C2V February Notes From The Trenches

Feb 25, 2026

Welcome friends! Well, we’re not sure if two absolutely electric US gold medal hockey overtime wins over our friends to the north are an impossible act to follow, or if everyone’s lingering adrenaline highs will make just about any content sound good, but into the deep end we go.

It’s been a couple of quarters since our last VC/startup macro data check-in, so with final 2025 numbers now in, we figured it was time to stock of where things currently stand.

So while our poor Canadian readers lick their wounds after those hockey heartbreakers and our first ever Olympics curling scandal, let’s start our review of 2025 VC/startup trends with the fun part, the exit market (all data from the Pitchbook-NVCA Venture Monitor unless otherwise noted)…

A Demise Greatly Exaggerated

While this is not the first time we’ve covered the counternarrative strength in the startup exit market (with a historically favorable supply and demand imbalance), we’re now officially changing its designation from “encouraging signs” to “full-blown trend”.

Not only are we now in 3-year upward trend in both exit counts and dollar volumes, but hints of a meaningfull acceleration seen in early 2025 continued throughout the year. In terms of total exit value, M&A and PE buyout segments both had their second-highest year on record (just slightly below the 2021 bubble peak) and were 124% and 59% above 2023 lows, respectively.

The IPO market, of course, remained well under its 2021 peak (it may be a while before we see those levels again) and was still roughly 40% shy of 2019 and 2020 totals. That said, IPO volume in 2025 was 4x higher than 2023 lows and the fourth-best year on record in terms of total volume.

While the accelerating improvement in headline numbers is certainly a welcome development, what should really have us all excited is the underlying supply and demand trend that has aboslutely exploded in favor of startups and their VC backers (well, some of their VC backers, anyway). Absent any significant external shocks, this should lead to even more (and perhaps, even faster) improvements in these headline numbers over the next year or more.

Exceptional Demand Indications

The most obvious indicator of the market’s willingness to buy mature tech startups (and not finding enough of them to buy) is, of course, skyrocketing exit valuations. Weighted average values are up 4.1x in just the last two years, and more than double the prior 10-year average (12% higher than even the 2021 peak!), and we’ve seen similar strength in each of Pitchbook’s three exit categories as well.

The median 2025 value for M&A exits (which generally make up 70-75% of all startup exits) were 2.7x above the trailing 10-year average (+2.2x YoY), PE buyouts were 1.6x their 10-year average and 3x last year, and IPO medians were 3.1x the 10-year and 3.3x last year, crossing the $1 billion mark for the first time (and a full 50% above their 2021 peak).

The breadth of this trend is perhaps even more encouraging. According to Crunchbase, there were 57 startup exits of $1 billion or more in 2025, behind only 2020 and 2021. 2025 was also a record year for $1 billion+ startup acquisitions (i.e., exits other than public listings) and acquistions as a share of total exits were second only to last year, nearly 3x their share of exits in 2021.

The IPO market also looks quite favorable in terms of revenue multiples, with trailing 12-month price-to-sales ratios for venture-backed IPOs at their second-highest annual average of the past decade-and-a-half, behind only 2021 (and 41% above the trailing 13-year average).

Continued Supply Constraints

Of course, demand is only half of the equation and a dearth of willing supply remains evident as well. While of course, we can’t know for sure what’s going on within late-stage funds, it’s not hard to infer from any number of dat points that despite record median exit prices, these portfolios’ remain littered with companies marked well above where they could exit today.

Steep Secondary Discounts

The vast majority secondary market clearing prices remain far below peak funding rounds. Price data from one of the major secondary platforms we look at has remained more or less the same for 3 years now — average prices right around 50% of prior funding rounds, more companies trading at 80%+ discounts than those trading at premiums to prior funding rounds, and those few premiums generally in the single-digit percentages.

IPO Loseses

Of the seven largest tech IPOs in 2025, five priced lower than the companies’ last private funding round (three saw losses for the last two funding rounds), and we’re talking about IPOs ranging from $6 billion to $23 billion. Furthermore, these final rounds were generally larger than all the prior rounds combined, so it’s likely they involved a huge percantage of the middle-of-the-alphabet fund set.

Incidentally, the early-stage investors in every one of these deals made an absolute killing — on the order of returning several multiples of their entire funds in one exit (we’re just saying…).

Stale Holdings

We’re also now at a historically low percentage of Series C+ deals from 2020-21 that have subsequently exited and 41% of all “unicorn” companies haven’t been back to the funding market since 2022.

Of course, this could mean that they abruptly shifted from every-9-months raise/burn cycles to growing super efficiently, and they just don’t need the capital. It could also mean they’d rather limp along indefinitely than raise a down round. We’ll let you decide.

Beginnings of a Spring (Portfolio) Cleaning?

This is admittedly a bit of reach but…

The aforementioned losses on giant IPOs, while disastrous for their late-stage backers, are good for the industry as a whole, freeing up capital to be reinvested in stages with better return profiles and more import to the overall ecosystem (read: Pe-Seed to Series A/B funds). If that’s where the recycled capital goes, that is (more on that below).
The ratio of new funding rounds to exits dropped dramatically in 2025, from a prior three-year average of 12.4x to 9.0x, a 10-year low, as exit counts have steadily climbed over the past 3 years, while new deal counts remain roughly flat.

So, we are at least heading back toward historical cashflow dynamics (if somewhat slowly).

Deal Activity

Despite (as noted above), the number of startup funding rounds remained more or less flat for a third year, total deal value roughly doubled year-over-year. This is, of course, due to the heavy late-stage VC concentration in Big AI companies that we have discussed in prior macro venture commentary, with 50% of 2025 startup funding going to just 0.05% of funding rounds (11 funding rounds made up 41% of all Q4 investment).

Valuation Reflation

As one would expect, the combination of mostly flat deal counts and a spike in funding has sent valuations from Series A and beyond back to the 2021 stratosphere. As was the case then, the most extreme move has come in the super late-stage, with Series D+ median valuations now just shy of those 2021 peaks.

If anything, though, this may understate the current Series D+ environment, as average valuations in this segment (at $5.3 billion in 2025!) more than tripled YoY and were 2.3x their 2021 peak (which was, itself, double the prior high water mark).

To put this in context, in the past 6 years there have been a total of 18 VC-backed exits large enough to return 3x this funding round average, 10 that would have returned 5x, and 2 that would have returned 10x. In 2025, there were more than 1,000 Series D+ funding rounds.

So, just to recap:

From 2020 to 2022, median Series D+ valuations more than doubled, more doubled again, then plateaud (-20%), before a (very) brief reset.
In 2024 and 2025, there were more $5 billion-plus IPOs in which investors in the last one or more funding rounds (generally Series D or later) lost money than those in which they made money, and the average positive return was less than 3x.
We have a record number of $1 billion-plus startups (by a mile) unwilling or unable to either exit or raise new capital (presumably to avoid having to mark down those 2020-22 valuations on a realized or unrealized basis)
In 2025, Series D+ valuations have bounced right back to peak 2021 levels (if not well past those levels), only with a much (much, much) higher concentration in the highest priced companies.

Do with that what you will.

Last but definitely not least…

VC Fundraising Reset (Sort Of)

On the bright side, new mega-fund capital took a considerably smaller share of overall VC fundrasing in 2025, with that money distributed among every other size bucket (even the true early-stage, sub-$100mm segment!).

It’s a start, anyway. Let’s hope we can keep it up.

On the less bright side, despite a slight 2025 uptick in funding for emerging managers (those with fewer than four funds) relative to experienced managers, we remain in a 6-year trend of capital rotating away from newer VCs.

Remember when the core ethos of this sector was backing novel ideas, bold, outside-the-box thinking, and assymetric return profiles with exceptional upside? Sigh.

(Yes, we’re talking our own book here, but it doesn’t mean we’re wrong)

Matt sat down with Scott Kelly (Emerging Managers Podcast) to unpack C2 Ventures’ “dirty, dull, and dangerous” thesis — not because the startups are boring, but because the customer bases (manufacturing, healthcare, heavy industry, etc.) have been chronically under-invested in modern software and automation.

A few themes came through loud and clear: C2V backs early-stage SaaS and selective robotics where the customer ROI is obvious and immediate, and where founders typically lived the problem before building the solution. On robotics, Matt emphasized discrete use cases that reduce edge cases (he used Somatic’s autonomous commercial bathroom-cleaning robots as a great example) and was candid that “true autonomy” is still rare.

On AI, Matt’s take was refreshingly un-hypey: AI isn’t “the product,” it’s the engine (or a feature) inside software that mirrors real-world workflows for non-technical users. He also shared why C2V stays disciplined on valuations (even during bubble years) so the power-law math can actually work, plus a sharp perspective on why emerging managers and focused funds can outperform mega-funds that have to deploy huge checks at premium prices.

Avol raises $3.8M to deliver organs and blood to hospitals

St. Louis-based Avol Aerospace is using electric drones to transport urgent medical supplies like organs and blood to hospitals, and the startup's unique aircraft design can deliver these critical items up to 11 times faster than traditional methods for the same cost.

man in white dress shirt holding black pen

Operatory Subscription Model for Dental Practices

UptimeHealth (portfolio) teamed up with Dentalez and Darby to launch TotalOp — a subscription model that bundles key operatory equipment with monitoring, maintenance, and repairs into a single monthly fee.

The pitch: less upfront capex, fewer surprise breakdowns, and lower downtime, powered by UptimeHealth’s asset management platform and Dentalez’s predictive alerts.

Getting a GRIPP on the Operation

Today’s farmers are constantly looking for ways to improve their operations, whether it’s new technology or ideas that have proven to help others. And recently at the Top Producer Summit held in Nashville, a company called GRIPP out of Wisconsin was there on behalf of AgLaunch of Tennessee to showcase how a simple idea is helping farmers keep better records.

