4 Key Lessons I’ve Learned From Entrepreneurship

Richard Grier • July 2, 2025

"Small stacks make large stacks." - Tommy Kessinger said to me.



As I look back on my journey as an entrepreneur, I realize how much I’ve learned along the way. But this journey, like many others, started with a serious concern: as a pastor for many years, there wasn’t a lot of extra, so Katie—my wife—and I had very little in savings.


This concern was eating at me when my partners and I were starting Hard Hat Housing, and I shared it many times with my close friend, Tommy, but each time he replied with the same thing: “Small stacks make large stacks.”


This quote obviously applies to money and investing, but it also applies to building a business. And today, I want to share more of what I’ve learned in the past few years on this journey.




1. Flexibility Is Your Best Friend

flexible pencil

I learned early on that flexibility is everything. Construction projects rarely go as planned. Maybe the project timeline shifts, or the number of workers suddenly increases, which in turn, affects construction crews housing.


However, the issue we faced early on, was when a Superintendent called us, very late, on a really hot day to say that the air conditioning was out in a house we rented to the crew.


The HVAC failing that late left us scrambling for a solution.


We had to quickly fix this, so we booked them a nice hotel for a couple of nights, and treated them to dinner, while we worked on fixing the HVAC. And within only two hours, a HVAC specialist got to the house and fixed it.


The flexibility in our approach meant that we could handle unexpected challenges without sacrificing the quality of housing we provided. But flexibility wasn’t the only thing that saved us.




2. Communication Keeps Everything on Track

communication

Here’s a big one—clear communication. Whether it’s between my team, our clients, or the workers themselves, if everyone’s not on the same page, things can quickly go sideways. I’ve learned that checking in, setting expectations, and being transparent is crucial.


And communication was one of the key factors in this experience. Had the Super not shared the issue with us so quickly, we wouldn’t have been able to have the specialist inspect it until the next day. But the other thing is, communication wouldn’t work, unless you have someone to communicate with, meaning you have to:




3. Build Strong Relationships With Everyone Involved

build relationships

Construction housing is a collaborative effort in nature. Over the years, I’ve realized the importance of building strong relationships—not just with clients, but with housing partners, and even the workers. The stronger these relationships are, the easier it is to solve problems when they come up.


These strong relationships were one of the main reasons we were able to handle this situation, because our client success manager really works at developing trust with our housing partners and the staff using the house, and because we had a great relationship with the HVAC specialist. That connection really sped up the situation and allowed us to get things solved much more quickly.




4. Lead With Integrity, Always

leadership integrity

Finally, one of the biggest lessons I’ve learned is the importance of integrity. When you lead with honesty and transparency, you build trust with your team, clients, and partners. I’ve seen firsthand how much smoother things go when everyone knows you’re operating with integrity.


And it shows in this example—we didn’t blame or make excuses. Something went wrong at our property, and we just offered solutions and people to help and things flowed well. We honestly told the crew that it might be a few nights in a hotel, instead of promising just one, but thankfully, it was only one night, and we didn’t have to break our promise. Moreover, the HVAC Specialist was fair in their work as well, because of years of building trust with them.





It’s been 2 years since that project, and 2 ½ years since we started Hard Hat Housing and since then I've been learning more and more lessons about entrepreneurship. 


To many of you, these “lessons” may not be new, but they are things that can easily slip out of someone’s mind; one might think, “I don’t want to bother my client with this issue, I will fix it anyway”, but the issue may get to your client before you have the chance to fix it, and communication in this case is your best friend. 

 

The past 2 ½ years have taught me a lot about managing construction housing, and managing a business in general, but at the core of it all are these 4 lessons: flexibility, communication, relationships, and integrity. These lessons have helped our team grow Hard Hat Housing and overcome many of the challenges that come with running a business in this industry.


Small stacks make large stacks. It’s doing the little things the right way that build something bigger and bigger.


What lessons have you learned along the way? I’d love to hear your thoughts. Drop a comment below and share your experiences with leadership and managing teams.


By Carrie Mink July 4, 2025
Discover why renting to construction crews is the smarter, stress-free choice for homeowners—and how Hard Hat Housing helps build the bigger picture.
By Rana Hazem July 1, 2025
Discover what construction workers really need in temporary accommodation—from comfort and rest to respect and connection.
worker and family in a hotel room
June 11, 2025
Explore how midterm rentals enhance comfort and cost savings for construction crews. Discover why Hard Hat Housing is the ideal choice.
construction crew living
June 11, 2025
Discover how workforce housing apartments improve crew living conditions and streamline property management for construction companies with Hard Hat Housing.
construction worker
June 11, 2025
Discover how Hard Hat Housing's midterm rentals offer construction crews comfort and savings over extended hotels, enhancing morale and productivity.
midterm rental
June 11, 2025
Transform unused spaces into income by hosting construction crews. Ensure property upkeep with Hard Hat Housing's tenant care and management services.
June 3, 2025
Discover how optimizing crew housing boosts efficiency, satisfaction, and project success. Explore tailored solutions for your construction team's needs.
June 2, 2025
Discover how Hard Hat Housing enhances crew productivity with convenient temporary stay apartments, offering comfort, flexibility, and job site proximity.
June 2, 2025
Discover how workforce housing apartments boost construction crew productivity, with Hard Hat Housing's expert guidance and tailored accommodations.
May 28, 2025
Discover how low-cost housing enhances construction budgets, boosts productivity, and improves crew well-being with solutions from Hard Hat Housing.
More Posts