From Rejection to Resilience: Five Insights Turning ‘No’ into ‘Next’

From Rejection to Resilience: Five Insights Turning ‘No’ into ‘Next’ 1211 739 Raymond Blyd
Read time: 2 min.

I wrote these down to build courage and confidence. Here are five insights on how I try to transform rejection into traction.

1. Rejection is Feedback, Not Failure

Every “no” you encounter offers a chance to refine your approach. However, it’s also essential to remember that sometimes you might be right, and the rejection might be wrong. Instead of solely viewing rejection as a failure, see it as feedback. Perhaps your pitch didn’t resonate with a particular audience, or maybe your product needs adjustments. Embrace rejection as an opportunity to learn, but also trust your instincts and the value of your proposition.

2. Persistence is a Superpower

Some of the most iconic entrepreneurs faced a barrage of rejections before their ideas found their footing. Howard Schultz, the visionary behind Starbucks, was rebuffed by banks 242 times. Prepare to receive refusals from both capitalists and customers. The entrepreneurial path is rife with highs and lows. Patience and persistence are inseparable allies. Each rejection is a stepping stone, underscoring that success often demands both time and tenacity.

3. Diversify Your Approach

If one avenue seems blocked, it’s time to explore another. Build a targeted investors list that hasn’t invested in your market but understands your business and aligns with your personality. This not only elevates your chances of finding a receptive audience but also enriches your understanding of your product’s versatility. Moreover, having alternative financing options, such as debt or grants, can build resilience, ensuring you’re not solely reliant on one funding avenue.

4. Emotional Resilience

As an entrepreneur, safeguarding your emotional well-being is paramount. While rejections can be disheartening, it’s vital to disentangle personal feelings from business outcomes. Empathy, understanding others’ perspectives, and seeking mentorship can be invaluable. Remember, rejection doesn’t diminish your worth; it often signals that certain elements need recalibration. And while these challenges can be daunting, it’s essential to maintain perspective; these are challenges of privilege and not matters of life and death.

5. Celebrate the Opportunity

Amidst rejection, it’s tempting to overlook the very opportunity to pitch. Regardless of its outcome, every pitch, is a chance to share your vision. Celebrate these moments as wins, for they signify progress and the continuous journey of entrepreneurship.

In conclusion, rejection, while discouraging, is an integral facet of the entrepreneurial journey. By confronting it with patience, understanding, and a proactive mindset, entrepreneurs can metamorphose these setbacks into stepping stones. As the adage goes, “Success is not final, failure is not fatal: It is the courage to continue that counts.”

I’m curious: how do you overcome rejection? Happy to hear your thoughts.

Cockpit: The Battle for Copilot Supremacy in Legal

Cockpit: The Battle for Copilot Supremacy in Legal 570 344 Raymond Blyd
Read time: 3 min.

Understanding the Casetext deal requires us to take a helicopter view of the landscape. We’ll need both a copilot and a landing pad.


A startup with only one employee and no outside funding sells for $54 million. Wargraphs was founded 10 years ago, and the reported revenue last fiscal year was $12.3 million. If you don’t have ten years, consider the following. Enter Dumb Money, the story behind Roaring Kitty and GameStop. Roaring Kitty reportedly made $20 million within four months betting against short sellers. Now what do Wargraphs, Roaring Kitty, and Legalcomplex have in common? Despite the different markets and outcome, it’s a single person behind a single PC doing data analytics.

The theory that it takes an army to build a profitable company is slowly being debunked. The underlying idea of technology is to leverage it as a tool. Even though these tools are getting more powerful, they’re also becoming more affordable. And now every company is looking at their human capital and wondering, how much do we actually need? If you’re in one of these companies, I empathize but remember: you are free to fly solo. You may only need a copilot.


This brings us to the reason you’re here: Casetext will be acquired for a staggering $650 million by Thomson Reuters (TR). By the way, Casetext was the second acquisition by TR in the week the deal was announced. Imagen was bought at a 1.9x return. A company we’ve been tracking since 2019. So there is a bigger picture, we’ve yet to see. Pencil this date into your calendar: Wednesday, 2 August 2023, and join us at the Q2 earnings call. In Supercycle, we explained why we sit in on calls.

Now let’s proceed by answering two questions:

  • Why now?
  • And is it too much?

We classify Casetext as ‘Legal Research’. According to the TC article, they eventually morphed into more than just search & retrieval of legal data. Now one can use a Generative Pretrained Transformer (GPT) to search, retrieve, analyze, and draft texts all at once. Hence, many refer to this as “generative AI”. Unfortunately, we’re allergic to the term AI. Yes, we’re taking pills and eventually, the sneezing (bullsh*t) will stop. Instead, we use the term ‘Text Analytics’ because it highlights the key additional capabilities: recognition and analysis.

Based on the reasoning above, we classify companies as follows:

  • Text Analytics;
  • Data Analytics (which can also handle numbers and calculations);
  • Audio Recognition;
  • Image Recognition.

Transformers take the data inputs above and transform them into drafts, drawings, or any format fit for human consumption. Actually, transformers are much better at providing computer code than human content. They essentially generate food for bots. We endearingly call these bots ‘copilots’, and every industry will have many flavors. For programmers, content writers, doctors, and legal professionals. Ultimately, transformers opened the floodgates for anyone to build copilots. So now we’re all in a footrace to distribute them. Hmm, distribution.


