[Note: This year marks the 30th in which I’ve been tracking the development of legal tech — or at least that is the earliest evidence I can find of when I started regularly writing about the subject.
In commemoration of that milestone, I decided to write a post highlighting the major themes that have characterized legal tech’s evolution over the past three decades.
As I pondered that topic, it occurred to me to enlist ChatGPT as a collaborator. Honestly, I did not expect what it produced.
Here is the prompt I provided (using ChatGPT’s Deep Research feature):
“I am a legal tech journalist named Bob Ambrogi who has been writing about legal tech for 30 years. I would like to write an essay about what I’ve learned about legal tech and the legal industry over those years. Please do some research on my writings over the years and see if you can suggest any themes that jump out.”
I expected, maybe, some bullet points. Instead, I got an essay. Here, in full, is what it delivered. It misses my early writing, and picks up from I started this blog in 2002]
Recurring Themes in Bob Ambrogi’s Authorized Tech Commentary
Evolution of Authorized Know-how: From Early Internet to AI Revolution
Bob Ambrogi’s writings hint an arc of authorized know-how evolution spanning many years – from the nascent authorized net of the Nineteen Nineties to immediately’s AI-driven instruments. He launched his LawSites weblog in 2002 as a method to maintain readers abreast of recent authorized web sites, shortly after authoring a e book on the “nonetheless nascent however quickly evolving authorized net.” In its early days, LawSites targeted on cataloguing helpful on-line assets for legal professionals, reflecting Ambrogi’s pleasure over the abundance of free authorized info the web supplied.
Over time, he broadened his scope past web sites to embody authorized know-how, innovation, ethics, and authorized media, as he famous when his weblog marked its nineteenth anniversary in 2021, successfully giving himself a front-row seat to the transformation of legislation via tech. He as soon as marveled at how “over the course of [his writing], the world of authorized know-how has modified dramatically,” calling it a “true present” to have a ringside view of those adjustments.
In Ambrogi’s commentary, every period of authorized tech comes alive. He recounts milestones such because the rise of cloud-based observe administration within the late 2000s – noting that 2008 noticed the launch of the primary SaaS legislation observe platforms Clio and Rocket Matter, adopted by MyCase in 2009 and a flurry of rivals quickly after. He attracts strains from these early improvements to immediately’s panorama, which is more and more outlined by synthetic intelligence. Ambrogi has constantly tracked the development of AI in legislation, from early professional sstems and initiatives like IBM Watson-based authorized analysis, to the present explosion of generative AI instruments.
Actually, his work usually highlights pivotal moments the place tech leaps ahead: for instance, he reported on the “landmark deal” in 2025 of observe administration firm Clio buying the AI authorized analysis platform vLex for $1 billion, a merger he mentioned would “undoubtedly reshape the authorized tech panorama.”
By means of weblog posts, podcast interviews, and convention protection, Ambrogi chronicles how once-experimental concepts have turn out to be mainstream. He credit authorized tech entrepreneurs and innovators for this progress, saying they “constantly amaze me with their ingenuity and creativity and make day-after-day of masking authorized tech extra thrilling than the one earlier than.” This lengthy view of evolution – from dial-up authorized analysis to AI assistants – is a continuing backdrop in his commentary, giving readers historic context for every new improvement.
Challenges in Authorized Innovation and Adoption
A recurring theme in Ambrogi’s commentary is the authorized career’s sophisticated relationship with know-how – a mixture of optimism about innovation’s potential and candid critique of the obstacles to adoption.
He usually pushes again towards the cliché that “legal professionals are gradual to undertake new know-how.” In an Above the Regulation column, Ambrogi argued that it’s not all the time the large companies on the leading edge – traditionally, solo and small-firm legal professionals have usually led the pack in tech adoption, leveraging new instruments to achieve capabilities they in any other case lacked.
He traces this phenomenon again to the Nineteen Nineties: “Approach again in 1995, I wrote {a magazine} article about know-how’s influence on the authorized career, discussing how know-how empowered solo and small-firm legal professionals,” successfully leveling the enjoying area towards bigger companies. This perception – that know-how can democratize observe – underpins a lot of his writing.
But Ambrogi can be frank concerning the persistent obstacles and missteps in authorized innovation. He notes that many attorneys stay hesitant or lack understanding of recent instruments, a actuality he has noticed anecdotally (resembling throughout a 2024 speak the place solely a few trial legal professionals within the viewers had ever tried ChatGPT). Frequent obstacles like lack of tech literacy, funds constraints, and cultural resistance come up often in his protection.
