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I recently returned from a trip to Baltimore where Michelle Thimesch and I met with several potential investors for Opportunity Main Street, our place-based investment fund.

I love the process of raising money for my own business because I always learn so much that I can use to benefit my clients! I started helping entrepreneurs raise capital over 16 years ago and this is my fifth time raising money from investors. I have raised over $2 million from a total of over 150 investors, with check sizes ranging from $1,000 to $100,000.

Here are three insights I wanted to share from my previous and current fundraising efforts:

1. Investors can come out of nowhere. Sometimes the people that end up investing are not who you expected! We met with someone in Baltimore and didn’t even “pitch her” but she ended up letting us know she wanted to invest. The lesson from this: tell everyone (without violating the law!) that you are raising money – don’t limit your asks to the usual suspects.

2. The timing is not in your control. We have had several potential investors tell us they planned to invest and we celebrated, only to be reminded that a verbal commitment doesn’t always mean an immediate check in the mail. Unexpected events like illness, bureaucracy, financial setbacks, and many more can slow the process way down. The lesson from this: be patient and persistent.

3. Investors’ motivations are complex and incredibly diverse. Some of our investors are interested solely in our mission and asset class and are happy to be passive, while others are motivated by a desire to get involved by supporting the entrepreneurs we work with. The lesson from this: brainstorm a list of all the potential benefits an investor can receive from investing in your venture – financial, educational, connections, community . . . – and know that each one of these benefits may be what motivates someone to say yes.

For details on our current fundraising efforts, please visit