Believe It or Not, This Cover Letter Got Me an Interview


I have been a student and a teacher of making compelling, persuasive pitches. Nothing big is a solo job. Whether you have to convince someone to take a job, give you a job, offer or invest their hard-earned money, approve of plans, or adopt big change, you ultimately have to make a pitch.

At some point during my second startup journey when I was deep into learning about angel investors and venture capitalists, I heard a story about an unlikely recipient of huge Series A funding. It was unlikely because of the unconventional way the founder convinced investors to fund his idea. I wish I could remember the founder’s name and company. (If you know it, or a story like it, feel free to share!)

It’s popular advice to think of why an investor would not want to invest and nullify those points, but it’s quite another thing to start a pitch with “Why not to invest in me.”  That’s what the hero of the story above did, and what I finally tried and found, too, that it worked!

A word of warning: This won’t work with all audiences. It most likely works best with progressive rebels, disruptors, and other unconventionals/non-traditionals. AND: The reasons to [fill in the blank] have to outweigh the reasons not to.

Some background:

Some of you know from this blog series that I had a rough spring healthwise, and a scary spring and summer financially as a result of not being able to work for 2 months. It took me a while to get back up to full-steam with my energy and my business. It was an awakening and I realized that I ought to look into various other streams of income to avoid being made or broken by an ill-timed illness.

At the same time, a brewery was opening down the street from me – walking distance. I met the owner at a local breakfast event. He was quite busy with the opening, but I kept in touch, and of course, visited multiple times. On opening night I offered to organize an event for a group of fellow beer lovers who were quite attached to a local brewery that closed down (and each other.) I learned by speaking with him that they were hiring a part-time events manager. I let him know that I wanted to apply and he introduced me to his COO who was handling all hiring.

Though there were a lot of things to consider about accepting a role where I would be busy weeknights and weekends, I was very enthusiastic about the company, the owner, future plans, the proximity to my house, and the buzz in the community. I was already organizing an event for them – 2 in fact. I found myself visualizing all of the fun things I would want to make happen and all the people I could bring together. I thought it would be a lot of fun, but it would take something to make it work. I had wanted to see if the “reverse sell” approach that worked for the founder would work in a cover letter, but I wouldn’t dare use my clients as a guinea pig for this experiment. Plus, I have a résumé (if you can imagine) but it’s much more geared toward people and leadership than events. This was a great opportunity to see if a reverse sell cover letter would work, and it served as a way to include a plethora of relevant experience missing from my résumé.

Though I pegged the owner and COO as relatively conservative, I also saw them as trailblazers and risk takers. I was a LOT edgier than I would normally be; I even cursed, which I would not advise!

To my pleasant surprise, I was invited to do a phone interview, which happened just before the events I organized.

Below is the cover letter with recipient information changed.

Ultimately, the job went to someone else. The cover letter didn’t get me the job, but it did get an interview, which is its job. The experiment was successful.

Please use good judgment if you decide to try your own experiment. It’s successful experiments like this that challenge the “always” and “never” advice that is dangerously rampant. If you’re ALWAYS doing what everyone else does, you’ll NEVER stand out. Part of being a leader is knowing when to deviate from the norm and trust your instincts.

“Fortune favors the bold.”

Karen Huller, author of Laser-sharp Career Focus: Pinpoint your Purpose and Passion in 30 Days (, is founder of Epic Careering, a corporate consulting and career management firm specializing in executive branding and conscious culture, as well as JoMo Rising, LLC, a workflow gamification company that turns work into productive play. 

While the bulk of her 20 years of professional experience has been within the recruiting and employment industry, her publications, presentations, and coaching also draw from experience in personal development, performance, broadcasting, marketing, and sales. 

Karen was one of the first LinkedIn trainers and is known widely for her ability to identify and develop new trends in hiring and careering. She is a Certified Professional Résumé Writer, Certified Career Transition Consultant, and Certified Clinical Hypnotherapist with a Bachelor of Art in Communication Studies and Theater from Ursinus College and a minor in Creative Writing. Her blog was recognized as a top 100 career blog worldwide by Feedspot. 

She is an Adjunct Professor in Cabrini University’s Communications Department and previously was an Adjunct Professor of Career Management and Professional Development at Drexel University’s LeBow College of Business  She is also an Instructor for the Young Entrepreneurs Academy where her students won the 2018 national competition and were named America’s Next Top Young Entrepreneurs.

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