Duke dropout One Chowdhury pulls back the curtain on the lies we believe about startups, success, and what it really takes to challenge a $300B giant like Salesforce.
One Chowdhury is the CEO of Octolane, a Y Combinator-backed startup that raised $2.6M to build the first self-driving AI CRM. A self-taught coder who left Duke University to pursue his vision, he learned the pain of manual CRM entry during his internship at Mintlify. Now he’s confronting startup myths - from why focus trumps talent to how AI can transform sales workflows, freeing reps from tedious data entry.
In this episode, One Chowdhury reveals:
◽️ The SHOCKING Salesforce flaw reps hate!
◽️ Why he ditched Duke for startups!
◽️ The AI trick outsmarting CRM giants!
◽️ How Octolane’s $2.6M raise happened fast!
◽️ The mindset to beat impossible odds!
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⏱ Timestamps
00:00 Intro
00:32 One’s discovery of Salesforce’s flaws
01:15 The emotional spark: Sales reps’ struggles
02:18 What Salesforce does and why it fails
02:47 Pain of manual CRM data entry
03:30 Why One chose to target Salesforce
04:51 Skepticism from others about his vision
05:06 Overcoming the “impossible” mindset
05:52 Silicon Valley’s hustle: Key lessons
06:30 Mintlify’s influence on One’s approach
07:17 Downsides of startup life exposed
10:33 Mintlify internship: Building AI products
11:50 Learning to ship fast, iterate later
12:46 Octolane’s self-driving AI CRM vision
14:20 How Octolane automates sales workflows
15:45 Early challenges: Gaining customer trust
18:06 Why focus beats shiny AI distractions
21:58 Coding as a superpower for all
23:15 High school project with 300,000 users
25:11 Why Duke was the right choice
26:10 Cultural shock at Duke University
30:34 AI tools like Cursor and Lovable
31:15 Can non-technical founders succeed?
33:00 Grit and discipline fuel Octolane’s rise
36:49 Biggest hurdle to beating Salesforce
39:11 Staying focused for a 10-year mission
40:30 Why Salesforce isn’t the real threat
42:40 Spotting real AI startups vs hype
44:15 Net Revenue Retention: The success metric
46:30 How One raised $2.6M so fast
48:00 Y Combinator’s role in Octolane’s growth
49:30 AI’s real-world impact on sales
58:49 Balancing AI rewards with safety
1:03:13 One’s legacy: Inspiring bold action
1:03:41 Next goal: Switch 100 companies
1:04:14 One’s advice: Focus and agency
1:06:51 Final reflections & takeaways
📌 Resources
One Chowdhury:
◽️ LinkedIn: https://www.linkedin.com/in/coffeewithone/
Harvey Bracken-Smith:
◽️ LinkedIn: linkedin.com/in/harveybracken-smith
◽️ Instagram: instagram.com/harveybsmith
◽️ X (Twitter): x.com/harveybsmith_
Personable Podcast:
◽️ Instagram: instagram.com/personable.podcast
◽️ LinkedIn: linkedin.com/company/personablepodcast
◽️ TikTok: tiktok.com/@personableclips
◽️ Spotify: open.spotify.com/show/7JOTYDER6m2FDrlhop4api
◽️ Apple Podcasts: podcasts.apple.com/us/podcast/personable/id1671640111
Additional:
◽️ The Draft (Sign up): thedraft.io
◽️ Fundraising: justgiving.com/crowdfunding/LouLouRacefoiundation?utm_term=PvByaxmdn
Personable is a podcast dedicated to helping listeners become the best they can be by learning from the world’s best in their respective fields. This mission is inspired by my mother, Louise, who encouraged me to become the best version of myself before she passed away from cancer in 2023.
This content is for informational and entertainment purposes only and is not financial advice. Always consult a qualified financial advisor before making investment decisions. Investing involves risks, and past performance is not indicative of future results.

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