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 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.