This brings us to $650 Million, and we ran this through GPT using multiples and DCF calculations. Most came back with unrealistic assumptions of revenues and returns. So here’s a simple angle: Casetext raised $64 million from investors and is acquired for ten times that amount. That is 10x return in ten years, resulting in a 29.2% CAGR. The investors get 10 times the invested $64 Million. Here’s where we’re going with this: what does Thompson Reuters expect to get in return?

If Thomson Reuters paid 10 times, logically, they should expect to gain at the same rate of return. This means by 2033, they should expect to earn $6.5 Billion from this investment. This logic only connects if the growth of paying customers remains at or above a 29.2% CAGR in the coming ten years. Now this gives us something to look for by August 2024 earnings season. We love to know: will demand grow?

Since consumers will get most copilots for free, professionals will likely want the premium stuff. Sophisticated users desire solutions that offer a complete package. This means that when we offer a pilot, the pros will also want a plane and an airstrip for takeoff. In short: building the infrastructure for pilots to thrive doesn’t come cheap. From that perspective, the value makes sense. In fact, the deal may even be a bargain. Heck, everyone will want to fly private eventually. Therefore, we aren’t worried about demand nor supply. However, what about distribution?


To circle back to my GPT-4 factor question on LinkedIn: it was a rhetorical one. OpenAI owns GPT, and Microsoft paid $11 Billion to push it onto every lawyer’s cockpit. Google, has a $1.5 Trillion market cap and arguably the deepest bench of AI brains. And they still haven’t caught up. So, becoming the Legal Copilot with just $650 million might be a brilliant move ten years from now. Note: Thomson Reuters had $1.3 Billion in free cash flow by the end of 2022. So it’s not like they broke the bank to broker this deal. They’ve been pretty quiet on M&A up until now.

Still, it leaves us wondering one thing: why didn’t Thomson Reuters go directly to OpenAI? FiscalNote did, and if you’re curious about how that turned out, watch their video on our TV channel. Stick around for the second video, showing us another interesting pilot. Sadly, that plane disappeared from our radar. After you’ve watched the video, you’ll understand why it may have been shot out of the sky.

I hope you had a pleasant flight, and a special thanks to our flight crew:

  • ChatGPT;
  • Voxscript;
  • Webpilot;
  • Pluginpedia.

Mixed Reality: Is Legal in A Supercycle of Growth?

Mixed Reality: Is Legal in A Supercycle of Growth? 1618 872 Raymond Blyd
Read time: 3 min.

Marc Benioff from Salesforce calls this moment in time a supercycle. While, the reports are mixed, the reasons remain remarkably subtle.


For those new to Legalcomplex: we missed our analysis in May, so this one includes June as well. We presented numbers at Futurelaw 2023 in Estonia and were asked to share slides. Meanwhile, Apple unleashed a new computing paradigm and made us nostalgic. Finally, we’ll explain our confusion about DocuSign’s latest earnings. Now, we always limit our posts to three minutes read time. It’s a discipline to suppress any delusions of grandeur. Therefore, this is our most dense analysis ever.


We presented a couple of spoilers in Tallinn. One slide on the size of the legal market in contrast to GRC or FinTech (Hint: it’s tiny by comparison). A slide about what lawyers and firms want to buy. (Hint: they rather build tech themselves). We delved into Europe and the Baltic Rim but started with AI. We had to because two days prior, Nvidia became a Trillion-dollar company. A reminder that lasting wealth usually ends up with picks and shovels. Next time you wear Levi Strauss, remember to read up on the 1853 gold rush. So, the spoiler? Profits from AI currently come from hardware, not software.

Bewildered? That was just a warm-up. Let’s address three more myths:

1 AI investment is taking off. Investments in AI have been dropping precipitously. In 2022, AI investments plummeted by a 26.7% decrease over 2021 as reported in AI Index Report 2023 by Stanford. Are things looking up this year? Nope, the downward trend continues, as shown in CB Insights AI funding for the first quarter of 2023.

2 AI will return on investment. The fact that investors struggle to find value in AI correlates with the cost of scaling AI. It costs OpenAI $700,000 a day to run GPT. We’re not debating the value. We’re just calculating how quickly it can return on investment. AI will increase efficiency, not profitability. Currently, it’s just too expensive to scale.

3 Legal AI investment is taking off. Surprisingly, it could. Despite macro trends, Legal AI funding held steady. The white line in the chart below reveals no big dips in the last three years. The chart cut-off is May 18th. This is just halfway through Q3, 2023. And this explains the drop at the end. As previously stated: Legal is Stable & Durable.


So what will Legal AI do? History, tells us that it will expand legal business and profitability. Remember what e-Discovery did for litigation? It allowed law firms to tackle bigger cases with fewer fee-earners. E-Discovery gave lawyers a forklift, so they could now bill for skyscrapers. More revenue with less overhead equals higher profits. This caused a stampede to join the e-Discovery bandwagon. We measured the impact of e-Discovery by several exits in Legal since 2001. See the video below and watch what happens after 2004 up until 2019.

However, after the HP-Autonomy $8.8 Billion bust in 2017, exit options for e-Discovery chilled. Therefore, the only way for the bigger ones was to go public. Now, if you look at stock prices today, and compare them to the initial stock offering. Well, let’s not rub it in and get canceled. We’re sticking to our principles and not name these. Better yet, I’ll offer a message of hope: “Buckle up those jeans, and remember what you are”.


