Helping businesses scale faster | Helped Startups scale to 1M+ ARR | Access top 5% engineering talent in your time zone | Founder & CEO @ Time Technologies LLC
Rory O’Keeffe is redefining the "modern lawyer" for 2026. Our episode is officially live.
Rory went from the courtrooms of Dublin to the boardrooms of London. He’s a commercial/AI lawyer, a fractional GC, and the author of The AI Advantage.
If you’re wondering how AI is actually changing the high-stakes legal world, here are 3 takeaways from our chat:
AI won’t replace you, but a lawyer using AI will. It’s about speed and the ability to trawl mountains of data in seconds. But Rory warns: AI is a "skyscraper built on quicksand." If your data isn't solid, the tool fails.
The "Candidly" Rule. High-stakes negotiations are stressful. Rory’s secret? Humor. If you can’t find a moment of levity during a two-week-long deal, you’re going to burn out before the ink is dry.
Don't chase "Shiny Objects." Most firms are renting expensive SaaS tools they don't need. Rory’s advice: Look at the tools you already have (like Microsoft) and run a "Pilot" before you overhaul your entire workflow.
Rory is a rare voice in this space—grounded, slightly witty, and deeply practical.
Watch/Listen to the full episode here: https://t.co/zQKbUXQ86S
#AI #LegalTech #FutureOfWork #Entrepreneurship #PodcastLaunch
Can a criminal defense background make you a better tech lawyer?
Rory O'Keeffe thinks so.
Before he was navigating global AI deals in London, he was in the courtrooms of Dublin defending clients in high-stakes criminal cases.
I asked him if those worlds ever overlap. His take was a masterclass in transferable skills:
Negotiating from the "back foot": In criminal defense, you rarely have the upper hand. You learn to find a "sliver of hope" when the door is being slammed in your face.
Managing the "difficult" personality: Boardrooms are full of them. Rory learned how to read people when the stakes were much higher than a contract, it makes a multi-million dollar tech deal feel manageable.
Curiosity over Pedigree: Rory didn’t come from a "lawyer family." He built his career on a simple rule:
If I don't know it, I’m going to find out.
We often think a "zigzag" career is a weakness. Rory is proof that it’s actually a superpower for 2026.
My full conversation with the founder of Ramoc Legal drops this Friday, Feb 14th.
Has a "random" past job ever given you an edge in your current career?
#LegalTech #CareerPath #Entrepreneurship #Podcast
Is your Law Firm Digital efforts going to waste?
Are you employed in your own law firm rather than running a business?
Are you spending $50 - $100 a click and getting +60% junk leads?
Are you paying top $$$$ to Multiple SaaS for intake and still non-billable hours increasing?
I’ve mapped out the exact technical roadmap we use to turn law firms into Revenue generating engines.
We have written a handbook, in which you’ll find:
→ How to audit your week and stop setting money on fire with admin tasks.
→ The 5 factors Google uses to decide if you’re invisible or a market leader.
→ How transparency through custom portals reduces clients' anxiety
→ How to glue different SaaS together to work as ONE.
→ PPC vs. SEO: The main differences and use cases
→ How 80% of your admin work should be automated so you can focus on the 20% that actually produces revenue.
Want the full 33-page blueprint for free?
👇 Comment "HANDBOOK" below and I’ll send the link directly to your DMs.
hashtag#LegalTech hashtag#LawFirmGrowth hashtag#Automation hashtag#LegalMarketing hashtag#Scaling
Delete clawdbot aka moltbot asap!
I am not against agentic AI and in fact we build it for law firms with proper guardrails.
But this autonomous agent has huge fundamental flaws that cannot be controlled.
For now I will only inform you one out of many.
Clawdbot is useful only when it has full system access which means it will have control over file system access, terminal access, environment variables.
The biggest threat isn’t that it has all the access of your local computer but from external sources from which it reads.
In AI world there is a term used “prompt injection”.
Let me explain in most simple terms - prompt injection means instructions from the content it reads.
Suppose you have instructed the agent “summarize my email and send reply”
Now some attacker has sent an email telling the agent to send him confidential information or run a command in terminal. The agent will do it.
This means all your information on your local machine like passwords, credit card info etc will be sent.
You might think how is this possible and why would my agent take instructions from a random email.
Don’t take my word but even Sam Altman, CEO of OpenAI has described prompt injection as “significant and structural security risk” that may require a complete new paradigm to fully solve.
Would you trust an agent with your personal computer?
