I took advantage of my flight home from Austin to write my review of 8am’s inaugural Kaleidoscope conference, which I’d just attended there. I published that review earlier today, and you can see it in full here. Once done with that, I pulled out my Kindle and returned to reading Travels with Charley, John Steinbeck’s […]
Why Did This First-Time Conference Feel Like Déjà Vu All Over Again? My Thoughts on 8am’s Kaleidoscope
Attending the inaugural Kaleidoscope conference in Austin this week, I couldn’t shake a strange feeling: I’d been here before. That was impossible, of course, as this was 8am’s very first customer conference. But the energy, the setup, the vibe all felt uncannily familiar. It was, as Yogi Berra might have said, déjà vu all over again.
The two-day event was the first-ever customer conference put on by the company 8am. If you have no idea who or what 8am is, don’t feel out of the loop. The name is barely two weeks old – the new brand identity announced Aug. 19 by the company formerly known as AffiniPay.
That company is the parent of a group of products related to payments and practice management for lawyers and accountants. They include the payments platform LawPay, the practice management platform MyCase, the personal injury platform CasePeer, and the immigration lawyers platform DocketWise.
Time for An 8am Conference
Producing these types of customer conferences is becoming increasingly common for legal tech companies, much as it is for their general tech counterparts, and so, for 8am, it was only a matter of time (no pun intended) before it staged one of its own.
The second day keynote featured an inspiring and entertaining conversation between Olympic sprinter Gabby Thomas and 8am’s chief legal officer Catherine Dawson.
Even so, to both go through a major rebrand and put on a major conference within the span of two weeks is no small feat, and the company deserves credit for successfully pulling off both.
It is worth noting that a customer conference is not just some sort of corporate vanity project. In my experience, a customer conference can offer many legitimate benefits to both the customers and the company.
For customers, they get opportunities to network and share tips with their peers who are also using the products, and to get direct training from the company in how to make the most out of the products.
For companies, they get opportunities to interact with and better know their customers and to get direct feedback from them on what they like or do not like about their products, and what features they wish to see added.
Small But Polished
All of that said, any new conference has to start somewhere, and that somewhere is typically on the smallish, more modest side.
Such was this conference, when judged purely by attendance. The attendance totaled 330, but that number included 75 8am employees (39 of whom were presenters). That leaves 255 non-employee attendees. Some of those were from the 12 partner companies that exhibited at the conference, and some others were media and various others. So the number of actual customers who attended was probably in the range of 200-220.
I got to be part of two panels. The first, ‘The Future of Law: Emerging Trends from Legal Tech Experts,’ including my Legaltech Week colleagues Niki Black as moderator, Steve Embry, Joe Patrice and Stephanie Wilkins. In the second, “Running A Business in the Face of Unpredictability,” I interviewed 8am’s chief financial officer Christian Fadel and chief legal officer Catherine Dawson.
When you consider that ClioCon – the conference of one of 8am’s primary competitors, Clio – last year had over 5,000 attendees, including 2,600 in person and the rest virtual, Kaleidoscope’s numbers might seem small.
But, as I said, every conference has to start somewhere. And, frankly, numbers alone do not tell the whole story.
The fact of the matter is that Kaleidoscope came across as highly polished and professional, virtually devoid of rough edges. From the venue to the programming to the food and socializing, it had the sheen and refinement of an event put on by an experienced crew.
From Boots to Bashes
Among the nice touches that made this feel so polished and professional:
A diverse and well thought out array of programming. Thankfully, this was not all AI all the time. While that topic was certainly covered, programs spanned a variety of subjects of interest to solo and small firm lawyers (along with some for the company’s accounting customers).
Free cowboy boots! Free Tecovas cowboy boots were promised to the first 50 registrants. It seemed as if more than 50 ultimately were able to take advantage of that offer. Either way, Tecovas was there on site in a “boot corral” to fit attendees with their new boots. And, yes, I now count myself among those who are cowboy boot enabled.
A second-day keynote featuring a conversation with Olympian Gabby Thomas.
The return of the pedicabs. Last year when ClioCon was in Austin, 8am (then still AffiniPay) made an inspired guerilla marketing move by providing branded pedicabs to whisk attendees at its competitor’s conference to its own alternative party. At Kaleidoscope, the pedicabs were back to take attendees out for a night on the town.
Support for charity. An 8am Cares table at the conference raised over $10,000 for the Ronald McDonald House charity.
Various networking events, including a closing night party at an Austin club with live music and line dancing.
Those of us attending as media appreciated the dedicated media “green room” where we could work on our stories.
