Nov 30, 2020 · 53m · neon-show
Beerud Sheth on building Elance (nowUpwork) & Gupshup
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gold bands on the timeline = statements, start to end. Hover to read, click to jump. CC turns on captions
On the 100x Entrepreneur Podcast, Beerud Sheth details his journey founding Elance (now Upwork) and building Gupshup into a profitable enterprise messaging unicorn. He shares key perspectives on navigating dot-com market shifts, executing crucial business pivots, and leading the future of conversational commerce.
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 1.9 Guest teaching 2.7 Guest disagreement 0.3 Siddhartha pushing back 0.2
speaking balance: gold is Siddhartha, purple is the guest (3 minute bins)
Sharpest disagreement ▶ 33:04 Reframing unicorn hype around funding vs profitability
Beerud pushes back against the common obsession with funding announcements and paper valuations, noting that unprofitable companies raise repeatedly while profitable ones grow quietly.
Hardest push from Siddhartha ▶ 47:27 Restating question on three core business mistakesSiddharth interjects to gently steer Beerud back on track to answer the specific question about the three major business mistakes he committed.
Biggest teaching moment ▶ 16:38 Correcting the host on Elance, oDesk, and Upwork timelineBeerud clarifies the host's mistaken assumption that he managed Elance through its merger and NASDAQ bell ringing, detailing his actual board role and the separate timeline of the merger.
Siddhartha holds their own ▶ 41:22 Host validates remote-control commerce with real-world Indian dining dataSiddharth contributes concrete domain validation by describing how contactless QR code ordering has already eliminated counter transactions across restaurants in India.
the scores for every segment, with the reasoning behind each
| Chapter | Topic | Siddhartha as informed peer | Guest teaching | Guest disagreement | Siddhartha pushing back | Why |
|---|---|---|---|---|---|---|
| Academic Roots at IIT Bombay, MIT, and Wall Street Trading | 1 | 2 | 0 | 0 | Siddharth opens with a broad question asking Beerud about his journey from IIT Bombay to becoming a large company founder. Beerud gives a detailed narrative on his academic path at MIT and transition into Wall Street quantitative trading. | |
| Transitioning from Wall Street to Entrepreneurship in the Dot-Com Era | 2 | 3 | 1 | 0 | Siddharth reflects on the structured nature of the Indian education system, which Beerud expands upon before explaining how the mid-90s dot-com boom inspired him to leave Wall Street for tech entrepreneurship. | |
| Founding Elance and Scrappy Execution in New York | 1 | 3 | 0 | 0 | Siddharth prompts Beerud to explain the founding of Upwork/Elance. Beerud provides a masterclass on combining global talent pools, internet connectivity, and Wall Street marketplace dynamics to pioneer online freelancing. | |
| Scaling Elance, Enterprise Pivot, and the Path to Upwork IPO | 2 | 4 | 1 | 1 | Siddharth asks about the scale when Beerud left and assumes he stayed through the Upwork merger and IPO bell ringing. Beerud gently corrects the timeline, explaining he stepped back earlier, stayed on the board, and attended the IPO as a founder guest. | |
| Evolution of the Gig Economy and Angel Investments | 3 | 2 | 0 | 0 | Siddharth cites market valuations like Fiverr to highlight the gig economy's growth and mentions Beerud's angel investment in Pepper. Beerud discusses how mobile and GPS enabled hyper-local iterations of the freelancing concept he started in 1998. | |
| The Genesis of Gupshup and Pivoting to Enterprise B2B | 1 | 3 | 0 | 0 | Beerud details the origin of Gupshup, from the failure of offline search (Webaroo) to building an SMS-based social network with 70 million users in India, before pivoting to enterprise B2B messaging due to monetization constraints. | |
| Gupshup's Enterprise Messaging Scale and WhatsApp Business Partnership | 2 | 2 | 0 | 0 | Siddharth asks about Gupshup's current revenue scale and partnership with WhatsApp Business. Beerud shares that the company is processing billions of messages and explains the transition from plain SMS to interactive IP messaging. | |
| Financial Discipline, Unicorn Status, and the Smart Messaging Vision | 2 | 3 | 1 | 0 | Siddharth points out that Gupshup is a quiet unicorn by valuation and asks about IPO and scaling goals. Beerud explains why bootstrapping profitably reduced PR hype compared to VC-funded peers and outlines his smart messaging vision comparing it to WeChat. | |
| The Rise of Conversational Commerce and Interactive Experiences | 3 | 2 | 0 | 0 | Siddharth brings up real-world restaurant QR code ordering in India as proof of contact-free digital systems. Beerud takes this further, explaining why static menus fall short for consultative sales and how conversational AI fills the gap. | |
| Core Entrepreneurial Lessons, Strategic Focus, and Common Pitfalls | 2 | 3 | 0 | 1 | Siddharth asks for three specific mistakes and three right decisions for founders. Beerud provides foundational advice on emotional resilience, prioritizing strategic focus over daily noise, and avoiding hiring purely based on resume prestige. |
Statements from this episode (13)
Indian education cultivates herd mentality over multidimensional reality
“The consequence of it is most people don't think what they want to do. You just sort of follow the, you know, follow the herd, if you will, you know, everybody, you know, oftentimes people do what their friends are doing or what you're, you know, what is highl…”
Elance scaled to 20 employees in a two-bedroom NYC apartment
“We grew to about 20 people in this two bedroom apartment”
Pre-merger, Elance focused on fixed-price projects while oDesk targeted hourly
“The difference was Elance focused on fixed price projects while Odesk focused on hourly projects, right?”
Elance is the only late-90s gig economy startup to survive
“We were literally the only company from that era
That has survived, right?
Like freelance you know, we founded it in December of 98.
Right.
And there were there were a few other companies.
There was one called guru.
There were some one called moonlighter and a…”
Gupshup reached 70M Indian users when Facebook and Twitter had 1M
“And it actually grew to seventy million users in India at a time where Facebook and Twitter had only like one million users in India, right?”
Gupshup generates well over $100 million in annual revenue
“We are well over a hundred million dollars in revenue.”
Gupshup processes four to five billion messages every month
“We handle about Four to five billion messages a month.”
Gupshup has remained profitable without major funding since 2011
“Our last round was in 2011, right? It was a ten million dollar round. And since then we've you know, we've been profitable for a very long time. We haven't done any major funding rounds.”
Messaging-based chatbots will replace many standalone apps
“A lot of apps will get actually replaced by messaging based chatbots and so on.”
Very soon, all workers will operate as remote freelancers
“Very soon we'll get to a world where everyone who's working will be working from home and working as a freelancer of sorts right now, you may have a long-term contract, but you're still working remote work.”
Future generations will view physical offices and factories as obsolete
“You know, the next generation, like our kids will wonder saying people used to go to something called a factory or an office. What does that mean? Because, you know, you bring the office into the home and you work wherever you are. I mean, you could live in Go…”
Conversational interfaces are the most flexible foundation for digital commerce
“And I think conversations is the thing that becomes you know, the lowest common denominator. Again, it's sort of the most universal thing because it is the most flexible. It can take care of every situation, right?”
Grinding 15 hours a day on micro-tasks kills startups
“Usually it's not the small stuff that will kill you. It's the big stuff that will kill companies. So So really there used to be a time that I used to think, oh, if I work, you know, 15 hours a day, or when I used to I drive, you know, that would be, that would…”