Mostly It Worked

Harold Montgomery

Hi David,

I got your recent email about your book and thought it was a wonderful compilation, and a noble impulse on your part – thanks for doing it and thanks for the opportunity to participate. I read the stories with great interest. Each one brought back a flood of long-buried memories from our happy days together at the GSB. That two-year interval was without doubt one of the great highlights of my life. I would do it again in a second. I continue to marvel at the quality of the people we knew and their subsequent accomplishments and adventures. I count many of our colleagues as lifelong dear friends even if distance separates us. Whenever I travel I try to look up someone to renew a long-dormant connection. My thanks to those who have indulged me in this idiosyncrasy.

I have been living in Dallas since 1985, got married to a wonderful woman in ‘94, raised two terrific and inspiring children who are now grown and live in NYC and Winston-Salem, NC. We miss them, but we have reinvented ourselves to meet the opportunity of this time of life when we are healthy, alert and willing to engage with life further. My wife of 31 years, Kaysie, is now the Lower School Librarian at St. Mark’s, the all-boys school with which we have a had a productive multi-generation relationship. I recently bought my 7th (yes 7th) company which is an advertising app for local retail. Very cool application and well-positioned to benefit from the enormous strides that AI is making in marketing and communications. The rate of change in that area is at least astonishing and keeps me on the steep part of the learning curve every day, which is great.

When I look back on the GSB, I recall we were just barely connecting two computers with Kermit or some such program. I have to confess that I pretty much didn’t get where all that would go over the years since. I recall really sweating out buying a fax machine in 1987 thinking it was a fad!

I sometimes wish I had waited about 3 years to attend the GSB (nothing personal, of course). That would have put me in the class that spawned EBay and other companies. Not that I would have been insightful enough to jump on board – after all, I did turn down a job at Microsoft after GSB. Ooops. Just one of a number of obvious multi-million dollar opportunities that I successfully avoided. (Bitcoin at $0.10 anyone?)

I am not sure I have all that much of interest to impart – I prefer to let my scars do the talking for me. There’s plenty of those. I will tell you all about each one in excruciating detail someday, but you will have to buy the beer

(NB: Bring the Amex with no spending limit, you will need it). If I have any distillation approaching insight or wisdom to offer from all the experiences gleaned from my most important job – being husband and father, or my (distant) second most important one – a 35-year tour of duty as an entrepreneur, it might be a quote from Norma Lear: “The three most important words in the English language are ‘Over And Next’. When it’s over, it’s over. The sooner you move on the better.” Good advice for sure.

In fact, most of what I have done since B School can be summed up in three words: “Mostly, it worked” or perhaps “surprisingly more difficult” works as well.

In business, sometimes I think the three most important three words are “We got funded!” – definitely in the top 10. Right up there with “Git ‘er Done!”

The three-word stricture applies to life as well: “I’m with you” (M 28:20) is a good one. (OK, that’s a contraction to fit the paradigm, but still legit.) Top quotes 5 for sure. The number of times that faith was all I had to hang on to are too many to mention here and fall into the category of “things I learned I would rather not know.”

I bought a company in India,and grew it. That was interesting in the same way that Sir Ernest Shackleton’s 2+ year saga of endurance, grit, optimism and seal blood while being marooned in the Antarctic was interesting: better to read about than to live through. I don’t even need three words for that one: “Don’t” will do. As one older woman said to me at a cocktail party – “Oh honey, there are two things you don’t want to miss in India – the Taj Mahal and your plane home.” I thought quietly to myself: “Where were you before I bought this company?”

I dealt with people all over the world on that deal – India (obviously) London, Japan, Singapore, Finland (no, really), Norway, Hong Kong, and Moscow (!). That last one is unthinkable now, but I was in Moscow 4 times and the people I dealt with there were wonderful in every way. They have all fled Putin’s self-destructive misadventures in Ukraine. I will be forever grateful to our classmates (David Jaffe, Jeff Hamrin and others) who were profoundly helpful in that deal – each of them played a key role and the company would never have reached its zenith without them. I am especially and eternally grateful to Mark Houghton-Berry who was a true believer and supporter from the start and did all he could and more to help. Mark and Megann were always helpful and supportive. It was a privilege to know them better and I admire and respect them both deeply. Also, Laird Cagan who was a friend, confidant, advisor and thought leader at every turn. In short, one of the finest people I have ever met or been privileged to know and an all-around prince. I’ll never be able to thank Mark and Laird enough for all they did to promote our success. Three words: “Admiration, respect, gratitude.”

It took eight years, but we achieved a stable level of activity and profitability despite life-threatening events thrown at us annually. Suffice to say that India is not an easy place to do business. It’s a land of awesome opportunities and equally awesome hazards which are almost impossible to avoid entirely. If nothing else, there’s the government which has a love-hate (mostly hate from what I could tell) attitude toward business generally and foreign business/businesspeople in particular. As long as the money is going their way, you are their best friend. But if the money stops, you are a greedy foreigner preying on innocent Indians. My three words for that: “What the F***!?!?!??”

I went to India 40 times – three words: “Qatar Airways B-Class”. I traveled extensively throughout the country, often to places that had not seen a white person since the British left. That’s not a joke, actually. I am in the photo archives of hundreds if not thousands of Indians who wanted their picture taken with me. Perhaps they thought I was John Lithgow. Not only that, but everywhere I went there was invariably a ceremony of some sort and often involving cutting a cake or other ceremonial act I had to perform. I once cut 6 cakes in one day on a swing through the countryside.

If you need travel tips for India (three words: Rambagh Palace, Jaipur) or Italy (three words: Cipriani Hotel, Venice), let me know. (Perhaps we’re stuck on countries starting with “I”. Maybe Ivory Coast is next.) My wife and I traveled to Italy 30 times to plan a series of YPO conferences there. We went almost everywhere north of Napoli and it felt like we ate everything in the process. We’re going back again this Thanksgiving. Three words: “Vino, Gelato, Pasta!” or maybe “Vino, Gelato, Michelangelo”. I think I like that one better.

Did I mention that my key talent is second-guessing myself?

That, an ability to see around the corner about an inch more than the other guy kept me out of trouble as an entrepreneur. It certainly wasn’t my mastery of accounting for operating vs capital leases. Not to discount the role of blind luck.

The companies I had were in the payment space and have all been small. They were more or less successful. One was public. Three words for that: “Uh, no, thanks” Payments has been a good place to be – constantly growing and evolving and therefore forgiving of the many mistakes I made along the way, and receptive to the very few ideas I had that actually worked. Most importantly, I was able to make a living and be home for dinner with the family at 6 pm. Enough travel to be interesting but not burdensome. Three words: “Family is it.”

I have so many happy memories of the GSB and our many fine adventures there – too many to recount them all, but here’s a few: First year talent show, McKinsey Skit, Robert Burgleman’s class, Ben Bernanke’s accounting, Rick Berthold’s small business, dinner parties, parties, the Old Pro, the Dutch Goose, Yosemite with Yang, Daughterty and Yort, Goofy stuff with Breier, the various Europeans in our class who are friends even now, teaching Victor Long to ski at Tahoe, and more. Lots more. Three words for that: “Wonderful, just wonderful!” or maybe “It was beautiful!” Or maybe “I Loved It!” or maybe all three.

I guess the thing I have learned is that you only need three words. Which are the most important? That’s not even close: “I love you.”
You just need three words. The right three.