Mike O'Sullivan and Ian Myers with sit down ad tech founders and builders for conversations about how their products actually got made. This episode collects the WFIO moments (short for "we're f*****, it's over) from across those conversations, covering a year of failed hiring and a homemade DSP, a budget system that quietly overspent in production, and a bootstrapped startup that went unpaid through a pandemic and a stalled Series A.

Listen to our full episodes on the feed.

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The Build with Mike O'Sullivan is a podcast produced by The Current which is owned and operated by The Trade Desk, Inc. Learn more: https://www.thecurrent.com/

Sincera was acquired by The Trade Desk, Inc.

Brian Stempeck is the CEO and co-founder of Evertune AI, a platform that helps brands and agencies understand and influence how AI models represent them in consumer search. In this episode (00:00:00), he traces the path from employee #8 at The Trade Desk to founder, and breaks down why AI search is a fundamentally different marketing channel...not just the next version of SEO.

Before Brian Stempeck started a company, he spent over a decade learning what it looks like when a startup gets commercial strategy right from the beginning. He came into the ad tech world as a generalist--no sales background, no industry experience--and that turned out to be the point. The conversation with Mike and Ian covers what he absorbed about selling complex technology to buyers who don't fully understand it (00:09:50), why user empathy compounds into product loyalty (00:15:54), and how transparency became a more durable competitive weapon than features. That foundation shows up directly in how he thinks about building Evertune.

The transition out of a decade-long hyper-growth run isn't just a career move, it's an identity reset, and Brian gets candid about how long that actually takes (00:26:57). The founding thesis for Evertune came from watching consumer behavior shift in real time: people were routing commercial queries through ChatGPT and Gemini instead of Google, and brands had no visibility into what those models were saying about them or why (00:32:26). That gap between where consumer attention was going and where brand investment was still pointed was the opening.

Evertune raised a $4M seed in fall 2024, went to market in early 2025, and closed a $15M Series A seven months later (00:43:08). The product helps brands measure how AI models represent them across millions of probabilistic queries, then identifies the content, PR, and paid media levers that can move the needle. Stempeck draws a sharp distinction between this and SEO: AI search is mid-funnel, conversational, deeply personalized, and the underlying models change without notice (00:53:52). ChatGPT cut the number of brands it recommended in a given category by a third in a single update with no announcement, no changelog. That volatility is exactly why the problem requires a dedicated platform, and why Stempeck sees the current moment as the closest parallel to the early days of programmatic: fast-moving, infrastructure-level, and undersold to the buyers who need it most.

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The Build with Mike O'Sullivan is a podcast produced by The Current which is owned and operated by The Trade Desk, Inc. Learn more: https://www.thecurrent.com/

Sincera was acquired by The Trade Desk, Inc.

Ari Paparo co-wrote the VAST spec (00:02:00), spearheaded the creation of the IAB Tech Lab (00:07:40), and later co-founded Beeswax, a bidder-as-a-service company acquired by Comcast in 2021. This episode covers the origin of video ad standards, the rise and fall of the custom bidder market, the lessons Ari draws from Beeswax's trajectory, and what he's doing now at Marketecture.

Long before anyone was debating CTV take rates or header bidding strategy, Ari Paparo was sitting at DoubleClick writing XML specs in Microsoft Word and accidentally building the infrastructure that video advertising still runs on today. This episode starts at the beginning: how VAST came to exist, why version 1.0 flopped, how 2.0 caught fire, and why version 4.0 has essentially zero adoption. Ari also walks through his frustration with the IAB's technical rigor (00:15:08) at the time and a conversation with Randall Rothenberg that eventually led to the creation of the IAB Tech Lab.

Ari takes Mike and Ian through the mid-2000s consolidation wars, the rise and quiet death of rich media (00:23:20), and Beeswax (00:32:00)--where Ari is unusually candid about which parts of the thesis held (00:44:23), which didn't, and where he thinks he stayed too long on a strategy that wasn't working (00:56:44). The episode closes on AI generated dramas (01:09:36), Marketecture (01:17:32) and the SaaS apocalypse.

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The Build with Mike O'Sullivan is a podcast produced by The Current which is owned and operated by The Trade Desk, Inc. Learn more: https://www.thecurrent.com/

Sincera was acquired by The Trade Desk, Inc.

Most ad tech companies optimize for the platform. Ali Manning built Chalice to do the opposite, and did it mid-pandemic, alongside her husband. Their savings was draining and the company almost didn't make it. Mike and Ian uncover why it did.

Ali Manning didn't set out to start a company. When COVID hit and her job imploded, she got pulled into Chalice gradually: drafting models, workshopping pitches, listing herself as COO before she'd fully committed. What finally pushed her over the edge (18:34) was watching her husband testify before the Senate against Google in an antitrust hearing and realizing she belonged on that side of the table.

The early years ran on COBRA, a shared nanny, and milestone deadlines that kept moving (26:35). When Peloton pulled back post-pandemic, Chalice nearly ran out of money. The Series A collapsed when their lead investor's committee banned investing in ad tech (33:23). What came next changed everything.

