Chime’s Planned IPO, Venture Liquidity and the Rippling–Deel Dispute

Harry Stebbings and investors Rory O’Driscoll and Jason Lemkin discuss Chime's proposed IPO, late-stage funding, a disputed lawsuit between Rippling and Deel, and AI software competition.

Stebbings cites figures from Chime's IPO filing, including 8.6 million active users and $1.67 billion in 2024 revenue. The panel is discussing a planned offering in May 2025, not a completed IPO or a current valuation.

O’Driscoll interprets the filing's timing in light of a sharp market rebound. He says keeping the company prepared gave it the option to proceed; he does not claim inside knowledge of its decision.

He describes Chime's digital model and debit-card revenue, saying lower physical distribution costs can support a different product from a traditional bank. Revenue and customer economics are the panel's reading of the filing.

O’Driscoll discusses debit interchange rules and Chime's relationships with smaller partner banks. He sees potential regulatory sensitivity in the business model; the discussion is a simplified interpretation, not legal advice or a prediction of a rule change.

The guests ask whether other large private companies should consider listing. O’Driscoll says Chime's substantial revenue scale should not be confused with the circumstances of a smaller private company.

They compare Chime's reported prior $25 billion private valuation with lower potential IPO valuations. These are estimates made before pricing, not the eventual offering value.

O’Driscoll explains that the treatment of a late-stage preferred investor can depend on conversion provisions and any price protection. He says the filing did not make the relevant term clear to him; the panel does not establish Chime's actual investor protections.

Stebbings says some late-stage investors commonly negotiate protections, but the guests cannot infer the terms of this particular round from that experience. Any illustration of a ratchet is conditional.

Lemkin argues a founder can rationally accept price protection in exchange for needed capital, even though an adjustment may dilute earlier shareholders. O’Driscoll agrees that the size of the effect depends on the negotiated terms.

They work through a hypothetical where extra shares are issued after a lower IPO price. The resulting dilution, offering pop and investor return are examples, not calculations of Chime's actual outcome.

The panel distinguishes an investment multiple from an annualized internal rate of return. An investor who avoids a loss but waits years for liquidity may still earn a weak annualized return.

O’Driscoll thinks more large companies should consider public markets but says one planned offering does not mean every smaller company is ready. He contrasts the financing needs of lenders with those of fast-growing companies able to raise private capital.

The guests discuss Klarna's financing needs and growth as they understood them at the time. They present their figures and estimates as part of an investment discussion, not audited comparisons.

Lemkin relays an investor's view that some mature private companies should sell or list. He presents it as one limited partner's opinion, not evidence that all companies face the same optimal choice.

Stebbings asks how predictions of a quiet acquisition market fit with AI-related deals. O’Driscoll separates strategic purchases by technology companies from private-equity buyouts and says broad forecasts are uncertain.

Lemkin describes two portfolio companies that received offers around $500 million and declined. The examples reflect his own investment interests and a small sample, not a complete picture of acquisition demand.

O’Driscoll says acquisition appetite can be cyclical: buyers sometimes pay aggressively for strategic assets and at other times have more leverage. He sees preserving companies through slower periods as an important venture task.

Lemkin says a single investment returning the fund may not by itself generate the overall return he seeks. The investors discuss how fund size and portfolio construction change the significance of any one exit.

Stebbings cites an analysis showing larger top-end exits over time. O’Driscoll praises the dataset but says the historical path included a decline before the later rise, so it should not be treated as a straight-line trend.

O’Driscoll argues that staying private longer can allow the strongest companies to compound to larger exit values. Whether current late-stage investors earn sufficient returns depends on future outcomes and entry prices.

The panel asks whether larger potential outcomes justify larger funds. The guests recognize the arithmetic can work for exceptional winners, but the number and value of future exits remain forecasts.

O’Driscoll describes the trade-off in selling a private position: most may not compound dramatically, while a small number of winners can offset many ordinary outcomes. His percentages are an illustrative rule of thumb.

