Episode 57:

For 27 years, Tammy Weiler has dedicated her life to encouraging singles over 50 to “hit the road” and make traveling the world an opportunity to have life-changing experiences, build self-esteem and enjoy the opportunity to make meaningful and life-long friendships.

Traveling started at an early age for Tammy, taking her first cruise at age 15 and falling in love with the excitement of the unknown. After graduating from Northern Illinois University, she was accepted to the highly sought-after position of flight attendant with the international carrier, Pan American World Airways, then led a travel department for a sales promotion agency in New York, where she created incentive travel programs for Fortune 100 companies.

By age 30, Tammy was faced with a problem…her friends were married, having children and no longer available to travel with her. After years of traveling with a passport in her back pocket, Tammy was not ready to let being single stand in her way: she began traveling solo, was inspired with the idea to “bring singles together for vacation” and founded Singles Travel International in 1993.

Tammy has successfully navigated the travel industry for 27 years, and, under her leadership at Singles Travel International, has built the largest online community of single Baby Boomer travelers in the world, with more than 49,000 members. Her expertise in helping singles “get out there” and rewrite their personal stories and her strategic approach to using technology to reach thousands of singles has attracted media attention. She has been featured in The New York Times, Chicago Tribune, Sun Sentinel, Kiplinger, USA Today, Forbes.com, American Airlines’ Nexos magazine, the Los Angeles Times, among others. She has also been invited for numerous live TV appearances for interview segments with Forbes, CNN, Fox News and ABC.

While facing COVID-19, Tammy and her team faced extinction. But rather than die on the vine like many other travel companies, they launched a new site offering live events and a social network for singles over 50 to carry out their mission.

Tammy graduated Cum Laude with a bachelor’s degree in Marketing and Language from Northern Illinois University, she is fluent in Spanish and French and has traveled to more than 55 countries. Tammy lives in Florida, where sailing and learning to play ukulele and trumpet fill her free time.

What the podcast will teach you:

  • How Tammy built Singles Travel International serves its over 25,000 members with a dedicated concierge team and a full, premade travel itinerary
  • How the outbreak of the global pandemic has had a staggering impact on the entire travel industry, and how Tammy’s business has gotten creative with their offerings to survive
  • How Tammy and her team have overcome significant challenges through the pandemic, including losing the ability to bill credit cards
  • How SingleLife.Today came about as a response to the pandemic and the need for social distancing, and how this new offering is rapidly growing
  • Why growing out the team was a major challenge Tammy faced after achieving the seven-figure revenue mark, and what key lessons she learned about hiring the right people
  • Why frequent meetings, checking in with the team regularly, and sharing praise for big wins is crucial for the success of Tammy’s business
  • How Tammy learned to strengthen her communication with her team and repeat the same messages over and over
  • How having a regular meeting cadence has helped free Tammy’s time up and allow her to disengage from the day-to-day to focus on long-term strategy
  • How Tammy learned to trust in her own leadership skills, and how that confidence helped set her up for success


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