Dave Weininger's passing

I stopped writing blogs after my last one, the one where I pointed out that some in the MD world aren’t paying close attention to the scientific principles of test and verification, mainly because there was so much resultant negativity. Of course, that’s nothing new in my career! But at OpenEye we’d started in earnest on Orion, our cloud platform, a journey that’s been rewarding but all-consuming. Write laments that really don’t do any good or go make something you really believe in? Easy choice. It’s one my erstwhile mentor, David Weininger, would have approved of. Dave, who died on Wednesday morning (prior to the election results!), never had much time for communities, other than those freewheeling ones he created for himself. And yet, or perhaps because of this, he had more impact in the field of chemical informatics than anyone since, well, Kekulé.

If that sounds like hyperbole consider this: In 1975, in his classic book, “The Periodic Table”, Primo Levi, chemist, Auschwitz survivor and probably the best science writer of his generation, lamented that there were only three ways to name a molecule: its chemical formula, which was lacking any sense of atomic connectivity, a common name that, whose origin was either obscure or hard to decipher, and that molecule’s depiction, which was a poor substitute for a language. He died shortly before SMILES was invented by Dave but sometimes I like to imagine what a meeting between the two of them would have been like: the Italian, Jewish polymath and the American, Jewish polymath, entertaining and entrancing each other, ending with Dave drawing chemical structures and writing their simple, elegant SMILES strings on some napkin that Primo then tucks into a pocket. It would have been one for the history books because Dave did make history, not just with SMILES but with canonicalization, SMARTS, Daylight fingerprints, his insights into the importance of databases rather than file formats, and so on. But it will be SMILES that ought to put him in the history books. He deserved to be; he’s the only person I’ve ever met who really was touched by genius, someone whose name might be known a hundred or three hundred years from now.

I’m not going to attempt to tell the story of SMILES, Daylight or even Dave; I expect there are others who will do that, including, apparently, a film effort in his latter days. But I would like to share some of my memories, in particular the advice he freely dispensed, sometimes crazy and sometimes life changing. When I heard the sad news that he would not be with us for much longer it forced me to write down those aphorisms and I was really shocked as to how many there were- and how influential some of them have been, especially in shaping OpenEye.

The most important one, in fact one of the principal reasons there even is an OpenEye, came as he and I were driving to Socorro- about two hours from Santa Fe, for no other reason than to visit a roadside diner there. I’d been in Santa Fe just a couple of months since my “Escape from New York” at the end of 1995 and Dave was allowing me to crash at Daylight for a few weeks. He turned to me and said, out of the blue, “You know, if you really believe in something, really believe, then you have an enormous advantage over most people, because most people don’t really know what they believe. It’s such a huge advantage that you almost can’t fail. However, you don’t get to control the time scale of that success.” Of course, I did totally believe in shape and electrostatics as a way of capturing molecular identity and it was and continues to be an enormous advantage. And I was successful, and it did feel inevitable. And I am suitably shocked that that was twenty years ago! Right on all counts.

I keenly observed what Dave had done at Daylight and really OpenEye was an attempt at reproducing that business meme but without someone with his charisma or genius. I liked that Daylight was liked, I liked the idea of toolkits to empower people, I liked that everyone had offices but had lunch together, I liked the idea that you didn't have to take investment money from anyone- you could survive and thrive by just making things. Here’s a collection of his comments that influenced the formative years of OpenEye:

1) “The idea is that you plant your flag in the ground and see who rallies round. Someone always does and they become your friends and colleagues.”

2) “Never sell anything to someone who doesn’t need it. Yes, you get their money but you won’t get their repeat business and that’s what you really want”

3) “It’s not complicated: You make something for someone and if they like it they come back and next time do a bigger deal”.

4) “If you want to live and work outside the ‘system’, then you have to live on your wits. But that’s ok”

5) “Santa Fe’s a place that’s always rewarded creativity, in whatever form. People think of it in terms of art and so on, but why not programming?”

6) “Licensing schemes are just there to keep the honest people honest; there will always be some bad actors, that’s just life, but don’t stay up late worrying about them”

7) “People always say to me, ‘Dave, Daylight’s great, you could be the next MDL’, but then I tell them, ‘Have you looked at MDL? Do they look like they’re having any fun? Why would I want to be them?’”

8) “There’s this idea that to be successful you have to grow and grow and that’s what success means: growing. But I like the idea of ‘right-size’, that there’s a right size to any company and you just have to find it and stop there”

9) “If you are in business why write grants? They take a lot of time, time you could be spending writing code, you don’t know if you’re going to get them and by the time you do you probably want to be doing something else!”

10) “Don’t get into a pissing match with a skunk”

11) “It’s better people underestimate you” (Thanks to Jeff Blaney for this one)

12) “Don’t worry if people don’t buy something. I always feel they can buy now or they can pay more later!”

That’s basically how and why OpenEye became OpenEye. We never took investment, never wrote grants, didn’t obsess about licensing schemes, don’t pressure people to buy something they don’t need, we’re still trying to find our “right size” but only after some real soul searching where we realized that “Daylight-size” was not “OpenEye-size”. Our bigger accounts have nearly always come from us selling something small, then a bit more, then eventually, “Ok, how much for everything?”. And, yes, I do regularly remind myself that it’s ok if someone doesn’t buy something from us, they can pay more later!

There were other, more technical things I learned: the idea of a constant API that you stand behind for always, i.e. requiring you to think deeply about design so as to get it right. The idea of the API hiding the implementation so that you can change that at a later time. The idea of a molecular description not as a file format but as something more formal- he always referred to SMILES as a “language”. I always wanted that for 3D shape – still working on it!

