The Story Of How I Began Blogging

Since I write here for you every day, several times a day, and I read comments I feel like we’re in a conversation and know each other. I’ve gotten to know many of you over the years. But there’s also a lot more people reading this website than ever before – around 7 million in the past 30 days alone making this one of the most read travel sites.

So when I saw Ben Schlappig, whose One Mile at a Time is one of my favorite reads, tell the story of how he became a travel blogger I thought I ought to do the same as well. I’ve shared all of the pieces of this over the years, but it may be new for many of you – and since many of you visit daily (thank you!) I figured I’d share a bit of my story.

  • I began an obsession with travel as a kid. My parents divorced when I was very young, and I grew up flying back and forth between New York (where I lived with my mother) and California (where my dad lived).

  • I started paying attention to frequent flyer programs after college, when I began traveling for my work in the D.C. area – and also flying cross country visiting family on the West Coast. I’m the type of person who reads the fine print on things, and I used to read all the materials that loyalty programs would send in the mail (and it was paper in the mail back then).

  • I became pretty obsessed with loyalty programs after earning Premier status on United for the first time, and figuring out how to get upgraded (I’d avoid flying at peak business travel times, and choose aircraft with large premium cabins relative to the total number of seats). I became the ‘go to guy’ on travel and miles within my professional and social circles.

  • So one weekend day in May 2002 on a lark my then-girlfriend (now wife) was over cooking at a friend’s house. I was going to meet them that evening. But I used the afternoon to set up a blog at blogspot. Many of my friends in D.C. had started political blogs but I didn’t have anything really unique to say that wasn’t being said elsewhere in that space. So I thought I’d write about the kinds of things people asked me about all the time.

I started blogging as a hobby 21 years ago. A year later fewer than 1000 people a day were reading it. Occasionally I’d get big bumps in traffic, when I’d write something that a much bigger blog would link to (I got some great coverage from Instapundit and from the Volokh Conspiracy back then). I guest blogged at Marginal Revolution in fall of 2005. But it was always just a hobby.

There weren’t even any ads on the blog for the first couple of years. The first check I ever received from the blog was $750 from ads that were run by Bank of America for the Alaska Airlines Visa. I was six years in before I was receiving $250 a month. But I was getting attention, with my first profile in the New York Times then.

It took me a long time to find my ‘voice’. But it was fun. I’m not naturally a great writer, but I still love the creative outlet and opportunity to express myself. I got to interact with and even to know many readers who share my interests.

Here’s what surprises a lot of people. I never went full time with blogging. As some of the other sites out there became full-fledged businesses, even selling out to corporations, this has remained one of the many things that I do. I still have a job, it’s where I get my health insurance, and I travel for work. (I’m CFO for a couple of university research centers, with a $70 million budget and about 300 employees.)

  • I do not have any employees
  • I write all the content myself (in 20 years I’ve featured a handful of guest posts where I thought they’d be uniquely interesting in a way I couldn’t offer myself, like a solo female flying Saudia business class in and out of Pakistan)
  • And this isn’t my only job.

In addition to full time employment and this website I started an award booking service; help put together the Freddie Awards; consulted with financial institutions on the travel and loyalty industries; and even have served several times as an expert witness in federal criminal trials. There really are criminal trials over miles and points!

Since the blog just one of the things that I do, and everything here is in my own voice, I write on my own terms. You don’t have to like this blog, or like every post, and I respect your opinion. But I speak my mind, I stake out positions, I don’t stay milquetoast desperate to avoid controversy that might push some readers away.

That’s not smart for ‘business’ but I do just fine. I wrote the site for years without any revenue attached. The only way I’ve managed to write here for more than two decades, day in and day out (I did last skip the day, a decade ago, when my grandfather died), is by writing (1) what interested me, and (2) doing it for myself. I write like nobody’s reading, and it isn’t until angry calls come from certain companies that I remember other people are in fact reading.

This also keeps me pretty ‘independent’ in my coverage of airlines and hotels, since I don’t rely on them for access or income. I make money through several ventures outside of this blog, so I don’t need to do anything I’m not comfortable with to earn a living. I don’t generally accept free travel or other gifts, either, however there are events I want to attend for context or content reasons that aren’t open to the general public. When I do decide to attend an event I have a pretty clear approach to those: a charitable donation that offsets anything I’ve received.

Thank you for reading. I appreciate every one of you – the folks that email me (I still try to respond to every message I get), the folks who comment (I even love the trolls), and those who just come by quietly. I have a blast writing this website and no one can stop me from getting to the keyboard each day. I’m genuinely glad I fell into this one weekend afternoon all those years ago!

About Gary Leff

Gary Leff is one of the foremost experts in the field of miles, points, and frequent business travel - a topic he has covered since 2002. Co-founder of frequent flyer community InsideFlyer.com, emcee of the Freddie Awards, and named one of the "World's Top Travel Experts" by Conde' Nast Traveler (2010-Present) Gary has been a guest on most major news media, profiled in several top print publications, and published broadly on the topic of consumer loyalty. More About Gary »

More articles by Gary Leff »

Comments

  1. Don’t know how you possibly do all you do by yourself, but please keep doing it. Your content is more valuable to me than the blogs with dozens of employees

  2. It’s been a nice run since diving into and from the space on Flyertalk.

    I continue to appreciate what this blog does, and that is even as I understand why it also gets some of the criticism it gets.

    May there be many, many more years of this blog being done by you, amigo.

  3. @Ken A While I appreciate your intent and energy behind your CK recommendation, I must adamantly disagree. After all, that’s the whole point, no?

Comments are closed.