If you find a coin on the ground heads up, it’s long been considered good luck.

And for one Virginia man who found a lucky penny and then used it to scratch off a winning lottery ticket, it looks like the adage might be true.

Tim Clougherty of Accomack County, Virginia, purchased a lottery ticket on April 29, 2024, that offered the prize of $10,000 a month for 10 years when he noticed a penny in the parking lot of the Mini Mart.

Related: Virginia Woman Hits $1 Million Lottery Jackpot — Her Second Win That Week: ‘I’m in Shock’

When he arrived back home, Clougherty used the penny to scratch off the numbers on the ticket. When he did, he won the grand prize.

“It took a week to really start sinking in,” Clougherty told lottery officials, per the Virginia lottery.

Instead of choosing the monthly payout, he took a lump sum in cash, which amounted to $1,028,000 before taxes.

The $10,000-a-month game first hit stands on January 2 and costs each player $20 per ticket to buy.

According to the Virginia lottery, the odds of winning the game’s top prize is 1 in 612,000, with two of the top prizes still remaining.

Last year, a Virginia woman hit the $1 million jackpot lottery for the jackpot after already winning a $500,000 online prize earlier in the same week.

Related: ‘I Am Blessed’: Woman Finds $100,000 Forgotten Powerball Ticket While ‘Going Through Papers’

“I’m in shock!” Jennifer Minton told lottery officials about the win last November. “I’m in disbelief!”

The Virginia Lottery raised an estimated $867 million last year, all of which went to K-12 education in the state.

I was talking to a friend recently who serves as the CTO at a mid-sized company and was struck by his sudden change in perspective on AI. Despite initial skepticism, he now believes artificial intelligence (AI) will revolutionize his industry. Yet, his main challenge has been convincing the rest of his executive team to adopt an AI roadmap. This scenario isn’t isolated.

In the last year, we’ve seen a contracted hype cycle around AI, which has caused many leaders to question if an investment in AI can truly yield proportional returns. These concerns aren’t without merit. VC firm Sequoia Capital recently estimated the AI industry spent $50 billion on Nvidia chips to train AI models last year, yet only yielded $3 billion in revenue.

Despite that disparity in investment, Sequoia went on to hypothesize AI is likely “the single greatest value creation opportunity” mankind has ever known, comparing its impact on business to that of the cloud transition. Unlike the cloud, however, which replaced software, AI has the potential to replace services, which the VC firm estimated has a total addressable market in the trillions. It’s the reason tech giants like Microsoft and Amazon continue to double down on AI investment.

Related: What Is Artificial Intelligence (AI)? Here Are Its Benefits, Uses and More

With so many competing narratives around the future of AI, it’s no wonder companies are misaligned on the best approach for integrating it into their organizations. The problem is most leaders are still looking at AI in its limited capacity as a software or tool rather than its ability to operate in a human-like capacity. Here are three common mistakes I see companies make when it comes to implementing an AI roadmap.

Underestimating and limiting AI’s potential

AI is widely viewed as a tool or software, but because it can create and reason, it has the ability to interact in a human-like capacity. Much like a junior employee who gets better at their job with experience, AI has the ability to learn from its interactions and refine its methods to improve its output and take on more work overtime.

For this reason, leaders who think of leveraging AI as “smart people” rather than software are better positioned to harness its full potential. Think about a company’s organization chart. If you were to write down the skills and tasks associated with each employee, then you can start to visualize where AI can be trained to augment or automate these tasks.

AI already outperforms humans in areas such as image classification, visual reasoning, and even English understanding, according to Stanford University’s recently published AI Index report. As of 2023, the report showed AI has surpassed human-level performance on several benchmark tasks, succeeding in helping workers become more productive and produce better-quality work. Another study out of the University of Arkansas showed AI outperformed humans in standardized tests of creative potential.

Unlike humans, however, AI scales up effortlessly as business demands increase, handling workloads without the physical and mental limits of humans. Adopting AI in this way means rethinking our team structures and workflows. It involves training teams to work alongside AI to enhance their roles and drive innovation.

This perspective shift is crucial because it allows leaders, who may not be accustomed to deploying technology themselves, to innately understand how to best leverage AI across their entire organization.

