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Isai Guerrero

Notes from building real systems

Field reports from work I've shipped, mostly for mortgage, home-equity and real-estate teams, plus playbooks you can copy. Today I build CRMs for small and mid-size businesses; see what I can build.

// LATEST
GENERAL · PLAYBOOK · 5 min read ·

What a CRM migration costs a small business, and how long it takes

A CRM migration for a small business starts at $2,500, usually takes 1–6 months depending on size, and costs $50–$300 a month to run afterwards. Here's what drives each number.

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GENERAL · PLAYBOOK · 11 min read ·

Should you leave HubSpot? What it costs, how to get out, and when to stay

What HubSpot costs a 10–30 person team in 2026, why the bill keeps rising, how to get out of the contract, and when staying is the right call.

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GENERAL · THESIS · 20 min read ·

Why 95% of AI projects fail — and why building in-house makes it worse

MIT found 95% of enterprise AI pilots show no P&L impact, and RAND puts AI project failure above 80%. Why the build is the problem, and in-house is worse.

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MORTGAGE · THESIS · 9 min read ·

Mortgage AI got the document work. The judgment is where it's stuck.

Mortgage AI handles document classification (63%) and reading (54%), but only 21% of underwriting decisions. The gap is about trust, not the model.

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BROKERAGES · THESIS · 8 min read ·

Real-estate agents adopted AI. They still won't trust it on a price.

82% of agents use AI (RPR), but 63% name output accuracy as their top concern. Adoption isn't the gap anymore; trust is, and it has to be engineered.

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MORTGAGE · THESIS · 8 min read ·

The AI-lite problem: why most mortgage vendor AI stops at the LOS door

AngelAi's CEO called most lender AI 'AI lite: safe but shallow.' Why mortgage vendor AI stays in chat and lead nurture, away from the loan system.

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HOME EQUITY · THESIS · 8 min read ·

Home Equity Investment is a $4B asset class with no LOS

$4B+ in HEIs were securitized in 2026, yet every operator built its own stack. Hometap, Point, Splitero, Unlock and Unison all built rather than bought.

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HOME EQUITY · FIELD REPORT · 9 min read ·

Anatomy of an HEI eligibility engine: four investor overlays, zero LLMs in the decision

Field report from a multi-program HEI operator: four investor overlays and a sale-leaseback product, run from one settings table, no LLM in the decision.

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GENERAL · THESIS · 6 min read ·

You can't hire a senior AI engineer fast enough — here's the math

Senior AI engineers in 2026 cost $300K–$500K all-in and take six months to land. For a $2–10M revenue operator, that math doesn't work. Here's what does.

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HOME EQUITY · FIELD REPORT · 8 min read ·

How we cut a home equity platform's lead-to-close cycle in half

Field report from a multi-program HEI / HEA / SLB platform. Voice intake, agentic enrichment, eligibility integration. What we shipped, what broke, what stuck.

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GENERAL · PLAYBOOK · 9 min read ·

The 7-specialist review pipeline that keeps AI features from breaking in production

A reusable playbook: seven structured review passes before any AI feature ships. Catches the failures that pilot-stage AI code carries into production.

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