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The Effortless Podcast

The Effortless Podcast

De: Dheeraj Pandey Amit Prakash
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Join longtime friends and entrepreneurs Dheeraj Pandey, founder of DevRev, and Amit Prakash, co-founder of ThoughtSpot, on The Effortless Podcast as they explore the art of building, innovating, and thriving in tech—without losing sight of what really matters. With decades of experience scaling companies and navigating risk, Dheeraj and Amit tackle tough questions for modern entrepreneurs: How can startups feel effortless in the face of endless challenges? What does “long-term greedy” mean when aligning personal growth with team success? Whether you're a seasoned founder, a new entrepreneur, or just curious, The Effortless Podcast offers something for everyone in the journey of building with purpose. Economía Gestión y Liderazgo Liderazgo
Episodios
  • Alex Dimakis: The Future of Long-Horizon AI Agents - Episode 21: The Effortless Podcast

    Alex Dimakis: The Future of Long-Horizon AI Agents - Episode 21: The Effortless Podcast
    Jan 6 2026
    In this episode of The Effortless Podcast, Amit Prakash and Dheeraj Pandey are joined by Alex Dimakis for a wide-ranging, systems-first discussion on the future of long-horizon AI agents that can operate over time, learn from feedback, adapt to users, and function reliably inside real-world environments.The conversation spans research and industry, unpacking why prompt engineering alone collapses at scale; how advisor models, reward-driven learning, and environment-based evaluation enable continual improvement without retraining frontier models; and why memory in AI systems is as much about forgetting as it is about recall. Drawing from distributed systems, reinforcement learning, and cognitive science, the trio explores how personalization, benchmarks, and context engineering are becoming the foundation of AI-native software.Alex, Dheeraj, and Amit also examine the evolution from SFT to RL to JEPA-style world models, the role of harnesses and benchmarks in measuring real progress, and why enterprise AI has moved decisively from research into engineering. The result is a candid, deeply technical conversation about what it will actually take to move beyond demos and build agents that work over long horizons.Key Topics & Timestamps 00:00 – Introduction, context, and holiday catch-up04:00 – Teaching in the age of AI and why cognitive “exercise” still matters08:00 – Industry sentiment: fear, trust, and skepticism around LLMs12:00 – Memory in AI systems: documents, transcripts, and limits of recall17:00 – Why forgetting is a feature, not a bug22:00 – Advisor models and dynamic prompt augmentation27:00 – Data vs metadata: control planes vs data planes in AI systems32:00 – Personalization, rewards, and learning user preferences implicitly37:00 – Why prompt-only workflows break down at scale41:00 – RAG, advice, and moving beyond retrieval-centric systems46:00 – Long-horizon agents and the limits of reflection-based prompting51:00 – Environments, rewards, and agent-centric evaluation56:00 – From Q&A benchmarks to agents that act in the world1:01:00 – Terminal Bench, harnesses, and measuring real agent progress1:06:00 – Frontier labs, open source, and the pace of change1:11:00 – Context engineering as infrastructure (“the train tracks” analogy)1:16:00 – Organizing agents: permissions, visibility, and enterprise structure1:20:00 – SFT vs RL: imitation first, reinforcement last1:25:00 – Anti-fragility, trial-and-error, and unsolved problems in continual learning1:28:00 – Closing reflections on the future of long-horizon AI agentsHosts:Amit PrakashCEO & Founder at AmpUp, Former engineer at Google AdSense and Microsoft Bing, with deep expertise in distributed systems, data platforms, and machine learning.Dheeraj PandeyCo-founder & CEO at DevRev, Former Co-founder & CEO of Nutanix. A systems thinker and product visionary focused on AI, software architecture, and the future of work.Guest:Alex DimakisAlex Dimakis is a Professor in UC Berkeley in the EECS department. He received his Ph.D. from UC Berkeley and the Diploma degree from NTU in Athens, Greece. He has published more than 150 papers and received several awards including the James Massey Award, NSF Career, a Google research award, the UC Berkeley Eli Jury dissertation award, and several best paper awards. He is an IEEE Fellow for contributions to distributed coding and learning. His research interests include Generative AI, Information Theory and Machine Learning. He co-founded Bespoke Labs, a startup focusing on data curation for specialized agents.Follow the Hosts and the Guest: Dheeraj Pandey:LinkedIn - https://www.linkedin.com/in/dpandeyTwitter - https://x.com/dheerajAmit Prakash:LinkedIn - https://www.linkedin.com/in/amit-prak...Twitter - https://x.com/amitp42Alex Dimakis:LinkedIn - https://www.linkedin.com/in/alex-dima...Twitter - https://x.com/AlexGDimakis Share Your Thoughts Have questions, comments, or ideas for future episodes?📩 Email us at EffortlessPodcastHQ@gmail.comDon’t forget to Like, Comment, and Subscribe for more conversations at the intersection of AI, systems, and product design.
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    1 h y 32 m
  • The Structured vs. Unstructured Debate in Business Software - Episode 20: The Effortless Podcast