How Two Years of Engineering Work Almost Killed Civ Robotics

Tom Yeshurun originally built the product around an aerial drone because it was technically exciting — then US customers immediately said, “Cool idea, but we’re afraid of drones. If it’s a ground robot, we’ll buy.” He scrapped the work and rebuilt it for autonomous ground robots.

The bigger mistake: early validation happened in Israel/Europe, where surveying is often subcontracted — but in the US, EPCs/GCs frequently do it in-house, so the buyer, ROI, and sales motion were totally different.

Now Civ runs on a simple rule: 1 customer asks → log it. 2 ask → build it. 3 ask → should already be done. Customer pull beats engineering push.

A person writing on a piece of paper with a pen

BriefCatch Just Announced They’ve Acquired WordRake.

WordRake has been a go-to editing tool for years, especially inside Microsoft Word, for lawyers and other pros who care about clarity and concision. The logic here is clean: combine WordRake’s sentence-level editing with BriefCatch’s document-level analysis (structure, strategy, persuasion) to help legal teams write tighter briefs and stronger arguments.

Eden has two open roles

Growth Marketing Manager and Senior Account Executive

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C2V January Notes From The Trenches

C2 Ventures

Jan 29, 2026

Welcome friends! A very happy new year to everyone.

Since we covered the high points of where we think things are headed in our 2026 predictions piece last month, we thought we’d just do a quick roundup of (mostly) timely news items, with an unintetntional concentration in an area we rarely delve into – the EV/mobility space (but don’t worry, we wedged some AI stuff in there too).

Where else would one start in talking about EVs and the latest in mobility innovation…

Tesla’s Sales Stagnation, the “Elon Premium”, and Leaning Into Strengths

For years, Tesla enjoyed the rare combination of explosive growth (41% annually from 2019 – 2023) and exceptional operating efficiency (gross and EBITDA margins at or well ahead of industry leaders). For years, Tesla has also traded at a truly staggering premium relative to its auto manufacturing peers. While its price-to-sales and price-to-EBITDA multiples were hard to justify even with the exceptional performance, at least there was exceptional performance to point to.

Since 2023, however, growth has ground to a halt (+5.5% annually over the past three years and -0.6% over the past two). Margins have also come in significantly, remaining in the top tier of the industry, but no longer a tier unto themselves and yet, the exceptional premium hasn’t changed at all. In other words, by the numbers, Tesla is an excellent auto company, trading at 2 - 3x the sales multiple of the average high-growth software company.

Of course, the real justification for this premium has always been the notion held by a large number of people that Elon Musk’s genius is so comprehensively far above that of every other person on earth that they couldn’t afford to miss having a piece of the action.

To be clear, this is not a knock on Elon. As an innovator and (perhaps more so) an operator, he certainly deserves a premium, but to this degree?

(Quick aside – while we appreciate that nuance, reasoned/balanced opinions, and middle-ground are relics of the 20^st century (sigh), you really don’t have to be in either the “everything Elon touches turns to gold” or the “Elon’s a sham” camps. Seriously, this is not required. You’re allowed to see the good and the bad. Both are right there in front of you and (if you ask us) you do not do yourself much credit by planting your flag at either extreme.)

To quickly illustrate this point:

The Good: Tesla
The Great: SpaceX — an objectively incredible achievement in all respects, having literally turned outer space into a viable green space for all manner of commercial enterprises (honestly, it’s hard to overstate how audacious and impressive an achievement this company has been).
The Mid (as the kids say): The Boring Company — essentially a glorified construction company, that for some reason also makes flamethrowers.
The Bad: Twitter/X — an unmitigated disaster, to the point where Musk had to jam xAI investors with it to avoid being foreclosed on by creditors.
The Undetermined: xAI — It has certainly had a choppy start, with next to no revenue, an almost unfathomable burn rate, and a product that appears to be quite a ways behind the OpenAIs and Anthropics of the world. But at this point, it’s also far too early to really have much of any idea of how the LLM race will shake out (speaking of xAI and jamming companies with cashflow problems into companies with burnable cash, though, while we’re not sure we buy this prediction, it’s an interesting read nonetheless).

Getting back to our point here, would Tesla looking more and more like just a top tier automaker have put the Elon premium at risk? Probably. Will the recently announced abrupt pivots into robotaxis and humanoid robots (explicitly at the expense of the EV business) solve that problem? Even if it means a combination of a lot of new spending and further stagnation of the auto business that significantly reduces profitability?

Well, Tesla’s Wall Street analysts’ 2026 projections (courtesy of Bloomberg) would suggest (at least for now) that it will, and then some (this degree of divergence between earnings and price projections is certainly not something you see every day):

While preserving Tesla’s premium valuation isn’t trivial (Toyota’s multiples applied to Tesla’s financials would result in a ~95% drop in Tesla’s stock price), to us, the more interesting questions are:

Is the big pivot really the best thing for the company long-term or just a hastily applied stock price Band-Aid?
Was there a better way to thread this needle without assuming the risk of a wholesale pivot and potentially squandering years of work building a huge lead in the EV space?

We’ll leave the humanoid robot aside for now. Tackling that is way too much of a digression, even for us, but this is an interesting, related take on the current hype-to-functionality ratio of various new products that’s definitely worth a read.

Focusing on the robotaxi business, while Waymo is certainly not going to have a permanent monopoly in the space, how realistic is it to think a viable competitor will pop up overnight (or even over a couple years’ worth of nights)? Initial reports of Tesla’s robotaxi progress in Austin are mixed at best and certainly give off a general air of something that’s been hastily slapped together to back up unrealistic promises (we would also highly recommend checking the source of any “reporting” here, as there are a couple of breathless worshipers with large followings and no scruples who are behind the most glowing “news”).

That said, there’s no reason to think Tesla couldn’t get there eventually, but is aiming to build and operate that first real Waymo competitor from scratch the best way to leverage Tesla’s strengths?

They have the cars, they have the cash to invest (as long as they don’t buy xAI), and they have organically collected a huge amount of the exact type of data needed for training AV operating software. But this endeavor also requires a substantial reallocation of cash and personnel focus, not just to building, but ongoing operational support, so much so that the company has publicly acknowledged it will require stripping pretty much all investment out of its core auto manufacturing business.

On the one hand, it may very well pay off and maybe in five years xCab or whatever will be the market leader. On the other had, it might result in a middle-of-the-road player in a highly competitive robotaxi market, sitting alongside a deteriorating EV business that is being lapped by a slew of new and rapidly growing competition from both traditional automakers and startup pure-plays (Rivian, Lucid, etc).

Most importantly, though (to us anyway), it seems like a waste of Tesla’s incredibly valuable brand and best-in-class manufacturing operation, both of which took years to develop.

While we appreciate that the old adage, “If you can’t beat ‘em, join ‘em” is anathema to 50 years of startup ethos, leaning into a company’s (and founder’s) strengths is also a core pillar of that ethos. What if instead, Tesla could take advantage of this new self-driving taxi phenomenon by leaning into its strengths, rather than kicking them to the curb in a wholesale pivot?

Tesla is world class at two things, efficiently building high-quality cars that people want to ride in and collecting data on every movement of those cars. As it happens, two of the three primary things robotaxi companies need in order to build, operate, and scale their businesses are cars and driver data. Is it too simple to suggest that they just partner with Waymo (or any other current or future competitor) to provide cars and training data?

From where we’re sitting, this has a huge amount of upside, potentially more than the pivot, since this would also enhance the core auto business, not kill it. It would also require minimal additional spending (and substantially all of that would be accretive to the core business anyway) and would produce immediate, high-margin returns.

In other words, follow the lead of the company that leaned into its strengths to provide the third thing that robotaxi companies need – software to manage the scheduling, routing, and rider interfaces.

We’ll get to that, but speaking of Waymo…

Is Waymo Actually Underrated?

Sixteen years, mountains of data injested, and countless hours of training and testing after its inception as a highly speculative and ambitious project within Google, Waymo delivered 14 million driverless rides to customers in 5 cities in 2025, three times the prior year’s total, and infinity times the number of autonomous rides in the entirety of human history up until 2015.

Even as recently as 20 years ago, this was the stuff of science fiction. It is a truly extraordinary milestone in human innovation, arguably even one of the top 10 or 20 ever and yet, the response seems to have been a collective shrug.

Shouldn’t we all be much, much more excited about this? Is the relative malaise a product of how long we’ve been hearing about self-driving, and/or the number of grandiose predictions around it that fell flat (none of which actually came from Waymo, incidentally)? Are we all just numb from the onslaught of content we’re now subjected to on a daily basis?

Who knows, but Waymo, consider us awed by this achievement. It is truly exceptional. You may take a bow at your leisure.

Now, whether Waymo’s rumored $100 billion fundraising round valuation is a shrewd investment, well, we won’t belabor this one, having written extensively about the perils of insisting valuations don’t matter. Suffice it to say, a company’s potential upside stops mattering the minute you decide to pay for all of that upside upfront, and this projected hundred-billion-dollar valuation is 40x the revenue these same folks are projecting Waymo will generate 5 years from now. Do with that what you will.

Speaking of Waymo, leaning into strengths… and Uber…

Is Uber in the Early Stages of a Future Business School Case Study on Adapting to Competition

Robotaxis pose no bigger threat to anyone than they do to Uber (and Lyft). A competitive service that takes in 100% of the fares it collects rather than 25-30% will, at scale, be virtually impossible to compete with. Faced with this reality, Uber could have gone full-Tesla and thrown everything into trying to rapidly piece together a competitive product (and it seems they considered doing just that for a time).

