“Realizing my dreams of seeing the world without taking on massive amounts of debt.”

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Welcome to the next interview in our interview series where travel bloggers share their insights on having Big Travel with Small Money!

Miles & Points Interview: Jeffsetter

Jeff  travels over 100 nights a year and writes Jeffsetter to share his experiences.

Jeffsetter – Interview with Jeff

Jeff in Alaska, 2008

How and when did you start collecting miles and points?

I started collecting miles while on a college trip to Kenya to film a documentary following American doctors teaching heart surgery techniques to Kenyan doctors.  After watching my brother earn enough points for Big Travel as a traveling consultant in the early 2000s,  I tried to emulate his success by signing up for a Northwest WorldPerks (and a passport) before that first International trip.

I nearly earned enough miles for a domestic ticket and became excited by the prospects of becoming a frequent traveler and earning free travel opportunities.  I got more serious about the hobby around 2007 when I started using a Northwest airlines branded credit card to earn miles for my business expenses.

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

I started my blog after returning from my honeymoon in October, 2012.  Prior to that point I had been posting travel stories on my personal website since 2005, but these stories were mixed in with other interests and lacked a planned focus.  Moving to a dedicated blog allowed me to consistently post about travel in a singular spot and work on building an audience… and posting about an epic 2 week honeymoon was the perfect way to launch the new site.

As for what is special about the blog, I would say that it is special in a few ways:

  1. I put a lot of effort into each post to make sure it’s as accurate as possible and thorough (this is why I only post 3-5 times a week)
  2. As a marketing agency owner by day, I try to dissect promotions from the eyes of the marketer who is running the promotion.  This provides a completely different perspective than we are used to seeing.
  3.  Since I am very technical, I also like to dissect the technologies that power the travel industry and use that to gain insight into why things work the way they do.  As I work on building up a service called Free World Traveler, I hope to give even more technical insights into travel.

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

Reimbursable expenses.  While most people say credit card bonuses (still a great technique for earning miles), I find that the most sustainable method for earning miles is by using miles earning cards for reimbursable expenses.  What is a reimbursable expense?  Pretty much any time you spend money that is reimbursed by a third party.

For me, this is a an advantage of being an owner of multiple small businesses.  Many of the expenses of owning a business can be a major source of miles earning.  For example, there are tremendous opportunities to earn miles for spending money with Google AdWords.  I have also earned miles by paying phone bills, travel expenses, web hosting fees and business dinners using a miles earning credit card.

While I realize that’s not an opportunity available to everyone, there are more opportunities than you think. If you are comfortable paying up front and then being reimbursed through an expense report, this is a huge opportunity.

What’s your most memorable travel experience?

It’s a tie between getting engaged to my wife Amanda in Sydney, Australia and then traveling around Australia and New Zealand to celebrate and our honeymoon in Mauritius, Munich, Berchtesgaden and Paris.

The Australia and New Zealand trip will always have a special place in our hearts because it was the first step of the rest of our lives together.  It also was the 6th continent I visited, which helped me accomplish my goal of hitting all 6 inhabitable continents (Antarctica will come at some point) before the age of 30. Adding New Zealand, the most beautiful place I have ever been, to that trip was just icing on the cake.

Our honeymoon was tremendous as well, packing in Mauritius with a European stopover which included going to Oktoberfest in Munich and enjoying the Bavarian town of Berchtesgaden.  Putting my points and miles knowledge into action on this trip helped us upgrade our travel accommodations to a whole new level of awesomeness.

Jeffsetter – Interview with Jeff

Oktoberfest in Munich

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

Most of my family and friends are indifferent to the hobby.  Some are inspired by the crazy trips I can take using points and miles, but most others fit into two camps: 1) those who tell me why that would never work for them/how I’m lucky I have these opportunities (to which I say that I don’t believe in luck) and 2) those who think that it’s a cool hobby, but they don’t want to invest the time to learn how it works.

I respect any and all opinions around the hobby, but don’t let any of it deter me from realizing my dreams of seeing the world without taking on massive amounts of debt.

Jeffsetter – Interview with Jeff

Playing Golf

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

I use the ITA Matrix tool for paid flights and Expert Flyer for award flight redemption.  Kayak is a good tool as well.

For hotels I first search on TripAdvisor to see positive/negative reviews and then either look at the points program website for award redemption or use hotels.com when the hotel is not part of a loyalty program (since Hotels.com has their own loyalty program, I can still earn a bonus on those stays).

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

Probably the times when I earn bonus points for doing something that I was already planning to do.  For example, earning bonus points for a certain number of stays during a period of time when I am traveling on business.  There’s nothing better than earning extra bonus points for something I was going to do regardless of the promotion.

