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Community Highlights: Meet Amber Gray of Trusty Oak

Today we’d like to introduce you to Amber Gray.

Hi Amber, we’d love for you to start by introducing yourself.
In my twenties and early thirties, I would have never expected that I would start my own company one day, so it still feels pretty surreal that I have ended up so passionate about growing a business.

I got my first job doing manual labor on an exotic animal ranch in West Texas when I was 15 years old. As a teen, I held jobs at a grocery store, a bookstore, and a small community pharmacy. When I graduated high school with a 3.96 GPA, life circumstances forced me to keep working instead of pursuing a traditional path to college, so I kept working at the pharmacy and added a second part-time job at the Pizza Hut next door.

I ended up getting promoted to pharmacy technician quickly and stuck to this career path for 11 years. I was 29 years old when a friend encouraged me to learn more about project management and website development. She was a designer who was getting busier and needed a hand with keeping her projects on track and with gathering content from the clients, so she offered to pay me a few hundred dollars per project to help her out. I didn’t have a lot of experience using a computer, except for basic data entry and cash register work, so I had a lot to learn!

I picked up a couple of books on WordPress development and project management at Half Price Books and started learning as much as I could. This was the first time I had ever bought books about business, and little did I know that I would continue to learn this way and eventually learn enough to launch and grow a business of my own! To this day, I learn most of what I know about business through books, podcasts, and blogs.

My friend continued to give me projects and eventually, the startup marketing agency we were serving offered us both full-time positions. I worked diligently and advanced my position in the company almost every year. This was where I got my first taste of the startup life, but even then I had no idea I’d take the leap for myself after five years on the team.

In 2015, I was feeling unhappy in my role as VP of Operations at the agency and was looking for something more. When I wasn’t having any luck in my job search, I told myself to think bigger and just become open to any possibility…even if that meant starting something new.

And that’s when while browsing social media, I stumbled across a virtual assistant company for the first time. I had never heard of this industry but the work was very similar to what we were doing at the marketing agency and I liked the idea of serving similar clients. I applied for a job but it was part-time contract work for a lot less pay than I was making at the agency. But then I had the lightbulb moment while I was taking a shower – “what if I started my own VA company?”

I went to work reading online as much as I could about the industry, how to write a business plan and researched what other companies in the space were doing. And then I did something pretty unconventional – I gave my notice to my boss and asked him if he was interested in being my business partner. Thankfully, he agreed and provided me with a lot of guidance in the beginning as well as gave me the opportunity to work with my coworkers to develop my brand and website. It was the launching pad I needed!

On August 17th, 2015, I sat down at my desk in my home office for the very first time as the founder and CEO of Trusty Oak.

But I was also the first VA of Trusty Oak, the first marketing director, the first social media manager, the first talent manager, the first CSM, the first bookkeeper, CFO, admin, and everything in between!

I knew even on that first day that I was only the first of these roles, not the last. I wanted to grow!

One thing I have always known about my career is that I have wanted to be a part of something bigger than myself. As I’ve continued to develop my vision for Trusty Oak, I realize that this company gives me an opportunity to create a legacy with a grand vision to change the way people think about work and to see how our jobs serve a greater purpose beyond just making a living. Through my own personal journey, my work has become one and the same as my life’s purpose and my greatest joy, and I want to help others discover their own purpose and joy.

Even on that first day, I wanted to provide independent thinkers, motivated creatives, hustlers, and dreamers with a work experience like no other – a place where TRUST is high and individuals thrive and never run out of opportunities to grow.

I want more people to love their job through and through – to love their managers, their teammates, their clients, and the tasks they tackle each day. And most importantly, for more people to live their life knowing they are part of something bigger than themselves.

That is a big plan that no one person can accomplish on their own. By nature, it requires collaboration, creativity, drive, strategy, transparency, and caring leadership on every level. And that’s why I have a very values-based approach to leadership and a people-centric business model that supports those folks who have a growth mindset – both freelancers and entrepreneurs.

Today, Trusty Oak has two employees and 46 freelance virtual assistants in 17 states across the US. We currently serve more than a hundred entrepreneurs in industries such as software development, executive coaching, law, photography, construction, real estate, and non-profits.