Instead, realizing that one of the major parts of a successful robotaxi business, the software for scheduling, routing, and interfacing with riders, happened to be their core strength, something they’ve already spent years building, testing, and refining, and into which robotaxi companies could seamlessly plug their cars, Uber has now inked partnerships with Waymo and other self-driving car companies.

So, instead of spending billions scrambling to put a competitive product on the road, essentially pivoting the entire business to something that may or may not even succeed, or simply watching their business slowly erode, they will maintain their core business, avoid a huge self-imposed cash crunch, and profit handsomely from the growth of this market right alongside the companies that could have been their undoing.

Future MBA candidates, when we see you out in the field, please just remember who gave you the head start.

Last but not least (pun absolutely intended)…

Is Apple Really Striking Out on AI or Are They Potentially the Smartest People in the Room?

Big grain of salt with this one as we have no inside information nor have seen a word about this in open source (i.e., this is pure speculation)… but is it possible that Apple isn’t woefully behind, missing the boat on, and/or in AI-denial, as most of the commentariat seems to think? That instead, they see the same bubble we (and many others) see and (unlike most others), are patiently waiting for it to collapse so that they can then scoop up the best companies/assets at pennies on the dollar?

We have touched on the growing AI bubble a few times in the past year or two, but to reiterate, the bubble is not about the technology itself, it’s about the prices being paid (and to some extent, how indiscriminate the choice of products has been). To be very clear on this, we have no doubt whatsoever that this technology will be at least as transformative as the rise of the internet was 30 years ago (perhaps significantly more so). But much like that early internet fever, we believe this AI craze has gotten far too hot, far too fast, and a substantial reset is coming (and is, frankly, necessary).

We have also previously written that, just like in the post dotcom bubble, we believe anyone with cash to spend will see their patience rewarded, not only in getting to buy great assets at distressed prices, but also in getting additional insight on the viability and demand for different products (and different versions of products) based on what survives the initial shock and what immediately disappears when funding stops being infinite.

Is it possible that the leadership at Apple simply remember those who waited for others to pour billions into Global Crossing’s infrastructure buildout (all the way up to a $50 billion peak market cap), were eventually able to reap the benefit of those assets at a 94% discount? Or those who waited for Amazon to decline, coincidentally, also 94% from its peak, saw their investment increase more than 500x over the next 20 years? Or those who watched Pets.com crash, had their initial reservations confirmed, and never gave it another thought?

Again, this is pure speculation, but in its 40+ years, Apple hasn’t really ever missed the boat on the potential of a new technology (more often, in fact, they’ve been the boat), so it seems unlikely to us that they’re just letting the potential of AI pass them by either. Just food for thought.

Chris caught up with two of C2V’s earliest founders — Cameron Hendrix of Magellan AI and Shilp Agarwal of Blutag (both 2019 vintage). Great people, strong products, and the steady, high-integrity execution we love to see.

Joined by analyst Jamie Redington, and a big thanks to Charlie Stephens at Fidelity Private Shares for convening the group. This is what the C2V community is all about.

View post.

Always great to see our 2026 tech predictions picked up by AlleyWatch.

Huge thanks to the team at Relevanz Public Relations and Steve Stratz for helping get this in front of a broader audience.

This is our 8th year publishing predictions, and we try to keep the scorecard honest — sometimes we get it right, sometimes we miss — but the goal is always to call things as we see them, not where the hype wants them to be.

Acquisitions Are Back, But Exit Math Still Matters

Chris is seeing signs that M&A is loosening up in 2026, pointing to Capital One’s acquisition of Brex as a signal that large strategic deals (and broader PE activity) are starting to return. He also flags a common misconception: headline exits don’t automatically mean everyone “won” — when prior private valuations were much higher, some late-stage investors can end up with little or no upside. The takeaway: the cleanest return potential is often built early-stage, where ownership and exit math can actually work.

Impilo Doubles Operational Capacity with New Warehouses in Philadelphia and Phoenix

Impilo announced major warehouse expansions in Philadelphia, PA and Phoenix, AZ to support rising demand and long-term healthcare partnerships. The new facilities will roughly double operational capacity, improving inventory management and distribution efficiency across a broader geographic footprint. The Phoenix warehouse is already operational, the Philadelphia site is expected to be fully online in Q1 2026, and the company plans additional expansions later in 2026.

red yellow and green trash bins — Photo by Nareeta Martin

WATS Sweepstakes Offers 12 Months of Free TRUE Waste Data Processing for One Facility

WATS is running a sweepstakes for North America–based facilities pursuing TRUE precertification, certification, or recertification by the end of Q3 2026, offering one winner 12 free months of waste-data processing for a single site. Eligible applicants must be actively managing 4+ waste streams and have a TRUE reporting cycle beginning August 2025 or later. Applications are open Dec 5, 2025–Jan 23, 2026, with the winner notified by email by Feb 27, 2026.

Reade more.

Gripp Rendezvoo Wins 2026 AE50 for Its New “Equipment Relationship Management” Platform

Gripp announced that Rendezvoo, billed as the first Equipment Relationship Management (ERM) platform, has been named a 2026 AE50 Award winner. The product focuses on the equipment asset as the organizing “source of truth,” helping OEMs, dealers, and operators align on the same timeline to resolve breakdowns faster and keep preventive maintenance on track. Rendezvoo combines real-time repair status, maintenance plans/reminders, in-conversation access to manuals/parts info, centralized communication, and field-to-factory insights to improve service outcomes across mixed fleets.

man writing on paper — Photo by Scott Graham

BriefCatch Raises $6M Series A to Expand AI Products and Pursue Disciplined M&A

Legal writing platform BriefCatch raised a $6M Series A led by Full In Partners, citing strong momentum including 126% net enterprise revenue retention and growing adoption across major law firms and courts (nearly 60 AmLaw 200 firms and many state/federal courts). The company plans to use the funding to accelerate AI product development and a targeted acquisition strategy, with the long-term goal of building a single, Word-native AI platform for elite legal writing, editing, and research. Founder/CEO Ross Guberman said Full In stood out for quickly understanding the technical roadmap and vision, and noted recent launches like AI-driven citation correction and a context-aware writing advisor.

Boostr + Passendo Partner to Centralize Newsletter and Email Ad Operations for Publishers

Boostr announced a strategic partnership and integration with Passendo to help publishers manage, forecast, and execute high-value newsletter/email ad campaigns directly inside the Boostr platform. The joint solution aims to give revenue teams a single source of truth by centralizing inventory, streamlining workflows across Sales/Ad Ops/Rev Ops, and feeding accurate performance and revenue reporting from Passendo into Boostr. The integration is available immediately to joint customers, positioning email as a more scalable, trackable, high-margin channel alongside display and native.

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C2V December Notes From The Trenches

C2 Ventures

Dec 22, 2025

Welcome friends! A very happy holidays to you and your families, and many thanks to each of you for another year of loyal readership. We can’t tell you how much that means to us, particularly as (if the hyperbolists are to be believed) every newsletter could be our last before we’re replaced by AI.

Just kidding, we’re not going anywhere. Even if we could be replaced, why would anyone waste the resources doing it? That would be like punting on teaching AI models to do math in favor of making deep fakes of Stephen Hawking skateboarding. Surely those harnessing this new power are better than that. Sigh.

But the pitfalls of putting amoral, spoiled children in charge of… well, just about everything, is a problem for future newsletters because (as our long-time readers know) December is prediction time!

As always, before we dust off the crystal ball, let’s look back at how we did last year.

2025 Prognostications Review

Tough year for crystal ball at C2V HQ, as only went 5-4 on our 9 tech-specific predictions, and fell right on our faces with the bonus (non-tech) prediction.

Let’s take a look at each in order (these are all truncated to save space; you can find the full version here):

The electrification of everything (everywhere but the US)

Big win out of the gate. Asia’s dominance in production of EVs continues to grow, with China alone accounting for 70% of global EV production and exports more than doubling in just the past 2 years. Meanwhile, US sales and production will likely be flat or down in 2025, even as global demand for EVs continues to skyrocket, now at 25% of global auto sales.

The money coming into GenAI will mirror the money that went into the dot com economy in the late 90’s

Easy win here. Though “absolutely dwarf”, rather than “mirror”, might have been a better description of 2025’s AI spend (more on that in our predictions below).

Listenership/viewership is going to shift to podcasts and influencer media at an even faster pace

Another easy win here. Honestly, we could probably just run this one back every year for the next several (at least) and be correct. The weekly reach of podcasts among 18 - 34 year-olds now exceeds that of television. Just let that sink in for a minute.

4. Expect a major reduction in the workforce of engineers (driven by AI coding assistant efficiencies)

Our first (big) miss here and frankly, we should have known better. While nearly every corporate R&D department is now employing AI coding assistant software and these are indeed providing big efficiency boosts (3 - 5x seems to be the consensus among our companies), companies aren’t employing fewer engineers, they’re producing more software.

Expect this to continue moving forward as both enterprise demand and platform sophistication continues to grow.

The success of AI in 2025 and beyond hinges on balancing innovation with responsibility

Another miss here, at least in terms of 2025. We still believe this to be true, but if history is any guide, guard rails won’t be seriously considered until we’ve had a whole bunch of horrific car crashes. In other words, don’t hold your breath (but definitely keep your head on a swivel).

For the first time, Nvidia will see a material decline in market share for AI chips (due to 3rd party competition and in-house manufacturing).

Given Nvidia’s 90% GPU market share in 2024, this seemed like a layup. After all, how much higher could they realistically go? Apparently to 92%. Consider our hats tipped.

