The Trusty Oak Blog

From the CEO’s Desk: Add These Books to Your 2020 List


I have always been a lover of learning and I regularly welcome the chance to do something I’ve never tried before. However, I have never had a formal education in business. In fact, I have never gone to college at all. Right out of high school, I became a full-time pharmacy technician and a part-time waitress. I worked in both retail and hospital pharmacies for over 11 years before realizing I had reached the peak of my career without a formal education. The only way I could keep growing without going to college was to make a career change, so that’s what I did.

I was fortunate enough to know an ultra-creative web designer who needed some help keeping projects on track and communicating with clients. My attention to detail and drive for executing processes and systems turned out to be the gift I’d learn to apply to web project management and digital marketing for five years. 

And then I took another leap of faith to launch Trusty Oak in 2015. Starting and running Trusty Oak has been my first experience as a business owner and even in our fifth year, I still have so much to learn. I’m also proud of how far I’ve come in the world of business over the last 10 years and it’s my passion to help others brave enough to take the entrepreneurial journey.

Someone recently asked me how I learned to run a business and where I go for business training. My answer? 

Aside from what I learned on the job over the last decade, everything I learn comes from business books and listening to podcast interviews with successful entrepreneurs and people I consider to be my business heroes. We are living in an era when self-learning is easier than it has ever been before. Resourceful people can find training on virtually any topic of interest. 

In this post, I’m sharing what I learned from ten books I read in 2019. If you are a business owner or have plans to start something up in 2020, this list is for you. 

The Automatic Customer: Creating a Subscription Business in Any Industry 

John Warrillow

Read: January 2019

When I wrote the first business plan for Trusty Oak, the business model was subscription-based, but I struggled with making it work in the beginning. In thinking through the packages, I got hung up on presenting the value to my clients since my company and services were new and I had not seen an example of this model working for a service-based company. I ditched the subscription model and found myself with more than half a dozen packages with various billing rates. It was fairly convenient for our clients but was an administrative nightmare internally. Clients were not in a contract and I had no idea what our revenue would look like from one month to the next.

A fellow business owner and client, Dr. Chris Larson, recommended The Automatic Customer: Creating a Subscription Business in Any Industry by John Warrillow and this book finally helped me put the pieces together. 

The greatest benefits of running a subscription business:

  • Establishing future income increases the value of your company
  • Cashflow improves and the model brings stability to finances
  • Consistent commitments from clients help you better manage your resources (employees, contractors, availability, and products) 
  • Increased transparency about pricing and deliverables improve client relationships

Applicable for both B2B services and consumer product businesses, this book is sure to spark ideas to implement for your own subscription business.

The Pumpkin Plan: A Simple Strategy to Grow a Remarkable Business in Any Field

Mike Michalowicz

Read: January 2019

First off, get used to seeing Mike Michalowicz on this list – Mike is my favorite author and I’m making my way through his books. His personal mission statement is to eradicate entrepreneurial poverty so every bit of his advice centers around my favorite topics of efficiency, automation, and laser-focused action items.

The Pumpkin Plan: A Simple Strategy to Grow a Remarkable Business in Any Field was the first of his books that I have read. This book inspired me to take a close look at the relationship, value, services, etc. associated with each one of our clients. This wasn’t an easy practice at all, but gaining a better awareness of how things are really going with each client was critical to our growth.

I learned how to identify the clients that would benefit most from working with us and how to nurture those clients to keep growing, while similarly learning how to cut ties with those that are either draining our company resources or simply not ready for the services we provide. It also inspired me to find new ways to serve those clients that are not ready for us yet but that will be down the road. 

This was a lesson in lead nurturing as much as it was about how to gracefully “break up” with some clients in order to free up opportunities to delight our best clients even more.

Profit First: Transform Your Business from a Cash-Eating Monster to a Money-Making Machine

Mike Michalowicz

Read: March 2019

As business owners, we stress out over the same sorts of things most of the time. At the top of that list? Money. Getting profitable. Paying ourselves. Most of us have income from sales, then subtract business expenses such as payroll, office space, software costs, taxes, etc. and then pay ourselves whatever is left. For many business owners, this may have meant skipping a paycheck or two. (Or maybe a lot more…) 

Profit First: Transform Your Business from a Cash-Eating Monster to a Money-Making Machine flips that cash management system on its head. Put simply, Mike taught me how to rearrange that math problem to subtract profit from sales and then pay expenses, making it possible for your business to talk back to you! Profit First helped me realize I needed to raise my rates, reduce some expenses, and budget more for my owner’s pay if I’m going to keep doing this long term.

Most importantly, the book walks through a very specific method for managing your finances in a way that increases profitability.

Bonus Tip: Hire a Profit First Professional such as Williamson Advisors to make the process easier than ever. (Thank you, Nancy, for changing my business and my life!)

The Obstacle is the Way: The Timeless Art of Turning Trials into Triumph

Ryan Holiday

Read: March 2019

Reading this book truly took me down a path of memories from my past as far back as my teenage years and evoked a sense of pride and self-love before it was all over. The Obstacle is the Way: The Timeless Art of Turning Trials into Triumph comes from stoicism, the ancient Greek philosophy of enduring pain or adversity with perseverance and resilience. This was a new concept for me, however, when reflecting on my life with a heart of gratitude, I realized just how much of my own trials have carved the path that has led me to the life I love today.