We all face challenges, but looking back would you describe it as a relatively smooth road?
One of the most humbling phases of my entrepreneurial journey was in early 2017, just two years after starting Trusty Oak, when I had to take a couple of extra part-time jobs to make ends meet financially. I had just gotten divorced and even though I had eradicated most of my personal debt, I was still struggling financially.

My business was doing okay and I was able to make payroll for my small team but I personally was not taking much of a paycheck home. My only option if I wanted to keep my business going was to also earn income another way. I was driving for Lyft and working a few hours per week at a local software development firm as their office manager. My responsibilities as office manager included things like ordering snacks for the designers and developers, sweeping the floors, and even cleaning the toilets.

There were days when I felt like a fraud – my business cards said “Founder & CEO” but I did not feel like either of those things. Despite my feelings, I kept working and earning money any way I could to make it work and I eventually started getting my Trusty Oak paycheck up to a point I could live on.

Great, so let’s talk business. Can you tell our readers more about what you do and what you think sets you apart from others?
Too many entrepreneurs are overworked, overwhelmed, and lonely. Trusty Oak is on a mission to combat small business burnout and get companies growing by connecting driven entrepreneurs with the best freelance virtual assistants in the U.S.

For overwhelmed entrepreneurs who are ready for support, Trusty Oak has made all the difference. As one client put it, “Adulting is hard. Entrepreneuring is harder. I don’t know where I would be on either if Trusty Oak hadn’t come into my life when they did. Partnering with them has allowed me to scale my business, organize my life, and accomplish goals that would have been out of my reach without their support.”

It’s one thing to simply connect entrepreneurs with freelancers. Trusty Oak takes it much further, breaking through the remote technology market for freelancer hiring with a values-based culture, a strong network of interconnected, collaborative virtual assistants, and a commitment to transparency and accountability.

While the entrepreneur has filled out a simple questionnaire to get started with a virtual assistant, the behind-the-scenes work is where the true magic of our platform happens. Here’s what we mean:

The best of the best virtual assistants: Each VA who joins our team is strenuously vetted with assessments and interviews. Our vetting process takes weeks and whittles down hundreds of applicants to only a few qualified candidates. Only the best are given a coveted spot on our highly connected team.

Team approach: When you hire a Trusty Oak VA, you get a team. This is the Trusty Oak difference that has become so many entrepreneurs’ secret superpower: their VA is their ticket to a pool of qualified freelance rockstars who can help as their needs evolve and scale. Many of our clients start with one VA and expand quickly as they realize the potential for more help, better outcomes, and faster scalability.

A culture of growth: Trusty Oak believes in values-based leadership, which means we are committed to collaboration, transparency, and follow-through. Our unique virtual assistant mentorship program helps us ensure we’re staying true to our values in every interaction with our clients.

Trusty Oak’s motto is “keep growing,” and we walk this out on every level of our company. When we match a freelancer with a business, our work has only just begun to support the relationship and ensure its success. We mentor and coach the virtual assistant to be the best version of themselves with each of their clients. We provide a custom onboarding experience for our clients, complete with resources and guides to become better delegators and leaders.

Our support has helped hundreds of entrepreneurs become empowered leaders, better delegators, and more successful business owners.

What quality or characteristic do you feel is most important to your success?
I believe that purpose-fulfilled people change the world, and I believe that my devotion to creating space for others to find that purpose and joy in their work has been critical to our success so far.

The quality that is at the heart of my success is trust. The name “Trusty Oak” was inspired by a book by Stephen M. R. Covey called The Speed of Trust. Covey says that trust is the currency of relationships and when we are intentional about increasing trust in our relationships, the cost of doing business goes down and speed goes up. I have found this to be true and a powerful contributor to our rapid growth and the overall ability to scale.

I am constantly looking for opportunities to delegate tasks and decisions as a way to free up more of my own time to do more of what I am great at and love, but it serves another purpose, too. Delegating effectively (and often!) increases trust within a team and empowers others to demonstrate accountability for outcomes that serve everyone involved instead of just one or two individuals at the top.


  • 90-Day Trial: $1,369 (Required starting package)
  • Acorn: $390/month (10 hour plan)
  • Sprout: $760/month (20 hour plan)
  • Oak: $1,480/month (40 hour plan)
  • Grove: $2,160/month (60 hour plan)

Contact Info:

Image Credits
Felicia Reed Photography

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