Connor Brennan-Burke and Manu Ebert are the co-founders of Hyperspell. Hyperspell provides a memory and context layer to AI agents is one of our portfolio companies at Seaplane Ventures. I was trying to explain to some friends at a BBQ recently Hyperspell what did and learned pretty quickly that most people aren’t familiar yet with AI agents. So! I thought it would be great for listeners to have Connor and Manu to come on to talk about AI agents, the evolution of AI, context, Y Combinator, and how Manu once bought a .AI domain name via fax machine.

From chatbots to true agents – Conor breaks down where tools like ChatGPT stop and AI agents begin, and why the key shift is agents taking actions autonomously across your tools, not just answering questions.

Why context is the real bottleneck – Manu and Conor share how building their own “chief of staff” agent led them to Hyperspell, a memory and context layer that plugs into tools like Slack, Gmail, and Notion so agents can actually understand your customers, org chart, and tech stack.

The three bottlenecks to agent adoption – Manu explains why verification, capability, and context each limit what agents can do today, and why decoupling these layers (rather than relying on a single big lab) gives companies more flexibility and avoids platform lock-in.

Why workers aren’t using AI (yet) – Conor reacts to studies showing most desk workers rarely touch AI, and argues that fear, bad framing (“AI will replace you”), and lack of personalized context are holding back adoption despite models already outperforming humans on many benchmarks.

AI as global leapfrog, not just US office automation – Manu highlights under-discussed upside: primary care in Africa, McKinsey-grade advice for small businesses, tailored guidance for farmers, and always-on tutors that could reshape opportunity in developing markets.

Let machines be the cogs, not people – The pair paint a future where AI agents handle status updates, follow-ups, and information shuffling inside big orgs, freeing humans to do creative, high-leverage work instead of feeling like dehumanized “TPS report” machines.

Building SuperMe and all-star AI teams – Conor shares a favorite customer use case: cloning experts (or even yourself) as agents using your own docs, email, and notes, so a solo founder can effectively “hire” an AI team of world-class operators and advisors.

YC, rejection, and founder stubbornness – Conor and Manu talk about finally getting into Y Combinator after nine applications between them, why persistence is a superpower for founders, and how YC has shaped Hyperspell’s trajectory.

Investing in Startups is hosted by Joe Magyer and produced by Seaplane Ventures.

Courtney McCrea is the Cofounder and Managing Partner of Recast Capital. Courtney and I dove into the intricacies of investing in emerging managers and building those firms. We talked about why Courtney is so enthusiastic about emerging managers, the challenges emerging managers face and how to overcome them, how LPs can better evaluate emerging managers, and why LPs aren’t racing to adopt AI as fast as their VCs.

We also discussed:

How LPs really evaluate first-time fund managers: beyond pedigree, what creates conviction in sourcing, selection, and portfolio construction.

Fund I fundraising strategy: why “spray-and-pray” outreach fails—and how to identify the right-fit LPs instead of chasing every allocator.

Where to start if you’re raising your first venture fund: go “off the beaten path” rather than leading with mega-institutions and public pensions.

LP diligence that actually matters: Courtney’s framework for reference calls, risk lists, and finding the “fatal flaw” early.

Solo GP vs partnership risk: why “GP divorce” can be a bigger underwriting risk than the classic “hit-by-a-bus” concern.

AI in the LP workflow: what Courtney is seeing (and experimenting with) in diligence and decision-making as venture processes modernize.

Joe Magyer is the host of Investing in Startups, which is a Seaplane Ventures production.

Dan Teran is a Cofounder and Managing Partner of Gutter Capital. Gutter is an early-stage firm based out of New York focused on founders tackling the world’s toughest problems. We talked about why Gutter invests with conviction, why they seek out founders with unique insights rather than Gutter trying to dream up their own, and how AI can solve problems in the real world, not just online. We also dug into:

+ Gutter’s core focus on vertical AI, vertical SaaS, and marketplaces tackling messy, real-world problems

+ Why Dan gravitates toward underestimated, “lived-experience” founders over polished, pedigreed profiles

+ Inside Elbow Grease, Gutter’s AI accelerator: structure, check size, and how they plan to keep backing winners

+ How Gutter turns talent into a product: embedded head of talent and heavy support on early hiring

+ The firm’s discipline on valuations, small fund sizes, and staying aligned with founders in a top-heavy market

+ Why Gutter insists on taking a board seat at seed and how that sets companies up for stronger Series As

+ Dan’s lessons from selling Managed by Q to WeWork and why founders should build acquirer relationships early

+ Two contrarian views: second-time founders are overrated, and the best founders do want real help from their investors

Investing in Startups is produced by Seaplane Ventures and hosted by Joe Magyer.