Law Subscribed

(198.5) AI-Driven Collapse of the Billable Hour, Part 2

Law Subscribed — Thu, 22 Oct 2026 11:01:44 GMT

Here are the top 5 takeaways from this episode:

AI is shrinking BigLaw’s workforce needs as firms that once needed a thousand lawyers can operate with far fewer, pushing displaced attorneys to start their own AI-native firms and serve the previously unmet “latent legal market.”
Subscriptions and flat fees solve the unpredictability problem for clients by offering transparent, scope-based pricing that adapts when cases change (e.g., uncontested to contested), giving clients certainty during stressful times while still compensating attorneys fairly.
Scope definition is the single most important factor in setting flat fees, and attorneys must audit a typical matter, itemize every task included and excluded, and price based on client value rather than simply multiplying old hours by old rates.
Clients hate hourly billing and will increasingly choose firms that offer predictable pricing, making flat fees and subscriptions a competitive marketing advantage that builds trust rather than eroding it the way hourly billing does.
Law schools and students must embrace AI now because the traditional legal career ladder is changing, but the core skill of “thinking like a lawyer” remains valuable as a critical-thinking foundation for directing and leveraging AI tools effectively.

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(198) Ethical Legal Billing in the AI Era with Susan E. Guthrie of The Practice Playbook

Law Subscribed — Thu, 15 Oct 2026 11:01:50 GMT

Here are the top 5 takeaways from this episode:

AI is not a search engine. Many lawyers still treat AI like Google, which completely misses its collaborative potential and underwhelms them, like driving a Maserati like a Datsun.
The billable hour cannot survive AI efficiency. Clients already know AI can speed up legal work and are pushing back on hourly billing, making alternative fee models a strategic necessity rather than an optional experiment.
Transparent flat fees and subscription pricing build trust with clients. Susan’s consultation conversion rate jumped to over 95% when she proactively discussed flat-fee pricing, because it replaced the adversarial “did you really spend that much time?” dynamic with upfront clarity.
AI hallucinations mirror human memory errors, so verification is the fix for both. Both hosts shared personal stories of confidently recalling wrong event details, illustrating that the solution is the same whether you are a human or an AI: go back to the primary source before answering.
The legal profession is at a major inflection point with no breathing room. AI adoption among lawyers happened faster than any prior technology shift, and practitioners who treat it as an opportunity rather than an existential threat will be the ones who thrive.

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(197.5) AI-Driven Collapse of the Billable Hour, Part 1

Law Subscribed — Thu, 08 Oct 2026 11:00:24 GMT

Here are the top 5 takeaways from this episode:

AI compresses the time for legal work but the billable hour penalizes that efficiency, meaning lawyers who adopt AI tools earn less for delivering the same or better results faster.
The billable hour model creates a misalignment of incentives between attorney and client, encouraging unnecessary litigation and opacity rather than speed, value, and trust.
Clients are already demanding AI savings show up in their bills, with 60% of firms reporting client expectations that AI should reduce billed hours, making the shift to alternative fee structures an imminent market pressure rather than a future possibility.
Lawyers remain fully responsible for AI-assisted work product and must maintain human oversight through review, issue spotting, and verification, even as AI handles increasingly substantive tasks like contract analysis and drafting.
Alternative fee models like flat fees and subscriptions open access to the latent legal market, the large segment of potential clients who need legal services but cannot afford unpredictable hourly billing, while also letting lawyers reinvest saved time into growth or personal life.

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(197) General Counsel + Subscriptions with Bill Price of SubscriptionGC

Law Subscribed — Thu, 01 Oct 2026 11:01:28 GMT

Here are the top 5 takeaways from this episode:

Bill Price’s ALSP, Subscription GC, charges a flat monthly fee that is cheaper than big law but still premium, aligning incentives around getting things done rather than billing for time.
By handling repetitive, administrative tasks, AI lets lawyers move up the strategic stack and spend more time on business decisions, relationship-building, and nuanced in-person negotiations that technology cannot replicate.
Bill recommends evaluating whether to maintain your own data and models, whether you can afford the time and money to build, and whether you can keep everything updated and secure, concluding that a platform like Practi was a no-brainer for his needs.
Rather than replacing lawyers, AI and automation will increase demand and create more work, as efficiencies open new markets and opportunities, especially in the subscription legal services space.
Lawyers from both backgrounds are drawn to the flexibility, predictable pricing, and better work-life balance of subscription practices, with some eventually receiving offers from the very clients they serve.

