Roger Ehrenberg

@HarryStebbings Once you develop your thesis, execute the strategy and don’t panic. Succumbing to FOMO and PR hype cycles is bad for your mental health and your returns.

The Single Biggest Lesson for Emerging Managers: "Liquidity windows open and close. When they are open, take advantage of them. Even your winners, you should be selling 20%-30%. Your job is to return money. DPI is math." What is your single biggest piece of advice to emerging managers @honam @chadbyers @NWischoff @infoarbitrage @rrhoover @TurnerNovak @packyM

The future is bright, and Simon Sokol, Ethan Ehrenberg and I are here to make Equipe ubiquitous across the sports and, eventually, the enterprise customer landscape. hashtag#data hashtag#infrastructure hashtag#fandom /fin

The Equipe business sits at the intersection of pretty much everything Game Changers Ventures cares about, and bringing our full capabilities to bear in helping Nick and Sajan to build the best business possible is truly a gift /3

We @gamechangersvc have been working with Nick Benson and Sajan Gutta from earliest days. We explored how our shared love of data, infrastructure, fandom, disruption and sport might help in a landscape short on modern technology but long on opportunity. The result was @EquipeHQ /1

Six months ago, we formally launched @gamechangersvc. It feels good — really good — to be back building a firm from scratch around ideas and domains where I have deep conviction. Even better is doing it with @ssokol94 and @ethanehrenberg, and with the founders we’ve had the privilege to back so far. Early-stage venture, when done right, is not a transactional business. It’s a deeply personal one. Our job is to help founders become the best versions of themselves — as leaders, as decision-makers, and as humans — while they attempt something very hard. I believe we’re doing that the right way. I also believe what we’re building into is not cyclical, but secular. AI will reshape almost everything about how we work and create. Paradoxically, that will only increase the value of being human together — gathering, belonging, cheering, participating, identifying with something larger than ourselves. Sports, entertainment, live experiences, and the technologies that power them sit squarely in that shift. To us, it looks like a generational opportunity. When I first announced the firm, I mentioned that we would eventually add one more partner-level person. That remains true. There is no job description. There is no timeline. There is no “process.” What there is: openness. We are looking for someone who is AI-native in their thinking, intellectually curious, comfortable with ambiguity, and genuinely passionate about sport, entertainment, community, and culture. Someone who wants to build a firm — not just join one. Someone who extends how we think rather than simply amplifying what we already do. This person may not currently be in venture. They may not even be in this sector. In fact, that could be a feature, not a bug. The goal isn’t incremental horsepower. It’s new perspective, judgment, creativity, and values alignment. There is also no rush. The right partnership is discovered, not hired. We’ll get to know this person over time, and they’ll get to know us. In all likelihood, this will be the last person we ever add. The aspiration is a very small, very high-trust, very long-term partnership — similar to what we built at @iaventures. That model worked pretty well, and it was a lot of fun. If this resonates with you — or with someone you think we should know — my inbox is open. roger@gamechangers.vc #LFG #vc #builders

My biggest takeaways from @sherwinwu: 1. AI is writing virtually all code at OpenAI. 95% of the engineers use Codex, and engineers who embrace these tools open 70% more pull requests than their peers, and that gap is widening over time. 2. The role of a software engineer is shifting from writing code to managing fleets of AI agents. Many engineers now run 10 to 20 parallel Codex threads, steering and reviewing rather than writing code themselves. 3. The average PR code review time has dropped from 10-15 minutes per PR to 2-3 minutes. Every pull request at OpenAI is now reviewed by Codex before human eyes see it, and Codex surfaces suggestions and catches issues up front. This allows engineers to focus on more creative and strategic work while dramatically increasing productivity. 4. The models will eat your scaffolding for breakfast. When building AI products, don’t optimize for today’s model capabilities. The field is evolving so rapidly that the scaffolding (vector stores, agent frameworks, etc.) that seems essential today may be obsolete tomorrow as models improve. 5. Build for where the models are going, not where they are today. The most successful AI startups build products that work at 80% capability now, knowing the next model release will push them over the line. 6. Top performers become disproportionately more productive with AI tools. AI tools amplify the productivity of high-agency individuals, so the gap between top performers and everyone else is widening. The ROI on unblocking and empowering your best people compounds faster than ever in an AI-augmented environment. 7. Most enterprise AI deployments have negative ROI because they’re top-down mandates without bottom-up adoption. Success requires both executive buy-in and grassroots enthusiasm. Sherwin recommends creating a “tiger team” of technically-minded enthusiasts (often not engineers) who can explore capabilities, apply AI to specific workflows, and create excitement throughout the organization. 8. The one-person billion-dollar startup is coming, but with unexpected second-order effects. As AI makes individuals more productive, we’ll see not just billion-dollar solo founders but an explosion of small businesses: hundreds of $100M startups and tens of thousands of $10M startups. This will transform the startup ecosystem and venture capital landscape. 9. Business process automation is an underrated AI opportunity. While Silicon Valley focuses on knowledge work, most of the economy runs on repeatable business processes with standard operating procedures. There’s massive potential to apply AI to these workflows, which are often overlooked by the tech community. 10. The next two to three years will be the most exciting in tech history. After a relatively quiet period from 2015 to 2020, we’re now in an unprecedented era of innovation. Sherwin encourages everyone to engage with AI tools and not take this moment for granted, as the pace of change will eventually slow. 11. AI models will soon handle multi-hour tasks coherently. Today’s models are optimized for tasks that take minutes, but within 12 to 18 months we’ll see models that can work on complex tasks for upward of six hours. This will enable entirely new categories of products and workflows. 12. Audio is the next frontier for multimodal AI. While coding and text get most of the attention, audio is hugely underrated in business settings. Improvements in speech-to-speech models over the next 6 to 12 months will unlock significant new capabilities for business communication and operations.

