The Mark Cuban Podcast

Episode: OpenAI Acquires Sky: The AI Assistant That Works for You

Date: November 1, 2025

Episode Overview

In this episode, the host explores OpenAI’s latest acquisition: Sky, an AI natural language assistant designed for Mac. The episode dives into the rationale behind the purchase, the technology’s capabilities, industry implications, the mysterious background of Sky, and potential conflicts of interest given OpenAI CEO Sam Altman's stake in the company. The host also reflects on the future of AI assistants that can operate at system level, moving beyond browser-based agents.

Key Discussion Points & Insights

1. Acquisition Context & Motivation

• OpenAI’s Stated Vision:
  OpenAI’s blog post emphasized moving AI beyond intelligence, focusing instead on “unlocking it through interfaces that understand context, adapt to your intent, and work seamlessly.” (03:12)
  • The company acquired “Software Applications Inc.” which develops Sky, a natural language interface for Mac computers.
• Sky’s Role:
  Sky is presented as an AI assistant that integrates natively at the Mac OS level, helping users “write, plan, code, or manage your day.” (03:38)
  • Comparisons made to OpenAI’s own Atlas browser-based agent, but with Sky enabling deeper system control.

2. Sky Demo & Feature Set

• Demo Video Analysis:
  • The Sky demo shows users commanding the assistant via screenshots and natural language—e.g., “Add dinner at Mojo at 8 o’clock to my calendar”—with Sky automating the necessary Mac tasks. (05:00)
  • Sky can research options (e.g., bars on Google Maps) and message groups, directly manipulating different Mac apps.
  • The host comments that—much like OpenAI’s Atlas—effective use often feels like “babysitting” the agent. (06:20)
    • Quote:
      “If you’re literally watching it, what’s the point of not just doing the task yourself?” (08:24 - Host)

3. Comparison to Apple Intelligence & Market Context

• Parallels & Differences:

  • Audience feedback wonders if Sky is just filling the gap until Apple launches similar features (“Apple’s been trying to do this for the last three years and is miserably behind. Thanks for filling in the gap until Apple buys your company.” (10:00 - Quoting YouTube comment) )
  • Host concludes:
    “It seems like it’s very similar to what OpenAI is already doing with Atlas, where it takes control of your browser. The difference here… is it actually takes control of your computer.” (11:00)
  • Emphasizes that this means Sky can access local files, photos, calendars—things browser agents can’t.

• Strategic Value:

  • “Microsoft has a really good opportunity to do this with Copilot, because they own the operating system. OpenAI wants a little piece of that. Without their own hardware… they’re at the mercy of whether or not they can get their software in front of people.” (12:30)

4. Founders & Product Status

• Founding Team’s Background:
  • CEO Ari Weinstein and co-founder Conrad previously built Workflow, which Apple acquired. They brought in Kim Beverette, a senior Apple PM for 10+ years, with deep Mac app experience. (14:30)
  • Quote from Ari Weinstein:

    “We’ve always wanted computers to be more powerful, customizable, and intuitive. With LLMs, we can finally put the pieces together. That’s why we built Sky.” (14:40)

• Unusual Aspects:
  • Product isn’t launched yet; little social media footprint.
  • Host says:
    “This isn’t a company that I’ve ever heard anyone talk about before… Not a very big company. Sam Altman is the investor. How did OpenAI hear about them? They don’t have a launched product.” (16:20)

5. Sam Altman Conflict-of-Interest Concerns

• Altman’s Stake:
  • Sam Altman is a direct investor in Sky via an investment fund, as is Figma CEO Dylan Field.
  • OpenAI’s blog discloses Sam Altman has a “passive interest.”
  • Host’s commentary:
    “Essentially by OpenAI buying a company that he personally invested in, he personally makes money… Heavily associated with him. Sam Altman personally invested in it, but whatever.” (18:00)
• Transparency & Skepticism:
  • Host questions if the acquisition is motivated more by advancing OpenAI or by enriching insiders but stops short of making accusations.

6. Industry Impact and Speculation

• On Platform Lock-In:
  • Suggests success could depend on whether Sky expands beyond Mac or stays locked due to Microsoft platform politics.
• Host’s Outlook:
  • “I will be honest and give them their flowers… they brought a really awesome player over from Apple… seems like a really good move. I think they’ll be able to do some interesting things.” (19:30)
  • Concludes it’ll be fascinating “to follow” as the AI assistant race heats up.

Notable Quotes & Memorable Moments

• On Watching AI Agents:
  “If you’re literally watching it, what’s the point of not just doing the task yourself? In my opinion.” — Host (08:24)

• On Product Differentiation:
  “The difference here, and I do think this is valuable, is it actually takes control of your computer.” — Host (11:00)

• Ari Weinstein (CEO, Sky) on Vision:
  “We’ve always wanted computers to be more powerful, customizable and intuitive. With LLMs, we can finally put the pieces together. That’s why we built Sky and AI experience that floats over your desktop to help you think and create.” — Ari Weinstein (14:40)

• On OpenAI’s Disclosure:
  “Disclosure, an investment fund associated with Sam Altman held a passive investment… Associated with him: like, heavily associated with him. Sam Altman personally invested in it, but whatever.” — Host (18:10)

• Nick Turley (VP, ChatGPT, OpenAI):
  “We’re building a future where ChatGPT doesn’t just respond to your prompts, it helps you get done. Sky’s deep integration with the Mac accelerates our vision of bringing AI directly into the tools people use every day.” (19:00)

• On the Team’s Credentials:
  “I will be honest and I’ll give them their flowers… bringing [Kim Beverette] in and having this tie into all of those [core Mac apps] seems like a really good move.” — Host (19:35)

Key Timestamps

• 03:12 — OpenAI’s acquisition announcement & vision
• 05:00 — Sky demo walkthrough and functionality
• 11:00 — Sky’s advantage: direct Mac system control
• 14:30 — Background of founders and leadership
• 16:20 — Discussion of company obscurity and no live product
• 18:00 — Sam Altman’s investment and potential conflict of interest
• 19:00 — OpenAI’s Nick Turley on future of AI assistants

Summary & Takeaways

This episode unpacks the surprise acquisition of Sky by OpenAI, exploring the implications for Mac users and the broader AI assistant market. While the host is skeptical about the overlap with OpenAI’s existing Atlas product and raises pointed questions about insider deals, he acknowledges the impressive pedigree of the Sky team and the potential for deeper AI integration at the OS level—a frontier that could shape user experiences in the years to come. The discussion provides a candid, critical, and informed look at the intersection of tech innovation, business strategy, and startup opportunism.