How Skydo Found Product-Market Fit in India’s Cross-Border B2B Payments

Building A Prosumer AI Startup: The Merlin Story

This episode delves in-depth into building a Prosumer AI startup. We cover everything from overlooked spaces in AI, how to choose problem statements as a founder, learnings on upfront market research & customer discovery, creating defensibility in Prosumer AI, managing the foundation model layer, including closed source vs open source, Prosumer GTM, particularly influencers and affiliate marketing, new usage-based pricing models, fundraising learnings and finally, specific learnings for US-India founders. Joining me for this discussion is Pratyush Rai, Co-founder of Merlin, an AI productivity assistant that you can use for everything from getting one-click answers to summarizing & repurposing content, and much more. Pratyush is an IIT grad, worked with BCG in the past, before starting Merlin with two of his batchmates, and has now scaled it to 2M+ users. Merlin was recently covered in A16Z's top 50 AI apps where startups spend money. TIME STAMPS: (01:27) What spaces in AI are being overlooked? (05:26) Building a Prosumer AI startup: the Merlin backstory (09:41) Choosing AI problem statements to work on (20:21) Doing effective customer discovery (21:12) Competition & differentiation (24:15) Creating defensibility as a Prosumer AI product (30:33) AI front-end experiences: Browsers and Chrome Extensions (34:03) Managing the foundation model layer: closed vs open source  (42:46) GTM Approaches for Prosumer AI: Influencers & Affiliate Marketing (57:08) Pricing learnings for Prosumer AI startups: usage-based (1:05:55) Fundraising learnings for Prosumer AI founders (1:12:54) One hard-earned lesson for US-India founders Connect with Pratyush on LinkedIn - https://www.linkedin.com/in/pratyush-rai/ and follow him on X - @pratyush_r8 ***** Check out "An Operator's Blog" (https://operator.blog/) for weekly posts on Startups, Investing, and Life. I am a venture investor focused on the US-India corridor. Feel free to reach out on LinkedIn (https://www.linkedin.com/in/soumitrasharma5/) and follow me on X (@soumitra_sharma).

Agentic AI Meets Compliance: Lessons From Sprinto

This episode delves in-depth into building an AI Applications startup in the area of Compliance.  We cover everything from how to choose problem statements as a founder including a 2x2 framework for idea evaluation, approaching building in “boring” verticals, executing an effective customer discovery process, thinking through product differentiation in the Applications layer, evolution of GTM in the age of AI, new-age pricing models, present state of AI fundraising in the Bay Area, and finally, specific learnings for US-India founders. Joining me for this discussion is Girish Redekar, Co-founder of Sprinto, a unified, AI-powered compliance platform that enterprises can use to manage compliance standards such as SOC 2, ISO 27001, HIPAA, and GDPR. Before Sprinto, Girish founded RecruiterBox in the HRTech space, which was acquired by TurnRiver Capital. TIME STAMPS: (01:17) What parts of the AI ecosystem are under-hyped? (05:31) Choosing unsexy verticals: the Sprinto backstory (11:48) Choosing the right problem statements in AI (17:21) Product Risk vs Market Risk: a 2x2 framework for evaluating startup ideas (21:12) Competition & differentiation (25:41) Staying on top of rapid changes in the foundational model layer (31:37) AI’s impact on GTM (37:41) AI adoption apprehensions of enterprise customers (42:27) Ground reality of AI-first pricing models (47:03) Bay Area fundraising advice for AI Applications startups (51:18) A hard-earned lesson for US-India founders Connect with Girish on LinkedIn - https://www.linkedin.com/in/girishredekar/ and follow him on X - @grease_ ***** Check out "An Operator's Blog" (https://operator.blog/) for weekly posts on Startups, Investing, and Life. I am a venture investor focused on the US-India corridor. Feel free to reach out on LinkedIn (https://www.linkedin.com/in/soumitrasharma5/) and follow me on X (@soumitra_sharma).

