We were lucky to catch up with Rob Hollingsworth recently and have shared our conversation below.
Rob, thanks for joining us, excited to have you contributing your stories and insights. Let’s kick things off with a hypothetical question – if it were up to you, what would you change about the school or education system to better prepare students for a more fulfilling life and career?
The school system is designed to feed corporate America. It is designed to create worker bees to serve larger companies. I appreciate it as a business owner, yet disagree with it. I have a Master’s degree that I do not use. The college system is largely, just an extension of the public school system. It is just much more expensive.
Creating and finding opportunity, learning to network, prepare taxes and take advantage of legal tax incentives, forming business entities, and many other things are not included in an education. Mind you, some majors at the college level do touch on some of these topics, but the public school system does not make a serious attempt at it.
In order to achieve a more fulfilling life two things are important to me: time and money. The problem is most are taught in school that in order to make more money, you need to invest more time. We are lead to believe you can’t have both.

Awesome – so before we get into the rest of our questions, can you briefly introduce yourself to our readers.
I am a Navy Veteran and former SWAT officer. I was lead to believe that in order to live a fulfilling life, I had to trade my time in exchange for more money. After serving for a decade, I realized this wasn’t true. In the communities I came from, there is a phrase:” find work”. Meaning if you are not actively doing something or contributing, find what needs to be done and fill that role.
I applied this same concept to entrepreneurship. I formed and sold my first company called The Roof Fairies, as I saw an opportunity to assist roofing contractors with insurance related jobs. This company, and my ability to network effectively lead me to start two other companies with partners. A roofing contractor called Haus Pros Roofing and Siding, and a custom Tiny Home builder called Southern Comfort Tiny Homes.
Each of these opportunities was made possible simply by networking. I am a huge proponent of the importance of building an effective network, especially for military veterans and first responders. Members of these communities do not put an emphasis on networking and when they exit the communities they are severely hampered.
Since I love to give back to these communities, I put an emphasis on training these individuals on how to start a successful business in my coaching group Plant Your Flag. In my other companies we have an emphasis on creating opportunity for these individuals to have successful careers.
How about pivoting – can you share the story of a time you’ve had to pivot?
As mentioned, I was in the military and law enforcement prior to becoming an entrepreneur. It is no surprise that those professions are very regimented, consistent, and typical in the meaning of what is a “career”. As long as you show up and do your job, you will get the same pay every two weeks.
For me, 20 more years of that was not preferred. I have always felt a deep connection with the idea that you have one life to live. Wasting it in a 9-5 (albeit a noble one of service) was no longer serving that connection.
I pivoted. I resigned, I struggled to find my new purpose or my next idea or path. Pivoting is something that is common. It does not need to be a complete pivotal shift like leaving your career to start a business. But it can be a small pivot, maybe within your particular niche. For instance, I was in the roofing sales industry and pivoted to consulting due to an opportunity that I saw.
How’d you meet your business partner?
I met one of my business partners on social media. We were both engaged in the local real estate investing market and met for coffee one time. About 2 years later, after sharing what my business was doing online and having networked within my target audience and niche, he had a need for my services. We realized that teaming up, combining our strengths, and forming a company was ideal.
Social media is free and has unlimited potential. People use it in the wrong way. You do not need to be an “influencer” or have a massive following to get free leads and make connections. If you simply share your story, your service, or what you need within your niche, leads will come.
Contact Info:
- Website: www.hausprosroofing.com, www.socotinyhomes.com, www.pyftribe.com
- Instagram: https://www.instagram.com/therobhollingsworth/
- Facebook: https://www.facebook.com/profile.php?id=100010802166751
- Linkedin: https://www.linkedin.com/in/rob-hollingsworth-922860210

