boldstart technical founder summit — AI giveth and AI taketh away + other 🔑 learnings
I’m still processing all of the discussions, side bars, and late evenings from our boldstart Founder Summit in Miami. All I can say, is if you’re an investor and haven’t organized one of these, then I suggest you do, as there is nothing better for founders than to just have the time to geek out with one another in a safe space and explore what’s new in the world. This equally applies for founders running companies >$100M ARR and for those just starting. Being a founder can be lonely and Steven and Grant sum it up well 👇🏼.
AI giveth and AI taketh away
AI giveth — there was an excitment and buzz this week as founder after founder had their laptops open showing their latest rev and iteration of their new, new thing which was, of course, mostly agentic and AI-powered. There was this feeling that no matter how big or small you are, there is always a chance to reach escape velocity 🚀 at any time if you build the right product with the right “wow” factor. The feeling that any one could be the next Bolt.new was inspirational. For those who don’t know, here’s the story 👇🏼
At the same time, no one is immune as AI can taketh away. It can taketh away PMF! There was this fear also of what happens when I’m already established and my competitors come for me with an AI-native stack with no technical debt. Yes, AI can equally taketh away so PMF has to be a recurring idea as it’s not a point in time like a balance sheet but a living, breathing thing that constantly needs to be fine tuned, evern more so in the world of AI where the moats to build are even lower.
AI Coding
One of the hottest topics was around the best tools for using AI in coding. As I walked around the room it was pretty cool to see both younger first time founders and older vets just banging away prototyping and coding and sharing best practices on coding with Cursor, Windsurf, Codebluff or all of the above. These founders have drunk the Kool-aid and everyone repeatedly told me what used to take hours only takes minutes now. Bolt.new was definitely another favorite among boldstart founders for rapid prototyping but not for production. There was also lots of discussion on whether we need Figma or not if one can easily speak in code and get what you want versus designing and turning into code. One founding team has a dedicated engineer on staff to just test every new coding product to figure out the best way to keep up and get more efficiency for the rest of the team.
Agents
Another interesting deep dive was around the Future of Agents led by Joao Moura, co-founder and CEO of CrewAI (one of our portfolio companies). If you’re wondering how enteprises are going to adopt agents Joao let the session know that >50% of the Fortune 500 already has a developer using the framework. We’re still in the early innings for enterprise adoption and much of the conversation shifted towards my favorite topic on second order effects when agents outnumber each human 1000 to 1 and the infrastructure one will need to think, build, see, host, manage, operationalize, secure, and scale these 😲!
As Joao heard in SF, the future will be the shift from B2B to B2A to A2A.
Once again, what kind of infra will be needed to support a world where agents are doing 90% of the work versus humans?
Data
Finally, many founders just emphasized the importance of data — foundational models are a commodity, but it’s the data that matters — how to create proprietary data or get that data creates a significant moat over time.
Bottom line — the world is moving so fast and none of us really know.
Recap — velocity, think bigger
It’s hard to synthesize all of the discussions and self organized talks, but here’s my best attempt.
👇🏼 from my partner Eliot Durbin:
Nadia from Codeyam:
Going back to my first point, it’s all about innovating and keeping up the velocity. ❤️ this from Patrick Collison of Stripe — “the tyranny of being first” which shows how hard it is for first movers to always stay ahead and how one must contanstly fight bloat (Fortune Term Sheet).
Building an Exothermic company — Scott Yara
Last but not least, one of the highlights of Founder Summit was having my long time friend and legend Scott Yara join us for a fireside chat on building software companies over 3 decades. We first met back in 1999 when I funded the company which would pivot multiple times to become Greenplum Software, a scalable data warehouse built on OSS PostgreSQL and commodity hardware which would later get sold to EMC of hundreds of millions of dollars and eventually spin out and IPO as Pivotal Software. Scott is now building companies at Sutter Hill Ventures with Mike Speiser who helped start Snowflake — so many 💎 from his talk…
Here are a couple enduring lessons Scott shared, best summarized by my Partner Ellen Chisa:
Build an exothermic company – revenue should be more than all the money you spent, employees should get more out of it than they put in.
If you ever let up or assume success is guaranteed, it’s game over.
Run towards the best people you can find who will let you work with them. There’s a reason that staging works well in restaurants. Being a line cook in the best restaurant teaches you what excellence looks like. If it’s not time to build, go somewhere excellent.
Scott Yara, founder of Greenplum, sold to EMC, spun out as Pivotal Software, IPO, sold for $4B, now partner at Sutter Hill Ventures
Nadia Eldeib, co-founder and CEO of CodeYam, wrote her own summary from the founder’s perspective which you should read here (AI-first Software Development + Lessons from boldstart Summit 2025)
While last year AI-curiosity was a strong theme, this year everyone was sharing learnings and how they’ve adapted how they build software and, in some cases (like ours), what they’re building to leverage the superpowers AI can provide for software development.
This year’s format was an unconference with experienced founders hosting off-the-record discussions on prevalent themes.
Without getting into the off-the-record nitty gritty details, there were four categories that stood out to me in terms of the topics discussed:
- The Evolution of Developer Experience
- AI’s Transformation of Software Development Workflows
- Product Comes First. But What About AI Agents as Users?
- Business Insights for Technical Founders
Our checkbooks are open as we continue to seek bold, technical founders building on the fringes, the ones who are often misunderstood, creating the categories of tomorrow. We’d love to have you nerd out with the the broader boldstart community which is all enterprise focused but also encompasses deep technical builds on the edges like robotics and bio and ???.