Ravi Gupta has a presentation for a founder having a terrible day. It comes from Instacart, dates to November 2015, and apparently makes an excellent antidote to the belief that nobody else has ever been in such a mess. He brings out the old board deck and offers the short version: “We came back from this. So can you.”
Most professional biographies preserve the promotions. Gupta preserves the evidence that things once looked awful. A venture investor carrying around an uncomfortable operating memory has something more useful than a reassuring manner: a basis for reassurance. The deck survived its original meeting and acquired a second job.
The route through the grocery aisle
Gupta grew up in Chicago, studied economics at Duke, and entered a professional world that ran through McKinsey and KKR. Technology was unfamiliar territory when he left college. California made it feel like territory worth entering. His career would eventually involve both evaluating companies and working inside one whose daily business was getting groceries to customers.
At KKR, where he worked from 2005 to 2015, he moved through operating and investing roles and became a director. He also helped build its infrastructure investing platform. Then, in 2015, he joined Instacart as CFO. He took on the COO role in 2016, holding both jobs through 2019. The distinction matters: financial responsibility and operational responsibility put different demands on the same person. One measures the business; the other has to make it work.
The career transition makes the old deck more interesting. An investor can examine a problem and recommend a course. An operator must live through the consequences, alongside people who have their own information, limits, and loyalties. Gupta’s subsequent advice repeatedly returns to the difficulty of getting an organization to act on what it already knows.
The whiteboard got smaller
Gupta remembers an Instacart whiteboard with just two words on it: “Unit Economics.” Colleagues went as far as examining county bottle-deposit rules to recover a few cents on an order. The detail is wonderfully unglamorous. A company trying to improve its economics can spend a great deal of time discussing strategy. Here, somebody was reading the local rules about bottles.
In his writing about focus, Gupta recalls desperation as painful and productive. The team’s shared purpose made the work matter at the level of individual decisions. He argues that startups often import elaborate processes before they have established why those processes are needed. His proposed starting point is to identify the single result that would matter most over the coming year, then give the person responsible the means to pursue it.
The bottle story gives that argument a physical scale. A few cents are small enough to overlook from a distance. They become visible when people understand the problem closely. A whiteboard with very little on it can demand a surprising amount from everyone reading it.
Economics
The expensive habit of asking for more people
His hiring argument begins with a boardroom anecdote. A company had cash and wanted guidance on expanding the team. One experienced leader declined to recommend a number because he did not know how many effective managers the business had. That answer impressed Gupta enough to become the premise of an essay.
Managerial capacity, in this view, determines how much hiring an organization can absorb. New employees require direction and context. The people already making the largest contribution deserve attention before a recruiting plan becomes the default solution. Gupta urges leaders to identify those colleagues, understand why they are effective, and make sure they are working on the essential problems.
He also describes how hiring can trigger further hiring: more people to support the sales organization, more planning, more internal coordination. The visible addition of capacity can obscure slower decisions. An organization chart is a very tidy picture of an untidy activity.
This is a distinctive concern for someone who has worked in both finance and operations. Money can authorize expansion. It cannot supply all the judgment needed to make expansion useful. Gupta’s essay keeps asking the reader to look at the actual people behind the plan.
One word makes the question harder
When founders worry about an executive’s performance, Gupta offers a test: “Would you enthusiastically rehire them?” Imagine the job open today, with everything now known about the person available to the decision-maker. The word enthusiastically closes some of the escape routes.
He allows for improvement. If the difficulty can be addressed, the leader should explain what needs to change, work on it with the person, and return to the question after a defined period. If it cannot, he argues for ending the arrangement. The framework places an obligation on the manager to tell the truth.
Gupta recognizes the reasons such conversations get postponed: an important project, a difficult search, other vacancies, the possibility that someone else will leave. Those complications explain the hesitation. They also make it easy for a temporary compromise to become a permanent working relationship.
His writing gives candor a practical purpose. People deserve to know whether their manager would choose them again. The business deserves decisions made with current knowledge. Neither benefits very much from an assessment quietly stored away while everyone behaves as though nothing needs attention.
