• 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 Std. und 3 Min.
  • 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 Min.
  • 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 Min.
  • 'Focus on Winning Together' in Healthcare AI
    Mar 25 2025

    In this conversation, Ankit Jain, Co-Founder & CEO of Infinitus, discusses with Peeyush Upadhyay, Managing Partner at Pekamiar, the importance of vulnerability in leadership, the need to focus on people rather than titles in startups, and the journey of a serial entrepreneur transitioning from founder to investor. He emphasizes the significance of understanding customer needs and the potential of healthcare technology, particularly in automating communication processes. The discussion highlights the challenges and opportunities in scaling a business while maintaining a strong company culture. In this conversation, Ankit shares Infinitus' journey from identifying a significant problem in healthcare to building a product that addresses it. He, then, touches upon the evolution of their Technology, and the importance of a diverse founding team, highlighting how COVID-19 accelerated their mission. The conversation also delves into the company's culture, values, and the significance of defining success beyond mere numbers. Ankit delves into the intersection of AI and healthcare, emphasizing the importance of viewing technology as a tool to enhance human capabilities rather than a threat. The discussion then segues into the complexities of hiring in startups, the significance of cultural fit, and the role of people operations in maintaining a strong organizational culture. The dialogue also touches on the challenges of scaling a company while prioritizing people, the adoption of AI in operations, and the balance between work and family life. Finally, Ankit shares some powerful insights on leadership, vulnerability, and the human element in guiding teams towards success.



    Titles

    Embracing Vulnerability in Leadership

    The Importance of People in Business

    Rethinking Titles and Roles in Startups

    The Journey of a Serial Entrepreneur

    Transitioning from Founder to Investor

    Identifying Opportunities in Healthcare



    Chapters

    00:00 Embracing Vulnerability in Leadership

    06:02 Rethinking Titles and Roles in Startups

    12:02 Transitioning from Founder to Investor

    14:51 Identifying Opportunities in Healthcare

    18:03 Building a Company with Purpose

    20:34 Identifying Problems and Building Solutions

    21:30 The Evolution of Infinitus' Product

    22:58 Learning from Industry Pioneers

    24:19 The Naming Journey of Infinitus

    25:32 Building a Diverse Founding Team

    27:34 The Impact of COVID-19 on Healthcare

    29:53 Defining Company Culture and Values

    33:13 The Importance of Winning Together

    37:02 How to Win: Beyond Numbers

    41:08 Building Relationships with Customers

    42:33 AI as a Complement to Healthcare

    43:30 Hiring Dynamics in Startups

    44:31 Understanding Cost in Hiring

    45:04 The Importance of Cultural Fit

    46:01 Interviewing and Decision-Making

    47:35 Encouraging Open Communication

    48:04 Cultural Custodians in Organizations

    49:31 People Operations and Culture

    50:01 Attracting Top Talent to Infinitus

    52:26 Scaling Challenges and People Focus

    54:06 AI Adoption in Operations

    55:08 Balancing Work and Family Life

    58:32 Advice for Early-Stage Founders

    01:00:01 The Human Element in Leadership

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    1 Std. und 3 Min.
  • Transforming Tech with Trmeric - In conversation with Siddharth Bohra, Founder & CEO.
    Mar 11 2025

    In this episode, Siddharth Bohra, Founder & CEO of Trmeric, talks about his journey starting out as a commerce graduate to leading multi-billion dollar businesses at Global Tech firms to founding Trmeric, emphasizing the importance of learnability and team building. He shares insights on navigating customer needs, the genesis of Trmeric, and the evolution of its product offerings. The discussion highlights the significance of AI in product development and the modular nature of Trmeric's services, as well as the role of AI co-pilots in enhancing user experience. Siddharth also elaborates on curating a network of service providers and the future directions for Trmeric. In this conversation, the founder discusses the journey of building Trmeric, focusing on product development, user experience, and the importance of customer feedback. He emphasizes the need for a roadmap for future growth, the challenges of fundraising, and the significance of creating a strong company culture. The discussion also touches on the attributes sought in team members, the learning curve in a startup environment, and advice for aspiring entrepreneurs.


