After 20-plus years of enduring increasingly diminished returns as a bottom-shelf member of the media, along with recent “downsizing” at my now-former network, I realized that it was time to stop working for other people and to start working for the man in the mirror.

Successful entrepreneurs always advise “follow your passion.” And so I did. My secret passion? I’ve always wanted to helm historical walking tours.

(Yes, shockingly, I’m also super single.)

I am a mass consumer of walking tours. Over the years, I’ve booked countless pavement-pounding adventures the minute my flight’s wheels arrive on far-away runways. And I consistently marvel at how these knowledgeable hosts hold patrons in the palm of their hands whilst dispensing all manner of amazing info within any city I’m visiting. From morbid Jack the Ripper strolls within London’s White Chapel district to sweaty Art Deco slogs down Miami Beach to a driving Dearly Departed tour (because Los Angelenos ONLY walk on red carpets) that illuminates areas where A-listers OD’ed, I log the good, bad and ugly experiences while thinking about how I might’ve made them better.

So with a mission in my heart and years of research in my head, I just had one big question: how does this industry even work?

The first step

“I think the biggest mistake people make when starting out is thinking that this is easy because it is not,” says Seth Kamil, President and Founder of Big Onion Walking Tours. There are all kinds of incorporation and insurance considerations, but before that, a biggie is defining what’s going to make your tour different.

Seth founded, what remains the gold standard in New York walkabouts, as a graduate student at Columbia University in 1991. His mission statement was two-fold: A) Churn out thought-provoking tours that focus on the history, architecture, local personalities, etc.; and B) Provide real-world experience plus much-needed income to other graduate students or recent, underfunded PhD’s which, to date, are the only types of employees he hires.

“All our guides have education backgrounds and are historians who lead tours,” adds Kamil, “not tour guides who dabble in history.”

[Note to self: Google “black-market PhD degrees”.]

“Podcasting can be a solitary business,” says Tom Meyers who, for fifteen years alongside Greg Young, has hosted the ridiculously popular, NYC-history-based-behemoth that is The Bowery Boys. “But when we’re on one of our walking tours, [an offshoot of their enterprise that began in 2018] we get to hang out with fans and sometimes get ideas from them for upcoming shows!”

“We have slightly nerdier tours, like the ‘Jane Jacobs versus Robert Moses’ walk, which I’m especially proud of because I think it taps into the DNA of our podcast,” says Meyers. “I had dreamed of that tour for years, but it wasn’t until we finally got the perfect guide, Aaron Shielke, to research and write it, that the reality happened. Today it’s one of our most popular walks and Aaron now even gives tours to city planners!”

(To know me is to know that I just had a full-on dorkgasm regarding the description of that walk.)

“This can be a dream job if you do it right,” says Randy Walker, a New Orleans-based writer who has hosted French Quarter ghost adventures, primarily through Haunted History Tours, for over a decade. “Whether the night is awful, exciting, or both, it is never boring.”

It also goes without saying that if you’re looking to entertain visitors underneath the umbrella of an established company? Make sure you know a bit about the damn company.

“Our prospective guides have to be good storytellers, obsessed with New York history, and have a sense of humor,” advises Meyers. “They also have to know the show — we don’t test them, but they do get bonus points if they point out things we said in any of our past 430 episodes!”

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Getting the word out on the street

“We were word-of-mouth, listings in print media and ‘pagers plus payphones,'” remembers Kamil. “I approached Big Onion like a business, leading tours and presenting a full walk even if only one person showed up — it cannot be all about making money in the short-term because building a dedicated client base is more important.”

The word-of-mouth thing works for me, but further afield necessities, like securing a website and dealing with eventual online anger, were worrisome.

“Those things are horrible because you have no power and one insult negates hundreds of compliments,” laments Walker of online-reprobates-masquerading-as-objective-reviewers. “I equate it to that Adam-Sandler-running-a-resort sketch when he was hosting Saturday Night Live: ‘If you’re sad now, you’ll probably feel sad there.’ Basically, Yelp was invented by angry white people.”

Adds Tom of live hecklers: “It’s quite common for passing pedestrians to add their own commentary. Greg and I were once filming something in Seward Park when a woman in her 80s interrupted the shoot yelling, ‘What do THEY know, why don’t you ask ME?!’ Of course, she was probably right.”

The name game

Regarding my business’s moniker, my long-time Compound Media graphic artist/genius, Matt Smith, kindly provided me with the below image and preliminary title, but as for a permanent name? I’m not married to Thirsty History Tours, Liver Let Die Historical Bar Crawls, Bar Apple Walking Tours, Old Brew York Tours, Pisstorical Bar Crawls or — even though blunt is usually best — Historic Big Apple Bar Crawls.

Credit: Matt Smith

None of my options moved me unless, you know, a site containing any of those words is still available. As anyone who has ever tried to name something knows, anything you really like is already taken. “We grabbed our domain name in the 1990s, so it wasn’t hard back then,” notes Kamil.

Come to think of it? I probably should’ve kept, even the crappiest of these nominees, to myself.

Making it legal (and funded)

Then there’s the getting legit bit: New York has always found new ways to fun-police any small business and my category is no different. Sightseeing guides, in all shapes or forms, must be licensed. So the most daunting requirement for this former C-student was taking the local history exam. This quiz consists of 150 questions, requiring a minimum of 97 correct answers, plus a nonrefundable $50 exam fee. (Yikes.)

