You're stuck.
Your devs keep missing deadlines.
You've been waiting 2 months for a feature that should take 2 weeks. Your competitor shipped it in 3 weeks. You're losing customers to them.
You're thinking about a rewrite.
You told the team "6 months." They said "doable." It's been 8 months. You're not halfway done. You haven't shipped a real feature in a year. Revenue is flat.
You hired a "senior" dev who said they knew what they were doing.
Three months in, you realize they're a mid-level dev with confidence. You're paying $150K/year. They've shipped one feature. It broke production twice.
Someone on Reddit said "just use microservices."
You have 3 engineers. You're barely keeping the monolith running. Now they want to split it into 12 services. You have no idea if this will help or kill you.
Your tech stack is held together with duct tape.
Every new feature breaks 3 old ones. You're afraid to touch anything. New hires take one look at the codebase and quit. You're embarrassed to show it to anyone.
Talk to someone who's seen this before.
Bi-weekly office hours. 27 years of pattern recognition.
Fortune 500s to startups. I've seen what works at every scale.
Bring your specific problem. Get a specific answer.
$99/month.
Sound Familiar?
"Should we rewrite this app?"
You're embarrassed to show the codebase to new hires.
The last three developers took one look and declined the offer.
Every feature now takes 3x longer than a year ago.
You're spending $200K/year just keeping the lights on. No new features. Just fixing what breaks.
→ Probably not. Rewrites take 3x longer than you think and kill momentum. I've rescued teams from $50M failed rewrites. Let me show you what to do instead.
"My devs aren't fast enough."
You've been waiting 2 months for a feature that should take 2 weeks.
Your competitor shipped the same thing in 3 weeks.
You're losing 5-10 customers per month to them.
That's $50K-$100K in annual recurring revenue. Gone. Because you're slow.
→ Could be the devs. Could be the process. Could be the features are too big. Usually it's all three. Let's diagnose which one is actually killing you.
"I need to present architecture to a client on Friday."
You're not 100% sure your proposed solution will actually work at scale.
You promised them 10,000 concurrent users. You've never built anything past 500.
If you're wrong, you'll spend the next 6 months fixing it. Or lose the client. Maybe both.
→ Let's make sure you're not promising something you can't deliver. I've built systems at every scale. Let me tell you what actually works.
"Our system is a mess and I don't know where to start."
Technical debt is compounding faster than you can ship features.
You have 47 things on the "we should fix this" list. You don't know which ones actually matter.
Every "quick fix" makes things worse. You're paralyzed.
Your best developer just told you they're looking for other jobs. Because the codebase is "depressing."
→ Most messes grow from 2-3 early decisions. Let's find them and fix the root cause. Not all 47 things. Just the 2 that matter.
"AI is making us ship faster but everything feels fragile."
You're generating code 10x faster.
But you're also creating technical debt 10x faster.
Last week an AI-generated feature took down production for 4 hours. It looked fine in code review.
You have a sinking feeling this will bite you in 6 months. But you can't slow down now.
→ AI generates code fast. But it doesn't know which shortcuts will bite you later. I do. Let's keep the speed, lose the time bombs.
How It Works
Bi-Weekly Live Office Hours
Bring your real problems. Should we rewrite this? Are my devs the issue or is it the process? What's the right architecture here? Is this a good hire?
Real answers. Clear next steps.
Email Access Between Sessions
Need a quick "am I about to screw this up?" check? Email me.
I respond with real answers, not canned bullshit.
Recorded Sessions (Members Only)
Every session is recorded, transcribed, and searchable.
Miss a session? No problem. The library grows every two weeks.
Real Answers, Honest Process
You bring the questions. We work through them together.
Time and money are always the constraints. Whether production is down or you have three months to build it right, we'll find the approach that fits.
This Is For You If:
You wake up at 3 AM wondering if you're making the right technical decisions. And there's no one to ask.
You've been waiting 3 months for a feature that should take 3 weeks and nobody can tell you why. Not even the devs.
You're about to commit to a 6-month rewrite and you have a sinking feeling it's the wrong move. But everyone says "the codebase is too messy to fix."
You hired a "senior" dev who turned out to be a mid-level dev with confidence. Now you're stuck with them for 3 more months and they're actively making things worse.