This brings us to tell a tale of two legal technologies. Here’s a pro-tip: a shortcut to get a pulse on the legal market, is by listening to earnings calls. The question & answer (Q&A) is the juicy part. Note: the next three links jump to the mentions in the YouTube versions of the calls.

Dropbox narrative has two sides. First, the e-Signature struggle is still real, yet Dropbox did get a bump from Formswift: a legal doc platform. The reason was tax season. While the HelloSign acquisition remains a strategically important asset, it did not contribute as meaningful as Formswift. Neither has Docsend, another Dropbox acquisition. Why? Both HelloSign and Docsend, suffer from a severe drop in deal flow in many industries.

But not all segments suffer the same fate. Two weeks later, DocuSign earnings call comes with an upbeat message on contract tech. Now I’m baffled. However, we noticed a subtle but crucial difference between both calls. During the Q&A, Docusign singled out real estate as weak versus manufacturing and business services as strong. Ask GPT: what are business services? Among a short list is Consultancy, Legal, and Supply Chain. Also known as “Picks & Shovels”.

Bottom line: Dropbox won with Tax and DocuSign relied on Legal and several other ‘shovels’. Only looking at the extremes “Capital & Conflicts” will make you miss everything in between. Kudos to pro analysts on these calls asking questions. They help rookies like us to see when areas in legal deliver profits. So, Legal Tech, whenever you’re ready to harvest, grab a shovel.

Recap: mixed signals will remain since legal relies on seasons. While the tourists only enjoy the summers, the pros can weather any storm.

Five Tactical Tips That Will Wow Investors

Five Tactical Tips That Will Wow Investors 2528 1420 Raymond Blyd
Read time: 4 min.

Any investors would love to see growth with a moat in a startup. Realistic investors know the market conditions for that to happen.

Disclaimer: We co-authored this post with GPT-4 and persona X-Ray. X-Ray is generated with GPT by having it analyze our Study section. We loaded X-Ray with data from Spark Max and added specific expertise to boost cognition in certain areas. It took 102 prompts to get a result, so stick around to hear our thoughts.

Breaking Bad

Funding companies by investors has fallen off a cliff in the first quarter of 2023. Yes, it is bad but, it is not all bad. To illustrate, we created a unique view on investing in Legal. A view that looks at investors in founders. Based on this view, we generated tips for you.

This is a deep cut, so bear with us. Back in 2018, we revealed that the average number of investors per startup in legal was about five per company. Break down this number in mature and young companies, and you’ll see something different. The drop in participating investors isn’t as dramatic as the drop in the amount they invest. Moreover, we see a light increase for young companies. Better yet, fewer investors cut bigger checks at seed stage. How do we know?

The graph shows average investor count (green line) and investment amount (blue bars) for companies in the legal space. The left side shows mature companies receiving later-stage funding. The overlay chart is the same for young companies getting seed-stage funding. Swipe the image between growth and seed and see the difference. Yes, it’s deep but important nonetheless.

Five Unconventional Tips

There is more good news hiding in data and it’s usually counterintuitive. Here are five non-obvious tips:

  1. Identify ideal investor;
  2. Know your exit;
  3. Find better customers;
  4. Embrace lean operations;
  5. Demonstrate tangible growth.

1 Identify ideal investor

Currently, there are more investors sitting on the sidelines than at any point in human history. Institutional funds globally raised over a billion dollars a day to invest. Almost none of it is being deployed, but eventually, it has to. Remember, middlemen don’t get paid, when deals don’t get done. There is an easy way to identify the investors that match you, and you can surprise them with your pitch. So the steps are:

  • Find Customers who would also be willing to be your investors;
  • Locate investors Close to you and your principles;
  • Identify those with FOMO, who haven’t yet invested in but understand your market.

2 Know your exit

We’re now in a slow economy where two exit options became popular: mergers and acqui-hires. Mergers are a sign of a maturing market with slow to zero growth. Our tip: avoid those areas. This leaves option number two and a possible third. Being snapped up quickly or IPO big in about seven years happens under these conditions:

  1. Fast exits happen when you built a feature that is hard to duplicate.
  2. Big exits happen when you have a customer base that is hard to replicate

In both cases mentioned above, being flexible and free in your strategy helps. So what does the above average investor graph tell us? Fewer captains make for smoother sailing. If you are bootstrapped or have only one or two investors, the decision to exit is less complex.

3 Find better customers

If you decide to exit big, then current conditions are ideal. If you can grow naturally in a slow economy, you’ll launch like a rocket when things pick up. Natural growth comes from a sticky customer base. Sticky happens when your product is essential. Real sticky happens when your product is required by law. As legal, we serve many essential industries that need to be risk-free and compliant in order for us to trust them. Those industries need trust. Our society requires trust. So what is in very short supply and in hot demand? Trust.

The saying goes: Trust takes years to Build, seconds to break, and forever to Repair. That is how we view the business of legal: building and repairing trust. Yes, most get stuck watching the hourly rates of lawyers and thinking of them as fat wallets. Once you are able to move pass this, you may discover the bigger opportunities for the legal industry. Perhaps the biggest opportunity legal has is to build and repair trust between companies and consumers. It is a way bigger market, making them both better customers.

4 Embrace lean operations

It takes money to make money. Well, get used to the fact that there is no money. Before inflation, companies grew by pouring cheap capital into companies. If you missed the memo, that strategy no longer works. Now, everyone will want to conserve capital while maintaining revenue. Here’s the paradox: everyone will spend less while simultaneously figuring out to let others buy more. Economics force us to do more with less. In one word: Efficiency.

