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).

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).

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).

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).

This episode goes in-depth into the key operating aspects of finding & working with US design partners as a US-India cross-border founder. 

We cover everything from correctly defining who a design partner is, major categories and personas on the B2B side, discovering, qualifying, convincing & engaging them including navigating their organization structure, partnering with them to build early versions of the product, tension between direct sales & channel partner models, how to approach pricing discussions and finally, a rapid-fire round of questions sourced from An Operator’s Blog founder community. 

Joining me for this discussion is Indus Khaitan, Founder & CEO of Redblock, a cybersecurity startup that provides identity security for disconnected apps using Agentic AI. Before this, Indus founded Quolum in the SaaS spend management space and also founded Bitzer, which was an early mobile security platform and was acquired by Oracle. He is a long-time champion, advisor & investor in the US-India venture corridor.  

TIME STAMPS:

(02:10) The early days of mobile security, iPhone 1, and starting Bitzer

(04:39) The definition & value of a 'design partner'

(08:25) Major categories of design partners 

(11:29) Navigating through the org. structure of design partners

(15:04) Should US-India B2B startups enter the US via a channel partner model?

(19:02) Dealing with friendly vs cold/ outside-network design partners

(23:36) Generating US design partner leads

(27:57) Qualifying potential design partner leads

(30:20) Prioritizing between SMB vs mid-market vs enterprise design partners

(38:03) Reasons why founders’ and investors’ POVs on the business direction often diverge 

(41:53) Most useful social media platforms for 0-to-1 founders

(45:14) Are offline events & conferences useful for early-stage founders?

(53:41) Approaches & frameworks for building B2B software MVPs

(59:54) Approaching pricing conversations with design partners

(1:03:06) Rapid-fire round

Connect with Indus - https://www.linkedin.com/in/khaitan/ and follow him on X - @1ndus

*****

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).

This episode goes in-depth into the key operating aspects of building & scaling a US-India cross-border AI startup serving the US financial services market.

We cover everything from customer behavior & AI adoption patterns by large US financial services enterprises, approaches & frameworks for building fintech MVPs, state-wise & country-wise regulatory & business nuances, AI’s impact on fintech product roadmaps, tactics for US-India fintech software founders to find US design partners, go-to-market approaches for large enterprise GTM, emerging AI-driven fintech software pricing models, building a US fintech GTM team as a US-India founder, and finally, learnings from fintech fundraising in the Valley.

Joining me for this discussion is Shantanu Gangal, Founder & CEO of Prodigal, an AI platform for loan servicing & collection agents, both human and virtual. Prodigal’s Intelligence Engine touches ~40 million consumers in the US, Canada & UK. The company is backed by top-tier VCs like Accel & Menlo.

TIME STAMPS:

(01:15) AI’s impact on the US fintech software landscape

(08:22) Backstory of Prodigal

(12:02) Approaches & frameworks for building fintech MVPs

(15:42) State-wise & country-wise regulatory & business nuances

(21:44) Importance of meeting customers in person

(23:59) AI’s impact on fintech software product roadmaps

(32:59) Tactics for US-India fintech software founders to find US design partners

(37:25) Go-to-market motions for a US-India fintech software startup

(42:20) AI’s impact on fintech software pricing models 

(46:45) Building a US fintech software GTM team as a US-India founder

(50:26) Learnings from fintech fundraising in Silicon Valley

Connect with Shantanu - https://www.linkedin.com/in/shantanugangal/ and follow him on X - @shantanugangal

*****

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).

This episode explores US GTM strategies, playbooks, and learnings for US-India B2B founders. We cover everything from the playbook for finding the shortest way to PMF with the least capital raised, step-by-step framework for building B2B software MVPs, nuances of serving customers in the US vs India, finding US design partners including the best ways to generate leads & get warm intros, and finally, the importance of spending frequent & quality time with customers.

Joining me for this discussion is Srinivasan Narayan (Srini), Co-founder and CEO of Goodmeetings, an AI-powered Meeting Insights & Automation Platform designed to enhance the performance of customer-facing revenue teams. Prior to this, Srini co-founded CohortPlus, an edtech startup that was acquired by upGrad.

