May 11, 2020 · 28m · neon-show
Deepak Gupta, WEH Ventures on Impact of COVID19 on upcoming Investments & Startups
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In this episode of the Hundred X Entrepreneur Podcast, Deepak Gupta of WEH Ventures shares actionable insights on navigating macroeconomic downturns based on two decades of venture investing across market cycles. He outlines WEH's disciplined investment philosophy, provides crisis survival playbooks for startup founders, and evaluates the resilience of the early-stage tech ecosystem during COVID-19.
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 1.7 Guest teaching 1.2 Guest disagreement 0.1 Siddhartha pushing back 0.1
speaking balance: gold is Siddhartha, purple is the guest (3 minute bins)
Sharpest disagreement ▶ 2:31 Polite correction of venture tenure
Deepak directly rejects Siddhartha's framing that he has been in venture investing for 20 years, clarifying that his actual venture tenure is 12 to 13 years.
Hardest push from Siddhartha ▶ 23:57 Pressing on underperforming portfolio companiesAfter Deepak focuses exclusively on the half of his portfolio experiencing tailwinds, Siddhartha immediately pushes back to ask specifically about the challenges facing the other half.
Biggest teaching moment ▶ 11:15 ETF market penetration analysisDeepak educates the host on passive retail investing dynamics, contrasting US ETF market penetration at 50% with India's growth from 2% to 6%.
Siddhartha holds their own ▶ 20:23 Framing recurring five-year macro disruptionsSiddhartha demonstrates domain awareness by citing the 2016 demonetization shock as evidence of recurring five-year macro cycles impacting startups.
the scores for every segment, with the reasoning behind each
| Chapter | Topic | Siddhartha as informed peer | Guest teaching | Guest disagreement | Siddhartha pushing back | Why |
|---|---|---|---|---|---|---|
| Deepak Gupta's Journey into Venture Capital | 1 | 1 | 0 | 0 | Siddhartha introduces Deepak and asks about his early background in venture investing. Deepak provides a collaborative overview of his career path from the late 90s internet boom to Intel Capital and launching WEH Ventures. | |
| Navigating Past Market Cycles and Notable Exits | 2 | 2 | 1 | 0 | Deepak gently corrects Siddhartha's timeline assertion that he has been in venture for 20 years, clarifying it is around 12 to 13 years. He then shares his past exit track record from downturn investments like Sasken. | |
| Key Learnings and Fundamentals from Intel Capital | 2 | 2 | 0 | 0 | Siddhartha prompts Deepak on lessons from Intel Capital during the 2002 and 2008 downturns. Deepak provides a detailed breakdown of capital allocation discipline and managing through prolonged market declines. | |
| Investment Thesis on Pratilipi, Smallcase, and Clinikk | 2 | 2 | 0 | 0 | Siddhartha inquires about WEH's investment thesis across top portfolio companies. Deepak delivers an extensive overview comparing global macro trends like US ETF penetration with India's emerging vernacular content and fintech markets. | |
| WEH Ventures' Fund Philosophy and Check Sizes | 2 | 1 | 0 | 0 | Siddhartha asks about fund sizing and guidance given to portfolio founders. Deepak outlines his concentrated seed check philosophy and counsels tailwind companies to act semi-aggressively while others preserve runway or evaluate M&A. | |
| Essential Founder Traits for Navigating Uncertainty | 2 | 1 | 0 | 0 | Siddhartha connects cyclical macro disruptions like demonetization to founder adaptability. Deepak articulates the need for founders to balance passion with cold pragmatism and stakeholder transparency during unexpected shocks. | |
| Portfolio Health Check Across Sectors During Lockdown | 2 | 1 | 0 | 1 | When Deepak highlights only the successful half of his portfolio, Siddhartha follows up to ask about the other half. Deepak transparently details how physical consumer brands face severe lockdown delivery constraints while digital products benefit. | |
| Future Outlook for Early-Stage and Series A Investments | 2 | 1 | 0 | 0 | Siddhartha asks about the upcoming funding outlook for early-stage startups. Deepak notes that lower operating costs will extend seed runway and that strong global VC dry powder will maintain deal velocity for top-tier companies. | |
| Podcast Conclusion and Final Remarks | 0 | 0 | 0 | 0 | Siddhartha brings the episode to a cordial close, thanking Deepak for sharing his insights. |
Statements from this episode (13)
Gupta: Investors Should Keep Deploying in Downturns Rather Than Withdrawing
“A downturn is not necessarily a crisis. So, if you can hold your conviction and invest, you should do that. It may be harder to invest at the same rate, and it's probably foolish to do that, but I don't think a complete withdrawal is something that I would pur…”
Gupta: Even Top Founders Flounder in Multi-Year Market Downturns
“If you see the Nasdaq downturn, It was actually quite prolonged. It was for more than two years. And in those kind of downturns, even the best of founders may flounder simply because, you know, it's very hard to sustain a business over two, three years of a do…”
Gupta: The ETF share of the US market has crossed 50%
“The market now in US is 50% in ETFs. They've crossed over.”
Gupta: India's low-cost ETF market grew from 2% to nearly 6%
“At that point also it was a very high percentage, but in India it was only two percent. People were not aware of low cost passive investing. That market has now grown from two percent to almost six percent.”
Gupta: Smallcase Inflows Remained Strong During Early COVID-19 Crash
“Even now, if you see in the COVID situation, the inflows are actually pretty strong. So the Indian retail investor continues to hold forth.”
Deepak Gupta: High-volume seed dealmaking does not yield good companies
“We also do not think that just doing large numbers of deals is the answer to get to good companies.”
Gupta: Startups With Crisis Tailwinds Should Play Offense, Not Just Survive
“So if you are in the tailwind sector, many of our companies are, especially those who have content, or even small case and you have the capital, then you should be, what I call, semi-aggressive. Because if you see the general advice, it is survive. I think sur…”
Gupta: Startups on weaker footing during prolonged crises should pursue M&A
“I would actively urge companies who are slightly in a weaker footing to think through potential M&A possibilities. Because, ah, you know, if raising capital is going to be difficult, and they will lose some competitive advantage during the, if this crisis is s…”
Deepak Gupta: Most VC-Funded Founders in Recent Years Are Under Thirty
“Most of the entrepreneurs that have been funded in the last five years are relatively young, right? On average, sub-thirty.”
Gupta: Crisis Survival Requires Pragmatism That Contradicts The Passion VCs Seek
“When the crisis hits one of the things is to be pragmatic and non-emotional, right? Which is actually a contradictory quality to when we appraise entrepreneurs upfront where we want them to be passionate and all that. But they have to be sort of passionate and…”
Gupta: Half of WEH Ventures Portfolio Outperformed Due to COVID-19 Tailwinds
“I mean, if I look at our portfolio, I would say at least half the companies are actually doing better than maybe they would have if this had not come.”
Gupta: Lower Post-COVID Costs Mean Seed Startups Need $700K, Not $1M
“I think if the companies at seed stage have adequate runway, then that runway should last them longer because the cost of doing business should go down, right? So the cost of hiring will go down. Also rental should go down. So, you know, if you needed a millio…”