Robert Ambrogi Blog
[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 Legal Tech Commentary
Evolution of Legal Technology: From Early Web to AI Revolution
Bob Ambrogi’s writings trace an arc of legal technology evolution spanning decades – from the nascent legal web of the 1990s to today’s AI-driven tools. He launched his LawSites blog in 2002 as a way to keep readers abreast of new legal websites, shortly after authoring a book on the “still nascent but rapidly evolving legal web.” In its early days, LawSites focused on cataloguing useful online resources for lawyers, reflecting Ambrogi’s excitement over the abundance of free legal information the internet offered.
Over time, he broadened his scope beyond websites to encompass legal technology, innovation, ethics, and legal media, as he noted when his blog marked its 19th anniversary in 2021, effectively giving himself a front-row seat to the transformation of law through tech. He once marveled at how “over the course of [his writing], the world of legal technology has changed dramatically,” calling it a “true gift” to have a ringside view of these changes.
In Ambrogi’s commentary, each era of legal tech comes alive. He recounts milestones such as the rise of cloud-based practice management in the late 2000s – noting that 2008 saw the launch of the first SaaS law practice platforms Clio and Rocket Matter, followed by MyCase in 2009 and a flurry of competitors soon after. He draws lines from those early innovations to today’s landscape, which is increasingly defined by artificial intelligence. Ambrogi has consistently tracked the progression of AI in law, from early expert sstems and projects like IBM Watson-based legal research, to the current explosion of generative AI tools.
In fact, his work often highlights pivotal moments where tech leaps forward: for example, he reported on the “landmark deal” in 2025 of practice management company Clio acquiring the AI legal research platform vLex for $1 billion, a merger he said would “undoubtedly reshape the legal tech landscape.”
Through blog posts, podcast interviews, and conference coverage, Ambrogi chronicles how once-experimental ideas have become mainstream. He credits legal tech entrepreneurs and innovators for this progress, saying they “consistently amaze me with their ingenuity and creativity and make every day of covering legal tech more exciting than the one before.” This long view of evolution – from dial-up legal research to AI assistants – is a constant backdrop in his commentary, giving readers historical context for each new development.
Challenges in Legal Innovation and Adoption
A recurring theme in Ambrogi’s commentary is the legal profession’s complicated relationship with technology – a mix of optimism about innovation’s potential and candid critique of the obstacles to adoption.
He often pushes back against the cliché that “lawyers are slow to adopt new technology.” In an Above the Law column, Ambrogi argued that it’s not always the big firms on the cutting edge – historically, solo and small-firm lawyers have often led the pack in tech adoption, leveraging new tools to gain capabilities they otherwise lacked.
He traces this phenomenon back to the 1990s: “Way back in 1995, I wrote a magazine article about technology’s impact on the legal profession, discussing how technology empowered solo and small-firm lawyers,” effectively leveling the playing field against larger firms. This insight – that technology can democratize practice – underpins much of his writing.
Yet Ambrogi is also frank about the persistent barriers and missteps in legal innovation. He notes that many attorneys remain hesitant or lack understanding of new tools, a reality he has observed anecdotally (such as during a 2024 talk where only a couple of trial lawyers in the audience had ever tried ChatGPT). Common obstacles like lack of tech literacy, budget constraints, and cultural resistance come up frequently in his coverage.
Ambrogi highlights how the COVID-19 pandemic, despite its hardships, served as an “accelerant” for tech adoption – forcing lawyers out of the “this is how it’s always been” mindset and proving that remote practice and digital workflows are feasible. Surveys he reported on confirm that the pandemic spotlighted technology’s critical role and likely vaulted adoption forward by years, even if many firms admit they were not fully prepared for this rapid change.
Ambrogi also isn’t shy about calling out hype versus reality in legal tech. He cautions that not every shiny new product will succeed – some fizzle out quickly. “Just because you can doesn’t mean you should,” he writes, emphasizing that legal tech should solve real problems or fill genuine needs rather than exist for its own sake. In his view, successful products are those that “just work” seamlessly for lawyers and deliver tangible benefits like efficiency or greater advocacy power.
