Alright – so today we’ve got the honor of introducing you to Ross Alcorn. We think you’ll enjoy our conversation, we’ve shared it below.

Ross , thanks for joining us, excited to have you contributing your stories and insights. So let’s jump to your mission – what’s the backstory behind how you developed the mission that drives your brand?

I’ve always believed the best parts of life happen when we step away from our routines and embrace new experiences. That belief truly hit home around 2015, when I started organizing annual snowboarding trips with friends, which led to extended group adventures in Europe and surprise getaways with my fiancée. Every time, our well-planned trips, big or small, created memories that outlasted any work deadline or daily grind.

Yet for many busy professionals, especially those who feel too tired or stretched thin, travel can seem impossible. Time and money are always big concerns but I’ve seen others paralyzed by fear of the unknown (“What if I don’t speak the language?”), analysis paralysis (“There are so many options, I don’t know where to start”), and cultural misconceptions (“I’ve never done this; it’s too complicated”). Meanwhile, people try to hold out until they’re retired or ‘have more time,’ only to face burnout or health issues long before they ever book a dream trip.

I learned this firsthand in 2022. After a nonstop year juggling work and 9 weddings for others, I realized I hadn’t taken a real vacation for myself. No big international trip, no couples trips, or no personal reflection time. My stress hit a breaking point, and I found myself at the doctor’s office, burned out. I understood then that travel isn’t just a nice-to-have: it’s essential for mental clarity, creativity, and seeing life from a fresh perspective. It can even prompt healthier living, like opting for whole, unprocessed meals overseas and staying active while exploring new places.

That’s why I created Itinerary Boss: to help busy professionals see travel not as a luxury, but as a powerful tool for growth, connection, and well-being. Yes, I share practical frameworks for finding flights, leveraging rewards, and planning each step, but I also tackle the deeper obstacles, like fear, over-analysis, and the misconception that you only need one big trip a year. Over the last year alone, I’ve personally saved over $23,500 on flights and accommodations by combining personal daily spending with strategic credit card sign-ups. I’ve also guided friends from “I’ve never left my state” to becoming frequent flyers across Europe, and from “I don’t do credit cards” to racking up thousands in travel rewards.

It does take some effort, but that’s where my decade of trial-and-error comes in. By simplifying everything: from picking your travel style, to your next destination to the right card to using points effectively. I show you how to unlock travel opportunities without getting lost in complex details or endless internet research. It’s for the sales rep juggling quarterly targets, the tech pro working late nights, or anyone who fears it’s “too late” to start.

When I see someone, who once believed they “didn’t have the time or the money”, post photos from a group trip to Turks and Caicos, hiking the Cloud Forest Costa Rica, or somewhere in Portugal, it reaffirms why I do this. They come back recharged, healthier, and more open-minded, with stories about foods they tried, hikes they took, and cultures they discovered. That, to me, is the real reward of Itinerary Boss: helping people reclaim their time, broaden their horizons, and realize that travel can fit into even the busiest schedule, long before retirement.

I want others to look back and say, “Because of Itinerary Boss, I finally saw how to prioritize travel and in doing so, I discovered a healthier, more inspired version of myself.” That’s what drives me every day.

Awesome – so before we get into the rest of our questions, can you briefly introduce yourself to our readers.

About Me
I’ve been traveling since childhood: skiing around Colorado, exploring the Caribbean, and eventually studying abroad in Ireland during college. That experience opened my eyes to just how transformative travel can be. After graduating, I spent over a decade in high-pressure sales (medical device and software), watching how the daily grind and lack of real downtime erode people’s well-being. I became determined to help professionals recharge through meaningful travel.

How This Led to Itinerary Boss
In 2015, I began organizing annual group snowboarding adventures with friends, then I started putting together European itineraries for our group trips in 2017, and then starting planning surprise couples’ trips in 2022. It was obvious that busy professionals want to travel more but often feel they lack the time or the know-how. When I saw how much my step-by-step advice and “what not to do” lessons were helping, I launched my blog, podcast, and weekly newsletter, making it easier for anyone to get out there and explore.

What I Offer
1. One-Stop Resource
No more piecing together random articles, videos, and emails. I streamline everything in one place: from choosing the perfect destination to figuring out affordable flights and exactly what to pack. If I don’t have the answer, I tap into my network of travel industry contacts to fill in the gaps.

2. Real-Life Strategies
I’ve spent countless hours testing the best points, miles, and AI tools, so you don’t have to. Every strategy I recommend is something I’ve personally tried, ensuring you know it actually works.

3. Expert Community
Through my podcast and blog, I bring on seasoned travelers, industry pros, and innovators. You’ll get the latest insights on those channels as well as within my weekly newsletter from people living and breathing travel every day. This allows you to benefit from the best minds in the field.

Problems I Solve
1. Saving Time
Instead of Googling for hours or hopping between a dozen newsletters and YouTube channels, I’ve compiled the best tips, tools, and resources for you. Think of me as your personal research assistant, delivering clear frameworks so you can plan efficiently.
2. Saving Money
By showing you how to pick the right credit cards, earn rewards, and optimize budgets (without sacrificing quality), I help you make every dollar count.
3. Reducing Stress
Planning can be overwhelming. My method keeps it simple, from itinerary templates to recommended apps. You’ll know exactly what steps to take, when to take them, and why they matter—no second-guessing required.

