The Scaleup Flight
The Scaleup Flight
Podcast Description
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.
Podcast Insights
Content Themes
The podcast focuses on entrepreneurship, innovation, and growth strategies, with episodes like 'Affinity – The AdTech Rocketship' discussing the growth of a $100M ARR firm and 'The Resurgence of Travel & Resilience of ITILITE' exploring strategies for navigating post-COVID challenges in travel management. Key themes include adaptability, data-driven decision-making, and maintaining work-life balance.
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.
Guest: Priya Saiprasad — Co-Founder & General Partner, Touring Capital
Host: Peeyush Upadhyay — Managing Partner, Pekamiar
In 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 TimeStamps
Introduction: Highlights & Welcoming Priya Saiprasad
Why diversity in VC is essential to finding true alpha
The M12 female founders initiative & uncovering overlooked founder talent
How a global childhood shaped resilience, adaptability, and founder empathy
Why the founder journey is inherently nonlinear—and deeply lonely
Square, Jack Dorsey, and the power of true meritocracy
A painful early investing lesson: product strength vs. “why now” markets
Contrarian investing, herd mentality, and resisting FOMO in hot markets
Why “tech as a moat” is eroding in the AI era
Capital efficiency vs. growth at all costs (and the Zoom example)
Where AI investing is overcrowded—and where real opportunity lies
What Priya looks for in a 30-minute founder pitch
How founders should diligence investors (beyond the size of the check)
Why most scale-up failures ultimately come down to talent decisions
The VC as confidant: trust, vulnerability, and founder peer networks
How Priya competes, takes risks, and shows conviction
Advice for leaders in the AI era: GTM, pricing, and staying relevant
Key Takeaways
Alpha 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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