He has openly criticized startups for ignoring lessons of the past. For instance, when the well-funded legal startup Atrium launched in 2017 vowing to “revolutionize” legal services, Ambrogi immediately compared it to Clearspire, a strikingly similar dual-entity law firm/tech company that had failed a few years prior – “Those who forget the past are doomed to repeat it,” he quipped. Indeed, Atrium ultimately met the same fate as Clearspire.
This historical perspective is a hallmark of Ambrogi’s commentary: he often reminds readers that today’s legal tech “disruption” isn’t always unprecedented, and that understanding why earlier innovations failed can yield valuable lessons. By spotlighting high-profile “legal tech fails” alongside success stories, Ambrogi provides a balanced view – celebrating progress but also urging caution, realism, and user-centered design in legal innovation.
Law Firm Innovation vs. Corporate Legal Demand: Shifting Dynamics
Another key pattern in Ambrogi’s writing is his analysis of how different segments of the legal industry embrace technology – in particular, the evolving dynamic between law firms and corporate legal departments. Over the years, he has observed a significant shift in the pressure and expectations around tech.
Corporate clients, in Ambrogi’s view, have become a major driver of innovation. He cites survey data showing that 91% of corporate legal departments now ask or plan to ask their outside law firms to detail the technology they use to be more efficient – a remarkable indication that tech capability is no longer optional but expected in client service.
In fact, use of technology has climbed to the very top of clients’ criteria for evaluating law firms (outranking even price or alternative fee arrangements), a trend Ambrogi notes with some irony since many law firms historically underestimated how much clients cared about tech adoption. The message is clear: in-house legal teams want their firms to leverage modern tools, and they are increasingly rewarding tech-forward firms with business.
Law firms have responded, albeit unevenly. Ambrogi documents how many firms, especially larger ones, have ramped up investment in technology and even created formal innovation roles or teams. By 2021, roughly three-quarters of firms said they were investing in new tech for efficiency and client service, and 42% had established dedicated innovation groups to drive these efforts. It’s a notable cultural change for a profession often seen as traditional.
Ambrogi frequently highlights examples of forward-thinking firms hiring chief innovation officers, launching incubators, or partnering with startups – developments that would have been rare a decade ago. He also points out a growing divide by firm size in the adoption of cutting-edge tech like AI.
Contrary to the pattern with basic tech adoption, where small firms were early movers, Ambrogi argues that generative AI is “a different sort of beast” – one where larger firms currently have the upper hand because they can marshal teams of technologists and resources to safely experiment. Smaller practices, lacking IT staff, may be slower to embrace complex AI tools, which raises the concern that this new wave of tech could “throw [the playing field] wildly off kilter” after years in which tech had been an equalizer.
Beyond law firms themselves, Ambrogi tracks the rise of alternative legal service providers (ALSPs) and Big Four accounting firms entering legal services, which has altered market dynamics. He has reported on milestones such as KPMG’s subsidiary becoming the first Big Four firm licensed to practice law in the U.S. (under Arizona’s reforms) – a “historic development” that signals how non-traditional players armed with tech and process expertise are encroaching on law firm turf.
In Ambrogi’s view, corporate legal departments are increasingly willing to disaggregate services and send work to whoever is most efficient, be it a law firm, an ALSP, or a tech-enabled provider. This has spurred law firms to innovate or risk losing work.
Ultimately, Ambrogi’s commentary portrays a legal industry in flux: clients are demanding efficiency and innovation, large firms are investing to keep up (sometimes even leaping ahead in areas like AI), and new competitors are forcing everyone to rethink business-as-usual. The once-glacial pace of change in law firms has accelerated as they adapt to a market that rewards technology adoption and punishes inefficiency.
Tracking Key Technologies and Players in Legal Tech
Throughout his career, Ambrogi has made a point of following the vendors, products, and technology trends shaping the legal industry – often from their infancy to maturity. His blog and columns serve as a running chronicle of legal tech’s “greatest hits” (and flops), and certain companies recur frequently in his coverage as bellwethers of larger trends.