2. Trying to mimic another company’s AI use case

The more you start thinking of AI as smart people, the more you realize how individual every organization’s approach to building an AI roadmap should be. I like to think of AI implementation as the onboarding of new team members who need to fit within the specific dynamics of your company.

Take human resources for example — one company might have 10 people there; another only three, even if they’re the same size. This difference isn’t just about company size or revenue. It’s about how these companies have evolved.

Each business has its own unique structure, culture and needs. In order to realize generative AI’s full potential, PwC reported, businesses must take advantage of its capacity to be customized to a company’s specific needs and avoid the use-case trap.

Of course, general use cases for AI exist, particularly when it comes to enhancing customer service or sales. But, when you’re looking at a deeper integration of AI into a company’s operations, the approach needs to be custom-built, not copied and pasted from outside case studies.

Related: I Tested AI Tools So You Don’t Have To. Here’s What Worked — and What Didn’t.

3. Buying off-the-shelf products — not tailoring AI solutions to your needs

There are some great off-the-shelf AI products like ChatGPT, Dalle, and translation tools that solve specific problems within a company. The challenge with investing in a boxed solution for AI is that many leaders fail to see how AI can enhance operations at a systemic level.

The true power of AI lies in its ability to fundamentally transform your operations, not just perform isolated tasks. PwC’s 2024 AI predictions report states that many companies will find attractive ROI from generative AI. Still, few will succeed in achieving transformative value from it — the biggest barrier being the inability of leaders to think beyond boxed solutions and reimagine the way they work with AI.

When building an AI roadmap, leaders must first conduct a thorough assessment of their company’s processes. This means identifying areas with redundancies, recognizing outsourced tasks that could be automated, and pinpointing where the company invests heavily in human capital. By understanding these dynamics, leaders can tailor AI solutions to their company’s needs and transform how they work.

The more I talk to company leaders about integrating AI into their businesses, the more apparent it becomes that we leaders need to shift our perspective. When we view AI not just as a technological upgrade but as the onboarding of smart people, we’re better able to integrate it into our internal operations, enhancing performance and human ingenuity along the way.

Microsoft Office is a staple, which is why so many businesses rely on it for a range of functional needs throughout a given workday. If you are an entrepreneur leading a team with a member who doesn’t have a Microsoft Office license on their computer, that issue needs remedying right away. That is if you want to ensure your team has everything they need to do their jobs as well as possible.

Luckily, you can save extra on a lifetime license during a special price drop that ends today. Get Microsoft Office Professional Plus 2019 for Windows and Microsoft Office Home & Business 2019 for Mac for only $24.97 (reg. $229).

Each of these deals is good for a lifetime license that goes with one computer. It also warrants lifetime access to Microsoft’s beloved customer service team. The Mac version has Teams Classic 2019 and the Windows version comes with Access and Publisher, while both feature each of these esteemed software solutions:

• Word
• Excel
• Outlook
• PowerPoint
• Outlook
• OneNote

These fantastic deals, which end today, each have an average rating of 4.8/5 stars on the Entrepreneur Store. One recent five-star review describes the deal as a “great price and so simple to install! Extremely happy with my purchase of Microsoft Office Professional 2019.”

One of your responsibilities as a business leader is to make sure your team is set up with the tools they need to succeed. Today’s the last day you can set them up with one of these amazing licenses:

StackSocial prices subject to change.

Elvis Presley’s granddaughter Riley Keough is taking legal action against a company that advertised a public auction for Presley’s famed estate — alleging that the documents the company used to justify the sale are forgeries.

Keough, now the owner of the 13.8-acre Graceland estate, filed a 61-page lawsuit last week against Naussany Investments & Private Lending over the attempted public auction of the historic property, where several of her family members are buried.

^{Elvis Presley on the grounds of his Graceland estate in 1957. Photo by Michael Ochs Archives/Getty Images}

The filing details that eight months after Keough’s mother, Lisa Marie Presley, passed away in January 2023, Naussany came forward with documents claiming Lisa Marie had borrowed $3.8 million from them in 2018 and used Graceland as collateral.

