The New Visionaries: Kakul Srivastava


I’ve only known Kakul a short while, but when we met we somehow interacted as if we’d been friends for a decade. Perhaps that is the result of the two of us thinking about the same things in similar ways for so many years.

About Kakul


Kakul Srivastava

Kakul is the CEO of Tomfoolery, which released work management app Anchor earlier this year. Prior to founding Tomfoolery with Sol Lipman, she worked at Stewart Butterfield’s Tiny Speck, and prior to that she was general manager of Flickr.

The Interview

Stowe Boyd: I like your company’s motto: We believe all work is personal. It starts with a person’s engagement in their own work, but then shifts out to their immediate network of contacts, which I am now calling their ‘set’ (see Sets, scenes, and worlds: understanding social scale in the organization). What’s your thinking on different sorts of social tool support for sharing across sets, scenes, and worlds?

Kakul Srivastava: I think our focus as an industry has been social networking with a capital N — your big networks. I’m constantly running across names from my FB graph or LinkedIn graph who I simply can’t recall. Who are these people? Did I ever really know them? And should I somehow reconnect? But, wow, these graphs have grown, and I can’t help but add more people to them — there are more interesting people to meet every day. And I’m hooked on the hope that by connecting on FB, Twitter etc…somehow. I’l actually get to have meaningful interaction with them. Aside from very rare cases, this never happens. I just get stuck in weird voyeur loop instead.

Turning purpose into meaning, and our intentions into action is what social tools can most effectively help us do.The 1st gen enterprise social networks are simply these large N networks brought to a smaller playground, with mixed results. Though we haven’t focused on our sets very much, I think people have found ways to make them work — IM, SMS, email, even the lowly phone call — help us connect with our closest set, and they do it pretty effectively. It’s the middle ground (your scene) that we have a huge difficulty with, people we know but not that well — how do we deepen our engagement with them, work collaboratively to exchange ideas, create projects, do more/better in the world together? It’s this goal that Anchor (which is fundamentally team-based at it’s core) has been based. A new product coming out soon will help you engage in a similar way with people outside your corporate environment.

SB: You’re the CEO of Tomfoolery, now. Could you share the way that your thinking about social tools has progressed since your days at Flickr?

KS: In many ways, Flickr was a playground, and the social tools we had on the site, a great set of toys for people to invent new games. Our most passionate users were people brought together by a shared passion for photography and the early social internet. (The site began in a game, in actuality.)

SB: The Game Neverending: an IM Community It was quickly transformed into Flickr once photosharing was added, and the gaming side dropped. That’s how I met Stewart Butterfield and Catarina Fake.]

The challenge we’re undertaking now at Tomfoolery is an evolution from that thinking, but with a far more complex challenge. Can you take a group of people brought together, not by shared passion, but the practical necessities of life, (i.e this is a job I do, I have to pay my bills, Julie needs braces…), and create a sense of play in their environment. We spend far more time at work than we do anything else without waking hours. We have to make that time count — and it should be both fun and meaningful.

SB: I would put finding meaning and purpose ahead of fun, although fun is also cool. How can a social tool help people find meaning and purpose?

KS: As big a fan as I am of social tools of all sorts, I don’t think they help us find our purpose. I think we have to do that on our own, in isolation, listening carefully to our hearts and minds. Certainly social tools can help us along in that voyage of self discovery by exposing us to people and ideas that inspire us or make us laugh. Turning purpose into meaning, and our intentions into action is what social tools can most effectively help us do. They can help us infect others with our ideas, and create change in the world. But it’s a all a whole lot better when it’s fun too.

SB: I wrote a post earlier this year that arose from a discussion we had (see Cooperative tools need to become ‘engines of meaning) where I hypothesized the way that an imaginary tool called Koan might work as an ‘engine of meaning’, to use Bruce Sterling’s metaphor. Basically, I was hypothesizing how a cooperative tool might share information across a company without forcing users to join defined groups. The idea is that we could tag ourselves and others with terms like ‘social business’, ‘chautauqua’, or ‘cooperation’ and so could they. So if you wrote a post in Koan and tagged it ‘cooperative tools’ or ‘social tools’ it would find its way to me even though it’s not an exact fit for any term of mine, per se. We’d both be members of a ‘grouping’ — an implicit collection of people that are sharing similar terms when tagging information, and we’d be getting information filters by the ‘engines of meaning’ instead of explicit membership or following. What’s your thinking on that?

KS: I think this is a beautiful model, and in many ways the ideal construct in any organization. I love the flow of it and the simplicity. I also love how it eschews any traditional structures of the corporate organization — hierarchy, divisional boundaries, functional areas…but allows knowledge to flow freely.

The real revolution isn’t inside the company — it’s that the company itself is increasingly irrelevant.Having said that, like many people who were inspired by your post, I struggle with how you would actually create this system. The software part is easy — the actual social dynamics that would drive this behavior are very hard. How would you teach people how to use tags effectively? How would understand that Accounting might be included in Finance, but not the other way around? How would you prevent people from unwisely using tags to gain the widest audiences for their content? At scale, these problems can be solved, but in a corporate environment where effective and efficient knowledge transfer is key, the start-up costs of this system might be too great.

SB: We’ll have to see if someone gets around to experimenting with those ideas. I wonder what happens if IBM directs Watson at being a matchmaker of the sort I waved my hands at in the Koan writer-up. What about the rise of social data mining, and Watson-grade AI? Could they combine to unsnarl that?

KS: All of those are great tools — but they work best when data is at scale. Our challenge with Koan is a start-up challenge.

SB: I know I am a bit hard over about the distinction between the now-mainstream premises and motifs of collaborative tools and the somewhat elusive emergence of looser, inferential cooperative tools, like the imaginary Koan appliance. If you don’t think that is the next wave, what will it be?

KS: One of the insights that we’ve come to is that the premise of how work is done fundamentally needs to change. We imagine these corporate environments (often very large companies) and we try to visualize how they might improve their infrastructure and communication patterns. The real revolution isn’t inside the company — it’s that the company itself is increasingly irrelevant.

The atomization of the corporation is very real and has been discussed at length. What’s discussed less is how increasingly critical our out of work networks are to our ability to get work done. Millennials are more likely than any other previous generations to daily access their outside-of-work networks to get work done. The forces of micro-entrepreneurship are increasing making each of us our own “corporation”, reliant on our outside networks to make things happen. Finally, as our previous work experience becomes increasingly irrelevant to our future work problems, our real asset to bring to any endeavor becomes our network. FB and even Linked In are not capable of meeting these demands. We’ll see the rise of modern, personal networks for work, to allow these worker tribes to thrive and flourish.

SB: Yeah, I wrote a piece recently on how top performers do it (see What top performers do, and how to do it), and the consistent thread is proactively building a network of people that might prove helpful in solving problems in the future, so that when opportunity (or adversity) knocks they can amass a brain trust to help. Is that the sort of thing you mean?

KS: Exactly.

SB: Thanks for playing with me.

KS: This was so much fun…what a lovely game!

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