Most advice for small business owners comes from people who have only observed entrepreneurship. But when you’ve actually signed the lease and watched your bank account dip lower than you’d like, the lessons hit differently. These are the insights I learned the hard way—first as a lender, then as a business owner navigating one of the most unpredictable economic periods in modern history.
1. Expect the Unexpected
When I opened my business in 2019, I thought I had planned for everything—competition, seasonality, staffing, cash flow. What I didn’t plan for was a global pandemic shutting down the world just a few months later. That experience taught me a lesson every business owner eventually learns: uncertainty isn’t an exception; it’s the rule.
Takeaways
- Build a real cash reserve. Not a “leftover money” reserve, an intentional, protected buffer. Aim for enough to cover several months of operating expenses.
- Stress test your business model. Ask yourself: What happens if revenue drops 30%? What if supply costs spike? What if you lose your biggest client?
- Stay flexible. The businesses that survived COVID weren’t the biggest; they were the ones that could pivot quickly.
Planning for uncertainty isn’t pessimism. It’s responsible leadership.
2. Read and Understand Every Detail of Your Lease
Your lease is one of the most expensive and binding commitments you’ll ever make as a business owner. And yet, most people skim it like it’s a software update agreement.
I learned this the hard way. There were clauses buried in the fine print like maintenance responsibilities, rent escalations, and signage restrictions. I didn’t fully understand them until they cost me money.
Takeaways
- Small clauses can have big financial consequences. Have a lender, attorney, or trusted advisor review your lease before you sign.
- Landlords often use standard language that benefits them, not you. Ask questions until you understand every line.
- Negotiate more than you think you can. Leases are rarely “take it or leave it.”
A lease isn’t just paperwork. It affects your ability to grow, relocate, or even sell your business.
3. Treat Your Landlord Like a Business Partner
Most business owners treat their landlord as a bill they pay once a month. But the truth is, your landlord can be one of your most valuable allies.
During COVID, the businesses that survived often had landlords who were willing to negotiate, defer payments, or offer temporary relief. Those conversations only happened because relationships already existed.
Takeaways
- Good communication builds trust, and trust buys you flexibility. Communicate early and often, especially when challenges arise.
- Share your long-term plans so your landlord sees you as an asset, not a risk.
- Landlords talk to lenders, contractors, and other tenants. Your reputation matters. Treat them with the same professionalism you expect from them.
Business is built on relationships, and your landlord is one of the most important ones.
4. Owning vs. Leasing Commercial Real Estate
Many business owners dream of owning their building someday. It’s a smart goal but not always the right move at the beginning.
When Leasing Makes Sense
- You’re still testing your business model.
- You need flexibility to grow or relocate.
- You want to preserve cash for operations.
When Owning Makes Sense
- You have stable revenue and long-term plans.
- You want to build equity instead of paying rent.
- You’re ready for the responsibilities of property ownership.
As a lender, I’ve seen both paths work beautifully and both paths go wrong. The key is aligning your real estate decision with your business stage, not your ego.
5. It’s All About Relationships
If there’s one theme that ties all these lessons together, it’s this: relationships are everything.
Your landlord.
Your lender.
Your vendors.
Your customers.
Your community.
The stronger your relationships, the more resilient your business becomes.
Takeaways
- Build relationships before you need them.
- Stay transparent with the people who support your business.
- Invest in building trust with people. It pays the highest long-term dividends.
When times get tough, it’s not your business plan that saves you. It’s your people.
