OP #276: Agentic Commerce, Bitcoin, and Antonio Brown's X feed

Author

Darren Herman
November 19, 2024

Happy Tuesday! It’s been a couple of weeks since the OP graced your inbox, and let me tell you—it’s been a whirlwind around here. Despite my best efforts to stay consistent this year, sometimes life and work collide, and something has to give.

That said, I’m thrilled to be back with this week’s edition, and I had a blast putting it together. Lately, I’ve been deep in thought about Agentic Commerce—a concept that’s both fascinating and full of potential. In today’s OP #276, we dive right into it. In addition, I’ve added a CMO job at a Bain Capital PE portfolio company. This is a packed letter.

🎵 While writing this OP, I listened to the band, Dispatch. I share “Only the Wild Ones” - live from the Boston Woods with you. If you haven’t been introduced to Dispatch or you are a longtime fan, this is a beautiful version. It reminds me a ton of Simon & Garfunkel, whom my father used to listen to often as we grew up. If you want to go a bit deeper, here is another Dispatch song I’ve been enjoying: Elias (link to my favorite jam part).

🎥 Similar to my pal Eric Franchi, I too am bullish on the future of CTV ad tech. With that said, we have a long way to go for streaming events. I tried to watch the Tyson vs. Paul boxing match and like many of you, ended up receiving buffering errors. I ended up catching the live stream on X through Antonio Brown of all people. I was able to watch it there with zero lag or buffering.

💰 I am eyeing the The Microstrategy Portfolio tracker. Unfamiliar with Microstrategy? It’s a software maker who purchased Bitcoin in 2020 as a hedge against inflation. Well, this worked and it now has over $26B in Bitcoin which apparently is larger than IBM and Nike cash holdings.

📊 I am a sucker for good charts. Check out this post by Azeem Azhar of Exponential View which looks at how fast technology transitions are happening. The last chart which showcases the need for AI Agents to create knowledge vs. the declining world population is scary when you think about it.

💡 I received a message last night from my friend Tyler who works at Shopify. It was an extremely timely message as this OP is all about Agentic Commerce. Shopify has just partnered with Perplexity around commerce. If you are a merchant/shop owner, you’ll want to sign up here. It feels very Amazon-esque in terms of features, but Perplexity has big ideas on where to evolve this.

✨ If we’ve spoken lately, you know I’m thinking about the impact of feed algorithms on society, especially children. We all are influenced by our filter bubbles and it’s more pervasive than ever. I’ve been talking about how the feed algorithms should reset every 30 days or so. Well, Instagram isn’t doing that quite yet, but this is a step forward.

OK, lets start off with some fun reads:

I hope your week is off to a great start. Thank YOU for subscribing and if you know anyone who would like to receive the OP, feel free to forward it or share the link: https://www.opletter.com/subscribe/

-Darren

The Agentic Commerce Era: A Personal Take

In his compelling piece on Agentic Commerce, my colleague Scott painted a vivid picture of a future where AI shopping agents revolutionize consumer behavior. Inspired by his insights, I’ve been mulling over what this could mean in practice. For those not familiar with agentic AI, here are two good videos that explain the compound system concept. The big enterprise example of Agentic AI that was just released is Agentforce by Salesforce or the Perplexity Shopping which Shopify is partnering with them on (read more).

Back to the original topic:  digesting the original piece by my colleague Scott Friend and responding with some thoughts below.

Digital Twins and Low-Friction Purchases

Imagine having a digital twin—a virtual shopper handling your routine, predictable purchases. For me, the starting point feels obvious: low-friction, frequent buys like toilet paper, toothpaste, and paper towels. These are the subscribe-and-save staples of my Amazon orders today. Transitioning those decisions to an AI agent wouldn’t just save time; it could ensure I never overstock or run out. It’s convenient and we could see the transition from Subscribe & Save to being managed by my agent.

But there’s more. I picture setting volume and price triggers for purchases. If toilet paper hits a certain low threshold (detected through IoT sensors, perhaps?) or if a favorite brand drops below my target price, the agent acts. Fully autonomous replenishment might require integrating IoT devices into the home, creating a feedback loop where your agent knows when supplies are dwindling and finds the optimal moment to restock. With that said, you do not need IoT to make this happen, it only enables the autonomous loop a bit easier.