Chalice built a name in custom bid algorithms, then had to defend the category as competitors moved in and eventually decided to move past the label entirely (50:57). Ali gets into the discipline of firing the wrong clients (54:00), and the moment that finally made the company profitable — a cold email that landed in the right inbox at the right time (1:00:01). The lesson wasn't the announcement. It was the follow-through.

Key Takeaways:

Further reading: Ali Manning is now a contributor to The Current, read on.

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The Build with Mike O'Sullivan is a podcast produced by The Current which is owned and operated by The Trade Desk, Inc. Learn more: https://www.thecurrent.com/

Sincera was acquired by The Trade Desk, Inc.

Scott Howe, CEO of LiveRamp, traces his career from BCG and Avenue A/Razorfish through the aQuantive acquisition by Microsoft and into his current role leading LiveRamp.

Scott Howe's entry into advertising was accidental (00:05:03). A BCG yield management project for Qantas convinced him data would be the defining competitive advantage of the internet era. That conviction led him to Avenue A/Razorfish, where the team built Atlas, a buy-side ad server rivaling DoubleClick, then spun it off and sold it to competitors to maximize data scale (00:16:35).

The aQuantive acquisition by Microsoft closed in weeks after Google bought DoubleClick (00:30:55). Scott counts delivering the news to his team as one of his career highlights. Microsoft's display position was stronger than most remember (it included Facebook's ad inventory), but a strategic pivot to search led to a talent exodus that seeded much of modern ad tech, including Jeff Green founding The Trade Desk.

At LiveRamp, Scott has applied the same principles consistently: when cookie deprecation hit, he stood up a skunkworks team outside the normal org (led by co-host Ian Myers) (00:41:53). The same logic drove the Acxiom services spinoff and guides his acquisition playbook (00:53:31).

Key Takeaways

Further reading on The Current: CTV Measurement and the Open Web

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The Build with Mike O'Sullivan is a podcast produced by The Current which is owned and operated by The Trade Desk, Inc. Learn more: https://www.thecurrent.com/

Sincera was acquired by The Trade Desk, Inc.

Mike and Ian sit down with David Buonasera, CTO of Magnite (00:00:00), to unpack what it really takes to build and scale complex systems in ad tech.

Before becoming the CTO of Magnite, David co-founded SpringServe--a bootstrapped, video-native ad server that grew from an internal tool into an acquisition target. He started his career in finance before joining AppNexus as one of its first 18 employees (00:07:30).

The conversation covers two modes of building (00:13:00): greenfield at SpringServe, where David explains the opportunistic founding moment when Facebook shut down LiveRail (00:29:00), and the unification of teams at Magnite (00:53:00).

They dive into a technical breakdown of budget pacing in distributed ad systems (00:16:30), why enforcing a spend cap becomes one of the hardest problems in ad tech (00:25:00), and the emotional reality of going through an acquisition process that doesn't always close.

Also covered: real-time data as a product differentiator (00:44:00), migrating infrastructure without disrupting clients (01:05:00), and the A/B testing pitfalls that trip up even experienced engineering teams (01:12:00).

Key Takeaways

Chapters

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The Build with Mike O'Sullivan is a podcast produced by The Current which is owned and operated by The Trade Desk, Inc. Learn more: https://www.thecurrent.com/

Sincera was acquired by The Trade Desk, Inc.

Ad tech moves fast, but the real stories happen behind the scenes. This is where the architects of the industry come to talk shop.

Hosted by Mike O’Sullivan and co-host Ian Meyers - who first teamed up as the founders of Sincera - this is a builder-to-builder podcast for the founders, engineers, and innovators scaling the next generation of ad tech infrastructure. Drawing on their shared history of building in the trenches, Mike and Ian move past the headlines to explore technical hurdles, strategic pivots, and the candid realities of a complex ecosystem.

What you can expect from this series:

New episodes on Tuesdays. Follow The Build with Mike O’Sullivan on Spotify, Overcast, or wherever you get your podcasts.

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The Build with Mike O'Sullivan is a podcast produced by The Current which is owned and operated by The Trade Desk, Inc. Learn more: https://www.thecurrent.com/

Sincera was acquired by The Trade Desk, Inc.

Mike O’Sullivan (Co-Founder of Sincera and GM of Product at The Trade Desk) sits down with Michael Rubenstein, Co-Founder and Co-CEO of Firsthand, for a candid founder-to-founder conversation about innovation, risk, and leadership in the age of AI.

From DoubleClick to AppNexus (00:38) to Firsthand, Michael shares lessons from decades at the forefront of ad tech: what it means to build with purpose (04:50), how to hire and scale teams that thrive (14:15), and why the next wave of growth will come from brands who embrace AI directly (17:50).

This live episode was recorded at Advertising Week New York in October 2025.

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The Build with Mike O'Sullivan is a podcast produced by The Current which is owned and operated by The Trade Desk, Inc. Learn more: https://www.thecurrent.com/

Sincera was acquired by The Trade Desk, Inc.