Killian Portfolio
8 bets · Apr 27, 2026

Nightly Briefs

Awaiting your verdict (8)

bet_20260427_65c808 · proposed
Batch-mode social tool for ADHD makers
judge 76/100edge 1.5/10ai native

Indie makers with ADHD are watching their shops stall because they can't post consistently — and the 'fix' is hiring a $500/mo social manager they can't afford on $2K MRR. Buffer and Later solved scheduling a decade ago, but every morning the user still stares at an empty caption box. That blank box is the disease; schedulers treat the symptom.

Roughly 50K neurodivergent product creators fit the bullseye. At 2% capture and $15/mo, that's $180K ARR — thin. Widen to indie makers broadly (Etsy + Gumroad, ~2M sellers) and 0.3% capture at $15 gets us to $1.1M ARR. Real, but not a rocket.

The wedge is opinionated content scaffolding paired with a one-session-per-month batching flow. Nobody ships pre-written, product-aesthetic-aware captions inside the scheduler — Copy.ai is generic, Buffer is infrastructure. Why now: the ADHD-creator identity went mainstream on TikTok in the last 18 months; the audience self-identifies and clusters.

Honest disclosure: this has zero overlap with your operator edges. You'd be backing the thesis, not leveraging unfair advantage. Defensibility is also weak — incumbents could ship 'ADHD mode' in a sprint.

The path is cheap: 14 days, ~$0 capital, a Notion template seeded in r/ADHD and maker Discords. Kill if <15 downloads by day 14, <5 paid conversions by day 30, or first-cohort churn above 60%. We learn whether the funnel converts before we build software.

It's a $0 test of a real, documented pain. Let's see if it pulls.

Problem
ADHD/neurodivergent product creators struggle with social media consistency (overwhelm + executive dysfunction), forcing them to hire help they can't yet afford, losing growth momentum.
Solution
Templated, low-friction social content batching tool: pre-written captions for product aesthetics + functionality, scheduled in batches (1 hour setup per month, not daily).
Target
~50K indie makers/creators with ADHD/autism targeting niche communities; willingness to pay ~$10–30/month evident from hiring social managers.
First test
Create 4 weeks of template captions (for aesthetic + functional product posts) as a Notion template. Post in r/ADHD, maker communities. Target: 30+ template downloads, 10+ paid conversions at $15/month.
Kill criteria
<15 template downloads by day 14 OR <5 paid conversions ($15/mo) by day 30 OR week-2 retention below 40% of paid users (i.e., ≥3 of first 5 paying users cancel before day 30) → kill; if downloads hit 30+ but paid conversions remain <5 by day 45, treat as conversion architecture failure and kill the current funnel
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bet_20260427_6da740 · proposed
Transparent-cost Copilot for indie devs
2026-04-27 · hn:ask_hn
judge 75/100edge 1.5/10infra tooling

Every indie dev I know got the Copilot price-hike email, then watched Cursor swap to opaque 'fast requests,' then heard Cline horror stories about $50 surprise bills from a single refactor session. The pain is loud and current: Reddit and HN threads are full of devs asking 'what's the cheapest honest alternative?' and getting no clean answer.

There are 50k+ price-conscious US indie devs paying $20-30/mo for Copilot today. Capture 2% at $10/mo paid tier = $120k ARR off the first cohort, with a clear path to $1M if we hit the vocal-indie segment on HN. Not a unicorn — a real lifestyle business if the funnel holds.

The wedge is narrow but specific: nobody — not Continue.dev, not Cline, not Cursor — shows per-request cost in real time with a hard monthly dollar cap. That's the entire 'surprise bill' problem solved as a product primitive, not a settings page.

I'll be honest about the risks: Continue.dev is OSS and one motivated contributor could PR a cost ticker in a weekend. And transparency might cannibalize our own upsell — if users see they're only burning $2/mo, why pay $10? Those are real.

So the test is cheap: 14 days, ~$2k for an Anthropic-backed VSCode extension with a live cost ticker. Kill if <150 installs by day 14, <5 paid signups by day 30, or Continue ships the feature first. No edge here beyond execution speed — I'm not pretending otherwise.

Small bet, fast signal, clean kill criteria. Let's run it.