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(196) Investing in AI for the Legal Industry with Matt Ober of Social Leverage

Law Subscribed — Thu, 24 Sep 2026 11:02:06 GMT

Here are the top 5 takeaways from this episode:

AI augments rather than replaces lawyers by handling repetitive document review and data extraction, freeing attorneys to focus on higher-value work that clients actually want to pay for.
Proprietary data is the key moat for legal tech companies because unlocking a firm’s private, non-public data through AI platforms creates efficiency and competitive advantage that generic tools cannot replicate.
Flat-fee and subscription pricing models are investable and gaining traction, as demonstrated by Social Leverage’s early 2018 investment in Marble/Flare, a technology-powered law firm that charges fixed fees instead of billing by the hour.
Specialized legal AI platforms like Harvey must price carefully to stay sticky enough that law firms do not abandon them for cheaper general-purpose tools like Claude or ChatGPT, which could eventually become good enough for many use cases.
Massive opportunities exist in overlooked legal niches, such as securities class action claims where 75% of eligible claimants never file and billions of dollars go uncollected, showing that niche legal tech can build hundreds of millions in revenue while remaining nearly unknown.

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(195) How to Manage A Small Law Firm with RJon Robins

Law Subscribed — Thu, 17 Sep 2026 11:02:10 GMT

Here are the top 5 takeaways from this episode:

The billable hour was introduced by the insurance industry in the late 1960s and early 1970s, replacing the value-based and flat fee model lawyers had used for over a thousand years, and it created perverse incentives that harm lawyers, clients, and the profession.
RJon Robins’ company, How to Manage a Small Law Firm, provides fractional C-suite services to over 500 small law firms on a subscription retainer basis, generating roughly $3.5 million per month in recurring revenue and proving the subscription model works at scale.
The billable hour disincentivizes efficiency, collaboration, and collegiality among lawyers by rewarding inefficiency and turning attorneys and their clients into adversaries rather than trusted counselors.
Many lawyers leave mid-size and large firms due to discrimination and start their own practices where they can build businesses on their own terms, often ditching the billable hour for value-based or subscription billing.
AI should be treated like a brilliant but inexperienced junior associate who is great for grunt work and spotting trends, but lawyers must apply their own wisdom and judgment rather than abdicating strategic and values-based decisions to AI.

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(194.5) Why Legal Innovation Deserves its Own Oscars with Tom Martin of LawDroid

Law Subscribed — Mon, 14 Sep 2026 11:02:21 GMT

Here are the top 5 takeaways from this episode:

Tom Martin’s LawDroid is developing pre-emptive techniques through its Spectral Mind R&D lab to eliminate hallucinations before they reach the user, building on the success of CiteCheck AI which has already verified over 15,000 citations.
Tom’s upcoming book argues that software alone or services alone is no longer defensible as a business, and the three pillars feed each other to create continuous improvement for legal tech companies.
Both hosts agree that using AI to help students understand complex material faster is valuable, but outsourcing the actual thinking or analysis to AI undermines the educational purpose, and law schools that embrace this distinction give their graduates a competitive edge in the job market.
Dubbed “Law Prom,” the black-tie ceremony at Suffolk Law School on October 25, 2026, honors innovators across ten categories including lifetime achievement, AI, and access to justice, with early bird tickets available through September 15.
The most valuable work lawyers do in an AI-powered world is judgment and discernment, which takes little time to execute but requires years of experience to develop, making it difficult for time-tracking tools to accurately reflect the worth of legal services.