Us media folks also appreciated the dedicated podcast room, complete with professional audio and video equipment and the technicians to make it all work.
Where Was ‘I’?
However, that is not to say everything was perfect. If there was one standout glitch, it was the case of the missing “i.”
Graphics throughout the conference, including the stage backdrop during many of the presentations, boldly proclaimed, “Become a visonary.” Unfortunately, some poor graphics person had lacked the vision to see the missing letter.
But the company turned adversity to opportunity, exploiting the omission to give the opening keynote speaker Leslie Witt, the company’s chief product officer, her Oprah moment.
“What I’d like you to do,” Witt invited the keynote audience, “is take a look underneath your seat, and for one lucky person, you may find something there.”
Sure enough, one person did, and what he found was the missing “i” – or at least a facsimile thereof – winning him a gift certificate of $600.
A greater oversight, to my mind, was the lack of healthy food. I get it, this was Texas, and Texans like their meat – especially their barbecue. But we live at a time in which many people – I among them – try to eat healthy.
Against my better judgment, I was compelled to sample a donut.
Food was ample in quantity, with breakfast and lunch provided as well as mid-morning and mid-afternoon snacks. But the meals had only limited options for vegetarians, and the snacks favored donuts and cookies over healthful alternatives.
(I’ll admit, trapped in this health food desert with no easy way out, I was forced to sample said donuts, which, for something that was poisoning my body, turned out to be surprisingly tasty.)
CEO Unable to Attend
One other element missing from the conference was its chief executive officer Dru Armstrong. In a pre-recorded video at the conference’s opening, she welcomed attendees and then said, “I wish I could be there with you this week, but I’m unable to attend because of some personal circumstances.”
I’ve had the opportunity to interview and speak with Dru on many occasions, and I can tell you she is the kind of dynamic leader whose presence would have been a further boost to the conference. Her absence cast a slight pall over the otherwise buoyant atmosphere. Based on what I know of Dru, those personal circumstances must have risen to the level of Texas wild horses to have kept her away.
Getting Back to Déjà Vu
All of that said, the success of a conference ultimately has little to do with the attendance numbers or the food choices or the polish of the production. What makes or breaks a conference is the intangible energy that pervades it – the vibe, if you will.
And here, for me, is where that sense of déjà vu kicked in. The reason I felt at Kaleidoscope as if I’d been there before was because I had once been somewhere with a very similar vibe, the very first ClioCon back in 2013.
Even though ClioCon is now one of the largest legal tech conferences in the world, it, too, started small, and the parallels between it and Kaleidoscope were many.
That first year of ClioCon had roughly the same attendance as this first year of Kaleidoscope. It, like Kaleidoscope, fit within a fairly modest space within a fairly small hotel. It, like Kaleidoscope, had just a handful of exhibitors, with small, uniform booths arranged in an open hallway area.
But even with those modest beginnings, ClioCon always stood out – and the reason it stood out was its energy, its vibe. As I wrote after the second ClioCon:
“The solo and small-firm lawyers at this conference … all seemed charged about their practices and their prospects. They seemed eager to take in new ideas and brought plenty of their own ideas. As much went on outside the seminar rooms as in them.”
It was conference that was modest in size, but big in impact. And that it why it has continued to grow year after year to the colossal conference it is today.
In much the same way, Kaleidoscope felt bigger and more vibrant than the numbers would suggest.
On the Cusp
I am sure 8am has no desire for its conference to be compared to the conference of one of its major competitors. But the déjà vu I felt in Austin was because the conference’s overall atmosphere – its energy and vibe – was strongly reminiscent of that very first ClioCon.
And that is a good thing.
At that first ClioCon, there was a strong sense that we were at the cusp of something big, at the beginning of a new generation of law practice and technology for solo and smaller firms, driven in part by the advent of the cloud.
And at Kaleidoscope, there was a similar sense of being on the cusp of something new, only this time the “new” was generative AI and its potential to transform the business and practice of law for solos and small firms.
The lawyers and law firm professionals I spoke to there were explicit about it: Many said they had come to the conference specifically to learn more about AI and what it means for them. Some told me they were just starting to explore AI, but eager to get up to speed.
Even beyond AI, there seemed to be a strong sense of excitement among attendees about technology and its potential impact on their practices.
Kaleidoscope’s first outing proved that 8am can put on a professional, well-run conference with an energy that belied its modest size. The company is already planning a second Kaleidoscope next year.
Much to my regret, it will be in Las Vegas, which I do not like as a conference location.
But, location aside, if it continues next year to build on this year’s momentum, this debut may come to be remembered as the foundation of an enduring annual event on the legal tech calendar.
