Why Your AI Keeps Forgetting (And the Three Levels Most Tour Operators Don’t Know About)

Tired of correcting your AI on the same things over and over? Most tour operators are stuck at level one of AI use. Here's how memory changes everything, and the three levels you need to know.
The Right Way to Set Up AI for Your Tour Business

Why Your AI Keeps Forgetting (And the Three Levels Most Tour Operators Don't Know About)

This is part five of our Putting AI to Work in Your Tour Business series. Watch the full series here and read part one here.

You open your AI tool, ask a question, and get a decent answer. The next day you come back, ask something similar, and it’s like the AI has no idea what you told it yesterday. You’re searching back through old threads to avoid repeating yourself. Or you’ve built up some context inside a project, it works great for a while, then suddenly it breaks. You corrected something last week, and now it’s back to the old way.

If that sounds familiar, you’re not alone. This is where most tour operators get stuck. And the reason has nothing to do with the AI tool you’re using being broken. It has everything to do with which level of AI use you’re operating at.

Level One: Chats

This is what most of us are doing right now. You open ChatGPT or Gemini, ask a question, get a response. It’s ping-pong. Fast, easy, and for a lot of jobs, perfectly fine. You don’t always need to load up your AI with context to get a useful answer.

But here’s what’s happening under the hood: Every new chat starts from scratch. There’s almost no memory between sessions unless you turn on specific features, and even then, what the AI chooses to remember isn’t really in your control.

The other friction point at level one is the constant uploading. You’re hunting down documents, copying and pasting from browsers, re-explaining your business every time. It adds up.

Level Two: Projects

This is where most operators move to next, and it’s a real upgrade. ChatGPT, Claude, and Gemini all have something like this, and the idea is the same. You give the project instructions, you upload some files, and every new chat inside that project starts with that context already loaded.

If you take the AI brain we built earlier in this series and drop it into a project, you’ll see better outputs almost immediately. It knows your business. It has access to your reference documents. It knows who you’re talking to.

But projects have a blind spot. Each conversation inside the project is still separate. You correct the AI in one chat, telling it to stop using the word incredible, or to drop the em dashes, and that correction vanishes the moment you close the conversation. Open a new chat in the same project and you’re explaining it again.

Persistent context, yes. Memory that compounds, no.

Level Three: Agents With Memory

This is where the experience changes. Agents with ongoing memory work differently from chat. You give the agent a goal and let it figure out the path. More importantly, when you correct it, that correction goes somewhere it can find later.

Here’s how it actually works: Remember those markdown files we built into your AI brain? Your business profile, team, brand voice, processes, tools. In a setup like Claude Cowork, those files live on your computer. The AI reads them at the start of every conversation, and here’s the real breakthrough: It can also update them.

So when you say, that’s not how we handle cancellations, or we don’t use that phrase with guests, the AI doesn’t just adjust for that conversation. It opens the relevant file and updates it. Next conversation, next day, next month, the correction is already there. Correct once, remember forever.

A Real Example From Guest Focus

When we first built our AI brain, we asked it to draft a follow-up email to a coaching lead. The output was decent, but it had no testimonials in it. Why? Because our testimonial database wasn’t in the brain yet. So we uploaded it, told the AI where to find it, and asked it to remember. Now any time we draft something where social proof would help, it pulls from the right place.

Same thing happened with our coaching team. The AI had names and roles from our early setup, but not LinkedIn profiles or links to their bios on the Guest Focus website. We had Claude Cowork go pull the URLs and update the team file. Now when it drafts a response that mentions a coach, it can reference their actual background and link to their interview videos.

Small additions. But they compound.

Why This Matters Beyond Memory

Memory is the foundation, but the real shift at level three is independent action. Agents can run on a schedule. They can act on triggers. They can work while you’re sleeping or out walking the dog.

Recently we wanted to showcase client logos on our website redesign. Instead of manually hunting for each one, we gave Claude Cowork the goal: Find the logos for our coaching clients, save them as PNGs in a folder, ready to drop on the site. It used the client list from our AI brain, used the Chrome connector to visit each website, downloaded the files, and dropped them into the folder. We just gave it the goal.

