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Mar 28, 2022 · 33m · neon-show

Yadhu Gopalan On His Journey, Meeting His Co-Founder & Learnings From Amazon & Microsoft!

Yadhu Gopalan · 26m spoken Siddhartha Ahluwalia · 3m spoken Amit Somani · 35s spoken
0:00 / 0:00
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In this episode of 100x Entrepreneur, Esper co-founder and CEO Yadhu Gopalan shares his transition from leading systems engineering at Microsoft and Amazon to building a category-defining DevOps platform for dedicated enterprise hardware fleets.

How this conversation actually went

Every chapter scored 0–10 on four independent dynamics. Hover any point for the reasoning behind the score. How this is scored →

Siddhartha as informed peer 2.4 Guest teaching 2.6 Guest disagreement 0.0 Siddhartha pushing back 0.0
05100:0010:0020:0030:004:40–7:42 · Siddhartha as informed peer 2/10 Early Childhood, Moving to Maine, and Programming Beginnings The host asks broad biographical and origin questions. Yadhu educates the host on the legacy challenges of hardware release cycles and the infrastructure overhead he faced building Amazon Go.7:42–10:51 · Siddhartha as informed peer 2/10 Dedicated Devices, Fleet Trust, and Industry Applications Yadhu explains the core technical dilemma of edge devices: unlike the cloud, pushing faulty patches risks bricking hardware fleets, requiring dedicated trust and tooling.10:51–14:26 · Siddhartha as informed peer 2/10 Enterprise Use Cases in Global Retail and Hospitality The conversation is highly collaborative as the host prompts Yadhu for enterprise case studies and the origin of his partnership with co-founder Shiv Sundar.14:27–17:59 · Siddhartha as informed peer 3/10 Esper's Growth Metrics, Funding Rounds, and Product-Market Fit The host tracks business metrics closely and extrapolates device milestone numbers, while Yadhu lays out Esper's funding history and exponential customer adoption.18:00–21:19 · Siddhartha as informed peer 2/10 Global Team Dynamics Across India and the United States Siddharth asks standard operational questions about cross-border leadership between India and the US, which Yadhu addresses with praise for local engineering talent in Bangalore.21:20–27:02 · Siddhartha as informed peer 4/10 Navigating Enterprise Hardware Ecosystems and Strategic Partnerships The host articulates an informed insight about founders struggling with distribution and hardware partnerships. Yadhu details how his time at Microsoft and Amazon shaped his management and customer obsession.27:03–30:00 · Siddhartha as informed peer 2/10 Esper's Cultural Pillars, Employee Growth, and Bangalore Office A straightforward inquiry into company values leads Yadhu to describe Esper's three core principles and their dedication to in-office collaboration.30:00–33:20 · Siddhartha as informed peer 2/10 Foundational Advice for Entrepreneurs and Lifelong Learning Habits The host closes with classic reflective founder questions regarding entrepreneurial advice and continuous learning routines.4:40–7:42 · Guest teaching 4/10 Early Childhood, Moving to Maine, and Programming Beginnings The host asks broad biographical and origin questions. Yadhu educates the host on the legacy challenges of hardware release cycles and the infrastructure overhead he faced building Amazon Go.7:42–10:51 · Guest teaching 5/10 Dedicated Devices, Fleet Trust, and Industry Applications Yadhu explains the core technical dilemma of edge devices: unlike the cloud, pushing faulty patches risks bricking hardware fleets, requiring dedicated trust and tooling.10:51–14:26 · Guest teaching 3/10 Enterprise Use Cases in Global Retail and Hospitality The conversation is highly collaborative as the host prompts Yadhu for enterprise case studies and the origin of his partnership with co-founder Shiv Sundar.14:27–17:59 · Guest teaching 2/10 Esper's Growth Metrics, Funding Rounds, and Product-Market Fit The host tracks business metrics closely and extrapolates device milestone numbers, while Yadhu lays out Esper's funding history and exponential customer adoption.18:00–21:19 · Guest teaching 2/10 Global Team Dynamics Across India and the United States Siddharth asks standard operational questions about cross-border leadership between India and the US, which Yadhu addresses with praise for local engineering talent in Bangalore.21:20–27:02 · Guest teaching 3/10 Navigating Enterprise Hardware Ecosystems and Strategic Partnerships The host articulates an informed insight about founders struggling with distribution and hardware partnerships. Yadhu details how his time at Microsoft and Amazon shaped his management and customer obsession.27:03–30:00 · Guest teaching 1/10 Esper's