Most AI failures won't come from a bad model. They'll come from bad data.

Shashank Saxena spent most of his career on the buying side of enterprise technology before founding VNDLY which was acquired by Workday for $510 million. He then joined Sierra as a Managing Partner before going full time as Co-founder and CEO of Pantomath, a data operations center for enterprises that are betting their future on AI agents.

We discuss why data quality is becoming one of the biggest challenges in enterprise AI.

An AI agent fed bad data for 12 hours doesn't go rogue. It just makes 12 hours of wrong decisions: rejecting insurance claims, issuing credit cards, or drilling in the wrong location.
As more business decisions are delegated to AI systems, companies will need far greater visibility into what is happening across their data infrastructure.

Shashank also shares the decisions that led to VNDLY's acquisition, the advice he'd give founders evaluating acquisition offers today, and why a Michael Jordan analogy continues to motivate him as a second-time founder.

If you're building enterprise software, selling to large companies, or trying to figure out whether experience is an asset or a liability in the AI era, this episode is for you.

0:00 - Trailer
01:00 - How Shashank became a second-time founder
07:20 - Where Pantomath sits in the data stack
10:55 - How a broken Tableau report turns mission-critical with AI
12:55 - Who Pantomath sells to
15:35 - Solving for a problem that doesn't exist yet
19:03 - How have founder expectations changed today?
20:31 - Series B companies pre- and post-AI
21:26 - The Michael Jordan example
23:57 - How a repeat founder chooses investors
25:10 - What value Snowflake adds as a strategic investor
27:05 - Data is not an open category today
28:34 - The astounding Databricks outcome
29:08 - The reality of the $100 million ARR number
31:48 - Will non-human workers 100x in the next few years?
36:00 - How to protect data in motion
37:26 - How comfortable are we giving full access to agents?
39:47 - Where is automation fastest today?
42:09 - Why entrepreneurs tend to like uncertainty
43:28 - Why Shashank chose to be a founder
45:48 - A customer-driven $510M acquisition
48:32 - Employees vs contractors in any organization
51:22 - Building from Ohio vs the Bay Area
53:14 - Learnings from selling to enterprises
56:31 - How Shashank raised from Tier 1 US VCs
59:19 - Heads down or network as a founder?
1:02:47 - First-time vs second-time founder edge in AI
1:06:22 - Hiring as a repeat founder
1:08:08 - How enterprise sales has changed
1:10:52 - How do you sell for a problem that isn't visible today?
1:12:58 - Best piece of advice
1:16:27 - The only advice for a founder considering M&A
1:21:06 - Position yourself to be capable of taking risks
1:24:51 - What matters to an enterprise buyer?

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This video is for informational purposes only. The views expressed are those of the individuals quoted and do not constitute professional advice.

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