That’s not a chatbot experience. That’s a business system.

The Question Worth Sitting With

How many times have you corrected your AI on the same thing? The same tone issue. The same formatting preference. The same fact about your business that it keeps getting wrong. Every one of those corrections is a memory that should stick.

If it’s not sticking, you’re at the wrong level for the work you’re trying to do. The shift from forgetting to remembering is what changes AI from a novelty into a real business partner.

Where to Go Next

If you want to set up an AI tool with ongoing memory, we recommend Claude Cowork paired with the AI brain builder prompt from earlier in this series. The key is to always work out of that same folder, because that’s where the corrections and updates live.

If you want to swap notes with other operators experimenting with this, the Tour Business AI Lab is a free community where we share what’s working. You can find it at guestfocus.com/ai.

Want help leveraging AI for your tour business? Book a free 45-minute strategy call with us today!

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Avital Ungar is the founder and owner of Avital Food & Drink Experiences, a culinary company that hosts in-person and virtual events for corporate team building, client entertainment, and conferences. Her mission centers on deepening human connection through storytelling, food, and drink.
Ungar’s passion for the finer points of life began while living in Paris and the quaint town of Aix-en-Provence in Southern France, where she embraced the cultural norm of afternoon wine and explored the countryside’s culinary offerings. Upon returning to the United States, she pursued formal wine education and is now a certified sommelier.
A Phi Beta Kappa UCLA graduate, Ungar studied Art History, French, and Mandarin Chinese, though she jokes she wishes she could have majored in Chocolate. After living in Shanghai and working in the Chinese Contemporary art market, she returned to her hometown of San Francisco to pursue her professional interests in art and food.
Since April 2011, Ungar has operated Avital Food & Drink Experiences, offering progressive dining food tours in San Francisco, Los Angeles, and New York City, where each course is served at a different restaurant. The company also provides dining experiences, conference activations, and interactive meals in 12 cities nationwide. Her virtual offerings include culinary experiences with ingredient delivery featuring award-winning chefs, bartenders, and sommeliers, along with virtual mixology classes, cooking classes, water tastings, and aperitif hours.
In September 2022, Ungar launched Edible Architecture, which creates innovative holiday products including Charcuterie Chalet Kits – savory gingerbread houses made from charcuterie and cheese board items, complete with “Salami Shingles” and “Parmesan Snow.”
Ungar has been featured in The New York Times, served as a judge at the Good Food Awards, International Chocolate Salon, and Best of The West Rib Competition, and has appeared on the Travel Channel, CNN, and in USA Today.
Midgi is the owner and Chief Eating Officer for Juneau Food Tours and Taste Alaska! She has lived in Alaska for more than a dozen years and got her start in the culinary industry as a food writer and blogger. Her tour company opened in 2014 and has hosted thousands of hungry visitors in Alaska’s capital city. In spring 2020, Midgi launched Taste Alaska!, a subscription box service to ship shelf-stable Alaskan food gift boxes.
The pandemic also presented the opportunity to create www.globaltoursconnect.com, an online boutique marketplace for food, history, and cultural tours.
Her passion for food and telling the story of Alaska have been noted in the New York Times, Washington Times, Washington Post, Vogue.com, Forbes.com, AARP, as well as countless blogs and international and national television shows, including All the Best with Zita and Gordon Ramsey: Uncharted.
Gez Hamer is an entrepreneurial leader with extensive experience building and scaling businesses from startup to growth phases. He possesses strong strategic decision-making abilities and hands-on leadership skills, with experience across startups securing Series A investment, scale-ups obtaining continued funding, and post-acquisition companies ranging from SMEs to publicly listed global players.