Turning Purchases into Assets

What if the products we buy didn’t just sit idle when unused? Borrowing a page from Tesla’s playbook, could these agents transform purchases into income-generating assets?

Say my agent knows I bought a high-end camera or designer bag. Could it work with marketplaces to "rent" these items when I’m not using them or list them for resale as soon as demand spikes? Such functionality could challenge traditional resale platforms like eBay or The RealReal—unless those platforms find ways to integrate agentic commerce into their models.

The Role of Influencers in an AI-Driven Market

Even in an agent-driven economy, influencers and tastemakers will continue to shape demand. Whether it’s choosing between Alo Yoga and Nike or Porsche and Audi, cultural influence won’t go away. What will evolve is how those influences get translated into algorithms. A well-tuned agent might nudge you toward Alo sweats over Nike joggers because it “learned” your preference through the social content you consume.

The Agentic Interface: A New UI Frontier

The evolution of agentic commerce interfaces intrigues me. Will we have dashboards showing what we’re currently purchasing versus what’s available at better prices? Could we command agents to optimize every aspect of a transaction in real time? These early UI experiments will likely determine how quickly we adopt the technology. I’m curious about the design principles that will emerge to make these interfaces both intuitive and powerful.

Supply: The Hidden Hurdle

While demand-side automation seems achievable, the supply-side integration might be trickier. How will sellers onboard their products into agentic ecosystems? Will it require new APIs, or can platforms like OpenAI leverage existing infrastructure to seamlessly integrate sellers? For this to work at scale, the tools need to be simple, universal, and frictionless—no small feat when supply chains are involved.

We’re at the dawn of the Agentic Commerce Era, and the possibilities are exciting. What excites me most is how this blend of AI, IoT, and commerce will create opportunities for both consumers and businesses. The question now is, who do we prepare for this evolution of consumer behavior? Make sure to read Scott’s post. Let me know if you are working on something in the agentic commerce space.

Chief Marketing Officer Role: Leading provider of cloud-based enterprise SaaS solutions for K-12 education in North America

From time to time, I include jobs in the OP that I find interesting. For this particular one, it’s a new company in the Bain Capital Private Equity portfolio and I’d get to work with you. If you or someone you know are qualified, please reach out to me with your CV/resume.

PowerSchool is the leading provider of cloud-based enterprise SaaS solutions for K-12 education in North America, with a mission to enhance the education ecosystem through unified technology that empowers educators and helps students reach their full potential. Formerly part of Pearson Education, PowerSchool was spun off by Vista Equity Partners in 2015, went public in 2021 (NYSE: PWSC) and was recently acquired by Bain in October 2024.

PowerSchool connects students, teachers, administrators, and parents to improve student outcomes, offering a unified platform for managing state reporting, special education, finance, HR, talent management, learning, grading, and analytics. Serving over 60 million students globally and more than 18,000 customers—including 90 of the top 100 U.S. school districts by enrollment—PowerSchool generates approximately $780 million in revenue.

The company is seeking an experienced Chief Marketing Officer (CMO) to lead all aspects of the marketing organization as the company grows into a billion-dollar business. The ideal candidate will be a full-stack marketer with a strong emphasis on demand generation to support the company’s growth goals. Experience in vertical SaaS, international growth (both organic and inorganic), and managing multi-product companies is highly preferred. West Coast-based candidates are ideal.

If of interest to you or someone you know, please reach out to me. We have Heidrick & Struggles running the search and I’ll pass along all qualified candidates to them.

Below are a few articles I came across this past week that I found interesting. While I may not agree with everything in each one, I think they're worth a read. If you stumble upon an article you think I or the Operating Partner community would enjoy, feel free to share it with me. Of course, I reserve the right to decide what gets featured in the OP.

Always Be Launching (Andrew Chen)

Former Lawyers (Fred Wilson)

Former Lawyers (Fred Wilson)

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