Building An AI-Infra Startup In 2025: Seed-Stage Lessons From Pipeshift

This episode delves in-depth into the present market landscape, challenges & opportunities being navigated by AI infra startups in the Bay Area.  We cover everything from parts of the AI ecosystem that are overhyped and underhyped, real AI infra pain points & apprehensions of enterprise customers, nuances of leveraging closed source vs open source models in enterprise infra, discovering gaps & wedges as a startup, creating differentiated products against competition, AI-first GTM, new-age pricing models and finally, lesser-known aspects of fundraising in the Bay Area. Joining me for this discussion is Arko, Co-founder and CEO of Pipeshift, a YC-backed startup that's building reliable and SLA-compliant inference-as-a-service for real-time AI applications in production. He and his co-founders started building products together as undergraduates, participating in hackathons over six years ago, and today they are building a best-in-class AI infrastructure company right here in the Bay Area. TIME STAMPS: (01:43) What parts of the AI ecosystem are under-hyped? (07:48) The Pipeshift backstory (11:23) The unique value of building in the Bay Area (16:31) Choosing the right problem statements (21:34) Competition & differentiation (25:22) AI infra pain points of enterprise customers today (32:24) Staying on top of rapid changes in the foundational model layer (42:48) Customer approach on closed vs open source models (48:02) Ground reality of AI-first pricing models (51:44) Early stage GTM learnings in AI infra (59:55) Bay Area fundraising advice Connect with Arko - https://www.linkedin.com/in/arkoc/  ***** Check out "An Operator's Blog" (https://operator.blog/) for weekly posts on Startups, Investing, and Life. I am a venture investor focused on the US-India corridor. Feel free to reach out on LinkedIn (https://www.linkedin.com/in/soumitrasharma5/) and follow me on X (@soumitra_sharma).

From Zero to $1M ARR: Building a US–India Enterprise Dev Tools Startup

This episode goes in-depth into the key operating aspects of building & scaling a US-India Enterprise Dev Tools Startup.  We cover everything from the ground reality of how AI is impacting enterprise dev tools, why engineering founders should code less & sell more, thinking through ICPs, MVP best practices, GTM approaches, including outbound and events, the importance of founder-led sales, and finally, how pricing models are evolving with AI. Joining me for this discussion is Sudheer Bandaru, Founder & CEO of Hivel. Hivel is a B2B SaaS solution that helps companies improve engineering productivity and release better software faster by providing interactive dashboards for visibility and actionable insights to enhance software delivery. Sudheer has been a long-time CTO and engineering leader, taking multiple startups from the garage to public listings. TIME STAMPS: (01:23) How will AI impact the way value gets created across functions (05:47) The Hivel backstory: Making engineering teams high-velocity (12:00) Why engineering founders should code less & sell more (15:00) Thinking through your ICP (18:45) MVP best practices (21:14) Leveraging AI as an enterprise dev tools startup (25:27) GTM approaches for enterprise dev tools (28:05) Crafting a go-to-market funnel for a new category (33:26) Structuring the sales org. (36:59) Approaching org. design in the age of AI (40:49) Ground reality of AI-first pricing models Connect with Sudheer - https://www.linkedin.com/in/sbandaru/ and follow him on X - @sudheerbandaru_ ***** Check out "An Operator's Blog" (https://operator.blog/) for weekly posts on Startups, Investing, and Life. I am a venture investor focused on the US-India corridor. Feel free to reach out on LinkedIn (https://www.linkedin.com/in/soumitrasharma5/) and follow me on X (@soumitra_sharma).

How Skydo Found Product-Market Fit in India’s Cross-Border B2B Payments

This episode goes in-depth into Skydo’s journey from Day 0 to emerging as a category leader in India's cross-border B2B payments today, helping more than 6,000 Indian products & services exporters receive payments from 150+ countries & in 32+ currencies. We cover everything from the untapped cross-border payments opportunity, learnings from fintech MVP iterations, doing customer research to identify unique product & business model insights, the philosophy of "do things that don’t scale" and figuring out differentiation pre-PMF, leveraging founder-led sales to acquire early customers, building a culture of radical transparency, learnings from VC fundraising and finally, Skydo’s plans for the next 2 years.  Joining me for this discussion are Skydo's co-founders - Movin Jain and Srivatsan Sridhar. Previously, Movin held leadership roles at PhonePe, Meesho & Ola, and Srivatsan at McKinsey, Ola, and Rupeek. TIME STAMPS: (01:00) The Skydo backstory (04:08) Why cross-border payments is an untapped opportunity (09:10) Iterating a fintech MVP (16:54) Examples of “do things that don’t scale” in fintech (20:47) Figuring out product differentiation at the early stages (26:52) Importance of intellectual humility (30:09) Finding early adopters in a high-trust business like fintech (35:01) Right-sizing the early sales team (36:53) Optimizing the marketing funnel  (42:51) Doing “unscalable” founder-led customer service to differentiate  (44:59) How to discover what to build or improve in a B2B payments product (51:37) Building a culture of radical transparency (59:30) Learnings from VC fundraising  (1:07:38) Navigating cross-border payments regulations (1:14:35) Why should Indian exporters prefer Skydo over traditional banks? Connect with Movin - https://www.linkedin.com/in/movinjain/ and Srivatsan - https://www.linkedin.com/in/srivats80/ ***** Check out "An Operator's Blog" (https://operator.blog/) for weekly posts on Startups, Investing, and Life. I am a venture investor focused on the US-India corridor. Feel free to reach out on LinkedIn (https://www.linkedin.com/in/soumitrasharma5/) and follow me on X (@soumitra_sharma).