Lemkin says he is considering a rule to sell some seed positions at a stated valuation unless he has strong conviction to hold. It is his personal investment heuristic, not a universal recommendation.

The investors discuss Veeva as an example of the difficulty of deciding whether to distribute shares or continue holding. They distinguish hindsight from what investors could know at the time.

O’Driscoll says a public listing can let limited partners and managers make different decisions about distributed shares. Private holdings can make those choices and the timing of liquidity more difficult.

The panel mentions taxes as one of several reasons managers and investors might prefer different timing. Their comments are personal observations, not an analysis of any individual's tax situation.

Asked what could make public markets more attractive, O’Driscoll suggests voting rights that reward longer holding periods. He also acknowledges the difficulty of reducing pressure from quarterly reporting.

Lemkin asks whether the burden of being public is necessarily overwhelming for a sufficiently large company. O’Driscoll says access to cheaper private capital is a major reason some companies defer listing.

The panel considers OpenAI's organizational structure and possible future changes. The guests offer competing predictions about governance, litigation and ownership; none claims to know a final restructuring.

They speculate about the timing of a future OpenAI model release. Those comments are predictions made in May 2025, not an announcement by the company.

The discussion turns to civil litigation between Rippling and Deel. Lemkin predicts Rippling will prevail and describes allegations as if established; the allegations and counterclaims are disputed, and the panel does not establish liability or a court outcome.

O’Driscoll says he has seen a counterclaim and believes a settlement is possible. His assessment of the filings and predicted result is opinion; Deel's counterclaims are allegations too, not proof of wrongdoing by either side.

Lemkin discusses possible reasons parties bring counterclaims. He explicitly says he is not a litigator; his general assertions about legal strategy and offsets should not be treated as a finding in this case.

Stebbings discloses that he is a Deel shareholder and a friend of its CEO Alex Bouaziz. He says Bouaziz had lived abroad for years, challenging the suggestion that his location reflected flight from the dispute.

The guests express views on whether the companies should settle. Their suggestions are not evidence of a settlement, an admission or the outcome of the litigation.

O’Driscoll raises a hypothetical risk that civil allegations might attract criminal scrutiny, while saying he does not know whether that will happen. The panel does not establish a criminal investigation or charge.

The investors describe litigation's cost and uncertainty and say executives can become emotionally invested in disputes. These are general observations, not legal advice or a judgment about either company's conduct.

Lemkin shares impressions from a SaaStr event, including interest in AI and changing sales and marketing processes. His comments reflect conversations at the event rather than a representative workforce survey.

He reports hearing some executives expect AI to replace parts of their teams; O’Driscoll offers productivity and headcount growth as another possible framing. These are attendees' and speakers' expectations, not verified displacement figures.

Stebbings raises a Microsoft announcement concerning VS Code and its implications for Windsurf and Cursor. O’Driscoll interprets it as evidence of competitive pressure, a market judgment rather than a verified account of Microsoft's motives.

The guests distinguish whether AI sales tools actually work from who captures their value. O’Driscoll says customers and suppliers should agree on measurable success before scaling deployment.

They discuss AI note-taking products and the possibility that a narrow feature becomes commoditized. O’Driscoll points to Gong's broader product expansion as an example of building beyond an initial entry point.

The panel weighs fast-growing products in crowded markets against technically differentiated companies with less current revenue. O’Driscoll says his firm considers both and wants a balanced portfolio.

The guests cite reported Anthropic revenue growth and discuss the high costs of building frontier models. Their figures and projections are unverified in the conversation and do not establish future profitability.

O’Driscoll predicts a small number of foundation-model providers could build enduring businesses. Lemkin is also optimistic, but the number of winners and eventual valuations remain uncertain.

The conversation turns to incumbents and AI agents. Lemkin suggests that if agents interact with stored information, some established applications could become less visible to users; O’Driscoll thinks replacement could take many years.

Asked about Salesforce, O’Driscoll discloses that he owns its stock and says he is not selling. He values its incumbency and cash generation, while acknowledging his view is an investment opinion rather than a guarantee.

The guests thank each other and close the episode.