UNPACK3D Podcast

In this episode of UNPAK3D, we sit down with Waseem Alshikh, co-founder and CTO of Writer, to unpack the reality of deploying Generative AI in the enterprise. While the consumer market chases the latest AGI hype, Waseem explains why the enterprise roadmap requires a different approach: predictability, domain specificity, and a shift from simple content generation to executing complex actions.

We dive deep into Writer's "full-stack" strategy—owning the LLM family (Palmera), the graph-based context layer, and the application layer—and why this architecture is critical for security and accuracy in regulated industries like healthcare and finance. Waseem also shares his contrarian take on "small" models, the necessity of change management to unlock real ROI, and why he defines AGI not as General Intelligence, but as "Artificial Governance Intelligence".

00:15 — Introductions & Writer’s core mission
03:25 — The enterprise AI gap: predictability vs. hype
07:40 — Domain-specific models and why they outperform general models
12:55 — Synthetic data, grounding, and how Writer trains models
18:10 — Building the enterprise context layer (knowledge graphs)
22:45 — On-prem, small models & deployment realities
28:15 — How enterprises are shifting their AI buying behavior
33:30 — Competing with OpenAI & managing roadmap pressure
39:35 — Multimodality and why it’s emerging inside the enterprise
45:25 — Unit economics, ROI & end-to-end task automation
51:15 — Competing for talent + Waseem’s view on AGI
55:55 — Decompression, customer stories & closing thoughts

Stack Overflow has been the home for developers for over a decade — but the rise of AI is changing everything. In this episode, we talk to Prashanth Chandrasekhar, CEO of Stack Overflow, about how he’s reinventing the company from an ad-based community platform to an enterprise SaaS and data licensing business at the center of the AI ecosystem.

We discuss:

• How Stack Overflow’s data powers models from OpenAI and Google

• What it takes to lead a “people transformation” during industry disruption

• The future of developer communities and the rise of agentic AI in the enterprise

• Why he believes community is more important than ever in the AI age

A must-listen for anyone building in AI, developer tools, or enterprise SaaS.

00:00 – Intro and Prashanth’s journey from Rackspace to Stack Overflow
05:30 – Rebuilding the team: leading a people and culture transformation
10:40 – How Stack Overflow built its enterprise SaaS motion
18:00 – The pivot from community and ads to enterprise and recurring revenue
27:00 – Lessons from leading through change: hiring slow, acting fast
27:30 – The OpenAI partnership and data licensing strategy
33:00 – Stack Overflow’s role in the AI tech stack
41:00 – How enterprises like Uber are building internal copilots using Stack Overflow data
45:00 – The economics of high-quality data and premium licensing
49:00 – The agentic AI opportunity in the enterprise
54:00 – How AI is changing software development and product velocity
1:00:00 – Why community will matter even more in the age of AI

Parker Gilbert, founder & CEO of Numeric, joins the UNPAK3D podcast to walk through why finance teams are finally ready for AI-driven modeling, how Numeric approaches the hardest part (financial data and reliability), and the practical GTM playbook for selling to CFOs.

Parker explains his path from strategy and scaling early-stage companies to starting Numeric, the “aha” problem Numeric solves for the office of the CFO, and how the product balances automation with auditability. We dig into data quality, model scaffolding, customer feedback loops, pricing and go-to-market lessons, and the fundraising choices that shaped Numeric’s early growth. If you’re a founder or CEO wrestling with forecasting, finance headcount, or how to productize ML for accounting teams, this episode offers concrete takeaways and real-world tradeoffs to consider.

00:00 — Intro & Parker’s background
05:55 — Founding Numeric — the problem and the “aha”
09:46 — Product demo & early customers (initial signals)
14:10 — Data quality, modeling limits & reliability
45:34 — Go-to-market, customers, pricing & metrics
55:09 — Why now — vision, risks, and next steps

From $50B mobile ads at Google to taking Coinbase public, Surojit Chatterjee has spotted — and seized — every major tech inflection point. Now, as CEO of Ema, he’s betting on “AI employees” to transform how enterprises work.

In this episode: spotting trillion-dollar trends, building AI that works across industries, and why the future belongs to first-principles thinkers.

• (0:16) Surojit’s journey: Google, Flipkart, Coinbase, and the leap to Ema

• (7:20) The “AI employee” vision — and why no one got it at first

• (14:07) Spotting tech inflection points: lessons from mobile, crypto, and AI

• (17:15) Horizontal vs. vertical AI: the case for building broad and deep

• (27:33) Hiring in the agentic AI era: first-principles thinkers over resumes

• (34:44) Running lean: using AI instead of humans where possible

• (39:08) Why legacy SaaS struggles to adapt to AI

• (42:59) Overcoming employee fear and resistance to AI adoption

• (50:03) The pitch to executives: freeing people from “soul-crushing” work

• (52:57) Is 2025 still the year of AI experimentation?

