Redesigning Sales, Work and Money: CEOs of Drift, Upwork and Credit Karma +More
David Cancel of Drift, Hayden Brown of Upwork, Ken Lin of Credit Karma
OK, I'm going to level with you: There's too much good stuff in this week's newsletter. You're not going to be able to watch it all in one sitting. There's the Puerto Rican/Ecuadorian founder who grew strong as an outsider (Drift), the $8 billion-dollar deal that COVID almost killed (Credit Karma), and the CEO who nearly died on the side of a mountain (StockX). Plus, a Fortt Knox alum with an $11 billion software IPO (Samsara). And there's more. Below, I'll give you a flavor:
Upwork CEO Hayden Brown on Flexibility and New Models for Work: CNBC Working Lunch
Upwork CEO Hayden Brown grew up vacationing in an unconventional way, traveling the world on a shoestring budget. Now she leads a company that's offering an unconventional type of leverage to workers, and flexibility to employers, in a tight labor market. Get to know her in Working Lunch on CNBC's Power Lunch:
Drift CEO David Cancel: From Bilingual Outsider to Serial Entrepreneur
David Cancel, CEO of Drift, was born to immigrant parents in New York. He learned English from Gilligan's Island on TV, and learned to fit in by reading a room. Drift is his fifth startup, it's valued at more than $1 billion, and we talked about the journey:
Credit Karma CEO Ken Lin: Learning from a Failed Gaming Business, and the Value of Trust
To mark the 1-year anniversary of Intuit buying Credit Karma, I did a Fortt Knox 1:1 with Founder/CEO Ken Lin. He and I had spoken before, but never at this depth about his upbringing, his other ventures, and how COVID almost sank an $8 billion deal:
StockX CEO Scott Cutler: Mastering Marketplaces and a Survival Miracle
Scott Cutler is CEO of StockX, a company that got big as the trusted marketplace for collector sneakers, and has since expanded into other culture-forward categories. He told me how his experience with market-related companies — and a near-death experience — shaped him:
Forethought CEO Deon Nicholas: AI for Customer Service as Labor Shortages Loom
Artificial intelligence startup Forethought this week announced that it raised a $65 million Series C round of funding. I spoke with Cofounder and CEO Deon Nicholas about how the technology works, and why it's especially needed in a tight labor environment:
Samsara CEO Sanjit Biswas: What Inspired Us to Start an $11 Billion Company
Samsara CEO Sanjit Biswas joined me in a September Fortt Knox 1:1 and shared how he started working on the problem that led to the supply chain technology company's formation:
... and here we are this week, on the morning of Samsara's IPO:
In 2021, Did the Market Learn Its Lesson? On the Other Hand
It's a year that started with meme stocks and crypto soaring, then a crash in growth tech valuations. And so far it's ending with EV stocks and inflation soaring, and another crash in growth tech valuations. So has the market learned its lesson? In my last On the Other Hand of the year, I argued both sides:
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