Some of the things I remember aren’t work related but made me laugh or laugh and think. Dave always thought one of the best jobs you could have was as a florist- “Everyone loves flowers so who’s ever not happy to see you?”. He didn’t see how anyone could be a dentist! Another: “Airports are essentially happy places; everyone’s on the move to go to see someone they care about or to be a place they want to be.” Apparently Dave sometimes missed connecting flights because he would become so engrossed watching people! He loved movies and had a great entertainment system. One of the things he liked to do was to synchronize the food being eaten in the movie with you actually consuming that food- e.g. if it’s “Bladerunner” you better have some cheap noodles ready. Try it!

There were bigger life-work observations. One of the most profound and, given the move to open offices, least appreciated is his philosophy on work environments. As Dave put it, “You know most people think you go to work to, well, work and you come home or go to some quiet spot to think. I think that’s completely backwards. We come together to think, we go away to work.”. It took me a while to really get the depth of this and only then because I was lucky enough to have collaborated with Andy Grant in the UK. I used to travel there regularly and Andy was always super-keen we sit down and write code. I was naturally a bit jet-lagged (7 hours!) and would protest that it was sitting around talking that I really appreciated. It was one of the few really contentious arguments Andy and I ever had and yet one day, years later, he came to me and admitted he now saw the light. Those conversations with him and with others in that great group of modelers Dave Leahy had put together were immensely functional- we really did ‘think’ together. There was always time, later, for writing code. Come together to think, go away (even if just to an office) to work. Of course, Dave would go to some Caribbean island to ‘work’!

Another concept he’d observed that I’ve increasingly come to see the truth of is the concept of “self-permission”. His view was that sometimes people want you to give them permission to do something they really don’t have to ask about. As he reminded me, “For instance, you asked me permission to leave Columbia and come out to Santa Fe and do your thing. You didn’t have to ask but you felt you should ask”. I’ve observed this since then and it’s helped me a lot to not be dismissive (“Why are you even asking?!”) but to try and be as graceful as Dave always was with such requests.

Dave really achieved things, he finished projects. He was an exemplar of the Steve Jobs’ aphorism that “real artists ship”. He always referred to that phase of pushing something through to completion as “leaning” on something. “Sometimes you’ve just got to ‘lean’ on something, you know?”. Of course, Dave was a big guy so it was an easy image to get. Also he tended to work in ridiculously long jags of time, something I’ve never been able to do.

The last “deep thought” he shared with me came, I think, in the parking lot of the original Daylight building in Santa Fe- the ex-home to unwed mothers with all that great karma and the place I initially bunked when I came to town. He said, “You know people always worry about the future, where they’ll be in five or ten years time. I don’t know why they do that because how do they even know who they will be then? I’m not the same person I was five or ten years ago and I don’t expect I’ll be the same person five or ten years time”. I often think of this in the context of how Dave essentially abandoned cheminformatics. I think he had done all he wanted to, but more than that he’d just become a different person.

I also think a throwaway joke of his, wherein he used to paraphrase Newton with, “If I can’t see very far it’s because I’ve giants standing on my shoulders”, wasn’t entirely a joke. When you start something you have all the time in the world (or so it seems) and you can see so far. Then, as time goes by, you get pulled in so many directions, accrete responsibilities and duties that you really don’t get to look up as much, and when you do it’s hard to see further than the next meeting or the next deadline. I don’t think Dave enjoyed that much and I don’t think he wanted to be some senior, respected, legend of the field.

Last two, predictably enough on death itself. I remember him announcing as axiomatic, “You know life is intrinsically unfair because at the end you die- what’s fair about that?”. The other has taken me much longer to appreciate, “The one thing that really sucks about getting old is not dying, it’s having your friends die before you”. At the time I hadn’t had many close friends die so I didn’t really agree with him- I mean, couldn’t you just get new, younger friends (like me?). Now, years later, in particular for me with Andy and Takehiro Ohe dying, I realize what he means; how the death of a friend is like a piece of you disappearing that you never get back. So it goes with the passing of Dave Weininger.

They were magic times, those early days in Santa Fe. His fighter jet, him bringing Douglas Adams to a MUG meeting (he’d met him years before on a yacht vacation and had stolen his towel!), MUG meetings, the Daylight ACS booth, trips to Downtown Subscription (a coffee shop that was neither), Horseman’s Haven, the star parties, his world’s-best blackberry pies, the orange crushing machine, the molecular statue at the new Daylight building, the way he was always happy to receive a guest and dissect the world from a new and interesting angle. He was once described as someone who could walk into a room full of people he didn’t know with the confidence that only comes from assuming everyone would love him- and they usually did. He wasn’t perfect, that’s for sure, but he was a remarkable man, one who lives on in many of our lives, our work and our businesses.

I once thanked him for all the help he’d given me. He looked at me quizzically, and asked, “What help?”. When I went down the list he listened and then just shrugged, smiled his big smile and said, “Well, pass it on”.

Preserved Comments

Ant, So many true thoughts about a great man. He taught me so much even when I resisted at first. - Yvonne Martin

Thanks Ant. Weininger's work will always be a touchstone in the history of molecular design, one of those simple-in-retrospect things that really transform the field. A memorable tribute. I still remember Ed Regis' description of both of you in "The Info Mesa". - Ash Jogalekar

So many great learnings in there. Many thanks for passing it on Anthony. - Jonas Boström