TIME STAMPS:

(01:05) The game-changing nature of AI

(05:57) The backstory of Goodmeetings, how repeat founders do things differently

(13:28) Surviving tech cycles & disruptions

(17:22) Approaches & frameworks for building B2B software MVPs

(21:41) The playbook for finding the shortest way to PMF with the least capital raised

(28:29) Nuances of serving customers in the US vs India

(40:24) Finding design partners in the US, leveraging extended networks & cold emailing

(46:42) Importance of spending time with customers 

Connect with Srini - https://www.linkedin.com/in/srinivasan-narayan-5834928/ and follow him on X - @naryansrini

*****

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).

This episode goes in-depth into what founders can do to engineer & navigate an exit for their startup. We cover everything from various types of exit routes (classic M&A, Private Equity buyouts, acqui-hires, asset sales, etc.), what large acquirers look for, generating acquisition interest, fielding corp dev inbounds, valuation methods, key deal terms, how to become diligence-ready, and finally, leaning on investors, bankers, lawyers & advisors to help drive an exit.

Joining me for this discussion are Madhu Chamarty and Hanz Kurdi, Founding Partners of HKMC, a Silicon Valley-based advisory firm that supports early-stage founders and emerging VC managers in achieving their most important milestones, including fundraising, go-to-market, and exits. Each of them has 20+ years of experience in navigating exits. Hanz’s prior startups were acquired by PayPal and Google, while Madhu’s prior HRTech startup was acquired by Lightcast.

TIME STAMPS:

(01:06) The HKMC backstory

(05:57) Today’s AI exit environment

(12:37) What do large tech acquirers look for in potential M&A targets?

(23:13) Is Private Equity a viable exit channel for software startups?

(26:23) Should founders entertain inbounds from corp dev?

(32:24) What can founders do to create a “salvage exit” in case they don't achieve PMF?

(43:40) What can founders at $10-100Mn ARR do to engineer an exit?

(52:40) How do acquirers typically value startups?

(58:38) How do acqui-hire deals work? 

(1:00:36) Key legal terms during M&A deals

(1:05:00) How can founders become M&A diligence-ready?

(1:11:51) What can VCs do to help drive exits for their portfolio?

(1:20:58) When do M&A advisors/ I-bankers become relevant in a company's lifecycle?

Connect with Madhu - https://www.linkedin.com/in/mchamarty/ and Hanz - https://www.linkedin.com/in/hanzkurdi/

*****

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).

This episode discusses the ground realities and daily challenges of moving to the US to build your startup as an India-based founder. We cover everything from the first 90 days, logistics & compliance issues, acquiring early US customers, evolving the product roadmap from Indian to US customers, setting PMF goals & KPIs, relationship-building & other US GTM tips.

Joining me for this discussion is Prashant Mahajan, an accomplished product leader and founder with more than a decade of experience in product management. His most recent adventure was as the Founder of Zeda, a venture-backed startup in the space of AI-powered product management tools. Before this, Prashant was a product leader at Branch, Tokopedia, and Paytm.

TIME STAMPS:

(1:47) Bittersweet thoughts at the end of a startup journey

(4:42) How does an India-based founder figure out the correct timing for the US move?

(9:17) Day-to-day challenges of a US-India founder, dealing with loneliness

(15:36) Acquiring early US customers

(19:27) Evolving the product roadmap as GTM shifts from India to the US

(23:55) How to set PMF goals & KPIs while moving to the US as an India-based founder

(26:53) What stopped working for Zeda?

(35:33) When should founders pivot? Or even quit?

(41:05) Relationship-building advice for US-India founders

Connect with Prashant - https://www.linkedin.com/in/prashantmahajan31/ and follow him on X - @Pmahajan3105

*****

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).

Most investors try to “slot” startups in their heads, whereas extraordinary venture outcomes lie in the “slot violations”.

Source post - https://operator.blog/2025/02/13/insight-arbitrage/

*Audio Overviews generated via NotebookLM.

*****

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).