"Checks and balances are disappearing... we cannot normalize third-world problems in America." In this episode of With Immigration Lawyers, host Awais interviews Ms. Jalloh, the founding attorney of Jalloh LLC. Ms. Jalloh shares her deeply personal journey of migrating from Sierra Leone at age 15 after her father sought political asylum following a military coup. She discusses her transition from wanting to be a corporate lawyer for Coca-Cola to finding her true calling in humanitarian and immigration law. Beyond her story, this episode serves as a critical guide for immigrants in 2026. Ms. Jalloh breaks down the "75-country immigrant visa ban," the difference between a travel ban and a case "pause," and the urgent legal protections every immigrant needs to know when dealing with ICE.
https://t.co/6sYqfcaqLr
For growing immigration practices, immigration intake automation allows firms to filter leads faster, reduce staff burnout, improve accuracy, protect client confidentiality, and scale without operational chaos. SaaS tools introduce automation. Custom systems integrate automation into your firm’s logic and workflows. That distinction becomes decisive as complexity grows.
https://t.co/S9BYHo7Da2
Launching a product the right way.
Back in 2025 Q1, Abdullah Masood came to me to discuss an idea for a tutoring marketplace.
Tutoring marketplaces have tough competition due to only one differentiation and that is "we got the top verified tutors".
His idea was to completely keep the platform free, while giving maximum benefits to students and teachers - specifically teachers who currently are being subject to insane amounts of commission fees ranging from 18-83%.
The biggest challenge was to maintain the marketplace as the cost of servers, marketing, admin support and payrolls etc cannot be managed through a free service.
We kept working on his idea and found a solution to keep the marketplace free yet profitable by introducing a freemium model.
Now an idea or an app doesn't automatically proves itself. So before we even built anything, we decided to launch a waitlist - a simple counter till launch and some documentation on how this is a free platform.
Abdullah Masood I think talked to 100s if not 1000s of teachers and students about the platform and people though initially skeptical signed up without the actual product.
Within days there was more than 100 users who signed up and shared their pain of getting ripped off by the existing platforms.
Once we had the market's analysis done, we launched the product as quickly as we could - No fancy UI, No frills.
One the first day of launch 13 teachers and 2 students joined, Abdullah Masood personally emailed/called and talked to them for their input. Every single person joined provided the true feedback that he wanted.
Most dev shops leave the client alone after delivery, but I did not choose that path and made sure that my devs were available 24/7 to make the platform better by user feedback.
20 days later, he had 70+ verified tutors, many signed up for Pro plan and 32+ students. While he has about 400+ teachers in the backend waiting to be verified eagerly and the platform is now making profit.
The lesson we all entrepreneurs must learn is that, do not be afraid to launch a product if you have done enough market research. Initial adopters are those who feel the real pain that you are trying to solve. And if you stick to your vision to "help" ease that pain - your product will work.
#StartupLife
In this powerful second episode, Awais sits down with Attorney Dionnie wynter pfunde to discuss her incredible journey from a teenage mother in Jamaica to a powerhouse immigration lawyer in the United States. Dionne shares the raw reality of her early days in New York, the discipline required to balance law school with motherhood, and the entrepreneurial spirit she inherited from her parents
https://t.co/kKKAqguqcM
This article explores how high-performance UI design influences trust, conversion rates, and lead quality for immigration law firms. It explains why page speed, motion design, and modern frameworks like Next.js and GSAP directly affect client behavior. Through real UX statistics and practical insights, it shows how a high performance law firm website can reduce lead friction, attract higher-value clients, and scale more effectively.
https://t.co/iAecujKCez
This article explores how high-performance UI design influences trust, conversion rates, and lead quality for immigration law firms. It explains why page speed, motion design, and modern frameworks like Next.js and GSAP directly affect client behavior. Through real UX statistics and practical insights, it shows how a high performance law firm website can reduce lead friction, attract higher-value clients, and scale more effectively.
https://t.co/iAecujKCez
Why 2026 is the year we stop "talking" to AI and start "building" with it.
AI adoption in immigration law isn’t slowing down, it’s just getting serious.
For two years, we played with chatbots.
In 2026, high-intake firms (PI, Immigration, Securities) are realizing that 95% of AI SaaS are just "GPT-wrappers", shiny toys that hide old tech.
The Danger: The Knowledge Debt We are entering a cycle of "AI Slop."
1. AI cites authoritative sources.
2. AI hallucinates (15-25% of the time).
3. Humans post that hallucinated content as "expert" advice.
4. AI trains on that human post.
This is a disaster for immigration law where a single wrong citation can ruin a life.
The 2026 Solution: It’s no longer about generic chatbots.
It’s about Sovereign AI: RAG (Retrieval-Augmented Generation): Grounding the AI in your firm’s successful petitions and actual USCIS statutes.
Self-Hosted LLMs: Keeping sensitive client data off the public "Big 7" servers.
Guardrails: Human-in-the-loop systems where the AI is the intern, not the partner.
Don't invest in "AI products." Invest in data infrastructure.
How can I get rich?
In my experience with scaling 3 businesses I believe there are only two ways you can get rich:
1. Get rich quick - which generally requires you to be surrounded with certain types of people and environment where to can get thousand different ideas to scam people.
