by James Sherrett
In 2013, I started as #9 on the Slack team. A Slack Story tells the best stories from the 7 years and 5 jobs that followed. The Podcast is those stories in audio form. Plus more to come. Subscribe by RSS with this link: https://api.substack.com/feed/podcast/3721181.rss <br/><br/><a href="https://www.slackstory.com?utm_medium=podcast">www.slackstory.com</a>
Language
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Publishing Since
1/23/2025
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March 18, 2026
<p>Money as MacGuffin: Playing the Tech Lottery Game</p><p>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.</p><p>00:00 Money And startups</p><p>01:25 Salary plus options</p><p>02:15 No upside to sharing numbers</p><p>03:29 Learning the Tech Lottery Game</p><p>05:09 Spotting rocket ships</p><p>06:07 Cap table basics</p><p>08:06 Comparing two acquisition outcomes</p><p>09:23 Champagne Problems</p><p>10:53 Money as MacGuffin</p><p>12:43 What really motivates</p><p>14:50 Thank you very much</p> <br/><br/>This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit <a href="https://www.slackstory.com?utm_medium=podcast&utm_campaign=CTA_1">www.slackstory.com</a>
March 11, 2026
<p>Questions That Remain: Luck, Culture vs People, Leaving Before It’s Time</p><p>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.</p><p>01:38 Luck in Slack's success</p><p>04:26 Luck lessons in life</p><p>06:34 Culture versus people is the wrong framing</p><p>08:26 People build the flywheel</p><p>09:35 Leaving before it's time</p><p>10:54 Seeking a life after Slack</p><p>12:28 Farewell to all that</p> <br/><br/>This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit <a href="https://www.slackstory.com?utm_medium=podcast&utm_campaign=CTA_1">www.slackstory.com</a>
March 4, 2026
<p>Thank You Slack: Seven Years From Employee #9 to a Global Company</p><p>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.</p><p>00:00 A farewell to Slack</p><p>02:06 Why I had to leave</p><p>04:22 Thank You, Slack letter</p><p>05:36 Joining as marketer</p><p>06:49 Positioning Be less busy</p><p>07:55 Launch day signups</p><p>09:00 Customer feedback loop</p><p>14:00 Saying No Nicely</p><p>17:35 Account Management begins</p><p>17:55 Paid launch and billing</p><p>20:35 Offsite, swag and scale</p><p>22:44 Enterprise sales emerges</p><p>25:00 Building the Dublin office</p><p>28:54 Culture and hiring in EMEA</p><p>32:39 Scaling EMEA sales</p><p>34:35 Executive Briefing Centers</p><p>35:52 Innovation Tours program</p><p>38:35 Gratitude and next chapter</p><p>41:35 Final reflections and farewell</p> <br/><br/>This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit <a href="https://www.slackstory.com?utm_medium=podcast&utm_campaign=CTA_1">www.slackstory.com</a>
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In 2013, I started as #9 on the Slack team. A Slack Story tells the best stories from the 7 years and 5 jobs that followed. The Podcast is those stories in audio form. Plus more to come.
Subscribe by RSS with this link: https://api.substack.com/feed/podcast/3721181.rss <br/><br/><a href="https://www.slackstory.com?utm_medium=podcast">www.slackstory.com</a>
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