The hype around Google’s new quantum computing chip has its 15 minutes, then disappears from public discourse

Given the 21st century attention-span, this was almost too easy. 15 minutes might even have been generous, as the internet almost immediately gave a collective shrug and went back to meming and complaining about stuff. For it’s worth, Google, we thought it was incredibly cool (even a hair more than those 90s-rap-AI’d-into-yacht-rock videos).

The revenge of the emerging manager (in terms of VC funding share)

Correct! This feels like a minor miracle given how the last few years have gone, as well as the historic concentration of capital in a handful of BigAI companies, but sure enough, new EM funds took in 29% of 2025 VC funding (through 3 quarters) versus 21.1% last year. We’re still well behind the 2015-19 average (38%), but hey, baby steps.

Early-stage companies see raise sizes remain flat or decrease slightly (as a result of the above rotation)

Well, the logic was sound, but we were still wrong. In fact, average “Seed” round sizes increased 46%, as multi-stage funds (perhaps realizing the mathematical corner they’ve painted themselves into?) started to dip even earlier. That said, we put “Seed” in quotes because, well, you can call a round whatever you want, even if it’s north of a $25 million raise (as 28% of “Seed” rounds have been in 2025)

Bonus Prediction: The Lions and Bills will meet again in the Super Bowl

Considering both franchises are built on soul-crushing postseason losses, this was clearly just wishful thinking

Now for the main event!

2026 Predictions

AI-native software navigation takes over: By year-end, most B2B SaaS platforms will have embedded Gen AI tools as part of their dashboards, natural language prompts will quickly become the default navigation tool, and many will see them replace traditional menus and search functions entirely.
By year end, robots will be performing enough “main street” tasks that the average urban dweller will encounter at least one per week in the ordinary course of their day. Autonomous robotics development for dozens of high-leverage use cases, taking place largely behind the scenes for years now, finally hits a sophistication inflection point allowing for scaled deployments across a number of sectors and applications. People will begin seeing these products performing regular tasks in retail, restaurants, universities, hospitals, office buildings, construction sites, and elsewhere.
Big agentic “every solution for every customer” AI companies will see accelerating churn as enterprise customers grow frustrated with the amount of in-house customization required, and the time and cost of implementation and employee training.
This is not to say that AI adoption will slow, rather that enterprise customers will rotate into products that sit within a traditional SaaS framework, purpose-built for their sectors and use cases – i.e., those that come off the shelf capable of solving their companies’ most pressing problems, pre-trained on their industries’ data, with simple and intuitive UIs designed for non-technical personnel to quickly grasp and easily incorporate into their daily workflows.
Companies across the spectrum, from Fortune 500 to 5-person law firms, will begin one of the largest restructurings in corporate history, as they adapt to new AI-powered automation. As AI rapidly replaces rote functions now performed by low-skill and entry-level white collar workers (data entry, scripted/call-center customer service, generic form/document creation, etc.), corporations across all sectors and sizes will have two key problems to address on the fly: 1) How best to retask and/or retrain these workers to work with and maximize the effectiveness of new AI tools and 2) How to replace the training that entry level workers in sectors like law and finance currently get from performing these rote tasks (e.g., how do you teach first-year legal associates to draft documents when you don’t need them to draft any of your documents?).
A new breed of cybersecurity company will emerge and rapidly scale in response to a massive increase in the volume and sophistication of spam, phishing, deep-fake, and other predatory AI bots. This should hopefully be self-explanatory, but we would just add, 1) If you think the central plot point of Mountainhead was far-fetched, well, we respectfully (and fearfully) disagree, 2) Don’t think twice, think 10 times before you click on any emailed link. We’re way (way) past the days of Nigerian princes offering commissions for moving their money, 3) Royalty-free product/company name idea for you founders: “Bot or Not” (no one under 40 will get the joke but trust us, this will crush with the average middle-aged corporate decision-maker).
Social media influencers will resign in large numbers as AI-created content takes over and replaces them. AI doesn’t do true creativity (or really anything close to it), but it’s great at repackaging generic media into other generic media, and it is considerably less expensive than most of these folks.
Anthropic will not IPO in 2026. On the one hand, Anthropic appears (from a 20,000-foot level, anyway) to have a far more sound/sustainable business model than its LLM peers (high-quality enterprise revenue, real growth, and some light at the end of the burn tunnel). On the other hand, it would be crazy to think public markets will readily embrace its current $350 billion valuation (let alone one that generates a real return for those who participated in that $350B round). But even if it did, why would they subject themselves to the administrative burden and intense quarterly scrutiny of public markets when they can continue to essentially pick any raise and valuation numbers they want and watch the BigTech/BigVC crowd trip over themselves to fill the round with no questions asked?
OpenAI will raise at least one down-round and have to drastically pare down spending and product expansion plans.
A) The current $500 billion valuation is already 6x the largest ever startup exit (before baking in even a modest 3 - 5x return to VC backers). Will someone eventually top Facebook’s now 13 year-old startup IPO record? Of course. Will it be by 25x? Absolutely, unequivocally, no.
B) OpenAI’s revenue size is impressive, but the quality isn’t (60 - 70% small consumer subscriptions), the company was already forecasting 2026 - 2029 total burn of $115B before announcing an additional $1.4 trillion in hardware spending commitments, and that burn forecast is based on truly fantastical revenue projections (for context, their projected 2030 revenue is almost double the entirety of 2024 US business software spend).
To be clear, though, they still have a great product with a lot of promise, they just need to start running the company like a real business instead of a science fiction fantasy (and pick a lane or two to dominate, rather than throwing billions at every idea that pops into someone’s head), so a harsh reality check will be a good thing for the company, long-term.
We will hit new public market highs in the first half of the year. Bubbles don’t pop when everyone is talking about bubbles popping, they pop when everyone throws in the towel on predicting a top and goes into full FOMO buying mode. Plus, markets like it when interest rates are in a downward cycle and the most recent Fed “dot plot” indicates another 50 - 100 basis points of cuts in 2026.
The bubble will burst in the second half of the year and take down the economy with it. Direct AI spending alone has accounted for 70% or so of GDP growth this year, and that doesn’t account for all of the secondary spending by those reaping the benefits of this boom.
How bad a recession we end up in is anyone’s guess, though:
On the one hand, this boom is being financed mainly by cash-rich public tech companies (who can easily absorb any losses), and private equity and private debt funds. So, banks have minimal direct exposure and the average American has essentially none.
On the other hand, 50% of consumer spending (the other pillar of GDP growth) comes from the 10% of Americans who are going to take this AI crash full in the face. So… fingers crossed?

Bonus (Non-Tech) Prediction

The US will make the semifinals of the World Cup for the first time (we’re not counting the inaugural WC in 1930 when there were only 13 teams and the semis were the 2nd round).

World Cup hosts pretty much always outperform, including the 1994 US team, which was made up entirely of college players (MLS didn’t start play until 1996) who not only inconceivably made the Round of 16, but barely lost (1-0) to eventual champs, Brazil.

For you younger readers, it’s hard to explain just how shocking this was at the time. In 1994, not only did we not have a professional soccer league or any professional soccer players, you couldn’t even find soccer on TV (from anywhere). It wasn’t just a relatively unpopular sport in the US, it basically didn’t exist.

Well, now, we have a thriving domestic league, incredibly high-level play in all manner of development leagues and academies, and a national team full of regulars on top European clubs.

Is this still a reach? For sure. Completely crazy? No.

Make us pround, fellas.

Chris spent a great couple of days in Fargo, North Dakota, and yes, it was cold, but the energy more than made up for it.

Fargo has that rare mix of quaint college-town vibe and North Midwest grit.

Friendly people, quietly ambitious builders, and some of the most “dirty and dangerous” category-defining companies are headquartered right there.

Huge thanks to the Generator team, Joe Kirgues, Troy Vosseller, and Ben Stanley — for bringing together such an impressive group to showcase their recent investments.

One highlight: Pavewise, based right in North Dakota, where C2 Ventures proudly led the seed round. Exciting to see their momentum up close.

He appreciated meeting so many founders, operators, and community leaders pushing innovation in the Midwest.

View post.

Steelhead Technologies Secures $84M Growth Investment

Huge congratulations to the Steelhead Technologies team on their $84M growth investment from Mainsail Partners.

Jeff Halonen and the team have deep industry expertise, real customer impact, and technology that actually makes hard, messy work easier for the people doing it.

Metal finishing and fabrication aren’t glamorous industries, but they’re essential. And modernizing them takes a founder who understands the problem firsthand and has the conviction to build through the complexity. That’s exactly what Steelhead has done.

C2 Ventures is excited to continue to be part of their growth as early and follow-on investors.
Read more.

Top Robotics Stocks to Add to Your Portfolio for Impressive Returns

The updated September 24, 2025 article highlights a breakout period for U.S. robotics, with Q3–Q4 2025 marked by accelerating deployments across manufacturing, healthcare, defense, elder care, and collaborative robotics. Strong order growth, major AI-driven product launches, and expanded government and enterprise investment are pushing robotics toward mainstream adoption, supported by advances in physical AI, 5G, and autonomous systems. Trimble, NVIDIA, and Teradyne are positioned as key beneficiaries—Trimble through AI-powered construction automation, NVIDIA as the core infrastructure layer for physical AI and robotics, and Teradyne via collaborative and mobile robots—collectively illustrating why robotics is emerging as a multi-decade, cross-industry growth theme heading into 2026.

Pioneers and Pathfinders

Ross Guberman, founder and CEO of BriefCatch, a leading legal writing assistant that helps lawyers communicate with clarity and precision, joined the Pioneers and Pathfinder podcast. A former BigLaw attorney and award-winning journalist, Ross draws on decades of experience teaching opinion and advocacy writing to top law firms, judges, agencies, and corporations around the world.