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(194) The Ditching Hourly Guy + The Subscription Attorney Reunite (and How to Go Live on LinkedIn)

Law Subscribed — Thu, 10 Sep 2026 11:02:11 GMT

Here are the top 5 takeaways from this episode:

You can go live on LinkedIn through Zoom by connecting a custom stream URL, but you must wait 30 to 40 seconds for the LinkedIn lag before clicking “Go Live” and switch to gallery mode first if you want to control your thumbnail.
AI is collapsing the time it takes to do professional work, which makes hourly billing financially punishing for anyone who invests in productivity tools because better efficiency means less billable time and lower revenue.
Clients never wanted your hours in the first place; they wanted the outcome, so switching to fixed pricing or subscription models lets you benefit from being fast and good instead of being penalized for it.
Pre-generative AI content like long-running podcasts may be more valuable going forward because AI engines treat older, clearly human-created content as more trustworthy and authoritative than AI-generated material.
You can streamline an entire podcast production workflow by recording live on LinkedIn through Zoom, importing directly into Descript, removing filler words automatically, applying Studio Sound at a low intensity, and exporting in about five minutes.

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(193) Family Law and Estates + Subscriptions with Natalie Thomas of The Legal Joint LLC

Law Subscribed — Thu, 03 Sep 2026 11:01:17 GMT

Here are the top 5 takeaways from this episode:

Natalie Thomas chose a trade name (The Legal Joint) instead of her personal name so the firm could eventually be sold or run independently without being tied to her identity.
She offers tiered flat-fee pricing with three levels (navigator for DIY, co-pilot for guided help, and autopilot for full representation) to make legal services affordable for middle-income clients who cannot justify open-ended hourly billing.
The billable hour fails everyday clients because they cannot predict costs, often exhaust their savings on the initial retainer, and disputes over charges waste non-billable time that could go toward actual legal work.
AI tools are essential for flat-fee attorneys because efficiency is the only way to make fixed pricing profitable, and lawyers who refuse to adopt them will be left behind like those who resisted email and cell phones.
A subscription model could solve Natalie’s biggest revenue problem by converting one-time clients into recurring monthly subscribers for post-divorce compliance, estate planning check-ins, and ongoing legal access.

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(192.5) Subscription Billing Mechanics and Ethics for Law Firms

Law Subscribed — Mon, 31 Aug 2026 11:03:32 GMT

Here are the top 5 takeaways from this episode:

Subscription billing aligns attorney and client incentives by rewarding ongoing value and proactive problem avoidance instead of penalizing efficiency the way the billable hour does.
Recurring fixed fees give law firms predictable revenue and smoother cash flow while giving clients pricing certainty and removing the fear of contacting their lawyer.
True subscription billing requires explicitly bounded scope with recurring fixed fees that expire and refresh each cycle, not presold hours or payment plans tracked against time.
Transparent pricing on your website not only builds client trust but also helps AI tools surface your firm when potential clients ask for lawyer recommendations.
California rules of professional conduct require proper written disclosures, and for fees over $1,000, a signed agreement from the client.

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(192) Answer/Generative Engine Optimization with Danny Decker of Spotlight Marketing + Branding

Law Subscribed — Thu, 27 Aug 2026 11:00:00 GMT

Here are the top 5 takeaways from this episode:

Being a great lawyer doesn’t automatically attract clients; law firms need strong marketing to bring in the right clients, not just more clients.
Recurring subscription revenue benefits both the law firm and its clients by enabling long-term planning, consistent service, and predictable budgeting on both sides.
To show up in AI search results, law firms must publish content that directly answers the questions their clients are already asking, especially about pricing.
Putting pricing information on your website is no longer optional, as AI platforms like ChatGPT are actively pulling cost data to answer client queries.
Consistent visibility across platforms (LinkedIn, website, YouTube, third-party publications) with a uniform business name and regular content is the foundation of being recommended by AI search tools.

