

UNPAK3D Podcast
UNPAK3D Pod
A podcast for operators by operators
UNPAK3D Podcast stands for unpacking these journeys by Decrypting, Decoupling, and Decompressing. We Decrypt concepts like "hiring great people", "finding product-market fit"; we Decouple the outcomes of businesses from the ebbs and flows of the journey; we Decompress by learning how these operators take a step back from their business.
UNPAK3D Podcast stands for unpacking these journeys by Decrypting, Decoupling, and Decompressing. We Decrypt concepts like "hiring great people", "finding product-market fit"; we Decouple the outcomes of businesses from the ebbs and flows of the journey; we Decompress by learning how these operators take a step back from their business.
Episodes
Mentioned books

Mar 19, 2026 • 1h 3min
Ep. 24: From $3.7B Exit to $5.5B Company: What Jyoti Bansal Actually Learned the Second Time
Jyoti Bansal was days away from taking AppDynamics public when Cisco made a $3.7 billion offer that changed everything. Now his second company, Harness, is valued at $5.5B — and he's built it on a contrarian thesis: AI is producing more code than ever, but code isn't the finished product. We cover the real story behind the Cisco acquisition, why his best sales reps from AppDynamics failed in the early days of Harness, how he runs 16 product modules as "startups within a startup," and why 70% of engineering time still happens after the code is written.This episode is brought to you by Stifel Bank.Timestamps(0:00) Trailer(0:52) Introduction and welcome(2:36) Jyoti's journey from small-town India to Silicon Valley(6:01) Three lessons from AppDynamics that shaped Harness(10:29) Proving value — not just finding the problem(17:23) The sales hiring mistake: matching reps to your stage(27:42) 72 hours from IPO to Cisco's $3.7B acquisition(33:57) Startups within a startup — Harness's M&A playbook(39:06) AI's productivity paradox: more code, less throughput(48:44) The "two AIs" framework and where moats really live(58:50) How Jyoti decompresses

Feb 12, 2026 • 60min
Ep 23: The Anti-Vibe AI Revolution, Scott Dietzen of Augment Code
Is "vibe coding" enough for the enterprise? Scott Dietzen explains why professional engineers need an expert AI, not a toy.In this episode, we sit down with Scott Dietzen, Former CEO of Augment Code and Former CEO of Pure Storage. Scott breaks down why the current "vibe coding" trend—where non-engineers generate simple apps from scratch—fails to address the needs of large-scale enterprise software.Key Topics Discussed:The Context Engine Moat: Why passing 20 million lines of code into a context window doesn't work, and how Augment solves this with a real-time semantic map.Agentic AI: Moving beyond simple chat to AI agents that can handle parallel tasks like testing and code reviews.Security First: How Augment secured SOC 2 and ISO certifications to win enterprise trust where competitors failed.Leadership & Hiring: Scott's framework for building high-trust teams and why he never had to ask for a raise in his career.Timestamps(00:00) Intro (02:52) Augment: The Anti-Vibe Coding (05:39) From Chat to AI Agents (11:04) The Problem with Fine-Tuning (13:05) Building a Context Engine (23:23) Security as a Moat (29:40) Hiring for Trust (43:30) PLG vs. Enterprise Sales (54:37) The Myth of the Solo Founder (57:19) Leadership & Burnout

28 snips
Jan 22, 2026 • 1h 2min
Ep 22: Building Category-Defining AI Companies with Gokul Rajaram
Gokul Rajaram, seasoned operator and investor who led product at Google, Facebook, Square and DoorDash, explains where AI is actually winning. He highlights document processing, browser automation and voice agents as the biggest unlocks. He warns against infrastructure and middleware bets. He urges startups to build a second product fast and focus on retention metrics over top-line growth.

Dec 18, 2025 • 1h 10min
Ep. 21: Disrupting the Custodial Duopoly and Building the "Robinhood for Advisors w/ Jason Wenk CEO @ Altruist
In this episode, we sit down with Jason Wenk, Founder and CEO of Altruist. Jason shares the "lightbulb moment" he had watching Robinhood take off, realizing that Registered Investment Advisors (RIAs) were stuck using archaic, disjointed technology while consumers were getting sleek, digital experiences.We unpack how Altruist is taking on the industry giants (the "Duopoly") through vertical integration and why Jason believes legacy custodians have zero incentive to innovate. We also dive deep into the controversial side of company building: the return of "hardcore" work culture, hiring for intensity, and why Jason believes the era of soft startups is over.(00:00) Intro & The Origin Story: From starting at Morgan Stanley at 19 to the serial entrepreneur journey that led to founding Altruist.(18:18) Disruption Thesis: The "Robinhood Moment" & Vertical Integration: How seeing the mobile trading revolution inspired Jason to rebuild the custodial stack, and why the "Duopoly" incumbents (Schwab/Fidelity) struggle to innovate due to high margins and inertia.(39:22) The Playbook: Scaling to Billions: Altruist’s Go-to-Market strategy: How they gained initial traction by targeting the "hungry and underserved" small advisors that the giants ignored, and eventually moved upmarket.(42:20) The AI Future: "Hazel" and The Bionic Advisor: Why Altruist is pivoting hard into AI agents, how "Hazel" renders traditional CRMs obsolete, and Jason's prediction on when AI will replace human financial advice (featuring the $15k fence story).(57:03) Founder Mode: Culture, Intensity & Performance: A deep dive into building a "hardcore" culture, the return of the "996" mindset, and Jason's personal routine (including the gene mutation that lets him thrive on 4.5 hours of sleep).

