Holy Moly, I’ve Been Writing This Site For 20 Years

I started blogging one weekend day in May 2002 on a lark. I had several friends with blogs back then, and I thought I’d try my hand at it. Only I didn’t have anything truly original to say on politics and current events, which is what other blogs I knew about were doing. So I decided to write about travel and miles and points along with an eclectic amalgamation of offbeat news. I focused on what people came to me for help with and just things that amused me. I was writing for myself, not for anyone else.

My original blog site is still largely operational, showing 2003 content. I can’t access the original 2002 posts, but most of those are archived at ViewFromTheWing.com. The earliest posts I still have copies of are from late May 2002 but I haven’t searched for the first few weeks of the blog on the various online archive sites.

My Original Blog

In the beginning I’d get 30 visits a day. The very first link to this site came from legal blog The Volokh Conspiracy. Within a year I was getting 500 a day, although there were exciting spikes along the way — Glenn Reynolds of Instapundit would link to me regularly, especially for my coverage of the TSA and the early bumper stickers I created to Impeach Norm Mineta as Secretary of Transportation (the TSA had been part of DOT before it was moved to the newly-created Department of Homeland Security, by the way I still find the use of ‘Homeland’ to be creepy). The tagline for the stickers was “Liberty & Security Not Bureaucracy.”

I don’t think I was getting 2000 visits a day regularly until I was about 4 years in. One thing that helped me jump to even that level were links from my boss’s blog and an opportunity to guest blog for him.

When I look back at my posts even from those first few years I’m not super proud of them. 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. In 2005 I even declared what I wanted for Christmas and a reader sent it to me. (One of only three reader gifts that I recall, I’ve appreciated them but please no gifts!)

Back then blogs interacted with each other more than they do today. Blogging was a conversational medium. You linked to someone’s post and shared why you agreed or disagreed with them. That’s how traffic was built. That formative experience for me has a lot to do with why I credit where I find things, and why I try to send traffic to blogs (by including them in lists of links) when I feel like they deserve greater attention.

This Blog is 100% Me, But it’s Only Part of What I Do

Long time readers know that I never went full time with blogging. As some of the other sites 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 also write this blog; started an award booking service; help put together the Freddie Awards; consult with financial institutions on the travel and loyalty industries; and even serve as an expert witness in federal criminal trials.

I keep extremely busy, but it’s doing all of the different things that I love. Meanwhile I continue to build this blog. Everything I know or believe above the theory of the firm? I do the opposite. Along the way I became a husband and a father.

Fortunately 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. Not that it even has to for me to write it. This blog started without any ads at all. GoogleAds didn’t even exist when I began. After a month or so Glenn Reynolds paid to take down the ad placed there by my first site host, Blogspot. After 7 months Randy Petersen offered to host my blog. But it wasn’t until 2004 that I had an ad up. “BlogAds” were selling on my site for $40 per week, and I told Randy he could keep it all to defer hosting costs and the technical help his team had given me to get things set up.

After more than five years of blogging I was making $250 a month from the site. It wasn’t long after that I was making $750 a month. I’m very fortunate to have done well since then, but it began simply as a labor of love and stayed that way for years. And in doing well I’m better able to remain ‘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. Instead I just keep spouting off (as some of you would say) and if people are interested they’ll keep reading it, and fortunately people have and that’s the main reason I’m compensated for the work I do here.

Some Lines That I Draw

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.

United ran a preview flight of their first Boeing 777-300ER with their new Polaris business class in it for media. There was no opportunity to buy a ticket on this flight, which is how I’ve gotten onto various inaugurals — buying a ticket like anyone else — so what I do in cases like that is make a charitable donation equal to the value of what I’ve received (even after accounting for any tax benefit).

In order to take the United flight I had to buy a ticket to Chicago and a flight home from San Francisco, and pay for a hotel room. I also donated the cost of a first class ticket between Chicago and San Francisco.

Last fall I went to Richard Branson’s Moskito Island with Bilt. I was reluctant to take the three days away from my wife and daughter, a resort without them isn’t actually fun for me, but I was interested in what Bilt was doing. And I made a donation to cover my portion of the trip’s value.

Status comps aren’t something I’m looking for either. I was once offered free Hilton status and I declined.

I don’t seek better treatment from airlines or hotels because of this blog, however I have occasionally let an airline know I’d like to take photos, because I don’t want to run into problems and get arrested. It’s never led to better service (or if it was better than it would have otherwise been, it’s occasionally still downright awful). There have been a few times where hotels Googled me.

  • Oddly at the W Doha my upgrade wasn’t as good as what many Platinums were receiving

  • At the Park Hyatt Vendome the marketing manager came out to greet me. On that stay I received the lowest category room they can assign when using a confirmed suite upgrade award. On my other stays confirming suites I’ve always done better! They told me if I wanted a better upgrade I’d have to pay for it,

    I asked whether a room ‘like the one I had last year’ was available. I was told yes — and that I could have it for an extra 100 euros per night. I declined. While some would consider the room to be worth it, I was perfectly happy with the room I was assigned. I don’t consider a single room, usually, to be a suite but it was more than adequate for my needs.