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(191.5) Curation and Tase are Your Superpowers Workshop

Law Subscribed — Mon, 24 Aug 2026 11:02:08 GMT

Here are the top 5 takeaways from this episode:

Subject matter expertise remains essential because AI only works as well as the knowledge and curation you bring to it.
Gemini Notebook (formerly known as NotebookLM) lets you build curated knowledge tools by loading specific, vetted sources and generating audio overviews, video explainers, slide decks, and study guides from them with a few clicks.
Use purpose-built AI tools instead of general LLMs directly, since wrappers like Gemini Notebook and Perplexity are designed to ground answers in sources and reduce hallucinations.
Taste and curation are the real skills, as the quality of your output depends on which sources you select and how you customize the generated content for your specific audience.
This workflow is repeatable and scalable for solo practitioners and teams, enabling one person to produce high-quality, personalized educational content for clients without billing by the hour.

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(191) Fractional General Counsel + Subscriptions with Drédeir Roberts of Drédeir Law

Law Subscribed — Thu, 20 Aug 2026 11:02:05 GMT

Here are the top 5 takeaways from this episode:

Unexpected setbacks can accelerate your path. Drédeir didn’t pass the bar on the first try, took a contracts manager role to pay the bills, and ended up being offered a GC position at a national company before many peers had even started at a firm.
In-house experience reframes how you think about legal billing. Having managed outside counsel budgets, Drédeir saw firsthand how unpredictable hourly billing disrupts business planning. Clients care about cost per transaction, not how long something takes.
Niche selection matters, but stay flexible early on. Drédeir chose fractional GC work in clean tech and construction because of genuine expertise in AI governance and AEC licensing, but used his own name for the firm to avoid locking into a brand before the market validated the focus.
Subscription pricing mirrors how the rest of the business operates. Rather than selling hours, Drédeir structures fees around how much of his time and attention a client needs. Tiers keep it simple, predictable, and scalable without bespoke negotiation on every engagement.
Flat fees let you practice better law. When you are not tracking hours, you double-check your work without guilt, move faster, and focus on delivering value rather than justifying time entries. Efficiency benefits the lawyer; quality benefits the client.

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(190.5) How to Use Google Workspace for Law Firms

Law Subscribed — Mon, 17 Aug 2026 11:02:39 GMT

Here are the top 5 takeaways from this episode:

Gemini Notebook (formerly, Notebook LM) is the standout tool. The speaker calls it “the best value in Google Workspace.” It uses retrieval-augmented generation (RAG) to answer questions only from sources you provide, making it ideal for analyzing contracts, running playbooks against briefs, and even as a client-facing lead generation tool.
Listen to your documents. Google Docs has a built-in text-to-speech feature (the play button next to the editing mode toggle) that lets you listen to documents at variable speeds. It’s a significant time-saver for document review, especially for auditory learners, though it’s currently limited to ~6 pages at a time.
Google Workspace’s subscription tier matters. The Business Standard plan (~$14/month) unlocks Gemini Notebook Pro, advanced Gemini features, Google Cloud Search (search across your entire Google ecosystem at once), and HIPAA compliance options via a free Business Associate Agreement (BAA). The starter tier is insufficient for serious law practice.
Underused productivity features. Chrome tab groups (organized per client, synced across devices), email aliases/alternates (use multiple domain emails without extra seats), and Google Cloud Search are powerful built-in tools most attendees hadn’t fully explored. Google Sheets’ Gemini integration can also auto-build tracking spreadsheets by pulling from existing email/payment data.
AI-powered video and podcast generation from legal documents. Gemini Notebook’s Video Overview and Audio Overview features can turn a client handbook, brief, or contract into an explainer video or debate-style podcast. This lets lawyers deliver client-facing explanations without recording themselves, and the debate feature can surface gaps in legal arguments before filing.

