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Colossus (Invest Like the Best / Business Breakdowns)Podcast13 Mar 2020Source: traffic.libsyn.comHost: Patrick O'Shaughnessy

Bill Gurley and Chetan Puttagunta – An Update on Consumer & Enterprise Venture Capital - [Invest Like the Best, EP.162]

In plain words

This piece shares insights from two venture capital experts on how startups can survive a crisis like COVID-19. They argue small companies have an edge because they're flexible and have low fixed costs. The key advice: cut costs decisively, hoard cash, and don't expect a quick recovery. Examples include OpenTable surviving the 2001 dot-com bust while rivals failed, Zappos founder negotiating longer payment terms with suppliers, and Zoom seeing its stock rise during the pandemic.

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At a Glance Benchmark Capital partners Bill Gurley and Chetan Puttagunta, in an episode of Invest Like the Best, discussed the impact of the COVID-19 pandemic on the early-stage venture capital ecosystem. Their core argument is that during a crisis, small startups gain an advantage due to their flex

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Deep Analysis

Bill Gurley and Chetan Puttagunta – An Update on Consumer & Enterprise Venture Capital - [Invest Like the Best, EP.162]

At a Glance

Benchmark Capital partners Bill Gurley and Chetan Puttagunta recorded this episode on March 12, 2020 (during a sharp decline in U.S. equities), discussing the impact of the COVID-19 pandemic on the early-stage venture capital ecosystem. Core thesis: In a crisis, small startups gain an advantage due to their flexibility and low fixed costs. Experience from 2009 shows that outstanding entrepreneurs can rise amid adversity, but the return of risk will be far slower than its retreat.


Risk Cycles in a Crisis: Slow to Accumulate, Quick to Dissipate

Bill Gurley argues that risk accumulation in Silicon Valley is a slow, continuous process, but risk dissipation happens in an instant.

  • Over the past decade, risk appetite has steadily increased, and capital has become easily accessible, leading individuals who might have otherwise stayed in banking or consulting to start their own businesses—"because it seemed easy."
  • When risk dissipates, the only entrepreneurs left are those "who are naturally inclined to choose entrepreneurship as a lifestyle, rather than those looking to make quick money."
  • The result: deal volume declines, but deal quality improves.

Chetan Puttagunta adds a key lesson from 2009: the return of risk is far slower than anticipated.

  • After the market bottomed in March 2009, there was a widespread expectation of a "double-dip recovery," so capital returned very slowly.
  • Two of his clients (a semiconductor equipment company and a hardware company) both made the same mistake: they always assumed "things would return to normal quickly," but the actual recovery time far exceeded all models and scenario assumptions.
  • "Risk dissipates extremely fast, but its return is gradual, unpredictable, and may come in 'fits and starts.'"

Structural Advantages of Small Startups

Chetan Puttagunta argues that small size itself is a core advantage during a crisis.

  • If a company with $1 billion in revenue faces a 10% shock, the impact is enormous; but if a company with $1 million in revenue faces the same proportional shock, it is entirely manageable.
  • Small businesses can use a crisis to restructure customer relationships: eliminate "loss-making customers" who never truly valued the product, and double down on core customers who use the product deeply.
  • Historical data shows that the early explosive growth in net retention for top enterprise software companies often stems not from expanding the customer base, but from "building deeper relationships during a crisis and embedding more deeply into customer workflows."

Bill Gurley added the case of OpenTable:

  • In 2001, OpenTable had two venture-backed competitors, but both went bankrupt—because they failed to "be frugal and stay alive."
  • OpenTable survived by "slimming down" and "threading the needle," ultimately reaping huge rewards from network effects. But "in any version of the OpenTable success story, no one reads about those two companies going under—but that's the reality."

Enterprise Software vs. Consumer: Different Nature of Impact

Bill Gurley points out that consumer-facing companies are hit harder and more directly than enterprise software firms.

  • "Wall Street has reacted quickly: Zoom is up, airline stocks are down. Consumer stocks are falling more severely than enterprise software."
  • If a company is forced to shut down for 45 days, will it reset all its SaaS contracts? Most likely not. But consumer companies (e.g., travel platforms) see an immediate revenue hit and may need more decisive action, including layoffs.

Chetan Puttagunta, drawing on enterprise software experience from 2008–2009, highlights three key changes:

1. Extended sales cycles: Enterprise customers will make decisions more slowly.

2. Limited impact on renewal rates: Customers will not immediately switch tech stacks due to the macro environment.

3. Changes in cash flow cycles: Days Sales Outstanding (DSO) will significantly lengthen as liquidity tightens across the system.

But crises also present opportunities: When customers request extended payment terms, founders can dig deeper by asking, "What is actually happening in your business today? Is it a revenue issue, a cost issue, or a conversion issue?" — thereby building deeper value-oriented relationships.


Practical Advice for Entrepreneurs

1. Cash is King, Be Decisive with Layoffs

Bill Gurley emphasizes that in private companies, cash is everything.