“We are big advocates of the Guides Association and we only hire those who have passed the official exam,” explains Meyers. “But our guides love that test because taking it is like a night out for bar trivia!”

(Thanks for that, Tom. Doesn’t make feel even remotely more confident about this test.)

In happier paperwork news, the Alliance for Downtown New York’s Walking Tour Incubator Grant Program gives money to entrepreneurs starting walking tours in lower Manhattan. [Note: If me writing about starting a walking tour in lower Manhattan for Entrepreneur doesn’t get me a grant based on entrepreneurs starting walking tours in lower Manhattan? Well, it’s time to look into the lucrative work that is ditch digging.]

Expect the (alcohol-infused) unexpected

“I was hosting one tour on The Bowery and a man walked out of a flophouse, approached our group, dropped his pants and said to a client, ‘Will you be the mother of my children?'” recalls Kamil of a 1994 gig. “We quickly walked away with the woman being shocked, her date angry and me telling them I should charge extra as they will tell this story forever.”

While 24/7 intoxicated interlopers are an expected Manhattan job hazard, The Big Apple’s got nothing on The Big Easy.

“My very first night, I’m nervously trying to hit every word correctly in front of a bachelorette party and, as I am doing this, a rubbery thing hits me on the cheek,” winces Walker. “Well, they had an inflatable sex doll and decided to rub its dick into my face.”

Tenured tour guides also excel at picking out the free-loaders.

“It’s common to have people try to join the group, thinking they’re being sly,” laughs Meyers. “We see you!”

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On-the-asphalt experience

I’ve inadvertently been training for this labor of love per previous pieces on The Ear Inn (via both New York magazine plus a video package for Maxim), Neir’s (Entrepreneur) and The Heidelberg (The New York Times) for my entire adult life.

Yael Bar-tur, social media consultant and co-host of the awesome Ask A Jew podcast, recently let me premiere my business for her 40^th birthday which included…*gulp*…30 of her closest pals.

Yael’s feedback was encouraging, yet vaguely insulting: “You were so thorough and meticulous in your preparation that it reminded me of those homeless people who walk around with a stack full of notes while mumbling to themselves.” But it went well enough that I heard from some friends of her friends wondering if I could helm a follow-up walk for the much easier group of four. Answer? Yes!

Robin and Nick Meahn, of the latter party, emailed a much kinder review: “You’re a riot! Great bars, comfortable pace, crazy history — definitely a fun way to spend an afternoon in the city!”

My most recent effort centered around another birthday via Emmy-award-winning reporter and two-time Drunk History vet Lauren Sivan. This little-sister-I-never-wanted was game to the point of dressing up as “Sexy Alexander Hamilton” during the proceedings. Not to be outdone and to paraphrase an old adage: Dress for the job you want, not the job you…uh…currently don’t have, I wore a movie-accurate homage to Daniel Day Lewis’s “Bill The Butcher” character in 2002’s Gangs Of New York. Annoyingly, Sivan assumed I was going as Willy Wonka.

Credit: Matt Smith/@FiveFanPS

On these three initial tours, we hit Paris Café (1873), The Dead Rabbit, (2013, but the edifice was built in 1828), Fraunces Tavern (a debatable 1762), Old Town Bar (1892), Pete’s Tavern (1864), and an indefensible Joey Roses (2022, mostly because comedian, Joe DeRosa, was on Sivan’s tour and owns the joint).

The stops went great, I studied up on all of the locales, but boy was I nervous about getting stumped by super inquisitive patrons. This, it turns out, is not a fear unique to me. “Every new guide fears answering a question with the response: ‘I don’t know'”, advises Walker. “The reality is there’s so much history, nobody knows it all and most tourists are there to have a good time while rooting for you.”

There are no small tours, only small tips

A reporter once asked Yankee great, Joe DiMaggio, why he played so hard during meaningless games. The Hall of Famer’s response: “There might have been somebody in the stands today who’d never seen me play before and might never see me again.”

Seth discovered the simple truth firsthand of why you need to go big every single outing during an early Big Onion gig. “We learned this on a rainy day in 1992 when one person showed up and I did the full walk for all of $10,” recalls Kamil. His decision not to cancel or give it less than his all became his first big break. “The person on the tour ended up being an editor for The Washington Post and we were subsequently featured on the front page of their Sunday travel section.”

Positive press is the kind of payment money can’t buy, but actual gratuities are the gain when it comes to this game and my guy in NOLA learned this lesson when it came to being cute while requesting a little something for the effort.

“We try different things and the dumbest one I ever did was saying ‘tips OR hugs are welcome'”, laughs Walker. “Sure enough, 30 pairs of eyes lit up, drunkenly embraced me, but did NOT fill my wallet.”

Adds Randy: “If I don’t make $80 to $100 per tour, I’m not happy. There’s no science to it, you can’t tell who’s going to be a good or bad tipper.”

To quote the aforementioned Bill The Butcher: “Don’t you NEVER come in here empty-handed again, you gotta PAY for the pleasure of MY company!”

My three downtown events garnered a little over two grand and I don’t pretend that this will be the average take as things progress. Yet with more movable feasts on the ole calendar, it has occurred to me that this might be the one freelance gig that AI can’t take. Yet.

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