Building Real-Time Data Streaming for AI | Jacqueline Cheong, Co-founder and CEO of Artie

Jan 28, 2026

Jacqueline Cheong, co-founder and CEO of Artie, builds real-time data streaming infrastructure for analytics and AI. She discusses why moving data is surprisingly hard and how real-time feeds power AI and agents. Jacqueline also covers how Artie wins enterprise customers, automates prospecting with AI, and the tradeoffs of building versus buying streaming systems.

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ADVICE

Choose Focused Sources To Build Reliability

Focus narrowly on the few highest-value sources first to build deep reliability for real-time pipelines.
Say no to tempting integration requests until core quality is ironclad.

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ANECDOTE

First Big Customer Landed With No UI

Artie's first customer onboarding (Substack) streamed billions of rows despite minimal prior testing.
They had no UI and used shared Google Sheets and manual status updates during backfill.

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ADVICE

Automate After You Manually Prove It

Do manual, hands-on work for initial customers, then codify it into runbooks and automate.
Iterate from manual to runbook to automation for faster, repeatable onboarding.

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What Artie Does: Real-time Data Streaming

04:01 • 1min

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Why Moving Data Is Hard in Practice

05:13 • 2min

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Scale: From Rows to Billions of Changes

06:51 • 3min

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Evolution of Data Warehouses and Latency Needs

10:18 • 2min

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Why Real-Time Matters for AI and Agents

12:41 • 2min

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Why Real-Time Streaming Is Rare and Risky

14:31 • 3min

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Why Companies Build In-House and Then Switch

17:11 • 4min

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Trust Concerns: Outsourcing Mission-Critical Data

20:49 • 2min

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Market Position: Cake vs Ingredients

23:08 • 3min

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Early Product Focus: Databases First

26:35 • 4min

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Acquiring First Customers with Cold Outbound

30:28 • 2min

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Onboarding Substack: Scaling a Tiny POC

32:30 • 4min

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Handling Compliance: BYOC and Onsite Implementation

36:24 • 3min

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Manual Work Then Automation Across Ops

39:01 • 35sec

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BizOps Reporting to Engineering as a Hack

39:36 • 4min

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Automating GTM: Replacing BDRs with Systems

43:54 • 3min

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Customer Experience: Direct Slack Support

46:37 • 3min

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Over-supporting Customers as a Strategic Advantage

49:25 • 4min

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Origins: Robin's Experience at Zendesk and Opendoor

52:59 • 3min

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Deciding to Start Artie and Quitting Jobs

55:30 • 4min

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Applying to YC and Learning to Sell

59:25 • 4min

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Sales Playbook: Discovery Calls and Technical Buyers

01:03:14 • 3min

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Improving Discovery: Provide Unexpected Insights

01:06:30 • 4min

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Announcing Series A and Growth Plans

01:10:08 • 2min

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Working with Standard Capital's Batch Model

01:12:03 • 6min

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Value from Investors Without Board Seats

01:17:50 • 5min

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Leadership Lessons: The Score Takes Care of Itself

• Mentioned in 51 episodes

The Score Takes Care of Itself

My Philosophy of Leadership

Bill Walsh

This book provides insights into Bill Walsh's philosophy of leadership, gleaned from his successful career as the head coach and general manager of the San Francisco 49ers. Walsh stresses the importance of creating a strong culture, setting high standards, and thorough preparation. He advocates for leaders to focus on the process rather than the outcome, emphasizing that 'the score takes care of itself' when the right principles are applied. The book also touches on Walsh's personal struggles and the toll of relentless pressure, highlighting the importance of maintaining a balance between work and personal life. It offers practical advice on leadership, applicable not only in sports but also in business and other fields.

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The State of the States

Meredith Whitney

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• Mentioned in 10 episodes

Founding Sales

Peter Kazanjy

Jacqueline Cheong is the Co-founder and CEO of Artie.

Artie moves data across your systems in real-time, and we talk about why that’s so important in the age of AI.

It’s a lot harder than you’d think, as less than 5% of real-time data streaming projects are successful.

I talked to a dozen people to prepare for this conversation, including Jared Friedman who worked with Jacqueline during YC, her sales coach Ras, and numerous Artie employees like A-nee-rud, Ryan, Sarah, Shangbing and Jacqueline’s co-founder Robin.

We talk through how Robin built real-time data streaming at OpenDoor and Zendesk before they started Artie, and Jacqueline shares the sales playbook she learned going from hedge fund analyst to software CEO, including asking customers for their hardest problem and then solving it with the product.

Artie just announced a $12 million Series A a few weeks before we published this episode. We talk about how they landed all of their early enterprise customers through cold outbound, how they structure and automate their prospecting with AI so they have no BDRs, and why they’re seeing customers switch to Artie even after building their own multi-million dollar real-time streaming projects in-house.

I also asked Jacqueline what it’s like working with Standard Capital. They’re a new fund started by a group of YC partners, and it was fascinating to hear about the things they’ve borrowed from YC when investing at the Series A stage.

Try Numeral, the end-to-end platform for sales tax and compliance: ⁠https://www.numeral.com⁠

Sign-up for Flex Elite with code TURNER, get $1,000: https://form.typeform.com/to/Rx9rTjFz

Timestamps:

(4:08) Artie: Real-time data streaming

(5:13) Why moving data is so hard

(9:14) Evolution of data warehouses

(12:47) AI needs real-time data

(18:44) Build vs buy in data streaming

(22:51) How to build in a crowded market

(26:26) Early focus on a specific hard problem

(30:33) Acquiring enterprise customers from cold emails

(32:51) Onboarding their first customer with no UI

(35:46) Solving compliance and implementation

(38:50) How to automate internal engineering, marketing, and ops

(44:01) Building an AI-powered GTM pipeline and motion

(46:52) Add your customers on iMessage, Slack, Teams

(53:00) Starting Artie to solve their own problem

(59:25) Discovering YC through a friend

(1:02:20) Everything Jacqueline learned about sales

(1:06:29) How to improve your sales discovery calls

(1:10:08) Inside Artie’s $12m Series A

(1:16:44) What its like working with Standard Capital

(1:22:59) Jacqueline’s favorite book

Referenced

Try Artie: https://artie.com

Careers at Artie: https://www.artie.com/careers

Clay: https://www.clay.com

Podcast with Tommy @ Alloy: https://www.youtube.com/watch?v=e7i8Wxklu-Y

YCombinator: https://www.ycombinator.com

Standard Capital: https://www.standardcap.com

Founding Sales: https://www.foundingsales.com

The Score Takes Care of Itself: https://www.amazon.com/Score-Takes-Care-Itself-Philosophy/dp/1591843472

Follow Jacqueline

Twitter: https://x.com/JacquelineSYC19

LinkedIn: https://www.linkedin.com/in/jacqueline-cheong

Follow Turner

Twitter: https://twitter.com/TurnerNovak

LinkedIn: https://www.linkedin.com/in/turnernovak

Subscribe to my newsletter to get every episode + the transcript in your inbox every week: https://www.thespl.it/

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