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The Scaleup Flight

The Scaleup Flight

Written by: Peeyush Upadhyay
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The Scaleup Flight, hosted by Peeyush Upadhyay, is a series of fireside chats encapsulating some of the most incredible, intriguing, and inspiring scaleup journeys of Founders, Investors, and Executives. Free of jargon, buzzwords, and PR stunts, these are real, authentic, relatable, and humane conversations through which we get a peek into the entrepreneurial pursuits of those who had the courage and conviction to take the long flight and the capability to make an impact on the big stage.


Peeyush Upadhyay is the Co-Founder & Managing Partner at Pekamiar and serves as a trusted advisor to Tech startup Founders and C-suite and helps them accelerate their growth momentum by formulating and executing their Talent strategies. He partners with Early & Growth-stage Tech firms and helps them scale by helping build high-performance, diverse, and inclusive Leadership & GTM teams. Before founding Pekamiar, he worked at industry-leading global software & technology services firms like Automation Anywhere and Infosys in Sales & Strategic Partnerships roles.

Hosted on Acast. See acast.com/privacy for more information.

Peeyush Upadhyay Careers Economics Leadership Management & Leadership Personal Success
Episodes
  • Why Tech Moats Are Dying in AI — and What Actually Scales Instead - In Conversation with Priya Saiprasad, GP at TC

    Why Tech Moats Are Dying in AI — and What Actually Scales Instead - In Conversation with Priya Saiprasad, GP at TC
    Jan 5 2026
    Guest: Priya Saiprasad — Co-Founder & General Partner, Touring CapitalHost: Peeyush Upadhyay — Managing Partner, PekamiarIn this episode of The Scale Up Flight, Peeyush Upadhyay sits down with Priya Saiprasad, Co-Founder and General Partner at Touring Capital, a $330M early-growth fund backing SaaS and AI companies.Priya shares how her global upbringing—having lived in 12 countries by age 12—shaped her resilience, adaptability, and founder-first investing philosophy. Drawing from her experience at Square, Microsoft M12, Mayfield, and SoftBank Vision Fund, she unpacks what truly drives scale in today’s AI-powered economy.The conversation goes deep into what venture investors underestimate, why technology moats are eroding, and how capital efficiency, talent, and go-to-market defensibility are becoming the real differentiators. Priya also offers candid advice for founders on choosing the right investors, navigating board dynamics, making tough people decisions, and building companies that compound over time—not just ride hype cycles.This episode is a must-listen for SaaS and AI founders, operators, and investors navigating the Series B/C transition in an increasingly volatile market.Chapters with TimeStamps00:00 – 02:15Introduction: Highlights & Welcoming Priya Saiprasad02:16 – 06:10Why diversity in VC is essential to finding true alpha06:11 – 09:55The M12 female founders initiative & uncovering overlooked founder talent09:56 – 13:55How a global childhood shaped resilience, adaptability, and founder empathy13:56 – 18:30Why the founder journey is inherently nonlinear—and deeply lonely18:31 – 22:40Square, Jack Dorsey, and the power of true meritocracy22:41 – 26:40A painful early investing lesson: product strength vs. “why now” markets26:41 – 31:40Contrarian investing, herd mentality, and resisting FOMO in hot markets31:41 – 35:20Why “tech as a moat” is eroding in the AI era35:21 – 39:50Capital efficiency vs. growth at all costs (and the Zoom example)39:51 – 43:30Where AI investing is overcrowded—and where real opportunity lies43:31 – 47:10What Priya looks for in a 30-minute founder pitch47:11 – 49:55How founders should diligence investors (beyond the size of the check)49:56 – 52:40Why most scale-up failures ultimately come down to talent decisions52:41 – 55:50The VC as confidant: trust, vulnerability, and founder peer networks55:51 – 59:30How Priya competes, takes risks, and shows conviction59:31 – 01:02:00Advice for leaders in the AI era: GTM, pricing, and staying relevantKey TakeawaysAlpha isn’t obvious upfront — finding it requires looking beyond familiar networks and consensus thinking.Diversity in decision-makers leads to better outcomes for both venture portfolios and founders.The founder journey is a zigzag, requiring resilience, adaptability, and constant reinvention.Technology as a moat is diminishing in the AI era; defensibility now comes from GTM, data, distribution, and product virality.Capital efficiency matters more than headline valuation — valuation isn’t money in pocket until exit.Restraint is harder than deploying capital, especially in hot markets driven by FOMO.Great founders are intellectually curious, humble, and maniacally focused, not know-it-alls.Founders must diligence VCs on how they behave during downturns—not just when things go well.Everything ultimately boils down to talent — hiring, upgrading, and making tough people decisions at the right time.In AI, speed and relevance matter — pricing, packaging, and continuous innovation are critical to long-term retention. Hosted on Acast. See acast.com/privacy for more information.
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    1 hr and 3 mins
  • Transforming Automotive Retail with Spyne AI - In Conversation with Sanjay Varnwal, Co-Founder & CEO

