PDX · Portland, Oregon & the Columbia River Gorge

Indie.
Durable.
Built to last.

I build travel companies, regenerative farms, AI agent systems and more. All independent, all built to last.

Since 1999: BootsnAll, AirTreks, and CarbonFarm. No outside capital, no growth-at-all-costs mentality. The mission underneath it all: helping people connect with themselves and the world.

Work with me Watch: “Is this it?” (8 min)

Sean Keener on the Oregon coast — Keener, Sean · Chicago-born · around the world since 1994

What I’m building now

2026 · current itinerary

TravelSince 2013

AirTreks

Complex multi-stop and round-the-world flights, planned by real experts. In January 2013 I co-launched the world’s first round-the-world flight search and ticketing engine, then acquired AirTreks that December and converted it from VC-backed to independent and profitable. Now we’re building the layer that lets travel advisors and AI assistants hand off complex trips to people who can actually ticket them.

1,000,000+ RTW and Complex trips planned and booked · partner & API program open

TravelSince 1999

BootsnAll

One of the web’s original indie travel communities, bootstrapped from day one. When I pitched it at an early investment conference, the audience assumed it was a non-profit. That was the point. More than 25 years on, it is one of the oldest continuously operating travel websites, with more than 2,000,000,000 visitors since 1999 who came to plan a big trip, gap year, or career break.

RTW Travel Guide since 2001 · Career breaks & gap years · zero outside capital, ever

LandFarming since 2005

CarbonFarm

1,462 acres of old wheat country in Dufur, Oregon, in conversion to regenerative agriculture since 2021: rotational grazing, virtual fencing, six years of restoration so far. I have been a regenerative farmer since 2005. The land is now for sale to the right steward, as a straight purchase or an operating partnership.

1,462 acres · Dufur, OR · listed at forsale.carbon.farm

AISince 2025

Agent-native tools

Small teams running big systems. I build autonomous agent networks that help humans do real work: research swarms, MCP servers, tools that other AI agents can discover and use. The thesis: in an AI-native world your audience isn’t just humans, it’s their agents too. AirTreks’ API-first booking layer is part of the same bet.

Agents assist & run daily marketing, finance, code judgement & research ops across my companies

Flight log

Selected waypoints

1994 BNE
A year at the University of Queensland in Brisbane. A Chicago kid discovers not everyone grew up on the Cubs, the Bulls, and his hometown assumptions. The seed of everything that followed.
1996 RTW
Quit a Chicago insurance job after asking “is this it?” in a Monday sales meeting. Spent 18 months going around the world on $6,000, overland from the UK to India.
1999 EUG
Co-founded BootsnAll in Eugene, Oregon, and lived on $500 a month for the first three years. Never raised a dollar of outside capital.
2002
First production of WorldCupBlog, perhaps the world’s first live blog.
2006
BootsnAll ranked the #1 travel site by Outside Magazine and named to the Times of London’s top 100 travel sites.
2006 GER
Produced WorldCupBlog.org on the ground in Germany for seven weeks of the World Cup.
2008
WorldCupBlog named one of the 50 most powerful blogs in the world by The Guardian.
2010
Saw the writing on the wall for media sites and started building Indie: the world’s first around-the-world automated ticketing engine.
2011
Sold WorldCupBlog and The Offside to SB Nation (Vox Media).
2013 SFO
Launched Indie, the world’s first round-the-world flight search and ticketing engine, in January. Acquired AirTreks in December and took it from VC-backed to indie, sustainable, and profitable.
2021 ORE
Co-founded CarbonFarm to convert 1,462 acres of Oregon wheat country to regenerative practices. A regenerative farmer myself since 2005.
2026 PDX
Building agent-native tools and the AI booking layer for complex travel. Chapter head of EO Ignitor Portland. Facilitating strategic planning for companies and nonprofits, as I have since 2002.

How I operate

Same rules since 1999

Durability over scale

Twenty-five years at a modest size beats five years of hockey-stick growth and a flameout.

Skeptical of outside capital

VC money comes with expectations that distort what a company is trying to be. Every business I run is bootstrapped or was converted back to it.

Community over extraction

Build things people trust and return to for decades, not funnels that maximize the one-time conversion.

Real voice, real opinions

Companies should sound like the people who run them. Nobody trusts a content mill, and they shouldn’t.

Work with me

Pick your route

Travel businesses & advisors

Your clients occasionally need a complex multi-stop or round-the-world trip and you don’t want to build that expertise in-house. AirTreks partners by referral, co-sell, or white-label API.

Talk partnerships

Buy or steward the farm

1,462 regenerative acres in Dufur, Oregon, owned free and clear. Open to a straight sale or an operating partnership with people who think in decades.

See the listing

Building with AI agents

If you’re running real businesses on autonomous agents, MCP servers, and small teams, I want to compare notes. I share what works and what breaks.

Compare notes

Founders & big-trip people

I coach early-stage founders through EO Ignitor Portland, facilitate strategic planning sessions, and will happily talk you into taking your career break or gap year.

Start a conversation

The fastest route is email. I read everything.

sean@keener.org

Portland, OR · Columbia River Gorge, WA Writing at this domain since 2003

Indie.Durable.Built to last.