Ambrogi highlights how the COVID-19 pandemic, regardless of its hardships, served as an “accelerant” for tech adoption – forcing legal professionals out of the “that is the way it’s all the time been” mindset and proving that distant observe and digital workflows are possible. Surveys he reported on affirm that the pandemic spotlighted know-how’s crucial function and certain vaulted adoption ahead by years, even when many companies admit they weren’t absolutely ready for this fast change.
Ambrogi additionally isn’t shy about calling out hype versus actuality in authorized tech. He cautions that not each shiny new product will succeed – some fizzle out shortly. “Simply because you may doesn’t imply it is best to,” he writes, emphasizing that authorized tech ought to remedy actual issues or fill real wants slightly than exist for its personal sake. In his view, profitable merchandise are people who “simply work” seamlessly for legal professionals and ship tangible advantages like effectivity or better advocacy energy.
He has overtly criticized startups for ignoring classes of the previous. As an illustration, when the well-funded authorized startup Atrium launched in 2017 vowing to “revolutionize” authorized companies, Ambrogi instantly in contrast it to Clearspire, a strikingly comparable dual-entity legislation agency/tech firm that had failed just a few years prior – “Those that neglect the previous are doomed to repeat it,” he quipped. Certainly, Atrium finally met the identical destiny as Clearspire.
This historic perspective is a trademark of Ambrogi’s commentary: he usually reminds readers that immediately’s authorized tech “disruption” isn’t all the time unprecedented, and that understanding why earlier improvements failed can yield worthwhile classes. By spotlighting high-profile “authorized tech fails” alongside success tales, Ambrogi gives a balanced view – celebrating progress but in addition urging warning, realism, and user-centered design in authorized innovation.
Regulation Agency Innovation vs. Company Authorized Demand: Shifting Dynamics
One other key sample in Ambrogi’s writing is his evaluation of how totally different segments of the authorized business embrace know-how – specifically, the evolving dynamic between legislation companies and company authorized departments. Through the years, he has noticed a major shift within the stress and expectations round tech.
Company shoppers, in Ambrogi’s view, have turn out to be a significant driver of innovation. He cites survey knowledge displaying that 91% of company authorized departments now ask or plan to ask their outdoors legislation companies to element the know-how they use to be extra environment friendly – a outstanding indication that tech functionality is not optionally available however anticipated in consumer service.
Actually, use of know-how has climbed to the very high of shoppers’ standards for evaluating legislation companies (outranking even worth or different price preparations), a pattern Ambrogi notes with some irony since many legislation companies traditionally underestimated how a lot shoppers cared about tech adoption. The message is evident: in-house authorized groups need their companies to leverage trendy instruments, and they’re more and more rewarding tech-forward companies with enterprise.
Regulation companies have responded, albeit inconsistently. Ambrogi paperwork what number of companies, particularly bigger ones, have ramped up funding in know-how and even created formal innovation roles or groups. By 2021, roughly three-quarters of companies mentioned they had been investing in new tech for effectivity and consumer service, and 42% had established devoted innovation teams to drive these efforts. It’s a notable cultural change for a career usually seen as conventional.
Ambrogi often highlights examples of forward-thinking companies hiring chief innovation officers, launching incubators, or partnering with startups – developments that may have been uncommon a decade in the past. He additionally factors out a rising divide by agency measurement within the adoption of cutting-edge tech like AI.
Opposite to the sample with fundamental tech adoption, the place small companies had been early movers, Ambrogi argues that generative AI is “a unique form of beast” – one the place bigger companies at present have the higher hand as a result of they’ll marshal groups of technologists and assets to soundly experiment. Smaller practices, missing IT employees, could also be slower to embrace advanced AI instruments, which raises the priority that this new wave of tech may “throw [the playing field] wildly off kilter” after years by which tech had been an equalizer.
Past legislation companies themselves, Ambrogi tracks the rise of different authorized service suppliers (ALSPs) and Massive 4 accounting companies getting into authorized companies, which has altered market dynamics. He has reported on milestones resembling KPMG’s subsidiary changing into the primary Massive 4 agency licensed to observe legislation within the U.S. (beneath Arizona’s reforms) – a “historic improvement” that indicators how non-traditional gamers armed with tech and course of experience are encroaching on legislation agency turf.
In Ambrogi’s view, company authorized departments are more and more prepared to disaggregate companies and ship work to whoever is best, be it a legislation agency, an ALSP, or a tech-enabled supplier. This has spurred legislation companies to innovate or threat shedding work.
Finally, Ambrogi’s commentary portrays a authorized business in flux: shoppers are demanding effectivity and innovation, massive companies are investing to maintain up (typically even leaping forward in areas like AI), and new rivals are forcing everybody to rethink business-as-usual. The once-glacial tempo of change in legislation companies has accelerated as they adapt to a market that rewards know-how adoption and punishes inefficiency.