Ingenuity is a free, yet an extremely scarce resource. If we use ingenuity to gain efficiency, the result is usually Automation. Just in case, you also missed the other memo: we can now use this tool called GPT. Ok, I took it to the extreme by making it the co-founder for our new company. I’m just embracing it out of Necessity: the mother of all inventions.

5 Demonstrate tangible growth

This brings us to our final point: will (more) people keep buying? We’ve learned that pre- and post-pandemic provided different answers to this question. In our pod appearance and previous post we indicated that we’ve now entered a new era. This means we’ll discover new metrics to gauge growth across the globe. Despite the fantastic narratives you hear from formidable names, keep listening for numbers. When you hear a number, then watch for these two words: ‘usage’ or ‘adoption’.

Those numbers are notoriously hard to get real about. We use proxies to calculate usage of solutions in any area. We use capital raised, employee growth, traffic stats and even Adwords pricing fluctuations to find out what grows. If this last metric doesn’t make sense, then perhaps you’ve never had to calculate the cost of acquiring a customer. This goes back to another deep cut from 2019: The cost for acquiring a customer in legal is among the highest in the world. Therefore, no need to envy fat wallets. Like we stated in this video with a shrug: illustrating growth is easy, demonstrating is it hard.


Now, about using GPT-4: it is the best at producing boilerplate. It requires a lot of data and prompting to steer it away from default, which is looking for consensus. If you require something counterintuitive, you’ll need prompt engineering. So GPT gave us a starting framework and inspired us to…scrap its framework and start over. It’s unparalleled in research, but be careful with the facts and examples that it provides. GPT gets you started, but you need to polish it. Lots of polish.

In Hallucinations, we made the case that finding the extraordinary in the ordinary is GPT’s greatest strength. However, it needs our ingenuity and creativity to do it. For most cognitive tasks, humans are in a weight-lifting contest with a forklift. But with a forklift, we can build skyscrapers. So to build skyscrapers, a forklift requires us, humans, to imagine it.

With GPT, we can imagine and build mindscrapers.

Heroes: What Happened At My First Legalweek?

Heroes: What Happened At My First Legalweek? 1032 508 Raymond Blyd
Read time: 3 min.

I got to meet heroes. In the wake of the disruption the week before, we discussed the opportunities and threats facing the legal industry.


On March 14, 2023, OpenAI released GPT-4 and demoed live at the 19:30 minute mark, how you can be your own tax lawyer. This is the moment we promised to let you know about after our 2020 analysis: Will lawyers be replaced by GPT-3? Now, with this shadow looming large, I went to cross off one item on my bucket list: Legalweek by ALM. I had no plan, and no purpose except to explore and to experience. Here’s what happened.

We announced our World Tour locations and kept our dates stealthy. It’s a Surinamese superstition to be stealthy about travel. Just as we applaud every safe airplane landing we are in. However, I did mention Legalweek to a few friends, and they graciously invited me to meet. And that’s the first tip for all Legalweek rookies: meetings. No matter if you are a visitor or a vendor: the goal is to get meetings with people in person. We had 2 meetings planned before our arrival. On departure, we had completed 24 meetings in a three-day time span. We missed the parties since we were wiped out by 5 PM and awake at 1 AM every night.


Doing meetings almost made us miss the coolest part of Legalweek: exhibitors. There were three exhibition halls and we discovered the 3rd only later. These halls were filled with heroes, and I admired all who paid to make the trip to New York. Not only the sponsors and exhibitors, but also the visitors. Our rough estimate was 4000+ in attendance, all with one passion: working with legal. That’s why Legalweek was on my bucket list. Was it larger before the pandemic? Maybe. Will the next one be even bigger? For the prosperity of all, we sincerely hope so.

How could Legalweek grow? We need more heroes. Visibility is a valuable investment, and that’s why conferences are irreplaceable. However, deciding to show up would have been tough for most. Based on our calculation, most can not afford a big splash funded purely by revenue. The legal tech unit economics are like every other: products x price minus operations. We have fair benchmarks on both operations and prices per area. These benchmarks are generated using a large curated dataset. Given the pullback in spending by companies across the globe, the decision to attend took courage. Yes, even for those with access to outside capital.


Wandering Hilton, with these numbers on my mind, made this experience surreal. Because most of whom I met, and every vendor I saw, is a row in our dataset. Each is input to an equation on areas, segments, and geographies. Suddenly, the input had faces and voices and they talked to me. Imagine meeting movie stars at the Oscars. You know their movies, but you expect them to not know you. When I met Jack Newton, CEO of Clio, he said to me: I know who you are, and I like what you do. I had a hunch, since he had liked two tweets. Nevertheless, I was overwhelmed, and I kept that feeling until I landed in Amsterdam.

Why overwhelmed? The diverse faces and voices I met, in most cases for the first time, gave me hope. We knew we have enemies, now we know we have friends too. In all honesty, both originated from our ideas about the legal industry. We believe numbers matter and aren’t swayed by narratives. At Legalweek, we had those conversations with the people we met. It’s not all bad because the good news is usually hiding in data. Starting this Thursday, we’ll share the photos of our Legalweek adventure on LinkedIn. So follow us to see Heroes.

To be continued every Thursday…

Hallucinations: Should data make laws? Yes, and here’s why

Hallucinations: Should data make laws? Yes, and here’s why 1920 1080 Raymond Blyd
Read time: 3 min.

