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AI, Business, cloud

Migrating from Lovable: Steps to Self-Host Your App

Lovable is a remarkable product.
You describe what you want. It builds it. You ship in hours instead of weeks.
That’s genuinely impressive, and I’ve used it to launch things I would have otherwise shelved for “when I have more time.”

But “when I have more time” eventually arrives.

And when it does, you start asking different questions:

“What happens if they change pricing?”
“Can I run this on my own infrastructure?”
“Where exactly does my data live?”

Those aren’t paranoid questions. They’re the right questions.
This post is about answering them — practically, with actual steps you can follow.

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Business

Scaling Engineering: Ownership Over Hiring

Most engineering leaders think scaling is about hiring.

And honestly, that instinct makes sense — more work, more people, problem solved. But in practice, scaling engineering is mostly about scaling ownership. The teams that succeed aren’t necessarily the ones with the most engineers, the most process, or the fanciest org charts. They’re the ones that can keep ownership close to the work as the organization grows.
That sounds simple until you’ve experienced the moment it breaks down at 2 AM.

I’ve had the chance to see engineering organizations at very different scales — from early startup environments to larger companies like Google, Netflix, Meta, and JFrog.
Every company is unique, but the patterns are surprisingly consistent.

The biggest takeaway is this: every growth stage introduces a new coordination tax.
The challenge isn’t eliminating that tax.
The challenge is preventing coordination overhead from growing faster than the company does.

The First 20 Engineers: Optimize for Builders

At around 20 engineers, speed is your biggest advantage, and process is often your biggest enemy.
Everyone sits close to the product. Engineers talk directly to customers.
The person writing the code can usually explain exactly why it exists and what it connects to. It’s a genuinely magical phase — and it’s also temporary, so it’s worth enjoying while it lasts.

At this stage, ownership should be brutally simple: teams own services end-to-end, carry their own on-call rotation, deploy their own code, and fix their own incidents.
No exceptions.
One of the strongest signals of a healthy engineering culture is whether the people building the software also feel the consequences when it breaks. If your team gets paged because their service is down, reliability becomes surprisingly important. Funny how that works.

The Platform Team Trap

One mistake I see repeatedly at this stage is creating a platform team too early.
The logic is completely understandable — someone notices that everybody is independently building CI pipelines, setting up monitoring, and solving the same deployment problems.

The natural reaction is, “we need a platform team.” And you know what?
That instinct isn’t wrong.
It’s just early.

At 20 engineers, the cost of coordination is often higher than the cost of duplication.
A few redundant solutions are cheaper than introducing another organizational boundary and the meetings, hand-offs, and dependency management that come with it. This tradeoff becomes even more relevant in the AI era.

Generating code is now cheap.
Creating clear ownership is still expensive. The bottleneck is no longer writing software — it’s understanding who should maintain it six months from now. That’s a human problem, not a tooling problem.

Around 50 Engineers: The Coordination Tax Arrives

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AI, Business

Building a CMMC Readiness Calculator That People Can Actually Finish

Most compliance tools look great in screenshots.

Far fewer are useful on a random Tuesday afternoon when someone in operations, IT, or leadership is trying to answer a simple question:

“How ready are we, really?”

That’s the problem we set out to solve.

Not certification.
Not auditing.
Not replacing consultants.

Just helping defense contractors get a realistic picture of their CMMC readiness before investing weeks of meetings, spreadsheets, and assessment calls.

The result is a simple CMMC Readiness Calculator that turns a short questionnaire into:

  • an estimated readiness score
  • an estimated SPRS score
  • a count of missing or partially implemented controls
  • a three-year compliance cost projection
  • a comparison between traditional and managed compliance approaches

Nothing magical.
Just useful.

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Futuristic cockpit with holographic compliance and cybersecurity monitoring dashboard
AI, Business

CMMC Certification Cost: How AI-Native Compliance Can Cut Expenses by over 70%

If you’re pursuing CMMC certification, one of the first questions you’ll ask is:

How much does CMMC certification cost?

The answer depends on your current security posture, the size of your organization, and how you approach compliance. For many small and mid-sized businesses, the total cost of achieving and maintaining CMMC Level 2 compliance can range from tens of thousands to hundreds of thousands of dollars.

The surprising part?

The audit itself is rarely the biggest expense.

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AI, Business

AI and Compliance: The Most Boring Billion-Dollar Opportunity Nobody Is Talking About

The US compliance sector is massive, expanding rapidly, and heavily strained.
It represents over $40 billion in annual labor spend with more than 400,000 officers. Despite ballooning teams, compliance work has remained stubbornly manual, bureaucratic, and paper-based (“schlep work”), leading to high employee churn (>20%) and massive backlogs (e.g., TD Bank’s $3B fine over a 70,000-alert backlog).

