I recently had an email exchange with Chris in California who asked me about my life before I started doing private investment deals. His question sparked some memories and stories I thought would be useful to share here. https://youtu.be/uyJP7yb70hE
From Yellow Pages to Entrepreneurship
After finishing university, I began my career in outside sales with the Yellow Pages. Eventually, I left and started a small business with a friend, which I ran for nearly two years before selling.
After that, I became a commercial debt broker. I took a training seminar in Toronto with a California company called The Loan Consultants. They taught me how to:
Package loan applications properly,
Structure equipment leases (both capital and operating),
Prepare commercial mortgage applications, and
Arrange factoring facilities (selling receivables for immediate cash).
That training gave me the technical foundation to step into the world of financing.
How I Marketed My Services
This was 2005, and while I used the internet, I didn’t leverage it the way I do today. Instead, I created a mailing list—yes, actual postal mail!—and targeted financial planners, commercial bankers, accountants, and business-focused lawyers.
Every two months, I mailed out letters highlighting deals I had completed. For example: “I helped finance kitchen equipment for a restaurant.” These success stories generated phone calls and referrals.
Why Bankers Were My Best Referral Source
Interestingly, my biggest referral source turned out to be bankers. Here’s why:
When a small business owner asked their bank for a loan and got declined, they often risked taking all their accounts—savings, mortgages, investments, business banking—to another institution.
To prevent losing the relationship, many bankers referred those clients to me. They knew I could place the deal with a leasing company or alternative lender—without threatening their other business.
A Big Misconception About Bank Loans
Most small business owners believe their banker makes the lending decision. The truth? At large national banks, loan officers are salespeople. Their job is to bring in deals, not approve them.
If a banker believes in your project, they’ll sell it “upstream” to underwriting. But if you’re disorganized, lack projections, or can’t clearly explain how the loan will improve your business, they won’t waste time fighting for your file. They have quotas to hit.
My Role as a Broker
Many clients told me they were “declined by the bank.” I’d ask, “Did you actually submit a formal application, or did the banker just say no?”
Usually, the banker had just brushed them off. In those cases, I would:
Create a professional loan package,
Include resumes, business history, cash flow projections,
Show exactly how the funds would increase revenue, reduce costs, or improve capacity, and
Demonstrate how the bank would get repaid.
About 75% of the time, I could take the same client back to the very same bank—and over half of those files ended up approved.
The difference wasn’t the business. It was a presentation.
The Lesson for Small Business Owners
Most entrepreneurs know how to run their businesses, but many don’t know how to present their case in a way that lenders can understand. That gap was my job to fill as a broker, and it taught me what lenders are really looking for.
It also gave me the confidence to later start doing my own private deals.
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