As a society, we evolve and make new laws. Laws are based on opinions we’ve formed after processing new information. What is new information?

TLDR: Thursday, 23 February, we presented our vision of the future of law. And our dream is data.


We’ll focus less on numbers this outing. The numbers aren’t pretty, so let’s not pile on. On the bright side, it seems we’ve hit bottom. We calculated a recovery around February. A calculation we shared back in August 2022 with Evidence in support: the US Federal Reserve only raised the interest rate by 0.25 this February. Previously, they raised rates by 0.50 and 0.75. Don’t pop the champagne because we are not an economist. Worse, most economists are actually sober about what lies ahead.

Another bright spot we shared with Law360 in early 2023: an avalanche of A.I. legal apps focused on consumers. All running on OpenAI. Talk about building a house in your neighbor’s backyard. This follows two other insights we shared. First, OpenAI is an operating system powering a new paradigm of tools. Second, by their own admission, OpenAI, and most apps build on top, will struggle to turn a profit. Remember, ChatGPT is a killer app, built by a non-profit receiving substantial backing from those with foresight. Realize, that we lack these ingredients in Europe and most other places except perhaps China.

Yet, working on something as fuzzy as “artificial intelligence” feels delirious. Note that the OpenAI dataset cut-off is 2021. You can ask ChatGPT to check this fact itself. So whenever GPT is faced with something after 2021, it will hallucinate. According to Wikipedia: artificial hallucinationis a confident response by an AI that does not seem to be justified by its training data”. This brings us to the point of this analysis: can we distinguish fact from fiction, and will we care? Welcome to a world of weirdness, which is our reality.


Now humans fake it until they make it all the time. Heck, the entire venture capital ecosystem is predicated on one principle: confidently project growth without proof of product-market fit. We closed 2022 with $496 Billion in capital committed to 696 funds looking to invest. This boils down to the craziest stat we’ve ever calculated: $1.3 Billion a day. That is how much is available for those looking for cash. Who’s getting a check? Here is a calculated answer. Contrast this with the reality that fewer tech companies are being founded. And the ones that already exist will struggle to grow.

Now that we’ve established that neither computers nor capitalists need facts to make decisions, the rest of us do, right? Yes, but we rely on computers that are funded by capitalists. Since we’re banning TikTok everywhere in the West, it’s obvious we don’t trust computers from communists. While spying is often offered as the reason, the underlying fear is seldom articulated: influence. With Brexit and Cambridge Analytica still fresh in our minds, it’s clear what guides our decisions: algorithms. In “A.I. the struggle“, the mini-documentary shows the stats and stories which illustrate the challenge. The dollars behind the data we need for our decisions are too overwhelming to dampen.

Surely, the law and lawyers can stop it, right? Actually, legislators created this problem in the first place. And lawyers are ill-equipped to handle any of it. Currently, before the US Supreme Court, there are a few cases around a law named section 230. This law allows those who create algorithms to not be liable for their impact. Pretty sure the lawyers confidently presented a legal argument, with no legal precedent, to sway the Supreme Court. The exchanges that followed revealed that those arguments weren’t convincing. As Justice Kagan admitted about the Supreme Court: “These are not like the nine greatest experts on the internet.”.


It’s likely that the courts will kick these cases back to congress to legislate. Herein lies the paradox, neither legislation nor litigation solves these problems. In “A.I. the struggle”, we pitted the Video Assisted Referee (VAR) against Goal-line Technology. If you watch Football every weekend, you know the drama with VAR. The VAR is nowhere as consistent as Goal-line Technology. Ultimately, that is the dream: rational, data-driven legal decisions. More than a copilot, much like an autopilot. Call it Autolaw. Are we there yet? Promise, we’ll let you know when.

Meanwhile, catch this clip, which we made six years ago to illustrate this legal industry journey. And promise us to think about the path our society is on.

Funding Legal 2022: A Tale of Three Totals

Funding Legal 2022: A Tale of Three Totals 1920 1080 Raymond Blyd
Read time: 3 min.

Funding in Legal totaled $5.38 Billion, we also have $3.43 Billion and $4 Billion. What’s the difference? Allow us to explain.

Funding Legal 2022

Funding legal is a multiverse of investments in different areas. Usually, the legal tech space is seen as a horizontal market for legal professionals. In reality, the influence on investments in legal comes from different verticals. Vertical such as Dropbox acquiring Formswift for $95 million. Before we travel through the different dimensions of funding, here are our 2022 numbers:

Funding Legal 2022
  • Raised: $5.38 Billion – down 23%;
  • Deals: 457 – down 2%;
  • Investors: 1017 – up 14%;
  • Average round size: $11.8 Million – down 21%;
  • Average seed check: $1.7 Million – up 35%;

This is private capital funding and excludes any mergers and acquisitions. These totals tell us that in 2022, more investors invested less capital compared to 2021.

The analysis is a filtered view of the legal tech space. A closer look at the image will reveal the filters we used to achieve this view. We left out a €700 million credit raise from a Dutch conglomerate. Also excluded are Tax Tech and Consulting (aka Law Firms). Curiously, we find law firms raising private funding more often.

Funding Legal Tech 2022

Law360 collects its own numbers. Their analysis, included the Topicus deal and Governance, Risk, and Compliance (GRC). GRC is a big space that we track separately. Here is a concentric circle chart of funding in GRC (yellow) and Legal (purple). You’ll notice that GRC has more-, and bigger circles. Now, are you ready to enter the multiverse?

