Private Markets, Angel and Secondary Investing, Sacra

Sacra

Private Markets, Angel and Secondary Investing

Bringing transparency to private markets so investors, founders, and employees can build on conviction. Sacra delivers deeply researched insights on the private companies shaping tomorrow's markets. By surfacing the data, context, and operator perspective that are missing from private markets today, we help secondary buyers and sellers price equity accurately and unlock liquidity for the people building these businesses.

Private Capital Markets

<ul><li>Sacra estimates that Augment hit $10M in annual revenue run rate in October 2025, reaching profitability within 18 months of launch.</li><li>For issuers, Augment provides a compliance console that allows companies to approve or deny participants, batch-sign transfer documents, and embed custom terms like volume caps or trading blackout periods.</li><li>Augment raised a $12M Series A in October 2025 led by Builders VC, with participation from Neo, Golden Section, E1 Ventures, Corp Capital, and OPCO Ventures.</li></ul>

Sacra estimates that Augment hit $10M in annual revenue run rate in October 2025, reaching profitability within 18 months of launch.For issuers, Augment provides a compliance console that allows companies to approve or deny participants, batch-sign transfer documents, and embed custom terms like volume caps or trading blackout periods.Augment raised a $12M Series A in October 2025 led by Builders VC, with participation from Neo, Golden Section, E1 Ventures, Corp Capital, and OPCO Ventures.

<ul><li>After a 2023-2024 pilot period where enterprises experimented with AI tools under relaxed security policies to avoid falling behind on AI transformation, IT departments are now reasserting control and demanding compliance—creating a compressed window where AI startups must retrofit SSO, audit logging, and directory sync or risk mass churn as renewal cycles hit.</li><li>As AI has collapsed the timeline to going upmarket into the enterprise from 6-7 years to 6-12 months, startups can no longer sequence enterprise features one at a time—SSO first, then audit logging, then fraud detection—throwing tailwinds behind ‘enterprise readiness’ bundles like WorkOS.</li><li>SSO has become ubiquitous across AI startups like Cursor & Perplexity—downmarket from enterprise B2B SaaS—to protect against LLM inference hijacking, which exploits self-serve models that give away output tokens for free, using device fingerprinting and anomalous behavior detection at login rather than just rate limiting at the API layer.</li></ul>

After a 2023-2024 pilot period where enterprises experimented with AI tools under relaxed security policies to avoid falling behind on AI transformation, IT departments are now reasserting control and demanding compliance—creating a compressed window where AI startups must retrofit SSO, audit logging, and directory sync or risk mass churn as renewal cycles hit.As AI has collapsed the timeline to going upmarket into the enterprise from 6-7 years to 6-12 months, startups can no longer sequence enterprise features one at a time—SSO first, then audit logging, then fraud detection—throwing tailwinds behind ‘enterprise readiness’ bundles like WorkOS.SSO has become ubiquitous across AI startups like Cursor & Perplexity—downmarket from enterprise B2B SaaS—to protect against LLM inference hijacking, which exploits self-serve models that give away output tokens for free, using device fingerprinting and anomalous behavior detection at login rather than just rate limiting at the API layer.

Michael Grinich, CEO Of WorkOS, On AI Startups Getting enterprise-ready At Launch

<ul><li>Flatpay raised a $52.2 million (€45 million) Series B in April 2024 led by Dawn Capital.</li><li>Flatpay operates a B2B model targeting brick-and-mortar SMBs with a flat-rate payment processing structure that eliminates monthly fees and setup charges.</li><li>The Series B funding finances entry into additional EU markets, with Flatpay now operating in Denmark, Finland, Germany, Italy, and France.</li></ul>

Flatpay raised a $52.2 million (€45 million) Series B in April 2024 led by Dawn Capital.Flatpay operates a B2B model targeting brick-and-mortar SMBs with a flat-rate payment processing structure that eliminates monthly fees and setup charges.The Series B funding finances entry into additional EU markets, with Flatpay now operating in Denmark, Finland, Germany, Italy, and France.

<ul><li>Sacra estimates that Retool hit $120M in annual recurring revenue (ARR) in October 2025, up from $90M at the end of 2024.</li><li>Retool raised a $45M Series C in July 2022 at a $3.2B valuation, led by Sequoia Capital with participation from notable investors.</li><li>The introduction of Agents and AppGen represents Retool&#39;s expansion into AI-driven business process automation.</li></ul>

Sacra estimates that Retool hit $120M in annual recurring revenue (ARR) in October 2025, up from $90M at the end of 2024.Retool raised a $45M Series C in July 2022 at a $3.2B valuation, led by Sequoia Capital with participation from notable investors.The introduction of Agents and AppGen represents Retool&#39;s expansion into AI-driven business process automation.

Covering IPOs, Healthcare and Technology Stocks

Andrei Zakharov

Equity Bottom-Up

<ul>
<li>BILL Holdings shares have bottomed out near $40 per share after Starboard Value and Elliott Management built large stakes in the American SMB back-office pioneer.</li>
<li>BILL Holding shares significantly underperformed in 2025 with shares down ~44% over the year versus a 21% gain on the Nasdaq.</li>
<li>I see further room for upside on potential launching new intelligent AI agents, partnerships with software providers, disciplined expense management and operating efficiency.</li>
</ul>


BILL Holdings shares have bottomed out near $40 per share after Starboard Value and Elliott Management built large stakes in the American SMB back-office pioneer.
BILL Holding shares significantly underperformed in 2025 with shares down ~44% over the year versus a 21% gain on the Nasdaq.
I see further room for upside on potential launching new intelligent AI agents, partnerships with software providers, disciplined expense management and operating efficiency.


2024 High Conviction Update: BILL Holdings, Starboard Value and Elliott Move In

United States

Stripe, Inc. provides payment software services and solutions. The Company designs and produces software to process online credit and debit card payments. Stripe serves customers worldwide.

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Stripe (0170016D US)

Primer: Augment - 02 Dec 2025

Marketplace and software suite for trading private company shares across brokers and investors

Sacra

Michael Grinich, CEO Of WorkOS, On AI Startups Getting enterprise-ready At Launch

What is WorkOS in short and what inspired you to build it based on your experience co-founding Nylas...

Sacra

Primer: FlatPay - 17 Nov 2025

Payment terminal and POS system for SMBs with flat-rate card transaction fees

Sacra

Primer: Retool - 13 Nov 2025

Tool for developers to build internal apps on top of production data sources

Sacra

2024 High Conviction Update: BILL Holdings, Starboard Value and Elliott Move In

BILL Holdings shares have bottomed out near $40/share. The activist investor Starboard Value and hedge fund Elliott Management move in: a double...

Andrei Zakharov

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52-week Range

Market Cap (USDm)

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Primer: Augment - 02 Dec 2025

Marketplace and software suite for trading private company shares across brokers and investors

Sacra

Michael Grinich, CEO Of WorkOS, On AI Startups Getting enterprise-ready At Launch

What is WorkOS in short and what inspired you to build it based on your experience co-founding Nylas...

Sacra

Primer: FlatPay - 17 Nov 2025

Payment terminal and POS system for SMBs with flat-rate card transaction fees

Sacra

Primer: Retool - 13 Nov 2025

Tool for developers to build internal apps on top of production data sources

Sacra

2024 High Conviction Update: BILL Holdings, Starboard Value and Elliott Move In

​BILL Holdings shares have bottomed out near $40/share. The activist investor Starboard Value and hedge fund Elliott Management move in: a double...

Andrei Zakharov

BILL Holdings shares have bottomed out near $40/share. The activist investor Starboard Value and hedge fund Elliott Management move in: a double...