“There’s No Better Time to Live Your Dreams Than Now!”

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Welcome to the next installment of our interview series where folks share their thoughts about Big Travel with Small Money!

Miles & Points Interview:   MilesTalk

Dave has collected millions of miles and points.  He writes MilesTalk to give back by sharing his tips for cheap travel.

You can also follow him on Facebook and Twitter.

How and when did you start collecting miles and points?

In 2003, I was already a voracious reader of Flyertalk and wanted to know everything.  But it wasn’t until there was a mistake rate fiasco at the Hilton Bora Bora Nui (formerly a Starwood hotel) that I really got started.

In that case, they let people book $1,000 per night overwater bungalows for only ~$100.  Ultimately, the hotel cancelled the rate, but Starwood apologized with 5,000 Starwood points.

Once I figured out what I could get with Starwood points, I became hooked on accumulating them.  That then spread to a variety of programs.

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

What’s crazy is that I just started it a couple of months ago.

But over the years I’ve done different versions of travel blogging.  I used to run a site called Hotel Magician, which sold hotel rooms and flights and I wrote hotel reviews and travel tips there.

So not new to the game by any means, but it’s my first full-scale site devoted to miles and points.

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

Figure out the one thing you spend the most on and make sure you are using a card that gives you bonus points for spending in that category.  For example, if you book hotels for your business, use a card that gives 2X or 3X on points at hotels.

What’s your most memorable travel experience?

About 5 years ago I took my first trip to Asia.  Using all miles and points we flew to and from Asia in Cathay Pacific’s First Class suites and stayed in a wonderful private villa in Thailand.

I often relate my trips back to how I flew, where I stayed, and what I ate.

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

They think I’m way over the top.  And they probably have trouble following me when I try to explain my latest way of scoring a deal or redeeming for travel.  But they always appreciate the way we travel!  Who’s going to say no to free First Class flights?!

That said, I’ve really tried to get better about explaining in less detail and helping them as much as I can.  I figure, like training wheels, the interested ones will learn to do it themselves.

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

I love ExpertFlyer and I’ve had an account for as long as I can remember.

I’d rather search for award inventory there as opposed to the airline sites just because I can do it more quickly.  But it’s the flight availability alerts and seat availability alerts (sent via email and text message) that save the day.

If I had to settle for less than great routing but know seats might open up later on the route I want, I’ll just set an alert and forget about it.

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

I usually forget I am signed-up for the Rewards Network dining program to earn American Airlines miles.  Sometimes after a pricey meal I get the email a few days later that I earned several hundred or more miles.

Other than that I generally expect the miles I get!

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

How often the programs devalue.

I used to have much more of a saver mentality and now I’m much more willing to let go of miles for a decent redemption.  That’s because the longer you hold the miles, the less they are worth.

What would your readers be surprised to know about you?

Well, they probably already know I also maintain a food blog, I’ll Have What He’s Having.

But they would probably never guess that by day I’m CEO of a mid-size web development company called DG Interactive and a 3D medical animations firm called DG Medical Animations.

I also tweet a lot about venture capital and entrepreneurship on my personal Twitter page.

Any parting words?

I think we have been seeing a seismic shift in the miles and points game when it comes to the best redemptions, namely First and Business Class flights internationally.

So if you are saving up for that dream trip, take it sooner rather than later even if it means aggressively chasing down that last bit of points.

And always make time for travel.  Never assume you’ll make all your dream trips in retirement because you don’t know what the future holds.

There’s no better time to live your dreams than now! Dave – 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!