Today's guest watched digital transformation projects fail for years. Not because the tech was broken — the governance was. The values had drifted. And nobody noticed until it was too late.

So he did something unusual. He went back 2,000 years to Tamil philosophy — specifically a tradition called Saiva Siddhanta — and built a framework that treats ethics not as a compliance checkbox, but as the actual operating system.

Vendan Kumararajah is a transformation architect, cybernetician, and the creator of something called the A3 Model. His new book "Navigating Complexity and System Challenges" makes a bold claim: that we can design AI systems that don't just follow ethical rules, but actually enact ethical intelligence in real time.

So today we're going to unpack what the A3 Model actually is. And pressure-test it against real founder scenarios.

Key Discussion Points:

🔥 You can't have a dynamic system with a static rule-based.

🤖 Static rules cannot evolve in a dynamic environment because there is distortion at every stage.

🚨 Distortion is when the journey starts for a system.

👥 Ethics, distortion, and agency as a self-regulating, self-evolving structure.

📊 The ethical coherence is a red line because it shows the harm limits.

💡 What looks like success may be actually a time bomb waiting to explode.

🚨 The A3 model starts warning every time, regardless of what the KPIs are showing.

Important Links:

You can reach Vendan Kumararajah at https://www.linkedin.com/in/vendan-kumararajah-1049634

Checkout his book, Navigating Complexity and System Challenges: Foundations for the A3 Model

at https://www.amazon.co.uk/dp/1919249303?source=ps-sl-shoppingads-lpcontext&ref_=fplfs&psc=1&smid=A3P5ROKL5A1OLE

Vishesh, your host at https://vishesh.space

P.S. If you are writing on LinkedIn https://tryjerry.com

This episode is about what happens when you win — and still feel lost.

My guest Sama went from hospital clown to cybersecurity founder to a successful exit. And on this episode we get into the stuff nobody talks about after an acquisition — the identity crisis, the scars, the 'now what.'

We also unpack his clown mindset framework — this idea that failure is success — why he's now building AI to keep miners alive in Peru, and the two startups that failed before the one that worked. If you're a founder questioning your path, this one's going to hit.

Key Discussion Points:

🔥 How to identify and mitigate risks when applying AI in unexpected industries

🤖 The surprising ways AI can improve safety in heavy industries like mining

💡 What it takes to implement AI in complex industries

🚀 How to navigate the challenges of applying AI in industries with limited digital infrastructure

💻 The importance of understanding the unique needs and pain points of each industry when applying AI

Timecodes:

0:00 - Introduction

0:15 - Overview of Misty AI and Its Mission

1:52 - The Importance of Safety in Mining

6:28 - Identifying Buyer Personas in Heavy Industry

11:30 - The Co-Founder Dating Phase: Finding the Right Partner

14:52 - Insights from Clowning: Lessons for Founders

24:36 - Embracing Failure: Lessons from Clowning

26:38 - Previous Startups: Experiences and Learnings

28:56 - Transitioning from Investor to Co-Founder

31:51 - Reflections on the Exit from Boxee HQ

37:58 - Understanding the Gap Between Startups and Enterprises

40:47 - Strategies for First-Time Founders in Enterprise Sales

42:20 - Advice for New Entrepreneurs: Enjoy the Journey

43:07 - Balancing Family Life with Startup Challenges

45:54 - Final Thoughts for Founders in Heavy Industry

47:10 - How to Connect with Sama and Misty AI

Important Links:

