Welcome to Startups Weekly, a new take on this week’s start and startup trends. To get this in your inbox, subscribe here.
When On Deck had to cut its staff twice within a few months, co-founders Erik Torenberg and David Booth . published a memo that promises to pay more attention. This marked the company’s turn to its original customer cohort – founders in need of networking and advice.
Since that day, I’ve been delving into what happened at On Deck, leading to a series of layoffs and a reorientation. We know that producing a community has its challenges. But what are those challenges and how do they manifest themselves outside of workers losing their jobs.
A month later we have some answers. On Deck is converting half of its career services business into a new startup that will launch in October. Torenberg, the founder, is stepping down from his position as co-CEO after just a year and returning to the role of executive chairman. And the vision of an On Deck accelerator is completely gone, as the company has just launched a new fund to invest in startups at market terms. I learned how a plucked Tiger Global termsheet was one of the first dominoes to fall, according to sources, forcing the company to prioritize growth over runway.
Even if you’re not interested in the intricacies of this one startup, On Deck’s pivot and challenges offer a glimpse into the complexities of building a business. Especially after last week’s Launch House news, I’m fascinated to see two examples of how startups trying to provide a network in exchange for stock and/or money are experiencing growing pains at various points.
In the case of Launch House, the allegations underscored poor leadership. In the case of On Deck, product changes underlined a fragmented focus. Both, though very different stories, have explained how selling something as vague and broad as “community” isn’t that easy. I’ve talked a lot about how a community is more than a Slack group where people exchange ideas; it is living, breathing and requires more than just expression. That’s hard to force on its own, but add in the exponential growth needs of a venture-backed startup and the tradeoffs begin.
It’s hard to get a founder to pay for a network without knowing exactly how that network will benefit the founder. How do you convince founders that your network is much more different than a network they find for free? How do you resolve a buy-in or create a space that is not just transactional? And how do you ask people to wait for the long game payout instead of short term wins?
For the full story, read my feature: “On Deck tried to do it all. Now it tries to do less, better.” If you like this newsletter, will you do me a quick favor? Forward it to a friend, share it on Twitter, and tag me so I can thank you for reading it yourself!
The ideal runway is a myth
When it comes to advice, tech loves standardization. Startups are often told that there are certain metrics to meet, deadlines to meet, and timeframes to measure against. But for todaybusinessupdates.com+ this week, I started digging into the idea that having an ideal startup job is a myth.
Here’s why it’s important: Figures are nuanced. Sure, 20 years of runway could just mean the startup is so close to profitable that it has an unlimited runway and is confident in its future. But it could also mean that the founder isn’t taking as many risks as they should. Some might argue that 20 years of runway is too much runway. I mean, spend a little, right?
The merger did not start
Last week, Equity and Chain Reaction teamed up to talk about The Merge. It’s a perfect episode for people who, like me, didn’t know the intricacies of the event or really didn’t understand its impact or why it sounded like a crypto-specific version of a lunar eclipse.
Here’s why it’s important: Once you’ve listened to the episode, TC’s crypto reporter Jacquelyn Melink has a sequel that’s just different. She reports that Ethereum is down more than 17% after what some describe as a “way too much hyped” Merge.
I’m experimenting with a new section in Startups Weekly where we follow an old story or trend every week to see what has changed since our first look. This week we check in with the latest and greatest insurtech.
Here’s what’s new: Our latest Equity episode takes a closer look at why the industry, somewhat dimmed by its public market compositions, continues to receive millions from venture capitalists. As my work bestie Mary Ann Azevedo reports, the future of insurtech investing is focused on more niche businesses. It’s good to see that specialization, at least in the early days of a startup, helps to stand out.
A few notes
We’re less than a month away from todaybusinessupdates.com Disrupt and I’m already emotional. It will be a blast, a pep talk, a realization and a week not to be missed. Here is the full agenda and here you can buy your tickets.
Now that I’ve got you, will you hang up? As you know, I co-host Equity, which goes out three times a week and is TC’s longest-running podcast. We also have some besties to listen to, including our crypto-focused show going through Chain Reaction and the founder-focused show going through Found. The todaybusinessupdates.com Podcast should not be missing either, so watch all the good shows they put out.
Seen on todaybusinessupdates.com
How Blaseball’s fantasy sports fever dream embraces the future
Brelyon turns heads with immersive virtual monitors
South Korean prosecutors say Do Kwon is ‘clearly on the run’ and ask Interpol for red message
Tech is at the heart of the greatest chess drama in years
Kitty Hawk, the moonshot of the electric plane supported by Larry Page, is shut down
Seen on todaybusinessupdates.com+
8 Investors Discuss What’s Next For Reproductive Health Startups In A Post-Roe World
Smaller Dreamforce still comes out big in first live meeting in three years
In Latin America, founders and investors are balancing prudence and optimism
A quick check of consumer fintech activity ahead of Q3 data
By the way, I passed by Dreamforce in downtown San Francisco this week and it was quite the spectacle. I met iconic climber Alex Honnold, saw Marc Benioff and Bret Taylor speak about the future of ghosts, and was even reminded by Salesforce’s head of communications that it’s a conference about Salesforce, not Twitter (where Taylor is the chairman of the Board of Directors).
Anyway, it was a hoot. Same time, same webpage, next week?