Since June 2025, Hamer has owned Nautica Collective, a company reshaping luxury yacht travel for the new generation of travelers. Nautica Collective offers curated, boutique yacht experiences designed for over-30s millennials seeking connection, culture, and comfort through small groups, hidden anchorages, and chef-hosted dinners under the stars. The company operates routes in Mallorca, Greece, the Caribbean, and beyond, positioning itself as “aspiring luxury meets authentic adventure.”
In January 2025, Hamer co-founded Transcend Consultancy, which helps businesses navigate growth challenges with cost-effective solutions. The consultancy works with founders to streamline operations and expand into new markets, specializing in the transition from startup to scale-up with strategies built for today’s fast-changing business landscape.
Previously, Hamer served as Chief Operating Officer at ExperienceFirst from November 2022 to December 2024, Interim Chief Commercial Officer at Bundl from July to November 2022, and CEO/Management Consultant at GJH Consulting from October 2016 to November 2022. His diverse background spans consulting, operations, and commercial leadership across multiple industries and business stages.
Akila McConnell is a dynamic entrepreneur and cultural historian who owns Unexpected Virtual Tours and Training, and Unexpected Atlanta Tours & Gifts. She creates radically creative cultural training sessions for remote teams and immersive tours for visitors to Atlanta.
Since 2020, her virtual tours company has been featured in The New York Times and Forbes, specializing in cultural awareness events around Juneteenth, Hispanic/Latinx Heritage Month, and Pride. Her Atlanta tours business, operating since 2015, has been named one of Conde Nast’s 16 best things to do in Atlanta and National Geographic’s top tour in the city.
As a freelance culinary historian and writer since 2009, McConnell contributes to major publications including Conde Nast Traveler, USA Today, and National Geographic Traveller. Her book “A Culinary History of Atlanta” was a finalist for Georgia Author of the Year in History in 2020. She also hosts “Savory Stories,” a food-focused podcast on WABE, Atlanta’s NPR affiliate.
McConnell specializes in sharing stories of disenfranchised and minority populations through food, history, and immersive experiences that challenge the perception that cultural education has to be boring.
A Colorado native, Staci left a job she loved designing dental offices and funeral homes, to accompany her husband on a job transfer to the Central Coast of California in 2009. At the height of the Great Recession, jobs in an area known for its high density of retirees – let alone jobs in her industry – were scarce to non-existent.
After a couple unsuccessful years trying to resurrect her thriving career, someone mentioned a Food Tour. In a few short months she researched, built, and launched Carmel Food Tours (CFT). Now in its 12th season, CFT is expanding and rebranding to Enjoy Carmel, offering more than just food tours. CFT employs 6 guides, and plans to grow the staff by 50% in 2023.
In her free time she enjoys traveling, pickleball, and Pilates with her husband, and tossing a tiny ball at the beach for her fluffball Chuck.
Simon began his career in tourism as a tour guide with Fat Tire Tours – Paris. As a trained social studies teacher and a dual FR/US citizen, this job fits like a glove! After three years as a tour guide with Fat Tire and side-hustling as an independent motorcycle guide, Simon returned to FTT – Paris to create its human resources department.
Specializing in local compliance and talent acquisition, Simon took over the hiring strategy for FTT’s European operations in autumn of 2019. With a new group of trainees set to begin work in several cities, COVID required an immediate 180 degree turn for everyone. After a decade of building tour leader teams, Simon combined his two passions and started a motorcycle sidecar tour business, and welcomed his first guests in Paris in spring of 2022.
Born and raised in Charleston, SC, Catherine began her 18-year career in tourism waiting tables while in college at one of Charleston’s busiest restaurants. What started as just a fun job that paid the bills and allowed for many social outings with friends, had turned into something that made her realize that working in hospitality was the only industry she ever wanted to be in.
