I got a hangover. No, not in the traditional sense, but in the dizzying way it feels when half your world celebrates the double vaccination and no mask, and the other half, across the world, mourns death and not an ounce. of light at the end of the tunnel. The privilege of watching this unfold is like playing the worst game of musical chairs, except some seats are clouds and some are just rows of knives.
For technology, the questions we will be discussing are more important than whether “this conference will be virtual or in person”. Instead, we are now trying to figure out what the future of work and education will be like for the second time in a year. The United States is reopening and that means a lot of the culture of our work will be rewritten. Going from an individual state of mind to a collective, more distributed world will be more difficult than taking off a mask and popping an aspirin.
Start-up founders, new and old, are about to start making decisions about how to lead in this changed world. They will have to consider things much more substantial than if the free lunches came back. More serious questions abound: how to give flexibility and responsibility? How to fix the universal toll on mental health? How do you provide equal opportunities between remote and in-person employees? What happens when half of your workforce can participate in happy hours while the other half is in a locked city?
Naj Austin, the founder and CEO of Somewhere Good and Ethel’s Club, told me about intent this week. She talked about how much easier repainting something is than reinventing the whole process, but the latter has the potential to disrupt a lot more than the former. It got me thinking back to the office and how the frictionless option might not be the best option in the long run.
I’ve learned that the best founders embody this philosophy and choose the toughest bucket. It stands out when you are intentional about recruiting, returning and the potential relief that comes with the option.
In the rest of this newsletter, we’ll cover stock market volatility, the origin story of Expensify, and what a founder learned after being rejected by YC 13 times. As always, you can support me by subscribing to Extra Crunch and follow me on Twitter.
What goes up must go down
The edtech public market is on this genre fire this week, with many stocks cutting stock prices by nearly half from their 52-week highs.
Here’s what you need to know: Alex and I have written about how public market carnage is expected in edtech, an industry filled with pandemic moguls. We predicted bullish VCs will stay bullish, and the market correction is upon us.
In September 2020, Larry Illg, CEO of Prosus Ventures, told us that edtech was filled with “tourists” and “trendy money,” which made it difficult to assess companies and find responsible bets. .
“It’s pretty dangerous,” he said. “We have seen over the years in the geographic context at different points in time that people are drawn to India or are drawn to Brazil and they start pumping money then two or three years later , they come out with their tails between their legs. “
In addition, two SPACs, two IPO and SoftBank updates:
The origin of expenditure management
Expensify has managed to become a leader in the expense management market, with 10 million users, just 130 employees and, of course, an upcoming IPO. For these reasons and many more, this is the latest company in our EC-1 series. The first opus, written by Anna Heim, went online this week.
Here’s what you need to know: While managing finances seems like a pretty straightforward business, the origin of Expensify was much more chaotic. Think about the culture of P2P hackers, consensus decision making, and, as always, an Uber angle. The origin story explores how a motley team created a unique expense management system.
Deep dives continue:
We move on to TC Sessions: Mobility, this year’s virtual dive into the world of transport. Book your general admission pass for $ 125 today, and I promise you won’t regret it.
Among the growing list of speakers at this year’s event are GM Vice President of Global Innovation Pam Fletcher, Scale AI CEO Alexandr Wang, Joby Aviation Founder and CEO JoeBen Bevirt, Investor and LinkedIn founder Reid Hoffman (whose special purpose acquisition company just merged with Joby), investors Clara Brenner of Urban Innovation Fund, Quin Garcia of Autotech Ventures and Rachel Holt of Construct Capital, co-founder and CEO of Starship Technologies Ahti Heinla, Co-Founder of Zoox and CTO Jesse Levinson, Community Organizer, Transportation Consultant and Lawyer Tamika L. Butler, Co-Founder and CEO of Remix Tiffany Chu and Co-Founder and CEO of Revel Frank Reig.