Funding GRC 2022

The legal industry earns most of its money serving businesses. Essentially, legal helps companies get paid with contracts or avoid losing money in conflicts. Capital & Conflict analysis revealed the most lucrative work for legal professionals is generated at those extremes. However, most of the volume of legal work happens between those extremes. These are high-volume / low-value legal interactions. And the tech that supports those interactions attracts more capital.

Let’s pick one area which made our dashboards jump this year: eSignatures. While most view this as part of Sales or M&A. Electronic signatures extend way beyond legal contracts and contract management. The reality is that more areas drive investment into e-signature. You e-sign your package when it arrives or the company policies when you join. As a matter of fact: you sign freight, lease, loans, mortgage, insurance, and many documents in many areas. We sign documents to prevent conflicts.

E-sign is about prevention, and so is GRC. In 2022, Governance, Risk, and Compliance captured $36 Billion in capital and only dropped 4.5% in funding. This drop is far less than the broader tech market has experienced.

Besides prevention, we also have protection.

Funding GRC 2022
Funding IP Tech 2022

Let’s ignore the NFT madness for a moment. Last year we saw the copyright investment on top. This year, IP Tech alone captured $6.83 Billion and was up 32%. Yes, that is more than Legal, with Contracts, E-Sign, Tax, and Consulting combined.

… let’s pause and allow you to zoom into those numbers…we’ll wait…

To encapsulate the above in a little anecdote: Netflix’s new ad-supported tier had some hiccups after launch. A major reason is content licensing restrictions are crippling the free offering. Didn’t Netflix ask copyright cops to track down sign-off using contract tech? If your core product is copyright, these risks shouldn’t play a role (pardon the pun).

In short, Legal will rely more on GRC for growth with prevention and protection as opposed to deals and disputes.

Finding Deals 2023

One way to find deals is to follow the funding. Funding numbers and charts not only tell us the past, but they also help us project. As stated to Isha of we do not predict, we calculate. Now, we are able to offer something no one else can: projected deals for 2023.

The 2023 deals are projected based on the last funded date and burn rate. Due to the delicate nature of this data, we’ll select a limited set of customers to share this with. We will custom craft ten (10) reports with our famous line charts, last seen on Artificial Lawyer. You pick a segment or area like Legal or Contracts. You get an export with the names and dates of all funding, plus mergers for 2022 and the projected deals for 2023. On top of that, you get to pick over 34 specific charts to generate insights on.

Need this now? Check Spark Matter, for details on pricing, data, and delivery.

Will Investors Keep Investing in Legal? We Calculated

Will Investors Keep Investing in Legal? We Calculated 1920 1080 Raymond Blyd
Read time: 3 min.

The paradox of investing in a slow economy is that it forces investors to invest in slow growth. Now, where does one find slow growth?

Before we run our analysis on investors and investing, let’s set the stage. We received two significant signs this quarter: Salesforce growth slows, while DocuSign beats analysts. What happened? Software as a Service (SaaS) growth has peaked, but not all SaaS companies will suffer. Salesforce was a wild ride and a model for modern profitable businesses. What model is next? Stick around for the answer at the end.

In Bora Bora & The Bahamas.. 

Sam Bankman-Fried is arrested in the Bahamas after losing $17 Billion. Elizabeth Holmes defrauded investors out of $945 million and will serve 11 years in jail. Meanwhile, Adam Neumann received the biggest-ever check for a new startup. This after SoftBank lost $17 Billion on his previous one called WeWork. Collectively, those three misplaced about $35 billion of other people’s money. How? Now, we weren’t in the room when they pitched, so I won’t speculate on the state of mind of investors. Yet, investors should be taking smart, calculated risks. Clearly, there was no calculation, so it wasn’t smart. 

Sequoia Capital issued a rare apology for losing $150 million on FTX. This is an epic firm that made big returns on Google, Youtube, WhatsApp, and LinkedIn. Yet they aren’t a household name like Shark Tank’s Mark Cuban. While many in my circle love the show, I remind them that it is mostly fake. When asked, Mark Cuban admitted to losing massively on Shark Tank investments. The worst was seen partying on Bora Bora.

So Yes, if you fit a certain profile, you can get (away with) smart people’s money. 

..A Billion A Day..

Dude! It’s a recession, where is the money? Since January 3rd of 2022, we registered 574 announcements of new funds raised. This totaled $324 Billion in capital commitments. Basically, a billion dollars a day is set aside to pay founders. Let’s pause for a minute and take in the breeze of the Bahamas…

We can’t explain how this is even possible. I suspect the answer will be surprisingly simple. Perhaps committing cash to this cause somehow preserves it. Maybe prevents people’s savings from getting lost. Again, we aren’t smart enough to calculate how people commit capital. Here’s what we do know. In the announcements, we looked for the following: 

  1. Amount raised; 
  2. Type of fund e.g. Venture or Private Equity; 
  3. Location;
  4. Who they Target, e.g. young or mature companies.  

Especially that last point is of interest. Target tells us who’s likely lucky enough to get money. This is pretty straightforward: funds pick either a sector or a stage. For example, some funds will only invest in Blockchain or Biotech. Others aim for early or late-stage companies. Case in point: as a founder, you’ve probably got a call from someone asking for your revenue. If you answer none, they hang up. Those are Private Equity people. Nice and polite people, if you have at least $200k revenue annually. 

Hence, Yes. If you have income, you have a shot at a cash injection. 