After graduating from the College of Charleston, she came to work at Bulldog Tours in 2007. Serving as Operations Manager, Catherine oversees a staff of 50+ tour guides and customer service members. The best part of the job for her is seeing guests experience and love Charleston in the same way the staff does. When she’s not working, she enjoys playing volleyball, going to the beach and spending time with her husband and two super adorable daughters.
Chad is an experienced tour leader, trainer and tour business consultant. He’s been the go-to-guy for developing world-class training programs and leading global teams for tour operators such as G Adventures and many small to medium tour and activity businesses. Chad also comes from a background of startups in the tech industry, having worked for Adventure.com, Airbnb Experiences and other great companies.
Live the life you dream of living… That’s Chad’s mantra and he does his best to bring it to life every single day. Chad’s a big fan of micro adventures and spending quality time in the wilderness, sailing, hiking and camping with his wife Julia, daughter Cali and friends.
John founded Bulldog Tours in 2001 as a hobby with a goal of helping preserve his hometown. This sustainable tourism model has raised over $4M to help preserve many of Charleston’s most historical landmarks. Bulldog Tours offers a variety of history, food, pub and ghost walking tours with over 50 tour guides.
John is the Chairman of the Charleston Area CVB’s Travel Council and on the Advisory Board for the College of Charleston’s Hospitality Tourism Management Department.
Ralph Velasco is the founder of Continental DRIFTER® Experiences, where he has developed more than 200 once-in-a-lifetime travel experiences since 2008. He specializes in travel product development, researching and vetting local partners in destinations worldwide, conducting scouting trips with local operators, and creating unique itineraries that guests remember for a lifetime.
Velasco has personally led small group tours (4-10 participants) to more than 30 destinations including Antarctica, Spain, Portugal, Italy, France, Cambodia, Lapland, Vietnam, India, Bhutan, Romania, Mexico, Morocco, Turkey, Iceland, the Baltics, and the Adriatic. As founder of Continental DRIFTER®, he handles every aspect of the business from branding and trip design to marketing, social media management, contract negotiations, and client follow-up.
Since December 2018, Velasco has expanded his expertise through The Continental DRIFTER® YouTube channel, which features more than 75 videos offering travel advice, photography tips, destination guides, and interviews with locals. The channel targets GenX and Baby Boomer travelers and serves as the hub for his international tours. He conceives and films all content, oversees channel branding and optimization, writes scripts, records voiceovers, and manages social media distribution to increase viewer engagement.
Through his comprehensive approach to travel experiences and content creation, Velasco combines his extensive international travel expertise with practical advice for mature travelers seeking authentic, well-curated adventures.
Yaron’s love for travel turned into an 18-year career building one of Israel’s most successful travel companies. What started as personal wanderlust became Abraham Tours and Hostels – a business he co-founded and grew from scratch into a powerhouse serving 100,000 travelers annually.
As CEO from 2010 to 2022, Yaron learned how to turn great experiences into profitable business. The early years weren’t profitable despite rave reviews – they focused on creating amazing content without understanding business fundamentals. Once they cracked variable pricing, team management, and operational efficiency, everything changed.
Yaron and his team built systems that let him step away from answering every email. He developed bonus schemes that kept their best guides and drivers loyal for years, reducing industry turnover. Most importantly, he learned how to scale across multiple destinations while maintaining quality and profitability.
After stepping down as CEO in 2022, Yaron spent eight months traveling before launching his consulting practice. Now he works with the Israeli National Parks Authority on major system overhauls and helps tour operators worldwide through Guest Focus coaching, as well as other consulting projects.
Yaron brings this scaling experience to operators ready to grow beyond the one-person show, helping them delegate, systematize, and make data-driven decisions that improve both profits and personal freedom.