In the conversation, Ross shares his path into law, the analytical framework he developed for evaluating great legal writing, and key lessons from building BriefCatch into a category-defining product. The episode also explores how technology—and generative AI in particular—is reshaping legal writing, and what these changes could mean for the future of the legal profession.

Impilo Expands Digital Health Offerings Through Partnership with Eko Health, Featuring the Eko CORE 500™ Digital Stethoscope

Impilo announced a strategic partnership between its e-commerce platform, The Digital Health Store, and Eko Health to make the Eko CORE 500™ Digital Stethoscope available directly within Impilo’s ecosystem. The collaboration expands access to AI-powered cardiac and pulmonary diagnostics for clinicians, supporting both in-person and virtual care. By integrating Eko’s advanced diagnostic technology into its hybrid healthcare platform, Impilo continues its mission to bridge innovative digital health tools with practical, scalable clinical care.

BlueTechX Accelerator

Huge congrats to the eSkuad team on pitching in person for the first time at BlueTechX in Tampa.

After nearly three months in the BlueTechX Accelerator—run by Tampa Bay Wave and The Continuum with support from NOAA—the team wrapped up an incredible stretch of learning, connection, and growth.

Love seeing founders build in community, turn classmates into partners, and sharpen their story in front of a live audience.

AI Bottleneck: Electricians, not Inference, Chips or Power

Most people talk about chips and GPUs. Ian Hoppe argues the real AI bottleneck hides in 5.9 million undocumented commercial buildings and the trillions of wires behind their walls.

Ian is a master electrician and the founder & CEO of Condoit. He explains how undocumented systems inside hospitals, data centers, and factories raise the risk of fires, outages, and lost lives. He shares why a single data center outage often burns around $500,000 dollars per hour and why, without Condoit, no one knows what feeds the chiller keeping the racks cool until crews go and trace wires by hand.

Retrievables is Helping Businesses get Paid, Without the Drama

Jeremy Crane, founder and CEO of Retrievables, is modernizing an industry few people dream of entering: debt collection. What started as domain expertise gained at a New York collections law firm turned into a venture-backed platform that helps businesses recover delinquent payments without outdated tactics. Retrievables operates as a tech-enabled marketplace, instantly matching companies with the right collection agencies or law firms, helping businesses get paid faster while creating new demand for service providers.

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C2V November Notes From The Trenches

C2 Ventures

Nov 25, 2025

Welcome Friends! Well, it’s the season of giving thanks and as you may recall, last year while trying to come up with a new way to thank the same groups of people, we decided to pivot to deal flow awards (though we do still love you just as much, LPs and port co founders).

As a reminder, this came about from all of the times people asked us how we manage to get through so many deal submissions each week without losing our minds. Okay, we’re pretty sure we’ve never been asked this, but if you did ask... the answer would be to find the fun/funny wherever it may be hiding (trust us, there’s a lot of it, usually in plain sight).

This levity-in-the-monotony is something we are truly thankful for and since we’re already jamming a nearly-no-holds-barred word salad on the world every month, we figured why keep all of the fun to ourselves.

(Quick aside: should we translate “levity-in-the-monotony” into Latin and use it as the motto for this awards column in the future? Ala, “e pluribus unum” or “deus ex machina”?)

So, without further ado, we give you our second annual edition of…

The Spammys

(One more quick aside: we really need intro music for this in case anyone wants slap something together. Preferably in the spirit of an ‘80s movie or SNL sketch theme song — think St. Elmo’s Fire, Tiny Elvis, anything by Kenny Loggins, etc.).

Okay, here we go…

Best Cold Email Subject Line

“Matt - are you DTF? (Down to Fund)”
- We’re just amazed this had been sitting there this whole time and no one had jumped on it until a few months ago.
- If there’s one nit to pick it’s that this would have been even funnier if they had waited to explain the acronym until the end of the email, but still a worthy winner.

Best Company Tagline

Runner-Up:
- “Bumble for jobs”
  - Not necessarily a comp we’d choose for this (or just about any) product, but at least it’s no worse than PG-13…
Winner:
- “OnlyFans for zoos”
  - We… um… you know what, let’s just get out of here before we say something we can’t un-say

Real Startup Name That Most Resembles a Fictional Startup Name You’d Come Up w/For a Movie or TV Show Award

Vandrax Technologies

Best Impersonation of a Russian/Chinese/North Korean Malware Bot Award

Are we allowed to give this to an actual Chinese malware bot? If so, DeepSeek ran away with it. If you thought it was a bad idea to put TikTok on your phone...
- Related note, we’re not sure you should be any more comfortable handing your phone’s contents over to Larry Ellison
- And before you say, “Yeah, but at least you won’t be helping a self-interested, possibly nefarious actor use disinformation to manipulate public opinion, elections, etc. for self-serving purposes”… well, are you sure that’s not what you’ll be doing? Maybe you could find someone willing to let you watch them dance or pack boxes in real life instead? Just spitballing here.

Best Indavertent Reminder of a Legendary 90’s Commercial Award

To autonomous helicopter company, HELI-D (and maybe the beginning of the end for Purple Stuff Aviation)

Dirtiest, Dullest, and/or Most Dangerous Conference Award

We asked our founders for their most mundane industry conferences and the response was truly incredible. So much so that events like the annual meetings of the Association of Payment Professionals - Risk and Underwriting and the American Public Works Association, Texas Chapter couldn’t make the cut.

In other words, nothing but winners here… but in the spirit of earning our newsletter subscription fees (of $0), we’ll do our best to narrow it down:

Honorable mentions (in no particular order):
- Association for the Advancement of Medical Instrumentation Summit
- Louisiana Parish Engineers And Supervisors Association Fall Conference
- Society of Industrial and Office Realtors Spring Conference
- World of Asphalt
Runner-up:
- RoofCon
And your winner is…
- Compost 2025
Congrats to WATS for that winning submission (and Alivo who probably takes this in any other year)

Best Shamelessly Self-Promoting Award Award⬆️

Nailed it

Most Words Used to Provide the Least Amount of Information Award

“Empowering Built Infrastructure to Thrive: Robust Solutions for a Lasting Future.”

Closest We’ve Come to Regretting Our Investment Thesis Award

Product description: “Adult Diaper Smart Wearables”
- Yes, this is real
- Yes, it is exactly what it sounds like
- Yes, we absolutely walked ourselves right into this
- No, we still have no regrets. Live by the sword, die by the sword.
- (In fairness, this did seem to be a legit product and was quite well presented… but still…)

Best Founder Response to a Pass Award

“Ok! But keep an eye out for us bc we are going places!”
- It is not easy to say “you worthless fools will regret this” (which we do occassionally get) while sounding respectful, positive and upbeat (which is mostly what we get), but they nailed it. Well done.

Folks, Some Human Effort is Still Required Here Award

“We see you invest in , and we thought you’d be a great fit” [yes, it really had a blank there]
- The ubiquitous use of AI-generated emails for funding outreach is probably inevitable, but you could at least make the effort to fill out the Bot Mad Lib.

Worst AI Bot Name

Tie between “Pete,” and “Cindy”
- Founders, we need to talk about this (again). You cannot give your AI bot a common human name. As we noted last year, think about naming your bot like you’d think about naming your dog. Have you ever met a dog named “Mike”? Exactly.

Best AI Bot Name Award

Runner Up
- Sparky (from our friends at Beagle Labs)
  - We feel seen
Winner:
- Takeoff Monkey
  - They get it.

One-Percentiest Product Award

(Always our favorite category)

Runner Up
- [Name redacted] - An app for livestreaming animal enclosures at zoos (and our first ever two-category nominee!)
  - Problem: “Zoos See 10x More Attendance than the NFL. So Why Are NFL Revenues 10x More than Zoos?”
    - This was clearly written by someone who hasn’t been awakened at 6am on a Saturday by two kids jumping on them, or they’d know that 9.99x of that attendance delta was just parents’ default answer for “How the hell am I going to entertain these two for the next 12 hours?”
Winner
- [Name redacted, but as icing on the cake, it’s ripped off from a song so well known it’s been played at a Super Bowl halftime show] - “The nightlife platform Gen Z actually wants”
  - “The problem? Young people often decide to go out spontaneously, but waste time figuring out where to go. We’re solving this with live activity maps, local group chats, and tools to discover, create, or join parties anywhere, all in one place.”
    - No seriously, this is really cutting into Gen Z’s training of Larry Ellison’s future mass-mind-control bots.

Jokes aside, if you’re serious about starting a tech company and it even once occurred to you to build a startup focused on something your immediate circle of friends does in their leisure time, we would strongly encourage you to push pause, close your eyes and point to a spot on a map of the US, pack a backpack (and only a backpack), take a bus there (not a train or a car, and definitely not a plane; a bus), check yourself into a motel (with an “m” not an “h”), and stay there until you realize you were born halfway between third base and home (with no outs and a .380 hitter at the plate ) and you need to look outside your personal bubble for problems to solve because you and your friends have never had a real problem in all of your lives combined.

While you’re at it, consider spending some meaningful time outside of SF lest you wake up one day and find you’re on a podcast, introducing yourself and your abhorrent friends as “the besties”.

Not Quite Sure How to Feel About This Award

To this email…

On the one hand — Do we have a stalker to worry about here?
On the other hand — We have a stalker! Does just any run-of-the-mill VC warrant stalking? Didn’t think so.

What a moment.

That will do it for the 2025 Spammys!

Many thanks to all who participated (intentionally or otherwise). You truly delighted us once again. Please keep them coming so we can do this again next year.

Levitas in taedio. (It works, right?)

