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
In this insightful episode, we sit down with Shyam Rao, the founder and CEO of Punchh, for a deep dive into the world of startups and entrepreneurship. Shyam shares his wealth of experience, from bootstrapping Punchh in its early days to scaling it into a successful venture.
13:33 Finding Your First Customers
17:27 Bootstrapping and Early Growth Reflecting on Punchh's journey
27:07 Product-Led Approach
33:39 Focusing on ROI In the early days
35:11 Aligning with Customer Goals
44:09 Building a Strong Company Culture
50:10 Thoughtful Hiring as You Grow
53:39 Fostering Team Spirit
56:25 Preparing for M&A
01:02:52 Maintaining Work-Life Balance
We talk to Sumit Agarwal the founder of Ario and Shape Security (acq by F5 for $1B). We decrypt the the journey from the military to building a deep cybersecurity product and now a personal AI assistant. Listen in to uncover his 3D framework that guided the journey of Shape and now Ario. We wrap with how to navigate M&A, a theme which we believe is going to be a key topic in several board meetings this and next year.
3:13 - Sumit's Journey from Air Force to Security to AI
10:07 - Identifying Hard, Valuable, Fun Opportunities
19:24 - Building 3D defensible, differentiated, delightful tech in tough markets
28:33 - Identifying the right talent
37:38 - How to be Customer Focused NOT Revenue Focused
46:02 - Unlocking Value to Drive Price
55:07 - Solving the demand bottleneck in M&A
58:26 - Decompressing with family
In this episode, we talk to Cedric Bru, the CEO of Taulia. Cedric joined the company after spending 7 years as an exec at Visa. In this episode, we dive deeply into how Cedric put his imprint on the business and navigated a crisis with one of their partners going bankrupt.
1:29 - Cedric’s journey into entrepreneurship and going from big company to startup
18:39 - Embracing the possibility of failure when running a startup
23:40 - Developing a high performance culture
35:28 - Putting your imprint on the business as a new leader
46:15 - Navigating the Greensill Crisis
53:10 - Work life balance
1:03:34 - Advice to start companies in a challenging macro
In this episode we have a great conversation with Varun Badhwar. Varun sold his first company, Redlock, to Palo Alto for over $200M. He recently embarked on his 2nd journey to build Endor Labs, where he raised a $70M Series A to secure the software supply chain.
In this episode we cover:
1:04 - Varun’s foray into startups
8:57 - Hiring and building the best when $s are constrained
17:33 - Positioning for success in a noisy market
32:02 - Early GTM Success in an expensive environment
41:08 - Navigating the Palo Alto Acquisition
50:06 - Spotlight on Endor Labs
58:50 - Decompress
1:12 - Story at Microsoft
9:54 - Dealing with ups and downs
14:30 - Bob’s new book “The Datapreneurs: The Promise of AI and the Creators Building Our Future”
17:55 - Culture through scaling
24:26 - What do you look for when hiring
35:20 - Strategies to compete in the modern landscape
50:42 - Threading the needle
In this episode we cover Mahe's journey to being a founder, how Phenom found it's niche and what makes them successful as a business
1:12 - Mahe’s journey
8:01 - AI’s role in business
20:09 - How do you find a wedge in today’s software saturated world?
29:38 - Building/hiring for a sustainable organization
45:32 - Scaling a business
Join us for this fantastic conversation with Amr Awadallah, the founder of Cloudera and Vectara. We covered a wide range of topics on company building and lessons learned during a long, successful career.
00:45- Amr’s journey to the Valley and breaking in as an immigrant
6:22- Embarking on the Entrepreneurial Journey and Building a Lasting Business
23:30- The art of blending simplicity with technical depth in product
25:05- Balancing culture and talent
31:20- Spotlight on Vector
38:05- Signs of PMF, When to Speed Up and How to Sustain Growth at Scale
42:15- Decompress and Accomplishing your Mission
In this episode we cover:
00:56- Glen's journey to entrepreneurship + healthcare and the learnings along the way
15:19- Getting timing right in healthcare
21:04- Building great culture in tough times
26:40- Hiring the best leaders and putting together an exceptional board
30:11- Advice on scaling at different stages of the business
36:00- Accomplishing his life's mission and staying mentally energized through the journey
On this episode, we go through Andrew's journey through 2 startups and dive into some very interesting lessons learned along the way.
1:20- Andrew's background and journey
4:19- Why Jellyfish and why now? + The market opportunity
15:08- Selecting design partners + Learning from the "No's"
20:36- Tying Vision and Culture
24:58- Andrew's Leadership style + Hiring the right people
32:20- What kept Andrew up at night post-PMF
34:31- Decompressing + Staying mentally fit through the journey
Dheeraj Pandey was the Founder, CEO & Chairman of Nutanix. Nutanix was the fastest company to achieven US$1B ARR scale and the biggest IPO in 2016. He is now working on his next company DevRev. Prior to founding Nutanix, Dheeraj was the VP of Engineering at Aster Data (acquired by Teradata), where he helped build the product and its engineering team from the ground up.
In This Epsiode with Dheeraj, We Discuss: