Interested in starting your own entrepreneurial journey but unsure what to expect? Then read up on our interview with Amber Gray, Founder of Trusty Oak, located in Austin, TX, USA.

What's your business, and who are your customers?

Trusty Oak is a virtual assistant agency that serves US-based freelance VAs, SMB owners, and leaders by vetting, matching, and supporting these important partnerships. Small business owners who need a virtual assistant can work with Trusty Oak to find and hire the ideal VA for their needs and for as few as 10 hours per month. Virtual assistants who want to freelance but do not want to do it alone benefit from working with Trusty Oak because we provide structure and proven processes, community with other VAs, and mentorship. It's a win-win for both sides. Trusty Oak has the privilege of providing accountability and ongoing support to these entrepreneurs.

Tell us about yourself

Our entire brand is a direct reflection of my own core values, including to "keep growing." I have personally emphasized growing as an individual via both personal and professional development. In our organization, we require this growth mindset for each of our employees, contractors, and even clients. I challenge those I work with to dream big and pursue ambitious goals. I feel that I have a God-given gift to make connections, which results in a collaborative ecosystem that we can all contribute to and benefit from. That ability to facilitate meaningful connection applies to processes, relationships, and resources – all of which work collaboratively to create a ripple effect.

This has influenced growth and success for Trusty Oak by creating meaningful, balanced work opportunities for hundreds of small business owners and freelancers. Families have more time together. Adventurous individuals have more opportunities to travel and learn through unique experiences. Team members, virtual assistants, and clients of Trusty Oak have greater opportunities to achieve financial independence.

What's your biggest accomplishment as a business owner?

I am proud of how my leadership style has created a unique company culture of mentorship and authenticity and how it provides psychological safety for our team. I believe purpose-fulfilled people change the world, and we all are closer to our potential when we have autonomy and feel safe to be our whole selves. Too many people have jobs they don't enjoy, and our team regularly celebrates how lucky we all are to love our work and see that we are truly making a positive impact on the world.

What's one of the hardest things that come with being a business owner?

For me, one of the hardest things I face regularly is keeping my self-doubts in check. We all have that inner critic telling us what is not possible and when we are running a business, that voice seems to come up even more often. So many people depend on my ability to follow through on my commitments, make the right choices, and overall be successful. It feels like a lot on my shoulders sometimes, but that also makes everything I do through this business even that much more rewarding.

What are the top tips you'd give to anyone looking to start, run and grow a business today?

The number one piece of advice I offer to those considering starting their own company is to address personal debt as early as possible to allow yourself more flexibility to take risks. Starting your own business nearly always means working without a paycheck for some period of time, so it's important to reduce your debt and cost of living until you can earn what you need for the lifestyle you want.

For women pursuing leadership roles of any kind – surround yourself with people who will encourage you and believe in you, and avoid spending much time at all with people who don't see your potential. A voice in your ear along the way can make or break you.

Learn to delegate effectively. As leaders, we are high achievers doing all of the things! You will grow faster if you can practice delegating early in your journey.

Where can people find you and your business?


If you like what you've read here and have your own story as a solo or small business entrepreneur that you'd like to share, then please answer these interview questions. We'd love to feature your journey on these pages.

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