultural alignment piece. In that, one of my deepest, cultural core values is massive family connection. To me when I send the family letter, even to the people who I’m connected to from business, it’s just consistency about what I really stand for. 

Action Steps

Becky: That’s very powerful. So reinforcing through your routine activities the values that you stand for in your life and work. Every time we finish the podcast, we always wrap up with some action steps. We want you to be able to take action based on what you hear. So we have three action steps from today’s podcast:

  1. Include your book in your holiday letter. If you currently send a holiday newsletter, what we’d like you to do is consider including your book this year. 
  2. Consider sending a holiday letter. If you’ve never sent out a holiday newsletter, consider sending out a holiday newsletter this year and start to identify recipients.
  3. Share the good and the bad. Include the challenges and the wins in your life in your newsletter, because it helps people connect to you on a human level. 


We hope you take advantage of the resources above and let us know if you take any action steps today. If you have any questions or topics you’d like us to cover, please email Becky Robinson here and Christy Kirk here

Reminder: We are going to conclude the first season of the podcast at the end of October. We are taking a break over November and December before coming back with fresh episodes in 2021

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