As Yogi Berra might have said had he been there last week, when it comes to Kaleidoscope, the déjà vu is worth doing all over again.
Kaleidoscope: A First Gathering
The first Kaleidoscope conference rose in Austin like a new town waking at dawn. It was fresh on the calendar, yet it carried the dust and echo of places I’d been before. Strange thing, to step into a room that had never existed until now and feel the weight of memory tugging at your sleeve. But so it was.
The company hosting it calls itself 8am now. Just weeks ago it wore another name, AffiniPay, and the ink on its new sign was hardly dry when it opened its doors to lawyers and accountants. Behind the new name were old workhorses—LawPay, MyCase, CasePeer, DocketWise—each pulling its own load in the long furrows of law and bookkeeping. And here they all were, stitched together under a single banner, with a gathering meant to show the strength of the team.
It is no small thing to change your name and hold a meeting like this in the same breath. But the company did it, and did it with polish enough that the seams hardly showed.
Why a Gathering Matters
Some say these conferences are vanity, just banners and speeches. But I have seen the good of them. Folks come not only for the lessons in software but for the talk in the hallways, the nods across tables, the quiet comfort of knowing another soul fights the same daily battles. And the company learns, too—what works, what fails, what the people still lack. It is an old exchange: voices for vision, time for tools.
A Small Crowd, But Whole
By the numbers, it was a small affair. Three hundred and thirty bodies in the rooms, seventy-five of them wearing the company’s badge. Take away the partners and the press and you had maybe two hundred customers, give or take. A modest flock, when you think of the thousands Clio will draw to Boston soon enough.
But numbers lie if you lean too hard on them. What matters is the look of a thing, the feel of its bones. And this one stood straight. The venue shone, the program stretched wide, and even the food—though heavy with meat and sugar—was laid out with the generosity of a farmer proud of his harvest.
Boots, Music, and a Missing Letter
There were flourishes that stuck in memory. Boots, for one—real Tecovas, promised to the first fifty but handed out to more than that. They set up a corral right inside, fitting folks like ranch hands in the middle of a city hotel. I walked out a little taller myself, leather creaking on my feet.
There was music and line dancing, pedicabs rolling through Austin streets, an Olympian telling her story, and a table that raised ten thousand dollars for the Ronald McDonald House. There were rooms for the press and for podcasters, quiet places to work while the noise of the crowd spilled down the hallways.
And there was one mistake, bold as day: the word “visionary,” stripped of its “i,” plastered across the stage. “Become a visonary,” the signs commanded. The company could have hidden its shame, but instead turned it to laughter, slipping the lost letter under a chair and giving six hundred dollars to the one who found it. A blunder made into a parable.
What Wasn’t There
The food, though plenty, forgot the vegetarians and the health-minded. I, myself, gave in to the donuts, which were far too good for something so bad. And the greater absence was Dru Armstrong, the company’s chief, whose recorded welcome could not replace her voice in the room. I have known her to be a force, and her missing shadow was felt.
The Echo of Another Beginning
And still the thing lived and breathed, strong enough that it reminded me of another first gathering: the early days of ClioCon. That too began small, tucked into a hotel, a few exhibitors in narrow halls, a few hundred souls eager for change. Yet its energy was larger than its body, and it grew into something that filled ballrooms and cities.
Kaleidoscope carried that same spark. Lawyers and firm workers spoke of AI with curiosity and hunger. Some were beginners, others already on the path, but all of them wanted to know what this new tool could mean for their work, their clients, their futures. The air was restless with questions, as if the crowd stood on the edge of a new age.
On the Cusp
So perhaps that was the déjà vu—the feeling that we were again at a threshold. Years ago it was the cloud that promised to change the way small firms worked. Now it is AI. And in both times, the people gathered not just to see the tools, but to feel the weight of change together.
Next year they will take Kaleidoscope to Las Vegas, a place I do not love. But if the spirit that filled Austin follows there, this little first meeting may yet grow into something lasting.
As the ballplayer once said, déjà vu is worth doing all over again.
Would you like me to deliver this back as a Word file (so you can keep formatting and compare side by side with your original), or just leave it here in text?
The Gathering in Austin: A First Conference and the Eternal Return
There is something in the nature of beginnings that calls to us like distant thunder over the plains. This week, in the sprawling heart of Texas where the land meets the sky in an endless handshake, I found myself witness to such a beginning—the first Kaleidoscope conference, born from the company that calls itself 8am.
