Podcast Summary: This Week in Startups

Episode: Savvy is HQ Trivia + Wordle (feat. Scott Rogowsky) | E2245

Date: February 4, 2026
Host: Jason Calacanis
Guest: Scott Rogowsky (HQ Trivia, Savvy Co-founder)

Overview

In this engaging episode, Jason Calacanis sits down with Scott Rogowsky—best known as the face of HQ Trivia—to discuss his latest venture, Savvy, a live, interactive word game app described as “HQ Trivia meets Wordle.” The conversation dives deep into Scott's career trajectory from standup comic and talk show host to chief quizmaster, the meteoric rise and fall of HQ Trivia, lessons learned about media startups, and why Savvy’s game format and team have him optimistic about striking gold again. The episode is a candid, sometimes tongue-in-cheek exploration of startup resilience, audience building, and the tough realities of marrying entertainment and tech.

Key Discussion Points & Insights

The Birth of Savvy: A Live, Competitive Word Game

• Savvy's Format and Innovation

  • Savvy is a live, interactive mobile game, running Sunday to Thursday at 9pm Eastern/6pm Pacific, where Scott plays word puzzles in real time against the audience—essentially, it's “Wordle Live."
  • “Me versus you. If you score more points than me, if you get the word before I do, you win.” (Scott, 00:09)
  • The show rewards players with small sums of money that accumulate in a virtual piggy bank, which can be “broken” for a cash out (explained in detail at 22:28).
  • Savvy is available for iOS and Android and is rapidly picking up downloads.

• Team and Startup DNA

  • Unlike HQ’s original founders, the Savvy team combines Scott’s media/host background with co-founders experienced in mobile gaming—a conspicuously missing ingredient in HQ’s original crew (21:02).

HQ Trivia: Meteoric Rise, Cautionary Fall

• Scott's Journey to HQ Trivia (03:17–06:42)

  • Scott recounts hustling as a standup comic and running “Running Late with Scott Rogowsky,” until a “game show on the phone” audition with the Vine guys landed him HQ Trivia.
  • “I went in for the audition. I always take the meeting, always take the audition. And I got this gig... It went from 50 people in that first show to a million people in a matter of months on New Year's Eve.” (Scott, 03:25–04:30)

• HQ’s Unprecedented Success:

  • HQ Trivia was the first highly-produced, live, interactive mobile game show, boasting “appointment viewing” with real cash prizes and a charismatic host.
  • “It was like a perfect recipe… for success.” (Scott, 04:34)

• Founders’ Inexperience and Structural Issues (08:22–11:15)

  • The company’s leadership lacked entertainment and mobile gaming experience, which Scott sees as a fatal flaw. Money flooded in from VCs, but decision-making froze.
  • HQ Trivia peaked at 2.5M concurrent users in April 2018; by January 2019, it had fallen to 350,000.
  • “They didn’t have the right pieces to build a sticky, engaging product.” (Scott, 11:15)

• Ownership & Compensation

  • Scott started as a “hired gun,” receiving $100 per show and six-week contracts, later offered 0.25% equity.
  • “You were the face of the brand... and they never offered you to be a co-founder?” (Jason, 10:51)
  • “No, no, no.” (Scott, 10:24)

• Why HQ Failed:

  • Product stagnation: “It was the same meal every day” (Scott, 12:25)—users needed novelty and new engagement mechanics.
  • Leadership paralysis: Talent and product teams proposed innovations, but “nothing got shipped… totally paralyzed.” (Scott, 16:00)
  • Tragedy: The co-founder’s overdose further destabilized the company.

Building Again: Learning from HQ, Launching Savvy

• Startup Lessons in Resilience (00:37; 19:41–21:02)

  • Jason repeatedly lauds Scott’s relentless positivity and grind in the face of abrupt highs and lows. His advice: “If you show up every day and it’s high quality and you’re consistent, it’ll work out because you have time to iterate on it.” (Jason, 19:41)

• Savvy's Distinct Approach

  • The host competes against users, a mechanism absent from existing platforms (18:14–18:17).
  • Rewards are doled out regularly, and the viral “bank and hammer” feature provides daily engagement (22:28).

• Future Monetization:

  • Intends to implement subscriptions for additional features and enhanced rewards, learning from HQ’s lack of a sustained revenue model.
  • “Subscription… keeps it pure. If people love the game, they subscribe. If they fall out of the love with the product, they unsubscribe.” (Jason, 23:45)

Notable Quotes & Memorable Moments

• On Taking Initiative:
  • “If no one’s going to give me the job, I’m going to make it myself.” (Scott, 06:42)
• On Being the Face but Not the Boss:
  • “I was a hired gun, Jason.” (Scott, 03:01)
• On Bad Founder-Investor Fit:
  • “VCs just dumping piles of cash at the feet of people who are frankly, totally unqualified to run businesses…” (Scott, 08:22)
• On What Makes Community Platforms Work:
  • “Building a community business is really hard. And if you’re a first time founder or independent creator, you may not be prepared for everything you need to accomplish.” (Jason, 13:14)
• On Resilience:
  • “You’re like the perfect personification of this, which is— it’s really hard when you hit lightning in a bottle early in your career… But you take all those lessons and you keep going at it.” (Jason, 19:41)

Timestamps for Important Segments

• 00:00–00:21: Introduction to Savvy’s live game format.
• 03:17–06:42: Scott’s comedic background and road to HQ Trivia.
• 08:22–11:15: Inside HQ’s structure: leadership missteps and compensation.
• 11:15–13:14: HQ Trivia’s decline, product stagnation, and why it lost the audience.
• 14:35–15:17: Comparing HQ with Jeopardy and Wordle’s different dynamics.
• 16:00–17:08: HQ’s final days; loss of traction, leadership inertia, and Scott’s exit.
• 17:24–18:14: Savvy’s founding: a new model for live mobile games.
• 19:41–21:02: Lessons on resilience, consistency, and audience growth.
• 22:28–23:13: Savvy’s prize structure and future plans for monetization.

Closing Thoughts

This episode offers a candid look at startup highs and lows through the lens of Scott Rogowsky’s journey—highlighting the importance of the right team, iterative innovation, and relentless pursuit of audience engagement. For anyone interested in the intersection of tech, entertainment, and startup execution, this conversation is a fast-paced, wisdom-packed ride.

How to Join Savvy:

• Download from the App Store or Google Play (search "Savvy Words Puzzles Live" or visit playsavvylive.com).
• “If you want to work for Savvy, if you want to play Savvy, hit us up. I’m available on all the socials.” (Scott, 21:02)

End of main content. Ads, outro, and subsequent interview on satellite startups (Starfish Space) omitted.