For example, Ambrogi has closely tracked the rise of practice management software for law firms. He notes how pioneers like Clio, Rocket Matter and MyCase essentially created the market for cloud-based law practice management around 2008-2009. Over the years, he reported on these companies’ milestones – from early adoption by solos, to massive venture capital investments, to acquisitions – using their trajectories to illustrate the broader mainstreaming of legal tech.
His recent writing on Clio’s $1B acquisition of vLex in 2025 is a case in point: beyond the headline, Ambrogi contextualized it as a convergence of practice management with legal research and AI, commenting that we may have “seen this movie before” in how legal tech markets evolve. By comparing current events to past patterns, he emphasizes continuity in legal tech’s story even amid headline-grabbing deals.
[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.]
Another area Ambrogi consistently monitors is legal research and analytics tools. He has covered the ongoing competition to disrupt the Westlaw/Lexis duopoly, chronicling startups like Fastcase, Casetext, ROSS Intelligence, and others. When ROSS, an AI-driven research tool, emerged from a university hackathon and gained national attention, Ambrogi visited their offices and wrote a deep dive on its potential.
He also followed the dramatic turn of events when ROSS was later sued by Thomson Reuters for allegedly misusing Westlaw data, a lawsuit that ultimately forced ROSS to shut down – a saga he recounted as a cautionary tale of how incumbents can stifle upstart innovation. This kind of detailed vendor storytelling – from launch, to challenges, to either success or failure – is a hallmark of Ambrogi’s work. It reflects his role not just as a reporter of legal tech news, but as a curator of the industry’s collective memory.
Moreover, Ambrogi keeps a pulse on emerging technologies and how they are adopted in legal. In recent years, that has meant a heavy focus on artificial intelligence, automation, and tools enhancing legal workflow.
Through his weekly Legaltech Week panel and LawNext podcast, he frequently hosts conversations with founders of AI startups, large legal-tech CEOs, and even leaders at traditional companies integrating AI. His coverage has spotlighted technologies like contract analytics, e-discovery advancements, document automation, and online dispute resolution, often assessing which innovations are hype and which are truly moving the needle.
Ambrogi also highlights “legal tech’s greatest entrepreneurs” – those he believes consistently drive innovation. He has written about the ingenuity of legal tech startup founders and even featured many in his podcast, effectively charting a who’s-who of the legal tech landscape over 30 years. In sum, a reader of Ambrogi’s work gains not only news of the latest product launches but also continuity – seeing how today’s big legal tech names grew from fledgling startups and how various technology niches (from practice management to AI research assistants) matured over time.
This long-term, narrative approach to covering vendors and tech trends is one of the reasons Ambrogi’s commentary is so valued in the legal community.
Access to Justice, Ethics, and Regulatory Reform
Underpinning Bob Ambrogi’s commentary is a clear concern for how legal technology intersects with access to justice and the public good, as well as the ethical and regulatory structures of the legal profession. He often returns to the sobering reality of the “justice gap” – the vast unmet legal needs of low- and middle-income people – and questions whether innovation is truly helping bridge that gap.
In one striking comparison, Ambrogi described attending two very different legal tech conferences back-to-back: one a glitzy Legalweek event focused on BigLaw tools, and the other a modest legal aid technology conference. The experience left him “troubled by the chasm between these two worlds.” He points out that while roughly 50 million low-income Americans receive no or inadequate legal help, the legal tech industry pours its money into serving the richest clients. By Ambrogi’s analysis, “the vast majority of funding in legal tech is going to products that serve the legal needs of only a small minority, while tech devoted to serving the vast majority of legal needs receives only a minuscule portion of that money.”
This inequity in legal tech funding is a recurrent theme he highlights. He has even dubbed it “the justice gap in legal tech,” arguing that there’s a structural imbalance when virtually all venture capital goes toward tools for large law firms and corporate legal departments, whereas legal aid tech projects scrape by on tiny grants. Ambrogi calls on the industry to recognize this gap and imagines what even a fraction of those billions invested in BigLaw tech could do if directed at access-to-justice innovation.