Nov 26, 2025 • 1h
Ep. 20: From Hype to Production: Inside Writer’s Playbook for Deploying Enterprise AI w/ Waseem Alshikh, CTO @ Writer
Waseem Alshikh, Co-founder and CTO of Writer, shares insights on deploying generative AI in enterprises. He discusses the importance of predictability and domain-specific models over general hype, emphasizing their role in regulated industries. Waseem reveals how Writer's full-stack approach ensures security and performance. He presents a contrarian view on 'small' models and highlights the need for effective change management to achieve real ROI. He also introduces the concept of 'Artificial Governance Intelligence' and the rising trend of multimodality in AI interactions.

Oct 30, 2025 • 1h 12min
Ep 19: Community Is the New Moat: Stack Overflow’s Second Act with Prashanth Chandrasekar
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 GoogleWhat it takes to lead a “people transformation” during industry disruptionThe future of developer communities and the rise of agentic AI in the enterpriseWhy he believes community is more important than ever in the AI ageA must-listen for anyone building in AI, developer tools, or enterprise SaaS.00:00 – Intro and Prashanth’s journey from Rackspace to Stack Overflow05:30 – Rebuilding the team: leading a people and culture transformation10:40 – How Stack Overflow built its enterprise SaaS motion18:00 – The pivot from community and ads to enterprise and recurring revenue27:00 – Lessons from leading through change: hiring slow, acting fast27:30 – The OpenAI partnership and data licensing strategy33:00 – Stack Overflow’s role in the AI tech stack41:00 – How enterprises like Uber are building internal copilots using Stack Overflow data45:00 – The economics of high-quality data and premium licensing49:00 – The agentic AI opportunity in the enterprise54:00 – How AI is changing software development and product velocity1:00:00 – Why community will matter even more in the age of AI

Sep 18, 2025 • 1h 1min
Ep. 18: AI for the CFO — Numeric’s Playbook with Parker Gilbert, CEO of Numeric
Parker Gilbert, CEO of Numeric, delves into the transformative power of AI in finance, specifically tailored for CFOs and their teams. He shares insights on how Numeric addresses the challenges of financial data accuracy and reliability. Parker emphasizes the importance of balancing automation with auditability and discusses his journey from strategy to founding Numeric. Expect revelations about acquiring early customers, pricing strategies, and enhancing forecasting processes, all while envisioning a future driven by AI in finance.

Aug 14, 2025 • 1h 5min
Ep. 17: Why the Smartest Companies Will Fire SaaS and Hire AI with Surojit Chatterjee from Ema AI
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

Jun 26, 2025 • 1h 1min
Ep. 16 Security for the Cloud + AI Era: A Conversation with Sanjay Beri, CEO of Netskope
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 shiftWhy balancing strategic foresight with day-to-day customer interaction is core to Sanjay’s leadership styleHow Netskope hires for culture over pedigree, and why empathy and openness are part of formal performance reviewsThe company’s product strategy, GTM evolution, and approach to navigating AI securityLessons from scaling during the pandemic and how to train a team for high-growth executionAnd—how Sanjay personally decompresses after building a global enterprise platformThis conversation is full of practical insights for founders, operators, and anyone building in the enterprise space.Episode Timestamps:00:00 – Intro00:53 – The Journey to Netskope06:06 – “Living in the clouds and in the trenches” — explained07:53 – Hiring philosophy: culture vs credentials14:51 – Ensuring employees align with the company’s vision20:21 – Building Platforms vs Products32:43 – Changing processes to enable scale41:52 – Toughest parts of scale and standing out in tough markets52:07 – The rise of AI and “shadow AI” in the enterprise58:40 – Decompress with Sanjay: Personal strategies for relaxation and focus

May 29, 2025 • 60min
Ep. 15: Decoding AI Trust- A Conversation with Galileo AI's Atin Sanyal
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 Galileo3:49 - What does Galileo do?11:17 - AI as a Judge and How Galileo Works14:45- Generalizing AI Evals24:44 - Defining an ICP in the AI World27:56 - Ideal Customer Profile33:35 - Open Source vs. Closed Source42:05 - Building AI Eng Teams and Leveraging AI Tools to Scale52:00 - State of AI in the Enterprise57:21 - Decompress