“Would you enthusiastically rehire them?”Ravi Gupta · a test for executive decisions
Who takes the call?
Gupta joined Sequoia in November 2019. Earlier operating experience followed him into the work of supporting founders. Michael Moritz had provided a model at Instacart: regular calls in which Gupta could discuss what was happening, initially weekly and later every three weeks. He has encouraged founders to find people with whom they can be vulnerable.
A relationship like that has a different rhythm from the formal board meeting. Problems can be spoken about before they have acquired polished language. A person can ask for help while still working out what kind of help is required.
Gupta’s conversation about focus with Patrick O’Shaughnessy in 2022 explored demanding and supportive leadership, motivation, and mentorship. His 2023 appearance with Shane Parrish returned to decisions, quality, and the difference between immediate demands and longer-term priorities. Across these conversations, his subject is often the judgment that precedes the visible decision.
His relationship with Instacart continued after his executive tenure. He advised Fidji Simo as she took on the CEO role, describing her appetite for responsibility in the language of basketball. In September 2023, he joined the company’s board. By August 2025, he was its lead independent director. The grocery chapter had become a continuing association.
A term sheet, delivered by the kids
Basketball also appears in the story of Sequoia’s partnership with Meter. Gupta and Isaiah Boone built a relationship with founders Anil and Sunil Varanasi around both the business and their shared interest in the NBA. The founders got to know Gupta’s sons over Zoom. When Sequoia offered to lead Meter’s Series B, the children were the first to deliver the news.
Meter’s proposition was practical: combine hardware, software, and operations to make business internet easier to set up and run. The relationship around that proposition included memos, reference calls, and conversations over time. Then a financing milestone arrived through a family cameo.
Another connection, with Sierra co-founder Clay Bavor, has its own division of labor. In a conversation they recorded with Pat Grady, Bavor described Gupta as the sports expert while he supplied technical help. Gupta acknowledged calling Bavor when a memo left him puzzled. He also interrupted a discussion of AI-generated avocado chairs to recall that Instacart had owned actual chairs shaped like avocados. The furniture received a less flattering financial review.
The card beside the ambition
Gupta keeps a notecard on his desk saying “Bring Joy.” It came from reading about Steve Kerr’s approach to the Warriors: joy alongside competitiveness. Gupta found the combination close to what he wanted from a culture.
His essay acknowledges that other leaders might choose different values. The important task is to decide which commitments will survive pressure and to be truthful about them. He also admits to a parental contradiction: correcting a child for taking a board-game defeat badly while feeling a trace of pride in the desire to win. Anyone who has tried to teach gracious losing while wanting victory can recognize the predicament.
In September 2024, he launched Glue Guys with Shane Battier and Alex Smith. Their podcast considers leadership and teamwork across sport and business, including the contribution of people who help those around them perform. Gupta’s interest in basketball had found a regular microphone. The desk card and the show share a question about how ambition feels to the people participating in it.
Another turn toward building
By February 2025, Gupta was discussing his essay “AI or Die” on Invest Like the Best. His argument asked business leaders to use AI on substantive work, supply it with context, and reconsider what their organizations could produce. He framed adaptation as a substantial rebuilding exercise.
That essay carries familiar operating concerns into a newer subject: clarity, patience, responsibility, and the relationship between the team and its tools. The technology changes the possibilities. Leaders still have to understand the work and decide what deserves attention.
In December 2025, Gupta began serving as co-CEO of Ithaca Holdco, a private technology company he co-founded. He remains a Sequoia partner. The latest title brings him back to the direct responsibilities of building a company, after years spent helping others do it.
There is a much older founding story in the family. His grandfather moved from India to the United States in 1957, at 35, beginning a migration that changed the lives of the generations after him. Gupta regards him as the founder of the extended family.
The old Instacart deck belongs in that larger picture of a career shaped by departures, commitments, and difficult work. It has already been through one bad meeting. Gupta has found a useful way to give it another appointment.