What Sets Me Apart
I’m constantly on the lookout for next-level solutions, whether it’s a new points program or an AI-driven booking tool. But more importantly, I personally test everything before I suggest it. If something turns out to be more hype than help, you won’t see it in my recommendations. If a question pops up that I can’t answer, I connect with my network of travel experts to get you the best possible solution.

What I’m Most Proud Of
I’ve watched countless people shift from “I’m too busy to travel” to exploring places they once thought impossible. One friend in particular used my Turks and Caicos itinerary for their honeymoon, even though they’d never planned an international trip on their own. The experience went so smoothly that they helped organized a group adventure the following year and later joined me on trips to Greece. They even recently planned my bachelor party and did an amazing job. Seeing them grow from hesitant to fearless travelers proves that the right guidance can change your entire outlook on what’s possible.

The Heart of My Brand
Ultimately, my mission is to help busy professionals break free from burnout, see the world on their own terms, and create memories that fuel personal growth. By sharing the lessons I’ve learned, I want to show that travel isn’t a once-in-a-lifetime luxury. It’s a lifestyle you can embrace right now, no matter how packed your schedule is.

Let’s talk about resilience next – do you have a story you can share with us?

I spent years on the road in medical device sales, logging 60 to 80 hours a week and often living out of a suitcase. Despite hitting top 5% rep status and earning a solid income, I saw colleagues facing burnout and serious health issues. It hit me that if I kept up this lifestyle, I could be next. Hoping for a healthier environment, I switched to a different company, only to find even more micromanagement and the same empty feeling: I wanted more than just meeting quotas.

Realizing I needed a culture that valued people over numbers, I jumped into software sales. But once again, I found myself trapped by corporate constraints—no control over my territory or real say in how I worked. That’s when I knew I needed a career where I could call the shots. During this time, friends and coworkers kept saying, “You should start a travel business!” They saw how I loved planning trips, digging into credit card reward programs, and uncovering off-the-beaten-path gems.

So, I finally took the leap: I launched a podcast, started posting on social daily, hired virtual assistants, launched a blog, and a weekly newsletter to turn my travel know-how into a one-stop resource. All the systems and habits I’d built over the years, like investing, refining back-end processes, and staying curious through podcasts and books proved invaluable. I shaped my passion project into a real solution that saves busy people time, money, and stress.

Today, I can’t imagine a more satisfying role. Every text message I get “This trip was incredible!” or “Thanks for that credit card tip!” reminds me that each pivot, each late-night planning session, every 5:30 AM start time and each new skill learned was worth it. Each time I recall how close I came to burning out, I’m grateful I didn’t settle for a path that wasn’t serving me. Instead, I turned the stress, uncertainty, and “what ifs” into motivation to create something more meaningful both for myself and for the people I help explore the world on their own terms.

Have any books or other resources had a big impact on you?

Absolutely! These are the foundation to help educate and set myself up for success. Each of these resources has made an impact on how I approach both business and life:

The Psychology of Money (Morgan Housel) highlights how our behavior and mindset around money matter as much as spreadsheets and calculations. It’s a must-read for anyone wanting a healthier relationship with finances.
Shoe Dog (Phil Knight) taught me the grit and perseverance needed to build something from the ground up. It’s a reminder that legendary brands often start with scrappy, uncertain beginnings.
Buy Back Your Time (Dan Martell) is all about creating systems, delegating effectively, and protecting your own schedule: essential for any entrepreneur who values sustainable growth.
Traction (Gino Wickman) introduced me to the Entrepreneurial Operating System (EOS), which brings structure to running a business so it doesn’t run you.
The $100 Startup (Chris Guillebeau) encourages a lean, experiment-driven mindset, proving you don’t need massive capital to start creating value.
Die with Zero (Bill Perkins) shifted my thinking on wealth and time. It challenges the default “save everything for later” mentality and underscores enjoying life experiences sooner rather than later.
The Whole Story (John Mackey) similar to Shoe Dog, talks about the scrappy uncertain beginnings of Whole Foods.
The ABCs of Real Estate Investing (Ken McElroy) gave me a blueprint for trying to build long term wealth buy purchasing real estate, covering everything from analyzing deals to many other details.

I listen to 6-7 podcasts a day on 1.5x speed that keep me on the cutting edge and spark new ideas:

Motley Fool Money: always gives daily updates on companies, market trends, and investing advice
My First Million: feeds my curiosity around investing, market trends, and creative business concepts.
Online Marketing Made Easy (Amy Porterfield) is packed with actionable strategies to expand your reach and grow your audience digitally.
Rich Somers Report: Business, Wealth, Entrepreneurship and Real Estate Investing
BiggerPockets Real Estate Investing Podcast: keep me informed on the latest in property investing and real estate trends.
Business Made Simple (Donald Miller) simplifies everything from leadership to branding and helps me structure messaging in a clear, story-driven way.
The Wealthy Way (Ryan Pineda) focuses on balancing entrepreneurship, personal finance, and a purposeful life, complementing my belief in designing a career that doesn’t compromise overall well-being.

Contact Info:

• Website: https://itineraryboss.com
• Instagram: https://www.instagram.com/itineraryboss
• Facebook: https://facebook.com/itinerarybossinsiders
• Linkedin: https://www.linkedin.com/in/rossalcornru/
• Youtube: https://www.youtube.com/@itineraryboss
• Other: Podcast: https://open.spotify.com/show/1mmMJ6z3JdEOUJKUjLh8bD?si=-Rzy9J7wTTCNuheMYGfxbQ
  Free Resource: itineraryboss.kit.com/stress-free-travel-kit