A Slack Story Podcast

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

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

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

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

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

The Pocket Square Project: Swag off in all directions

In this episode, James Sherrett shares how he created unconventional company swag for Slack. From initial inspiration at Heathrow Airport to collaborating with suppliers and distributing pocket squares as multi-purpose swag, he explores the impact and reception of these stylish silk squares. This off-the-books project showcases the playfulness and high standards Slack aspired to in its executive programs. Sherrett reflects on the innovative culture at Slack, the sense of autonomy, and the joy of injecting a sense of play into his work, all while hinting at future episodes on significant milestones like Slack's public offering.

00:00 Introduction: A Slack Story by James Sherrett

00:05 The birth of the pocket square idea

00:43 Finding the right design

01:51 Partnering with Monsoon Corporate Gifts

02:43 The arrival and reactions

03:24 Covert Marketing operations

04:07 Spreading the pocket squares

06:06 Broader swag strategy

06:55 Standards and challenges

08:50 Conclusion: embracing play and change

Harnessing Innovation: Slack's Journey to Innovation Tours

James Sherrett narrates the journey of how Slack capitalized on the rising demand for Innovation Tours, turning it into a valuable business opportunity. Initially uncertain about the concept, Slack learned that Innovation Tours vary greatly, with companies, government agencies, consulting firms, and specialized tour companies organizing them. By assessing the benefits of these tours through a decision matrix, Slack hosted tailored visits, sharing their company culture and innovative practices. These tours increased visibility and led to significant business deals. Ultimately, the Innovation Tours fostered collaboration and showcased Slack as a leader in enabling organizational change.

00:00 Introduction: A Slack Story by James Sherrett

00:19 The concept of Innovation Tours

00:54 Understanding the demand for Innovation Tours

01:48 Different types of Innovation Tours

03:26 The value of Innovation Tours?

05:19 Slack's approach to Innovation Tours

06:53 A decision matrix for Innovation Tours

09:37 A memorable Innovation Tour experience

14:53 Lessons from Building a Culture of Innovation

18:37 The Impact of Innovation Tours

Reinventing Meetings: The Power of Effective Executive Briefings

James Sherrett discusses some common frustrations with meetings and argues for their potential efficiency when conducted properly. By exploring Slack's approach to transforming meetings into executive briefings, he demonstrates how thoughtful execution can drive business success. He highlights the collaboration between Slack's sales teams, Slack executives, and Slack customers to create effective briefings that help close deals. Key results of Slack's briefing process include a higher win rate for deals and significant contributions to annual contract value.

00:00 Introduction: the dreaded meeting

00:57 The case for effective meetings

01:23 Human nature and meetings

03:31 Steps to better ,eetings

05:04 Reinventing meetings as briefings

05:44 Collaborating with our 3 key groups

08:08 Examples of successful briefings

13:37 Results and reflections

15:33 Conclusion: finding competitive advantages in plain sight

Fumbling Towards Legitimacy: A Senior Technology Strategist at Slack

James Sherrett shares his journey of becoming a Senior Technology Strategist at Slack, a role he describes as initially undefined and nebulous. He recounts how he took on the challenge of defining his new role, like with his previous positions at the company. Sherrett outlines the three primary responsibilities he eventually took on: executive briefing center engagements, investor and partner engagements, and innovation tours. Were there personal and professional hurdles? Some. Frequent travel and the need for self-sufficiency on the road. Sherrett's tries to capture the nuance of becoming 'the Slack man' though he never talked about it. He highlights the importance of presenting a coherent future vision, drawing from experiences and lessons in executive engagement. The episode concludes with a teaser on exploring these executive briefings and the balance between vision and reality.

00:00 Introduction: becoming a Senior Technology Strategist

01:19 Defining the role: challenges and opportunities

02:28 Establishing the hob: Executive Briefings and public speaking

03:11 A Portfolio of Activities

04:49 Embracing the Slack Man identity

06:38 Life on the road and time alone

09:40 Changing beliefs and behaviors

11:59 Selling the Future: lessons from Microsoft

13:36 Conclusion: Working on Slack vision for the future

Returning to Slack YVR: A Journey Home

James Sherrett recounts his return to Vancouver and Slack YVR on Canada Day, 2017. Slack YVR is familiar yet changed, with growth from 1 to 3 floors. We spend some time on the exceptional team that made Slack special, the culture, shared mission, and collaboration that fostered excellence within Slack. Key employees advanced within the company. How Slack YVR uniquely provided perspective and a focus on deeper work.

00:00 Returning to Vancouver: a new beginning

02:40 Settling back into Slack YVR

04:25 The people of Slack: at the heart of the company

07:37 Growth and expansion: Slack's global journey

10:18 Balancing work and travel

11:39 Building new programs and enjoying the work