How to Write to Your Investors, Stakeholders, and Biggest Champions

You’re reading an excerpt of Great Founders Write, by Ben Putano, writer, entrepreneur, and book publisher. He’s the founder of Damn Gravity Media, a publishing house that inspires and educates tomorrow’s great founders. Purchase now for lifetime access to the book and on-demand video course.

Mac Conwell is a developer, two-time startup founder, and venture capitalist. In 2020 he started Rarebreed Ventures, a pre-seed fund focused on underrepresented founders—female founders, minority founders, and founders living outside the main startup hubs in the US.

For all of Mac’s skills as a developer and capital allocator, his greatest strength (in my opinion) is his storytelling. As we discussed the importance of founder-investor communications, he shared this story:

“When I worked for the state of Maryland venture fund, we had a high-flying startup who had just landed a major distribution deal. Things were going great, but then we didn’t hear from them for a while. I went about my business, working other deals and such. Then one day I got an email from one of the co-founders.”

Mac seemed visibly shaken at this moment, as if he was reliving the experience while telling me the story. For an investor, surprise emails are about as welcome as kidney stones.

The email said, “Hey Mac, just thought you should know. Our CEO took another job at a marketing agency. Also, we’re out of money.”

“Just thought I should know?” Mac asked rhetorically. “Um, yeah, I think I should know!”

Mac called the co-founder within minutes of receiving the email. Apparently the company blew their budget on R&D and didn’t have enough money for production. Mac helped them acquire new capital to temporarily salvage the situation, but they continued to fall into debt and eventually went under.

“Because they spent so much time trying to solve the problem themselves, by the time they told me about it, I could no longer help them,” said Mac.

As a founder, people are betting on you to be smart and resourceful. So when a problem arises, it’s tempting to keep it quiet and try to solve it on your own. Sometimes you will, but it could also cost you your company.

Mac then shared another story with me, this time about one of his portfolio founders whose communication skills saved the company, and potentially much more.

The founder was an immigrant living in the US. One day he was met at his home by ICE agents and was taken into custody. There was a misunderstanding about his immigration status. The founder called Mac immediately:

“Hey Mac, I’m being taken away right now. Just wanted you to hear it from me and not my co-founder.”

Then he hung up.

It was a Friday. Mac had planned on a quiet weekend of work and rest, but plans had changed. He dropped everything and started making calls. Mac found a better lawyer for the founder, and they were able to clear up the confusion. The founder was released and the matter resolved by the end of the weekend.

“Had he waited to call me until Monday, the situation would’ve been completely different,” said Mac.

If you find the right investors, they will do whatever they can to help you succeed. But they aren’t mind readers. Frequent, honest communication is the foundation of a beneficial founder-investor relationship.