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E66: What the $100M Shetty Deal Means for Lower-Middle Market M&A + $21M in funding for an AI-led Agency
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E66: What the $100M Shetty Deal Means for Lower-Middle Market M&A + $21M in funding for an AI-led Agency

The Jay Shetty Deal and What It Actually Means

On May 27th, Spotify and Netflix jointly announced an exclusive partnership with Jay Shetty to bring the video version of his podcast On Purpose to both platforms. Variety reported the deal at over $100M across a multi-year term, with three other companies bidding in the nine-figure range. Video episodes go live July 13th. After that date, full-length video episodes leave YouTube. Audio stays non-exclusive — Apple Podcasts, Spotify, everywhere else.

Spotify serves as global ad sales rep for the show.

The surface-level read: big talent deal, streaming wars continue, nine figures for a podcast.

The more important read: this is the third act of a five-year arc, and the deal structure tells you something the press release doesn’t say out loud.

Act One: 2020. Spotify pays approximately $200M for Joe Rogan’s podcast — full exclusivity, audio and video. Distribution as moat. Wall off the audience, own the asset entirely.

Act Two: February 2024. Rogan renews at $250M but the deal is non-exclusive. Apple, Amazon, YouTube all get the show back. Spotify gave up on exclusivity and the strategy that drove it.

Act Three: The Shetty deal. Two competing streamers split video rights. Neither insisted on exclusivity. Audio went non-exclusive. Ad sales went to Spotify. The structure reflects a shared understanding that walling off audiences destroys the asset.

The translation at $100M: even at nine figures, the buyers know the audience has to be able to find the creator wherever they listen. The distribution moat strategy failed. What replaced it is a different bet — not on owning the distribution, but on owning the relationship with the creator and the revenue that flows from it.

Why this matters for the lower middle market:

The platforms just admitted they cannot build creators like Shetty from scratch. They have to buy them. Jay Shetty had over a billion listens. He was ranked 24 on Spotify’s most-listened list in 2025. He ran on the iHeart Podcast Network for three years before iHeart couldn’t agree on a renewal and got outbid by streamers who aren’t even core podcast distribution businesses.

When the buyers have to pay nine figures for talent and they can’t manufacture that talent internally — the next question is where the talent pipeline comes from. And the answer is podcast production agencies.

The structure of the market looks like this: at the top, nine-figure checks for established creators. Down market, dozens of five to thirty-five person shops doing production, booking, ad sales, and content strategy in specific verticals. Those agencies are the ones creating the next Shettys. They’re the farm league.


The Roll-Up Precedent Is Already There

This isn’t a theoretical future. The deals have already started:

Last year, Insignia paid $100M+ for Veritone One and Oxford Road — both podcasting advertising agencies. Fox acquired Red Seat Ventures. ACast acquired Wonder Media. TCG put $40M into Audiochuck. A mobile marketing agency acquired Kitcaster, a podcast booking and PR shop. OpenAI paid approximately $100M for TPBN — making the Shetty deal and the TPBN deal the two biggest audio deals of the year so far, and OpenAI is not a normal media buyer by any stretch.

The signal that matters most to us: Gayle Troberman, former CMO of iHeartMedia and now and advisor, has started a side venture called Bubbler — a B2B podcast network. When someone with that experience at iHeart says “I see a shift coming and I’m starting something,” it sends a signal that there is a lot of gas in the tank for the future of podcasting.


The Valuation Gap That Creates the Opportunity

Here’s the part that’s interesting from an M&A perspective: podcast production agencies are still being priced like services businesses. Not like talent factories.

A services business is valued on a multiple of EBITDA. A talent factory — an agency that has 100 clients and five to ten of them have the potential to become the next major creator — is something different. But there’s no shared yardstick for IP and franchise value before it’s commercialized. No standard methodology for pricing what a creator relationship is worth before it monetizes at scale.

Ayelet flagged a startup she’s been watching called Mark — building exactly this. The FICO score for franchise value. A rating layer for creator IP. The thesis: capital is already being deployed into podcast agencies, but it’s being deployed blind because there’s no shared pricing mechanism for what’s actually being bought. Mark is building that mechanism.

The data problem is real on the analytics side too. YouTube gives meaningful listener data — streams, retention, audience demographics. Apple and Spotify give bare bones data. Even the smaller, scrappier podcast agencies have built their own internal analytics infrastructure to compensate — which means there’s a tech layer underneath a lot of these businesses that makes them more interesting to buyers than the pure services revenue would suggest.

If you’re a buyer looking at podcast agencies right now and only looking at the P&L, you’re pricing the wrong part of the asset.


Quick Hit 1: Coupa Acquires Tonkean

On May 21st, Coupa — the Thoma Bravo-backed spend management platform — acquired Tonkean, an Israeli-born agentic intake and orchestration platform co-founded by Sagi Eliyahu and Ofir Talmor.

The stated rationale: Tonkean completes Coupa’s vision of an end-to-end agentic procurement workflow by adding intelligent request intake on the front end. Terms not disclosed.

This is Coupa’s third acquisition in roughly 12 months — Rossum was two weeks ago. The pattern is clear: Thoma Bravo is systematically building the complete source-to-pay stack one capability at a time.

The Israel note: approximately 80 people, another Israeli startup tucked into a major enterprise platform. Israel continues to produce enterprise AI companies at a rate that’s genuinely remarkable for a country that just turned 80 years old. Christian flagged what Ayelet confirmed: Israeli startups are exceptionally strong on the technology side and have historically plateaued around $5M ARR — which used to make them modestly priced tuck-in targets. Those prices are meaningfully higher now. The talent and technology command real multiples.


Quick Hit 2: Solstice Raises $21M Series A

On May 27th, Solstice — a New York-based AI-native marketing agency for pharma brands co-founded by R. Sekka and Yiwin Lee — announced a $21M Series A led by Transformation Capital, with 12 Below and Virtue Ventures participating.

The pitch: pharma marketing content typically takes months to build because of regulatory requirements. Solstice’s AI-powered workflow compresses that to 10 days or less — while maintaining compliance.

Why this matters beyond the funding announcement: Solstice is the venture-stage version of the thesis we’ve been tracking since our Silicon Valley targeting agencies episode. Software-shaped, vertically specific, AI-native from day one, raising institutional capital at the $20-25M threshold that signals serious future acquisition interest.

Companies clearing that institutional bar right now — in pharma marketing, in paid social, in whatever vertical is next — are the acquisition targets of the next three to five years. The corp dev teams at scaled independents should be tracking them now, before the capital accumulates and the price goes up.


Quick Hit 3: InstaAgent an Alchemist & YC P26 Backed Startup

InstaAgent just came out of the latest Alchemist Accelerator class (Christian is an advisor) and the Y Combinator P26 batch. They’re currently in the funding process.

The product: a collaborative workspace for marketers and AI agents. Starting with paid social for mid-market e-commerce brands — strategy, content, distribution, analytics — built around coordination infrastructure so agent swarms can plug in and execute reliably with humans in the loop.

The category: automated media buying at early stage. The kind of company that gets much more expensive to acquire if you wait 18 months.


What’s Coming

Episode 67 drops this weekend: Justin Hayashi, CEO and co-founder of NewEngen, who made the Grapevine AI acquisition that’s been working out exactly as advertised.

Next week: Christian and Ayelet take In/Organic to the main stage at M&A Source — a conference for M&A advisors with a deal market for PE groups. They’ll be on a panel on deal flow. Come find them.


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