    The Structured vs. Unstructured Debate in Business Software - Episode 20: The Effortless Podcast
    Dec 15 2025

    In this episode of The Effortless Podcast, Amit Prakash and Dheeraj Pandey dive deep into one of the most important shifts happening in AI today: the convergence of structured and unstructured data, interfaces, and systems.

    Together, they unpack how conversations—not CRM fields—hold the real ground truth; why schemas still matter in an AI-driven world; and how agents can evolve into true managers, coaches, and chiefs of staff for revenue teams. They explore the cognitive science behind visual vs conversational UI, the future of dynamically generated interfaces, and the product depth required to build enduring AI-native software.

    Amit and Dheeraj break down the tension between deterministic and probabilistic systems, the limits of prompt-driven workflows, and why the future of enterprise AI is “both-and” rather than “either-or.” It’s a masterclass in modern product, data design, and the psychology of building intelligent tools.

    Key Topics & Timestamps

    00:00 – Introduction
    02:00 – Why conversations—not CRM fields—hold real ground truth
    05:00 – Reps as labelers and the parallels with AI training pipelines
    08:00 – Business logic vs world models: defining meaning inside enterprises
    11:00 – Prompts flatten nuance; schemas restore structure
    14:00 – SQL schemas as the true model of a business
    17:00 – CRM overload and the friction of rigid data entry
    20:00 – AI agents that debrief and infer fields dynamically
    23:00 – Capturing qualitative signals: champions, pain, intent
    26:00 – Multi-source context: transcripts, email threads, Slack
    29:00 – Why structure is required for math, aggregation, forecasting
    32:00 – Aggregating unstructured data to reveal organizational issues
    35:00 – Labels, classification, and the limits of LLM-only workflows
    38:00 – Deterministic (SQL/Python) vs probabilistic (LLMs) systems
    41:00 – Transitional workflows: humans + AI field entry
    44:00 – Trust issues and the confusion of the early AI market
    47:00 – Avoiding “Clippy moments” in agent design
    50:00 – Latency, voice UX, and expectations for responsiveness
    53:00 – Human-machine interface for SDRs vs senior reps
    56:00 – Structured vs unstructured UI: cognitive science insights
    59:00 – Charts vs paragraphs: parallel vs sequential processing
    1:02:00 – The “Indian thali” dashboard problem and dynamic UI
    1:05:00 – Exploration modes, drill-downs, and empty prompts
    1:08:00 – Dynamic leaves, static trunk: designing hierarchy
    1:11:00 – Both-and thinking: voice + visual, structured + unstructured
    1:14:00 – Why “good enough” AI fails without deep product
    1:17:00 – PLG, SLG, data access, and trust barriers
    1:20:00 – Closing reflections and the future of AI-native software

    Hosts:

    Amit Prakash – CEO and Founder at AmpUp, former engineer at Google AdSense and Microsoft Bing, with extensive expertise in distributed systems and machine learning

    Dheeraj Pandey – Co-founder and CEO at DevRev, former Co-founder & CEO of Nutanix. A tech visionary with a deep interest in AI, systems, and the future of work.


