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.

The post Interview with Business Humorist Hesh Reinfeld appeared first on Small Business Trends.

Hesh and I spoke, and I found his humor to be intelligent, brilliantly incisive, and of course, funny. The following piece captures the essence of what it is like to be a serial entrepreneur.

Confessions of an Entrepreneur

By Hesh Reinfeld

I told my family that I finally accepted that my passion had become an obsession and you could even call it an addiction. They all laughed. What had taken me 25 years to recognize, they had known for years.

My wife detected my addiction as early as our honeymoon in Paris. All I wanted to do was spend time at the Bourse trading francs on the spot market. She kept on nudging me to see some old picture in the Louvre.

For my daughter it became clear when I demanded that her prom date be an officer in Junior Achievement. I thought it was a good way to ensure that she dated a young man with career aspirations. She saw it differently.

Her younger brother, the violin virtuoso, threw the matter of the addiction in my face when I told him I would not pay for his schooling at Julliard. The curriculum did not have a course in business development or even Accounting 101. How would my son know if his future agent wasn’t cookin’ the books?

It had been six months since I had read a business plan. And I missed it. I missed it real bad. I salivated when the Wall St. Journal driver came down my block… only to skip my house. My wife had a block on our cable TV- no more MSNBC and it was no better on the Internet, I couldn’t access Bloomberg.

Last Tuesday a power stronger then me won out. I don’t know how, but I ended up at the Harvard-Yale-Princeton Club. My eyes focused on the booths along the back wall. I immediately saw the signs. A shot of single-malt Scotch, half finished, was being used as a paperweight on a four-color business plan. The reader, a silver-haired executive with monogrammed reading glasses was analyzing spreadsheets as he simultaneously served volleys of staccato like questions at the young man across the table.

This young man was obviously new to the game. His dark blue suit looked like he had not worn it since his bar mitzvah, and the tie must have been knotted eight years ago and never unraveled. He had ordered the latest micro-brew, but had not taken even one sip.

I sat at the next booth and listened in. I promised myself not to say a word. All I wanted was to eavesdrop and savior the rhythms of the conversation. I smiled as I heard the two argue over, burn rates, traction projections, alpha / beta sites, and most stridently, about valuations.

A cell phone rang, and the single-malt Scotch stood and walked a few steps to take the call in private. I jumped up and got into micro-brew’s face. I told him he was under-capitalized. He was giving away his intellectual property. His burn rate was twice as fast as this so-called ‘angel’ investor was revealing. Big Pharma would pay a much higher multiple for the company if he would listen to my suggestions.

He looked bewildered. I said it again, “Don’t make the deal — you’ll lose your company to this chamber of commerce man of the year wanna-be in seven months.”

The conversation on the cell phone ended and Mister single malt Scotch asked, “Do we have a deal? ” Micro brew-looked at him, then me, and said… “No way!” He reached for his beer and slid into my booth.

I don’t have to tell you what happened next. You all know it too well. We sat for three and a half hours, re-doing spreadsheets on his laptop, and playing out various pro-formas.

I finally stumbled home, embarrassed and yet delirious with joy over the deal I had structured. My wife could see me hiding the business plan under my coat. She demanded to see my cell phone. Quickly she went through the calls I had made in the last four hours. She knew the area codes, New York, Brussels, London, and my newest haunt, New Delhi. I had been lining up angel investors.

What could I say? I had already used up my inventory of ‘I promise it will never happen again’s.’ She had been going to her own meetings and knew that she needed to go on with her life and not let my addiction manipulate her.

Had I called my sponsor? She had not seen his number in my cell phone’s call list. “No,” I whispered.

She made me return to Entrepreneurs Anonymous (EA). I had stopped going to my meetings. I had beaten it or so I thought. But the truth is, we never do. I was just like everyone else in EA. I matched the profile perfectly. 80% of members have a relapse within their first six months. I was now another data point confirming that statistic.

My next stop is the 28-day regimen at the Warren Buffett Center for Recovering Entrepreneurs at White Sulfur Springs. I wonder if they will give me my old room back. Wish me luck.

The post The Entrepreneurial Addiction appeared first on Small Business Trends.