Interview with Business Humorist Hesh Reinfeld

Hesh Reinfeld is a business humorist. His humor columns are syndicated and published in a long list of publications. We’ve published one of his humor columns nearby.

Hesh is an example of the new breed of Baby Boomer entrepreneurs, who build new businesses after having held successful careers. Often this group draws upon their past experience and knowledge, and it’s precisely because they have had those experiences that they feel qualified at this stage in their lives to strike out on their own.

Hesh’s website gives this background about him:

My problem was that I was always the one cracking a joke and getting one of those looks from my boss. You know the one. It says, “Hesh this is serious stuff. You can’t joke about it, even though we all know how boring the meeting really is.”

Whether at a replacement window manufacturer or a biotech start-up, I found the same behavior. The only difference was that people used a slightly different vocabulary.

My column, with its skewed perspective on business, got its start with the readers of the Central New York Business Journal (Syracuse). And they liked it. Over time, additional publications and web sites continue to sign me on and carry my column. I even went international when the Bermudian Business started publishing my columns.

Recently I had the chance to interview Hesh to understand what it is like to be an entrepreneur making your living as a business humorist. Here is his story, in nine questions or less.

Q: What’s a typical day like in the life of a business humorist?

A: The reality is that I spend most of my time making sales calls. I am on the phone or sending e-mails to editors trying to sell my columns. I spend about 80% of my time doing marketing and sales and 20% writing.

Q: Is there a particular way you get inspiration for your writing? Do you skim newspapers, or meditate, or???

A: I force myself to sit in front of my computer. I go through notes and ideas I have jotted down. I am trying to get my brain into a story telling mode.

Once I have a working theme, it becomes a jigsaw puzzle. I have to put all the pieces together and use only 700 words. I usually get 90% of the story done and then I get stuck on an ending. I find it most useful to just walk away from the story and go shopping, eat dinner, etc. Then an ending will come to me and I run upstairs to my computer to get the words out of me.

Q: Tell us about your own entrepreneurial journey. Did you have to deal with a lot of naysayers, who said you’d never be able to make money at what you do? If so, what was your response? Would you do it all over again? Do it sooner?

A: At first I just wanted to get published. Then a local editor told me I had some promise but the real issue was the ability to produce a column week after week. So I kept on writing. I did have one ex-editor tell me that my stuff was not that good. I just decided not to talk to him for a while.

I did not know what I was getting into. I think if I would have taken a totally rational approach, i.e. done some serious market research, I would have told myself that the barriers to entry were too high.

Would I do it over again? Yes, but I wish I had started 20 years ago. But then 20 years ago I did not have the experiences under my belt.

Q: In your nearby humor piece about the entrepreneur, you sound familiar with the buzzwords that venture capitalists use. Is that because you have had experience raising money or as a VC?

A: I have worked in many different businesses from selling technical training programs to engineers to putting together a real biotech deal. So I just know enough to use the right buzz words.

Q: What is your business model?

A: I focus, focus, focus. I produce content for publications (print, web, radio) that want to connect with business people. Although I write funny stuff (I hope) I am very serious about my business. I help publications differentiate themselves from their competitors by offering a ‘dash’ of humor.

Q: Where are your columns syndicated?

A: My columns are syndicated through B2B publications either weeklies or monthlies. Currently my column is available in Syracuse, Las Vegas, Pittsburgh, Southeastern Florida, St. Louis. Kentucky, New Hampshire. Internationally my column is read in Bermuda, Australia, and I even got into a paper in Taiwan.

Q: What is the typical profile of your reader (or whom do you typically write for as a target audience)?

A: My reader is usually a small business owner. The letters I get say that they have faced similar concerns. So even though I actually write fiction, my work touches real business people; perhaps even more than all the “how to” books and articles.

Q: How would you describe yourself?

A: I have a wife who is ready to retire, 3 children, who are just about grown, and a mom who unfortunately is living with alzheimers. I volunteer twice a week running discussion groups for men in senior citizen buildings. I discuss my business problems with them. They are my true mentors.

Q: Is there anything else I haven’t asked that you would like readers to know?

A: For 25 years I sat through business meetings and would ask myself, “how come no one else is laughing?” Then I realized that most people were but were just afraid of being the first one to crack a smile.

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