W Doha

There are a few things that I have taken. If I attend a briefing event I usually skip out on the social stuff, I’m tired and introverted and probably want to do something else it’s not so much the ethics of a nice dinner. However I have no issue taking a sandwich in a conference room to make things a working lunch. Likewise if I’m meeting a hotel executive in one of their hotels it’s not practical for me to be the one to pick up the check, though I’m usually the one who buys under ordinary circumstances.

By the way I don’t think there’s anything wrong with sponsored trips – for many it’s the best way to develop unique content and bring it to readers. I’m fortunate not to need to do it. And with as busy as I am the last thing I want is to go where someone else wants me to go, and spend time doing things someone else wants. The most valuable resource I have — now that I’m a dad, even more so than before — is my time.

For Better Or Worse It’s 100% Me

I don’t have a staff. I write everything myself and have only had about half a dozen guest posts over the course of 20 years, usually a unique experience or perspective. That means I also have no editor and nobody to bounce things off of. I’m just me and I do the best that I can to write content that interests me (the only way I could possibly still be doing this after 20 years) and hopefully engaging content and do it in a way that let’s me sleep well at night.

I still write the way I did 20 years ago, as though nobody is ready (probably not even family and friends except when I pester them to). I forget that isn’t the case, and am often surprised when something I write reverberates around the industry. In some ways that makes me better (I don’t pull punches) but in some ways probably makes me worse.

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 suppose if I were to ruminate on my biggest blind spot it’s the comments. I wish sometimes for higher quality comments and less trolling. But they say you get the comments you deserve, and I take responsibility for that.

I’ve never been comfortable really doing anything about it, either, I’m too stuck in the early 90s era of the internet when it was supposed to be this bastion of free speech and democratization, and I’ve also seen moderated comments sections too often used as a way of hiding disagreement from what the authors have written, hiding when people point out that they’re wrong. I worry I’m not about the temptation in any given case, so I’ve only been comfortable editing or removing comments that get extremely graphic or violent or that disclose non-public information about private people.

So what does this rumination over 20 years of blogging really amount to? That I’ve had a blast doing it, that no one will stop me from getting to the keyboard each day today and in the future, and that I appreciate everyone who reads what I write whether they enjoy it, are better informed from it, or become infuriated by it. I’m so 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 »

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  1. While I can’t say I’ve read all your blog posts in 20 years (but at least 16-17 years of them), i’m pretty sure i’m among the longest reading readers and do remember quite well your previous incarnation and those bumper stickers.

    Proud to be your host and even more proud to be one of your readers. the things that you reference such as typo’s and proofing are exactly what i enjoy seeing in your stream of consciousness of this topic. #pure+unfiltered

    Count me along with others here who intend to read you for the next 20 years and beyond. #bravo

  2. Congratulations, Gary. Twenty years is an amazing amount of time to keep at anything, let alone maintaining a blog with frequent, high quality posts. You’re making the world a better place. Thanks.

  3. Congratulations! I’ve been reading your blog for over a decade (scary to think too) and got on the track it back deal for a million miles a decade plus ago. Now with 2 kids I don’t use much of the info you post (and don’t have a spare $8000 to risk of crazy mileage schemes like I did when single) but still read you regularly. I hope you’ve made enough out of the site to pay for all your future first class travels.

  4. Gary – I’ve been a travel enthusiast for roughly the same period you’ve been blogging and I ran across your articles early on (circa 2003) and have been a generally silent fan ever since. I love your blunt, independent, intelligent, and “old school” style and hope it never changes. Thanks for giving much more than you probably realize. I’ll be your fan for the next 20 years (then I will reevaluate). -Ryan

  5. It’s an amazing blog! It entertains and informs everyday and I don’t even travel. Your mix of subjects is awesome! One question out of curiosity: how many average daily visitors today? If it’s a state secret or you want to avoid a humblebrag, no worries! Thanks!

    PS: haven’t read the comments yet. If the question already came up, my apologies!

  6. Congrats! I’ve been reading daily for years now, and learned a lot. Thank you!

  7. I’ve been reading (and commenting) for a long time, Gary. I’ve always signed up for anything related to travel, and over the years I’ve winnowed the list down to about 5 blogs. It was great fun to read how you started and what your philosophy is … I really respect someone who just lays it all out there every day, come hell or high water. I do cringe at some of the commenters, but nothing can be done about people who have no lives and get their jollies out of writing nasty comments. Here’s to another 20 years!

  8. Gary! All those figures OMG! You deserve it! You rock and thanks for opening a whole new world to me!
    I’m glad they all don’t comment at the same time! I’d never get any sleep LOL!

  9. Congrats and many thanks Gary for the ****ton of miles via tips I’ve learned from you over past 2 decades. Been with you since BankDirect days! Reading yur posts is part of my unwinding at end of day .