Robotics is Entering its Breakout Moment

The latest Q3 data makes one thing clear: Robotics is accelerating as manufacturing deployments hit record highs, healthcare robotics crossed major commercial milestones, and AI-powered automation is moving from pilot to production across every “unsexy” sector of the economy.

This is exactly the moment we’ve been building toward at C2 Ventures.

Our thesis has always been simple: The biggest opportunities live in the Dirty, Dull, and Dangerous, and robotics with AI integrated are finally transforming those industries at scale.

As physical AI matures, labor pressure rises, sensors become cheaper, and robotics infrastructure becomes plug-and-play, the adoption curve has officially shifted.

2026 is shaping up to be a breakout year for automation.

And the next generation of category-defining robotics companies is being built now, and we’re backing the founders on the front lines of that shift.

See post.

What Keeps Coming Up in Every Conversation

Chris has been talking to a lot of founders and VCs this month, and one thing keeps creeping into every conversation:

Everyone wants returns on a year 5 timeline… but all the real outcomes still happen in year 10–12.

It doesn’t matter how markets cycle or how much AI hype gets pumped in. Building a billion-dollar company still takes a decade. Minimum.

Yes, there will be earlier wins: the singles, doubles, and steady capital-returning moments. But the unicorns? The generational outcomes? They require patience, endurance, and teams that simply refuse to die.

If a company is still standing in year 8 or 9, that’s usually a green flag.
Struggling companies don’t survive that long.

And that’s been the throughline in every conversation lately:
conviction + time > everything else.

Especially now, as early-stage B2B, robotics, and automation collide with AI. Legacy industries are being rebuilt from the inside out. Construction, manufacturing, logistics, energy, and field services are all going through their biggest shift since the internet.

This moment massively favors early-stage investors who are willing to underwrite the long game, not chase the hot hand.

AI is finally hitting the dirty, dull, and dangerous parts of the economy where it actually moves the needle.

The upside starts now.
The outcomes, as always, will take time.

Boostr Celebrates 10 Years of Innovation

Boostr is marking a major milestone this month: a full decade of building tools that move the media industry forward. To commemorate the moment, CEO Patrick O’Leary shared a special anniversary message recorded in the Redwoods — the same place where the name Boostr was first envisioned.

From the beginning, Boostr has been guided by a simple mission:
build great products that solve important problems and deliver exceptional service.

That commitment has carried the company from its roots as a specialized CRM to today’s unified Ad Management Platform used by leading media organizations.

As Boostr celebrates ten years, the team is also looking ahead to its next breakthrough:

The Boostr AI Agent Series

This new innovation represents a major step forward in applying AI to real operational challenges, automating repetitive tasks, improving accuracy, and unlocking operational excellence across the ad lifecycle.

Boostr credits its clients as the driving force behind this progress, shaping the platform through their partnership, feedback, and ambition.

Here’s to the next decade, the best is yet to come.

Watch Patrick’s full message and learn more about Boostr’s AI-powered future

Airports Going Green®

We are proud to share an update from portfolio company WATS, which is partnering with LaGuardia Gateway Partners and the Memphis–Shelby County Airport Authority as they advance new initiatives in sustainable materials management.

WATS continues to demonstrate how data intelligence can transform airport operations. Their platform provides the standardized, actionable waste and materials data that leaders need to build effective, measurable, and truly sustainable programs.

As WATS connects with more airports across the country, the mission remains clear:
Better data leads to greener, more efficient airports.

C2V is excited to support their momentum and the growing demand for smarter sustainability infrastructure in aviation.

Civ Robotics Founder on Winning Over Tech Skeptics

Civ Robotics co-founder and CEO Tom Yeshurun published a new SmartBrief article on one of the construction industry’s biggest challenges: bringing innovation to teams that are wary of new technology.

Drawing from his field experience, Tom outlines why skepticism is so common in traditional industries — from deep trust in long-standing methods to budget concerns and past negative tech experiences. He shares practical strategies for introducing automation and AI that reduce risk, fit existing workflows, and lower the effort required to try something new.

Tom also emphasizes the importance of securing buy-in from the right decision-makers and staying patient — because in construction, a “no” today often becomes a “yes” once teams see the real-world value.

It’s a thoughtful look at how to drive adoption in sectors where innovation is needed most.

Gripp Featured on The Germinate Podcast

Tracey Wiedmeyer, co-founder of Gripp, was featured on The Germinate Podcast to discuss how the platform is transforming maintenance tracking across agriculture and beyond.

Introduced through connections at FEMA, Tracey shared Gripp’s origin story inside Purdue University’s venture studio, Dial Labs, where the team set out to solve one of ag’s most persistent operational challenges: fragmented, paper-based equipment record-keeping.

On the podcast, Tracey walks through how Gripp’s “dead-simple” QR code tagging system enables farmers to log maintenance, access manuals, capture videos, and preserve tribal knowledge — all with a single scan. With no training required and universal accessibility, Gripp has quickly stood out in a space crowded by hardware-heavy solutions, including at the American Farm Bureau Federation’s Ag Innovation Challenge.

While Gripp was built for agriculture, its design philosophy — simplicity, empathy, and scalability — is driving adoption across construction, manufacturing, and other maintenance-intensive industries.

Watch the episode.

Why 2025 Is a Breakthrough Year for Zero-Waste

2025 has become a reality check for zero-waste goals. Many companies across consumer goods, industry, and commercial real estate are discovering they’re far off track — not because of a lack of intention, but because waste data remains fragmented, inconsistent, and difficult to measure.

As regulatory pressure rises, tenant expectations increase, and disposal costs climb, organizations are being forced to confront the limits of their current systems.

This year marks a turning point: a shift from broad aspirations to clearer measurement, better data practices, and more realistic strategies for reaching long-term waste and circularity goals.

Launch of GRIPP TECHNOLOGY Is Announced on al Walkabout® MOTHER BIN Models

Gripp Launches on All Walkabout® Mother Bin Models

Walkabout® Mother Bins has announced that all of its grain storage models will now come equipped with Gripp, the asset-tracking and maintenance app developed by C2V portfolio company Gripp. Through QR codes on each bin, operators can instantly access service videos, manuals, parts ordering, and a shared maintenance history — making it easier for teams to manage equipment in the field.

Walkabout CEO Dave Hedt described the integration as a major step in improving customer support and real-time access to equipment information. Gripp co-founder Tracey Wiedmeyer noted that the partnership reflects Gripp’s mission to deliver simple, practical tools built for operators, not office workflows.

The rollout gives Walkabout customers a more efficient, connected, and transparent way to manage the equipment that keeps their harvest operations moving.

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C2V October Notes From The Trenches

C2 Ventures

Oct 31, 2025

Welcome friends! Well, if you haven’t had enough of us shouting into the void about the reckless destruction of capital going on in the plus-sized end of the venture world these days, we decided to run it back one more time, only with more math. You’re welcome.

Seriously, though, this will be it for at least the next two months as we roll out our annual deal-flow awards in November and 2026 predictions in December, so bear with us while we wrap this up.

In researching last month’s newsletter, we came across a fairly shocking number of quotes from prominent, late-stage mega fund managers that are all some version of this (from a well known market participant)…

Valuation matters far, far less than the decision of whether to invest or not.

… and we couldn’t let it pass without some serious pushback.

Valuations Don’t Matter (?!)

Of course, we all strive to invest in the best companies with the biggest outcomes, but this way of thinking about that goal relative to when and at what price we invest in these companies is not just wrong, it’s the exact inverse of the way this actually works. In fact, when it comes to generating investment returns, if you get the valuation wrong, nothing else matters.

For example, let’s say you invested $20 million in each of two companies, Company A has an exit at a $100 million valuation, and Company B at $10 billion. The better company is obviously Company B (by a wide margin), but which was the better investment?

Well, if this most fundamental of questions is unanswerable without knowing your entry valuation (as it clearly is), how can entry valuation be irrelevant? Right, it can’t. In fact, even if you knew with absolute certainty that a specific company was going to be the largest exit of a given year, there’s still a valuation level at which passing on it will actually be accretive to your overall returns.

We’re not entirely sure where or when this idea that valuations are irrelevant became a regular talking point (or how it’s still being espoused by the same managers who are sitting on dozens of valuations for 2021’s “must own” companies that remain 50% or more underwater), but it almost seems like the average mega-fund manager believes there are two sets of potential venture outcomes, one for the Seed/A/B/C investors and a second one for them (which is several times larger).

That, or they actually believe they’ll be able to identify the absurdly large percentage of every 3 – 4 year cycle’s largest exits that it would take just to generate slightly above average returns. Along those lines, we encourage you all to check out Josh Kopelman’s new Venture Arrogance Score, which does a nice job of quantifying this fantasy (seriously, bravo, Josh; we couldn’t be more jealous that we didn’t come up with this first).

Obviously, the mega fund strategy is the extreme for all of this (which we’ll get to below), but valuations absolutely matter for all stages and strategies, and that also seems to be getting lost, even at the very early stage, as median Seed round valuations (and Seed funds themselves) grow ever larger. So, we’ll start with a quick breakdown of two fairly common versions of today’s Seed strategy that we’re seeing to try and illustrate just how much of a drag on returns (and increase in risk) you incur by being too loose with valuations.