    Follow the Hosts:

    Amit Prakash
    LinkedIn – Amit Prakash I LinkedIn
    Twitter/X – https://x.com/amitp42

    Dheeraj Pandey
    LinkedIn –Dheeraj Pandey | LinkedIn

    Twitter/X – https://x.com/dheeraj

    Share your thoughts :

    Have questions, comments, or ideas for future episodes?
    Email us at EffortlessPodcastHQ@gmail.com

    Don’t forget to Like, Comment, and Subscribe for more conversations at the intersection of AI, technology, and innovation.
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    1 h y 22 m
  • Abhay Parasnis on Betting Big on AI and Building Typeface from Scratch - Episode 19: The Effortless Podcast

    Abhay Parasnis on Betting Big on AI and Building Typeface from Scratch - Episode 19: The Effortless Podcast
    Nov 20 2025

    In this episode of The Effortless Podcast, Amit Prakash sits down with Abhay Parasnis, Founder and CEO of Typeface, to explore how AI is reshaping marketing, creativity, and entrepreneurship.

    Abhay reflects on his incredible journey from building foundational internet technologies at IBM, leading Microsoft’s Azure transformation, driving Adobe’s shift to the cloud, and now launching Typeface to personalize content creation at scale through generative AI.

    He opens up about what it really means to start over after corporate success, the evolving definition of product-market fit in the AI era, and why speed, curiosity, and the beginner’s mind are the most important superpowers today.

    Amit and Abhay discuss the “AI slop” problem, steering powerful models with context, unlearning corporate habits, and how the next generation of AI agents will move from orchestration to closed-loop intelligence.

    Key Topics & Timestamps

    00:00 – Introduction
    01:15 – Abhay’s journey: from IBM & Microsoft to Adobe and Typeface
    05:40 – The beginner’s mind and the art of reinvention
    10:25 – Leaving Adobe to start from scratch
    15:30 – Risk, ego, and the emotional side of entrepreneurship
    21:10 – Redefining product-market fit in an AI-driven world
    27:45 – The “continuous recalibration” mindset for startups
    33:30 – Solving “AI slop” with brand context and personalization
    39:20 – Engineering challenges behind Typeface’s AI platform
    46:00 – Why social engineering is as hard as technical innovation
    51:15 – Lessons from Adobe & Microsoft: what to keep and unlearn
    56:40 – Steering AI systems: the new critical skill
    1:02:05 – Counterintuitive truths about creativity and automation
    1:07:10 – Democratized AI vs. expertise — the paradox of access
    1:11:00 – The future of marketing AI and closing thoughts

    Host:

    Amit Prakash – CEO and Founder at AmpUp, Co-Founder CTO at ThoughtSpot,former engineer at Google AdSense and Microsoft Bing, with extensive expertise in distributed systems and machine learning.

    Guest:

    Abhay Parasnis –Abhay Parasnis is the founder & CEO at Typeface.ai - a leading Enterprise Generative AI company. Abhay is also a board member at Dropbox & Schneider Electric. Additionally, abhay is an active early stage investor & advisor for various AI startups including Common Sense Machines, Perplexity.ai, Pecan.ai, Pindrop, Spawning & others. Previously, Abhay was the CTO, CPO & EVP of Adobe, from 2015 to 2022 & was General Manager at Microsoft for a decade from 2002-2011.

    Follow the Hosts and the Guest:

    • Amit Prakash
      LinkedIn - https://www.linkedin.com/in/amit-prakash-50719a2/
      Twitter/X - https://x.com/amitp42
    • Abhay Parasnis
      LinkedIn – https://www.linkedin.com/in/abhayparasnis/
      Twitter/X – https://x.com/parasnis

    Share Your Thoughts:

    Have questions, comments, or ideas for future episodes? Email us at EffortlessPodcastHQ@gmail.com

    Don’t forget to Like, Comment, and Subscribe for more conversations at the intersection of AI, technology, and innovation.
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    1 h y 20 m
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