You're a freelancer presenting architecture to a client and you're not 100% sure you know what you're doing. If you're wrong, you lose the client.
You keep missing deadlines and you can't figure out if it's the devs, the process, or you. Everyone blames everyone else.
You're a solo founder or small team (2-5 devs) making architectural decisions with no one to ask. Google gives you theory. You need answers.
This Is NOT For You If:
You want someone to do the work for you
You're looking for hot takes and LinkedIn guru energy
You're a Fortune 500 company (call me for consulting rates)
What You Get
You can't Google this. Every situation is different.
What worked for Google doesn't work for your 5-person team.
What worked for a startup doesn't work at enterprise scale.
Reddit gives you theory. You need answers for YOUR specific situation.
That's what you get here.
I've spent 27 years building software at every scale:
- Fortune 500s: Where process matters and scale kills you
- Startups: Where speed beats perfection and tech debt is a feature
- Military: Where security isn't optional and downtime costs lives
- Hedge funds: Where correctness under pressure is everything
- SaaS: Where uptime is revenue and outages are existential
I've seen what works. And what doesn't.
I've rescued teams from every expensive mistake. So you can avoid them.
Different Problems Need Different Answers
Your 2-person team doesn't need microservices. You need to ship faster.
Your enterprise team doesn't need "move fast and break things." You need process that doesn't slow you to a crawl.
Your struggling startup doesn't need perfect architecture. You need to survive until you find product-market fit.
I help you figure out what works for YOUR situation.
Not one-size-fits-all advice. Not LinkedIn hot takes. Real answers for your specific problem.
AI generates code. You still need judgment.
AI can rewrite your codebase in an afternoon.
But AI can't:
- Tell you if a rewrite is even necessary
- Predict which shortcuts will break in year 3
- Know if your architecture will scale
- Understand the consequences of today's decisions
- Judge whether you're solving the right problem
AI accelerates output. It also accelerates mess.
Generating code is easy now. Making good architectural decisions is still hard.
Code is cheap. The wrong decision costs you 6 months and $200K.
AI helps you ship faster. I help you ship the right things.
Simple Pricing
CTOConnect Office Hours
$99/month
- Bi-weekly live sessions (bring real problems)
- Email access between sessions
- Recorded sessions (searchable, members-only)
- No commitment. Cancel anytime.
30-day money-back guarantee. If it's not worth it, you get your money back. No questions.
Need More?
Deep Dive Session: $600
90-minute 1:1 private session to work through a specific architectural decision, hiring decision, or problem.
Fractional CTO: Starting at $2,000/month
Ongoing guidance, architecture reviews, team integration.
Compare:
- Fractional CTO: $2K–$5K/month
- One-time consulting: $600–$10K
- Winging it alone: Free (until it costs you $500K or more)
This is CTO-level guidance for the price of a SaaS subscription.
Don't Waste Your Time and Money Getting These Wrong
Monolith or microservices?
Rewrite or refactor?
Fire the dev or fix the process?
Get it wrong and you'll waste 6 months and $200K fixing it.
You can't Google this. Every situation is different.
What worked for Google doesn't work for your 5-person team. What worked for a startup doesn't work at enterprise scale.
You need someone who's seen YOUR situation before.
I've been building software for 27 years.
Built and sold a SaaS. Still run production systems.
Consulted on and off for 20+ years.
I've seen every way a technical decision can blow up.
I don't have all the answers, but I've probably seen your situation before.
Let me help you avoid the expensive mistakes I've seen.
What I help with:
- Should you rewrite this? (Usually no)
- Are your devs the problem? (Usually not the only problem)
- How do you break down features that actually ship?
- What's the quickest fix vs the ideal solution vs the practical middle ground?
- Where should AI generate vs where should humans maintain?
I've learned what works. Let me help you skip the hard lessons.
What People Say
"His insights were invaluable, providing me with the confidence and peace of mind I needed to move forward. I highly recommend Kyle..."
Julien de Bats
Startup Founder
"Kyle's advice is extremely valuable... We were lost and needed someone to tell us exactly where we can improve our process without fluffing things up... Kyle did exactly that..."
Meddy Ali
Tech Lead
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