“I Love…Introducing My Son to So Many Diverse Cultures That He Otherwise Would Only Read About in Books.”

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Miles & Points Interview:   BaldThoughts

Lee writes BaldThoughts to share his tips on traveling for (almost) free and personal finance.

And he’s giving away a $25 Amazon gift card along with 2 United lounge passes on his blog!

Bald Thoughts - Interview With Lee
Lee’s Son, Timmy, Flying Iberian Business Class From Paris

How and when did you start collecting miles and points?

I’ve been using the Chase Southwest card and American Express Starwood cards for about 10 years.  For a long time, I really thought that I had travel dialed in and life couldn’t get any better.  My wife and I have been traveling together since shortly after we met in 2006.

For several years, we would travel at least once a month and it seemed like we were gone more weekends than we were home.  Anna always talked about traveling internationally, especially to visit France, but I always changed the subject because Southwest doesn’t fly there, and I thought it would be incredibly expensive.

I read a few blog posts on Million Mile Secrets and other sites in January 2012 about the now-defunct Citibank American 2-browser trick, so I tried it and earned 100,000 miles.  From that point on, I knew I could make her dream of international travel a reality!

Why did you start your blog?  What’s special about it?

For 2 people who work full-time, have limited amounts of vacation, and are raising a curious 3 year old, our family travels a lot.  Mostly, we do long weekend trips so that we can stretch our limited vacation time across as many trips as possible.

I originally created BaldThoughts to talk about our travels, personal finance, and attending professional sports events.  Although these topics are loosely related, I split these topics into 3 sites…BaldThoughts, BaldFinance, and FlyToTheGame…so that each could focus on 1 of my passions — travel, personal finance, and sports, respectively.

Bald Thoughts - Interview With Lee
Go Seahawks!

Our friends, family, and co-workers think that we spend a lot of money traveling.  But we use the Southwest Companion Pass, AMEX Starwood Points & Cash, and our timeshare to explore US cities and attend professional sports events since 2007.

Our flights and lodging generally cost less than what another couple would spend on a night out to dinner, a movie, and drinks.  The biggest expense we incur is buying the professional sports tickets!

Most travel bloggers think that timeshares are a 4-letter word, but we love our timeshares – Worldmark by Wyndham and Diamond Resorts.  On BaldThoughts I write stories that describe how we incorporate both hotel points and our timeshares into our travel experiences to get the best of both worlds.

Bald Thoughts - Interview With Lee
Diamond Resorts Avila Beach, Timeshare June 2012

The biggest benefit of timeshares that we love is that our friends and family can join us on our adventures and we’re all staying in the same unit so the kids can play while the adults enjoy real conversation over a “home cooked” meal.

What’s the one single thing people can do to get more miles?

Credit card sign-up bonuses are the obvious #1 way to get more miles.  However, you need to have a long-term strategy with your applications.  Have an idea of where you want to go.  And consider which cards will get you the miles and points to get there the easiest and will use the least amount of miles and points.

Once you’re on your way, I suggest diversifying your balances with other cards so that you have options.  Flexibility is key in making your travel dreams a reality since award space may not be available on your preferred airline during the time you wish to travel and not every chain has a hotel in the city that you’re traveling to.

Bald Thoughts - Interview With Lee
NHL 2012 Winter Classic in Philadelphia

What’s your most memorable travel experience?

I’m lucky to have shared so many memorable travel experiences with my wife, and now my son.  For example, we were married at a winery in Solvang, California, which is the 1st place we traveled together during a weekend stay at our timeshare.  Life came full circle for us.

Bald Thoughts - Interview With Lee
Our Wedding at Winery in Solvang, California

However, making Paris a reality for her in April 2013 has been my greatest travel accomplishment.  I used the 100,000 American Airlines miles, 50,000 from Fidelity, and transferred the rest from Starwood to book 4 tickets for us to travel from Los Angeles to New York (3 day stopover for New Jersey Devils game) and on to Paris.

We traveled off-peak so it was only 20,000 miles each in coach there, and 50,000 each for Business Class coming back.  We were gone for 2 weeks and used a combination of hotel points and our timeshare to stay in NYC and Paris for free.

