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.

Our guest this week is David Gardner, Cofounder of The Motley Fool. David is one of the best stock pickers of his generation. While for many investors a single 100X investment would be a career-defining win, David has earned a 100X return on 6 companies including Nvidia, Tesla, Amazon, and Netflix. We talked about breaking the rules of investing, optionality, valuation, letting winners run, and much more. David is one of the investors I’ve learned the most from over the years, so I really hope you enjoy this one.

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

David Zhou is an investor in emerging managers, an angel investor, a blogger, and the host of the Superclusters podcast. We talked about how LPs can size up emerging managers, how VCs can stand out, portfolio construction, and which of sourcing, picking, and winning is the most important. We also explored:

+ Why David thinks that “access beats picking (then winning)” for most emerging managers—and how check size changes that calculus.

+ Follow-ons: when “all or none” makes sense, how signaling risk compounds past Series B, and why selling by Series C can be clean for seed managers.

+ LP incentives in the wild: marks scrutiny for new managers vs. “ignorance is bliss” for existing ones—plus how TVPI vs. IRR targets shape decisions.

+ The tough-love playbook behind “Dear Emerging Manager” and “Dear LP,” and why sloppy valuation methods and survivorship bias mislead GPs.

+ Differentiation framework: sell the market → the strategy → then you; use “flaws, limitations, restrictions” to confront the elephants in the room.

+ Fund design realities: reserve strategy, fund size vs. dilution (esp. in hard tech), and why some LP minimums are a built-in constraint.

+ Context from fresh market data: median seed at ~$20M and AI capturing a huge share of early deals—what those trends mean for formation and pricing.

+ Plus: Abe Othman’s follow-on finding (funds that never follow on beat always-follow funds 63% of the time) as a jumping-off point for David’s take.

Investing in Startups is a Seaplane Ventures production hosted by Joe Magyer.

We're trying something new with our first roundtable! Our guests are Sonia Nagar from SNAK Venture Partners and Colin Gardiner from Yonder Ventures. Sonia and Colin are both early-stage investors, friends of mine, and experts on marketplaces and network effects. We talked about AI’s role in marketplaces, why network effects aren’t more popular (even though they should be), how to make your own luck, what it’s really like to raise your first venture fund, and more. I hope you enjoy and thanks for listening.

Investing in Startups is produced by Seaplane Ventures.

Our guest this week is Hunter Walk, Co-Founder of Homebrew and Screendoor. Hunter has a deep background in product, including from his time at Google and YouTube, but is best known for his investing. Homebrew’s big wins over the years include Chime, Plaid, Gusto, Cruise, and more. We talked about trust and context, product, funnel math, investing life after LPs, and why Hunter isn’t as fussy these days about valuation.

Here's a longer rundown of the episode:

Homebrew → “Forever.” Why Hunter and Satya moved from an LP-backed seed fund to a self-funded evergreen model—and why they accelerated the shift in 2022.

Ditching ownership targets. Early-stage “must-own X%” rules create artificial scarcity for founders; Homebrew now fits their check into whatever round construction serves the company best. Prioritizing alignment with founders and co-investors over leading every round.

Valuation: what it really signals. Price matters less as a target and more for what it reveals about the founder’s decision-making, who’s on the cap table, and the path to the next round—especially when you don’t hold reserves.

Trust + context > generic advice. Hunter’s operating model with founders: build trust to have honest conversations, and keep real context so advice is specific—not just a blog post link.

Meeting math & magnets. You can’t jump into every haystack—so create magnets (writing, references, approachability) to pull the right needles; historically ~1 investment per ~100 inbound companies.

Your company is a product. Hiring, comp, and cadence must cohere like a product system; inconsistency is the cultural anti-pattern.

Focus areas now. Still heavy B2B dev tools (increasingly AI/ML) and FinTech; comfortable as #2–10 on the cap table alongside specialists, which expands where they can help.

Against multi-gen for most firms. Hunter argues many venture franchises lose “fidelity” as AUM and headcount grow—like copies of a mixtape over time.

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

Joe Magyer is the host of Investing in Startups, but his real job is running his early-stage boutique, Seaplane Ventures. In this episode, Joe is interviewed by his friend Owen Raszkiewicz, Founder and CIO of Rask Group and host of the Australian Investors Podcast. Joe talked why he made the move from public to private markets, how small firms can compete with big firms, the current venture landscape, putting AI to work as an investor, and why studying up on unit economics is a core part of early-stage investing. Please enjoy.