Building a Startup (and a Life) in Chile on a Remote Schedule

When I landed in Santiago on a gray winter morning, I could see a crisp line of white on the horizon where the Andes cut into the sky. I had a backpack, two suitcases, a remote marketing contract to keep the lights on, and an acceptance letter from Start-Up Chile that felt equal parts golden ticket and dare. I didn’t know yet that I’d learn to sleep through tremors, that “cachai?” would slip into my sentences, or that my toes would stay perpetually cold in an apartment with tile floors and no central heating. But I also didn’t know how much the mountains would anchor me, and how the rhythm of a city in winter could be so alive.

Why Chile (and Why in Winter)

I applied to Start-Up Chile from my tiny Brooklyn apartment in late spring, pitching a tool that helps small e-commerce brands manage multilingual content. The program’s reputation—equity-free funding, mentorship, and a gateway into Latin America—was the draw. I was honest in the application about still taking remote gigs to support myself, and it turned out I wasn’t alone in straddling “founder” and “freelancer.”

When the acceptance email arrived, I did a little kitchen dance, then immediately panicked about visas. The program provided a support letter for temporary residence (requirements change, so always double-check the official migration site), but I still had to gather a criminal background check with an apostille, proof of funds, and a small library of PDFs to upload. Processing took a while—government seasons move at their own pace—so I entered as a tourist and waited for approval. When the electronic stamp finally came through, I registered, got my cédula (national ID), and then my RUT (the number that unlocks everything from phone plans to bank accounts). I cried in the Registro Civil bathroom after the ID photo because I was equal parts relieved and exhausted.

If you’re considering it: start the paperwork early, scan everything, and keep copies in a cloud folder and a USB. Also, bring a few extra passport photos. You’ll thank me later.

Finding a Home Base

I bounced between Airbnbs my first two weeks, comparing neighborhoods between metro stops. Providencia felt walkable and leafy, Ñuñoa had lively plazas and dogs in sweaters, and Las Condes was polished but pricier. I ended up in Ñuñoa, in a small one-bedroom with a balcony that faces a bakery. Every morning, the smell of marraqueta pulls me out of bed.

Practicalities: landlords often want an “aval” (a local co-signer), which most newcomers don’t have. I found my place by being upfront about my situation and offering a larger deposit plus references. Expect to pay “gastos comunes” (building fees) on top of rent, and ask what they include. My rent is mid-range for the area, and gastos comunes swing between modest in summer and higher in winter with increased building heating and maintenance. If your windows are single-pane (likely), budget for a space heater and heavy socks. Insulation isn’t a given.

For search, I used local sites, walked the neighborhoods, and checked Facebook groups. You’ll see unfurnished and furnished listings; “semi-amoblado” sometimes means a fridge and a stove—and not much else.

Work, Start-Up Chile, and the Two-Calendar Life

My weekdays toggle between my remote clients (mostly on U.S. East Coast time) and Start-Up Chile activities. The program’s workshops, office hours, and founder meetups happen mostly during the day, so I build my client calls after lunch. It makes for long afternoons, but the coffee here helps. I work out of a coworking space in Providencia with floor-to-ceiling windows and a view that, on clear days after rain, lines Santiago up neatly against the mountains like a postcard.

Start-Up Chile has been especially helpful with soft-landing: legal talks on forming a company, introductions to other founders, and a Slack where someone always knows a good accountant or fixer. I had to incorporate a Chilean entity to receive program funds and was guided through the basics—bank accounts require patience and a RUT, and yes, signatures multiply here. The bureaucracy is real, but not insurmountable if you show up with documents and snacks.

Tip: book bureaucratic appointments early, and always bring a pen. Also, don’t schedule anything important on the same day you’re waiting on government offices. Your sanity will thank you.

Day-to-Day Life: Winter Routine

Winter here is a mood: low clouds, occasional rain that turns the city streets reflective, and crisp mornings that make your breath visible. On those rare post-storm days, the smog lifts and the mountains glimmer. I’ve started timing my lunch walks for those moments. The metro is clean and reliable; I got a bip! card my first week and learned to plan routes that include transfers within the integrated fare window. It’s rare I need a car, though I’ll ride-share at night when I’m carrying a laptop.

Food-wise, winter means soup. I’ve fallen for cazuela (chicken broth with pumpkin and corn) and sopapillas pasadas on rainy nights, swimming in a sweet cinnamon sauce I didn’t know I needed. At La Vega Central, I learned that a “kilo” of avocados is more than I can responsibly consume alone, and that the vendors will call me “mi niña” even though I’m 29 and wear a puffer jacket like armor.

The first time I felt an earthquake—just a trembling sway—I froze and then watched as everyone around me barely looked up from their phones. A barista told me it was “suavecito, no te preocupes,” and handed me a second espresso on the house. It was oddly grounding.