Problem
Software developers frustrated by GitHub Copilot price increases and unpredictable billing; want transparent-cost alternatives that work in VSCode.
Solution
Open-source VSCode extension bundling multiple cheaper LLM providers (Claude, Grok, local LLaMA) with per-request cost display and hard spend caps.
Target
Independent developers and small teams (50k+ in US); currently paying $20-30/mo for Copilot. Would switch for <$10/mo transparent pricing.
First test
Build minimal VSCode extension with Anthropic Claude backend + cost ticker. Release on marketplace. Measure: 500+ installs in 14d and 10+ paid tier signups?
Kill criteria
<150 installs by day 14 OR <5 paid tier signups by day 30 OR day-7 retention below 20% of installers (measured by active API calls) OR a Continue.dev cost-visibility feature ships publicly before day 45 → kill or hard pivot
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bet_20260427_aa1728 · proposed
Scale + legibility for tiny Etsy products
judge 75/100edge 1.5/10info product

Etsy buyers message sellers every day asking 'how big is this really?' even when the size is in the description. For the seller of 1-inch D&D tokens or engraved jewelry findings, that confusion is a lost sale — and PhotoRoom and Pixelcut, the supposed AI photo saviors, strip backgrounds but do nothing for size context or text legibility on micro-products.

The pond is small but real: ~500K active Etsy sellers move physical goods, and a defensible slice — call it 50K serious micro-product sellers under 2 inches. At 2% capture on a $9 one-time guide, that's ~$9K to validate; a $5/mo SaaS at 2% is ~$60K ARR. Not a unicorn — a probe.

The wedge is narrow and honest: 'scale overlay + text sharpening in one click,' which incumbents haven't bothered to ship because micro-products aren't their ICP. That's also the risk — Pixelcut could clone it in 60 days.

Why now: macro-sharpening AI got cheap in 2024, and Etsy's algorithm is punishing low-clarity listings harder than ever.

Why us: honestly, weak fit. Nothing in the manufacturing/Apple/aviation/wine background pulls weight here. This is a pure cheap-probe bet, not an edge bet.

The path: $0 capital, $7 Gumroad guide, posted to r/EtsySellers and seller Facebook groups. Kill at 14 days if under 8 sales. Kill the SaaS pivot if survey conversion under 25%. Kill entirely if Pixelcut ships scale overlay first.

Give me 14 days and zero dollars. If it dies, it dies fast.

Problem
Etsy sellers struggle to photograph small products (tokens, miniatures) at scale—showing detail and text readability simultaneously is difficult, leading to lost sales from confused buyers.
Solution
Provide a simple photography template/guide kit (printable scale cards, lighting setup) or AI-assisted photo enhancement tool that auto-scales and clarifies small product text.
Target
~500K active Etsy sellers with physical products under 2 inches; those with <$5K annual revenue most price-sensitive.
First test
Create a $7 Gumroad guide (photography checklist + printable scale cards). Post in r/EtsySellers and Etsy forums. Target: 20+ purchases in 14 days.
Kill criteria
<8 purchases of the $7 guide within 14 days of first Reddit/forum post AND zero organic reshares or unsolicited community mentions → kill the guide angle; OR purchases hit 20 but <25% of buyers respond positively to a follow-up 'would you pay $9/mo for an AI version?' survey by day 30 → kill the SaaS pivot; OR Pixelcut/PhotoRoom announces scale-overlay feature before founder reaches $500 cumulative revenue → kill entirely
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bet_20260427_eaad79 · proposed
Nightly nudge for the chores you forget
2026-04-27 · reddit:AppIdeas:new
judge 75/100edge 1.5/10consumer app

Everyone has the same dumb problem: the trash, the lightbulb, the filter — small undated chores that don't deserve a calendar slot, so they rot in your todo app until you smell them. Todoist and Apple Reminders force you to pick a time you don't have, so you don't log them, and they get forgotten until they become a fight with your spouse.

The market is real but commodity: ~2M English-speaking productivity-app payers, $3-5/mo, so even a 1% capture is roughly $700K ARR. Not a unicorn — a cashflow app.

The wedge is one mechanic no mainstream app ships: dump tasks with zero metadata, get one batched push during a window you pick (say 7-8 PM). Users complain about exactly this gap on Asana, Todoist, and Due forums. It's narrow and honestly trivially copyable — Apple or Google could ship it in a point release. That's the real risk, not the build.

Why now is weak; I won't pretend. Push-notification fatigue is actually getting worse, which cuts both ways. No specific operator edge here either — this is a generic consumer play, not a Lisandro-shaped one.