Monitoring Key Applied sciences and Gamers in Authorized Tech
All through his profession, Ambrogi has made some extent of following the distributors, merchandise, and know-how traits shaping the authorized business – usually from their infancy to maturity. His weblog and columns function a working chronicle of authorized tech’s “best hits” (and flops), and sure corporations recur often in his protection as bellwethers of bigger traits.
For instance, Ambrogi has intently tracked the rise of observe administration software program for legislation companies. He notes how pioneers like Clio, Rocket Matter and MyCase basically created the marketplace for cloud-based legislation observe administration round 2008-2009. Through the years, he reported on these corporations’ milestones – from early adoption by solos, to huge enterprise capital investments, to acquisitions – utilizing their trajectories as an instance the broader mainstreaming of authorized tech.
His current writing on Clio’s $1B acquisition of vLex in 2025 is a living proof: past the headline, Ambrogi contextualized it as a convergence of observe administration with authorized analysis and AI, commenting that we might have “seen this film earlier than” in how authorized tech markets evolve. By evaluating present occasions to previous patterns, he emphasizes continuity in authorized tech’s story even amid headline-grabbing offers.
[Editor’s note: ChatGPT unduly gives me credit here. It was not I, but guest columnist Ken Crutchfield, who provided the “we have see n this move before” context.]
One other space Ambrogi constantly displays is authorized analysis and analytics instruments. He has lined the continuing competitors to disrupt the Westlaw/Lexis duopoly, chronicling startups like Fastcase, Casetext, ROSS Intelligence, and others. When ROSS, an AI-driven analysis device, emerged from a college hackathon and gained nationwide consideration, Ambrogi visited their workplaces and wrote a deep dive on its potential.
He additionally adopted the dramatic flip of occasions when ROSS was later sued by Thomson Reuters for allegedly misusing Westlaw knowledge, a lawsuit that finally compelled ROSS to close down – a saga he recounted as a cautionary story of how incumbents can stifle upstart innovation. This type of detailed vendor storytelling – from launch, to challenges, to both success or failure – is a trademark of Ambrogi’s work. It displays his function not simply as a reporter of authorized tech information, however as a curator of the business’s collective reminiscence.
Furthermore, Ambrogi retains a pulse on rising applied sciences and the way they’re adopted in authorized. Lately, that has meant a heavy give attention to synthetic intelligence, automation, and instruments enhancing authorized workflow.
By means of his weekly Legaltech Week panel and LawNext podcast, he often hosts conversations with founders of AI startups, massive legal-tech CEOs, and even leaders at conventional corporations integrating AI. His protection has spotlighted applied sciences like contract analytics, e-discovery developments, doc automation, and on-line dispute decision, usually assessing which improvements are hype and that are really transferring the needle.
Ambrogi additionally highlights “authorized tech’s best entrepreneurs” – these he believes constantly drive innovation. He has written concerning the ingenuity of authorized tech startup founders and even featured many in his podcast, successfully charting a who’s-who of the authorized tech panorama over 30 years. In sum, a reader of Ambrogi’s work positive factors not solely information of the newest product launches but in addition continuity – seeing how immediately’s large authorized tech names grew from fledgling startups and the way varied know-how niches (from observe administration to AI analysis assistants) matured over time.
This long-term, narrative strategy to masking distributors and tech traits is without doubt one of the causes Ambrogi’s commentary is so valued within the authorized group.
Entry to Justice, Ethics, and Regulatory Reform
Underpinning Bob Ambrogi’s commentary is a transparent concern for the way authorized know-how intersects with entry to justice and the general public good, in addition to the moral and regulatory buildings of the authorized career. He usually returns to the sobering actuality of the “justice hole” – the huge unmet authorized wants of low- and middle-income folks – and questions whether or not innovation is actually serving to bridge that hole.
In a single putting comparability, Ambrogi described attending two very totally different authorized tech conferences back-to-back: one a glitzy Legalweek occasion targeted on BigLaw instruments, and the opposite a modest authorized assist know-how convention. The expertise left him “troubled by the chasm between these two worlds.” He factors out that whereas roughly 50 million low-income People obtain no or insufficient authorized assist, the authorized tech business pours its cash into serving the richest shoppers. By Ambrogi’s evaluation, “the overwhelming majority of funding in authorized tech goes to merchandise that serve the authorized wants of solely a small minority, whereas tech dedicated to serving the overwhelming majority of authorized wants receives solely a minuscule portion of that cash.”