Accomplishments:

  • Co-founded and grew Abraham Tours & Hostels from startup to serving 100,000 tour participants and 200,000 hostel guests annually

  • CEO from 2010-2022, scaled company to 4 hostel locations plus a multi-destination tour operations

  • Established Israeli Hostel Association 17 years ago, served as general manager and chairman

  • Developed variable pricing schemes and team management for 100+ subcontractors/guides

  • Successfully exited as CEO in 2022, now consulting & mentoring various businesses in Israel and globally

After receiving his Applied Degree in Ecotourism & Outdoor Leadership from Mount Royal University in Alberta, Canada, Dave Kratt has made a living for the past 20 years in the alternative tourism industries as a guide, researcher, instructor, teacher, facilitator, manager, business owner, and naturalist. He has worked in many world regions including Central America, Australasia, Asia, and North America, applying his skills and training to various tourism, cultural, and environmental initiatives.
Kratt has been fortunate to find success through starting a number of businesses, which he tailors to achieve a more personal work/life balance. Recently, he made the significant decision to sell his farm and offload all personal and business assets, relocating his family (wife, daughter, and two dogs) to be more present in aiding his aging parents. This transition has provided him with the opportunity to share his business expertise through new and exciting channels.
In addition to his regular business coaching role with Guest Focus, Kratt recently started a consulting business called Wild Kratt Tourism Consulting Ltd. The two operations complement each other and have helped him find ways to share his passions for recreation, tourism, travel, and nature while enabling others to engage in these activities safely and consciously toward their potential social, economic, and environmental impacts.
Klaudija packed her bags in Slovenia 20 years ago with no plan except to see the world. A travel rep job in Turkey was supposed to be temporary – just long enough to fund the next adventure. Instead, it launched a global career building tour businesses from nothing and selling them for profit.
Her biggest win came with Urban Adventures, joining when it was just an idea without a brand. Over 10 years, she helped grow it to 500,000 passengers working with 170 tour operators worldwide. She spearheaded expansion into experiential products and negotiated one of the industry’s first media partnerships with New York Times Journeys.
Klaudija also built and sold two tour businesses in Ljubljana and London. Not many coaches have walked the startup-to-exit path.
Now she’s Head of City Experiences at TUI, leading an experimental department testing new products. This year her team achieved 75% revenue growth and 50% growth in passenger numbers.
Klaudija brings startup grit and corporate scale to Guest Focus coaching. She specializes in sales strategy, marketing optimization, and distribution channels. Her coaching clients particularly value her website development expertise – she’s guided three members through complete overhauls.

Accomplishments:

  • Grew Urban Adventures to 500,000 passengers working with 170 tour operators worldwide over 10 years
  • Negotiated one of industry’s first media partnerships with New York Times Journeys
  • Built and sold two tour operating businesses in Ljubljana and London
  • As Head of City Experiences at TUI: achieved 75% revenue growth and 50% passenger growth in one year
  • 20 years in travel industry across multiple roles: rep, guide, marketing, sales, managing director

Angela Shen is a proven business builder with deep roots in entrepreneurship and brand management.

Angela founded Savor Seattle in 2007 and grew it to a $1M business in under 5 years without outside investment. During the COVID shutdown in 2020, she pivoted the business from food tours to curated food boxes and grew revenues more than 2x her best tour year! Angela was named in Puget Sound Business Journal’s Top 40 Under 40, and started a second tour business Savor the Wild Tours in 2023.

Angela’s expertise in business strategy and operations hails from the consumer packaged goods sector where she previously worked in brand management at PepsiCo and looked after iconic brands including Quaker Oatmeal and Life Cereal. Angela is a graduate of the Wharton School of Business and serves on the board for Visit Seattle.

Ana stumbled into tourism backwards in the 1990s—first as a guide in remote Northwest Argentina mostly because she spoke English where few others did. As a horse rider, mountaineer, and fitness trainer, she naturally fell into adventure guiding, learning the hard way by doing first and studying later.

Everything began to click when she attended her first ATTA Adventure Travel Trade Summit in 2014. Suddenly, the entire structure of the travel industry made sense—the difference between operators and travel advisors, how B2B relationships actually work, or how marketing for a B2C audience is so different. That clarity saved her years of trial and error.

Since then, Ana has built her own travel company, Adentrando, initially as an active inbound tour operator for Northwest Argentina serving multi-day B2B clients, and since 2023 as an Argentina DMC and also operating trips in Latin America, working together with trusted partners. She’s become an ATTA trainer, developed Adventure Travel Guide Standards, and spoken at major industry events about responsible tourism and community partnerships.

Ana brings her hard-earned industry knowledge to Guest Focus members, particularly those starting out or pivoting their business models. Her specialty is multi-day trip design—creating itineraries that tell a story and have a positive impact, rather than just connecting attractions. She helps operators avoid the mistakes that cost her years of learning, turning complex industry relationships into clear, actionable strategies.

Accomplishments

  • First woman adventure travel guide in Northwest Argentina, driving Land Rovers across deserts
  • Been an ATTA trainer since 2016, traveling to Jordan, Chile, Colombia working with suppliers
  • Co-creator of Adventure Travel Guide Standards (2015) – one of 15 people who developed industry standards
  • ATTA business partner since 2012 and trainer for their Adventure EDU program
  • Speaker at major industry events like Pure, Lata in London, ATTA World Summit, Adventure Elevate on responsible tourism and adventure travel product design.

