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.

Key Takeaways:

• VAST's adoption was publisher-led, not buy-side: Despite being authored to solve a buy-side problem, the buy-side largely sat out early VAST adoption; ad networks and publishers drove it.
• Google's O&O deficit was actually an advantage: Because Google had almost no owned inventory to monetize, it was structurally forced to invest in off-site programmatic in a way Yahoo, AOL, and Microsoft weren't.
• The custom bidder market was smaller than the hype: Beeswax identified three distinct customer types (media resellers, direct response brands, and mainstream agencies) and found that only the first group was a real fit for the model.
• Acquisition timing matters as much as price: Beeswax sold in early 2021, just before TripleLift's $1.3B exit marked the peak; Ari notes the M&A market for independent ad tech has been weak ever since.
• The SaaS apocalypse is real, with caveats: Ari argues AI and vibe-coding will eliminate a significant portion of SaaS businesses, but concedes that deeply operational infrastructure; pacing algorithms, supply access, click tracking across complex stacks isn't going away via a prompt.

Chapters:

• 00:00:00 Welcome Ari Paparo
• 00:02:03 VAST Origin Story
• 00:07:40 IAB Tech Lab Genesis
• 00:15:08 Google vs. YAML Era
• 00:23:20 Rich Media's Rise & Death
• 00:32:00 Beeswax: The Thesis
• 00:44:23 What Actually Worked
• 00:56:44 Why Beeswax Sold
• 01:09:36 Quibi, CTV & AI Content
• 01:17:32 Marketecture & What's Next

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.

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 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. 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. 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. Ali gets into the discipline of firing the wrong clients, and the moment that finally made the company profitable, and a cold email that landed in the right inbox at the right time. The lesson wasn't the announcement. It was the follow-through.

Key Takeaways:

• Deprogramming is real: Ali compares leaving Google to leaving a cult--the company's culture of exceptionalism actively makes it hard to function anywhere else.
• The co-founder dynamic is the startup: Working alongside your spouse through the hardest years of a young company and having young kids at the same time isn't a fun detail--it's a test most partnerships don't survive.
• Category creation cuts both ways: Defining a new category gives you first-mover advantage, but once competitors flood the messaging, you have to decide whether to defend the label or move past it.
• The right customer matters as much as the revenue: Chalice now vets for scaled data and genuine strategic intent before onboarding; clients who want a better click-through rate get turned away in the pitch.
• Big announcements don't close deals: Their biggest customer came from a cold email.

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

Chapters:

• 00:00:00 Welcome Ali Manning
• 00:01:53 Google From the Inside
• 00:10:02 Leaving Big Tech
• 00:18:34 Co-Founding Chalice
• 00:26:35 Survival & Near Failure
• 00:33:23 Fundraising Realities
• 00:43:28 Building the Product
• 00:50:57 Owning the Category
• 00:54:00 Firing Clients
• 01:00:01 Bets That Paid Off

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's entry into advertising was accidental. 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.

The aQuantive acquisition by Microsoft closed in weeks after Google bought DoubleClick. 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). The same logic drove the Acxiom services spinoff and guides his acquisition playbook.

Key Takeaways

• Data scale over protection: Spinning Atlas out and selling it to competitors produced better insights than keeping it as proprietary agency technology.
• Acquisitions disperse talent and seed cycles: aQuantive and DoubleClick acted as dispersal events, sending people out to found the next generation of companies: The Trade Desk, Aggregate Knowledge, Rover, and others.
• Org structure determines response speed: Walling off a small, fast-moving team was LiveRamp's key move when cookie deprecation hit, something a standard org chart couldn't accommodate.
• Services and technology conflict as they mature: What starts as complementary eventually creates opposing incentives around margins, growth, and investment priorities.
• Preserve acquisitions, don't absorb them: Give acquired teams more resources and a bigger canvas rather than breaking them apart and folding them in.

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

Chapters

• 00:00:00 - Meet Scott Howe
• 00:02:03 - Speed & Engineering Velocity
• 00:05:03 - Breaking Into Ad Tech
• 00:16:35 - Building & Spinning Off Atlas
• 00:30:55 - The aQuantive Deal
• 00:41:53 - Acxiom & LiveRamp Split
• 00:47:32 - Staying Sharp as a Long-Term CEO
• 00:53:31 - Scott's Acquisition Philosophy
• 01:00:01 - Client Obligation & Personal Drive

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.

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.

The conversation covers two modes of building: greenfield at SpringServe, where David explains the opportunistic founding moment when Facebook shut down LiveRail, and unification of teams at Magnite. The dive into a technical breakdown of budget pacing in distributed ad systems: why enforcing a spend cap becomes one of the hardest problems in ad tech (along with the emotional reality of going through an acquisition process that doesn't always close).

Key Takeaways

• "Just stop spending at $100" is not a simple problem. In a distributed ad system, no single machine knows the true spend at any moment. Impression data arrives late, routes through different servers, and the feedback loop lags by minutes or hours. Budget overruns are almost never one bug--they're several compounding. The fix is less about clever algorithms and more about instrumenting the full data pipeline so you know exactly where things break down.
• When a critical system is failing, resist the urge to start over. Everyone's first instinct is to declare it beyond repair and rewrite it. That rewrite will take longer than you think, clients will leave before it ships, and you'll introduce new bugs in place of the old ones. Get it stable first, then have the rewrite conversation.
• A/B tests in ad systems can lie to you. Make your ad server faster, run a split test, and the faster side looks like it's printing money. Roll it out globally and the gain evaporates; budgets are finite and pacing algorithms just redistribute spend. Any test where both sides share a budget constraint isn't truly isolated.
• If teams are still on separate Slacks and VPNs, they're still separate companies. Tooling fragmentation is easy to deprioritize because it doesn't feel urgent. But every time an engineer has to switch VPNs to collaborate, it's a reminder that they don't actually work together yet.
• The number on the term sheet isn't the whole story. If the acquirer doesn't understand why they're buying you, the product gets deprioritized regardless of what the check said. And once you hire a banker and go to market, everyone knows you're for sale--which changes the dynamic in ways that don't always help you.

Chapters

• 00:00:00 - Meet Dave Buonasera
• 00:03:30 - Goldman to Ad Tech
• 00:07:30 - Inside Early AppNexus
• 00:13:00 - Democratizing Data Access
• 00:16:30 - Budget Pacing Explained
• 00:25:00 - Fixing Distributed Systems
• 00:29:00 - Building SpringServe
• 00:44:00 - Real-Time Data as a Feature
• 00:53:00 - Merging Cultures at Magnite
• 01:05:00 - Migration Without Client Disruption
• 01:12:00 - A/B Testing Pitfalls
• 01:16:00 - Navigating Acquisitions

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.

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:

• Lessons from Mike and Ian’s founder journey with Sincera and beyond
• Technical Deep Dives: How the industry’s most influential tools are actually architected
• Unfiltered conversations on the challenges shaping the future of the stack

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

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.

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.

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.