You're stuck.
Your devs keep missing deadlines. Your competitor shipped the same feature in 3 weeks. You're thinking about a rewrite. Someone on Reddit said "just use microservices." You have 3 engineers.
You need to talk to someone who's seen this before.
CTOConnect / Founding Cohort
Live CTO-level thinking without hiring one.
Monthly live office hours. Small group. 27 years of pattern recognition across Fortune 500s and startups.
Bring your specific problem. Get a specific answer. In real time, with people who get it.
Seats are intentionally limited.
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.
"I'm shipping fast with AI but I have no idea if I'm building a house of cards."
You're a founder or small team. No senior dev. No CTO.
AI writes most of your code. It works. Mostly.
But you don't know what you don't know. Is this architecture going to scale? Are there security holes? Will this fall apart when you get real traffic?
You're moving fast, but you're also flying blind.
→ You don't need to slow down. You need someone who's seen what breaks at scale. I'll tell you which shortcuts are fine and which ones will cost you 6 months later.
How It Works
Monthly 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 so members can revisit discussions or catch up if they miss one.
The collection grows over time as the group builds momentum.
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're the technical decision-maker but you don't have a technical peer to pressure-test ideas with.
You're a non-technical founder making technical bets with real money and no safety net.
You're a freelancer or agency owner scoping projects and quoting timelines you're not 100% sure about.
You're a first-time engineering lead figuring out how to manage people, process, and architecture all at once.
You're a small team (2-5 devs) moving fast and making decisions that will compound over the next 12 months.
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)
And to be clear about what this is:
This is not a Slack channel with 24/7 access. Not daily project management. Not tactical hand-holding on every ticket.
This is structured strategic thinking time. Twice a month. Live.
Your Situation Is Specific
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.
Reddit and AI give you unproven theory. You need answers for YOUR situation.
Not one-size-fits-all advice. Real answers for your specific problem.
Simple Pricing
CTOConnect Office Hours
$99/month
- Monthly live sessions (bring real problems)
- Email access between sessions
- Recorded sessions (members-only)
- No commitment. Cancel anytime.
30-day free trial. If it's not worth it, cancel anytime. 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.
CTO-level guidance for the price of a SaaS subscription.
I've Seen These Decisions Blow Up
Monolith or microservices?
Rewrite or refactor?
Fire the dev or fix the process?
Is this hire actually senior?
Let me help you skip the hard lessons.
I've seen $50M rewrites that never shipped. Teams paralyzed by "senior" hires who made everything worse. Startups that scaled their architecture before finding customers. Enterprises that moved so slow they got eaten by competitors.
27 years. Built and sold a SaaS. Still run production systems. I know what breaks.
What I help with:
- Should you rewrite this? (Usually no)
- Are your devs the problem? (Usually not the only problem)
- Is this hire actually good? How do you tell?
- 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?
Your next big decision doesn't have to be a guess. Real people. Real answers. No bullshit.
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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