Parallel to his focus on access, Ambrogi closely follows regulatory and ethical developments that influence legal tech and innovation. A major pattern in his coverage is the push for – and resistance to – regulatory reform in legal services. He has reported extensively on states like Arizona and Utah, which broke new ground by loosening rules to allow non-lawyer ownership of law firms and experimental “sandbox” programs for legal services.
Ambrogi sees these reforms as laboratories for innovation that could expand access to justice. In fact, he notes that a primary goal and outcome in Utah and Arizona has been serving ordinary consumers: “individual consumers remain the primary beneficiaries of these regulatory innovations,” with the vast majority of new entities in those states focused on helping people who previously lacked affordable services. His coverage of a five-year study on the Arizona and Utah experiments found it “encouraging” that 85–91% of the authorized entities were aimed at individual consumers, confirming that the reforms are reaching the intended populations.
Just as importantly, Ambrogi addresses the concern over ethics and consumer harm in these new models. He reports that in both states there has been “remarkably little evidence of consumer harm,” citing data like Utah’s minuscule number of complaints (20 complaints out of tens of thousands of services delivered). This is Ambrogi’s way of countering the critics who fear that relaxing traditional regulations (such as the ban on non-lawyer practice or ownership) will lead to public injury – the evidence so far, he notes, does not bear out those worst-case scenarios.
Ambrogi also doesn’t shy away from criticizing the legal establishment when it pushes back against change. He covered the controversy within the American Bar Association, where the ABA’s own Innovation Center was allegedly pressured into canceling an op-ed that advocated for regulatory reform, due to political blowback. He revealed that at the ABA’s 2023 meeting, the House of Delegates sent “a decidedly mixed message” – effectively doubling down on prohibiting non-lawyer ownership at the national level even as some states moved forward with innovation.
This tension between progressive states and conservative institutions is a narrative Ambrogi revisits often, framing it as a battle over the future of legal services. In his view, clinging to traditional rules in the face of an access to justice crisis is untenable; he frequently amplifies voices who argue that regulatory reform (such as allowing tech-enabled companies and paraprofessionals to operate) is key to narrowing the justice gap.
Finally, Ambrogi has been a vocal proponent of technological competence as an ethical duty for lawyers. Since the ABA added Comment 8 to Model Rule 1.1 in 2012 – essentially urging that competent representation now includes staying up to date with relevant technology – Ambrogi has meticulously tracked state-by-state adoption of this duty. He even maintains a map of jurisdictions that have embraced it.
In his commentary, he often heralds each new state that joins the fold; by mid-2025, over 40 states had done so. He wrote that the ABA’s move in 2012 was a “sea change,” and “ever since 2012, [the ABA’s] approach has been the template for state adoption of the duty” of tech competence. Importantly, Ambrogi highlights when states push the envelope further – for example, when Puerto Rico in 2025 not only adopted the tech competence duty but wrote it directly into its professional conduct rules (going beyond the ABA’s comment approach).
By reporting these developments, Ambrogi underscores a broader theme: lawyers can no longer ignore technology without risking ethical lapses. He views this as a positive force nudging the profession toward modernity, and often encourages continuing education and training so that attorneys meet their obligation to understand the tools of today’s practice.
In synthesizing Bob Ambrogi’s work across 30 years, a clear picture emerges. He is, at heart, an chronicler and critic of legal technology’s march forward. His commentary returns to a set of core ideas: that technology can empower even the smallest firm to punch above its weight if used smartly; that the legal industry’s culture must evolve to fully realize innovation’s benefits; that client and market pressures are finally overcoming long-held resistance; and that we must ensure innovation serves all segments of society, not just the most lucrative.
Whether writing about a startup’s rise and fall, a law firm’s latest tech initiative, or a regulatory battle at the ABA, Ambrogi approaches each topic with a blend of historical insight, skepticism of hype, and genuine hope that better tools and policies can improve the practice of law and expand access to legal services. His enduring presence in legal tech journalism has, in many ways, mirrored and documented the legal industry’s own journey from the analog world of 30 years ago to the digitally transformed landscape of today.