ittlebid
MarketplaceLightweight bidding for local deals and services.
Software Investments & Strategic Ventures
Tennessee‑based holding company building durable, AI‑forward products and real‑world businesses for long‑term impact.
Our Core Focus
A simple, durable thesis: craft great software, partner with resilient operators, and compound over decades.
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Proprietary Software
AI‑assisted platforms that automate operational drudgery for specialized industries.
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Diversified Holdings
Balanced exposure across software, services, and niche real assets for resilience.
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Long‑Term Orientation
We favor compounding, relationships, and craftsmanship over growth at all costs.
We build AI Apps for use with ChatGPT
Custom, domain‑specific AI apps that run inside ChatGPT—grounded in your data and workflows. Perfect for support, ops, compliance, and internal tools.
Selected Software
A snapshot of platforms we operate or are actively building.
I Hate Meal Planning
ConsumerAutomated weekly meal plans with smart grocery lists and SMS nudges.
SugarShackCRM
CRMClean, fast CRM + inbox for small teams—keep deals and comms in one place.
LettersAI
AIAI‑generated letters, forms, and polished documents—one‑click export.
BrewComply
ComplianceAutomated TTB filings and risk alerts for independent craft breweries.
BlueBlast
macOSReal iMessage campaigns at scale from your Mac—no SMS gateway needed.
BarrelLive
EventsLive arena broadcasting for barrel races—times, payouts, and sponsors instantly on phones.
Bates Stamper Pro
LegalSecure, offline-first PDF bates stamping for macOS. Stamp thousands of pages in seconds.
MidSouth CTO
ServicesFractional CTO services for growing businesses—automation, systems, and strategy.
Valve
AutoAI-powered shop management: digital estimates, invoices, and CRM for auto repair.
Let’s build something durable
We partner with founders and operators who value craftsmanship and compounding over hype.
HQMemphis, Tennessee