Slack Equity Regret

Andrew Wilkinson shares a story about passing up Slack equity that would have been worth $100M.

"MetaLab back in 2012 or 2013, we designed Slack. At the time, Slack was actually a failed gaming startup and Stewart Butterfield was trying to do something with the remains of it, trying to build a chat tool.

He comes to me and says 'Hey, I've only got $80,000 budget for this.' I was like 'Well, we'd normally charge quite a bit more, but we really want to work with you, we're big fans.' He says 'Hey, what if we did some stock?'

I said 'No, no, no. MetaLab would go broke if we just took stock, we don't do that.' My thinking was I wanted to get as much cash as possible so I could invest it in my own businesses. What I ended up investing in at that time was my productivity software where I lost $10 million.

Instead of putting it into this money-losing productivity software, I could have made $100 million or something crazy because it was at like a $20 million valuation at that time and it sold to Salesforce for $28 billion."