Imagine if your biggest growth bottleneck wasn’t product, talent, or capital, but the sheer chaos of modern go-to-market. Too many tools. Too many channels. Too much guesswork. Now imagine handing that mess to an AI agent that actually knows what it’s doing.

That’s the bet Harsha Vankayalapati is making. Former Microsoft engineer, two-time YC founder, and now co-founder and CEO of AgentWeb, Harsha is building autonomous AI agents that run go-to-market execution for B2B startups, from content and SEO to paid ads and outbound. His contrarian belief, sharpened by hard startup scars, is simple, GTM execution, not ideas, is what kills most companies, and AI is finally good enough to fix it.

In this episode, we unpack what happens when founders stop duct-taping together CRMs, agencies, and automation tools, and instead let agents do the heavy lifting.

In Today's Episode We Discuss:

00:01 – Introduction to Harsha Vankayalapati & AgentWeb

02:00 – Origin Story: From India to Microsoft

04:20 – Getting into Y Combinator & First Startup Pivot

08:50 – Why Go-To-Market Is the Real Bottleneck

11:50 – The Idea Behind AgentWeb

14:00 – Product vs Distribution in B2B

16:10 – Pretotyping & Validating Demand with Paid Ads

18:20 – The Core Pain AgentWeb Solves

21:15 – Why Now: AI, CAC, and the Attention Economy

24:50 – What AgentWeb Has Solved (and What’s Still Hard)

27:50 – Autonomous GTM vs Traditional Marketing Automation

31:40 – Human Taste vs AI Execution

34:20 – Reliability Challenges with AI Agents

38:40 – Benchmarks vs Real-World AI Performance

40:50 – Ideal Customer Profile for AgentWeb

43:30 – Early Traction & Signs of Product-Market Fit

45:10 – Onboarding, Pricing & Managed Service Model

49:50 – The Future of Agentic Go-To-Market

52:50 – Rapid Fire: Strong Opinions & Hard Decisions

56:00 – Long-Term Vision & Closing Thoughts

Harsha’s journey, from building enterprise workflows at Microsoft to watching his own startups stall on distribution, leads to a sharp conclusion, the future isn’t just vibe coding products, it’s vibe growing companies.

Pull quotes:

“Go-to-market isn’t an idea problem, it’s an execution problem.”

“If we don’t fix how products reach people, mediocre products with great marketing will win.”

From newsletters to neural nets, this conversation connects Harsha’s past building systems at massive scale to a future where founders might never need an agency again, just the right agent.

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What if the biggest tech opportunities aren’t the ones that make billions, but the ones that actually work?

Jim Fruchterman has spent three decades proving a quiet, uncomfortable truth, some of the most leverage-rich technology in the world will never be VC-backable, and that’s exactly why it matters.

Jim is a Caltech-trained engineer, serial founder, and MacArthur Fellow who walked away from traditional Silicon Valley success to build something stranger and more ambitious. First at Benetech, and now as the founder of Tech Matters, he’s been building open-source, revenue-generating software for the 90 percent of humanity most tech companies ignore. Crisis helplines, disability access, human rights, mental health infrastructure, all powered by product-first thinking and disciplined business models that just happen to be nonprofit.

In this episode, we unpack what happens when you apply Silicon Valley rigor to markets everyone else calls “too small” or “not scalable.”

In Today's Episode We Discuss:

00:01 — Jim Fruchterman’s Origin Story

01:05 — From Caltech to Silicon Valley Startups

02:10 — Early AI, OCR, and Reading for the Blind

03:00 — When VCs Say No to Social Impact

03:45 — The Accidental Nonprofit Insight

04:45 — Seven Startups and Choosing the Nonprofit Path

06:00 — The Market Failure Between Tech and Profit

07:10 — Applying Silicon Valley Rigor to Social Good

08:20 — Venture-Style Filtering for Nonprofit Ideas

09:30 — Distribution as the Real Bottleneck

10:30 — Introducing Tech Matters

11:15 — Nonprofit Vertical SaaS Explained

12:00 — Crisis Helplines and Cloud Infrastructure

13:30 — Competing with Salesforce in Niche Markets

15:00 — Revenue, Subsidies, and Sustainability

16:30 — Donors as Early Risk Capital

18:00 — When Nonprofits Become For-Profits

19:30 — Selling a Nonprofit and Market Creation

21:00 — Measuring Impact Beyond Vanity Metrics

22:30 — Open Source for Trust and Resilience

24:00 — What Tech Matters Is Building Next

25:30 — Mental Health Infrastructure at Scale

27:00 — AI Hype vs Real Productivity Gains

29:00 — Automating Drudgery, Not Empathy

31:00 — Technology, Ethics, and Design Intent

33:00 — Regulating Tech When It Goes Too Far

35:00 — Optimism About AI and Human Adaptation

37:00 — The Long-Term Role of Tech for Good

39:00 — Legacy and the Future of Social Impact Tech

Jim has founded companies where only five out of seven failed, sold a nonprofit to private equity, beaten Salesforce head-to-head in a vertical SaaS niche no one wanted, and helped define an entirely new playbook for impact-driven technology.

He didn’t reject Silicon Valley logic. He just took it somewhere it was never designed to go.

Pull quotes:

“A two or three million dollar nonprofit that breaks even is a screaming success, not a failure.”

“If your idea doesn’t pencil out, Silicon Valley calls it bad. I call it an opportunity.”

This episode is a reminder that innovation doesn’t disappear when the profit motive breaks down. It just changes shape, and sometimes, it gets more interesting.

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What if the biggest risk in the AI era isn’t machines replacing people, but people refusing to reinvent themselves?

Nikki Barua has spent her life doing the opposite. A serial entrepreneur, bestselling author, and one of the most influential voices on reinvention, Nikki has spent decades helping organizations and leaders adapt to change. Today, she’s the founder and CEO of Flipwork, a company rethinking how work actually gets done in the age of AI, not by adding more tools, but by upgrading how humans think, decide, and create value.

In this episode, Nikki and Brian go deep on what breaks when industrial-age mindsets collide with exponential technology, and why most AI transformations fail before they even start. This is a conversation about founder mindset at enterprise scale, the psychology of reinvention, and why adaptability, not intelligence or effort, is the real competitive moat now.

In Today's Episode We Discuss:

00:01 Welcome and Nikki Barua Introduction

02:00 Reinvention as a Life Pattern

04:10 Immigrant Mindset and Resilience

06:20 Video Games, Mastery, and Growth

08:40 Enjoying the Grind

10:30 Boredom as a Signal for Change

12:00 Corporate Inertia and Slow Innovation

14:20 From Enterprise to Entrepreneurship

16:30 Building Flipwork

18:10 AI Is Not an IT Problem

20:00 Human and Machine Co-Evolution

22:10 From Task Doers to Outcome Orchestrators

24:30 Identity Crisis at Work

27:00 Middle Management Gets Squeezed

29:30 Enterprise AI Blind Spots

32:00 Adaptability as the New Moat

35:00 The Industrial Age Is Over

38:00 Neural Network Organizations

41:20 Reinvention as a Muscle

43:40 The End of Full-Time Jobs

This episode keeps circling back to one idea, the future belongs to those willing to unlearn fast. Nikki’s journey, from growing up in India to building companies in the US, mirrors the very reinvention she’s now helping others navigate.

As she puts it, “The most powerful technology on earth is still the human being.” The catch is, only if we’re willing to evolve.

Subscribe on Spotify: https://open.spotify.com/show/6Ga6v0YUsHotLhjap67uu5

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