  • "Never do 5% or 10% layoffs, as they yield no meaningful benefit while subjecting you to all the cultural trauma."
  • If layoffs are necessary, they should be done in one go to "buy months and months of cash runway."

2. Scenario Modeling, Prepare in Advance

Bill Gurley recommends modeling multiple scenarios and developing action plans.

  • "If this crisis lasts six months instead of two, have you modeled it? Do you have a plan?"
  • Making decisions in calm times is far better than being forced to make tough choices quickly.

3. Re-examine Core Business Drivers

Chetan Puttagunta notes that most people operate on "autopilot" during normal times, making simple extrapolations of business assumptions.

  • Now is the time to pause and re-understand core drivers: "If these assumptions shift slightly, how does it affect the entire business?"
  • Use the change in rhythm brought by remote work to rethink the essence of the business.

4. Leverage Crises to Build Deeper Customer Relationships

The case of Tony Hsieh (Zappos):

  • During difficult times, Hsieh directly called shoe suppliers and said, "If you don't extend payment terms from 45 days to 90 days, we will go bankrupt."
  • He succeeded. Bill Gurley commented: "Everyone thought it was a hard constraint, but he pushed boundaries during tough times, securing massive cash flow and inventory advantages for the company."

Remote Work: Culture Matters More Than Tools

Chetan Puttagunta argues that the core of remote work is not software tools, but company culture.

  • Asynchronous communication becomes key: Companies like Elastic, which have been remote from day one, have long learned to "write things down"—enabling teams to consume daily activities asynchronously.
  • Transparency becomes more important: How to distribute daily goals and KPIs across the entire team requires a redesign.
  • Organizational methods need systematization: In agile development, practices like daily stand-ups require more careful planning in a remote environment—the entire week's plan should be set by Monday morning, allowing the team to organize each day around predetermined activities.

Investment Theme: Capital Efficiency & Product Investment

Chetan Puttagunta believes the following types of companies will benefit during the crisis:

  • Companies with high capital efficiency that do not require significant resources to get started
  • Products that are easy to install and can quickly generate value for customers
  • Companies that have made substantial product investments in online distribution (one of his board member's companies has seen sales data over the past two weeks that "makes it hard to infer anything is happening in the macro world")

However, he warns: Do not start a new company just to chase the current environment.

  • "The companies benefiting now were founded eight years ago, not those reacting now."
  • "This environment will not last forever."

Mentioned Positions

Position Analyst View Key Data
OpenTable Positive Case (Historical) Two competitors went bankrupt in 2001; OpenTable survived through careful cost management
Zappos Positive Case (Historical) Tony Hsieh extended payment terms from 45 days to 90 days
Zoom Positive Mention (Public Market) Stock price rose during the crisis; service remained operational
Elastic Positive Mention (Remote Work Benchmark) Remote-first company from day one; mature asynchronous communication culture
Airbnb Mentioned but not deeply analyzed Cited as a case of a late-stage private company potentially severely impacted

Judgments Worth Remembering

1. Bill Gurley: Risk accumulates slowly and dissipates extremely quickly. "In Silicon Valley, risk accumulates very slowly and builds up continuously. Then, when a reset occurs, risk vanishes instantly. You can have a 10-year period of rising risk, and then the risk disappears."

2. Bill Gurley: The quality of entrepreneurs is actually higher during a crisis. "During a period of rising risk, the average quality of entrepreneurs who secure funding declines. When risk dissipates, the only entrepreneurs left are those who inherently choose entrepreneurship as a way of life."

3. Chetan Puttagunta: Small businesses have a structural advantage. "If a company with $1 billion in revenue suffers a 10% shock, the impact is enormous; but if a company with $1 million in revenue suffers the same proportional shock, it is entirely manageable."

4. Bill Gurley: Never do a 5% or 10% layoff. "It won't yield any meaningful benefit, yet it will put you through all the painful cultural trauma. If you must cut staff, cut enough in one go to buy several months of cash runway."

5. Chetan Puttagunta: The return of risk is far slower than expected. "After the market bottomed in March 2009, there was a widespread expectation of a 'double-dip recovery,' so the return of capital was very slow. The recovery was gradual, unpredictable, and likely to occur in 'fits and starts.'"

6. Bill Gurley: Late-stage private companies are more fragile than public companies in a crisis. "The cap tables of private companies are designed only to go up. When a down round is needed, mechanisms like anti-dilution clauses make things extremely complicated. An IPO unlocks all that complexity, converting everyone into common stock. Even the largest FANG stocks have historically experienced drops of 40-50% — but as public companies, that is not the end of the world."

7. Chetan Puttagunta: The core of remote work is not the tools, but the culture. "Asynchronous communication becomes key. Write things down so the team can consume daily activities asynchronously. Transparency becomes even more important."

8. Bill Gurley: In times of fear, ask yourself 'what greed means.' "Tony Hsieh improved his competitive position during a difficult period by changing business terms. If a company has more capital than its competitors, it can push more aggressively during this window, while others are forced to pull back."