Jun 1, 2020 · 1h 3m · neon-show
Inside the mind of Anand Chandrasekaran, on building 5 products with 10m+ users and angel investing
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In this episode of the 100x Entrepreneur Podcast, seasoned product leader and active angel investor Anand Chandrasekaran shares strategic insights on scaling enterprise SaaS, leading digital transformations, managing crises, and navigating early-stage venture investing.
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 2.9 Guest teaching 2.4 Guest disagreement 0.2 Siddhartha pushing back 0.6
speaking balance: gold is Siddhartha, purple is the guest (3 minute bins)
Sharpest disagreement ▶ 30:44 Pushing back on capital scarcity narrative
Anand politely rejects Siddhartha's premise that good companies fail merely from lack of capital in downturns, noting failure almost always traces back to cost structure and premature scaling.
Hardest push from Siddhartha ▶ 55:34 Host pushes back with Giphy dilution counterexampleSiddhartha directly challenges Anand's maxim to never sell early by citing the Giphy acquisition, illustrating how liquidation preferences of late-stage VCs can leave early angels with diminished returns.
Biggest teaching moment ▶ 40:20 Values must represent actionable trade-offsAnand explains why standard corporate platitudes are meaningless unless they represent genuine trade-offs, citing Facebook's move fast ethos as choosing velocity over slow perfection.
Siddhartha holds their own ▶ 55:34 Siddharth breaks down VC waterfall mechanicsSiddhartha demonstrates deep cap table and venture finance fluency by analyzing how early angel multiples get compressed by secondary rights and senior preference stacks in M&A transactions.
the scores for every segment, with the reasoning behind each
| Chapter | Topic | Siddhartha as informed peer | Guest teaching | Guest disagreement | Siddhartha pushing back | Why |
|---|---|---|---|---|---|---|
| Anand Chandrasekaran's Career Journey to Five9 | 2 | 1 | 0 | 0 | Siddhartha provides a welcoming, standard interview prompt asking Anand to walk through his career transition from Facebook to Five9. Anand responds collaboratively with a comprehensive overview of his background. | |
| Five9's Growth, SaaS Dynamics, and Strategic Acquisitions | 4 | 2 | 0 | 0 | Siddhartha demonstrates solid sector research by bringing up Five9's ARR metrics, decacorn status, and specific recent acquisitions (Vendoo and Virtual Observer). Anand elaborates on SaaS dynamics and market penetration. | |
| Leading Digital Transformations at Bharti Airtel and Snapdeal | 2 | 1 | 0 | 0 | Siddhartha asks an open exploratory question regarding Anand's stint in India at Airtel and Snapdeal. Anand delivers an expansive narrative on pre-empting Reliance Jio and launching early digital products. | |
| Angel Investing Thesis and High-Growth Indian Startups | 3 | 3 | 0 | 0 | Siddhartha prompts Anand to detail his early-stage angel investments in breakout companies. Anand provides an in-depth breakdown of his investment thesis across Rupeak, NoBroker, and Khatabook. | |
| Angel Exits, Regulatory Friction, and Startup Failure Modes | 3 | 2 | 0 | 0 | Siddhartha probes into both portfolio exits and startup failure modes. Anand discusses friction in Indian M&A paperwork and outlines the two primary causes of startup failure: premature scaling before PMF and team chemistry issues. | |
| Crisis Management: Employee Support and Building Windmills | 3 | 4 | 1 | 1 | Siddhartha suggests startups fail during downturns due to capital scarcity, but Anand reframes the premise, arguing capital follows deserving companies and that crises reveal character rather than change it. | |
| Leadership Lessons from Tech Visionaries and Operational Practices | 2 | 3 | 0 | 0 | Siddhartha asks about common management takeaways from working under top tech leaders. Anand provides masterclass insights on corporate values as real trade-offs and weekly priority alignment. | |
| Timeless Product Management Principles and Decision-Making | 2 | 3 | 0 | 0 | Siddhartha prompts Anand for enduring product principles during turbulent times. Anand details solving critical pain points elegantly, managing speed versus alignment, and Keith Raboy's 70% conviction rule. | |
| Advice for Angel Investors: Power Laws, Compounding, and Exits | 5 | 3 | 1 | 4 | Siddhartha provides direct pushback to Anand's advice on holding investments long-term by citing the real-world Giphy acquisition where early angels were diluted by late-stage VC preferences. Anand concedes secondary nuance while reinforcing power law dynamics. |
Statements from this episode (18)
Consumer DNA is accelerating enterprise SaaS product development cycles
“There is an interesting trend going on and Slack and Zoom et cetera, part of that trend where there is a increasing movement of a consumer DNA into SAS products where the cycles are becoming shorter. There's more iterative product development. More integration…”
Chandrasekaran: Customer care beat commerce and content on Facebook Messenger
“Of all the use cases that we started working on, ranging from content to commerce to customer care, ah, the customer care focus, ah, had the most traction”
Chandrasekaran: Five9 achieves an LTV to CAC ratio of approximately 6
“And so that's sort of so Five Nines LTV over CAC is about six over a period of time.”
