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The Scaleup Flight

The Scaleup Flight

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 Career Success Economics Leadership Management & Leadership
Episodes
  • Hiring Decisions That Make & Break Startups | Beth Scheer, Theory Ventures

    Hiring Decisions That Make & Break Startups | Beth Scheer, Theory Ventures
    Oct 5 2026

    In this conversation, Peeyush Upadhyay, Managing Partner at Pekamiar, sits down with Beth Scheer, Head of Talent Intelligence at Theory Ventures.


    Beth explains why founders overhire without realising it, and why that is the most expensive mistake she sees. What to tell a founder whose engineer has a million dollar offer from a frontier lab, and why a candidate interviewing at the big labs at the same time is usually window shopping. How she counsels founders who have been told by their board to hire a CRO when what they need is a founding AE.


    She breaks down what a modern talent function at a fund actually does, from diligence through the first ninety days after a cheque is signed. She is candid about how she picks search firms, why she wants the partner making the calls rather than someone a year out of college, and why "no search firms, please" sits on her LinkedIn profile.


    On what goes wrong, her answer is calibration. Almost every search that breaks, breaks in the same place, and it is rarely the search firm.


    She also gets into what a fourteen person fund with five AI engineers changes about her job, how you measure a role that has no obvious metrics, synthetic resumes and candidates who turn out not to be real people, why she has always gone to work for people rather than companies, and what happens to leadership in five years when nobody is hiring juniors today.


    This is the first episode in a new series on The Scaleup Flight, featuring the talent leaders inside VC funds. The people who watch hiring play out across an entire portfolio, and whose knowledge almost never gets written down anywhere.


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    CHAPTERS

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    00:00 Highlights

    03:18 1997 to 2026, and what has not changed about hiring

    04:53 When a frontier lab offers your engineer a million dollars

    06:39 Fourteen people, five AI engineers, one talent team

    12:49 "I'm a talent therapist"

    14:42 The three pillars of a modern talent function

    18:49 The first ninety days after the cheque is signed

    22:28 "No search firms, please"

    26:27 Why searches break. Calibration, calibration, calibration.

    31:45 How do you measure a job with no metrics

    35:08 Where inflection hires actually fall apart

    38:08 The number one executive hiring mistake

    41:41 Comp plans, and the discomfort filter

    44:49 Nobody is hiring juniors. So who leads in five years?

    45:54 How founders should vet a VC on talent


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    LINKS

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    Follow The Scaleup Flight on LinkedIn:

    https://www.linkedin.com/company/thescaleupflight


    Follow The Scaleup Flight on Instagram:

    https://www.instagram.com/thescaleupflightpodcast


    Follow Beth Scheer on LinkedIn:

    https://www.linkedin.com/in/bethscheer/


    Follow Peeyush Upadhyay on LinkedIn:

    https://www.linkedin.com/in/peeyushupadhyay/

    Hosted on Acast. See acast.com/privacy for more information.
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    47 mins
  • Investing in Cybersecurity When Attacks Scale Faster Than Defense | Partner at Decibel

    Investing in Cybersecurity When Attacks Scale Faster Than Defense | Partner at Decibel
    Sep 22 2026

    Peeyush Upadhyay sits down with Dan Nguyen-Huu, Partner at Decibel Partners, to discuss what he looks for in technical founders at the earliest stage, why timing kills more good ideas than competition does, and what the agent era is doing to cybersecurity.


    Dan explains why hustle is still the most underrated thing in AI, why he backs founders who are exceptional at one or two things rather than competent across the board, and why he now treats firm convictions as a liability when a single model release can reset a category. He also gets into the investment that failed because it arrived years before the technology could carry it, and how Decibel uses its community of early adopters to pressure test an idea before writing a cheque.


    Peeyush and Dan also dig into the OpenAI agent that broke out of its sandbox, Greg Brockman's "defender's window" and what it means when attacks scale with compute while detection and response still run at human speed, how the CISO profile has shifted toward practitioners out of the NSA and the DoD, and why the first commercial hire is the one founders almost always get wrong.



    Timestamps:

    00:00 - Intro

    02:04 - Why the Founder Who Gets on a Plane Still Wins

    03:48 - "Either a Purchase Order or a Restraining Order"

    07:49 - Why Decibel Backs the Plumbing, Not the Shiny Stuff

    10:10 - Banker, Operator, Investor: What Each Seat Taught Him

    16:09 - The Investment That Failed Because It Was Too Early

    18:21 - How Decibel's Early Adopters Kill or Confirm an Idea

    20:47 - When the Customers Say No and You Invest Anyway

    23:07 - Team, Market or Price: What Survives at Pre-Seed?

    23:50 - Why We Back Spikes, Not Well-Rounded Founders

    25:51 - Should You Raise Venture Money at All?

    27:16 - Why Product Market Fit Is Math, Not Magic

    29:11 - How Do You Separate Signal From Noise in AI Security?

    32:30 - The Agent That Broke Out of Its Sandbox

    35:22 - The Defender's Window & Why Defence Has to Scale

    37:27 - Is Your Voice Now an Identity Risk?

    39:28 - The New CISO Profile: Harder to Sell To Than Ever

    41:48 - Keeping a Thesis Alive When Models Ship Every Month

    45:32 - Where Technical Founders Get Go-To-Market Wrong

    48:17 - Why Talent Is Decibel's Differentiator

    49:35 - When the Business Outgrows the Founder Running It

    51:02 - Great Product, Great Team, Never Scaled: Why?

    53:26 - Quick-Fire Round


    Follow The Scaleup Flight Podcast on LinkedIn:

    https://www.linkedin.com/company/thescaleupflight


    Follow The Scalup Flight Podcast on Instagram:

    https://www.instagram.com/thescaleupflightpodcast


    Follow Dan Nguyen-Huu, on LinkedIn:

    https://www.linkedin.com/in/dan-nguyen-huu-11502719/


    Follow Peeyush Upadhyay on LinkedIn:

    https://www.linkedin.com/in/peeyushupadhyay/


    #thescaleupflight #pekamiar #cybersecurity #aisecurity #venturecapital #earlystage #founders

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    Show More Show Less
    56 mins
  • 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
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