You can reach 🚁 Sama Carlos Samame at https://www.linkedin.com/in/samame

Vishesh, your host at https://vishesh.space

Checkout MISTI AI at https://mistiai.com

P.S. If you are writing on LinkedIn https://tryjerry.com

Episode 58 with Vikram Das, Co-Founder & CEO at Yasu.I'm joined by Vikram Das, the Co-Founder & CEO of Yasu. Vikram spent two decades in the industry with stints at Cognizant, and AWS. He went from closing 50 million dollar cloud deals for AWS to walking into a room of 70 strangers in Amsterdam to find a Dutch co-founder he'd known for weeks, and they recently raised a little over 1 Million dollars to solve the exact problem he helped create! In this episode we talk about what does it take to build an AI Cloud Engineer, finding co-founder love and losing it, Challenges of being immigrant founder in Europe, Some of his learnings from their fundraising journey through all the bubble talk and more!Key Discussion Points:🔥 Fundraising is something that every founder is concerned about. Is it a necessary evil, or can you find alternative ways to secure funding?🤯 What are the unique challenges faced by Indian-origin founders in Europe, particularly in tech, and how can they overcome them?🚀 How can founders balance their mental health while navigating the startup journey, and what role does mindfulness play in this process?📈 What are the cultural differences between startup environments in Europe and India, and how can founders adapt to these differences?💡 Why is distribution the only key that is going to be, and how can founders prioritize it in their fundraising strategies?Timecodes:0:00 - Introduction2:15 - Discussing the Importance of Fundraising5:30 - Insights on Fundraising in the European Context8:45 - The Challenges of Fundraising for Founders12:00 - Navigating the Cloud Complexity in Startups15:20 - The Role of AI in Cloud Engineering18:30 - Team Building and Early Hiring Strategies21:00 - The Experience of Indian Founders in Europe24:15 - Balancing Startup Life with Personal Well-being27:30 - The Impact of Mental Health on Founders30:00 - The 996 Work Culture in European Startups33:15 - Exploring the Future of AI in Business36:00 - Building a Podcast as a Distribution Engine39:30 - The Journey of Transitioning from Corporate to Startup42:00 - Creating Content in a Saturated Market45:15 - The Importance of Authenticity in Content Creation48:30 - Final Thoughts and Future Plans51:00 - Closing Remarks and Next StepsImportant Links:You can reach Vikram Das at https://www.linkedin.com/in/dasvikramVishesh, your host at https://vishesh.spaceCheckout Yasu at https://yasu.cloudP.S. If you are writing on LinkedIn https://tryjerry.com🎙️ Subscribe for more episodes!#Episode58 #VenturingWithVishesh #Startups #Entrepreneurship #startups #entrepreneurship #venturingwithvishesh

I'm joined by Ryan Kalisky, Co-Founder and CEO of WareMatch, a platform connecting suppliers and 3PL vendors globally.

As a 26-year-old McGill finance grad, Ryan is trying to disrupt an unglamorous $1 plus trillion logistics industry. We explore the honest reality of early-stage marketplace building, the hacks they’ve used so far, and more.

I am always excited to talk to marketplace founders, and listening to how WareMatch is building a 3PL marketplace should be gold for any founder building a marketplace!

Key Discussion Points:

🔥 How a finance degree led to a career in warehousing and logistics

💡 The surprising opportunity that arose during the COVID-19 pandemic

🤝 Building a network of medical supply companies and leveraging it for other opportunities

📈 The gap in the 3PL quoting market and how WareMatch is addressing it

🚀 The importance of building a strong team and outsourcing to the right people

💻 The challenges of building software in an industry with complex regulations and certifications

📊 How to create a user-friendly software solution that meets the needs of 3PL companies

Timecodes:

0:00 - Introduction

1:30 - Transition from Finance to Warehousing

4:00 - The Impact of COVID on Supply Chains

6:15 - Starting a Medical Supply Business

9:00 - Building a Network in the Medical Supply Space

11:30 - Identifying Gaps in the 3PL Market

14:00 - The Concept of a Matchmaking Platform for Warehouses

16:30 - The Importance of Team Dynamics in Startups

19:00 - Finding the Right Technical Co-Founder

21:30 - Challenges in the 3PL Industry

24:00 - Overview of Third-Party Logistics (3PL)

26:15 - The Bidding System for 3PLs

28:00 - Marketing Solutions for Warehouses

30:30 - Competing with Established Companies in the 3PL Space

33:00 - Lessons Learned as a First-Time Founder

35:30 - The Importance of User Feedback

38:00 - Strategies for Building a Marketplace

40:30 - Managing Team Dynamics and Personal Challenges

42:00 - Conclusion and Future Plans

43:30 - Where to Find More Information on WareMatch

Important Links:

You can reach Ryan Kalisky at https://www.linkedin.com/in/ryan-kalisky-25bba21490625

Vishesh, your host at https://vishesh.space

Checkout WareMatch at https://www.warematch.com/

P.S. If you are writing on LinkedIn https://tryjerry.com

🎙️ Subscribe for more episodes!