2. Get rick slow - A more sustainable option which requires to be habitual in taking great actions. Gain a great habit each day e.g introduce yourself to a new person each day.
Note: I used the word "great" and not "good" - because good habits are for ordinary and great habits are for the top 1%. (Good kills growth)
The 'Guaranteed Job' scam is costing students $50k and landing them a 5-year ban from Canada. Even if you are the victim, you are held responsible. Watch the full breakdown on how to spot fake consultants. https://t.co/7SMcMgrBTY
Thinking of using ChatGPT to write your Canada Study Visa SOP? 🛑 Immigration Lawyer Max Chaudhary explains why this is a one-way ticket to rejection. AI knows the website, but it doesn't know the 'Policy Manuals.' https://t.co/7SMcMgrBTY
When does SaaS go from Good to Bad to Ugly for your Law Firm?
THE GOOD
If you run a firm with 1 to 5 people, standard SaaS is your best friend. It’s cheap, reliable, and “good enough.”
Clio Suite (Manage + Grow): ~$169/user
Google Workspace: ~$15/user
QuickBooks Online: ~$35/mo
At this stage, you are paying roughly $220 per user. For a small team, this is a steal. You get enterprise-grade tools for the price of a nice dinner.
THE BAD
You grow to 10+ staff. Suddenly, the "all-in-one" suite feels "master of none." You need specific features that generic tools don't have, like bilingual intake forms or conditional logic for complex immigration cases.
You hit the "Marketplace Fishnet." To get those features, you start patching:
Need better intake? Add Lawmatics (+$200/mo)
Need better phones? Add Dialpad (+$30/user)
Need file automation? Add NetDocs (+$60/user)
Need to connect them? Pay for Zapier (+$50/mo)
Suddenly, your $220/user spikes to $600+/user. Your monthly subscription tax rate triples, but your efficiency doesn't.
THE UGLY
Your firm is now a "Frankenstein" of 10 different apps.
Your paralegals are copy-pasting data between 3 different tabs (and making errors).
You are paying exorbitant subscription fees for features you use 10% of.
When one API updates, your whole workflow breaks.
You feel trapped. You are renting your firm's operations, and the rent keeps going up.
THE DECISION
Most owners think the only option is to switch to a different SaaS competitor. (Spoiler: They have the same problems).
The Smart Decision: Build your own IP. Stop renting generic workflows. For the same price you are wasting on "Band-Aid" subscriptions, you could build a custom intake & management layer that does exactly what your firm needs, and nothing it doesn't.
Don't just run a law firm. Build a tech-enabled business.
I think 2030 will the most profitable year for securities lawyers
I have been reading a lot about financial crises, the dot-com bubble etc. AND there is something fishy going on in the AI world.
Now see, OpenAI has committed to roughly $1.15 trillion in infrastructure spending over the next 5 years - these are the deals the company made recently:
1. Nvidia $100 billion
2. AMD $90 billion
3. Broadcom $350 billion
4. Oracle $300 billion
5. Microsoft $250 billion
This is an unprecedented scale of investment for a single entity, which is currently losing $10-12 billion quarterly.
The planned data centers require upwards of 10 to 26 gigawatts of power, enough to power major metropolises like New York City.
Here's the math:
For a single entity who's revenue projection by Dec 2025 was just $20 Billion, it would need to grow 85x to get to $983 billion by 2030 - just to cover the infrastructure cost. is it possible? maybe, but highly improbable.
Recently the CFO of OpenAI suggested a potential federal backstop if these commitments fail. IF these commitments fail, the US tax payer will be burned to bail out. 1.15 trillion means this will trickle down to many other countries as well.
But this isn't crazy yet, lets see another angle why this commitment has a deeper financial issue - There is a deep "circular revenue" issue lurking:
Microsoft invests in OpenAI -> OpenAI uses that money to buy Microsoft azure cloud services -> Microsoft uses that money to buy Nvida chips -> Nvidia invests back into OpenAI. The circle keeps on going again and again.
I am not saying this will lead to something similar to global financial crises of 2008 or dot-com bubble but there is something fishy going on with these companies.
I just wish I am wrong, but have you guys been studying the patterns here?
Mahatma Gandhi was asked a simple question, what would you choose gold or silver? He said, I’d choose health.
Invest into a comfortable chair today, specifically if you’re someone who sits for a long time each day.
And your 50 year old self will thank you.
For developing law firms, a custom intake program is highly suitable. While SaaS introduces firms to automation, such as client onboarding and replacing paper forms, many firms, particularly those like immigration law, which involve complex, multi-jurisdictional compliance and case-specific workflows, often outgrow these platforms not long after. Custom Intake Systems offer tailored workflows, automated eligibility screening, and scalable processes, ensuring efficiency, compliance, and long-term growth for specialized and expanding firms.
https://t.co/i4NpObO9QO