This book is more of a self-help/motivational one versus a business book but it’s written in a way that I believe is quite appealing to the business community. If you are feeling stuck or simply asking yourself “what if…” The Obstacle is the Way could help you find your way.

Building a Storybrand: Clarify Your Message So Customers Will Listen

Donald Miller

Read: April 2019

Building a Storybrand: Clarify Your Message So Customers Will Listen may be the single best book on the topic of marketing for small businesses (or really any business). Donald Miller’s process for simplifying your messaging is easy to understand and apply fast. I ended up with pages of ideas and notes while reading this book, and now our team has been reworking our marketing material and website content for better results.

Even if you hire someone to handle your marketing, read this book and apply the principles to developing your messaging for sales, emails, and your website content.

Clockwork: Design Your Business to Run Itself

Mike Michalowicz

Read: July 2019

In Clockwork: Design Your Business to Run Itself, Mike lays out a detailed strategy for doing exactly what the title implies and places a 4-week vacation as the reward and ultimate test of success. With tons of additional resources such as webinars, worksheets, and video content to help you put this concept to work immediately, Clockwork casts the vision for time freedom and business growth and then takes it home with a step-by-step process for identifying the most important activity of your business that should be protected at all costs, followed by tactics for shifting your time and energy toward designing your business and delegating tasks effectively.

Related Video: Stop Trying to Be Productive: 2 Ways to Optimize Your Business for Organizational Efficiency

The Speed of Trust: The One Thing That Changes Everything

Stephen M. R. Covey

Read: September 2019

This is not the first time I have read this book and I talk about it a lot already, but I decided to go through the book again this year for a refresh. The Speed of Trust: The One Thing That Changes Everything is the book that inspired the name of our company and Trusty Oak’s core values. Stephen M. R. Covey shares why trust is the currency of all relationships and unpacks 13 behaviors that can increase trust in our personal and professional relationships.

If one of your goals in 2020 is becoming a better leader, start with this book. 

Million-Dollar Women: The Essential Guide for Female Entrepreneurs Who Want to Go Big

Julia Pimsleur

Read: December 2019

Million Dollar Women: The Essential Guide for Female Entrepreneurs Who Want to Go Big is especially helpful for women who are interested in having their business funded. I have never been exposed to the world of Angel investors and venture capitalists so this book taught me a lot about how things work in the world of business fundraising. 

This was not fully applicable to my business since I have bootstrapped finances, but the best nugget that did apply to me was found in Chapter 16. Pimsleur devotes this chapter to the topic of delegating to a virtual assistant and shares how using a VA can help you scale your business. I couldn’t agree more!

Indistractable: How to Control Your Attention and Choose Your Life

Nir Eyal

Read: December 2019

This book was a quick read (or listen—I’m a fan of audiobooks!) and each chapter ends with a “Remember This” section that summarizes the key takeaways. Indistractable: How to Control Your Attention and Choose Your Life is actionable and succinct. Understanding the reasons behind my undesirable habits and obsession with scrolling has helped me to be mindful and take control of my own actions. I disabled most notifications on my phone and immediately noticed how my focused has increased. Understanding how much I have been distracted by both internal and external triggers is a big step toward becoming Indistractable!

Your World-Class Assistant: Hiring, Training, and Leveraging an Executive Assistant

Michael Hyatt

Read: January 2020

I have been following Michael Hyatt for several years and first learned about Georgia-based virtual assistant company, Belay Solutions (formerly EA Help) from his blog posts promoting the benefits of working with virtual assistants to grow and scale. (Which ultimately was how I got the idea to start Trusty Oak!) 

I pre-ordered his latest book, Your World-Class Assistant: Hiring, Training and Leveraging an Executive Assistant which provides solid, applicable steps for business leaders but also is highly valuable for virtual assistants and executive assistants. I love how the book is sprinkled with tips from EAs working on the Michael Hyatt and Company team.

If you are looking for nitty-gritty how-tos for delegating your inbox and calendar, this book has everything you need to know.

What’s on Your 2020 List?

Reading has consistently been a companion and teacher to me: what a gift to learn from the greats who’ve gone before me. I’ve got a list started for my reading goals for 2020 and I’d love to add your recommendations to my list! What must-read books should I grab this year? What’s on your 2020 list? 

How it Works

Amber Gray

Amber Gray is the founder and CEO of Trusty Oak, an Austin-based virtual assistant company providing administrative and marketing support to small business leaders, authors, and creative teams. A people-first approach to hiring, along with a scalable growth model have positioned Trusty Oak as a flexible, dependable, and affordable alternative to hiring administrative and marketing employees. In 2021 and 2022, Trusty Oak was named Freelancer Hiring Platform of the Year, and in 2021 Amber was recognized as Austin Business Woman of the Year.

Before founding Trusty Oak, Amber spent five years at a rapidly growing digital agency based in Austin, TX. Four of those years, she was responsible for hiring and leading both local and virtual teams while working closely with clients ranging from CEOs to bestselling authors to build their brand online. As VP of Operations, Amber helped lead the company’s growth to #15 on Austin Business Journal’s Fast50 List in 2014.

As a female founder and leader of a company that has quickly established a recognizably special culture within a non-traditional workforce, Amber has energized and empowered women from diverse professional and personal backgrounds to go against the grain of historically standard female roles in business, technology, and leadership. Trusty Oak provides an opportunity for experienced admin and marketing professionals to work independently as freelancers, but with a supportive internal network consisting of other ambitious and resourceful remote workers.

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