Cultural Pillars, Employee Growth, and Bangalore Office A straightforward inquiry into company values leads Yadhu to describe Esper's three core principles and their dedication to in-office collaboration.30:00–33:20 · Guest teaching 1/10 Foundational Advice for Entrepreneurs and Lifelong Learning Habits The host closes with classic reflective founder questions regarding entrepreneurial advice and continuous learning routines.4:40–7:42 · Guest disagreement 0/10 Early Childhood, Moving to Maine, and Programming Beginnings The host asks broad biographical and origin questions. Yadhu educates the host on the legacy challenges of hardware release cycles and the infrastructure overhead he faced building Amazon Go.7:42–10:51 · Guest disagreement 0/10 Dedicated Devices, Fleet Trust, and Industry Applications Yadhu explains the core technical dilemma of edge devices: unlike the cloud, pushing faulty patches risks bricking hardware fleets, requiring dedicated trust and tooling.10:51–14:26 · Guest disagreement 0/10 Enterprise Use Cases in Global Retail and Hospitality The conversation is highly collaborative as the host prompts Yadhu for enterprise case studies and the origin of his partnership with co-founder Shiv Sundar.14:27–17:59 · Guest disagreement 0/10 Esper's Growth Metrics, Funding Rounds, and Product-Market Fit The host tracks business metrics closely and extrapolates device milestone numbers, while Yadhu lays out Esper's funding history and exponential customer adoption.18:00–21:19 · Guest disagreement 0/10 Global Team Dynamics Across India and the United States Siddharth asks standard operational questions about cross-border leadership between India and the US, which Yadhu addresses with praise for local engineering talent in Bangalore.21:20–27:02 · Guest disagreement 0/10 Navigating Enterprise Hardware Ecosystems and Strategic Partnerships The host articulates an informed insight about founders struggling with distribution and hardware partnerships. Yadhu details how his time at Microsoft and Amazon shaped his management and customer obsession.27:03–30:00 · Guest disagreement 0/10 Esper's Cultural Pillars, Employee Growth, and Bangalore Office A straightforward inquiry into company values leads Yadhu to describe Esper's three core principles and their dedication to in-office collaboration.30:00–33:20 · Guest disagreement 0/10 Foundational Advice for Entrepreneurs and Lifelong Learning Habits The host closes with classic reflective founder questions regarding entrepreneurial advice and continuous learning routines.4:40–7:42 · Siddhartha pushing back 0/10 Early Childhood, Moving to Maine, and Programming Beginnings The host asks broad biographical and origin questions. Yadhu educates the host on the legacy challenges of hardware release cycles and the infrastructure overhead he faced building Amazon Go.7:42–10:51 · Siddhartha pushing back 0/10 Dedicated Devices, Fleet Trust, and Industry Applications Yadhu explains the core technical dilemma of edge devices: unlike the cloud, pushing faulty patches risks bricking hardware fleets, requiring dedicated trust and tooling.10:51–14:26 · Siddhartha pushing back 0/10 Enterprise Use Cases in Global Retail and Hospitality The conversation is highly collaborative as the host prompts Yadhu for enterprise case studies and the origin of his partnership with co-founder Shiv Sundar.14:27–17:59 · Siddhartha pushing back 0/10 Esper's Growth Metrics, Funding Rounds, and Product-Market Fit The host tracks business metrics closely and extrapolates device milestone numbers, while Yadhu lays out Esper's funding history and exponential customer adoption.18:00–21:19 · Siddhartha pushing back 0/10 Global Team Dynamics Across India and the United States Siddharth asks standard operational questions about cross-border leadership between India and the US, which Yadhu addresses with praise for local engineering talent in Bangalore.21:20–27:02 · Siddhartha pushing back 0/10 Navigating Enterprise Hardware Ecosystems and Strategic Partnerships The host articulates an informed insight about founders struggling with distribution and hardware partnerships. Yadhu details how his time at Microsoft and Amazon shaped his management and customer obsession.27:03–30:00 · Siddhartha pushing back 0/10 Esper's Cultural Pillars, Employee Growth, and Bangalore Office A straightforward inquiry into company values leads Yadhu to describe Esper's three core principles and their dedication to in-office collaboration.30:00–33:20 · Siddhartha pushing back 0/10 Foundational Advice for Entrepreneurs and Lifelong Learning Habits The host closes with classic reflective founder questions regarding entrepreneurial advice and continuous learning routines.

