Interested in starting your own entrepreneurial journey in coaching but unsure what to expect? Then read up on our interview with Dillan Taylor, Founder of Grindstone LLC, located in Annapolis, MD, USA.

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

I run a life coaching business under Grindstone LLC. In short: I help people get to where they want to go. What that means looks different for everyone. Building a business, creating content, deepening relationships, taking more action, prioritizing, removing distractions, etc.

As an insight coach, I don't hone in on a particular niche. The only requirement in working with me is the willingness to explore and change. I've done that with founders, engineers, comedians, politicians, coaches, teachers, and more.

I mentor coaches who want to grow their businesses in my coach-training community (the Insight Coaching Community). We focus on making more money by providing more value to our clients. In the ICC, we prioritize service first. Not selling, marketing, or social media...just genuinely making a difference in someone's life.

Tell us about yourself

My life was a mess until 2017. That spring: I failed college, the woman I thought I'd marry broke up with me, and I had to move back in with my mom with no job and no skills. On a Saturday night in June, I tried to end my life. As heavy as that sounds, it was the most important thing that's ever happened to me. It woke me up. Since then, I've been obsessed with taking ownership and building the life I want. After doing just that (starting a business, getting in shape, becoming more vulnerable), it was only natural that I felt the desire to help others do the same.

I don't have some glamorous Why or purpose. I'm just lucky to have found something that looks like work to others and feels like play to me. Helping people become more fulfilled lights me up, so it's hard not to keep coming back. For me, coaching people is the convergence of the three big questions when pursuing a career:

  • What do I really love doing?
  • What am I really good at?
  • What value can I provide that others would pay money for?

I like it, and it pays my bills. That's all I need.

What's your biggest accomplishment as a business owner?

As cheesy as it sounds, I measure my accomplishments on the accomplishments of my clients. Highlights include an aspiring coach creating a full-time practice, a real estate agent quitting his job and moving across the country to live a happier life, and an insecure teacher becoming confident and assertive with her boundaries. The list goes on. But in general, my greatest accomplishment has been seeing the impact I've had on the livelihood of the people I work with.

On the self-serving side of things, creating a business that makes $10k+/month is astonishing to me. I've never had a natural business or sales mindset. So I spent most of my life thinking I could never run a company. That was obviously just a story I was telling myself. Now I help other people squash their stories.

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

Running your own show is a gift and a curse. The best part can also be the most challenging. That part is freedom. I crave autonomy—designing my own schedule, never asking permission, and innovating on my own. But on the flip side of that, there's no one telling me what needs to get done or what to focus on next. That leads to the inevitable questions of doubt.

  • "Am I working hard enough?"
  • "What's the most important thing right now?"
  • "Am I done?"

That's why I think the most important skill as a business owner is the skill of defining. What exactly is the project I'm working on? What are all of its smallest parts when broken down? What're the next three steps?

Ambiguity can lead to a ton of resistance and confusion. But it's what I signed up for. I'd rather stress about what I'm building than over meeting someone else's expectations.

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

  1. "Work hard" is bad advice. It's much more important to know how to work effectively. What exactly are you working toward? Why? How will the next thing you do get you closer to where you want to go? 3 hours of high-quality work is always better than 10 hours of fumbling from task to task.
  2. You can't get something from nothing. There's all this talk about passive income. I think a lot of people are looking for "get rich while doing nothing" ideas. But everyone I know who has income coming in while they sleep puts in a ton of time creating that thing (e.g., software) and continues to put in time and effort innovating it. The key questions are:
    What value do I want to provide others? What problems do I want to solve?
  3. Surround yourself with creative and driven people. Starting and growing a business should be exciting. You have all the freedom in the world to make it fun. But having a network of people playing a similar game will make the journey sooo much smoother. You can: get feedback, exchange ideas, and soak up the energies of those around you. Running a business can be lonely, but it doesn't have to be.

Is there anything else you'd like to share?

I've never been a naturally business savvy person. So if I can start and grow a profitable and sustainable company, anyone can. I also have a blog to share my experiences and insights on business, relationships, and mustaches. (dills.blog)

And if anyone is looking to connect for any reason, feel free to email me: dill@dillantaylor.com.

Where can people find you and your business?

Website: https://www.dillantaylor.com/
Facebook: https://www.facebook.com/dillanroytaylor/
LinkedIn: https://www.linkedin.com/in/dillanroy/

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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