Seed Fund Math

Two examples to illustrate this. For both funds, we’ll assume:

75% of committed capital is “investible” (the rest going to management fees and operational expenses)
60% percent is allocated to initial investments in 25 companies
The balance is allocated to follow-on rounds in the best 13 of these companies
Industry average dilution at each round (~20% at Seed and Series A, 10 – 17% for subsequent rounds)
A minimum of one-fifth of each round is set aside for existing and other new investors (so neither fund can take more than 80% of any round).
We’ll use a simplified version of Fred Wilson’s “1/3 Rule” (which essentially puts numbers to the VC power law), where 1/3 of the companies drive most of the fund’s returns (in this case, we’ll assume the other 2/3s return half the fund).
The last funding round before exit for each of the return-driving third is Series D

Fund 1

$225 million in total commitments
$4 million per company at Seed
$5.4 million of follow-on capital per company (deployed at Series A & B)
3.0x net return target (top quartile or better in nearly all vintages)
Average Seed round post-money valuation: $20 million (this is the minimum needed to make that initial check size work, and if you’re thinking this is a strange way to come up with a valuation, you’d be right… But this is exactly how we see it done in nearly every round led by these plus-sized Seed funds).

The results:

Average ownership at exit: 14.4%
Exit needed for any one company to return the entire fund by itself: $1.6 billion
Average exit needed from each of the 9 return- driving companies (we rounded up) to hit the target return: $520 million

Fund 2

$100 million in total commitments
$1.8 million per company at Seed
$2.4 million of follow-on capital per company (deployed at Series A & B)
3.0x net return target
Average Seed round post-money valuation: $12.5 million (roughly our average entry valuation in our first two funds; our funds are smaller, but the math at $100 million in commitments still works fine at this valuation level)

The results:

Average ownership at exit: 9.8%
Exit needed for any one company to return the entire fund by itself: $965 million
Average exit needed from each of the 9 return-driving companies to hit the target return: $322 million

Takeaways

While the ask of the larger seed fund in this example certainly isn’t crazy (not mega-fund-crazy, anyway), the difference between the two is substantial, with the more price-concsious fund having both materially lower risk of underperforming and materially higher upside. For example:

In the past four years, there were nearly twice as many exits of at least the size needed for the value-conscious manager to return their entire fund (actually 1.5x, including the 16 also-ran companies) with a single exit.
The average exit among the 9 return-driving companies needed by the more value-agnostic manager to be a top performer is 2.1x the median exit value in 2025 (per Pitchbook), whereas the average required by the more value-conscious manager is only 32% above that median.
If both managers were to hit on a top 100 exit within a fund cycle like the past four years (~$5 billion at the low end), that exit alone would result in a net return to investors of 4.3x their investment for the value-conscious manager and 2.8x for the price-agnostic manager. While we’d imagine investors in either fund would be pretty happy with such an outcome, it’s still a material delta — roughly the difference between doubling the S&P’s annual return and tripling it over the same 10-year period.

Really, the only rationale for raising funds that are too big, forcing you to overpay (other than the cynical but definitely still true reason that management fees on $225 million are 2.25x larger than those on $100 million), would be if there were some correlation between early-round valuations and outcomes. But both a handful of industry studies and our own experience show that there is no correlation whatsoever.

So, if even a relatively small difference in valuations has an outsized impact on return variance and upside potential, what does it look like at the extremes? Well, there’s leaving some risk mitigation and upside potential on the table, and then there’s “how did this strategy ever make it off the white board”?

Late-Stage Mega-Fund Math

General Assumptions:

75% of committed capital is investible (same as with the Seed funds)
40% percent allocated to initial investments (lower than the Seed funds due to the acceleration of round size growth as you go further into the alphabet)
15 total companies (these funds are more concentrated due to 1) the limited pool of opportunities at these stages, 2) the size of each funding round, and 3) because companies at this stage are, ostensibly, much surer bets)
Follow-on capital allocated to all 15 companies (as, again, these are “sure things”, and since it’s just the company that matters, not the price, you couldn’t possibly throw enough money at them, right?)
We use industry medians, per Pitchbook, for valuation and funding at each round
A minimum of one-fifth of each round is set aside for existing and other new investors (same as with the earlier rounds).
While managers of these funds liberally throw around the power law in discussing their strategies, since the power law doesn’t really apply when the single largest exit ever wouldn’t even get you to an average return, we’ll let them slide on the fact that the power law would also mean a substantial portion of each portfolio should return 0-1x, and assume all 15 companies will positively contribute to returns.
Investments start at Series D, and the last round for every company prior to exit is Series G

Fund Math

$2.5 billion in total commitments
$53 million per company at Series D
$80 million of follow-on capital per company (deployed at Series E - G)
3.0x net return target

Results:

Average ownership at exit: 8.5%
Dollar-weighted average entry point: $2.1 billion
Exit needed for any one company to return the entire fund by itself: $29.3 billion
Average exit needed from each of the 15 portfolio companies to hit the target return: $6.9 billion
Total exit value needed: $102.7 billion

To put these numbers in perspective, over the past 4 years (the wide end of the general exit window for funds at this stage), there have only been 35 exits at least as large as this fund’s average entry point, and only 8 at least as large as its target average, and that’s across all categories. Assuming most (if not all) of these funds have at least some sector/product focus, that pool shrinks even further.

We’re also being extremely generous in our valuation and raise assumptions by using median numbers. If we use averages instead (likely a lot closer to many of these funds’ actual numbers), there are only 8 exits larger than the average price paid for each company ($8.3 billion).

But that’s not even the craziest part.

Using the more generous median funding round numbers, in order to hit the 3.0x net return target, the fund would have to be in at least one of the three largest exits of the past four years, plus (at a minimum) each of the 5^th through 18^th largest exits, and even if it managed a clean sweep of the top 15, its largest possible net return would still only be 4.6x.

Still not the craziest part.

Using the average funding round numbers, a 3x net return is not even possible. Even if this fund achieved the stated goal of just making sure they were in every one of the 15 largest exits, their net return would be 2.0x.

Now, one might argue that these results assume uniform capital allocations and valuations across all companies, and any manager clairvoyant enough to predict every one of the top exits over a 4-year period could surely dollar-weight them correctly as well. Of course, anything’s possible (though if you knew which company would have the biggest exit in a given period, why wouldn’t you just put the whole fund in that one name?), but what if the opposite happens? What if you do manage to get into one of these top 3 exits, but you bought into it at a much (much) higher than average valuation…

Figma IPO

As much as (we hope) the outline we modelled above makes our point, it still assumes a level of price discipline (in sticking with uniform, industry average price points) that is almost certainly still too generous, so just to really hammer how badly this strategy of being in the best names at any price actually plays out when put into practice, let’s look at the real world example of Figma.

As we mentioned in our September newsletter, 8 of the 10 $1 billion-plus IPOs thus far in 2025 debuted at a price lower than at least one (and as many as three) of the companies’ private funding rounds, producing losses for VCs who invested in these rounds. One of the two that produced positive returns for everyone was Figma, the third-largest exit of the past four years, and pretty much the literal embodiment of the company you have to be in, regardless of price, if you subscribe to this idea.

Well, let’s see what happens if we run the exact same model we outlined above for a late-stage investor in Figma. If we make it a $1.5 billion fund, the math actually works out more or less perfectly for a firm that first invested as the Series D lead and then followed on in the next and last (Series E) round (there might even be a firm that did exactly that…).

In the best-case version of this not-necessarily-hypothetical example, the fund would receive $400.3 million in proceeds from the IPO. But that’s really where the good news ends. In the best-case scenario, that fund might have been able to take $40 million of Figma’s $50 million Series D round and, based on the earlier allocation assumptions, add another $60 million in the Series E.

The result? A 3.8x gross multiple on this investment and a net return to LPs of 22% of total commitments (and while they could have theoretically invested more at Series E, that would actually make the return multiple worse, as the Series E ROI was only 1.5x).

We’ll spare you the math as far as what this means for overall portfolio returns, but suffice it to say that if the third-largest IPO in a 4-year exit window only returns a fifth of your fund, it’s pretty much game over. Forget 3x returns, your LPs will be lucky to even get all of their original investment back.

Honestly, how does a manager (or even an entire strategy) realistically come back from something like that?

Apparently, by quintupling down on the strategy with a $20 billion fund.

We give up.

On to our newest investment (made at a valuation where, if they end up being the next Figma, we and all of our investors will be retiring about 30 seconds after the bell rings on the NYSE)…

One day, we’re going to run out of companies that are even dirtier, duller, and more dangerous than the ones already in our portfolios. But today is not that day, as we welcome Pavewise, a SaaS operations management and automation platform for paving contractors.

Spawned from the pain points and inefficiencies founder Bryce Wuori experienced firsthand in his years managing paving projects, Pavewise’s platform compiles data from disparate sources, generating operational insights and automating regulatory and project sponsor reporting.

As with all of our DDD software companies, Pavewise creates material ROI through direct reductions in day-to-day administrative bottlenecks and actionable operational efficiency insights. But the company also collects project specification measurement and testing data, as well as real-time, hyperlocal weather data, and automatically generates contractors’ mandatory regulatory and project sponsor reporting, saving contractors millions of dollars a year in costs related to reporting delays, reworks, weather-related downtime, and other common compliance issues.

We’re excited to help Pavewise continue to take market share in the paving sector, as well as adjacent infrastructure construction and maintenance verticals in the future.

On The Road Again

Three events. Three regions. One clear theme is that innovation isn’t coastal anymore.

Over the past few weeks, Chris hit the road from Milwaukee to Cape Cod to Greenwich, speaking and connecting at Venture North, The Chatham Conference, and the Greenwich Economic Forum.

Each event brought together founders, investors, and ecosystem builders redefining where and how innovation happens.

At Venture North, 300+ founders and investors packed the room, proving that the Midwest isn’t just catching up, it’s defining what’s next in clean energy, defense tech, and industrial innovation.

At The Chatham Conference, Chris joined a panel on the “Proximity Effect” to debate whether geography still matters in venture. His take: sometimes yes, sometimes no. Execution and market fit outweigh ZIP codes, and lazy pattern-matching misses great companies, especially in the places others overlook.

