Michael Krakaris

I’ve spoken to over 2 dozen MDs at PE firms I can confidently say that the arb of figuring out how to implement Vertical AI at portfolio companies is very real right now It will fundamentally change underwriting for those who can do it predictably and unlock generational returns. Most are aware they need to act. Very few have.

454

64 Comments

The difference between a $10K contract and a $100K contract is which budget you're competing for. Why startups can land contracts that are 10x larger than incumbents: A large platform focused on serving HVAC companies captures ~1% of their revenue. For example, a typical HVAC company making $1M pays the platform $10k. A startup, also specifically targeting HVAC companies, captures 4-10% of their revenue. The same $1M HVAC company pays the startup $40-100k. The difference is that the big-player platform is just another software expense, while the startup enables companies to operate with fewer employees. Replacing work lets your product capture a payroll budget that's 10x larger. This shift redefines your startup’s entire approach, while traditional platforms focus mainly on selling more seats and subscriptions. You focus on one industry and learn its operations inside out. You become part of their team. Big cos can’t work like this b/c they can’t focus solely & completely on a single vertical problem. Small teams can… and they have to. I’m interested in vertical AI companies that control entire workflows and are built by small teams close to operational work.

91

22 Comments

Here's a problem we see all the time in early studios: they copy-paste a VC fund's operating cadence and wonder why nothing feels right. Weekly deal flow reviews. Portfolio monitoring calls. Valuation-focused LP reports. All borrowed wholesale from a fund playbook. But a VC fund's primary activity is deal selection -- source, evaluate, check, board, wait. A studio's primary activity is venture creation -- generate, validate, recruit, build, launch. Those are fundamentally different jobs. When you run a studio like a fund, things break in specific ways: Your meetings are wrong. You're reviewing deal flow instead of venture build progress -- milestones, blockers, resource allocation. The work is building, not sourcing. Your team is wrong. Studios need builders at every level -- operators, designers, engineers. Not just investment professionals. You can't build companies with a team designed to pick them. 📉 Your metrics are wrong. Entry valuations and markups don't tell you anything useful. Cost-to-build-a-venture, time-to-market, and venture survival at 18 months -- those are the numbers that actually measure whether the studio is working. Your LP reporting is wrong. Report operational progress -- what's building, what's launching, what's been killed and why. Not just portfolio movements. Here's the lesson -- the studios that struggle most are the ones that adopted VC templates without modifying them for fundamentally different work. The portfolio companies don't exist until the studio creates them. Not a fund that happens to build things. A builder that happens to have a fund. The operating rhythm should reflect which one is primary. 🎯

10

1 Comment

AI isn’t just another technology wave, it’s reshaping how value is created, priced, and captured across software and services. As AI systems take on human-emulating tasks/ roles, pricing, margins, go-to-market strategies, and even valuation frameworks must evolve accordingly. We are excited to share our thinking in this three part series and would love to engage with founders and investors alike in this topic.

20

Samsara, ServiceTitan, and Procore Technologies have a combined valuation of $40B+ —and founders with wildly different industry experience. Yet VCs still debate whether it's needed to build great vertical software. As always, my stance is: It depends. The better question is: What type of founder are you, and what's your path to understanding your customers deeply? Some investors are adamant that you must have deep industry experience to build successful vertical software. Others claim outsiders have the advantage. Both camps love to cherry-pick examples that prove their point. But I've been advising and investing in vertical software companies for over two decades, and I think that's enough exposure to confidently conclude that founders of all backgrounds can be successful. Take these 3 examples (Samsara, ServiceTitan, Procore). They're some of the most successful vertical SaaS companies today. Some of the founders come from deep industry experience, but others have a background that would surprise you. → Procore's founders came from construction backgrounds and built a $10B+ company selling to their former industry. They'd lived the pain points they were solving for. → On the opposite end of the spectrum, Samsara's founders had zero experience in trucking or heavy industries. These MIT grads had just sold Meraki to Cisco for a billion dollars and were looking for their next challenge. They picked fleet management and transportation—two industries they knew nothing about. Today, Samsara is worth more than $20B. → Then there's Service Titan, which charted a middle path. The Stanford-educated founders didn't work in the trades themselves, but they grew up watching their parents run HVAC and painting businesses in Southern California. They bonded over their shared background and built a $10B+ company serving those same trades. So it's unreasonable to say that a founder's experience is the determining variable of success. Instead, what all 3 of these stories have in common is founders who deeply understood customer problems and built exceptional products to solve them. Industry outsiders often bring fresh perspectives and aren't constrained by "how things have always been done." Industry insiders have instant credibility and know which problems matter most. Those with adjacent experience can bridge both worlds. As an investor, I back founders regardless of their industry background. What matters most to me is their ability to build, learn rapidly, and maintain fanatical customer obsession. Where do you stand on the industry experience debate? I'd love to hear your thoughts.

34

10 Comments

SF VC Takeaway #2: Pricing expectations, performance bars, and what’s actually getting funded. One theme that came up repeatedly in SF was how far pricing expectations and performance bars have shifted, even compared to just a few years ago. A few things investors kept anchoring to: 1️⃣ Median Series A valuations are higher than their 2021 peaks, but fewer of them are getting done. 2️⃣ Capital is being concentrated into fewer and fewer companies (and lots of capital!) 3️⃣ “Good” progress is no longer enough and the bar for standout performance has moved in an AI-native world So what does “top performance” mean right now? One investor told me that top quartile seed companies in their portfolio are going from $0 to $2M in ARR in <12 months. Outside of pure traction numbers, a few other themes that came up to describe "top performance": 📈 Explosive early revenue ramps (or a very credible path to them) 📊 Strong velocity and momentum for 2 quarters in a row, even if the baseline is small. 🚀 Clear signals of category leadership, not just product-market fit. Sometimes shown by either domain expertise, speed of product optimization, or by lack of competition in the category. This creates a counterintuitive dynamic where it can be easier to fund a company with strong pedigrees in a hot space and no traction yet than a company that went from 0 to $1M ARR at what used to be considered a rapid pace. Pricing today is driven by trajectories, not moments in time. We used to say investors invest in lines not points; I think that's more true than ever now because crossing certain milestones doesn't carry as much influence as it once did. Finally, investors still say that valuation matters, but many of them are acting differently. Pace and belief in category-defining companies really sets the price; while slower growth gets scrutinized rather than discounted. One silver lining in the camp of durable growth: Series A rounds are happening so fast that many companies don’t yet have meaningful history of retention data. Large bets are being made on velocity before the durability is proven. Several investors told me the same thing: we may soon swing back to a market where retention, not growth, becomes the defining metric. Let's hope so. I'll share my third SF VC takeaway tomorrow!

59

7 Comments

Founders doing $5M+ don’t lose by picking the wrong channel. They lose by running too many at once. At that stage, complexity is the tax. Every channel can work. The mistake is spreading focus instead of scaling what already converts. The real question isn’t what’s new. It’s what’s predictable. If you had to cut everything but one channel tomorrow, which one survives?

11

5 Comments