Community: Finding My People

I met my first friends at a Start-Up Chile orientation where we bonded over Spanish verbs and tax forms. We started a Thursday “once” tradition—a Chilean tea-time that’s basically dinner with bread, cheese, palta (avocado), and conversation. Someone always brings a bottle of carménère. Through meetups, coworking kitchens, and a language exchange in Bellavista, my circle widened to include Chileans and expats from Brazil, Spain, and Australia. There’s a frankness here I appreciate—people will tell you if your business model is weak and then send three contacts to help you fix it.

For connection: the Start-Up Chile alumni network is gold. So are Slack groups and WhatsApp chats that materialize out of nowhere. I’ve had more serendipitous coffees because someone “knows a woman you should meet” than in any other city.

Learning Spanish (and Unlearning Ego)

I arrived with a decent grasp of Spanish that promptly melted in the face of Chilean Spanish. It’s fast, full of chilenismos, and peppered with “po” (yes, po; no, po) and “cachai?” (you know?). The first time someone asked if I “pololeo,” I nodded, assuming they meant polo. They meant: are you dating. I am not. I now say “al tiro” (right away) more than I should.

What helped: a local tutor twice a week, a grammar app for drills, and asking friends to correct me in real time. I keep a notes app of new words: fome (boring), bacán (cool), pega (job), and luca (a thousand pesos). The day the produce vendor at my feria told me my Spanish had improved, I glowed all the way home.

Health and Practical Stuff

I started with international health insurance for the first couple months, then switched to a local private plan once I had my cédula and more predictable residence status. Chile has both public (FONASA) and private (ISAPRE) systems; clinics are modern, and telemedicine is easy to access. Dental care is straightforward and affordable by U.S. standards—I chipped a tooth on a hard piece of pan amasado and got it handled same week.

Safety-wise, it’s a mixed bag. I don’t flash my phone on the street, and I use a crossbody bag. Petty theft happens; common sense helps. I generally feel safe walking in my neighborhood before 9 pm, but I don’t push it late. The police presence increases during “preemergencias ambientales” when air quality dips and vehicle restrictions kick in—winter realities that locals take in stride.

Money: once I had my RUT, opening a basic account became easier, and paying bills online (electricity, water, gastos comunes) is routine. I still invoice U.S. clients in dollars and convert as needed; fees vary, so shop around for the cheapest route. If you’re thinking about taxes, talk to a professional. Chile’s rules around foreign-sourced income and residency are specific and change; don’t guess.

The Andes in My Weekends

One hour from my desk is a world of snow. Friends piled me into a car before dawn and drove the hairpin road up to Valle Nevado for my first winter Saturday in real mountains. I rented gear, fell twice, and then glided exactly once in a way that made me forget I had Slack messages waiting. On another weekend, we soaked in hot springs out in Cajón del Maipo while snow drifted in lazy flakes and a stray dog guarded our backpacks.

Those escapes reset me. On clear Sundays I hike Cerro San Cristóbal, watch the city breathe below, and remember why I chose a life with horizons that include high peaks and new verbs.

Costs, in Real Terms

Numbers swing with inflation and neighborhoods, but this is what my life looks like:

• Rent for a one-bedroom in Ñuñoa: mid-range for Santiago, plus monthly building fees.
• Utilities: higher in winter with heating; summer is kinder.
• Metro/bus: each ride under the equivalent of a U.S. dollar, with transfers included within a window.
• Groceries: cheaper at ferias and La Vega; markets are an experience as much as a budget strategy.
• Eating out: affordable lunches (“menú del día”) are a habit; weekend dinners add up, as anywhere.

Santiago isn’t cheap, but it’s kinder to my budget than New York, and the quality of life—the parks, the mountains, the ease of getting around—makes the trade-off feel fair.

What I’ve Learned (and What I’d Tell You)

• Start early on the visa. If you’re coming via Start-Up Chile, use their guidance, but verify everything on official sites. Rules change.
• Get a tutor your first week. Chilean Spanish is a different game, and learning local phrases is both respectful and useful.
• Choose housing for winter: sunlight, insulation, and a plan for heating matter more than you think.
• Pack documents, then pack patience. Bring backup power banks and snacks to appointments.
• Say yes to “once,” to founder coffees, to a spontaneous ski day. Your network grows at the edges of your comfort zone.
• Protect your time. The remote-plus-startup juggle is real; block focus hours and stick to them.
• Make friends with your barrio: the bakery guy, the produce vendor, the woman who sells sopaipillas on rainy afternoons. They become your anchors.

On cold nights, I sit on my balcony in a sweater and watch the city settle, a thousand windows blinking on like fireflies. I’m not sure where my startup will be in a year, or if I’ll still be in this exact apartment with the draft that sneaks in under the door. But I know this: I’m building something here—company, community, language—layer by layer, the way you dress for winter. And when the clouds crack and the Andes appear, I feel a little bit brave.

Best wishes from Santiago,