Kyle

I build things.

Australian founder, dual Austrian citizen. Started a company at 19 and ran it for seven years to $2-3M revenue, then taught myself to ship product through AI. Now building Upway, the agentic operating system for travel, while operating fractionally across three other companies. Between Austin and London.

Founder Operator Pilot (RPL) EU + AUS citizen Austin / London

What I've built

Companies I've started, run, or operated end-to-end. Click any one to read more.

Upway Current

The agentic operating system for travel. One chat to plan, book, redeem, and manage your trips on your behalf.

2024 -

Four verbs, one chat: plan trips, book flights and stays, redeem idle credit-card points for 3-8× more value, and manage the whole thing autonomously. Built around the bet that the chat itself becomes the operating system. Not a dashboard, not a search bar.

  • Solo full-stack build on Anthropic's Claude API: Next.js + TypeScript, Node.js, PostgreSQL with pgvector, 21+ custom tools running in an agentic loop, model routing across Haiku, Sonnet, and Opus.
  • Transfer intelligence engine: 18 loyalty programs, 100+ airlines, real-time bonus tracking, multi-path optimisation. Integrations with Duffel, Seats.aero, ElevenLabs, Stripe.
  • In active conversations with YC, Antler, Startmate, Airtree, SideStage. Adviser network includes Simon Lehmann (ex-CEO Phocuswright).
  • Co-founder: Harry Fiske Kealy (brand & creative). Extended team across editorial, design, and engineering.
Consolia Acquired

AI property management for individual short-term rental hosts. Sister company to Cosmo. Sold to a Singapore-based PropTech operator in April 2026.

2025 - 2026

Founded mid-2025 as a sister company to Cosmo. Took seven years of operating playbook and turned it into an AI-native product for individual property owners, replacing the traditional property-manager role with software.

  • Built solo on Claude's API: chat-driven host operations covering pricing, guest experience, reviews, compliance, and listing optimisation.
  • Positioned as the premium operating layer for self-managed owners with 1-2 properties.
  • Led product, GTM, and capital raise. Acquired by a Singapore-based PropTech operator in April 2026 after ~10 months of operation.
Cosmo

Founded at 19. Built and ran a short-term rental management company across Australia for nearly seven years. Team of 10. Learned everything the hard way.

2019 - 2025

Bootstrapped from $0 to $2-3M annual revenue, 100+ properties under management, and a team of 10 across operations, cleaning, sales, customer service, and tech. Zero outside capital, multi-state ops, survived COVID.

  • Owned every function: hiring, P&L, pricing, sales, product, finance, legal, supplier negotiation, regulatory work.
  • Built the SOP library that scaled the business without proportional headcount growth.
  • In 2025, led the company through a voluntary administration resulting in a clean, legally compliant close-out via Deed of Company Arrangement (DOCA). Protected stakeholders and preserved operating IP.
  • The full-cycle founder experience: scaling, surviving, restructuring, and rebuilding under one continuous mandate.

Also operating

Concurrent consulting and operating gigs. Sales, product, and revenue work for other founders.

NR Medical Fractional CRO

Turning around a US healthcare org's sales motion. HubSpot, AI calling, coaching, conversion rebuild.

2025 -

Hired to fix a stalling sales organisation that was running on spreadsheets and disconnected tools. Owning the playbook end-to-end. Technology, process, people.

  • Implemented HubSpot as CRM and sales operating system. Migrated lead history, built sequences, templates, and reporting dashboards.
  • Rebuilt the cold-calling motion: new scripts, segmentation, deal stages, call-coaching frameworks.
  • Deployed Aircall + AI-powered calling agents to scale outbound and qualify leads faster.
  • Coach and manage the team day-to-day. Consistently exceeding monthly conversion and revenue targets under the new playbook.
SPV Product & Eng

Building Superfund Property Valuations' customer platform from scratch. Replacing legacy Salesforce with a full-stack SMSF valuation product.

2025 -

Sole technical lead on the rebuild, replacing legacy Salesforce + manual workflows with a custom platform designed around how SPV actually serves customers.

  • Customer-facing frontend where clients request, view, and manage SMSF-compliant property valuation reports.
  • Backend schema, API layer, and admin dashboard. Custom CRM and reporting layer replacing Salesforce entirely.
  • Scope spans both the engineering build and the operational redesign of how SPV serves customers.
2AC Urban Stays  ·  PriceLabs Revenue

Senior consultant to PriceLabs (dynamic pricing SaaS) with direct portfolio work for 2AC Urban Stays in Vienna.

2025 -

Two-sided engagement: advising the leading dynamic-pricing platform for short-term rentals, and operating hands-on for one of their flagship clients.

  • PriceLabs: advise on host strategy, audit pricing methodology, and build instructional content for the user base.
  • 2AC Urban Stays (Vienna): repriced the portfolio, optimised listings, and lifted RevPAR through direct operator work.

Building Upway toward a seed raise. Splitting time between Austin and London. Thinking a lot about how AI changes what it takes to build companies. The people, the toolkit, the cycle time. Previously on the boards of the Australian Short-Term Rental Association and Bendigo Health Foundation. I have a pilot's licence, which has nothing to do with anything but I like mentioning it.