Here’s a weird data point:
Over the last 20 years, the fastest-growing occupation in the US was manicurists and pedicurists.
Right behind it?
Compliance Officers.

Not AI engineers. Not data scientists. Compliance officers.
That says something important about where the real work has been hiding.

The Problem Nobody Wanted to Solve

Compliance is painful. Bureaucratic. Paper-heavy. Repetitive.

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Modern office building with digital graphic illustrating secure data, verified access, and network integrity
AI, Business

Bridging the Cybersecurity Gap for SMBs

I recently joined the MSP 1337 podcast with Chris Johnson to talk about something I’ve been thinking about for years:

Small and midsize businesses are being asked to operate with enterprise-level security expectations — without enterprise-level resources.

That gap is becoming impossible to ignore.
And AI is accelerating both sides of the problem.

Attackers are moving faster.
Infrastructure is becoming noisier.
Compliance requirements are multiplying.
Meanwhile, SMBs and MSPs are still expected to somehow manage everything with limited staff, fragmented tools, and endless alerts.

That model is cracking.

Btw, you can listen to it here:
– Apple Podcasts
– Spotify

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Home office devices protected by a glowing digital shield blocking cyber attacks
AI, Business

Ransomware Risks: Why SMBs Need AI Security Now

Last week I was staring at my EnduraCoach dashboard, watching it yell at me for sneaking in an extra sprint session that my body wasn’t ready for. The AI caught the overtraining pattern across heart-rate, sleep, and power data and shut it down before I wrecked my Ironman build. That same evening the April ransomware numbers landed. SMBs got hammered again. And I thought: if only every founder had an always-on coach like this for their security stack.

Here’s the uncomfortable truth from April 2026: ransomware didn’t slow down—it accelerated. A new player called JanaWare quietly encrypted files for hundreds of Turkish home users and small businesses through targeted phishing campaigns. Low-dollar demands ($200–$400) but high volume. Attackers are learning that SMBs are softer targets and faster payers.

The broader picture is uglier.
Verizon’s 2025 DBIR (still the gold standard) showed 88% of ransomware breaches hit SMBs versus just 39% for enterprises. Unpatched vulnerabilities caused 29% of incidents; stolen credentials another 30%.
Sophos and Black Kite reports confirm SMBs in the $4M–$8M revenue band are now the sweet spot for attackers.

Most of us simply don’t have a 24/7 SOC or the headcount to patch, triage, and remediate at machine speed.

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Business

Key Lessons from Sorkin’s ‘1929: The Wall Street Crash’

Andrew Ross Sorkin’s book “1929: Inside the Greatest Crash in Wall Street History—and How It Shattered a Nation” (published in 2025) provides a forensic, narrative-driven account of the most famous market collapse in history.
Sorkin, who also wrote the 2008 crisis definitive history Too Big to Fail, focuses on the human psychology, hubris, and technical failures that turned a speculative boom into a generational disaster.

Here are the top 20 takeaways from the book, followed by specific lessons for you as a long-term investor.

1. Euphoria is the market’s most dangerous condition
Pessimism had gone out of fashion by the 1920s. Government commissions, governors, and economists all declared boom-and-bust cycles relics of a vanished age — it was a fatal illusion. When everyone agrees the good times will last forever, that’s when risk is highest.

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Business

Effortless Techmeme Summaries to Slack and Telegram

Every morning starts the same way: open Techmeme, scan headlines, open too many tabs, and somehow end up 20 minutes deep into something you didn’t mean to read.

That loop is the problem. Instead of trying to “summarize the internet” or build another bloated AI dashboard, this project does something much simpler: take a strong source, rank and summarize it, and deliver a clean digest to Slack or Telegram.

That’s it—and that’s why it works.

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AI, Business

Why SMBs Struggle with Cybersecurity: The Real Challenges

I recently had a conversation on The Changelog, and it reinforced something I’ve seen over and over again:

SMB cybersecurity isn’t just hard — it’s structurally broken.

Not because people don’t care.
Not because tools don’t exist.
Because the entire model assumes resources that SMBs simply don’t have.

The uncomfortable truth

Security today is designed for enterprises and downsized for everyone else.
That doesn’t work.
Enterprise model:

  • Dedicated security teams
  • Time to triage alerts
  • Budget to stack tools

SMB reality:

  • One DevOps person wearing five hats
  • Compliance pressure (SOC 2, ISO 27001, CMMC…)
  • A pile of tools that don’t talk to each other

So what happens?

They install more tools…generate more alerts…and end up less certain about their security posture.
That’s the paradox.

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