This inequity in authorized tech funding is a recurrent theme he highlights. He has even dubbed it “the justice hole in authorized tech,” arguing that there’s a structural imbalance when nearly all enterprise capital goes towards instruments for giant legislation companies and company authorized departments, whereas authorized assist tech initiatives scrape by on tiny grants. Ambrogi calls on the business to acknowledge this hole and imagines what even a fraction of these billions invested in BigLaw tech may do if directed at access-to-justice innovation.
Parallel to his give attention to entry, Ambrogi intently follows regulatory and moral developments that affect authorized tech and innovation. A serious sample in his protection is the push for – and resistance to – regulatory reform in authorized companies. He has reported extensively on states like Arizona and Utah, which broke new floor by loosening guidelines to permit non-lawyer possession of legislation companies and experimental “sandbox” applications for authorized companies.
Ambrogi sees these reforms as laboratories for innovation that might develop entry to justice. Actually, he notes {that a} major purpose and final result in Utah and Arizona has been serving bizarre shoppers: “particular person shoppers stay the first beneficiaries of those regulatory improvements,” with the overwhelming majority of recent entities in these states targeted on serving to individuals who beforehand lacked inexpensive companies. His protection of a five-year research on the Arizona and Utah experiments discovered it “encouraging” that 85–91% of the approved entities had been aimed toward particular person shoppers, confirming that the reforms are reaching the meant populations.
Simply as importantly, Ambrogi addresses the concern over ethics and client hurt in these new fashions. He experiences that in each states there was “remarkably little proof of client hurt,” citing knowledge like Utah’s minuscule variety of complaints (20 complaints out of tens of 1000’s of companies delivered). That is Ambrogi’s approach of countering the critics who worry that stress-free conventional laws (such because the ban on non-lawyer observe or possession) will result in public damage – the proof thus far, he notes, doesn’t bear out these worst-case situations.
Ambrogi additionally doesn’t draw back from criticizing the authorized institution when it pushes again towards change. He lined the controversy throughout the American Bar Affiliation, the place the ABA’s personal Innovation Middle was allegedly pressured into canceling an op-ed that advocated for regulatory reform, as a consequence of political blowback. He revealed that on the ABA’s 2023 assembly, the Home of Delegates despatched “a decidedly combined message” – successfully doubling down on prohibiting non-lawyer possession on the nationwide stage at the same time as some states moved ahead with innovation.
This rigidity between progressive states and conservative establishments is a story Ambrogi revisits usually, framing it as a battle over the way forward for authorized companies. In his view, clinging to conventional guidelines within the face of an entry to justice disaster is untenable; he often amplifies voices who argue that regulatory reform (resembling permitting tech-enabled corporations and paraprofessionals to function) is vital to narrowing the justice hole.
Lastly, Ambrogi has been a vocal proponent of technological competence as an moral responsibility for legal professionals. For the reason that ABA added Remark 8 to Mannequin Rule 1.1 in 2012 – basically urging that competent illustration now consists of staying updated with related know-how – Ambrogi has meticulously tracked state-by-state adoption of this responsibility. He even maintains a map of jurisdictions which have embraced it.
In his commentary, he usually heralds every new state that joins the fold; by mid-2025, over 40 states had accomplished so. He wrote that the ABA’s transfer in 2012 was a “sea change,” and “ever since 2012, [the ABA’s] strategy has been the template for state adoption of the responsibility” of tech competence. Importantly, Ambrogi highlights when states push the envelope additional – for instance, when Puerto Rico in 2025 not solely adopted the tech competence responsibility however wrote it immediately into its skilled conduct guidelines (going past the ABA’s remark strategy).
By reporting these developments, Ambrogi underscores a broader theme: legal professionals can not ignore know-how with out risking moral lapses. He views this as a constructive drive nudging the career towards modernity, and sometimes encourages persevering with schooling and coaching in order that attorneys meet their obligation to grasp the instruments of immediately’s observe.
In synthesizing Bob Ambrogi’s work throughout 30 years, a transparent image emerges. He’s, at coronary heart, an chronicler and critic of authorized know-how’s march ahead. His commentary returns to a set of core concepts: that know-how can empower even the smallest agency to punch above its weight if used well; that the authorized business’s tradition should evolve to completely notice innovation’s advantages; that consumer and market pressures are lastly overcoming long-held resistance; and that we should guarantee innovation serves all segments of society, not simply probably the most profitable.
Whether or not writing a few startup’s rise and fall, a legislation agency’s newest tech initiative, or a regulatory battle on the ABA, Ambrogi approaches every matter with a mix of historic perception, skepticism of hype, and real hope that higher instruments and insurance policies can enhance the observe of legislation and develop entry to authorized companies. His enduring presence in authorized tech journalism has, in some ways, mirrored and documented the authorized business’s personal journey from the analog world of 30 years in the past to the digitally reworked panorama of immediately.