Another area where I didn’t expect to earn points and miles is to pay down my mortgage.  You CAN earn points and miles paying your mortgage if you play your cards right (and use some sort of combination of gift cards, debit cards and ACH withdrawals).  Since the exact tactics surrounding this type of earning change often, I won’t go into them here.

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

Never redeem your points unless you get 2 cents per dollar in value or you have a great reason.  I personally kick myself every time I think back to the time I redeemed 135,000 skymiles for a $1,200 ticket to Chile in 2010.  I had so many miles and I was so stupid with how I used them.  For me, it’s not about getting free/inexpensive travel from your miles.  It’s about sticking it to the man with each redemption ;).

Putting it more lightly, it’s about maximizing your value for miles as opposed to using them because you have them.  Sometimes that means paying for a hotel because the points redemption is too high.  It often means paying full fare for domestic flights while you save miles for international itineraries.

The 2 cents per dollar rule helps me make a quick assessment of whether something is a good deal or not.  That does not mean all miles and points are worth 2 cents, though.  You can often get much more value out of points than that.

Jeffsetter – Interview with Jeff

New Zealand Glacier

What would your readers be surprised to know about you?

I like to create websites about random topics of interest or just for fun.  I operate the largest Bodyguard website in the world and have worked as a bodyguard in the past.  I have other sites dedicated to all kinds of random topics.

I also host an annual BBQ every year called Porkapalooza and last year we consumed over 100 pounds of Barbecued pork goodness!

Any parting words?

You CAN travel internationally inexpensively!  If you are unsure about a trip you are hoping to take or the destination, try looking for bloggers who document their trip to that location.  Chances are, someone has been where you are going and shared their experiences with the world.

Use that to your advantage and decide what is best for you based on that extra information.  I also recommend using TripAdvisor for hotel reviews – you may find some gems that way.

Jeffsetter – Interview with Jeff

Wedding in Sonoma, California

Jeff  – Thanks for sharing your thoughts on having Big Travel with Small Money!

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12 responses to ““Realizing my dreams of seeing the world without taking on massive amounts of debt.”

  1. Nice website! I don’t usually find new useful content on the blogs MMS features, but I like this one. I’m going to Istanbul later this summer and I’m looking forward to reading through all your trip reports.

  2. How do I get an invite to Porkapalooza? 🙂

  3. Great interview.

  4. I love your Wedding in Sonoma photo! You have some interesting ideas for getting more miles.

  5. @Kay – glad you like the blog! I am a bit behind on trip reports, but hope you can find some good information there. You have also motivated me to get it together and post them more often!
    @Jason – You are always invited!
    @Tara – Sonoma is so amazing! So was our photographer of course.

  6. @Jeff – well done & nice blog. So good to meet you at BAcon and thank for all the help at BAcon as well. It is amazing to me, like Daraius and the rest of the gang, the quality you can only find in the blog world. Keep up the great work! – Rene

  7. Hi Jeff,

    I love your site. I will bookmark it and visit once a week.

  8. Ok, I got to be the naysayer on a couple of points. First, with never redeem points for anything less than 2 cents per point/mile. I agree that is a good rule of thumb in determining whether you are getting good redemption. I disagree, however, with the advice of never redeeming unless you are getting 2 cents per point. People need to determine for themselves how much they value their points compared to a dollar. Frankly, I value a dollar a hell of a lot more than I value my points. Points are easy to come by and rapidly lose value over time. I have no problem redeeming points for less than 2 cents a point because I do more with the cash I save than hoarding miles that are only going to quickly lose value over time.

    Second, I wish I had reimbursable business expenses. Damn you who do! 🙂

  9. Good point, Jeff. Points = currency. Do your homework and make sure you’re getting value from your points. Sometimes it makes more economical sense to pay with a good credit card than to use points. Often I’ll choose a clean Motel 6 for $60 though I could stay free at Hampton Inn with 30,000 points.

  10. @Scott – I can understand your point of view, but I still think it’s sound advice. It’s not always possible or smart in all instances to hold out for that value, but it’s an easy litmus test for anyone wondering if they are getting value.

    Most of my redemptions are from anywhere between 1.5 cents per point to 7-10 cents per point. If you hold out, you can get it. But like any advice, your mileage may vary.

    I would prefer to give advice that your points are valuable and make sure you get that value than say “burn baby burn” with your points. There are exceptions of course, like when Hilton devalues their chart, but in those cases you often have a grace period to spend the points before they get devalued.

  11. You look quite constipated in your alaska pic! Must be those salmon sashimi

  12. Can you direct me to your resources on earning points to pay down mortgages? I have been trying to figure this out for quite some time with no success!