..Keeps Legal Away

Out of this massive mountain of money, there is just a particle of investors with capital focused on legal. Worse, if you read our last post, you’ll realize that they aren’t all nice and polite. Don’t despair and remember the first chapter: It’s not you, it’s them. Better yet, here is our final bit of data. And this is historic. 

For a brief moment, in the 3rd Quarter of 2022 something unique occurred. The number of seed-stage deals in legal surpassed that of later-stage companies. Take a deep breath and let that sink in. Nobody we know anticipated that this could ever happen. Especially now when access to capital feels impossible. Actually, now only long-term capital commitments are feasible.

Why? There is little to no growth in this economy. Our last post analyzed those quick paydays, and these aren’t in abundance. That is why funds are forced to accept longer horizons. We calculated a while back, we know one sector which has a stable growth curve. Albeit slow, so less sexy. How? Long sales cycles are repaid with slow churn. Customers of legal tend to stick around. They are calculated

In closing: Yes, legal will still get money even if we aren’t sexy. We can still rock in the Bahamas. 

Disclaimer: this post wasn’t written by ChatGPT. Better yet, ChatGPT can not ever replicate this outcome. You need our model running on top of our uniquely labeled dataset. So ChatGPT can copy this text but can never deduce this model.

Therefore the answer is models. They are the new model.

True Value: What Makes A Successful Legal Tech Exit?

True Value: What Makes A Successful Legal Tech Exit? 1280 601 Raymond Blyd
Read time: 4 min.

Answer: selling your company (stock) at the right time to the right buyer. Getting an exit timing right gets some really angry with us.

TLDR: Exit options are limited as capital gets expensive. Yet, who is buying and how they are financing it tells us that options have shifted.


A quick recap of how we ended up here. Legalcomplex started collecting companies that impact the legal industry. Our collection is broader than the companies that serve only legal professionals. We started with tracking the total amount of venture capital invested. We added mergers, acquisitions, investors, and the number of employees. Along the way, we made many friends. Apparently, we also made some rich, and influential enemies.

Those enemies reside in two camps: we don’t like how you classify our ‘legal tech’ and we don’t like you…period. We have an ongoing positive debate with the first camp. That last camp wants me to not exist. Why is all this relevant? Well, we got a reaction to our insight on successful exits by legal tech companies. By the way, I keep saying ‘we’ because I represent a community. A large yet less vocal one. One that believes in numbers, loves how we display data, and supports why we do it.

Let’s start with the numbers and, we’ll get to the anger. We started looking at who, and how behind acquisitions. Here’s what we found:

  • 901 in deals where 892 were unique and 16 changed hands more than once;
  • $59.1 Billion paid out to targets (adjusted for inflation);
  • 11.9 average age in years.

This is our third analysis on exits, and I recommend checking The Study section for the one we did with Law360. This new analysis will highlight the backdrop of acquisitions.


Why the anger? There is no free money, so it is a lousy time in tech to look for an exit. Who’s looking? Founders and their investors. One is chill. The other one, not so much. Why? Well, big payoffs are off the table for the moment. Investors overloaded unprofitable companies with capital. Now, the people backing investors want their cash back. Why? An economy in recession is going to incinerate wealth. Specifically, the wealth created when banks gave near-zero interest-rate loans also known as free cash. This wealth was never supposed to exist.

Where did that free money go? If you were good at spreading dopamine, you could get a lot of free dollars. In general, that isn’t a bad thing if one of these bets pays off big. But here’s the problem: big payoffs happened in a bubble of excess capital. That bubble popped after 2021. As energy costs keep rising, people will be spending less. This drives down demand for all goods and services. All companies eventually suffer because there is little growth. Yes, everyone, including those that operate in the legal industry. Some will suffer less and, it depends on which area of legal you operate. There are still areas of brittle growth.

What do the numbers tell us? We can pick several angles to find growth. In the video, we see the popular areas. Another angle can be revenue, but let’s not get greedy. Let’s pick the average age of an exit after the company started. For geeks: the median age is 11.6 years. Now guess which type of companies lie below this median? Has the age increased or decreased over time compared to the average? Bottom line: what (type of) company will earn you a big and fast return? One which operates in areas with naturally fast growth.


It is our policy to be careful using names. We have empathy for those who build a business because it is really hard. Bootstrapping one is even harder. But bootstrap gives a bigger return to founders. Venture Capital (VC) backed companies offer a faster return. VC ventures artificially power growth, while bootstrap relies on organic growth. Now that growth is scarce, we see how VCs act when they’re off their medication called cheap capital.

Enter Private Equity (PE) firms that offer early retirement to founders. Specifically bootstrapped ones because they show evidence of organic growth. Of course, there are clever companies bargain-hunting for attractive tech and talent. All this pushes VC big payoffs further into the future as founders opt out early. So what options do companies have? Here are the possible exits, we have seen in no particular order:

  • IPO
  • SPAC
  • Acquisition by a Public Company
  • Acquisition by a Private Company or Law Firm
  • Acquisition by VC-backed Company
  • Acquisition by PE
  • Acquisition by PE-backed Company
  • Merger

Each option has a fingerprint that reveals what made the exit happen. And the smoking gun is how they actually pay for a purchase. We reported that acquisitions by private companies or law firms, usually do not disclose the transaction sum. One reason is that it’s a bargain buy of tech and talent. Another is that buying a revenue-generating company is really expensive. Blame this fact on all the fake capital floating in our economy. It caused to inflate the value of companies. An inflated value calculated from expected exponential growth. Exponential growth, calculated using artificial growth.