    Transforming Automotive Retail with Spyne AI - In Conversation with Sanjay Varnwal, Co-Founder & CEO
    Nov 24 2025

    In this episode, Peeyush Upadhyay, Managing Partner of Pekamiar, sits down with Sanjay Varnwal, Co-founder & CEO of Spyne, to explore how they’re transforming automotive retail — from shaky smartphone photos on crowded lots to studio-quality images, 3D spins, immersive video, and AI-led digital retail.


    Sanjay walks through Spyne’s hard pivot from a generic computer vision platform to a deep auto vertical, explaining why they consciously gave up 80% of their revenue to find true product–market fit, and how they scaled from India into the US and Europe, working with over 3,200 dealerships globally.


    They talk about:


    How dealers can shoot studio-like car visuals using just a smartphone

    Why visuals dramatically change lead volume and conversions

    Building proprietary computer vision & generative models for auto

    Pivoting from multi-vertical to auto-only (and surviving the revenue dip)

    Using conversational AI to capture leads 24/7

    How to hire for new markets and build a US sales engine from India

    What founders should really focus on before raising a Series A


    If you’re building in AI, SaaS, or vertical software, or you’re a founder thinking about a painful but necessary pivot, this one is going to hit home.



    Chapters

    00:00: Introduction to Spine AI and Automotive Retail Transformation

    02:53: The Impact of Visual Presentation on Car Sales

    06:07: The Capture and Cleanup Process in Automotive Imaging

    08:57: The Shift to Specialization in the Automotive Industry

    11:44: Revenue Growth and Metrics for Success

    14:53: Customer Success Stories and Engagement Strategies

    17:52: Adapting to Market Changes and Technology Trends

    20:47: Expanding into a Broader Digital Retail Platform

    23:49: Fundraising and Future Growth Plans

    26:18: Unlocking Funding Success

    29:07: Navigating Market Challenges

    30:30: Scaling and International Expansion

    35:59: Hiring for Growth

    42:34: Cultural Cohesion and Leadership

    44:55: Future of AI in Auto Retail

    Hosted on Acast. See acast.com/privacy for more information.
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    50 mins
  • The Building of Innovaccer's Healthcare Intelligence Cloud with Sandy Gupta, Co-Founder & COO

    The Building of Innovaccer's Healthcare Intelligence Cloud with Sandy Gupta, Co-Founder & COO
    Jun 3 2025

    In this episode, Peeyush Upadhyay interviews Sandy Gupta, Co-Founder and COO of Innovaccer, discussing the journey of building the largest intelligent healthcare cloud. They explore the importance of co-founder chemistry, the transition from research to healthcare, and the challenges faced in integrating healthcare data. Sandy shares insights on the decision-making process, the significance of trust among co-founders, and the evolution of Innovator's solutions in the healthcare sector. Sandy then discusses the transformative role of data in healthcare, highlighting the shift toward value-based care and the significance of social demographics in patient outcomes. They discuss the challenges faced by the healthcare industry, including rising costs and the need for automation through AI. The conversation also touches on the significance of building a strong company culture and navigating tough leadership decisions in a rapidly changing environment.



    Chapters

    00:00 - Introduction to Innovaccer and Its Vision

    02:57 - The Journey of Founders and Their Chemistry

    05:58 - Transitioning from Research to Healthcare

    08:52 - The Decision to Focus on Healthcare

    12:01 - Building the Healthcare Intelligence Cloud

    14:52 - Challenges and Solutions in Healthcare Data

    17:57 - Scaling and Integrating Healthcare Solutions

    26:38 - Data-Driven Healthcare Transformation

    28:11 - Value-Based Care: A New Paradigm

    30:49 - The Role of Social Demographics in Healthcare

    32:57 - Preventative Care and Patient Insights

    34:13 - Healthcare Industry Trends and Challenges

    36:35 - AI and Automation in Healthcare

    37:32 - Vision for the Future of Healthcare

    40:09 - The Role of AI in Primary Care

    42:46 - Building a Strong Company Culture

    49:20 - Navigating Tough Decisions in Leadership

    Hosted on Acast. See acast.com/privacy for more information.
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    57 mins
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