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CensusSecurity
Every SMB security and resilience framework starts with the same question — what are your critical systems, and what does an hour of downtime cost you? — and almost no SMB can answer it. The Business Impact Analysis is the foundation of every continuity, disaster-recovery, cyber-insurance, and third-party-risk program, and it is the step everyone skips, because doing it the traditional way means months of consulting hours nobody budgeted for. So the BIA either doesn't exist, or it's a stale document from three vendors ago that no longer matches the business. The auditor, the insurer, or the incident finds the gap at the worst possible time. The deeper structural problem is the buyer: the SMB is not equipped to produce a defensible BIA on its own, and shouldn't have to become a security expert to get one. The party that already serves them — the MSSP or vCISO practice — is the right place for this capability to live, but the providers have been stuck doing BIAs by hand, one expensive engagement at a time, which is why most of their SMB book has no current BIA at all. CensusSecurity automates the analysis and editions it for both sides of that relationship: an SMB Edition for the business and an MSSP Edition for the provider running it across a book of clients — so a defensible, framework-aligned BIA goes from a months-long consulting project to a same-day artifact.
TIE Connect Napkin Winner — name withheld
The napkin contest at TIE Connect this month was a simple format: pitch the idea on a napkin, and the room helps pick the one worth building. The winner is not a brand-new idea on a brand-new domain. It's an existing platform with years of compounding network effects, a real user base, and a founder who has been building the same audience long enough that the data itself is the moat. The problem the winning pitch identified isn't 'this needs to exist' — it already exists and works — it's that the next phase of growth is gated behind one missing capability, the kind of module that is expensive and slow to build the traditional way and is exactly the sort of thing an AI-native, additive engagement can deliver fast without touching the parts that already work. That's a different shape of problem than a 30-day cold start, and it's the shape Silverback expects more of its work to take: not rebuild the platform, add the one surgical piece that unlocks the next phase, leave the existing stack and the existing network intact.
PIM
Angel investors lose money in a predictable way. They back the founder they connect with, in the industry they happen to know, at the valuation they happened to be offered — and they call the pattern instinct. The disciplined ones don't; they screen every opportunity against their own criteria before a dollar moves. Karen Rands has spent two decades teaching exactly that discipline through the Compassionalist Academy — a deal-screening framework that scores an opportunity against the investor's real capital capacity, the industries they actually understand, and the deal stages and structures they're equipped to underwrite. The framework worked, but it lived in an Excel workbook, and an Excel workbook does not onboard the next thousand investors, does not enforce the method when the investor is tempted to skip it, and does not travel past the people Karen can personally train. The cost of the missing discipline is concentrated and real: the single most common way an angel check goes to zero is an investor abandoning their own stated criteria the moment a charismatic founder is in the room. PIM makes the methodology repeatable: build an investor profile once, then score every deal against it and get back a single, explainable signal — not a prediction, not advice, a discipline check the investor can audit.
PodToBook
A podcaster with a few hundred episodes has already written a book — they just haven't assembled it. The words exist, in order, in their own voice, sitting in transcripts nobody has turned into anything. Historically the gap between 'I have 150 episodes' and 'I have a book' was a services business: a ghostwriter or editor working through hours of audio at thin margins, a months-long engagement, a price point that only made sense for hosts who were already famous. That math kept the overwhelming majority of podcasters' back catalogs locked up as audio that depreciates the day after it publishes. The structural insight is that the expensive part — clean, structured, searchable transcripts of every episode — is already produced as a byproduct of putting a podcast online the modern way. Once that pipeline exists and the drafting is done by AI rather than billed by the hour, the economics flip: assembling a book from a back catalog stops being a bespoke services engagement and becomes a productized bolt-on. PodToBook is that bolt-on — same source material as the show's website, a different output, run by its own operator.
SundaySync
Every household runs the same ritual and most of them hate it: the Sunday-night scramble to reconcile the week ahead — who's where, what's due, who drives whom, what's for dinner, which kid has which practice, which parent has which conflict. The information is scattered across a shared calendar, three group texts, a fridge whiteboard, and two people's memories, and the reconciliation is manual, repetitive, and just important enough that getting it wrong costs a missed pickup or a double-booked evening. Existing tools make it worse, not better: shared calendars are passive databases that still require a human to do the cross-referencing, and family-organizer apps optimize for engagement — more notifications, more time in the app — which is exactly backwards for a problem whose entire point is to free up the evening. The product that actually solves this has to be measured by time off the app, not on it: it should collapse the planning into the smallest possible interaction window, surface only the conflicts and decisions that need a human, and then get out of the way so the family can spend Sunday evening together instead of negotiating a calendar.
30 years as a CTO. 2 years rebuilding everything around AI. This is what that looks like at speed.
Founder of Silverback CTO and Silverback Ventures. General partner at CogleGroup. Host of Tales From The Sky Lounge.
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