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Two years ago I published an image of a rabbit on a fire truck to demonstrate how effective image generation was for blog posts.

The conclusion at the time : the images were unusable.

In 2025, the opposite is true - with one caveat.

Prompt: Coupa & Thoma Bravo logos each in front of a cloud with a plus sign between them.

2023	2025

Two years has brought tremendous professionalism to new image. Corporate street art is now pixel-perfect professional. The clouds and the + sign are perfect, and the logos look the part.

Software systems work best when they’re connected to each other. For years, incumbents use deep integrations as a competitive moat.

But AI upends this dynamic.

A few of our portfolio companies are starting to develop integrations with AI in a matter of hours, completely upending the two or three quarter timeframes of classic enterprise integration development.

This enables two important impacts to the sales cycle.

First, the integration a customer desires can be built during the sales cycle, demonstrating the startup’s technical agility.

I want to see how you use AI.

The biggest challenge to AI adoption is reimagining workflows, AI is best discovered socially.

Midjourney’s launch on Discord was brilliant. As a new user, I knew enough to ask for an image of a rabbit on a firetruck. But by watching others, I discovered I could create vector images, recast photos into Ghibli-style art, change aspect ratios, or convert photos to pencil-shaded drawings.

We don’t often hear the words speed & ERP in the same sentence. But when researching Doss, we heard it again & again. We’ve always believed fast sales cycles create competitive advantage - nowhere is this more true than enterprise software.

Imagine purchasing software knowing there’s a 75% chance it won’t deliver value after a 12-month deployment. If selling software is the business of selling promotions, traditional ERP offers a ponderous path to career advancement.

I’ve been watching my behavior evolve as I use AI more.

Coding new projects, I started first by describing a big idea : generate a new website that ingests podcasts and transcribes them. But I quickly discovered this approach was like asking someone to build a skyscraper without blueprints—the AI choked on requests too broad & lacking structure.

So I broke the project down into smaller blocks. Write a function to download the list of podcasts in the last week from these sites. But I noticed how low-leverage that felt : I knew I was yoking a strong animal to pull along a child’s wagon.

Pricing is one of the most complex topics in software. Changing pricing is never simple. It is a company-wide evolution that has the potential to completely reshape your entire business & your customer relationships.

Few have executed this transition better than Barr Moses, Co-Founder & CEO of Monte Carlo.

Join us for a candid conversation with Barr as she shares how Monte Carlo transitioned from ARR to daily revenue as the core operating metric for the business.

With another tariff induced red-tinged day hammering markets, I wondered: Do private markets follow public ones? The data suggests yes—but with a delay & at a fraction of the magnitude.

A 1% increase in Nasdaq’s (QQQ) quarterly return translates to a 0.47% rise in median Series A valuations—but only after a two-quarter delay.

The inverse holds true as well: when public markets contract, private valuations follow suit approximately six months later at roughly half the intensity.

The new tariffs have markets down broadly. What do they mean for startups?¹

In terms of first order effects, tariffs can impact a startup in two ways : the input costs and consumers’ demand.

Most software companies don’t import or source critical components of the software from abroad so the COGS / gross margin structure of the company shouldn’t change unless they rely on significant hardware purchases, for example GPUs or robotics components.

As startups scale, effective sales implementation becomes the difference between stagnation and sustainable growth. After analyzing hundreds of sales organizations across startups, I’ve distilled the key pieces of advice that founders and leaders should keep in mind.

1. Sales Strategy Fundamentals

• Start with the right price: Establish pricing that reflects value rather than just covering costs.
• Define your ICP: Clearly identify your ideal customer profile before building your sales process.
• Understand sales velocity: Recognize that sales success depends on both deal size and deal frequency—optimize for predictability.

Your first sales hire should generate predictable and consistent revenue, not just hunt elephants

We’re excited to announce our Head of AI, Bryan Bischof, and our first entrepreneur in residence, Philip Zelitchenko.

A practicing professor of data science at Rutgers and a Math PhD, Bryan has spent the past two decades building AI and data science practices across thought-leading startups, including Hex, Weights & Biases, Stitch Fix, Blue Bottle Coffee and many others.

Recently, he published his learnings on a year’s worth of learnings building with AI here.