Lemonade’s Very Own Da Vinci Code
Shai is a Gift That Keeps on Giving!
Over my career I’ve met with some legendary leaders — people like Jeff Bezos, Steve Jobs, Jack Welch and Eric Schmidt. Admittedly, my time with each was fleeting, but based on all that I know I’d say this:
If I could choose between any of them and Shai Wininger as my cofounder, I’d choose Shai every day of the week.
Our IPO put this into sharp relief.
Going public is an exercise in introspection. It involves months of cataloguing everything the company has built, committing it to writing, having an army of lawyers check and double check every word, number and graph, and then putting it to the public for their verdict. That’s enough scrutiny to engender self-reflection in anyone.
Not that I needed an IPO to appreciate Shai, but the process crystallised things for me. Alongside many others, I spent months working on the IPO prospectus, the investor deck, and the roadshow video. At one point in the middle of the hullabaloo it dawned on me that — as I wrote to Shai at the time — I seemed to be compiling “a legally approved account of everything you’ve done.”
At the risk of selling myself short (not something I’m often accused of), that just about sums things up.
Lemonade has hundreds of amazing employees, many wonderful partners, the backing of the world’s best investors, and yet… And yet the one most truly irreplaceable asset of Lemonade is Shai.
Walter Isaacson wrote a great biography of Leonardo Da Vinci. In an interview he explained this was the pinnacle of his biographical writing, because Leonardo defied conventional distinctions between art and science. When Da Vinci saw a bird, his mind went to the physics of heavier-than-air flight, the biology of muscles and tendons, the optics of perspective, and the interplay of motion and emotion, and he used these to create both proto-helicopters and breathtaking art. Therein lay his genius.
When I heard Isaacson deconstructing Da Vinci in this way, it struck me how much his description applied to Shai too.
I’ve worked with some amazing product people, artful designers, great software architects, formidable engineers, organisational gurus, process devotees, marketeers who can craft a narrative and others who can position a brand. Never have I known someone who possesses all of these qualities.
Shai does, and therein lies his genius.
Shai can hold court on the chamfer of a dialogue box, the hue of its colour, the message it conveys, the tone in which it does so, the font in which it’s rendered, the algorithm that generates it, the app in which it’s displayed, the architecture that delivers it securely at scale, and the people, processes and org structure needed to pull these all together, countless times each day. The upshot is a user experience that’s been thought through to the nth degree, a design that’s pixel perfect, messaging that’s on point every time, and a finely honed tech stack and organisation.
That results in incredible speed and efficiency, but the productivity gains are besides the point. The real step change emerges because this level of conflux produces a whole that is greater than the sum of its parts. It’s not just that one brain can do the work of several — it’s that when all of these converge in a single mind synapses fire, connections are made, and — with apparent effortlessness — novel creations take form.
It’s a change in degree that amounts to a change in kind.
Insurance isn’t the first industry with a Shai-shaped imprint on it. In 2010 Shai cofounded Fiverr, where, in 2013 they gave the ‘gig economy’ its name.
Once is a fluke, twice is a pattern.
I’m resisting the temptation to label Shai the Leonardo of Lemonade. While I like the alliteration, I know he’d cringe at the very comparison. But warts and all, he is the most extraordinary professional I’ve ever worked with, and there is something Da Vinci-like about him. There just is. I don’t always agree with him — the power of our partnership lies in our yin and yang — but on a wide range of topics I defer to him: “my opinion is different”, I find myself saying, “but I trust your opinion more than I trust my own.”
Shai’s extraordinary skills are packed into a humble, straight-as-an-arrow, caring and deeply ethical friend. In Hebrew Shai means a gift. That captures how I think of my cofounder nicely.