And at Greenwich, the conversations reinforced how interconnected these ecosystems have become. Capital and talent are flowing in new directions, and the smartest investors are following the signal, not the stereotype.

What’s clear and drives our investing every day: Great companies can come from anywhere. The investors who truly believe that are the ones shaping the next decade.

Cylerity Raises $4M Seed Round and Secures Up to $24M Debt Facility to Fix Healthcare’s Slow Pay Problem

Healthcare’s Slow-Pay Problem has Been Broken for a Long Time
Most providers wait months to get paid for care they’ve already delivered.

Ryan Wheeler and the team at Cylerity decided that was unacceptable—and built a platform that uses AI to turn reimbursable medical claims into financeable assets, giving providers access to capital in hours, not months.

C2 Ventures is proud to co-lead Cylerity’s $4M equity round and $24M in debt capacity alongside HealthX Ventures and Upstream VC to help accelerate their mission of modernizing healthcare finance.

The opportunity here is massive: bringing real-time data, automation, and liquidity to one of the most complex financial systems in the world.

Excited to back Ryan and the Cylerity team as they scale a smarter, faster, and fairer system for healthcare providers everywhere.

Civ Robotics Hits the Road This November

Civ Robotics is hitting the road this November, showcasing its latest autonomous layout tech at two major industry events.

First stop: Dirt World Summit (Nov 5–7 | Grapevine, TX | Booth #220) — where the team will demo CivDot+, delivering laser-accurate layouts within 3/100’ (8 mm) precision, and CivDot Mini, capable of marking up to 18 miles per day with sub-inch (25 mm) accuracy.

Then it’s on to Trimble Dimensions+ (Nov 10–12 | Las Vegas, NV | Booth #403), hosted by Civ’s investor, Trimble, to highlight how autonomous layout is transforming field operations and logistics.

Trusted by Bechtel, Boldt, and Primoris, Civ Robotics continues to help contractors accelerate infrastructure projects, reduce costs, and improve safety — proving robots really can play in the dirt.

They’re also hiring. If building the future of construction through robotics sounds like your kind of project, explore open roles across engineering, operations, and more: civrobotics.com/careers.

Armilla AI Expands AI Risk Intelligence Toolkit at ITC Vegas 2025

Armilla AI—the first MGA focused exclusively on AI insurance—launched its “Navigating AI Litigation and Risk” white paper and a new AI Litigation Database at ITC Vegas. The resource combines real-world litigation data with model-level testing, giving insurers and brokers both a rearview and forward-looking view of AI risk.

Analyzing 200+ AI-related cases, Armilla found that litigation around AI is becoming systemic, particularly in sectors like healthcare, finance, and employment. Beyond privacy and copyright, new exposures are emerging from model performance failures and hallucinations.

The database powers Armilla’s underwriting with live intelligence, helping quantify and price AI risk more accurately. Through its new Partner Portal, brokers can access searchable case data, emerging litigation trends, and educational tools to guide clients through the evolving landscape of AI liability.

SendTurtle at DC Startup & Tech Week

SendTurtle is kicked off DC Startup & Tech Week (formerly DC Startup Week), connecting with founders and early teams across the DMV. The team’s AI-powered platform helps startups sign, send, and summarize documents—turning eSign workflows into real-time insights. If you’re in town, catch them at events all week.

Follow the conversation →

person holding pencil near laptop computer

Retrievables Adds Mercury to Its Partner Network

Retrievables announced a new partnership with Mercury, expanding its Partner Network to include the modern banking platform used by startups and growth-stage businesses. Retrievables clients will now gain access to exclusive offers and financial services from Mercury, complementing Retrievables’ network of lenders, attorneys, and collection agencies.

The collaboration builds on more than a year of partnership through Mercury’s perks program and creates smarter ways for businesses to manage capital and recover unpaid invoice funds.

Learn more →

Noteworthy AI at Grid Forward Conference

Noteworthy AI joined leaders from Buzz Solutions, Overstory, and Pano AI at the Grid Forward Conference to discuss how artificial intelligence is transforming grid reliability and resilience. CEO Chris Ricciuti spoke on the panel “Unlocking Insights of Visual Information from AI,” highlighting Noteworthy’s work in turning visual data into actionable intelligence for utilities. The team also connected with industry peers, driving innovation across the energy sector.

See more →

The Moment When Frustration Meets Innovation

For Bryce Wuori, that moment came after a decade managing paving projects across the country—watching time, money, and quality get lost to weather delays, mismanagement, and missing data.

Instead of accepting it, he built a solution.

Pavewise turns the chaos of road construction into actionable insight—helping contractors make smarter decisions, stay compliant, and keep projects on schedule. Since launching in 2024, they’ve rolled out advanced weather tools, Density+ for quality tracking, and now work with 27 contractors nationwide.

C2 Ventures led Pavewise’s $2.5M seed round, fueling their expansion beyond asphalt into heavy civil construction—and helping make smarter, safer, more connected jobsites the new industry standard.

Proud to back Bryce and the team as they modernize one of the world’s oldest industries, one mile at a time.

Read the article.

Cylerity is Hiring: Early-Career Data Engineer (Madison, WI)

Cylerity—a fintech accelerating healthcare providers’ access to working capital by turning reimbursable claims into financeable assets—is hiring an early-career Data Engineer. You’ll build and maintain data pipelines, own data quality, and partner with engineering and ML teams to deliver trustworthy, usable data that powers the platform.

Core skills: Strong SQL; scripting in Python/TypeScript; data viz (Matplotlib, d3.js); clear communication and independent problem-solving.
Nice to have: Azure (Data Platform/Data Factory), ELK, FastAPI/Express, and familiarity with financial/healthcare data.
Details: Full-time • Madison, WI • Reports to Lead Engineer/CPO • Open until November 20, 2025.

Apply: cylerity.com/careers/data-engineer

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In the Trenches by C2 Ventures

C2V February Notes From The Trenches

A Demise Greatly Exaggerated

Exceptional Demand Indications

Continued Supply Constraints

Beginnings of a Spring (Portfolio) Cleaning?

Deal Activity

Valuation Reflation

VC Fundraising Reset (Sort Of)

Avol raises $3.8M to deliver organs and blood to hospitals

Operatory Subscription Model for Dental Practices

Getting a GRIPP on the Operation

How Two Years of Engineering Work Almost Killed Civ Robotics

BriefCatch Just Announced They’ve Acquired WordRake.

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C2V January Notes From The Trenches

Tesla’s Sales Stagnation, the “Elon Premium”, and Leaning Into Strengths

Is Waymo Actually Underrated?

Is Uber in the Early Stages of a Future Business School Case Study on Adapting to Competition

Is Apple Really Striking Out on AI or Are They Potentially the Smartest People in the Room?

Acquisitions Are Back, But Exit Math Still Matters

Impilo Doubles Operational Capacity with New Warehouses in Philadelphia and Phoenix

WATS Sweepstakes Offers 12 Months of Free TRUE Waste Data Processing for One Facility

Gripp Rendezvoo Wins 2026 AE50 for Its New “Equipment Relationship Management” Platform

BriefCatch Raises $6M Series A to Expand AI Products and Pursue Disciplined M&A

Boostr + Passendo Partner to Centralize Newsletter and Email Ad Operations for Publishers

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C2V December Notes From The Trenches

2025 Prognostications Review

2026 Predictions

Steelhead Technologies Secures $84M Growth Investment

Top Robotics Stocks to Add to Your Portfolio for Impressive Returns

Pioneers and Pathfinders

Impilo Expands Digital Health Offerings Through Partnership with Eko Health, Featuring the Eko CORE 500™ Digital Stethoscope

BlueTechX Accelerator

AI Bottleneck: Electricians, not Inference, Chips or Power

Retrievables is Helping Businesses get Paid, Without the Drama

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C2V November Notes From The Trenches

The Spammys

Best Cold Email Subject Line

Best Company Tagline

Real Startup Name That Most Resembles a Fictional Startup Name You’d Come Up w/For a Movie or TV Show Award

Best Impersonation of a Russian/Chinese/North Korean Malware Bot Award

Best Indavertent Reminder of a Legendary 90’s Commercial Award

Dirtiest, Dullest, and/or Most Dangerous Conference Award

Best Shamelessly Self-Promoting Award Award⬆️

Most Words Used to Provide the Least Amount of Information Award

Closest We’ve Come to Regretting Our Investment Thesis Award

Best Founder Response to a Pass Award

Folks, Some Human Effort is Still Required Here Award

Worst AI Bot Name

Best AI Bot Name Award

One-Percentiest Product Award

Not Quite Sure How to Feel About This Award

Robotics is Entering its Breakout Moment

What Keeps Coming Up in Every Conversation

Boostr Celebrates 10 Years of Innovation

The Boostr AI Agent Series

Airports Going Green®

Civ Robotics Founder on Winning Over Tech Skeptics

Gripp Featured on The Germinate Podcast

Why 2025 Is a Breakthrough Year for Zero-Waste

Gripp Launches on All Walkabout® Mother Bin Models

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C2V October Notes From The Trenches

Valuations Don’t Matter (?!)

Seed Fund Math

Fund 1

Fund 2

Takeaways

Late-Stage Mega-Fund Math

General Assumptions:

Fund Math

Results:

Figma IPO

On The Road Again

Cylerity Raises $4M Seed Round and Secures Up to $24M Debt Facility to Fix Healthcare’s Slow Pay Problem

Civ Robotics Hits the Road This November

Armilla AI Expands AI Risk Intelligence Toolkit at ITC Vegas 2025