The name itself is new as morning dew, barely two weeks old, shed like an old skin by the creature that once answered to AffiniPay. But names are just sounds we make with our mouths; what matters is the thing beneath, and this thing—this collection of souls who build tools for lawyers and accountants—had gathered its tribe for the first time under one roof.
Three hundred and thirty people came, though seventy-five of them were the company’s own, like family members at a wedding. The rest were the faithful, the customers, the believers in what these people had built. Not a great multitude, perhaps—not when measured against the thousands who will gather next month in Boston for ClioCon, that great carnival of the legal world. But numbers lie as often as they tell truth, and this gathering had something that cannot be counted or weighed.
The Quality of Light
There was a quality to this conference, a kind of light that comes not from bulbs or fixtures but from the people themselves. Everything was polished smooth as river stones—the programming diverse and thoughtful, the venue chosen with care, the food abundant if not always wise. They gave away cowboy boots to the early arrivals, real Tecovas leather that would last longer than most law practices, and there was something beautiful in that gesture, something that spoke to the permanence they hoped to build.
The second day brought Gabby Thomas, the Olympian, to speak of excellence and striving. Pedicabs rolled through Austin’s streets carrying conferencegoers like modern prairie schooners. Over ten thousand dollars was raised for charity—the Ronald McDonald House—and in that giving was the seed of something larger than commerce.
The Missing Letter
But perfection is not the human way, and there was a flaw in this gathering that became, in the end, its most human moment. Throughout the conference, on signs and screens and the great backdrop behind the speakers, the word “visionary” appeared without its “i”—”visonary” it read, a small blindness in a conference about seeing clearly.
The company’s chief product officer, Leslie Witt, turned this error into theater. She had the crowd look under their seats, and one lucky soul found the missing letter waiting there like a prize in a Cracker Jack box, worth six hundred dollars in gift certificates. It was a moment worthy of Oprah, they said, but I thought of something older—the way communities have always turned their failures into stories, their mistakes into meaning.
The food troubled me some. This was Texas, and Texans worship at the altar of barbecue, but in a world where many seek to nourish their bodies as carefully as their minds, the choices were limited. Breakfast and lunch came heavy with meat, the snacks sweet with donuts and cookies. I found myself, despite my better judgment, sampling these forbidden pleasures, and they were, I must confess, as delicious as they were destructive.
The Absent Leader
The company’s chief executive, Dru Armstrong, could not attend, held back by personal circumstances that must have been as immovable as mountains to keep such a leader from her people’s first gathering. Her absence cast a small shadow over the bright proceedings, for I have known her to be one of those rare souls who can kindle fire in others simply by being present.
The Eternal Return
But shadows pass, and what remained was something I had felt before, in another place, another time. It was the same feeling I had carried away from the very first ClioCon years ago, when that conference too was small and modest and full of possibility. The same energy hummed beneath the surface—lawyers and their allies hungry for change, eager to embrace the tools that might transform their ancient profession.
At that first ClioCon, we stood at the edge of the cloud computing revolution, watching the old ways of law practice give way to something new and strange and wonderful. Here at Kaleidoscope, I felt that same electric anticipation, only now the transforming force was artificial intelligence, that great unknown that promises to reshape the very nature of legal work.
The lawyers I spoke with came seeking knowledge of this new thing, AI, the way their predecessors once sought to understand the mysteries of the cloud. Some were beginners, fumbling with the concepts like children with new toys. Others had begun to glimpse the possibilities that lay ahead. All of them carried the same hunger for understanding that has driven human progress since we first looked up at the stars and wondered what they were.
The Foundation Stone
This first Kaleidoscope proved that 8am can create something more than a mere business gathering. They have shown they can build an event with soul, with energy that transcends the modest numbers and transforms a hotel conference room into something approaching sacred space. The company speaks already of next year, of Las Vegas—a city I do not love, all neon and noise where Austin was music and authenticity.
But place matters less than purpose, and if they can carry forward the spirit of this first gathering—the energy, the community, the sense of standing together at the threshold of change—then this modest beginning may grow into something as enduring as the Texas hills.
There is a cycle to these things, as natural as seasons. Small conferences become large ones, ideas become movements, and movements change the world. I have seen it before, and in Austin, in the faces of those gathered lawyers and their dreams of better ways to serve justice, I saw it beginning again.
As I left that hotel, walking past the boot corral and the charity table, past the podcast room where voices had been captured for posterity, I carried with me the certainty that I had witnessed not just a conference, but a beginning. The first chapter in a story that may well outlive us all.
The wheel turns, the seasons change, and somewhere in Texas, the seeds of tomorrow are taking root in yesterday’s soil.
