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The Journey of Navigating a Family Business as GBT's Daughter

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The Journey of Navigating a Family Business as GBT's Daughter

Do you ever have moments when decisions are made, knowing they will impact your life forever? For you, it may have been a good decision or a wrong decision, but at the end of the day, it wasn't even a decision you made.

Welcome to my world!


Last June, my dad made a decision that would impact the rest of our entire family's life.

He decided to open his own business.

If we were to poll the entire family, trust me when I tell you, it would have been a bag of mixed results—some excitement, some reservations, and of course, some fear.

Immediately Excited By His Decision

This would give him and our family many new opportunities. I knew that he wasn't happy at the job he was currently at and was frustrated with the “agency” lifestyle.

I knew my dad and believed he could create something better/different. I saw his eyes light up when he talked about the potential of running his own business and serving the HubSpot community he had been helping for years.

The same community that had been helping him along the way.

So the simple answer to the question is I was excited about his decision. However, little did I know this would allow our entire family to do things we love.

Yes, you read that right. 

Everyone in our family is an employee of George, my dad 

Crazy, I know…

First, we have mamma bear (Kelly), who helps with project management and billing. Plus, my brothers Seth and Noah help with video and HubHeroes podcast editing for the GBT and client's content.

Then there's my older sister, Maddy, who oversees social media efforts for the GBT and HubHeroes brands.

And finally, there's me! I’m Kayle Thomas, and I’m working hard on becoming a writer, content creator, strategist … and a better daughter. 

Surprise! It's been a very interesting journey. 


Yes, There are Struggles, Arguments, and Emotions

Of course, mixing family and business together is bound to be a sticky situation, no matter how hard you work to avoid any friction. So yes, when work is involved, it isn’t always rainbows and sunshine here at the Thomas household.

For me, personally, navigating a father sometimes can be hard enough – but imagine navigating a father who is also your boss. 

Can we get real for a second?

Have you ever hungered for validation in your personal life from a parent? Have you ever desired the professional validation of doing a job right? If you have a pulse, you probably answered yes to both of those questions. It’s totally natural to want the gold stars of approval from your parents – you want them to be proud of you! 

In my case, this deep desire of mine for validation has gotten us into some professional and personal disagreements through working together. 

There’s one instance I remember vividly. I felt overlooked during a discussion and wanted to feel seen as a valuable asset in what we were trying to create together as a family. I struggled to want to be needed and seen as an indispensable team member.

I knew I had to make a decision. I could either stay quiet and swallow my pride or face a difficult conversation hoping for a positive change. I chose to sit down and have an honest conversation with my dad, Mr. George B Thomas, and talk about my concerns. 

I didn't want to ruin our father-daughter relationship over business.

I was highly uneasy going into our conversation. Imagine wanting to change something professionally but not wanting to change something personally and realizing it all had to do with the same human. #TheStruggleIsReal 

But good, open, honest communication is one of the most important things when working with your family, especially when they're in many parts of your life.

Wake up in the morning; your family is there.

Go to the kitchen, and guess what; your family is there. 

Go to bed at night and … sure, they’re not in the same room, but your family is still there. 

I didn’t even book a meeting. I just walked into his office one morning.

Maybe that was the wrong move, but with my nerves the way they were, I just jumped into the conversation. As I walked through the office door, I tried to put on my “employee” hat and asked him to put on his “boss” hat vs. his “dad” hat.

I told him I felt I was undervalued and underutilized and that I had the skills and potential to offer the family business. 

Yes, it initially felt a little awkward to just … say all of that out loud. During the short conversation, I had emotions of hope, frustration, and maybe even anger, but we pushed through.  

The good news is that my dad understood why I felt that way. As it turns out, he didn’t see me as lacking value; he was just busy being a new business owner. 

We realized he needed more time to review large tasks for me, and we needed way more communication throughout the day. 

We discussed an ongoing plan of how I could contribute more to the business that was something we both could agree with and stick to moving forward.

Now don't get me wrong, there have been messy fights! 

We’re a family, duh.

But, at the end of the day, we always come together as a family, committed to figuring things out, even when it’s a big and messy challenge where we struggle to agree sometimes.  I'm unsure if that's a unique situation, but it feels like it. 

Setting Healthy Boundaries and Finding My Identity

Do you struggle with setting boundaries in your life? In the Thomas household, this is a big challenge for us. We’re trying our best, of course, but it’s a work in progress, for sure.

It doesn’t matter if you work with your family like I do or work for someone else – you must have a clear separation between your personal and professional life.

On one side, you have the personal bucket. On the other side, you have the professional bucket. And all the while, as things fly into your life, you have to figure out which bucket to put them in quickly. While this type of compartmentalizing is challenging, it's worth it. 

Another thing I've learned is how important it is to find my own identity within the business. Working for George B. Thomas does not mean I must be George B. Thomas.

I’m Kayle Thomas. Like George, I’m also a unique individual — or, as he likes to say “whole-ass human.” So, I've had to find my passions and strengths that align with my personal goals and embrace my individuality, even though I’m working within a brand centered around another person. 

I get to bring a fresh perspective and new ideas that then complement or complete my dad's vision. 

Versus fighting for a spot that is already filled or will never exist.

It's Hard to Be GBT’s Daughter 

My dad is a great father. He has also achieved amazing personal milestones.

As his daughter, I look up to him. And the fact that I want to achieve great things just like he has (in my own way, of course) isn't far-fetched. But, one major challenge that has come with that mindset is that he's been doing this for years, and I've only been doing this for months. 

I understand my personal greatness will take time. 

I have also realized that I’ll have different results than him based on the different journey that I’m on.

Every employee looks up to a good boss, and every daughter looks up to a good dad, and mixing the two has proven to be challenging. My goal was to be the next George B. Thomas, but now my goal is just to be Kayle Thomas.

Separating my personal goals from my professional goals has been hard as well. I want to make my dad proud, so my path is discovering what I love to do and doubling down on getting great at it.

How many people can say that their dad is their boss? 

How many can say they have this opportunity that I and my family members have? My guess is not many. That's why I will never take the opportunity for granted. With the struggles come the benefits.

I get paid time off for family vacations because they're with my dad. I don't have to have awkward time-off conversations because I just let him know. I walk 10 feet to his office and knock on his door if something comes up.

Working for him, I've done five different job roles, and I would never have gained that experience in any other place. I also don't think I would've found my passion anywhere else.

Our relationship as father and daughter has grown so much.

We talk more than ever, both personally and professionally. We understand each other at a deeper level and have better communication because of this family journey.

I have so much more respect for what he does, and now I understand his nerdiness that I once used to make fun of. We have grown to love some of the same things but also get to be separate people that complement each other. I think I can say the same for the rest of my family. 

We have all learned to become like one messy yet yummy peanut butter and jelly sandwich.Working for my dad has provided me with many unique opportunities that I’m thankful for. I've learned from his expertise and experience and gained invaluable knowledge I wouldn't have access to elsewhere. 

That knowledge will forever benefit me.

Navigating working for my dad has been a learning experience for everyone. Still, it has taught me resilience, adaptability, and the importance of maintaining a healthy work and family balance. 

Something that my dad has been working on for years and, if asked, will say he is still working on it. 

Thanks, Dad, I Mean Boss, I Mean…

There have been moments of tension and disagreements, but the feeling that comes from building something together as a family is worth every moment.

My dad has been a fantastic father and is now a great boss. Or at least he's working on it. As we continue this journey, I'm excited to see where the business will go and how each one of us will evolve.

Here's to the future and what it may bring for our family … as well as the business we’re building together along the way.