• (55:09) Avoiding plateaus: chaining AI employees for exponential impact

• (1:00:19) The adoption curve: innovators, fast followers, and scaling

• (1:01:19) Decompression and founder mindset: meditation, family, and doing nothing

In this episode, we sit down with Sanjay Beri, founder and CEO of Netskope, to explore how he built one of the most innovative cybersecurity companies of our time—now generating $500M+ in revenue and protecting over one-third of the Fortune 100.

We dive deep into:

• The vision behind Netskope and its role in a multi-hundred billion dollar market shift

• Why balancing strategic foresight with day-to-day customer interaction is core to Sanjay’s leadership style

• How Netskope hires for culture over pedigree, and why empathy and openness are part of formal performance reviews

• The company’s product strategy, GTM evolution, and approach to navigating AI security

• Lessons from scaling during the pandemic and how to train a team for high-growth execution

• And—how Sanjay personally decompresses after building a global enterprise platform

This conversation is full of practical insights for founders, operators, and anyone building in the enterprise space.

Episode Timestamps:

00:00 – Intro
00:53 – The Journey to Netskope
06:06 – “Living in the clouds and in the trenches” — explained
07:53 – Hiring philosophy: culture vs credentials
14:51 – Ensuring employees align with the company’s vision
20:21 – Building Platforms vs Products
32:43 – Changing processes to enable scale
41:52 – Toughest parts of scale and standing out in tough markets
52:07 – The rise of AI and “shadow AI” in the enterprise
58:40 – Decompress with Sanjay: Personal strategies for relaxation and focus

In this episode we had a fantastic time talking to Atin Sanyal the CTO of Galileo. Galileo is a fast-growing GenAI Evaluation platform, which ensures AI apps perform reliably. In this episode we cover a lot of ground from Atin's read on the state of AI in the enterprise to how you deploy it reliably. Please listen, like and subscribe!

1:08 - Atin’s journey to Galileo
3:49 - What does Galileo do?
11:17 - AI as a Judge and How Galileo Works
14:45- Generalizing AI Evals
24:44 - Defining an ICP in the AI World
27:56 - Ideal Customer Profile
33:35 - Open Source vs. Closed Source
42:05 - Building AI Eng Teams and Leveraging AI Tools to Scale
52:00 - State of AI in the Enterprise
57:21 - Decompress

A power-packed Unpak3d Podcast featuring Mike Conover, CEO of Brightwave, sharing battle-tested strategies for enterprise AI success. Mike breaks down exactly how to build, scale, and dominate in the AI-first era.

Since recording this episode, Brightwave has launched Report Builder and Blueprints, two powerful new features that mark the debut of the first deep research platform purpose-built for private market investors. These tools help investment teams go from a 1,000-page data room to a fully sourced, sharable report in minutes—automating workflows like investment memos, expert call summaries, and comp analyses.

Key insights you'll discover:

🚀 1:31 - From Zero to AI Hero: Mike's journey and critical success factors

🤝 6:20 - Building Your AI Dream Team: Culture secrets that attract and retain top talent

🔓 14:13 - The Open Source Advantage: Why it matters for enterprise adoption

🛠️ 21:35 - Production-Ready AI: Skip the common pitfalls, nail the execution

🏄‍♂️ 27:48 - Surfing the AI Wave: Strategic moves that put you ahead of competition

🛡️ 38:30 - Data Moat Strategy: Transform data into unbeatable market advantage

✨ 42:19 - The Brightwave Edge: Inside look at next-gen AI implementation

🤝 50:57 - Strategic Partnerships: Accelerate growth through smart collaborations

🧘 59:42 - Leadership Sustainability: Balance innovation with personal well-being

We had a fantastic conversation with Jake Heller who founded Casetext and sold the company to Thomson Reuters for $650M. We cover the Casetext journey to AI, how he positioned himself to take advantage of the AI wave and his lessons on creating a buzz for M&A. Listen, like and subscribe!

1:00 - The Casetext journey

5:00 - Learning to leverage AI

21:00 - Moats in Vertical AI

29:00 - Thoughts on Building an AI-native startup

32:57 - Defining Customer Obsession and finding PMF

55:23 - Lessons on hiring and the importance of culture

1:04:31 - Decompressing

We had a great conversation with George on his career lessons, coaching his founders to be great, how AI is shifting business models and where he sees the opportunity emerging

Please listen, like and subscribe!

1:42 - George's Journey
10:36 - Lessons and Resilience born from Failure
26:59 - Coaching Well-Rounded Founders
33:56 - Remember the Fundamentals when Building AI
40:22 - Changing business models to fit AI
52:43 - Where do startups win in a noisy world?
1:03:36 - Decompress

In this episode, we have a fantastic conversation with Ankit Jain, CEO of Infinitus. We cover a broad range of topics around selling, delivering value and building with a focus on how Infinitus has been successful in healthcare. We then talk about how AI going to be impact healthcare and how it will get adopted. Please listen and subscribe!

1:27 - Ankit's Journey to Infinitus

14:01 - Taking the entrepreneurial plunge

19:50 - Choosing and building the Services as a Software approach

30:58 - Spotlight on Infinitus

35:11- Pricing Service as a Software

44:35 - Developing the GTM for Healthcare

53:31 - Opportunities for AI in Healthcare

58:15 - Decompress