Chandrasekaran: Only 10% to 15% of contact centers have migrated to cloud
“In terms of the percentage of this industry that has penetrated and moved to the cloud it's about 10 to 15%. So there's still over 80, 90% that is yet to move to the cloud.”
Chandrasekaran: Bharti Airtel built digital products in 2014 to preempt Jio
“Airtel was, ah, had, had sort of, ah, seen, ah, the coming of Jio, ah, in a few years, ah, and so in 2014 started to kind of preempt that and started to build out products, ah, and bring someone on board who had, ah probably never been at a telco, but I'd buil…”
Chandrasekaran: Snapdeal and Freecharge were too early with e-commerce payments model
“So today, if you look at what PhonePay is doing inside of Flipkart definitely that model has proven to be true, but we were also a little bit early we tried to do it in 2016, 20 17, that time frame.”
Chandrasekaran: Over 95% of India's gold remains unleveraged
“Like, for instance, the gold loan market, again only six percent of India's gold is leveraged in some way, right? About over 95% is not leveraged.”
Chandrasekaran: Rupeek delivered a 90x to 100x return for angel investors
“It's been really honored, lucky to have been in the company since 2016, and there, I would say about a 90 to a hundred X return for the angel investors at this point.”
Chandrasekaran: Fynd exited to Reliance for around $50M to $60M
“And for, I think it was like, around like a 50, sixty million dollar exit. And so, you know, all the investors did pretty well.”
Chandrasekaran: Snapdeal cut 70% to 80% of staff over 12-18 months
“It became really hard to kind of right-size the company, and the company's taken, you know, drastic steps reducing, like, 70, 80% of people over a 12 to 18 month period before getting to a place where the company is now doing incredibly well.”
Chandrasekaran: Startups performing well rarely fail simply from capital scarcity
“I've actually I've not found a lot of examples where truly the company was doing well and deserved to raise capital and couldn't raise capital, right? Like, it largely could be traced to, like, either the cost structures or sort of getting ahead of where they …”
Five9 gave cash bonuses to all employees below the director level
“At Five-Nine we actually did something that I'm incredibly proud of, which is we actually gave a sum of money to all the employees in the company below director level for whom that sum of money would make a huge difference when, so we did, like, you know, no, …”
Chandrasekaran: In a crisis, companies should build windmills rather than bunkers
“Obviously you need to conserve cash, you need to sort of get into survival mode but also you don't want to, like, go in a bunker And hide out until everything clears, right? You want to sort of build windmills that actually start leveraging what is going on in…”
Chandrasekaran: Company values must be genuine trade-offs, not platitudes
“One thing that I learned was how values have to be trade-offs, right? So, if you have a value like, oh, you gotta be honest, and you shouldn't cheat people, or something like that, everyone will agree with that, right? There is no Other side of that that is eq…”
Chandrasekaran: Products earn personality only after solving pain points elegantly
“Find a huge A problem statement that's a pain point for your consumers or your business users you know, come up with an elegant solution, and then once you've done one and two, you earn the right to introduce a twist or a personality of your own.”
Chandrasekaran: Investors Make Money on Successes but Reputations on Failures
“As they say you make your money with your successes, but you make your reputation with the failures, right? So honestly, I would say the question I would ask is, if you went through an experience where the founder didn't do well would that founder work with yo…”
Chandrasekaran: Selling Breakout Startups Early Is One of the Worst Angel Moves
“So I've heard a lot of angel investors who are patient for two, three, four years, and then like exit soon as the company breaks out, right? And I would say this is probably one of the worse things you can do for yourself. And you know, if you sort of look at …”