“These documents are forgeries,” Keough asserts in the filing.

^{Riley Keough. Photo by Axelle/Bauer-Griffin/FilmMagic}

Keough pointed out that one of the documents used language that went into effect two years after Presley supposedly signed it.

The notary listed on the document also confirmed that she did not notarize the document or had ever met Presley, per the filing.

Keough further alleges that “on information and belief,” Naussany is not a real company but “appears to be a false entity.”

Kurt Naussany, named in the filing as the person acting on behalf of the company, told NBC News on Tuesday that he left the firm in 2015 and should not be named in the legal document. According to Keough’s filing, someone under the name of Kurt Naussany sent her legal counsel multiple emails asking to collect the claimed $3.8 million debt or risk a sale of Graceland.

Related: This Is How Much Elvis Presley’s Private Jet Just Sold for at Auction

The company has posted multiple public notices of the foreclosure sale this month and scheduled the auction for Thursday morning, at the front of the Shelby County Courthouse in Memphis.

After Keough’s request for a temporary restraining order, a Memphis judge froze the scheduled auction. An injunction hearing is scheduled for Wednesday.

The pandemic made global supply chain issues a common dinner table conversation. Now, with escalating geopolitical tensions and competing manufacturing hubs in China, India and Mexico, it can be hard for businesses to understand what the best strategy is for moving goods internationally.

Yet, despite the complexities affecting our global supply chains, the opportunity for businesses to engage in international trade has never been better. Advances in technology continue to make it easier to automate logistics. In fact, according to Acumen Research and Consulting, the global logistics automation market is predicted to reach $133 billion USD by 2030.

Not only is technology making supply chain logistics easier for businesses to manage, but in a down market, there can be opportunities to negotiate better deals with overseas suppliers, find new customers and create business models that adapt to future market conditions.

Regardless of your motivation, if you’re a business looking to expand abroad, here are three tips that can give you a competitive edge:

1. Understand regulatory requirements in advance

Paperwork may seem tedious, but in the world of global logistics, an incorrect or incomplete form can determine whether or not your shipment gets across the border. As the leader of a customs brokerage and freight forwarding business, I can tell you brokers spend a disproportionate amount of time following up with clients to complete the appropriate paperwork to clear customs.

Understanding simple but important details like what determines your product’s country of origin is instrumental for budgeting and planning. For example, if a business purchases materials from China and further develops them in the U.S. before resale, many leaders assume they qualify for reduced duty through North America’s free trade agreement (now known as the Canada, U.S., Mexico Agreement) — but this isn’t always the case. Products must meet a specific set of criteria to leverage the lower duty rates. Missed details like this can cost businesses a significant amount of money unexpectedly.

It’s also important to understand how exchange rates are calculated. Many businesses are surprised when they have to pay more for duty on a shipment when it arrives than they originally estimated. That’s because duty is calculated based on the exchange rate at the time the goods arrive at their destination. Exchange rates fluctuate, so it’s important for businesses to bear this in mind when creating budgets.

Related: Your Customers Don’t Care Where Your Ecommerce Business Is Based, So Be Ready to Ship Anywhere in the World

Factor In geopolitical tensions and changing market conditions

From China’s recently passed “retaliation tariff” to attacks on merchant ships in the Red Sea, growing geopolitical tensions are causing businesses to rethink their trade routes.

How a business navigates geopolitical disruptions largely depends on whether it is looking for a short-term or long-term strategy. If a company is looking for a short-term strategy, for example, it can likely adapt more swiftly to trade route disruptions. Businesses focused on long-term logistical planning, however, need to factor in the big-picture implications of geopolitical stability.

Take, for example, the current tensions between the U.S. and China, which have caused more manufacturers to set up operations in Mexico. If the U.S. decides to permanently shift its purchasing from China to Mexico, this change would have significant implications on the trade route’s pricing and capacity in the long term.

Businesses entering into international markets should factor in what parts of the supply chain are likely to be disrupted within the time frame they are targeting and consider whether or not they are well positioned to pivot, as necessary.