#Episode57 #VenturingWithVishesh #Startups #entrepreneurship #venturingwithvishesh

I'm joined by Saher Shodhan, founder of Thera Travel, a startup that's disrupting the healthcare industry by providing patients with access to affordable and high-quality medical care abroad. With a background in marketing and growth, Saher has leveraged AI tools to drive growth and reduce marketing costs by 10x. In this conversation, we dive deep into the challenges of building a successful startup, the role of AI in healthcare, and how Thera Travel is making a difference in people's lives.Key Discussion Points:🔥 What sparked the idea for Thera Travel and how Saher identified a problem in the healthcare system🚀 How Saher used AI tools to reduce marketing costs by 10x and drive growth🤖 The role of AI in healthcare and how Thera Travel is disrupting the industry💡 The importance of understanding government data and using it to drive business decisions📈 How Saher built a successful startup from scratch, from idea to exit in four yearsTimecodes:0:00 - Introduction0:36 - The Spark Behind TheraTravel4:45 - The Journey of a Solo Founder7:06 - Using AI for Marketing and Content Creation16:09 - The Truth Behind Startup Valuations19:51 - Navigating the Challenges of AI in Business22:10 - Lessons from the Traktion Journey24:12 - Finding the Right Acquirer for Your Startup36:45 - Evolving Advertising Strategies in 202642:28 - Rethinking Team Size as a Success Metric43:18 - The Reality of Fundraising Celebrations44:52 - Learning from Failures in Startup Growth48:24 - Selling Growth Strategies to Startups51:11 - Analyzing Competitor Success in Marketing52:46 - Recommended Reading for Founders54:45 - Closing Remarks and Contact InformationImportant Links:You can reach Saher Shodhan at https://www.linkedin.com/in/sahersVishesh, your host at https://vishesh.spaceCheckout Thera Travel at http://theratravel.co.uk/P.S. If you are writing on LinkedIn https://tryjerry.com🎙️ Subscribe for more episodes!#Episode56 #VenturingWithVishesh #Startups #Entrepreneurship

I'm joined by Scott Persinger, Co-founder and CTO of BizTrip AI, a company focused on utilizing AI technology to enhance corporate travel management. With a background in software development and a passion for innovation, Scott has led BizTrip AI from its inception to become a leader in the AI-powered travel industry. In this conversation, we dive deep into the challenges of integrating AI into legacy travel tech stacks and the strategic decision to target the B2B market.

The travel industry is ripe for transformation with AI, but it's not just about implementing technology - it's about understanding the underlying challenges and creating solutions that truly serve the needs of users. Scott Persinger, Co-founder and CTO of BizTrip AI, shares his insights on debunking AI myths, building features that customers want, and the importance of cross-functional experience in understanding different roles within a company.

Timecodes:

0:00 - Introduction

2:42 - Choosing B2B Over B2C in Travel AI

5:35 - Challenges of Integrating AI with Legacy Systems

9:08 - Scott's Engineering Background and Current Tech Stack

11:14 - The Evolution of AI Tools in Development

13:09 - Fine-Tuning AI Models for Specific Use Cases

14:38 - Misunderstanding AI's Capabilities in Software Development

20:34 - The Importance of Customer Insights in Product Development

26:32 - Future of AI in Travel Tech: Contextual Understanding

34:44 - The Importance of Historical Data in AI Recommendations

36:22 - Learning from Memorable Failures in Startups

39:33 - Evolving Leadership Styles in Tech Teams

42:07 - Advice for New Engineers: Networking Beyond Tech

47:25 - Lessons from Stripe

52:43 - Closing Remarks and Contact Information

Important Links:

You can reach Scott Persinger at https://www.linkedin.com/in/scottpersinger

Vishesh, your host at https://vishesh.space

Checkout BizTrip AI at https://biztrip.ai

P.S. If you are writing on LinkedIn https://tryjerry.com

I'm joined by Brian Leor Frankel, Growth Consultant at Ignite.Consulting, with a background in market research and over 20 years of experience in B2B campaigns. With a passion for teaching and helping startups scale, Brian brings a unique perspective on customer acquisition cost optimization and marketing strategy.