    Key Topics

    The Journey of Learnability and Team Building

    Navigating Customer Needs and Product Vision

    The Genesis of Trmeric: From Idea to Reality

    Identifying Market Problems and Solutions

    Building the Prototype and Gathering Feedback

    The Evolution of Turmeric's Product Offering

    Leveraging AI in Product Development


    Chapters

    00:00 The Journey of Learnability and Team Building

    03:10 Navigating Customer Needs and Product Vision

    05:45 The Genesis of Trmeric: From Idea to Reality

    09:11 Identifying Market Problems and Solutions

    12:02 Building the Prototype and Gathering Feedback

    15:07 The Evolution of Trmeric's Product Offering

    17:50 Leveraging AI in Product Development

    21:00 Understanding the Modular Nature of Trmeric

    23:57 The Role of AI Co-Pilots in Enhancing User Experience

    26:58 Curating a Network of Service Providers

    30:03 Future Directions and Innovations for Trmeric

    38:28 Building a Roadmap for the Future

    44:10 Focus on Product Experience and User Empowerment

    48:20 Navigating Fundraising and Growth Strategies

    51:32 Scaling Plans and Team Expansion

    54:18 Key Attributes for Team Recruitment

    57:46 Defining Company Culture and Values

    01:00:27 Learning and Growth in a Startup Environment

    01:06:20 Overcoming Self-Doubt and Staying Motivated

    01:10:58 Advice for Aspiring Entrepreneurs

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

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    1 Std. und 15 Min.
  • Affinity – The AdTech Rocketship - $10M to $100M in 5Y - With Lavin Punjabi, Co-Founder & CEO
    Jan 14 2025

    In this conversation, Lavin Punjabi, Co-Founder & CEO of Affinity, a hyper-growth $100M ARR AdTech firm, talks with Peeyush Upadhyay, Managing Partner at Pekamiar, about his entrepreneurial journey and Affinity's growth story detailing its evolution from a domain parking company to a leader in performance advertising. He shares insights on the company's evolution over the years through multiple pivots and the importance of adaptability, risk-taking, and a growth-led mindset that helped build innovative solutions that led to significant revenue growth. The discussion emphasizes the value of data-driven decision-making and the necessity of maintaining profitability while pursuing new ventures. Lavin talks about Affinity's strategic response to tectonic shifts in the Advertising industry, and the company's conscious decision to invest in privacy-friendly, cookie-less, and AI-powered product strategy and development. He emphasizes the importance of building a strong team culture, the challenges of establishing a global brand, and the balance between work and family life. The discussion also touches on the significance of taking risks and being data-driven in entrepreneurship.



    Chapters

    00:00

    The Evolution of Affinity: A Journey of Growth

    10:02

    Navigating Challenges: The Importance of Adaptation

    20:00

    Innovative Solutions: Monetizing Mistakes

    30:01

    The Future of Affinity: Sustainable Growth and Profitability

    30:56

    Navigating the Cookie-less Future

    34:46

    Harnessing AI for Growth

    40:36

    Building a Strong Team and Culture

    46:08

    Mergers and Cultural Synergy

    52:17

    Establishing a Global Brand

    55:13

    Balancing Work and Family Life

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

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    1 Std. und 1 Min.
  • The Resurgence of Travel & Resilience of ITILITE with Mayank Kukreja: From $0 Revenue during COVID to 4X Growth in 2024
    Dec 23 2024

    In this episode of The Scale Up Flight, Peeyush Upadhyay interviews Mayank Kukreja, Co-Founder and CEO of ITILITE, discussing the challenges and triumphs of scaling a startup in the B2B Travel and Expense Management category. They explore Mayank’s journey from his Consulting days at McKinsey to entrepreneurship, the importance of identifying market needs, and the strategies for navigating the fundraising landscape. The conversation highlights the innovative solutions ITLITE offers to streamline business travel and expense processes, especially in a post-COVID world. In this conversation, Mayank shares insights on navigating VC relationships, building a founding team, and the evolution of a founder's role. He emphasizes the importance of choosing the right VC partners, the need for a T-profile approach in hiring, and the necessity of letting go and delegating responsibilities as the company grows. Peeyush also talks to Mayank about the adoption of AI in Travel & Expense SasS, balancing technology with human interaction. Finally, Mayank reflects on personal growth, work-life balance, and the importance of stepping back to reassess one's journey.

    Chapters (Episode – 1)

    00:00 - Introduction to The Scale Up Flight Podcast

    01:49 - Understanding ITILITE's All-in-One Platform

    04:58 - Mayank’s Journey from Consulting to Entrepreneurship

    12:36 - Identifying the Problem and Market Fit

    19:19 - Expanding into New Markets Post-COVID

    27:32 - Building a Comprehensive Travel, Expense & Card Solution

    30:34 - Navigating the Fundraising Landscape

    33:29 - Navigating VC Relationships During Uncertain Times

    38:19 - Building a Founding Team: The T-Profile Approach

    41:29 - Evolving as a Founder: Letting Go and Delegating

    49:12 - AI in Travel: Balancing Technology and Human Touch

    57:55 - Scaling Leadership: Finding the Right Fit

    01:01:05 - Personal Reflections: Balancing Work and Life

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

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    1 Std. und 7 Min.