Casey spent 14 years at Zegrahm Expeditions, climbing to VP of Marketing Communications where she managed a million-dollar budget. Through her leadership, Zegrahm increased business with travel advisors by 10% and cut direct mail costs by 23% – real money when working with those numbers.

After Zegrahm, she spent a decade at the Adventure Travel Trade Association (ATTA), growing net revenue by 30% and profit margins by 60%. Through COVID and its recovery, as President of the ATTA maintained a 90% team retention rate by keeping people engaged and motivated.

Now running Casey Hanisko Coaching and Consulting in Seattle, she’s doubled her own revenue in one year while becoming ACC certified through the International Coaching Federation. She’s also Dare to Lead and DISC and EQI assessment certified, bringing structured tools to her approach.

Casey specializes in strategic planning and getting tour operators out of the daily grind so they can work on their business instead of in it. She helps solo entrepreneurs and small teams document knowledge, define roles, and build growth systems. Her Guest Focus clients have hit major milestones – one reached a million in revenue, others doubled income, and several Guest Focus members have brought on new team members, consultants, and partners.

She’s passionate about supporting women leaders and purpose-driven operators focused on responsible tourism.

Accomplishments:

  • Grew ATTA net revenue by 30% and net profit margins by 60%
  • Maintained 90% team retention rate during COVID challenges
  • At Zegrahm Expeditions: managed million-dollar marketing budget, increased travel advisor business by 10%
  • Cut direct mail costs by 23% (significant savings on million-dollar budget)

Jess quit her high school teaching job for what she thought would be one fun summer guiding bike tours around Paris. Eleven years later, she’s still there. Turns out, trading lesson plans for tour routes was the best career move she never planned to make.

She worked her way up from tour guide to director at Fat Tire Tours, learning every role – designing tours, training guides, managing ticketing, overseeing operations. This ground-up experience taught her what works for staff. She now works as Europe Head of Retail, as well as overseeing Paris/Versailles operations.

Her biggest win? Maximizing operational efficiency while keeping the human element intact. She redesigned scheduling systems to reduce labor costs and spoilage, automated data processes, and streamlined operations without losing Fat Tire’s family-friendly culture.

What she’s most proud of is her team development approach. Using her teaching background, she focuses on staff satisfaction and growth, helping guides and managers build confidence. Many told her the training changed not just their work performance, but their lives outside the company.

Jess brings this dual focus – operational efficiency plus people development – to Guest Focus coaching. She works with operators from solo startups to multi-million dollar companies, helping them increase profitability while maintaining authentic culture. Her coaching clients especially appreciate her reminder to take breaks and prioritize self-care.

Accomplishments:

  • Worked way up from tour guide to director at Fat Tire Tours over 11 years
  • Maximized operational efficiency – redesigned scheduling systems to reduce labor costs and spoilage
  • Automated data entry processes and streamlined operations without losing company culture
  • Developed team management systems with 60+ guides, created buddy system and quarterly reviews
  • Created staff retention program with traditions, events, and ‘dominate’ t-shirt recognition system

Fieldbook focuses on one thing: simplifying all the behind-the-scenes work that goes into delivering a tour.

The Fieldbook platform makes it easy to:

  • Publish stunning, interactive itineraries digital and paper itineraries
  • Equip guides with a comprehensive run-sheet
  • Streamline supplier management and track reservations and rooming lists
  • Bring all your tours into one connected workspace

Unlike other platforms, Fieldbook is simple and easy to use. And because it’s a small business just like you, you’ll get the kind of support big software companies can’t offer. That means getting up and running in days, not weeks.

If you want to give Fieldbook a try for your next tour, you can sign up here or if you want to have a chat feel free to reach out to me directly at [email protected].

More About Fieldbook

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Nathan’s takeaway: “Don’t wait until you’re burned out. ResmarkWeb helped us grow without compromising our values.”

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