Neumann’s next bold move & why Atlassian’s Stride failed

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OpenAI is giving other developers access to its speech-to-speech engine that powers ChatGPT's advanced voice mode. The move paves the way for a wave of AI apps that offer conversational voice interfaces.

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Why Atlassian’s Slack competitor failed

Atlassian shutting down Stride, their Slack competitor, offered some big lessons. Let’s break down the mistakes they made and what they could’ve done differently.

Pricing missed the mark: Stride charged $2 a month per customer, while Slack had a freemium model—free with the option to upgrade to $10 a month. And here’s the thing: free beats cheap every time. Slack’s freemium model not only attracted users faster, but over time, Slack ended up making more money per customer through upgrades. In hindsight, Atlassian’s Stride should’ve embraced freemium early on to stay competitive.

Scaling the team didn’t scale productivity: When Atlassian first acquired Stride, the team was around 10-12 people and operated with incredible speed. But when they doubled the team, things didn’t move any faster. Why? As the team grew, more time went into documentation, code separation, and managing new processes. To make real progress, Atlassian would’ve needed to triple or even quadruple the team, not just double it.

Growth was good, but not enough: Stride was growing at an impressive 300-400% year over year, which sounds amazing—until you realize that in a market as massive as theirs, they probably needed to be growing at 1,000% or more. Atlassian underestimated just how much investment was required to keep up with the potential growth in the space.

The bottom line? Stride fell behind because of a pricing misstep, scaling challenges, and underestimating market growth. It’s a cautionary tale for any startup looking to compete in a crowded, fast-moving market.

Startup funding sees 8% rise in Q3, AI drives growth

U.S. startups raised $37.5 billion in the third quarter, marking an 8% increase year-over-year, driven by large deals and AI investments, according to PitchBook and the National Venture Capital Association. While growth slowed compared to the 59% surge seen in Q2, major rounds from companies like defense firm Anduril, AI research lab Safe Superintelligence, and AI chip maker Groq played a significant role in keeping momentum.

However, deal volume dipped 17% to 2,794 compared to the same time last year, though PitchBook anticipates the final count will rise once additional deals are tallied. Notably, OpenAI’s recent $6.6 billion round will further boost the fourth-quarter figures.

Adam Neumann’s return to coworking with Workflow

Adam Neumann isn’t done shaking up shared workspaces. After being cut from WeWork’s attempt to buy back the company, Neumann is launching a new coworking venture—Workflow—under his residential real estate startup, Flow.

The shift: Unlike WeWork, which was criticized for signing long-term leases while catering to short-term tenants, Workflow will rent office spaces in residential buildings Flow already owns. This change in strategy could help Workflow avoid WeWork's financial pitfalls, where massive lease commitments outweighed short-term revenue.

Why it matters: Neumann's first swing at coworking left WeWork in shambles, but now he’s banking on his lesson learned. With backing from Andreessen Horowitz, he’s claiming a more measured approach, focusing on discipline and avoiding risky assumptions.

Flow currently operates in cities like Miami, Fort Lauderdale, and Atlanta, with expansion plans into Saudi Arabia. Unlike WeWork’s sprawling locations, Workflow will focus on leasing smaller spaces inside Flow’s own properties or in partnership with landlords.

The takeaway: With a retooled business model and a sharper focus, Neumann's Workflow may sidestep the challenges that plagued WeWork. But given his track record, the industry is watching closely to see if he can truly make coworking work the second time around.

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Productivity: ChatGPT’s ‘canvas’ interface makes it easier to write and code.