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(190) Startup GC + Subscriptions with Ryan Juliano of Darwin Legal

Law Subscribed — Thu, 13 Aug 2026 11:03:12 GMT

Here are the top 5 takeaways from this episode:

Big Law wasn’t the right fit and he knew it early. After starting at Kirkland & Ellis, Ryan realized around the three-year mark that the big law “escalator” didn’t align with the life he wanted. Working 2,500 hours a year on private equity deals with no real meaning, surrendering his schedule, and watching colleagues go weeks without seeing their kids pushed him to find a different path.
Subscription-based fractional GC is about being a partner, not a vendor. Ryan deliberately chose a subscription model over flat fees or hourly billing so he could function as a true chief legal officer for his clients, someone with a permanent seat at the table rather than someone called in only when problems arise. His goal: make legal proactive, not reactive.
AI and community were the twin catalysts for going solo. The rapid rise of generative AI (especially Claude) combined with joining HeyCounsel, a 400-person network of solo/boutique attorneys, gave Ryan the confidence and infrastructure to launch Darwin Legal in July 2025. Neither alone would have been enough.
Pricing v1 failed; iteration is essential. Ryan launched with a lower-tier subscription that attracted clients who undervalued his time. He pivoted to a higher-floor model (quarterly commitment after an initial 3-month month-to-month period) to filter for clients who want a real legal partner. His takeaway: if it’s working for both supplier and client, ship it and don’t let perfectionism stall you.
The tools of a solo practice are staggeringly affordable now. Ryan runs Darwin Legal on a lean stack: Claude (~$25/month), Spellbook, Marveri, QuickBooks, and recurring payment automation. His biggest expense is malpractice insurance. Automated billing alone, he says, was one of the best quality-of-life upgrades he made by eliminating the time drain of chasing hourly invoices.

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(189.5) How The Subscription Attorney Actually Uses AI Tools

Law Subscribed — Mon, 10 Aug 2026 11:02:49 GMT

Here are the top 5 takeaways from this episode:

Treat AI like a brilliant entry-level employee. AI tools are incredibly knowledgeable (having “read everything on the internet”), but they work best when given clear context, iterated on, and never blindly trusted as a source of truth. Think of each new conversation as their first day on the job.
Use a structured, perspective-driven prompt. Always tell the AI who you are, who your client is, what document is being analyzed, and from whose perspective. This prevents generic, both-sides analysis and produces targeted, actionable output.
Run the same analysis across multiple AI tools. Using Paxton (legal-specific), Gemini Notebook (broad research), and Perplexity (internet + multi-model) in parallel surfaces different insights. Each tool catches things the others may miss, providing a more comprehensive review in minutes rather than hours.
Iterate the output and don’t stop at the first result. After the initial analysis, follow up with prompts like “draft this as a letter to my client” or “simplify the language.” This refines the output into polished, client-ready work product without starting from scratch.
Always verify citations against the source document. Tools like Paxton and Gemini Notebook link their analysis points back to the specific clauses they reference. Always click through and read the actual contract language, trust but verify, since AI is not infallible and your legal judgment is still essential.

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(189) The Future of Law Firm Business and Innovation with Jon Campisi of Centellic

Law Subscribed — Thu, 06 Aug 2026 11:00:44 GMT

Here are the top 5 takeaways from this episode:

AI is reshaping the legal industry across all levels. From law schools mandating AI courses to federal judges using AI tools, adoption is broad and not limited to younger generations. Jon expected a generational divide but found AI enthusiasm cuts across all age groups.
Private equity is entering big law, but firms are cautious. PE interest in law firms is growing, with firms exploring structures like MSOs (Management Service Organizations) to separate legal practice from operations. However, no major big law firm has publicly accepted PE investment, yet most are waiting to see who goes first.
Billing structures are shifting away from the billable hour. AI is driving efficiency (tasks that took hours now take minutes), pushing firms and clients toward flat fees and AFAs. One AM Law 100 firm’s top three clients are already on flat fees. The shift is practice-area dependent, not a blanket change.
Law firms are generating new revenue by advising clients on AI. AI has created an entirely new category of legal work: advising clients on their own AI-related issues, regulations, and compliance. Data center practices are also booming due to AI infrastructure demand.
Regulatory arbitrage is a key factor. Jurisdictions vary widely. Arizona eliminated its Rule 5.4 prohibition on non-lawyer ownership, and the UK did so even earlier, making them more progressive markets. Global firms must navigate different rules across jurisdictions, and the US may eventually follow suit, with some firms setting 2030 as a target year for significant structural change.

