Running a business has never been simple, but the number of issues competing for an owner’s attention continues to grow. Rising costs, staffing challenges, changing customer behaviour, new technology, AI, government policies and economic uncertainty all affect the decisions we make.
Running a business has never been simple, but the number of issues competing for an owner’s attention continues to grow. Rising costs, staffing challenges, changing customer behaviour, new technology, AI, government policies and economic uncertainty all affect the decisions we make.
Business owners are expected to keep up with everything while managing employees, serving customers, watching cash flow and trying to plan for what comes next. No one has all the answers, but talking to people who deal with these realities every day can make a significant difference.
Running a business can also feel incredibly isolating. You may be surrounded by employees, clients, suppliers and professional advisors, yet still feel as though you are making the most important decisions alone. There are thousands of business owners facing similar challenges, but we rarely have an opportunity to speak honestly about them.
Sometimes, one of the most useful things a business owner can do is sit down with other business owners and talk.
Why These Conversations Matter
It is easy to believe that your problems are unique and no one else could understand the cash flow pressure, staffing concerns, difficult clients or constant balancing act between marketing, sales, operations and everything else.
Once business owners begin comparing notes, they often discover how much they have in common. The industries may be different, but the underlying pressures are frequently very similar.
One owner may be questioning whether their marketing is still working. Another may be paying for technology their team is not using. Someone else may be dealing with rising costs, an employee issue or customers who are taking longer to make decisions. Others may be trying to understand where AI belongs in their business without adding another expensive distraction.
These conversations move beyond general business advice. You hear how another owner handled a difficult situation, what they tried, what worked and what they would never do again. A comment about pricing, staffing, a supplier, a marketing decision or a software platform can change how someone else approaches an issue they have been struggling with for months.
That insight comes from experience.
What You Learn From Other Business Owners
There is no shortage of business information available through books, courses, webinars, consultants and online resources. All of these can be valuable, but they do not replace a candid conversation with someone who understands the responsibility of running a business.
Business owners share the details that do not always make it into case studies or presentations. They can tell you what happened after they changed their pricing, hired an employee, invested in new software, changed suppliers or stopped spending money on something that was no longer producing results.
You may hear about a decision that saved someone money, a mistake that cost far more than expected or a small change that made the business easier to manage. One owner’s hard-earned lesson could help another avoid months of frustration or thousands of dollars in unnecessary spending.
These conversations also provide perspective. When you are immersed in a problem, it can be difficult to see anything beyond it. Hearing how others view the situation may help you recognize options you had not considered or confirm that a decision you have been debating is worth pursuing.
Honest Conversation Without the Sales Pitches
Many business events are designed around networking, presentations or selling. Small Business Unfiltered is different.
This is a moderated roundtable discussion where business owners can talk openly about what is happening inside their businesses. There are no slides, prepared presentations or direct sales pitches. Participants are welcome to ask questions, share experiences, offer suggestions or listen until they feel comfortable contributing.
The discussion will be shaped by the people attending and the issues they bring to the table. We may talk about:
- Cash flow and rising business costs
- Marketing and sales that are not producing the expected results
- Staffing, delegation and managing people
- Technology and systems that create more work than they save
- The pressure to understand and adopt AI
- Changing customer expectations and buying behaviour
- Balancing the demands of the business with life outside of it
- Decisions, priorities and changes being carried into 2027
- What has worked, what has failed and what we have learned from both
The purpose is not to solve every issue during one session. It is to create space for practical, honest conversation among people who understand what it takes to run a business.
Who Should Attend Small Business Unfiltered?
Small Business Unfiltered is open to business owners from different industries and stages. It is particularly suited to:
- Business owners who want to share and learn from others
- Entrepreneurs looking for honest discussion without sales pitches
- Newer owners seeking perspective from those with more experience
- Established businesses re-evaluating their direction or priorities
- Owners dealing with change, uncertainty or a difficult decision
- Anyone who has recently wondered, “Is it just me, or has running a business become harder?”
You do not need to arrive with answers. Bring a question, an experience, a current challenge or simply a willingness to listen and participate.
What Will You Gain?
Every conversation will be different because the value comes from the people taking part. You may leave with:
- Fresh ideas and practical insight from other business owners
- A different perspective on an issue you have been carrying
- A better understanding of what others are experiencing
- Meaningful connections with people who understand business ownership
- Greater clarity about a decision or priority in your own business
- Reassurance that you are not the only one dealing with these pressures
Sometimes the most useful outcome is an idea you can act on immediately. Other times, it is hearing a question that helps you look at your business differently.
Join the Conversation During Small Business Week
During Small Business Week, we are opening the floor for an honest conversation about what is really happening inside our businesses.
Small Business Unfiltered is not a webinar or formal presentation. It is a moderated forum where business owners can speak openly, learn from one another and have the conversations we rarely make time for.
The session will be moderated by Debi Katsmar, CEO and Marketing Strategist at Prowl Communications. With more than 40 years in marketing and business, Debi is known for helping business owners look beyond the obvious symptoms, see what may really be getting in the way and determine where they need to focus next.
Date: Tuesday, October 20, 2026
Time: 11:30 a.m.–1:00 p.m. ET
Cost: Free to attend
Registration: Advance registration is required
There are no scripts and no sales pitches. It is simply an opportunity for business owners to talk honestly about business.
REGISTER FOR SMALL BUSINESS UNFILTERED ON EVENTBRITE
If you have ever wished you could sit down with other owners and say, “Here’s what is really going on,” this is your opportunity.
Pull up a chair. Let’s talk—unfiltered.
