Introduction
What if the startup myth comes true? The macro picture of Slack. The 3 stories of A Slack Story. Why now? Find the beginning.
June 20, 2019 – 8 am in New York where the New York Stock Exchange (NYSE) is preparing to open. 6 am in Yellowstone where I wake from a restless sleep.
It's the day Slack shares start to trade as WORK on public markets, and I’m on a family vacation with spotty wifi.
So I'm up before the alarm. I check in. The orders I carefully set the night before to turn my speculative Slack shares into real US dollars are missing.
No panic. I have a backup. I set them up again, step by step. The numbers I type into the empty boxes on the screen both unreal and too real. Those sell orders poised to slightly change my life and the life of my family. I have no clue what to expect. It’s tense.
Zoom out
Now zoom out here for a sec with me. Pull back to the big picture.
The years of 2010 to 2022 marked the largest bull market of fundraising in human history. There was simply no better time to raise money for a new speculative venture, perhaps ever. If you had the right story, the right team or the right metrics, money was incredibly cheap and easy to get.
“This is the best time to raise money ever. It might be the best time for any kind of business in any industry to raise money for all of history, like since the time of the ancient Egyptians. It’s certainly the best time for late-stage start-ups to raise money from venture capitalists since this dynamic has been around.”
– Stewart Butterfield, Is Slack Really Worth $2.8-Billion, Apr 16, 2015
And nowhere was money cheaper or easier to get than in software.
"Software is eating the world" wrote the prominent venture capital firm Andreessen Horowitz (a16z) in the Wall Street Journal’s 2011 article that laid out their theory and became received wisdom.
Every company was becoming a software company because every part of every company ran on software or was touched by software. Banks were software companies. Manufacturers were software companies. Advertising agencies and nurses and farmers and drivers all of a sudden were parts of software companies.
And it was also somewhat true: software was eating the world, and is still. “The future is already here, it's just not very evenly distributed,” wrote William Gibson and that phrase has stuck with me as it perfectly describes how changes moves through society.
As computers ran an increasing number of the processes of organizations, the software called business-to-business software became the most attractive of all the speculative venture investments. Software ran payroll. Software ran project management. Software ran the doors of the office and the inventory of the snacks and the ordering of furniture and the coffee machine and the HVAC systems to keep the coddled employees comfortable.
Smaller or richer or younger or more innovative companies generally led the way toward Gibson’s uneven distribution of the future, but all companies were on a similar path to more software. And the path’s progression showed no sign of changing or slowing. Organizations kept adding more software for narrower niches or slower-to-adopt areas of the business. New companies got invented. Very little was untouched or untouched for long.
I know because from June 5, 2013 to June 5, 2020, I worked at a company called Slack Technologies that was at the forefront of software eating the world. My five official roles at Slack gave me a bird’s eye view into the changes happening – the huge sums of money exchanged, how the work of entire national economies transformed, how people, their relationships and workplaces and identities were being revolutionized by software. That’s the big picture here.
Zoom back in
Okay, zoom back in to that morning in Yellowstone and the personal picture.
I’m at the kitchen table of the cabin. The minutes count down to the opening bell of the NYSE. I check the orders, again, again. Everything is ready. I have spent years working at startups, including one I founded and failed at for 6 years. I have spent my personal savings and borrowed and paid off loans and lived with risk for a long time, all in pursuit of a dream of success. I take a breath, and let it go. The hour ticks over and it starts.
My screen refreshes and the numbers have all shifted. The orders are filled, the shares transformed from hope to dollars, the dollars more than I have ever considered holding.
In those moments, what happens? The world has changed for you, for your family, your future, your relationships.
What do you do when the startup myth comes true?
That question – and all the questions that preceded it to get to that point and followed after – I will try to answer in A Slack Story.
It’s actually 3 stories
In the following chapters I’ll try to knit together 3 stories that I believe provide some inside perspective into the times and places where Slack lived and where software was eating the world.
The first story is a big economic story. I mentioned that above in the zoom out: the businesses, funding, fundraising, venture capitalists and capitalism that helped create hyper-growth companies like Slack that ended up worth $28-billion dollars in less than 9 years.
The second story is a comeback story. Slack didn’t start as a success. It started as a failure riddled with burned cash, layoffs, disappointment and tears. Then, nearly the same band of outsiders regrouped from that failure, learned a totally new industry, and transformed a failed video game into a blockbuster workplace tool.
The third story is a personal story. It’s my story as the ninth person to join Slack. It covers a journey of 7 years through 5 jobs and multiple continents and many airports. It’s a story of relationships and doubts, rollercoaster emotions and learning to do what needed to be done by often just doing it.
My intention in all 3 stories is to peel away the media coverage and hype to hopefully reveal some of the magic that made Slack a global phenomenon and huge success.
Some chapters will describe how we did things in details, and share some lessons we learned. Some chapters will sketch the big changes happening in the world around us. Some chapters will reflect the smaller changes happening on my journey, for me and the many people I cared about.
Throughout I’ll try to include source materials and multiple voices in addition to my own. Many of those voices will be from folks who I worked with at Slack. They’re the primary sources. They were in the room when decisions were made. They are an incredible group of bright, humane, funny and talented people.
Together I believe these voices will tell a untold story.
So, why now?
For a few years after I left Slack I considered writing about the company and my experience there. I didn’t act on that consideration until after Stewart Butterfield, the guy who hired me and the former CEO and co-founder of Slack, had left at the end of 2022.
By then most of the other folks I had worked with and considered essential to my experience had also left. In short, while those folks were still with Slack I felt loyal to them, and telling the stories of our journey would have felt a bit like telling tales out of school.
But now that’s over. The company is a different organization, acquired by Salesforce in July 21, 2021, and now part of a company with 50,000+ employees. It’s changed, man, like everything changes.
And with that as context, let’s get started. Find the beginning.
Up next:
A first memorable talk with Stewart Butterfield at Northern Voice, 2009. A connection from a mutual friend. A failed game called Glitch. A newer new thing called Slack.
I’m excited to see this unfold!