The path is what makes this worth a yes: the Android APK exists. Cost to test is basically zero — push 30 beta users, watch 14-day notification opt-out and reminder-action logs. Kill if >60% disable pushes or fewer than 3 users act on 3+ reminders. Two weeks, no capital, clean signal.

Let me spend two weeks and 30 users proving the nightly window is a habit, not noise.

Problem
People struggle to remember to do small unscheduled household tasks (trash, cleaning) because existing todo apps require either firm deadlines (guesswork) or manual app checks, so tasks get forgotten entirely.
Solution
Task dump app with no due dates; users get reminders only during self-chosen windows (e.g., 7-8 PM daily) via push notification.
Target
Individual productivity users; est. 2M+ people struggling with task recall; TAM ~$50M at $3-5/mo SaaS freemium model.
First test
Deploy existing Android .apk prototype to 30 beta users; measure: DAU retention at 7d and 14d, and whether users log ≥3 reminders acted on in 14d.
Kill criteria
<25% of beta users have push notifications still enabled at day 14 AND <3 total users log ≥3 reminder-actions in 14d AND zero unprompted paid upgrade inquiries by day 30 → kill
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bet_20260427_5e3e13 · proposed
Etsy ad ROI minus all the fees
judge 75/100edge 1.5/10b2b saas

Etsy sellers are flying blind. They burn $50-200/mo on Promoted Listings, watch Etsy's dashboard report 'revenue,' then quietly pause campaigns because nobody — not Etsy, not Erank, not Marmalead — subtracts the 6.5% transaction fee, 3% payment processing, listing fees, and COGS to show actual profit. The r/EtsySellers thread is a graveyard of 'I think my ads work? I can't tell.'

The market is real but thin: ~100K active Etsy advertisers, $9-19 ARPU. At 2% capture and $14 ARPU, that's ~$340K ARR — a lifestyle ceiling, not a rocket. The wedge is sharp though: every competitor is SEO-first (keywords, tags, listing optimization). Nobody owns 'is this campaign actually profitable after Etsy takes its cuts?' with a one-click pause/scale signal.

Why now is also why maybe-not: Etsy reportedly has a native profitability column in beta. If they ship it in 60 days, we're dead. No operator edge here — this isn't Lisandro's manufacturing or ops world; it's a generic SaaS bet on a closing window.

The path is honest: 14 days, ~$0 capital, Google Sheet template + manual CSV import (Etsy OAuth review is 6-12 weeks, so we punt the auto-connector to v2). Post in r/EtsySellers, target 50 signups, 10 active users, 3 organic shares. Kill if traction misses OR Etsy ships native profitability in 90 days.

I'll be blunt: weak edge, real kill-switch risk, modest ceiling. But it's a $0 test of a clean wedge in 14 days. Let's run it cheap and see who shows up.

Problem
Etsy sellers running ads see profit erosion from Etsy's fee structure (ads + transaction fees + payment processing) making ROI unclear, so they pause campaigns without data to optimize.
Solution
Simple ad ROI calculator/dashboard that auto-imports Etsy ads spend and sales data, shows true profit per campaign, and recommends pause/scale decisions.
Target
~100K Etsy sellers actively running ads; pain threshold when ads consume >30% of margin.
First test
Build a Google Sheet template with embedded Etsy API read-only connector. Offer free access to 50 sellers via r/EtsySellers post. Target: 25+ signups, 10+ active users in 14 days.
Kill criteria
<5 of 50 invited users complete OAuth/data connection within 14 days AND <8 active users (defined as opening the dashboard 2+ times) by day 14 AND <3 users voluntarily sharing results or asking questions in the signup thread by day 21 AND $0 MRR by day 45 → kill; OR Etsy announces native profitability metrics in Ads dashboard at any point in 90 days → kill regardless of traction
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bet_20260427_ab09e6 · proposed · wildcard
★ Flat-fee chargeback defense for Shopify
2026-04-27 · wildcard:opus
judge 67/100edge 2.0/10

Shopify merchants doing $1M-$10M GMV bleed 0.6-1% of revenue to chargebacks and have nowhere to go: Chargeflow takes 25% of every recovery (which compounds painfully at $80+ AOVs), Justt won't return your call unless you're Fortune 500, and Stripe's native tools are DIY busywork. That's a real, ongoing tax on the exact merchants nobody serves well.