So are big exits impossible? Nothing is impossible, the question is big, for whom? Using the above framework, we’ve seen which exit happens more often. Which exit has the highest outcome? We can also track who is likely to acquire, looking to get acquired, or merge. In reality, few businesses are able to finance an acquisition from their balance sheet. That’s why we recently noticed a shift in two directions: where capital is coming from and where it is ending up. Ultimately, companies with low operational and capital expenses now get some breathing room. A room with fewer dope dollars and artificial growth. The space where we can spot true organic value.

Because we smell the burn from miles away, we can more accurately calculate the distance to the fire. Even though the reaction was needlessly vicious and inaccurate, we empathize with the anger. We do it out of love.

Editorial note

Usually, we load our analysis with hyperlinks to additional information.

This analysis has only one link.

Almost forgot:

The video above contains 1241 easter eggs.

One is about the future of our company and one is about the Marvel Universe. The other eggs tell the story of every single company that raised a disclosed amount of capital.

Stories made possible by true love.

GRC: Signs of Brittle Growth For The Legal Economy

GRC: Signs of Brittle Growth For The Legal Economy 956 499 Raymond Blyd
Read time: 3 min.

Growth in legal is noticeable in the earning reports by public companies and the funding patterns in private ones. What are the signs?

Recap: Growth in legal is picking up, but it relies on only a few areas in Governance, Risk management, and Compliance (GRC). This growth is fragile and depends on the price of energy.

Our latest chart on Artificial Lawyer, paints a depressing picture. To help us understand the pain, we answered some questions in our Capitals & Conflict. Essentially, the legal economy is a pendulum, which swings from deals to disputes. Between both destinations lies a string of risks the world wants to weigh. Those risks are the less sexy revenue boosters for both lawyers and legal technology. These boosters appear in funding and earnings. Let’s look at two of them.

Case in point: investment in procurement and legal spend analytics for corporate counsel is steadily increasing

Legal Tech Funding Continues to Decline – Artificial Lawyer

First Sign

We recently ran a report for a customer on the state of European Legal Tech. One of their requests was to show the new growth areas. First, you need a history of data to compare earlier funding with current ones. The algorithm then captures areas that see sudden rushes of fresh capital. Geeks will recognize these principles as standard deviation or variance. They are tools to tell us what suddenly goes up or down. And they told us that managing supply chain spending was a top priority for everyone. Supply chain means goods, services, and labor we need to produce. Supply chain impacts the legal economy because many want to:

  • Curb unpredictable spending like on legal support;
  • Draft better terms of services to receive supplies faster and cheaper;
  • Improve labor relations with better agreements.

This results in more demand for solutions that help you manage the above risks.

That sounds great, but why should we believe Legalcomplex? Fair question and one we asked ourselves every day. If you have data, you should rely on it. Are you scrappy, like us? A free resource you can tap into is the public stock market. We shared our top seven of the 31 stocks we tracked. Since we don’t want to anger the purists, we keep companies like Coupa, outside the thirty-one. This business spend management stock popped after reporting record earnings despite inflation. This Yahoo Finance video reports the Coupa surprise and the UiPath free fall. UiPath is a legal automation challenger and growth area according to some purists. Fun fact: UiPath gave Icertis a shout-out on their Q2 2022 earnings call.

What is Icertis? That is the #3 private legal tech company in the USA based on total funding raised. See more global rankings on Spark Map.


Public earnings are a late indicator of trends. The nuggets are usually hidden in how those earnings came about. This brings us to another surprising report by Australian Family Lawyers. This insider reported a 68% growth in full-year earnings. Not all growth is the same. Organic growth comes from a natural increase in demand, as opposed to cutting costs. The few publicly listed law firms provide us with this unique glimpse into what drives their growth. As previously mentioned, we can not share their deck, so we’ll just condense their tailwinds:

  • New (marital) legislation expanded the client base;
  • Economic pressures lead to more disputes;
  • The pandemic has reformed courts to process more disputes.

The AF Legal Group also elaborated on the use of technology for business development. Specifically, how they use behavioral analytics. AF has optimized its sales pipeline to capture customers based on their behaviors. In plain English: if someone needs legal support, they have the tech to reach them. Let’s be honest, the area lawyers would like to be more efficient, is how they can bring in more business. Let’s be realistic, the cost of acquiring a customer in legal is the most expensive for any industry. If you can not bring those costs down, any business is doomed.

If either one of these escalates, we will be in for some really tough times by February 2023

CLM Prices See the Most Inflation as Vendors Look Beyond Legal –

Final Warning

All the above insights are free for everyone to find. Like the glimmer of good earnings, DocuSign reported this quarter. Those numbers can change based on whatever is happening in the world. The one clear factor that is pressuring us all is our need for Energy. No need for fancy dashboards to watch inflation, go to any store and check the price of real meat. Vegetarians and climate-changers already warned us for different reasons. Price increases ripple throughout our lives, and legal is no exception. Essentially, legal is a luxury that can only raise prices when it has tailwinds. And the economic climate can change those tailwinds into headwinds.

In a world where the essential becomes expensive, luxury is the first casualty. This delicate growth the legal economy enjoys will evaporate once energy prices edge higher in Europe. This means: take out your economic compass and navigate towards growth. Currently, growth is visible in GRC, and you’ll see it in the second part of the video below.

They say: seeing is believing

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