Related: How to Find International Customers and Partners as You Expand Your Market

Build strong relationships with international partners

One of the most overlooked factors in navigating global logistics is the importance of building strong relationships with partners abroad. Businesses seeking strong international partnerships must learn and adapt to the customs and cultures of the regions they operate within.

In my work, I do business with partners in multiple countries. Every year, when I attend their annual conferences, I notice the difference between leaders who respect the local customs and those who operate as though they were on home soil. Often, this attitudinal difference determines who establishes long-lasting, cooperative partnerships that lead to better pricing and referrals and who loses business altogether.

According to the International Labour Union, a staggering 70% of international ventures collapse due to cultural disparities. Every culture has its own etiquette. Doing a little research on the communication rules and accepted behaviors in the countries you’re operating in can go a long way toward establishing a cooperative partnership.

As a seasoned leader in international logistics, I’ve seen firsthand the transformative power of adapting to global market dynamics. For businesses venturing into international terrain, understanding regulatory landscapes, geopolitical shifts and cultural nuances not only mitigates the risk of expansion but can help maximize the opportunity.

It may be the end of an era for beloved seafood chain Red Lobster, which officially declared bankruptcy on Monday after months of speculation and dozens of abrupt restaurant closures.

Now, the company is speaking out to loyal customers — and investigating the role that its shrimp supplier may have played in its demise.

Related: Red Lobster Suddenly Shutters Dozens of Locations Without Warning Employees, Begins Auctioning Off Equipment

In a letter posted to social media, Red Lobster thanked customers for their nearly five decades of loyalty and assured the masses that the chain wasn’t going anywhere.

We’re here to celebrate every moment, big or small, with our valued guests. pic.twitter.com/JmAoNGP4a8

— Red Lobster (@redlobster) May 21, 2024

“Bankruptcy is a word that is often misunderstood. Filing for bankruptcy does not mean we are going out of business,” Red Lobster wrote. “In fact, it means just the opposite. It is a legal process that allows us to make changes to our business and our cost structure so that Red Lobster can continue as a stronger company going forward.”

Red Lobster noted that companies including Delta Airlines and Hertz “emerged stronger” after filing for Chapter 11 (Delta in September 2005, Hertz in May 2020) and found ways to bounce back.

“Birthdays, graduations, anniversaries, and yes, weddings. We’ve been here for them all,” the chain penned. “Red Lobster is determined to be there for these moments for generations to come.”

Red Lobster’s downfall was a slow burn, primarily blamed on an $11 million loss in November 2023 due to the chain rollout of an “Endless Shrimp” promotion. The deal offered customers all the shrimp they could eat for $20, and it proved to be a bit too popular.

Last week, it was reported that stores had begun shuttering without warning around the country, with dozens auctioning off all of their furniture and equipment online and some employees claiming they were given no notice ahead of time.

In a filing on Sunday, Red Lobster CEO Jonathan Tibus called out former CEO Paul Kenny and Red Lobster’s seafood supplier and owner, Thai Union, regarding decisions made surrounding the “Endless Shrimp” promotion and that Red Lobster is “currently investigating the circumstances” around the decision to make the promotion permanent instead of limited-time.

Related: Endless Shrimp Deal Is Too Popular, Red Lobster Loses $11M

“I understand that Thai Union exercised an outsized influence on the Company’s shrimp purchasing,” Tibus wrote. “[Red Lobster is] exploring the impact of the control Thai Union exerted, in concert with Mr. Kenny and other Thai Union-affiliated entities and individuals, and whether actions taken in light of these parties’ varying interests were appropriate and consistent with applicable duties and obligations to Red Lobster.”

Thai Union completed its purchase of Red Lobster in 2020.

In sports movies, coaches are larger-than-life figures, delivering inspirational speeches, running up and down the sidelines or even getting kicked out of games. One of my first soccer coaches had a much more understated style. Before games, he wished us luck with a cheerful smile. He certainly was not detached, however. During games, his advice was infamously constant and direct. He would call out phrases like “eyes up, “look for the pass” and “get back, ” each aimed at a certain player, often enough that we started using them as nicknames for each other.

While real-life coaches are often less dramatic, they are some of the first examples of effective, personal leadership that many people encounter. The coaches who often help shape us seem far removed from the world of business leadership and mentorship. But though coaching attire may not cross over into the board room, my time as both a player and a leader has taught me that direct, personal coaching techniques should.