I’ll never forget climbing the Eiffel Tower with Timmy on my shoulders and watching him giggle uncontrollably as he chased the pigeons outside the Louvre.  Timmy was recently featured in a CNN article talking about what age is too young to travel with a child.

What do your family and friends think of your miles & points hobby?

Most of my friends and family still don’t comprehend how we travel so much.  Even though I share with them how I earn miles and points to travel, they probably think I’m exaggerating and am just paying for our travel.

Although I love to travel, the frugal part of me wouldn’t allow such extravagance if we were paying cash for our travel experiences.

A few friends have started to convert into the miles and points game.  One family just earned their 1st Southwest Companion Pass in February and booked tickets before the March devaluation to join us in Orlando.  We’ll be staying in a 2 bedroom unit using our timeshare, which means we’ll have plenty of great bonding time and will save a ton of money on food and drink with the full kitchen.

If his family of 4 was going to buy these tickets, it would have been over $1,700 just for the flights!  Instead, with 2 credit cards, the flights were $40 for taxes and fees, with enough points left over for a weekend adult getaway to Las Vegas.

Is there any tool or trick which you’ve found especially useful in this hobby?

The best tool is AwardWallet, which helps me track our family’s miles and points and makes it super easy to log-in to verify points received and to book travel.  The best trick is really a benefit.  The Southwest Companion Pass allows me to stretch my points so much further because Anna flies for free wherever I fly.

Ever since our son turned 2 years old, and we had to start buying tickets for him, that really started putting a crimp in my Southwest points balance.  Having the Companion Pass means our family of 3 only needs to redeem points for 2 tickets.

What was the least expected way you’ve earned miles or points?

It’s always a nice surprise when you get unexpected points from dining.  We generally only eat out when we travel, so we pick places that look interesting and have no idea that they would participate in the airline dining programs.

I recommend that the 1st thing you do with your new cards after activating is to register them with 1 of the airline dining programs.  You never know when that restaurant with the tasty food will also provide some tasty airline miles!

What do you now know about collecting miles and points which you wish you knew when you started out?

For the 1st couple of years of traveling on Southwest, I didn’t realize that the Companion Pass was good on award flights.  So, we only used the Companion Pass when I bought a ticket, and used 2 award tickets whenever we didn’t pay cash.

I also wish I knew about applying for lots of credit cards to get the sign-up bonuses.  I’ve always maintained a solid credit score, and that’s 1 asset I wasn’t capitalizing on until I started focusing on miles and points in January 2012.  Until that point, I earned Southwest and Starwood points with my monthly spending and having my Dad put his business expenses on my cards.

What would your readers be surprised to know about you?

In my “free” time, I like to run obstacle course races like Tough Mudder and Spartan Races.

The toughest challenge was the GORUCK Challenge.  We started at 9:00 pm and covered 23 miles and several team and time challenges over 13 hours.  We each wore a backpack with 6 bricks, food, and water (about 45 pounds total) throughout the night…with the caveat that our backpack could never touch the ground.

Bald Thoughts - Interview With Lee
Showing Some Grit in the Spartan Sprint Charlotte, North Carolina

Any parting words?

My wife often says that I book too many vacations for our family, but I disagree.  Like most families, we’re busy with work, her MBA program, and normal life responsibilities, so booking vacations ensures that we get to spend time together.

I love exploring the world with my 2 favorite people and introducing my son to so many diverse cultures that he otherwise would only read about in books.

There is no better time to travel than now.  Some other “fire drill” will always come up and your responsibilities will be waiting for you when you come back.  But children will grow up faster than you realize and they’ll reach a point where it’s no longer cool to hang with Mom and Dad.  Show them the world now, while you can.

Lee – Thanks for sharing your thoughts on having Big Travel with Small Money! If you’d like to be considered for our interview series, please send me a note!  

Editorial Note: We're the Million Mile Secrets team. And we're proud of our content, opinions and analysis, and of our reader's comments. These haven’t been reviewed, approved or endorsed by any of the airlines, hotels, or credit card issuers which we often write about. And that’s just how we like it! :)

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