01
What the Midterms Reminded Me About Leadership
The 2026 midterms offer a leadership lesson for business owners: big promises create expectations, but consistent action earns trust.
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People & Systems
Lessons on leadership, culture, accountability, and building systems that let a company grow.
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02
Why Your Team Fails: And Why It’s Your Fault
If you've ever built a business—especially in the trades—you know this feeling: the crushing pressure of systems that don’t scale, people who mean well but fall short, and the quiet, gnawing question in the back of your mind: Is this even…
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Rethinking My Highest and Best Use
Each Saturday, I take a step back from the daily grind—revenue, meetings, code, strategy—and ask a more important question: What is my highest and best use?
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My Company’s Doubling: And I Can’t Be in the Way
Today was a turning point. Not because something broke—but because something is finally starting to bend the way it should.
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I’m Not Leaving Canada: But I’m Building Life Somewhere Else
Today I took another step toward spending more time outside of Canada. It’s not a full exit—but it is a full decision.
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A Mexican Moved to Canada for a Better Life. I’m Leaving Canada for the Same Reason.
Today I felt something I haven’t felt in a while: conflicted . We just onboarded a new teammate—an incredibly capable accountant from Mexico who moved to Canada two years ago with his wife and three kids in search of a better life.
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I Built My Own Software, Rebuilt My Team, and Canada’s Still a Mess
Let’s get this out of the way: Yes, I built custom software for my company. Yes, I ditched Buildertrend. Yes, I’m still building a business that doesn’t require me to hover over it every day.
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I Just Incorporated in the U.S.: And Gave Away My House
Today marks a huge milestone. After weeks (really, years) of weighing the pros and cons of staying in Canada versus starting fresh in the U.
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dylan's updates April 26 2022
Tune in today as Dylan goes through his recent tweets about: - limited time, limited resources - getting the *right* people on your team - competing on price Twitter: @dylangallagher Connect with dylan on LinkedIn at: https://www.
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When it seems impossible.
Not every day is awesome. Depending on where you are in your journey as an entrepreneur you might find that most days are tougher than others.
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No more lines of credit says Wells Fargo. Expect the unexpected.
Nothing is guaranteed in life. Being responsible for an active business that is relied upon by customers, vendors and employees alike means being ready for anything.
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Cut your losses so you can win
Uncertainty can create chaos but it doesn’t have to. As the leader of a business you may find yourself facing uncertain outcomes in your business that no matter how hard you try, you will not be able to predict the outcome.
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Just say " I'm sorry "
You hope your business never makes a mistake. You hope your team always does the best job they can and even though they are human you hope they never make a mistake.
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Amazon might inspire your business to give back.
Taking the opportunity to give back to the community that your business is a part of doesn't take much.
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119 stores closed. Bose ends an era.
Being a leader in an industry or a market place is a good thing. Your margins can be higher than your competitors and your cost of acquiring a customer can be lower.
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Learn from your mistakes and adjust like Bed Bath & Beyond
Making mistakes is part of running a business. Coming up with ideas and goals is easy. Executing and getting your team to perform is hard while hitting targets can seem almost impossible.
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Ted Baker should have made tough decisions sooner. Should you?
No entrepreneur wants to admit defeat and failure. There is a part of every entrepreneur that needs to be optimistic about the future and carry hope for their team when circumstances seem overwhelming.
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Feeling Blue? So is JetBlue.
Some days you don't feel like going into the office. Some days you don't feel like responding to folks on your team that have questions and need direction.
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Ford has $37 billion in the bank and is being cautious. What about you?
Managing cash can be tricky for a small or medium sized business. There never seems to be enough.
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How do you make money when your price is zero?
When you compete on price you make your business vulnerable to your competitors who can simply drop their price to take your customers.
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Managing your team can be tough. Just ask Google.
Every good business depends on good people who use their skills, talents and experience to deliver products and services to customers.
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A boost of encouragement thanks to Tesla :)
Being an entrepreneur is tough. It's tough because you have to find a way to have vision and lead your team when non-entrepreneurs tell you that you are crazy.
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Want to learn how to counteract problems? Watch Airbnb's Chesky.
Being a leader means leading. Leading by example. Airbnb CEO Brian Chesky decided to counteract some challenges in his business that provides a great example of how to deal with challenges in your business.
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Even leaders get tired
Listen to the podcast here: Being an entrepreneur means it can be tough to talk out loud about the challenges you are having.
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No drama just great entrepreneurship
There was no drama. There was no systems melt down. Everything went as it should yesterday when Twitter went public.
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Entrepreneur feeling alone...help wanted
Being an entrepreneur can be a lonely place. Charged with being a leader, having answers to challenges and knowing the future are all tremendous and sometime overwhelming tasks.
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Mixed use investment property
With only 20 days to help a client purchase a small mixed use property, Royal Bank referred a deal to us as they couldn't complete their process in time to meet the deadline.
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Commercial borrowers frustrated by process
Two calls in a row this week have come in from borrowers that feel very frustrated with the lack of service being given to them from other lenders and other brokers.
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