  10. Big congrats & thanks to you for opening the world to me! It has been an amazing trip and you very much deserve credit for it! My immense thanks!

  11. Congratulations on reaching ‘el segundo piso’ (the second floor, as we call the 20 years mark in Venezuela). I really enjoy and appreciate your work. With a blunt math i’m sure i’ve been an avid reader (less of a commenter) for at least 6 years! (time flies! literally).

  12. Congratulations Gary. I started reading when I semi-retired to Indonesia & began commuting between Jakarta and Chicago. I figured there had to be a better way to do this & I needed to learn how. I continue to read your blog as compared to others I have sampled for the same reason I started: what used to be called “decision-making information.” My only commodity is my time & your blog gives me the greatest value for the time I spend reading it.

  13. Congratulations and THANK YOU for all the valuable information you put out. Your writing has enriched my travel and my life. My family, friends, and I have benefitted by tens of thousands of dollars thanks to you. These experiences of enhanced travel make memories that last a lifetime.

    Case in point: Just last week I proposed to my girlfriend at The Bodrum Edition on a five-night stay that cost 200,000 Bonvoy points (and we got a suite upgrade). The knowledge you imparted helped me pick a romantic getaway…and she said “yes!” Thank you!

  14. Gary, this thread is at 66 comments now. That’s a lot!
    What was the most popular, most-commented topic?
    Just curious…

  15. Wow, I probably speak for a lot of readers when I say this makes me feel old haha. I started reading you, OneMileAtATime, FrugalTravelGuy, and ThePointsGuy in 2009 when I graduated from college and was broke but wanted to travel. I was very fortunate that when I had no money, the big credit card bonuses started to drop and for the next 10 years, I got the travel the world on someone else’s dime. When I have kids, one day I will tell them, “Yeah when I was 22, I was flying in First Class, eating caviar, drinking expensive champagne, and taking showers in the sky haha”

  16. Gary,

    Been reading you since 2010. You’ve been great and one of the most trusted blogs out there. I will say that this particular blog is one of my favorites!

    Thanks 🙂

  17. @ Gary. Found your blog many years ago back when there were actually some very good “deals” to be had for miles and points without having to mine. I started with OMAAT but quickly lost interest in his reporting (much too personal) and switched to your blog never to go back.
    Best of luck to you and I wish you continued success.
    BTW, from a quick scan of the comments all the usual suspects (trolls) aren’t raining on your parade. Perhaps even they recognize your commitment and success.

  18. Correction: It’s been so long ago that I may be confusing OMAAT with ThePointsGuy. Either way I find your blog more informative for my needs . . . and entertaining.

  19. Props on making it for 20 years. I don’t always agree with you but I respect your opinion and you do the best analysis of any points and miles blogger I know. More please.

  20. Congrats Gary, it has been an honor to know you all these years. Hope I run into you again in an AA Club someday.

  21. Wow! What a wonderfully informative post, especially for many of us “newbies.” Thank you for your forthrightness, integrity, and willingness to share. Also, best wishes for another productive twenty plus years.

  22. Congratulations gary! I am also a daily reader of your blogs and even get it emailed to different emails in case I miss something! Very entertaining and informative. keep up the good work.. God bless you !

  23. Sincere congrats on your 20 year blog anniversary!! In my household, when we speak of trusted resources, it’s common to hear things like, “Let’s see what Rombauer says we do with this round steak,” or, “Let’s look up what Jacques Barzun has to say about this,” and, “Check out Leff before we confirm our itinerary.” I’ve been a daily reader of your blog since it’s launch, and across the years was a devotee of many, including Rick Ingersoll, Emily and Mr. BowTie, Summer Hull, Ariana, Brian, Greg, Ben, etc. My mornings used to kick off with FlyerTalk and “my bloggers.” Now? Most I don’t frequent, but I’ve remained a fan of yours because your writings are a national treasure of content, help, details, and encouragement. I will remain a daily reader for as long as you continue to post, and thank you always for what you do.

  24. I’ve enjoyed your blog even before I realized it was gleff’s baby.

    It’s sort of become more like The Jerry Springer Show than it used to be, but that helps pay the bills and keep open and vibrant a channel of communication that still provides miles/points value to
    me from time to time.

    By the way, Mike Tyson isn’t being prosecuted for the JetBlue incident.

  25. Hey Gary, congrats on your 20 year blogging career and here’s to 20 more years! I appreciate your back links to TWG over the years and the great work you do at Freddie Awards 🙂

  26. Congratulations and Happy Anniversary, Gary….I appreciate all of your efforts, on the blog and personally. I can’t imagine where I would be today, or how far I was “left in the dust” by the the whole Points & Miles thing prior to discovering VFTW. My wife and I can’t thank you enough — we have *consistently* saved tens of thousands of dollars in flights and hotel stays from SFO to Europe and Asia.

    (Maybe one day, I can thank you and take you to a favored sushi restaurant of ours, without having to go to Tokyo.)

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