Optimizing customer acquisition costs is crucial for startups and entrepreneurs. In this conversation, we dive into the art of CAC optimization, exploring strategies for bringing down customer acquisition costs and scaling marketing efforts. We discuss the importance of understanding customer desires and fears, creating effective messaging, and leveraging AI to improve marketing performance.

Key Discussion Points:

🔥 What's the one thing that's holding you back from achieving profitable growth?

🤔 How to identify the 20% of your marketing efforts that drive 80% of your results

📈 The surprising way to bring down customer acquisition costs by 50% or more

📊 Why most founders get AI implementation completely wrong (and how to do it right)

💡 The counterintuitive way to create messaging that resonates with your target audience

📈 How to use data to inform your marketing decisions and drive real growth

Timecodes:

0:00 - Intro

2:20 - Why CAC Starts High for Startups

6:39 - Identifying the Core Value Proposition

9:27 - How to Find & Test Messaging

13:40 - Testing Angles, Hooks & Visuals

15:55 - Budgeting Ad spend

19:07 - Using AI for Quick Sentiment Analysis

21:17 - The 5-Step Consumer Purchase Process (CPP)

30:56 - How AI Enhances the Consumer Purchase Process

32:02 - Personal Section: Long COVID & Recovery Journey

36:30 - Slowing Down While Still Being Results-Driven

37:58 - Working With Keith Ferrazzi

38:40 - Lessons From “Never Eat Alone” & Networking

40:50 - Why You Must Still Learn to Know People Yourself

41:33 - Final Thoughts on Running Campaigns Across Platforms

44:24 - Where to Find Brian Online

44:54 - Closing Thanks

Important Links:

You can reach Brian Leor Frankel at https://www.linkedin.com/in/brianfrankel

Vishesh, your host at https://vishesh.space

Checkout Ignite.Consulting

P.S. If you are writing on LinkedIn https://tryjerry.com

David Abaev is the founder of Databar.ai; a powerful, plug-and-play data enrichment platform built for lean GTM teams. In this episode, we unpack how David is building a category-defining product in the shadow of VC-backed behemoths, his playbook for partnerships and product prioritization, and what founders get wrong about GTM data, AI agents, and scraping.

From a rough AppSumo launch to scaling 1,000+ customers with under $500k raised, David brings raw insight and GTM clarity.

Key Discussion Points:

🔥 How a painful personal experience as an investor led to the creation of Databar

📊 The impact of AISDRs on a data business

📈 The role of email in GTM

🚀 The difference between launching on ProductHunt and AppSumo

Timecodes:

0:00 - Introduction

1:00 - David's Journey from Investor to Founder

2:30 - Identifying the Gap in Data Tools

4:00 - The Evolution of DataBar's Product Focus

5:30 - Finding the Right Ideal Customer Profile (ICP)

6:45 - Competing with Clay: Market Positioning

8:15 - Differentiation Strategies Between DataBar and Competitors

9:50 - The Impact of AI SDRs on DataBar's Business

11:30 - The Importance of High-Quality Data in Outreach

13:00 - Multi-Channel Strategies for Customer Engagement

14:20 - Launching on Product Hunt vs. AppSumo

17:00 - Key Differences Between Product Hunt and AppSumo Audiences

18:30 - Recommendations for Launch Timing and Strategy

20:00 - Book Recommendations for Founders

20:30 - Tools and Workflows: What Needs Improvement

21:00 - Nurturing Cold Leads: Strategies for Follow-Up

22:30 - The Role of LinkedIn in Lead Engagement

23:00 - Closing Thoughts and Where to Find DataBar

24:30 - Final Advice for Founders and Entrepreneurs

Important Links:

