Wall Street Occupies Linux OSS 2026

Welcome to Apereo. That’s what I said to myself 8 months ago. Our mission is straightforward: to deliver open source software and its benefits to the education community. 

My role is also simple: to rethink the money. Meaning, raise enough to remodel our external income sources until they’re sustainable. The preexisting trend wasn’t deadly, but neither was it positive. I have a running joke now: You know why we’re a nonprofit? Because we had no other choice.

This will be my 13th new career. Not because I’m a schmuck, but because I’m old and have done many things. I spent a decade as a line cook, from ages 13 to 23, then five years on the floor of the Pacific Stock Exchange, which was remarkably similar to cooking. The relevant part to what I’m doing today started in 1999 at Goldman Sachs, where I spent 15 years and lived in Hong Kong, Tokyo, London, and New York. Between that and Apereo, I spent 10 years as a sole proprietor, living off the fat of the land on the cusp of Wall Street.

The Linux Foundation OSS Summit in Minneapolis, May 18-20, was my fourth conference since I put away the Ferragamo ties. Just kidding, money doesn’t wear ties. In all seriousness, I see my role as bringing a bit of realpolitik to balance out the idealism of an open source nonprofit. The hosts of the Linux conference – oh boy – they certainly have not failed to focus on commerciality 😀.

Two opportunities stood out to me from my attendance and conversations. 

The first: the audience was way more remorseful about the next generation of engineers being dumbed down by using AI than it was enthusiastic about the prospect of everyone experiencing increased productivity. Likewise, universities seem to be experiencing their own existential angst: more fearful that AI will disrupt their current structures than focused on the opportunity to harness its power to deliver better-prepared students. Said to me by one senior corporate developer: his alma mater contacted him because the dropout rates within their CS department is showing an increasing trend. This datapoint kind of substantiated both hunches. Said another way, everyone raised their hand when they asked who is using agents to code, but the palpable sense of AI apprehension outsized even that response. 

I see an immediate opportunity to engage in conversations with universities about the benefits of OSS systems in mature, bureaucratic environments. And, it’s not just AI that’s breathing down the neck of their business model, but also funding cuts and enrollment slack too. However, bold changes happen amid times of hubris or hardship. Or, to quote Winston Churchill: “Never let a good crisis go to waste.”

We’re currently seeing interest in this message, too, as institutions are reaching out to Apereo on this exact topic. The time feels ripe to reinvigorate our efforts to evangelize OSS solutions in the LMS and SIS space; to be bold and ambitious, and to raise funds to support that undertaking and amplify any successes. On the university side, we should be pushing on unlocked doors. On the donor side, it’s a complex and esoteric message, but one with more tangible metrics than simply boosting OSS for the good of all students everywhere. 

The other religion that hit me: OSS needs more followers and fewer starters. Sixty-five-thousand new 501(c)(3)’s are not needed to support every new project. That process defrays the messaging and turns the funding conversation into, basically, a tank of dolphins yelping for fish. Linux, for good and bad, has done an excellent job of consolidating the space and owning the conversation – hence their success – but they have also done so at the expense of processing everything through a Linux worldview. Looking at the corporate universe, Microsoft and Cisco have each made more than 200 acquisitions in the last 2 decades. Linux Foundation is the one OSS sponsor that has most closely approximated this behavior.

On that note, one breakout session focused on the sustainability of OSS funding. It was suggested that open source projects might consider viewing salespeople as part of their necessary contributor ecosystem. Hear, hear! (DISCLAIMER: this next thought is just me advocating a point of view, rather than speaking for the organization) I would suggest that we, Apereo, need to be in the frame of amassing and gathering projects, plus acquiring other foundations, with an aim of likewise being gobbled up ourselves someday. It’s the way of the world: get bigger, get acquired, or go bankrupt. Those are realities in the commercial space just as they are for the nonprofit one. We cannot change it, so we must embrace it.  

In the meantime, this is how I see the remodeling of our funding framework looking:

1) Develop significant, meaningful relationships with corporate sponsors and benefactors such that becoming an Apereo member is a bilaterally meaningful arrangement rather than purely a charitable situation — companies are scarcely nice with money when it does them no good; 

2) Increase Apereo’s relevance by capturing the conversation about the role, and threat, of AI in computer science education, and to position Apereo as the central authority on university CIO trends, thoughts, habits, and appetites

3) Undertake the sales and fundraising efforts for projects under the Apereo umbrella, especially if projects have a “sellable” message; or to take heed what I heard in the Linux breakout session on OSS funding sustainability (making salespeople as part of their necessary contributor ecosystem); 

4) Aim higher and do something bigger. Impact raises money. The other way around is far less certain. We can use this moment of uncertainty to advocate for our cause and be helpful; but we should think up the food chain and do that with chancellor and provost-level decision makers. 

It has been a thoroughly exciting time to join something so boring. And, it’s unique that being boring is good. Just look at all the disruptions in the commercial SIS and LMS spaces. Arguably, the opportunity for open source in education is better now than when OSS was exciting. And, there is a saying in the sport of boxing:  there’s nothing more dangerous than a dazed fighter. I think we’ve got a great moment to take a bigger swing. The environment in commercial EdTech is about as challenging as the one facing their customers. If we do something big, I’m confident the funding follows. Anyway, we’ll see you all at the next conference. I go to all of them because I’m new. And, I’m easy to find. The ex-Wall Street guy in the yellow van who never wore a tie. 

See you at FOSSY in Vancouver. But first, Alaska.