We’re excited to introduce you to the always interesting and insightful Amber Gray. We hope you’ll enjoy our conversation with Amber below.

Amber, looking forward to hearing all of your stories today. Often outsiders look at a successful business and think it became a success overnight. Even media and especially movies love to gloss over nitty, gritty details that went into that middle phase of your business – after you started but before you got to where you are today. In our experience, overnight success is usually the result of years of hard work laying the foundation for success, but unfortunately, it’s exactly this part of the story that most of the media ignores. Can you talk to us about your scaling up story – what are some of the nitty, gritty details folks should know about?

I started my virtual assistant business out of frustration with my VP of operations job and a desire to make a more meaningful impact on the world. My goal from the beginning has been to create something that scales and provides work opportunities for as many freelance VAs as possible and to improve the success rates for small businesses everywhere. I knew I needed others to join me in doing that, but I had to start from ground zero.

I was the first virtual assistant, and especially in the first year, I networked aggressively to raise awareness of what I wanted to achieve for small businesses. Freelance VAs wanted to join in the journey, so I welcomed them in, and I applied my operational expertise toward creating processes before I even had a team.

The truth is I hustled hard for years before I even earned a decent salary. In the second year, I wasn’t sure if I would make ends meet. I was driving for rideshare companies and working part-time as an office manager in a small software development company. Those days were my most humbling. My business cards said “Founder & CEO,” but my days were spent cleaning toilets, sweeping floors, ordering office snacks for the young employees of the software agency, and driving strangers around Austin. Somewhere in the mix of that, I would complete administrative tasks for my clients, stress over payroll for the few VAs I had convinced to join me, and meet with small business owners who I hoped could be my clients one day. I sometimes felt like a fraud – wondering how others thought of me and my crazy idea that wasn’t paying the bills!

But I kept going and leaned on the community of business leaders with whom I was developing relationships for advice, encouragement, and referrals. I focused on developing business processes that were repeatable and efficient. And I delegated work to the VAs, allowing me to spend more time on business development. The good news is that I began to scale my business quickly!

I am celebrating seven years in business in August 2022, and today I have 6 full-time employees and 3 part-time employees, and we serve over 60 freelance VAs across the country. We have served hundreds of small businesses in the US (and one in Germany!) and are on track for our first ever million-dollar year this year!

I feel we are still just getting started, though, and have much more to do to reach our potential. As we’ve grown, new challenges arise, and I am constantly stretched beyond my comfort zone and am required to grow personally and professionally. It’s a journey that doesn’t get easier over time, but the rewards are worth it.

Awesome – so before we get into the rest of our questions, can you briefly introduce yourself to our readers.

I became an independent adult before I even had my high school diploma, and I never went to college. I was a pharmacy technician for 11 years before a friend talked to me about website project management, and I got interested in that and technology and marketing. I was lucky to work for a small digital marketing agency for five years and learned a lot, but I still felt I could do more. When my job search wasn’t going well after a few months, I got the idea to start a VA company.

Too many entrepreneurs are overwhelmed and trying to do it all themselves. Trusty Oak is on a mission to beat burnout and contribute to the growth of every small business through education and connection. We connect driven entrepreneurs with the best freelance virtual assistants in the U.S. so they can focus on growing their businesses instead of juggling numerous administrative tasks.

Trusty Oak’s US-based virtual assistants have support through coaching, mentoring, and community with other VAs so they can provide top-notch service through our fractional business model. Our clients can hire a dedicated VA for less than $450/month and get access to various talented assistants for anything from invoicing and client onboarding to social media marketing and content creation. We believe our success stems from our emphasis on leading with our values and caring deeply for our team and clients. Collaboration always wins!

Do you have any insights you can share related to maintaining high team morale?

This topic is one of those that I like to think we are doing well, but at the same time, it’s one of the more challenging aspects of running a company, and it stretches me every day. In my experience, it all started coming together when I got clear on our purpose and values.

I have always cared deeply for my team and have struggled with making difficult decisions to get the right folks in the right roles within the company. Letting some key players go in the past was very emotional for me, but it was always the right decision for the company’s success. When we defined our core purpose and values, it was evident that we had some misalignment on the team at one point. I lost a couple of folks, but then I was able to build the team with intention and provide a culture of accountability and trust.

Today, my team is aligned, and even in challenging circumstances, we are committed to serving each other and growing the business. As a leader, I make decisions based on my values and ask the team to do the same. It’s easier to make difficult choices if you let your values be your guide.

Stay true to your values, and don’t ruminate on your regrets. Ensure your team knows the big purpose behind your business because we all want to be a part of something bigger than ourselves and to make a positive impact on the world. Use your company to provide that purpose. After all, we spend the majority of our day at work!

Has your business ever had a near-death moment? Would you mind sharing the story?

I’ve already mentioned the humbling experience of working side jobs to support myself while building the business two and three years in. To elaborate, I almost threw in the towel during that time. I lost faith in myself and started thinking that maybe I couldn’t do it on my own. I did not have investors or any kind of funding, and I worked grueling hours to cover expenses like payroll, software, personal rent, and food!

A couple of friends approached me interested in partnering and “saving” the business, and I was in very serious conversations about taking this step. I didn’t believe I could do it alone anymore, and I was desperate to avoid hitting the kill switch. I didn’t want to admit failure and was willing to do anything to keep it going.

I have a very vivid memory of sitting across the lunch table with another friend, telling him about what I was considering. I was in tears and feeling afraid and tired. And I am forever grateful to him for putting a word of caution in my mind to slow down and evaluate what truly motivated my decision. After reflecting on my motives, I realized that it was all fear-based. I decided not to move forward with any partnership unless I could do it for the right reasons – not out of fear. Taking this pause renewed my faith in myself and my business.

I still own 100% of my business, earn a decent living, and am proud of what I have built and continue to grow. It was a close call but thanks to my supportive friend, I could think more clearly about what I wanted and who I wanted to be.

Contact Info:

• Website: https://trustyoak.com/
• Instagram: https://instagram.com/ambergrayatx
• Facebook: https://www.facebook.com/trustyoak/
• Linkedin: https://www.linkedin.com/in/ambergrayatx/
• Twitter: https://twitter.com/trustyoak
• Youtube: https://www.youtube.com/channel/UC-RxZrXptKsTwgTZblzwhyw

Image Credits
Felicia Reed Photography