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Case study · 2025–2026
Cashea

US$100M

From repositioning to close. The largest capital raise in Venezuela, in any sector, managed end to end.

US$100MTotal raised
2Rounds closed
9 moPreparation to close
OngoingEngagement status
The situation

Cashea is the largest buy now, pay later platform in Venezuela, a market most global investors know nothing about and many have strong priors against. The business had grown substantially. The story had not kept pace with the business. The financial model was not built to be read by a sophisticated investor, and the data room was not built to survive serious diligence.

A raise of this size, in this market, required a complete rebuild of how the company presented itself before any investor conversation began.

The process

Nine months,
four phases.

This raise was not won in one meeting. It was won by being 1% better at every step: a sharper narrative, a tighter target list, a more disciplined process and a better negotiation. Each task done slightly better compounded into a different outcome.

Q4 2025

Preparation

Before a single investor saw a deck, Oss worked inside Cashea to re-examine the narrative from first principles. The positioning was rebuilt. The financial model was reworked to reflect how the business had matured. A data room was built in close collaboration with the executive team, designed to survive diligence without surprises.

  • Repositioning the narrative
  • Reworking the financial model
  • Building the data room with the Cashea executive team
Q1 2026

Go to market

The process was designed for density and momentum. A shortlist of 30 to 40 funds was mapped for this round specifically. The roadshow ran on a calendar tight enough to create real urgency, and parallel conversations were managed so investors could see the competition without feeling it was manufactured.

  • Investor targeting and fund mapping
  • High-density roadshow
  • Parallel pipeline management
  • Diligence coordination
Q2 2026

Terms and close

Multiple term sheets arrived. The work shifted to negotiation: comparing leads, understanding what each investor brought beyond capital, and composing the right syndicate. Financial and legal diligence ran in parallel with closing the followers. The round closed.

  • Lead investor negotiation
  • Term sheet comparison and selection
  • Financial and legal diligence
  • Syndicate composition and follower close
Now

After the close

Oss stayed after signing. The current work is the investor relations practice: board materials and investor updates that strengthen Cashea's relationship with its new cap table, and the connections and positioning that will make the next raise faster and better priced than this one.

  • Board and investor update preparation
  • Cap table relationship management
  • Preparing the next raise
Cashea on the Nasdaq billboard in Times Square, announcing the US$100M raise
Nasdaq, Times Square · The round, announced
What the work was

Deal making,
end to end.

Oss did not introduce Cashea to investors and collect a fee. The work was to make the company raise-ready: the narrative, the model, the data room, the materials, the targeting, the process, the negotiation and the close.

Cashea had the business. Oss built the infrastructure around it that allowed investors to see what was there, and to pay accordingly.

The engagement did not end at the close. The cap table is an asset, and the next raise is already being prepared.

Correspondence

New engagements are rare, and begin with an introduction from a founder Oss already works with.

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