Just as Hollywood is where people go to become famous actors, Silicon Valley is where founders go to build famous companies. My first time in San Francisco was in November of 2014; I bought a one-way ticket and ended up spending nearly three weeks meeting amazing people and soaking in the culture. I’ve visited three more times since and spent over six months in the Valley building what we think is the next great HRTech company.

I’ve received a significant number of inquiries on where to stay, where to go, and who to meet from startup founders embarking on a similar journey. So I decided to share the steps I took to find accommodations, get around, and create meaningful connections during my first trip to the Valley.

Before I get to that, however, I want to preface my guide with additional words of advice:

First and foremost, San Francisco is expensive no matter what sacrifices you make in terms of personal comfort, so if you’re a startup founder and you’re spending time and money on a Valley trip make sure you have a game plan. Keep your goals simple — connect with other founders, meet potential advisors, and pitch your business for feedback. I can’t count how many times I’ve had people tell me they are headed to the Valley to raise money with no real connections or validation on their idea yet. There is a myth that it’s easier to raise money in the Valley, and perhaps there is some truth to that, but it’s unlikely to happen on your first visit.

Also, prepare in advance — I don’t mean days, I mean weeks. If you want intros to people don’t reach out a few days before taking off. This is a common mistake, and while it is time-consuming to identify who you would like to meet with and who can introduce you to them it’s a necessary effort.

Finally, let people know! Sharing the fact that you will be in San Francisco (or anywhere) on specific dates on social media may prompt people to reach out and connect with you. It worked for me on both of my icebreaker trips to San Francisco and New York City.

With these notes out of the way here are some resources to help you plan. This advice may seem focused on Canadian founders, but most of it applies to any first-timer:


Longer stays (1 week+): Google “startup houses Airbnb San Francisco” which actually delivers good results (at least in my experience) versus going directly to Airbnb’s website. Startup houses are typically comprised of other founders who are in SF to make it big. It’s a great way to meet people who have similar aspirations and you will likely make lasting connections from it.

Short stays (Less than a week): Look for shared accommodations, even if it’s not a startup house. There is a good chance the people living there are in one way or another involved in a startup or established tech company.

Other options: VRBO works as well, or you can try searching SF Housing Groups on Facebook. If all else fails, Hotel Tonight is a great option for last-minute deals though please note that it only works as an app on your phone.

If you’re a little skittish on your first visit you may wish to avoid staying around the Tenderloin area or in and around 6th to 10th Mission St. While I have never encountered any issues in those areas, they may not give you the most favorable first-impression of San Francisco.


BART: Bay Area Rapid Transit, it’s the city’s official subway system. It is actually pretty decent and can get you close to most destinations that matter.

Bike Rentals: There are lots of locations around and it’s a great way to see the city. San Francisco has clearly designated bike paths making it very safe for bikers.

Lyft/Uber: If you’re from a small region like I am you may wonder how you’ll live without these services once you get back home. Install them on your phone and see why they are disrupting the taxi industry. Links: Lyft – Uber

MUNI: San Francisco’s bus transportation system. I didn’t use it, but I hear it’s just fine.

Getaround.com: Yes it’s another app, and it’s by far the best option I found for car rentals. It lets you rent other people’s cars starting at $5/hr (I even rented a Tesla S85 for $20/hr). There are typically plenty of options available within whichever area you are in at any time. They charge a $1 admin fee, insurance is included, and it’s a thousand times more convenient than conventional rental car companies. NOTE: Depending on where you live you may need to send them your driving records prior to your visit so they can setup your account. It’s not ideal — but it’s definitely worth it.


Other than getting introduced to specific individuals, here are other things you can do to connect with people:

Industry Events: Checkout sites like meetup.com or eventbrite.com to find networking events. There is almost always something going on and they’re a great way to meet new people. During my first visit I attended an amazing workshop on habit-forming products with Nir Eyal at Yelp HQ and they even gave me a “minute-at-the-mic” to pitch our business in front of over 200 people.

Work in Coffee Shops: It may not seem like the most productive thing to do, but soaking in the culture is just as good as meeting people. This is part of understanding what makes SF unique, and when you find yourself at a local coffee shop surrounded by people with incredible drive you can’t help but absorb it and feed off that energy.

Visit Co-Working Spaces: Galvanize is a great spot, but there are other options — just Google them. See if you can get connected to a member or gain temporary access. It’s a great opportunity to meet other founders and get insights from them.

Join Facebook Groups: There are Facebook groups like “Canadians in the Valley” and “Canadians in NYC”, request to join them and let them know your intent, it’s likely someone will offer to give you the lowdown. I met Amanda Parker in a Facebook group and she graciously introduced me to 500 Startups. Fun Fact: Did you know there are over 300,000 Canadians (1% of Canada’s population) living in the Valley?

Connect with C100: They are there to help. They get inundated with requests, however, so make sure you give them plenty of heads-up time, and be specific as to who you would like face time with. They also have monthly events that you can attend if it happens to align with your visiting dates.

San Francisco is a unique place, you won’t see a lot of suits and ties and likely won’t get a meeting before 9 am —actually make that 10 am. It’s a city where over 80% of the people living there are not from there, so it’s fairly easy to strike a conversation with someone you don’t know; they were probably in your shoes at one point or another.

Those are just things I did on my first visit and it worked out great for me, hopefully it will for you too.

Learn more about Alongside , Yves Boudreau’s New Brunswick-based startup at Alongside.com.

Cover image via Wikimedia Commons