Time flies when you’re having fun and the last 10 years have been a blast. My life and the miles and points world have changed considerably over the last decade. While some amazing deals have come and gone, we’ve witnessed an explosion of incredible new cards with top-tier benefits… and, in some cases, insanely high annual fees to go along with them. And I left my professional finance career of almost 20 years to freelance, blog, and podcast full-time.
I want to say thank you to everyone who’s followed along, encouraged me, and supported my writing and podcast episodes. I can’t wait to see what happens over the next 10 years… both with my sites and in the world of miles & points.
Here’s a summary of my major milestones from the last decade.
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Launched BaldThoughts.com in 2012
I started BaldThoughts.com to share how my family used miles and points to travel for as close to free as possible. My goal was to inspire other families to travel more, spend less, and live better by using miles and points to cover travel expenses so they could use more of their money to pay off debt and invest in their future.
My buddy David Esquire of Esquire Photography and I were having dinner while waiting for a DBox movie. We were brainstorming ideas for a website name over a few drinks, and that’s how the name Bald Thoughts was created.
One of my first blog posts explained the benefits of AwardWallet to track your miles and points. Even though other sites and apps have come along, I still use AwardWallet today to track my rewards and ensure that I don’t let any of them expire before I can use them.
Attended FinCon New Orleans in 2014
I didn’t know it at the time, but the people I met through the annual FinCon conferences would change my life. The conference is for money nerds like me who love to talk about personal finance and optimizing what we spend (very similar to miles & points, right?). This isn’t an end-user conference like Chicago Seminars or EconoMe. Instead, it’s for content creators to learn how to improve their sites, grow their audience, and learn about the latest apps and brands.
So many of these wonderful people from FinCon are now some of my closest friends. I started attending with the intention of being a better writer for my own site. But seeing their successes as freelance writers convinced me that it was a realistic career move that I could take if I needed to.
Joined BoardingArea family of travel sites in 2016
My good friend Angelina introduced me to Randy Petersen and Boarding Area’s House of Miles team in 2015. Angelina recommended that I join Boarding Area to increase my audience and learn from the many talented writers in the community.
After a year of writing back and forth, I joined BoardingArea’s Prior2Boarding.com site.
Other bloggers joined at the same time, including my friends Jon and Ben from NoMasCoach. We’ve since become great friends, and it’s always great to see them in real life. Eventually, all of us on P2B were merged into the main BoardingArea.com site.
Left the corporate world to freelance full-time in 2018
After 13 years at my former company as a divisional CFO, I said “c-ya” in May 2018. It was a tough decision, but it was the right thing to do for me and my family. Part of leaving my job also included moving our family to Nashville for a slower pace of life, lower cost of living, and to be closer to our family on the East Coast.
Switching to a full-time freelance writer and blogger had its challenges, but it’s been awesome to work with so many brands that I admire. It’s cool to write for brands like Forbes and U.S. News I grew up reading, Investopedia which I used for research when I worked in banking, and The Points Guy and NerdWallet where I learned so much about miles and points in my early days.
Launched the We Travel There podcast in 2018
Also in 2018, I launched my travel podcast called We Travel There. I’m always the annoying tourist that strikes up conversations with locals at the bar, on the bus, and on the street. I ask them about the best things to do in their city and where the locals go to eat. In most cases, they are friendly and love to share their favorite spots… including some hidden gems that most tourists never learn about.
These conversations formed the basis of my podcast. I’ve now released over 230 episodes from cities all over the world. New episodes come out every Monday, and each episode is about 30 minutes in length. We cover both big cities and small towns in the U.S. and from every continent (except Antarctica). We’re on all of the major podcast apps. Take a listen and follow the podcast for inspiration for your next travel destination.
This week’s episode is about the best things to do in Bucharest, Romania, with Edward Sturm of Commit Club. In this episode, Edward and I talk about visiting the Palace of Parliament, seeing the Bucharest fountains at Unirii Square, and exploring the Obor Market, one of the greatest farmer’s markets in all of Europe.
Winning awards in 2022
It’s always nice to be recognized by your peers for your efforts. In September 2022, I was nominated for two Plutus Awards — best freelance writer and best frugal travel blog. For both awards, the nominees were some of the best in the business, including many writers who are my friends.
Although I didn’t win the best freelance writer award, I was happy to see my friend Jackie Lam win the trophy. Honestly, I was a bit shocked to win the best frugal travel blog considering the excellent content the other nominees put out. But I’m very happy to take home the trophy. And, to add a little cherry on top, I won the freelancer of the month award for August 2022 from LendingTree. Very happy, indeed.
Speaking at conferences and on podcasts
As I’ve developed my voice and confidence speaking in front of large groups, I’ve had the opportunity to speak at multiple conferences over the last decade. While speaking gives me extra exposure, the true benefit is being able to meet so many cool people from the audience. I’ve spoken at Chicago Seminars, FTU, FinCon, CardCon, and others.
Additionally, I’ve been able to guest on some amazing podcasts across the personal finance, real estate, and miles & points world. I love being able to share my story to inspire others and share the strategies that I’ve been able to use to travel more, spend less, and live better.
2023 and beyond
As we roll into the new year, I’m in the process of redesigning my site and launching some of the other websites I’ve been working on. It’s a cool way to expand my horizons and learn about new topics. While travel and miles & points are “my first love,” I also love sharing other ways for people and businesses to save money, improve their lives, and maximize their spending.
Stay tuned and subscribe to my email newsletter to be among the first to hear what happens next.
The Bald Thoughts
Thank you again for all of the support and encouragement over the year. I appreciate all of your comments, shares, and clicks on my affiliate links. I couldn’t have accomplished all that I’ve done over the last 10 years without you. Best wishes to all of you for an excellent 2023, and let’s build momentum together to make it the best year yet.