Jesse Zhang - Building Decagon - [Invest Like the Best, EP.443]

Invest Like the Best with Patrick O'Shaughnessy

Colossus

Technology, Business, Investing

4.7 • 2.5K Ratings

🗓️ 6 October 2025

⏱️ 83 minutes

🔗️ Recording | iTunes | RSS

🧾️ Download transcript

Summary

My guest today is Jesse Zhang. Jesse is the co-founder and CEO of Decagon, one of the fastest-growing AI customer service companies. Decagon provides a centralized AI engine to auto-resolve issues at any time, in every language, and across every channel. Jesse shares his systematic approach to finding product-market fit by asking potential customers exactly how much they'd pay for solutions. We explore why customer service and coding have emerged as the two clearest AI use cases for enterprises, and the key business and technical factors behind Decagon's momentum. We discuss the intense competitive dynamics of building in AI today, strategic decisions around building proprietary models, and deploying AI agents at enterprise scale. Please enjoy my conversation with Jesse Zhang. For the full show notes, transcript, and links to mentioned content, check out the episode page ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠here⁠⁠⁠⁠⁠⁠.⁠⁠⁠⁠⁠⁠⁠⁠ ----- This episode is brought to you by⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ Ramp⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠. Ramp’s mission is to help companies manage their spend in a way that reduces expenses and frees up time for teams to work on more valuable projects. Go to⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ Ramp.com/invest⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ to sign up for free and get a $250 welcome bonus. – This episode is brought to you by⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ Ridgeline⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠. Ridgeline has built a complete, real-time, modern operating system for investment managers. It handles trading, portfolio management, compliance, customer reporting, and much more through an all-in-one real-time cloud platform. Head to⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ ridgelineapps.com⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ to learn more about the platform. – This episode is brought to you by⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ AlphaSense⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠. AlphaSense has completely transformed the research process with cutting-edge AI technology and a vast collection of top-tier, reliable business content. Invest Like the Best listeners can get a free trial now at⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ Alpha-Sense.com/Invest⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ and experience firsthand how AlphaSense and Tegus help you make smarter decisions faster. ----- Editing and post-production work for this episode was provided by The Podcast Consultant (⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://thepodcastconsultant.com⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠). Show Notes: (00:00:00) Welcome to Invest Like the Best (00:05:49) Building a Company in a Competitive Market (00:07:26) Personal Background and Competitive Upbringing (00:10:32) Challenges and Lessons from Previous Ventures (00:12:21) Ideation and Customer Discovery Process (00:19:31) Developing and Refining AI Customer Service Agents (00:32:26) Voice AI and Future Prospects (00:38:20) Utilizing Customer Interaction Data (00:39:59) Frameworks for Implementing AI in Business (00:41:48) Evaluating the ROI of Coding Agents (00:42:53) The Future of Company Agents (00:45:15) Brand Personality in AI Agents (00:47:48) Investor Interest in AI Companies (00:54:32) The Competitive Landscape of AI Talent (00:57:21) Building Proprietary AI Models (01:10:36) Customer Qualification and Engagement (01:17:27) The Kindest Thing

Transcript

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0:00.0	The best operators have a relentless focus on leverage, finding ways to multiply their impact
0:04.7	rather than just working harder. But here's what I see happening in finance teams everywhere,
0:09.0	brilliant people getting buried in expense management busy work. If you think about it,
0:12.8	you become a finance leader because you love strategic work, modeling scenarios, optimizing capital
0:17.2	allocation, finding the insights that actually move the business forward. But instead,
0:20.8	you're chasing receipts and categorizing transactions.
0:23.1	It's the opposite of leverage.
0:24.8	This is exactly why I'm so bullish on what the team at Ramp has built.
0:28.5	Kareem and Eric understood that every minute spent on manual expense management is a minute
0:32.4	stolen from high leverage work.
0:34.0	So they automated all of it.
0:35.6	Automatic categorization, receipt matching, spending controls that
0:38.6	actually work. I love the network effect that this creates. When finance teams at companies like Shopify
0:43.7	and Stripe automate the mundane stuff, they free up cycles to think bigger, to ask for your questions,
0:48.5	spot patterns others miss, and make the kind of strategic bets that separate great companies from good
0:53.0	ones. The math is simple. Get your time back, focus on what matters.
0:57.2	Check out ramp.com slash invest and see what happens when you eliminate the busy work.
1:01.4	Cards issued by Sutton Bank, member FDIC, terms and conditions apply.
1:05.7	In asset management, growth often depends on customization.
1:08.6	It's the nature of the beast in our industry, and I know having
1:11.1	experienced the problem firsthand as an active manager, it's a competitive differentiator to tailor
1:15.8	products and services to clients' preferences. Those of us growing our businesses always want to say yes
	...

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