speaking balance: gold is Siddhartha, purple is the guest (3 minute bins)

0:00 · Siddhartha 0% · guest 100%0:00 · Siddhartha 0% · guest 100%3:00 · Siddhartha 0% · guest 100%3:00 · Siddhartha 0% · guest 100%6:00 · Siddhartha 0% · guest 100%6:00 · Siddhartha 0% · guest 100%9:00 · Siddhartha 0% · guest 100%9:00 · Siddhartha 0% · guest 100%12:00 · Siddhartha 0% · guest 100%12:00 · Siddhartha 0% · guest 100%15:00 · Siddhartha 0% · guest 100%15:00 · Siddhartha 0% · guest 100%18:00 · Siddhartha 0% · guest 100%18:00 · Siddhartha 0% · guest 100%21:00 · Siddhartha 0% · guest 100%21:00 · Siddhartha 0% · guest 100%24:00 · Siddhartha 0% · guest 100%24:00 · Siddhartha 0% · guest 100%27:00 · Siddhartha 0% · guest 100%27:00 · Siddhartha 0% · guest 100%30:00 · Siddhartha 0% · guest 100%30:00 · Siddhartha 0% · guest 100%33:00 · Siddhartha 0% · guest 100%33:00 · Siddhartha 0% · guest 100%
Sharpest disagreement ▶ 24:45 Pragmatism Over Enterprise Over-Engineering

In a non-combative interview, this represents Yadhu's sharpest contrarian view, cautioning against naively copying Big Tech processes that lead to overbuilding in early-stage startups.

 Hardest push from Siddhartha ▶ 21:20 Framing the Distribution Skill Bottleneck

The host challenges conventional startup founder archetypes by emphasizing that most technical founders fail at partnerships and distribution at scale.

 Biggest teaching moment ▶ 7:49 The Reality of Device vs Cloud DevOps

Yadhu breaks down the fundamental architectural gap between cloud software agility and the high-risk operational barrier of updating physical fleets.

