The Story Of How I Began Blogging

by Gary Leff

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. My day isn’t complete until I read your blog. And I don’t travel!
    Most enjoyable peeking into your travel world!
    Thank you!

  3. I have enjoyed your writing for many years. I used to travel for business 40 plus weeks a year and earned 1K status with United. Now that I have retired I travel with my wife and two (2) Westies in our RV seeing that sights that I used to fly over. Keep up the writing for I enjoy reading your thoughts and ideas on travel, hotels and in general the world.

  4. I dislike the coverage of credit cards on this blog. It undermines the claims that coverage is independent and you make enough money elsewhere that you don’t need to make money through this blog. Those credit card posts are monetized – you admit to as much in the legally required disclosure. Why make those posts at all?

    You even link to (in the right hand sidebar) a much better source of credit card information. Doctor of Credit eschews affiliate links to credit cards and thus provides more comprehensive information.

  6. @CERTIFIED, DoC covers the details of offers but rarely provides the sort of analysis that bloggers like Gary does. It’s not enough, as a consumer, to understand that a card has a bonus offer and earns such-n-such points per dollar spent. Understanding why a card has usefulness, especially in relation to other cards or programs, provides me (and I assume others) with value that DoC chooses not to provide (or so I presume).

    If I had a quibble about the CC coverage, I would say that some posts seem to get reposted more often than I would expect or want. But, as Gary stated earlier, the posts here are based on his own interests, not readers’.

  7. I’ve been a fan since the beginning, and probably prior to the beginning on FlyerTalk.

    Here’s to twenty more years.

    Jeff in Toronto

  10. Thanks for doing this Gary. I may not always agree but I appreciate your take and you’re always a good read.

  11. Gary, thanks for all you do and share. You’re directly responsible for many travel experiences of which I could only dream as a kid.

  12. I used to think Gary Leff as a funny kind of guy, meaning not as bad as weird but different. After reading his bio in this article, I have great respect for the guy. He writes stuff single handedly without any employees and having another job. 3 cheers for Gary.

  13. Thank you, Gary! I love your blog, and appreciate personal service (such as answers to e-mails).

  14. I’ve been reading your blog for years and have benefited in many ways but mostly just enjoy your takes and comfortable writing style. I’ve probably sent you a dozen emails over the years and not one has gone unanswered.

    I’ve also sent several sent over a couple of fare deals that you posted, which made my week!

    Thanks for all the help!

  18. I never got a thank you, sniff, sob.
    Oh well, over it.
    I shall keep reading for my ownself
    the best travel life blog ever…..

  20. You helped me over a decade ago with logistics on getting to the Maldives. I appreciate that you share info that both newbies and seasoned travelers benefit from. I love your blog. Please thank your wife for sharing you with us.

  21. Thanks for sharing and keep up the great work! I’m a daily reader and will most certainly keep coming back 🙂
    Just curious, how many hours do you work a week? 😉

  24. @Gary: My friends and I read your blogs every day. Thank you for very helpful info. Unlike “Live and Let’s Fly” (Matthew) who never responded or helped, every time we reached out, we got your responses. My friends and I really appreciate you. Thank you, Gary!

  26. Thanks for doing what you do. I immensely enjoy the blog and it’s the first site I check most days. It’s far more actionable than the vast majority of travel blogs and I’ve gotten incredible value from that fact. IMHO I’d love it if the comment section were policed a bit better; while I understand the general pro-speech posture, many white nationalists seem to take advantage of the policy to post the things here that they can’t elsewhere; and there doesn’t seem to be much of a slippery slope risk to just nerfing those folks. Thanks again for everything, and hope you consider. Cheers.

  27. @Gary Leff I too was a child of divorce. I missed a trip to Galveston as a kid because I had a sore throat. And as they say all my brother brought me back was a lousy t-shirt! He went in March and said the weather was chilly so I didn’t miss anything. We didn’t have a car except the short time my stepdad was there. There were no summer trips. There wasn’t money for anything like that. I went to Sheridan, Arkansas and Durant, Oklahoma. That was the extent of my travels. I felt fortunate when my uncle and my other brother took me to Six Flags over Texas. When I became an adult I wanted to see places I had missed. I felt I was making up for lost time. I went on an airplane for the first time in my forties. The more I have traveled the more stories I have to tell. Good and not so good. So far no major disturbances at the airports or on the planes. I don’t regret any trips I have taken. Some of my family got spooked after Natalee Holloway went missing in Aruba and they didn’t feel comfortable with us taking trips. I figure if a bad situation is going to happen it can happen anywhere. I’m getting ready for a trip to London in 2024. We will be doing a daytrip to Paris on the Eurostar. And if all goes well possibly a trip to Sydney and Melbourne, Australia before our passports expire. Thanks for what you do Gary.

