Rich Habits Podcast – Episode 137:
“This Guy Wants To Give Every American a Free TV”
Air date: September 29, 2025
Brief Overview
In this episode, hosts Austin Hankwitz and Robert Croak interview Ilya Posen, founder and CEO of Telly and co-founder of Pluto TV. The discussion dives into Ilya’s entrepreneurial journey, including the creation and exit of Pluto TV, and his latest disruptive venture—giving away state-of-the-art televisions for free to Americans, monetized through advertising. The episode is a masterclass in thinking differently about business models, tenacity in the face of doubt, and actionable advice for both seasoned and aspiring entrepreneurs.
Key Discussion Points & Insights
1. Ilya Posen’s Backstory & Entrepreneurial DNA
[03:38]
- Born in Russia, immigrated to the US at age 8 with his family, starting with nothing.
- Encountered his first computer at 12 (donated from a synagogue), sparking a passion for technology.
- Founded first company at 17: a web design and marketing agency.
“That computer became my best friend... that's kind of where I became a computer nerd, if you will.” — Ilya [03:38]
2. The Genesis and Disruption of Pluto TV
[05:28]
- Inspiration: Frustration with YouTube’s search-centric approach for kids’ content; realized a need for a “TV Guide” experience for internet content.
- Created Pluto TV: Curated YouTube content into linear, scheduled channels.
- Discovered that mimicking traditional TV habits led to far greater engagement metrics.
- Business model: Ad-supported, unlike the subscription trend dominating at the time.
“We got 36 minute session durations... we were like 10 or 12X-ing YouTube’s numbers with the exact same content. That’s when we knew something was up.” — Ilya [05:28]
- Investor skepticism was huge; received 93 “no’s” before getting first funding. Struggled to license premium content in the early days.
- Market tailwinds: decline in cable, rise of smart TVs, Pluto became the go-to free app when devices (like Roku) were launched.
“We almost went out of business or ran out of money probably three, four times...” — Ilya [12:51]
3. The Pluto TV Exit and Lessons for Future Ventures
[12:06]
- Pluto TV acquired by ViacomCBS for approximately $350 million.
- Today, Pluto TV boasts over $1B in annual revenue.
- The journey included significant near-failures, skeptical studios, and a need for sheer perseverance.
- Lessons from building and selling Pluto are foundational for building Telly.
4. Telly: Reinventing TV For Free
[14:28]
- Telly provides 55-inch QLED HD televisions with premium features (built-in Harman Kardon soundbar, second “smart” screen), entirely for free, monetized via advertising.
- The dual-screen design allows for both entertainment and secondary info (sports scores, stocks, weather) — while the ad component powers the business model.
- Since TVs are now a near-commodity with razor-thin or negative hardware margins, Posen’s model is to disrupt by giving away the device and owning the ad experience.
“We have an opportunity to be the one and all device in someone’s home. The TV is by nature at the center of the family...” — Ilya [26:13]
- Initial funding was raised based on Posen’s track record and a “killer” remote-first team, allowing worldwide recruitment.
- The company went viral at launch, breaking their sign-up server, and received hundreds of thousands on its waitlist—data showed demand came from across all income and education levels.
5. Logistics, Scaling, and User Experience
[24:30]
- Distribution: Direct delivery to users’ homes, no need for retail involvement.
- Deep onboarding: Ensuring ad relevancy via robust customer surveys.
- High demand continues, with $0 spent on marketing to date.
- Telly expects to capture a major segment of the 40 million TVs sold annually in the US: “...way more demand than... supply, I mean, it’s a free thousand-dollar TV, right?” — Ilya [26:13]
6. Building a World-Class, Remote-First Team & Culture
[29:19]
- Emphasis on recruiting A-level talent both at the executive and team level; avoid “B players.”
- Regular cadence with quarterly management offsites and annual company-wide gatherings to bolster remote culture.
- Lean, software-driven principles applied to hardware development: fast iteration and focus.