There’s no one-size-fits-all approach to leading your company and developing your employees into effective leaders. However, harnessing coaching principles and techniques in your communication and mentorship can help you develop strong leaders and foster a productive work environment. Here are five coaching strategies you should consider implementing in your leadership style. These approaches will help you lean into the mindset of a coach, enabling you to lead your company, mentor your employees and develop a high-functioning team.

Related: Boss or Leader? 8 Principles to Truly Effective Leadership

1. Show up to practice

A coach’s main role is to be present during practices, drills and games. Likewise, If you only observe your employees’ work at an annual performance review, you’ll be too far removed from their work to be an effective mentor or help them develop their own leadership style. You need to observe their habits and strengths throughout, not just a few times a year or at the culmination of major projects. At Outpace SEO, our founders are present in meetings that are primarily led by the team leads they are mentoring. This allows them to take a hands-on approach to leadership training and observe their mentees in action.

2. Get to know your team

Effective coaching depends on the personal knowledge of a team and players. Be present in meetings, team-building exercises and your team’s daily life to develop a thorough understanding of your key players. This will help you develop an in-depth awareness of your team so that you can select the most effective potential leaders and build a workplace that functions smoothly and successfully.

The best coaches help players learn things about themselves, and you should know your employees well enough to do the same, identifying their skill sets and where they still need further professional development. Delegating may be necessary, but it should not translate into detachment. Where possible, schedule regular meetings with the developing leaders in your team regardless of whether you have an urgent task to discuss.

Related: 10 Leadership Lessons From Successful CEOs

3. Adapt your coaching style

Just like players on a team, different employees function differently and respond best to different versions of involvement and feedback. Some employees may need more frequent check-ins, while others may prefer reporting back or meeting when they have questions. Some employees may actually prefer more blunt constructive criticism to move forward quickly, while others need a more gradual mentorship approach with positive feedback and gentle redirection. Part of being a strong leader is being flexible. Don’t be afraid to ask the employees you are mentoring how they learn most effectively.

4. Isolate skill sets

Just like a coach designs practices based on the needs of their team, do not wait for your employees’ weaknesses or learning gaps to become an issue. Instead, identify the areas where your mentees need to grow and allow them to work on projects that specifically target those skill sets. Treat these projects differently than their regular roles; they will need more direct involvement from you. It may be helpful to tell your employees which projects are specifically intended as learning opportunities and reassure them that questions and feedback are expected as part of the process.

Related: 5 Traits You Must Have to Create More Leaders

5. Be vocal

Coaches do not think in terms of delegation and feedback, but of continual guidance and gradual growth. This mindset is key if you want to not only lead your team effectively but also develop leaders within your company. Be vocal with feedback of all kinds, positive and constructive. This will help you organically stay in touch with your employees and increase employee engagement. Determine what types of feedback work the best for your team and make it a regular, scheduled part of your role.

Your involvement should not be limited to constructive feedback but should also include celebrating wins as a team. Whether it’s for individual accomplishments or business growth, public recognition of success is an important piece of the coaching process. From informally mentioning positive results or completed projects in meetings to recognizing and rewarding promotions or work anniversaries, it’s important that you keep track of your team’s wins, big and small.

Thinking of yourself as a coach empowers you to continually seek momentum for your business. Developing an involved, personal and positive leadership style will not only boost employee engagement and company productivity but also help you organically find and deliberately mentor new leaders.

Xander Schauffele emerged victorious on Sunday, taking home the Wanamaker Trophy at the PGA Championship at Valhalla Gold Club in Valhalla, New York.

And for Schauffele, 30, and the other golfers who finished near the top, the payoff was rewarding. This year’s championship purse was $18.5 million — $1 million higher than a year ago and the largest in the tournament’s history.

Related: How Much Money Does Masters Winner Scottie Scheffler Earn?

Schauffele is now $3.3 million richer, while second-place winner Bryson DeChambeau earned $1.998 million, followed by Viktor Hovland in third place with a prize of $1.258 million.

