About Travel on Points

Co-Founders of Travel on Point(s)

Shortly after going on our first date, we booked a free trip (on US Airways!) to Minneapolis for the Fourth of July. Shortly thereafter, we became obsessed with collecting Southwest points to fly for free and using “the card without any blackout dates” as much as possible. Little did we know the vast world of points and miles that we were ignoring. Fast forward 4 years, to the fall of 2015, when we became serious about this hobby. By 2016, we collected almost 1 Million Points & Miles, stacked our portfolio with many keeper cards, and set ourselves up to earn the best perk in travel: the Southwest Companion Pass. In 2017, we refined our skills and booked multiple international business class trips all around the world, booked $31,000 in free travel, and earned 1.1 Million Points & Miles. Since then, we’ve refined our earning & burning strategies and consistently earn 3+ Million miles per year. To date, we’ve booked over $1,000,000 in travel with points and miles!!!

Rick is based in the Seattle area (home airport SEA). His love for travel started in the military and he began blogging about travel as The Saving Traveler in 2011. Rick jumped fully into points and miles in 2014.

When it comes to points and miles, Rick focuses on maximizing spending and creativity, utilizing challenges and status matches, and new card sign-up bonuses.

His favorite travel destinations include the Czech Republic and any trip that involves sporting events. Rick also loves to share travel with his kids when possible, so they can experience things he was not able to as a kid. When Rick isn’t traveling or writing about it, he is working hard in City Government.

Shira began traveling as a child when her parents would load the family into the car and drive around the US. Although her family has always used points and miles to travel (even her grandparents!!), she entered the points and miles world herself after friends moved to England and she wanted to figure out an affordable way to visit.

Some of her favorite places she has visited include Porto, Sienna, and Ireland. When Shira is not traveling, she works as a pediatric occupational therapist in the school system and in her private feeding practice. You can also find her dancing, cooking, and exploring wineries locally as well as around the world.

Jenn is a journalist and former magazine editor with 15 years of digital media experience. A native South Floridian now based in South Louisiana, she was raised on Disney World and beach road trips. In her early 20s, she was bitten by the international travel bug while covering Caribbean vacations for publications like Jupiter Magazine, Stuart Magazine and Gold Coast Magazine. She later fell in love with Southern food and culture during her time as 225 Magazine’s longtime editor-in-chief.

Her favorite travel destinations include the desert Southwest and Mexico City, and she’s always down for a trip to European Christmas markets.

Kessin calls the Pacific Northwest home. The rural Idaho resident is the proud mother of two young-adult children. (One of whom is a travel addict, much like her mom!) Before ToP, Kessin spent years working for a school and trying to squeeze in as much travel as possible during breaks. While she has always obsessed over finding deals, her world really opened after discovering award travel. She regularly advocates that if she can make this hobby work on a budget, anyone can.

Kessin’s ToP trips have included exploring the jungles of Panama and walking through history in Egypt. When not adventuring, find her creating a new recipe or enjoying nature with her P2.

Based in the greater St. Louis Missouri area, Matt has been active in the points and miles community for over a decade. He practices quite a bit of solo travel, and he particularly enjoys traveling to Southeast Asia. Prior to ToP, he was a full-time professional dog show handler along with his wife. The husband-wife duo also breeds standard poodles, and Matt continues to attend a limited number of dog shows.

You can often find him relaxing at a Wyndham all-inclusive in Mexico—the ToP team has crowned him “Mr. Wyndham,” after all. But as he’s lounging poolside, know that he’s probably racking up tons of points buying dog food through Rakuten.

John’s award travel journey began on a cross-country JetBlue flight when he first saw the Mint seats at the front of the plane. He wondered, “How do I get one of those?” A quick Google told him: “You don’t, unless you’re rich.” That’s when he started researching points and miles. The more he learned, the more obsessed he became. When he ran out of friends willing to listen to him ramble endlessly about credit cards, he channeled his passion into a YouTube channel, JP Knowledge.

Since then, he has helped hundreds of travelers book award flights around the world. His favorite destination is Japan, which he plans to visit at least once a year for the rest of his life.

Sophie’s passion for travel began as a solo budget traveler, always looking for creative ways to explore more while spending less. Everything changed when she discovered the world of points and miles, transforming a personal hobby into a professional career dedicated to helping others unlock extraordinary travel experiences. Sophie has earned and redeemed millions of points to visit more than 20 countries (and counting) and experience travel she once thought was out of reach.

She is passionate about simplifying the often overwhelming world of award travel and empowering people to travel better, more often and for less.