Maestro has spent nearly a decade pulling the media industry toward a more interactive, personalized future - often years before the market was ready.
In this episode of Future of Fandom, we sit down with Ari Evans, Founder & CEO of Maestro, to unpack his journey from product management to entrepreneurship, and how early lessons from gaming now shape the next generation of sports and media experiences.
Ari shares how freemium economics at Zynga reshaped his thinking around funnels, personalization, and conversion - and why those same principles are finally finding their way into broadcast and streaming. We explore the shift from one-to-many TV to one-to-one digital experiences, the complexity of building across connected TV platforms, and why "just streaming" is no longer enough.
The conversation dives deep into personalized interactive video, cross-platform SDKs, and how AI is accelerating experimentation inside large organizations - from automating graphics and overlays to removing internal coordination bottlenecks. Ari also explains why educating casual fans is the biggest untapped opportunity in sports, how influencer co-streams can drive top-of-funnel growth, and why product-market fit matters more than ever in an AI-first world.
If you care about fan engagement, personalization, and what's next for sports media, this one's for you.
What you'll learn in this episode
>> How Maestro evolved from early interactive livestreams to cross-platform SDKs powering connected TV experiences.
>> Why personalization - not multiview - is the real unlock for increasing watch time and fan loyalty.
>> How gaming principles like funnels and experimentation apply directly to sports and media.
>> The opportunity to turn casual viewers into superfans through education and just-in-time experiences.
>> How AI is removing friction inside enterprises and enabling faster product iteration.
Timestamps
00:00 – Intro & teaser: AI disruption and the gap between small and large organisations
00:26 – Welcome & episode introduction
01:18 – Ari's background: Goldman Sachs, Stanford, and joining Zynga
03:30 – The Zynga lesson: freemium models, whales, and monetising casual fans
07:00 – Building interactive live streams before the market was ready
10:30 – The shift from esports to music to DTC: pivoting to find product-market fit
13:00 – Why streaming only unlocked its real potential in the last two years
15:30 – The case for personalisation: from data collection to actual implementation
19:25 – Cross-platform challenges: TV, mobile, remote vs. phone as primary screen
22:00 – Building for low-power devices and the least common denominator problem
24:30 – The no-code rule builder: automating personalised overlays at scale
26:30 – Early results: personalised graphics and higher click-through rates
28:30 – Multiview: is it data-driven or just table stakes?
31:00 – Where multiview does work: March Madness, Olympics Gold Zone
33:00 – The casual fan opportunity: what's the first-time viewing experience?
35:00 – AI dictating the next video: personalised broadcast at scale
37:00 – The co-streams product: growing top-of-funnel through influencers
38:30 – Building solo with AI: Ari's experience vibe coding the new product
40:00 – Why product-market fit matters more than ever in an AI-accelerated world
41:50 – Liberal arts vs. engineering: why how you think beats how you code
43:00 – Wrap up & outro
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About
Miheer Walav