This is certainly one of the most relevant and timely pieces of thinking I’ve ever read.

Goodbye Toronto 🇨🇦 So excited to have officially moved to New York 🇺🇸 to partner with @infoarbitrage and @ethanehrenberg to build @gamechangersvc! To all sports, media & entertainment tech founders, don't hesitate to reach out. PS GO JAYS

I know Detroit well and am building several business there, and I can say Dan's perspective is spot-on. It's nowhere near time to declare victory - you don't fix 50 years of troubled history in a single generation - but the progress is real and has to be seen. #LongDetroit

If I recall, @joshk , didn’t the same thing happen to @square when they had a pre-IPO ratchet deal that seemingly cost a lot of money but ultimately paid off in spades for the founders? It’s insanely hard to do but wow, if you get it right…

This post is genius. It’s so hard to accept because of ego. But by ignoring ego and playing the long game, controlling emotions can unlock intrinsic value. Short-termism is a tax on our futures, especially for those with great ideas that take a longer time to unfold.

@HarryStebbings So yes, one of the best traits in deal making and in life is to listen. Actively. I want to listen, and to learn. Conquer this, and you’ll be in a better position to evaluate and to make better decisions. Always.

@HarryStebbings Humans want to talk. Humans are generally uncomfortable with silence. The ability to let others fill the empty spaces takes discipline and is a sign of pushing down ego to learn. Most people are really bad at this.

"Listen more than you speak, because movement is not action in deal-making. Talking the most doesn’t mean you’re in control, and silence doesn’t mean the other side isn’t listening. All deal-making is people reading people, one-on-one, in groups, and at scale." What are your single best pieces of advice to founders on deal-making @honam @infoarbitrage @ilyaf

@miehrmantraut @HarryStebbings totalrealreturns.com/s/DDOG

@HarryStebbings @infoarbitrage Pretty every VC worth its salt dumped those before or during the IPO.

We have a big problem. The venture model doesn’t work with the current public market revenue multiples. Datadog ⬇️ 21% Figma ⬇️ 20% Wix ⬇️ 38% Braze is 2.5x ARR Atlassian is 4.8x ARR Klaviyo is 4.5x ARR Venture doesn’t work unless this changes. Agree @infoarbitrage @bgurley @jasonlk @rodriscoll?

No. It’s not just about multiples - it’s about competitive positioning, growth rate and margin dynamics. Multiples are what they are for different reasons - interest rates, sector preferences, growth rates, margins, etc. You can’t lock into a single metric and look at it in a vacuum. And you certainly can’t extrapolate from a handful of companies - too many conflating variables at work

@infoarbitrage @HarryStebbings If that was true, just buy the proven revenue from Wix / Datadog and wait for multiples to come up. No reason to invest in startups at a tiny fraction of the size.

It’s time for sponsorship to go the way of programmatic advertising - there’s no need for the manual matchmaking that dominates the industry today. Much as I believed that almost all ad buying would begin to resemble quantitative trading back in 2009 (note: @TheTradeDesk), I believe that @AnvaraHQ is the catalyst for bringing this model to brand sponsorship and inventory monetization. @gamechangersvc sportsbusinessjournal.com/Articles/2026/…