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(188.5) Human Intelligence Still Matters for AI-Powered Legal Work

Law Subscribed — Mon, 03 Aug 2026 11:03:43 GMT

Here are the top 5 takeaways from this episode:

Human intelligence still matters: AI raises the floor for everyone, but curation, taste, and expertise are the irreplaceable human skills that will differentiate you in an AI-saturated world.
Don’t accept default output: Iterating with AI tools, going back and forth, refining, and personalizing, produces far better results than accepting whatever the first draft delivers.
Use purpose-built tools for the right job: No single tool does everything well, so curating the right AI tool for each specific task (research, drafting, learning, client explainers) is essential.
Ground AI in your own sources: Tools like NotebookLM (now known as Gemini Notebook) that answer only from sources you provide are more accurate and trustworthy than relying on general training data, especially for legal work.
Build a second brain: Curating a personal knowledge base from your own materials, past work, and expertise gives you a searchable, queryable resource that extends and supplements your own memory and judgment.

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(188) Employment Law + Subscriptions with Stuart Rudner of Rudner Law

Law Subscribed — Thu, 30 Jul 2026 11:00:28 GMT

Here are the top 5 takeaways from this episode:

The billable hour damages client relationships. Stuart’s core message is that charging by the hour makes clients afraid to pick up the phone, meaning they only call when things have already gone wrong, making prevention impossible and the relationship transactional.
Fixed fees and phased billing are a practical starting point. Rudner Law has moved to phase-based fixed fees for litigation (e.g., a flat fee for the negotiation phase, then a separate fee for pleadings), giving clients cost certainty without requiring lawyers to price an entire matter upfront.
Subscription models work for proactive legal work. Stuart described offering subscription-based services where clients receive quarterly contract and policy updates as employment law evolves, reducing risk and creating ongoing and predictable revenue for the firm.
AI is accelerating the shift away from hourly billing. Stuart uses ChatGPT, Claude, and Thomson Reuters’ Co-Counsel to dramatically speed up research and document review. He acknowledged that billing by the hour makes no sense when AI can do 85% of the work in minutes, which makes value-based billing not just preferable but necessary.
The subscription conversation requires a new kind of client dialogue. Unlike the billable hour where the only discussion is the rate, subscriptions require transparent upfront conversations about what’s included, what’s not, usage limits, and the ability to cancel. This is a shift that Stuart sees as ultimately building deeper, more trusting client relationships.

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(187.5) AI-Driven Law Practice: Perplexity & Agentic Tools Demo

Law Subscribed — Mon, 27 Jul 2026 11:01:19 GMT

Here are the top 5 takeaways from this episode:

Perplexity Enterprise is a cost-effective, secure AI hub for lawyers. At $400/year, it provides SOC 2, HIPAA, and GDPR compliance while giving access to multiple top AI models without needing separate subscriptions to ChatGPT, Claude, or Gemini.
The Comet Browser unlocks agentic workflows that let AI control your browser on your behalf. By clicking “Control Browser,” you can instruct Perplexity to navigate websites, fill out forms, and complete tasks like adding calendar events without you lifting a finger.
Connectors (MCPs) let Perplexity directly read and write to tools like Google Calendar and Drive. Once connected, the AI can bulk-schedule deadlines from case management orders or contracts by computing dates itself using its Wolfram Alpha integration.
AI can handle contract redlining and document drafting in stages, with the lawyer staying in the loop. By combining Paxton for legal analysis with Perplexity’s agentic browser to apply suggested edits in Google Docs, attorneys can maintain judgment and oversight while offloading manual work.
Whisprflow enables voice-driven input across all apps for around $288/year. Speaking instead of typing, with the AI intelligently cleaning up dictation errors, dramatically speeds up the process of giving instructions to AI tools throughout the day.

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