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  1. All-In with Chamath, Jason, Sacks & Friedberg
  2. How Orlando Bravo Built One of the Most Successful Firms in Private Equity
How Orlando Bravo Built One of the Most Successful Firms in Private Equity

How Orlando Bravo Built One of the Most Successful Firms in Private Equity

All-In with Chamath, Jason, Sacks & Friedberg · Oct 15, 2025

Thoma Bravo's Orlando Bravo reveals his PE playbook: disciplined software focus, operational excellence, and the power of mentorship.

Thoma Bravo Stays Small to Go Big, Capping Its Team to Ensure Mentorship

By intentionally limiting its team size to around 230 people, the firm ensures senior partners can provide deep mentorship to the next generation. This structure prevents the team from becoming internally focused and keeps them hunting for deals, which are "not in the office."

How Orlando Bravo Built One of the Most Successful Firms in Private Equity thumbnail

How Orlando Bravo Built One of the Most Successful Firms in Private Equity

All-In with Chamath, Jason, Sacks & Friedberg·4 months ago

A Software Company's Gross Margin on Customer Support Is the Best Proxy for Its Product Quality

During due diligence, analyzing support cost margins is a powerful heuristic. A company can claim to have a great product, but if its gross margins on support are low, it reveals underlying flaws. The goal should be to improve the product to "eliminate the reason for the call altogether."

How Orlando Bravo Built One of the Most Successful Firms in Private Equity thumbnail

How Orlando Bravo Built One of the Most Successful Firms in Private Equity

All-In with Chamath, Jason, Sacks & Friedberg·4 months ago

Thoma Bravo's Founder Attributes His Success to Listening, Not Creating Anything New

Contrary to the typical founder narrative of invention, Orlando Bravo emphasizes that his career was built on execution and disciplined learning. He actively listened to his mentors, absorbing their playbooks rather than trying to invent his own, suggesting apprenticeship can be a faster path to success.

How Orlando Bravo Built One of the Most Successful Firms in Private Equity thumbnail

How Orlando Bravo Built One of the Most Successful Firms in Private Equity

All-In with Chamath, Jason, Sacks & Friedberg·4 months ago

Mega-PE Deals Start "50% in the Hole" Due to Exit Valuation Math

To generate returns on a $10B acquisition, a PE firm needs a $25B exit, which often means an IPO. They must underwrite this IPO at a discount to public comps, despite having paid a 30% premium to acquire the company, creating a significant initial value gap to overcome from day one.

How Orlando Bravo Built One of the Most Successful Firms in Private Equity thumbnail

How Orlando Bravo Built One of the Most Successful Firms in Private Equity

All-In with Chamath, Jason, Sacks & Friedberg·4 months ago

Modern PE Returns in Tech Come from Growth, Not Financial Engineering

The old PE model is obsolete in software. With high revenue multiples (7-8x) and low leverage (30% debt), firms must genuinely grow the business to generate returns. About two-thirds of value now comes from selling a larger, more profitable company (terminal value), not from stripping cash flow.

How Orlando Bravo Built One of the Most Successful Firms in Private Equity thumbnail

How Orlando Bravo Built One of the Most Successful Firms in Private Equity

All-In with Chamath, Jason, Sacks & Friedberg·4 months ago

Private Equity Giant Thoma Bravo Turns Tech Innovators Profitable by Immediately Cutting 15% of Costs

The firm's playbook involves an immediate, one-time cost reduction at closing to establish a baseline of profitability. This allows them to shift the company's valuation from a revenue multiple to a more stable EBITDA multiple, creating value without disrupting long-term growth initiatives and shocking employees later.

How Orlando Bravo Built One of the Most Successful Firms in Private Equity thumbnail

How Orlando Bravo Built One of the Most Successful Firms in Private Equity

All-In with Chamath, Jason, Sacks & Friedberg·4 months ago