Meanwhile, the tournament drama started early. Before dawn on Friday, the second day of the tournament, early favorite and 2024 Masters champion Scottie Scheffler, was arrested and booked on several charges including second-degree assault of a police officer, and is scheduled to be arraigned on June 3. He reportedly warmed up in jail before being released to make his tee time. Scheffler finished the tournament in a four-way tie for 8th place.

Related: PGA Championship Payout: How Much Do the Winners Take Home?

The PGA Championship purse was slightly less than the Masters this year, which saw a prize purse of $20 million and a payout to Scheffler of $3.6 million for winning the tournament for the second time.

Golfers in the top 10 all take home at least $500,000. All players received at least $4,000 just for finishing the 36-hole course.

Here’s how the payout went for the top 20 players this tournament.

1st: $3,300,000, Xander Schauffele

2nd: $1,998,000, Bryson DeChambeau

3rd: $1,258,000, Viktor Hovland

4th: $888,000, Thomas Detry and Collin Morikawa ($814,000 per player)

5th: $740,000

6th: $660,580 — Justin Rose and Shane Lowry ($639,440 per player)

7th: $618,300

8th: $577,790 — Scottie Scheffler, Billy Horschel, Robert MacIntyre and Justin Thomas ($521,418 per player)

9th: $539,030

10th: $502,040

11th: $466,810

12th: $433,340 — Taylor Moore, Rory McIlroy, Lee Hodges, Sahith Theegala, Dean Burmester and Alex Noren ($359,943 per player)

13th: $401,630

14th: $371,690

15th: $343,500

16th: $317,080

17th: $292,420

18th: $269,520 — Rio Hisatune, Harris English, Tony Finau, Keegan Bradley and Austin Eckroat ($230,764 per player)

19th: $248,380

20th: $229,000

21st: $211,390

22nd: $195,530

23rd: $181,440 — Russell Henley, Tom Hoge and Maverick McNealy ($170,137 per player)

24th: $169,990

25th: $158,980

The best commencement speeches are often motivational and thought-provoking, leaving new graduates optimistic as they head into the “real world.”

But for the Class of 2024 at the University of Massachusetts Dartmouth, new grads walked away with more than just a wealth of knowledge — they left their ceremony with an extra $1,000 in their pockets.

Related: ‘There Is More To Life Than Work’: Bill Gates Delivers Emotional Message To Graduates About Learning To Take A Break

Last week, the founder and CEO of Granite Telecommunications, Robert Hale Jr., spoke to grads at the University of Massachusetts Dartmouth about their futures and shared a story about a time when his business suffered a $1 billion loss in just one day to explain the importance of perseverance through failure.

“It’s okay to fail,” Hale told graduates. “Life will give you challenges and if you take those challenges you’ll fail from time to time — don’t worry about it … don’t fear failure, understand that it’s just part of the process, and if you use that fear of failure to motivate yourself, you’ll be better for it.”

Then, as he wrapped up, he shocked the audience by announcing he was giving each graduate graduate $1,000 — but there was a catch.

“These trying times have heightened the need for sharing, caring, and giving,” Hale told students. “Our community needs you and your generosity more than ever.”

The students were given two envelopes with $500 each — one was intended for the students to keep for themselves while the other was for them to give to someone else in need.

Related: Sheryl Sandberg’s Advice to Grads: Banish Self-Doubt, Dream Bigger and Lean In, Always

“As the degree conferral was about to begin, Hale came forward and let the graduates know he had one more bit of advice for them. He told the eager crowd that for him and his wife Karen, ‘the greatest joys we’ve had in our life have been the gift of giving,'” UMass Dartmouth said in a release. “Hale let the Class of 2024 know that the two large duffle bags being brought up on stage by security were packed with envelopes full of cash.”

There were roughly 1,200 students in UMass Dartmouth’s 2024 graduating class.

Hale’s current net worth is an estimated $5.4 billion.

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!”

Related: Can a Great Bloody Mary Cure a Bar’s Financial Hangover?

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!”

Related: At the Comedy Cellar, the Customer Is Always Right – Entrepreneur

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.

Related: 7 Ways to Snag Tourist Dollars and Keep Locals Happy at the Same Time