Questions That Remain

Money as MacGuffin

Money as MacGuffin: Playing the Tech Lottery Game James Sherrett reflects on a career largely shaped by the “tech lottery game” of compensation: salary plus stock options. He spent his early work years in late-1990s online finance media, then in roles helping companies adapt to the internet, then six years running a startup that failed. What did he learn? He declines to disclose his Slack earnings. A number is less interesting than understanding how the game works. Then he describes how outcomes of the Tech Lottery Game vary based on factors like teammates, investors, fundraising strength, and especially cap tables (share counts, ownership distribution, liquidation preferences, and complex clauses). He compares Slack’s cap table and $27.7B Salesforce acquisition with Mobify’s tangled cap table. He concludes that money is a startup “MacGuffin.” Day-to-day motivation came from teammates, customers, and doing quality work. 00:00 Money And startups 01:25 Salary plus options 02:15 No upside to sharing numbers 03:29 Learning the Tech Lottery Game 05:09 Spotting rocket ships 06:07 Cap table basics 08:06 Comparing two acquisition outcomes 09:23 Champagne Problems 10:53 Money as MacGuffin 12:43 What really motivates 14:50 Thank you very much This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit www.slackstory.com [https://www.slackstory.com?utm_medium=podcast&utm_campaign=CTA_1]

Questions That Remain

Questions That Remain: Luck, Culture vs People, Leaving Before It’s Time James Sherrett reflects on unresolved questions from A Slack Story: the role of luck in Slack’s and his own success, culture versus people as drivers of performance, and how to leave before it’s time by building a life to move toward. He argues luck is unknowable but significant. He quotes Michael Lewis on success being rationalized and luck creating obligation to the unlucky. He notes Slack benefited from launching at the right moment amid enabling technologies and market conditions. On culture versus people, he rejects a zero-sum framing, describing a reinforcing cycle where great people build culture and culture attracts great people. He recounts growing less motivated by Slack’s scale and achievements, defining new goals largely outside work. He tells a pre-pandemic story that helped with his decision to leave and plan life after Slack. 01:38 Luck in Slack's success 04:26 Luck lessons in life 06:34 Culture versus people is the wrong framing 08:26 People build the flywheel 09:35 Leaving before it's time 10:54 Seeking a life after Slack 12:28 Farewell to all that This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit www.slackstory.com [https://www.slackstory.com?utm_medium=podcast&utm_campaign=CTA_1]

Thank You, Slack

Thank You Slack: Seven Years From Employee #9 to a Global Company James Sherrett reflects on leaving Slack on June 5, 2020, exactly seven years after joining as the ninth employee, during which Slack grew from $0 revenue and eight employees to over 2,200 employees in 16 offices and nearly $1B in revenue as a NYSE-listed company. He recounts early marketing and positioning work (“Be less busy”), the 2013 invite launch that drew 8,000 signups in 24 hours, early customer development and support, and the shift into account management and the 2014 paid launch with credits, invoicing, and the “Fair Billing Policy.” He describes building teams, opening Slack’s EMEA office in Dublin in 2015, and later leading Executive Briefing Centres and Innovation Tours. He leaves to prioritize the rest of his life, pursuing advisory work, writing, personal projects, and volunteering. 00:00 A farewell to Slack 02:06 Why I had to leave 04:22 Thank You, Slack letter 05:36 Joining as marketer 06:49 Positioning Be less busy 07:55 Launch day signups 09:00 Customer feedback loop 14:00 Saying No Nicely 17:35 Account Management begins 17:55 Paid launch and billing 20:35 Offsite, swag and scale 22:44 Enterprise sales emerges 25:00 Building the Dublin office 28:54 Culture and hiring in EMEA 32:39 Scaling EMEA sales 34:35 Executive Briefing Centers 35:52 Innovation Tours program 38:35 Gratitude and next chapter 41:35 Final reflections and farewell This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit www.slackstory.com [https://www.slackstory.com?utm_medium=podcast&utm_campaign=CTA_1]

Stories I Haven’t Told You (Yet)

Slack Frontiers, Almost Getting PIP’d, and Accepting Less Ambition James Sherrett continues A Slack Story with 3 stories he hadn't told yet. First, how Slack launched its customer conference, Frontiers, starting in 2017 after customers began asking for it. He explains how the conference brought together customers, partners, product, and the Slack team, and how it created business urgency by serving as a deadline, including an on-site executive briefing program by 2019. He shares vivid details from Frontiers and the event’s “Frontiers” name inspiration from a Carl Sagan quote about humanity needing a frontier, noting omitted lines about knowing how to reach “a new world next door.” Second, he recounts a January 2020 warning from his boss, Marnie, that he was trending toward a performance improvement plan. Third, Sherrett reflects on accepting less ambition as he played smaller roles as Slack hired world-class experts to replace functions he initially led. He reframing his trajectory as a generalist pioneer who starts new initiatives until others can do them better. He emphasizes humility, change (“burn the metaphorical boats”), and the value of never underestimating sheer gall. He closes with some thoughts about self-awareness, challenge and selling out to do be the best you possible. 00:00 Intro and Feedback 00:40 Why companies host conferences 01:44 Building Slack Frontiers 03:09 Frontiers moments and meaning 05:11 Almost on a PIP 06:38 Resetting from complacency 07:37 Learning to accept less ambition 10:20 A generalist mindset 12:26 Never underestimate sheer gall 14:06 Finding some self awareness This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit www.slackstory.com [https://www.slackstory.com?utm_medium=podcast&utm_campaign=CTA_1]

WORK on NYSE

Going Public from Yellowstone: Slack’s NYSE Debut and the Reality of Change James Sherrett recounts Slack’s direct public offering (DPO) on June 20, 2019, when shares began trading on the New York Stock Exchange under the ticker WORK, roughly five years after Slack’s first revenue and at a valuation north of $20 billion. Instead of being in New York, he was on a family trip in West Yellowstone with spotty internet, balancing work with family. He describes placing insider sell orders the night before, the DPO mechanics versus an IPO (including immediate insider trading flexibility but greater pricing uncertainty), and a launch-morning panic when his orders hadn’t saved. After spending the day offline biking and exploring with his son, he later catches up on headlines and teammate photos from the NYSE. Sherrett shares Butterfield’s framing of going public as a rite of passage rather than the journey’s peak, then reflects on questions he later received about whether money changed Slack, noting it did through growth, new people, increased conservatism, and intensified competition (especially with Microsoft Teams), while much of Slack’s spirit and customer focus remained. He concludes that the changes weren’t all positive but were overwhelmingly so from his perspective, and teases future stories about finding frontiers, and accepting less ambition. 00:00 Slack goes public as WORK 01:28 Choosing Yellowstone over the NYSE: family, FOMO, and the trip out 03:28 The night before: placing orders and feeling the stakes 04:13 DPO vs IPO: why Slack took the direct listing route 06:09 Launch morning panic: scrambling and the opening bell 07:13 Wall Street movie moment: how the price of WORK got set 08:51 Unreal meets reality: orders fill and WORK starts trading 10:06 Offline celebration: bikes, rivers, and a day away from the news 13:03 Did money change Slack? 15:47 Closing thoughts: next on the journey This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit www.slackstory.com [https://www.slackstory.com?utm_medium=podcast&utm_campaign=CTA_1]