May 51 hour 11 mins
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:
- 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
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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.