  32. Huge thanks from me too, Gary, you’re the best !!! Also, as one of your fans who live in Austin, I’m still hoping to finagle a lunch (or drinks or coffee) sometime !

  33. Gary. Thanks for sharing. I assumed you may have added some ghost writers lately with so many posts. I’m impressed with your work ethic to the contrary. You are one of my favorite points and mile bloggers. There are a few folks I continue to follow like the dots lines guys and Ed Pizza but you are the only blog I subscribe to. I hope to meet you at some random event one day. #rockstar
    oh and stop the TikTok stuff, my IQ goes down on those posts 🙂

  35. Gary:

    Thank you for all you do. Your blog and Ben’s are my go-to sources for travel info.

    I so much appreciate the logical, rational, analytical approach you take to issues regarding travel and regulation. Even when I don’t agree with you, your rational analysis always gives me food for thought and forces me to examine my own reasoning.

    All the best to you.

  36. Been reading you for years, and you do a mahvelous job, Gary. The blog is always interesting, sometimes annoying … like the reposts from social media or the stories about people urinating on each other … but mostly it’s just great. You should be proud!

  37. I don’t agree every time, but I certainly respect your ability to put together interesting content so regularly while also doing so many other things. I think you’ve figured out how to have a 30-hour day.

  39. You’ve done it your way, Gary, which is quite the accomplishment. I’ve greatly appreciated your efforts all these years and have learned so much from your blog and your emails when I’ve reached out with questions. Replying to readers’ messages is incredibly generous, not to mention helpful to the readers. Here’s to another 21 years!

  40. I applaud you for at least continuing to write your own content. It’s why it is still readable even though your behavior during the pandemic was reprehensible. I honestly don’t know how those of you with a strong public voice in any fashion can live with yourselves after that.

    I’m glad that I never got into this business because, to be honest, I’m not sure if I would have responded correctly, or protect my cash cow like you all (lucky coins guy included) and parrot the corportate/administration/government line regarding vaxxes, masks, travel restrictions etc.

    I started as a travel forum monitor (tfjim) on AOL back in the 90s and, or course, early, early member of Flyertalk. I remember clearly some of the great Catman, Luckycoins, etc trip reports that was the naissance of travel blogging. Who knew that one would be able to make millions by shilling credit cards?!!!

    But as I said, I’m glad it wasn’t me who had to deal with that moral quandry regarding the pandemic. Sad that so many of you (all of you really) failed this generation’s greatest moral test and must live with that for the rest of your lives.

  41. How was this blog (or the author)’s “behavior during the pandemic…reprehensible”?

    What was the “moral quandary” (I’ve corrected your spelling)?

    Bragging about being a “travel forum monitor” or “early member of Flyertalk” is not the win you think it is. To the contrary, it shows you to be a weirdo and a misfit. Well-socialized people weren’t moderating forums on AOL in the 90s; they didn’t even own personal computers in that era. Flyertalk is a place where pseudointellectual people engage in discussions that balloon to dozens of webpages about the size of the cut of limes served in first class predeparture beverages.

  43. I’ve been following this blog since I found out about rss feeds. Before that I followed your posts on FT back when that site was different. You helped me on FT with many a trip. You would PM me every now and then with help, and a few times with a note to not go personal against other members. I don’t like your politics. And I don’t care for the card posts. But in both cases I have a process to deal with them: I don’t click the headline in my feed. Problem solved. I stopped reading lucky years ago when it was obvious that many of his experiences were those that normal people wouldn’t have. The one I remember was a post about a Sheraton in Germany that gave him a huge upgrade supposedly due to status, as well as a welcome gift emblazoned with his blog name. Very obvious they did know who he was. You don’t do that and if you do you disclose it. I appreciate the approach.

  44. @CERTIFIED thank you, my feelings exactly.

    If you read this blog for political or pandemic news or discussions, you’re in the wrong place;

    if you’re sore about Gary’s “reprehensible” behavior during pandemic, there’s something wrong with you.

  46. Thanks, Gary. I enjoyed this post and would like if you could sprinkle in more articles about how blogging has evolved for you, the business aspects of it, etc.

    I don’t know how you find the time to do all this while also being a CFO and a husband and father. Not enough coffee in this world for me to try that!

  47. Thank you, Gary Leff, for authoring your exceptional and perspicacious blog regarding the airline and credit card industry. For your honest and balanced reporting, I recommend American Airlines restore your complimentary ConciergeKey top-tier status for at least ten more years.

  49. Thanks, Gary for this blog and your prompt, helpful replies to every email I’ve sent you, Yours was one of the first travel blogs I started reading who knows how long ago (because I sure don’t remember), I’ve learned a lot and continue to read every day. Keep up the great work!

  50. Thank you for being a blessing to us with your honesty.Your dedication is an inspiration, and I hope the good L0rd will grant us many more years enjoying you labor of love.

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