The math: ~40k mid-tier Shopify stores, 10-50 disputes/month, $15 flat = $1.8k-$18k ARPU. Even 1% capture at the low end is ~$700k ARR. Wedge is transparent flat pricing plus zero-touch self-serve — Chargeflow has 15-20k merchants but their pricing inverts above $60 AOV and onboarding still requires calls. Why now: Shopify and Stripe both opened dispute submission APIs in the last 18 months, making programmatic representment actually possible.

Honest about the risks. I have no operator edge here — this is a pure execution bet in a domain I don't know. Bigger problem: win rate. Visa reason codes need attested data Shopify's API doesn't fully expose, and if we land below 60% wins, the flat-fee math breaks for merchants. Chargeflow can also add a flat tier overnight.

The path is cheap: $400 in Reddit/Twitter ads, a Loom demo, manual API setup behind the curtain. Kill if <5 merchants submit a real dispute by day 30, <$150 collected by day 45, or win rate <25% before day 90.

$400 and 6 weeks to learn if the wedge is real. Let's find out.

Problem
Shopify merchants doing $1M-$10M GMV get hit with chargebacks but Chargeflow/Justt are priced for enterprise and require integration calls; small merchants eat 0.6-1% of revenue in chargebacks with no automated representment.
Solution
Self-serve chargeback representment tool that pulls Shopify order data via API, auto-generates Visa/Mastercard compliant evidence packets, and submits via Stripe/Shopify Payments dispute API — flat $15/dispute, no sales call.
Target
Shopify merchants $1M-$10M GMV (~40k stores per Shopify's public merchant counts); also WooCommerce/BigCommerce mid-tier. Pay $15-30 per dispute filed, ~10-50 disputes/month per merchant.
First test
Build a Shopify-app landing page + Loom demo showing the evidence packet generation on a fake dispute. Run $400 in Reddit ads (r/shopify, r/ecommerce) and 200 cold DMs to Shopify store owners on Twitter. Measure: install intents + paid pre-orders for first 10 disputes at $15 each.
Kill criteria
<5 merchants complete full API auth + submit at least 1 real dispute via the tool by day 30 AND <$150 in dispute fees collected by day 45 AND observed win rate on submitted disputes <25% at any point before day 90 → kill
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bet_20260427_218fea · proposed
Small electrical contractors switching from QuickBooks Desktop to Service Titan face 4+ hours/week of manual…
judge 52/100edge 1.5/10b2b saas
(No pitch — this bet pre-dates the pitch generator. Source data only.)
Problem
Small electrical contractors switching from QuickBooks Desktop to Service Titan face 4+ hours/week of manual workarounds (payables, timekeeping, return-trip logging) because integrations are broken or missing.
Solution
Build a lightweight Service Titan ↔ QuickBooks Desktop sync middleware that auto-maps timesheets, payables, and return-trip codes; charge $99-149/month per business.
Target
~2,000 small electrical/HVAC shops (5-15 techs) stuck between legacy QB and Service Titan; currently losing 3-5 hours/week to manual entry.
First test
Post in r/ServiceTitan and electrical contractor forums offering a 14-day free trial of a basic timesheet sync; measure: do 3+ shops complete trial and express willingness to pay.
Kill criteria
<3 trial signups within 14 days of first forum post AND <2 shops complete a full sync cycle during trial AND $0 MRR by Day 45 → kill; OR ServiceTitan API approval not granted within 30 days of application → pivot or kill; OR technical discovery confirms QB Desktop SDK requires Intuit partner tier costing >$500/mo → kill unit economics immediately
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bet_20260427_a4154d · proposed
Security teams perform annual pen tests with 3rd-party firms, missing continuous vulnerability detection and paying for…
2026-04-27 · hn:ask_hn
judge 50/100edge 1.5/10ai native
(No pitch — this bet pre-dates the pitch generator. Source data only.)
Problem
Security teams perform annual pen tests with 3rd-party firms, missing continuous vulnerability detection and paying for periodic, batched audits.
Solution
AI agent that continuously scans infrastructure for vulnerabilities and generates pen test reports on-demand, replacing annual cycles.
Target
Mid-market to enterprise security/DevOps teams (50k-500k employees); ~5k teams in US alone paying $15-50k/year for pen testing.
First test
Build a free tier that scans one public repo/API endpoint daily for 14 days, email weekly vulnerability summaries; measure signups and retention.
Kill criteria
<8 free-tier scans actually executed (not just signups) by day 14 AND <2 demo requests from verified security/DevOps leads with budget authority by day 30 AND 0 teams progressing to a paid or pilot conversation by day 60 → kill
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