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.
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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)
11 Mar 2026
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)
4 Mar 2026
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)
Who has been a guest on A Slack Story Podcast
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James Sherrett
Johan Butting
Eee Mee Yah
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