You can reach David Abaev at https://www.linkedin.com/in/davidabaev1/

Vishesh, your host at https://vishesh.space

Checkout Databar at https://databar.ai

P.S. If you are writing on LinkedIn https://tryjerry.com

I'm joined by Bradley Jones, the Founder & CEO of ThatRound, a pioneering investment platform in the UK. With a background in mathematics and experience in the financial sector, Bradley has a unique understanding of the challenges and opportunities in early-stage investments. In this conversation, we explore how ThatRound is disrupting traditional early-stage investments in the UK, the looming AI Bubble, early-stage investing in general, and more!Key Discussion Points:🔥 What sets the ThatRound model apart from traditional early-stage investments?💸 What are the key factors that contribute to a startup's success in securing funding?📈 How can entrepreneurs balance risk and reward when making investment decisions?Timecodes:0:00 - Introduction2:15 - Background on the Podcast and Host4:30 - The Journey of Building a Network in Entrepreneurship7:00 - Transitioning from Startup to Podcasting9:45 - Insights on Funding and Investment Strategies12:30 - The Importance of Networking in Silicon Valley15:00 - Discussion on Deep Tech and Innovative Startups18:15 - Challenges in Raising Capital for Startups21:00 - Overview of the New Business: That Round24:30 - The Problem with Current Funding Processes27:00 - How That Round Streamlines Capital Access30:00 - Business Model: Startups vs. Investors33:15 - Due Diligence and Quality Control in Startups36:00 - Addressing the Needs of Investors and Founders39:00 - The Future of Funding and Investment Trends42:15 - The Next Wave45:00 - The Investor Pain53:00 Cracking the startup investor marketplace58:00 Wrap up and promo codeImportant Links:You can reach Bradley Jones at https://www.linkedin.com/in/bradley-jones-founderCheck out ThatRound at https://www.thatround.com/Vishesh, your host at https://vishesh.spaceP.S. If you are struggling with writing on LinkedIn, https://tryjerry.com

Episode 51 with Santosh Sharan, Co-Founder & CEO at ZeerAI.I'm joined by Santosh Sharan, Co-Founder & CEO of ZeerAI, a pioneer in AI-driven go-to-market strategies. With a background in engineering and a passion for innovation, Santosh has led ZeerAI from its early days to a successful SaaS company. In this conversation, we dive deep into the challenges of building a successful SaaS business, discuss the impact of AI on go-to-market strategies, and explore practical strategies for SaaS founders navigating the changing landscape.In this episode, we explore the future of SaaS and the impact of AI on business models, customer acquisition costs, and the sales process. We discuss the importance of smart automation, unique data strategies, and community building to create a competitive moat.Key Discussion Points:🔥 Why most SaaS founders get AI implementation completely wrong🤖 The surprising way AI is changing the sales process📈 How to create a competitive moat in the SaaS landscape💡 The importance of unique data strategies in SaaS business models👥 How community building can drive customer acquisition and retention🚀 The future of SaaS and the impact of AI on customer acquisition costs💻 Why traditional CRM systems are no longer effective in the AI eraTimecodes:0:00 - Introduction1:00 - Santosh's Journey from Engineer to Founder3:15 - The Importance of Staying in One Industry5:00 - Learning Curve and Career Optimization7:30 - Overview of Zeer and Its Mission9:45 - The Shift in Go-To-Market Strategies12:00 - Challenges in Building a Two-Sided Marketplace14:30 - The Evolution of Product Development with AI17:00 - Impact of AI on Customer Acquisition Costs20:00 - The Future of SaaS: Legacy vs. New Players22:30 - Organizational Changes in the Age of AI25:00 - Hiring Strategies for AI-Driven Companies28:15 - The Role of Junior Employees in the Future Workforce30:45 - Learning Beyond the Job: A New Mindset33:00 - Go-To-Market Strategies: PLG vs. Sales-Led38:00 - Understanding Buyer Needs in Sales40:30 - The Role of Content in Buyer Engagement41:30 - Inspirational Reads and Philosophy42:30 - Closing Remarks and How to Connect with SantoshImportant Links:You can reach Santosh Sharan at https://www.linkedin.com/in/ssharanVishesh, your host at https://vishesh.spaceCheckout ZeerAI at https://zeer.aiP.S. If you are writing on LinkedIn https://tryjerry.com🎙️ Subscribe for more episodes!#Episode51 #VenturingWithVishesh #Startups #Entrepreneurship #startups #entrepreneurship #venturingwithvishesh