Marty Weiner and Nick Caldwell on scaling, failing and the future of social
When scaling a company, it’s important to remember one key thing: according to former engineers-turned-tech execs Marty Weiner and Nick Caldwell, that thing is to make the mission you give your software team more interesting that Super Smash Bros.
Weiner and Caldwell worked together at Reddit for two years between 2016–2018. During that time, they were tasked with taking an engineering team through hyperscale — growing from 20 engineers to 140 to around 2,000.
Caldwell, who has just joined interactive fitness platform provider Peloton Interactive as its chief product officer, recalls his surprise upon joining Reddit that there were engineers sitting in the corner playing games, and trying to master every character from Nintendo’s enduring crossover fight series.
“As a manager you can’t really get mad about that, but you have to ask yourself: Why are these folks so excited about Smash Bros and not excited about working on one of the best websites that’s ever been created?”
Caldwell and Weiner have spent a long time reflecting on this and other aspects of the human side to scaling a tech company. They’re in the midst of writing a book on their collected experiences.
Their main conclusion has been that you don’t start companies by writing code and a database. Instead, you set out tried-and-tested processes that help with managing expanding teams.
Within three years, 92% of start-ups fail, with 43% failing due to issues of scale, according to Weiner.
Speaking together in front of an audience gathered at cloud native service provider Civo’s inaugural European conference in London last month, Caldwell and Weiner said they hoped their advice might save some of these companies from failure.
So where does Super Smash Bros fit into this? Caldwell says the reason the engineers weren’t engaged was because no one had explained what their part in Reddit’s mission or overall success was to them.
Mission, says Caldwell, “comes down to getting every single person in the organisation to understand how they fit into the overall mission, so that they get more excited about that than playing Smash Bros.”
Their session, coming to TI soon, outlined the five key steps the executives used to build Reddit. It explained everything from how to devise mission and vision statements to setting objectives, measuring results, creating organisational structure, and execution.
Their concluding remarks were to go fast, but remember the human, “because people are the most valuable part of your organisation, and also the best part about being a manager,” said Weiner.
From engineer to manager
After the session ended, TI grabbed the tech and business influencers for a coffee — taking the opportunity to teach them how to order an Americano with milk in English.
I wanted to start by asking Caldwell, who worked his way up at Microsoft from software engineer to general manager, and Weiner, a founding engineer and architect at Pinterest who became Reddit’s first CTO, about the challenges they faced in transitioning from engineer to executive.
“It’s not something we got taught in school, how to be the manager of an executive team. You’ve got to fake it till you make it and get some mentors very quickly!” says Weiner.
“The second thing I learned is that things generally work in predictable and logical ways — electrons and how they unite with a transistor — that’s very well known, very well documented. But humans? Humans are really hard.”
“I studied child psychology and marital psychology, and that helped me a lot,” he added.
For Caldwell, the biggest challenge was figuring out how those non-engineering roles, such as marketing and IT, came together to make the whole process work.
“When you are an engineer you think, or I thought, that coding could solve everything. Then I went to a Microsoft launch where they bring together top performers, and I met with people outside of engineering.”
“I met this lady who was on a eight-person legal team, who was responsible for about $1bn of revenue from patents that Android had violated. That really opened my eyes to realise it wasn’t just about coding. All these other functions play a really big role.”
“You have to learn a little bit about all those other skills to be an exec. It’s about horizonal leadership — it’s not about your function it’s about learning how to work across all the other functions.”
The trouble with X…
Less than a year ago, Caldwell was working as a general manager at Twitter [now X], where he led a cross-functional team of 2,000 people.
So, what does he think of the changes his former new boss made in his short time at the social media giant?
Weiner, a passionate advocate of social media — particularly his own (he still looks at Reddit and used Pinterest to design his house) — says that he’s come off the microblogging site and is now working out how best to use Threads.
“I’m done with Twitter. We were looking at this from a scale-up perspective and how we built Reddit. I mean, he’s good at building rockets, but we’re just watching him make the exact same mistakes that we’ve seen other start-ups make,” he says.
Caldwell’s response is, typically, more measured.
“I still think Twitter/ X has a lot of potential so I hope the guy can figure out how to operate a social media company at scale. Because, as Marty said, they are struggling and tripping over a lot of the same ground that Reddit and the old Twitter had already overcome in terms of how to make their business model work…how to grow and retain users.”
“Right now, it’s not looking good — they are going through a lot of pain rediscovering things that were already known. Instead of investing in growth, scale, recent technology, and expanding internationally.”
“But I do hope that they manage to figure it out because, as much as I like Threads, it doesn’t serve the same needs as Twitter used to serve — its entertainment driven, an extension of Instagram — whereas Twitter is all about what’s happening now in the world.”
“But I hope they can bring back the mojo. Because of the changes that they’ve made to the core product, it’s a little bit difficult to connect to some of those communities and engage with conversation. It’s got very difficult.”
Black twitter exodus
One community that appears to be leaving the platform in droves is Black Twitter, a virtual community of Twitter users exploriing Black culture which also gave rise to movements like #BlackLivesMatter.
The social network has reportedly experienced an explosion of hostility and racism, over the past couple of years and then Musk’s tweaks restricted the number of tweets users could read in a day, which works against communities with fewer blue ticks.
Many influential members — from TV showrunner Shonda Rhimes to actress Keke Palmer, and podcaster/YouTuber Desus Nice — have deactivated their accounts in response, creating a digital diaspora in search of a home.
One new challenger in the microblogging sphere is Spill, currently in beta stage and invite-only, set up by two former Black Twitter employees, Alphonzo Terrell and DeVaris Brown.
“Our thesis was if we could build a platform from the ground up that caters to these groups, these culture drivers, and then solve the core problems that they’re facing, that our community is facing more specifically, that would make for a better experience for everyone,” Terrell said in a recent interview.
It’s a space that Caldwell says that he’s already enjoying.
“Spill is like a very narrow slice of Twitter, for the Hip Hop community. And I really enjoy that. You know, when you have really small social networks centred around a particular topic, they tend to be much more exciting and positive and engaging places,” he says. “It’s when you get to scale that problems start to occur.”
Another community Caldwell is keen to support and scale is the black software community, specifically in his capacity as a board member of /dev/color, a global accelerator for black software engineers trying to get to the next level.
“That organisation has had quite an effect on its members. You join a cohort of about five or six other people, and they become your ‘accountability servants’ — your cohort that makes sure you follow your goals. Everyone in my group eventually got promoted to either the VP or the C-Suite.”
But for Caldwell, the true ambition, as ever, is success at scale.
“We have 500 members, but more broadly the industry has millions of people, there’s still a lot of work to be done there. We need to see a higher level of diversity at scale.”
Read our interview with Wikipedia founder, Jimmy Wales
Subscribe to our Editor's weekly newsletter