 Siddhartha holds their own ▶ 21:20 Identifying Ecosystem Bottlenecks

The host demonstrates deep ecosystem knowledge by differentiating between product builders and founders capable of complex hardware partner distribution.
the scores for every segment, with the reasoning behind each
ChapterTopicSiddhartha as informed peerGuest teachingGuest disagreementSiddhartha pushing backWhy
Early Childhood, Moving to Maine, and Programming Beginnings 2400 The host asks broad biographical and origin questions. Yadhu educates the host on the legacy challenges of hardware release cycles and the infrastructure overhead he faced building Amazon Go.
Dedicated Devices, Fleet Trust, and Industry Applications 2500 Yadhu explains the core technical dilemma of edge devices: unlike the cloud, pushing faulty patches risks bricking hardware fleets, requiring dedicated trust and tooling.
Enterprise Use Cases in Global Retail and Hospitality 2300 The conversation is highly collaborative as the host prompts Yadhu for enterprise case studies and the origin of his partnership with co-founder Shiv Sundar.
Esper's Growth Metrics, Funding Rounds, and Product-Market Fit 3200 The host tracks business metrics closely and extrapolates device milestone numbers, while Yadhu lays out Esper's funding history and exponential customer adoption.
Global Team Dynamics Across India and the United States 2200 Siddharth asks standard operational questions about cross-border leadership between India and the US, which Yadhu addresses with praise for local engineering talent in Bangalore.
Navigating Enterprise Hardware Ecosystems and Strategic Partnerships 4300 The host articulates an informed insight about founders struggling with distribution and hardware partnerships. Yadhu details how his time at Microsoft and Amazon shaped his management and customer obsession.
Esper's Cultural Pillars, Employee Growth, and Bangalore Office 2100 A straightforward inquiry into company values leads Yadhu to describe Esper's three core principles and their dedication to in-office collaboration.
Foundational Advice for Entrepreneurs and Lifelong Learning Habits 2100 The host closes with classic reflective founder questions regarding entrepreneurial advice and continuous learning routines.

Statements from this episode (8)

Assertion Not checkable as stated
Yadhu Gopalan: Amazon Go engineers spent six months solely on infrastructure
“When I was in Amazon, Amazon goes an example is we had to build out this new systems and new devices for these amazing stores. And you know what? We spent, I think the first six months or more just building infrastructure and before we could actually do the va…”
Yadhu Gopalan Mar 28, 2022 ▶ 6:58
Insight
Gopalan: Hardware teams hesitate to push updates for fear of bricking devices
“Right now, it's taken for granted on the cloud. Like, I got a security patch that I have to push out. It's like, within weeks, you're like working on, as soon as you got a solution, you're pushing it up. Devices is like you're paranoid about what you need, wha…”
Yadhu Gopalan Mar 28, 2022 ▶ 8:16
Assertion Not checkable as stated
Gopalan: Modern restaurant locations run at least 15 to 16 cloud-connected devices
“If you look at a restaurant these days, like 15, 16 devices per store at the minimum, from the kitchen display, what's in the kitchen backroom, to point of sale, to what ordering, To tabletop, to self-service kiosk, they want, and they're all cloud connected n…”
Yadhu Gopalan Mar 28, 2022 ▶ 11:04
Disclosure
Gopalan: Esper manages 2,000 devices per location across thousands of retail stores
“Another example is in a retail store that we have. There's I mean, it's a product that I can't talk about too much, but as you, you're talking about 2000 devices per store. And, It's an amazing use case. And you can, and there are thousands of these stores and…”
Yadhu Gopalan Mar 28, 2022 ▶ 11:59
Assertion Not checkable as stated
Yadhu Gopalan says Esper grew revenue 4x and devices 18x in 2021
“We saw Forex growth in revenue from 20 20, we had We ended the number of customers, logos around 202 hundred, around 250 3000 or more customers using our platform 18 X the number of devices.”
Yadhu Gopalan Mar 28, 2022 ▶ 15:52
Prediction Not checkable as stated
Yadhu Gopalan says Esper is adding 1,500 new devices every day
“The amazing thing is right now we're growing at more than 1500 devices per day. And we'll get there about, like, we're predicting about 50,000 devices within the next couple of months.”
Yadhu Gopalan Mar 28, 2022 ▶ 17:25
Opinion
Yadhu Gopalan: Amazon is the ultimate training ground for engineering managers
“Amazon is one place where I think they build great engineering managers. So you get a sample of, like, how it is to build and manage huge, complex systems.”
Yadhu Gopalan Mar 28, 2022 ▶ 24:31
Assertion Not checkable as stated
Yadhu Gopalan claims Esper maintains absolutely zero customer churn
“It's testament to like the zero churn we have across the board. We have customers that love us and will give, give feedback.”
Yadhu Gopalan Mar 28, 2022 ▶ 26:12
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