“We built one unit, we have no intention of building other models... Imagine if you have a team that’s focused on one thing and making that one product really good.” — Ilya [29:44]
7. The Business Model of “Free” and the Future of Advertising
[32:09]
- Posen explains how Americans love free, and are generally comfortable with ads, especially if relevant.
- “Free” business models will keep proliferating wherever categories have become commoditized.
- Commodity categories (where prices and innovation have stagnated) are ripe for disruption via new revenue models (like ads).
- AI is rapidly altering the speed and nature of disruption—incumbents must adapt or risk obsolescence.
8. Hardware + AI: The New Home Platform
[37:03]
- Defends hardware innovation: trillions of dollars have been created with devices (Apple, Google, Microsoft, Tesla).
- Telly’s platform, with microphones, cameras, and processing power, is positioned to become the “iPhone for the home”—central, smart, and ready for AI applications.
- Posen teases upcoming AI capabilities that will take advantage of Telly’s position in the home.
“We’re in front of the whole family in the living room at the center for so many hours a day... I think we have an opportunity to really kind of nail that category.” — Ilya [37:03]
9. Advice for Aspiring Disruptors & Entrepreneurs
[40:05]
- Focus on improving existing categories by 20–25% rather than trying to create entirely new behaviors or categories.
- Leverage familiar designs and habits; reduce friction for mass adoption.
- Tenacity is vital—expect to face skepticism and rejection.
“...Don’t try to get all creative. If we need instructions on how to use this streaming service, we fucked up.” — Ilya [40:05]
Notable Quotes & Memorable Moments
- “I think every business that has started before AI... better hurry up and adopt AI like asap, or they’re going to get lapped by companies that enter their category but are AI at the foundation and enabled.” — Ilya [32:27]
- “The headline of like, hey, this, this crazy man over here is giving away a 55 inch TV completely free… we got a few hundred thousand people to join our waitlist right out the gate. We actually broke our waitlist server.” — Ilya [20:56]
- “We don’t take B players. We just don’t.” — Ilya [29:44]
- “People like ads. I think especially Americans, they’re very accustomed to advertising...” — Ilya [32:27]
- “We’re building the iPhone for the home. We’re a platform.” — Ilya [37:03]
- “...Building something from an entirely new category is very, very difficult.” — Ilya [40:05]
Important Timestamps
- 03:38 – Ilya’s immigrant journey, first business at age 17
- 05:28 – Origin story of Pluto TV and the insight behind linear streaming
- 08:16 – Building and monetizing an ad-supported streaming model
- 12:06 – Pluto TV’s challenges, exit, and lessons learned
- 14:28–15:18 – Telly’s offering and unique business model
- 20:56 – Viral launch of Telly, waitlist explosion
- 26:13 – Telly's rapid growth and market demographics
- 29:44 – Assembling a top remote-first team & creating a winning culture
- 32:27 – The future of free, ads, and AI-driven business disruption
- 37:03 – Hardware, AI, and Telly’s aspiration to be the "iPhone for the home"
- 40:05 – Tactical entrepreneurial advice on product and business model innovation
Episode Takeaways
- Disruptive businesses often start with a familiar but improved experience, not wild novelty.
- Free, ad-supported models thrive in commoditized industries—especially when you can massively undercut traditional cost structures.
- Scalability and virality can be supercharged with remarkable offers—like a free $1,000 TV.
- Leveraging top-tier talent is a force multiplier, especially for remote-first companies.
- The next wave of home technology will be platforms—hardware + software + AI—centered around daily engagement, not just “smart” devices.
- Persistence, conviction, and strategic targeting (not just innovation) are essential for overcoming skepticism and breaking out.
Connect With Ilya Posen & Telly
- Twitter/X: @IlyaNeverSleeps
- Website & Waitlist: telly.com
This episode is a must-listen for anyone interested in technology disruption, advertising innovation, or building companies that change how we interact with essential products in our lives.