Amber Gray

Founder of Trusty Oak

Amber Gray is the founder and CEO of Trusty Oak, an Austin-based virtual assistant company providing administrative and marketing support to busy entrepreneurs, 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, Trusty Oak was named Freelancer Hiring Platform of the Year, and 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.

Where did the idea for Trusty Oak come from?

It started with me feeling frustrated with my job at a digital marketing agency. I wanted to do something different and I hoped to make more money. I started looking for a job that would utilize more of my project management skills but wasn’t having any luck. After a couple of months of not even getting interviews, (mostly because I did not have a college degree that was required for the positions I wanted) it was starting to look like I wasn’t going to get the job I wanted. So, I opened my mind to the idea of starting something on my own and the idea fell into my lap.

I saw a video on Periscope from a founder of another VA company that was sharing that they were hiring virtual assistants. I started looking at his company and applied for a job. It was a part-time contractor position, the pay rate was lower than what I was currently making, and they said I was overqualified, but it intrigued me still. The next day, I had this lightbulb moment in the shower. What if I start a company that provides virtual assistants? And then, I went to work figuring it out!

What does your typical day look like and how do you make it productive?

I always spend the first hour of my day on my own morning routine that includes reading my Bible and taking a moment for prayer, reading my favorite newsletter, The Morning Brew, and taking a short walk with my dog.

On Tuesdays, I go to my chiropractor for my weekly adjustment. On Wednesdays and Fridays, I also go for a run in my neighborhood (I’m training for a half marathon!) I shower, eat breakfast, and check my email before my daily huddle with my team at 10:13 am and then jump into the day’s tasks.

I am a big fan of time-blocking so on Sundays, I set time blocks accounting for every minute of my workday for the week ahead. It may seem a little overkill to some folks but it helps me stay focused and reduces decision fatigue. I also use a software called Align where I write in and track progress on my individual priorities and company priorities for the quarter, week, and day.

How do you bring ideas to life?

For most of my ideas, the only way they become reality is by delegating to others. I tend to dream big and develop ideas that are too much for me to tackle on my own, so having a strong, dependable team is my key to success. I have continuously worked on my delegation skills as well as my processes for finding, vetting, and hiring talented people to do the necessary work to make my ideas come to life.

What’s one trend that excites you?

After 2020, we all are now familiar with the advantages and challenges that come with working remotely. I have been working remotely full-time since 2015 and worked remotely part-time since 2010, so the pandemic didn’t have the same impact on me as many others. However, now that we’re all in the same boat, I am seeing a significantly increased acceptance and adoption of utilizing virtual assistants. This is exciting to me because this trend towards remote work has caused our business to grow even more, and more folks are seeing the incredible value VAs can bring to the workplace.

What is one habit of yours that makes you more productive as an entrepreneur?

I already mentioned time-blocking which is definitely a habit that I can say helps me to be more productive, but the one habit that I cannot live without now is to set aside a full day once per quarter to plan my individual and company goals and tasks.

I work with a coach that holds me accountable and each quarter, walks me and my team through an intense day of digging deep to determine what I really want and what it will take to achieve those planned outcomes. I document my goals and priorities and then break those out into tasks with deadlines. This routine practice definitely contributes to my productivity and overall focus in the months following.

What advice would you give your younger self?

Keep searching for your true purpose and unique ways you can contribute to the world around you. And when you find that purpose, give everything you have to live a purpose-fulfilled life every single day.

Tell us something that’s true that almost nobody agrees with you on.

I’m going to be vulnerable here and share something that I wrestled hard with for many years.

You can be gay and a Christian, too.

My faith is imperative to my success as an entrepreneur and to fulfilling my purpose in this one, short life. And I am gay. I used to believe that it was impossible to be both but after years of soul-searching and studying the Bible on my own, I found my truth and peace.

As an entrepreneur, what is the one thing you do over and over and recommend everyone else do?

Delegate! Stop trying to do it all yourself. Share your vision with your team constantly. Don’t be afraid to trust others. Hire people smarter than you in areas you know you lack experience or passion and then trust them to carry out your vision.

What is one strategy that has helped you grow your business?

I hired a coach as soon as I could afford to do it, and I wish I had done it sooner! I could only get so far without an experienced outside perspective and someone to push me and hold me accountable. Working with a coach has had a direct correlation to business growth – both growth in revenue and growth in the size of my team. He has taught me effective ways to manage my big goals and most importantly, to focus on the outcomes I want before I strategize how to get there.

What is one failure you had as an entrepreneur, and how did you overcome it?

At the beginning of launching my business, I did not place a high enough value on my services and expertise. I have always been committed to excellence and will do whatever it takes to give our clients and our team the best experience possible, but this has come at a cost that I did not anticipate when I set my prices initially. I was afraid to raise my prices and lose clients, but when I did finally raise my rates, I saw the quality of clients we serve go up as well.

I overcame this failure by working with a fractional CFO who helps me understand my investments back into my business and helped me see that I was netting far less than I could be if I raised my rates even 15%. Working with a numbers person who could forecast for me gave me the insight I needed to let the fear go and just do it!

What is one business idea that you’re willing to give away to our readers?

I love finding hacks for productivity, communication, and team connectedness. I started exploring built-in tools within Google Workspace and found a very cool use for Google Sites. It started out as a way to document some of our processes and policies for the team because it is only accessible if you have an email account on our domain name. We continued to build out training material including videos and templates to help our team. Now we have a robust “intranet” that we call the Treehouse and it is a valuable resource for new hires onboarding as well as existing team members looking for information and tools to help them succeed.

What is the best $100 you recently spent? What and why?

I purchased a year’s subscription to, a video screen-recording app. I record videos to communicate with my team, follow up with leads, and check in with clients with a personalized video. I constantly receive positive feedback about the personalized videos and believe people engage more with video than written messages. When we can engage two senses at once, our communication is more effective.

What is one piece of software or a web service that helps you be productive?

Well, I’d have to say Loom is the one tool I lean on the most often to help me get more done! I love how easy it is to use and it frees up my schedule to have fewer synchronous meetings while still maintaining a personal touch.

What is the one book that you recommend our community should read and why?

The Speed of Trust, by Stephen M.R. Covey. This book inspired the name of my company (Trusty Oak) and actually helped me establish my core values. The premise of the book is that when trust is high, speed goes up and cost goes down. Developing trust in our business and personal relationships is critical to success and this book provides actionable advice for increasing trust in our relationships.

What is your favorite quote?

“If you want to go fast, go alone. If you want to go far, go together.” – African proverb

Key Learnings:

  • Discover your purpose first and foremost, then live a purpose-fulfilled life every day.
  • Delegation is the secret sauce! My ability to delegate has a direct impact on my business growth.
  • Being intentional about goal-setting and time-blocking gives me the ability to do so much more with my time and efforts.