The hitchhiker’s guide to fundraising.
Over last the 5 years, we’ve done 5 rounds of investment for Crew and then Unsplash.
Being based in Canada though, has meant a lot of travel to New York and the San Francisco Bay Area.
These travel costs can be significant, especially in the early stages of building your company.
For a lot of our fundraising rounds, we had to travel with little money. Over many trips, we came up with ways to travel to strike a balance between saving money, time, and stress. I wanted to share these ways here in case they might be useful for other traveling founders.
- Bring only a backpack. Bringing only a single thing to carry all your stuff makes you flexible. When we’re fundraising, we don’t book return tickets. We book our next ticket based on what’s happening in our meetings. Sometimes this means ping-ponging between Boston, New York, and San Francisco. If you’re doing this with just a backpack, it feels like no big deal. The extra stress of a luggage is not worth it. Waiting for it at airports. Walking around busy streets, smashing it into curbs and potholes. Having to keep track of more things. Not allowing you take a bike if you want. Not worth it. The best travel backpack I found is from Lululemon. I still use the same one I bought 4 years ago. It’s $150. It’s built well for your posture. The size is big enough to cover multi-week trips. But it’s not too big where it destroys your shoulders or is awkward to fit under an airplane seat. They don’t make the model I have anymore but they have other similar ones.
2. Pack neutral color clothes. You can lose a lot of mental and physical space trying to match outfits. I’d rather put more of my mental energy toward closing financing versus deciding what to wear. Better that everything goes with everything. This is probably the only way you’ll fit everything in one backpack any way.
3. Book all your meetings 3 weeks before you leave. Schedule them over 2–3 days. The biggest travel costs are flights and places to stay. Lining up everyone you want to meet over a few days will help control these costs. Scheduling meetings 3 weeks before you travel is the best time to get openings on the calendar but not too far away where no one’s thinking about that week yet.
4. Walking/biking is cheaper (and often faster) than Uber. Bonus: It feels better too. San Francisco, New York, and Boston all have public bike systems. When the stress of a funding round is happening, I’d rather be outside than crammed in a car sitting in traffic. You can see where all the bike locations in these cities are with this one app.
5. Drive if you have to. On a few of our investment rounds, we didn’t have the money for plane tickets. So we’d borrow a car and drive to Boston or New York from Montreal.
We still drive sometimes. A road trip doesn’t have to be a drag. We’ve turned some into family trips.
6. Bus (but only as a last resort). We’ve done the Montreal to New York/Boston bus trip multiple times. (Our first bus trip we met the first US investor to write us a check.) It’s cheaper than flying and driving, but it’s unpleasant. Multiple stops make the trip long. About 10 hours. The seats are uncomfortable. One time our bus driver left the bus at a stop and his replacement never showed up. We were stuck for an extra 5 hours. The bus is not ideal but sometimes you can’t afford ideal.
7. Take the train between Boston and New York instead of flying. It’s more comfortable. The Wi-Fi is pretty good. It costs nearly the same and gets you into downtown New York in roughly the same amount of time.
8. Share a room. Sharing a room for a long period of time may not be ideal for your psyche but if you’re tight on money, it’s one of the biggest ways to save. Another option is stay at a friend’s place. Some of our friends have let us crash for multiple nights. Thank you Daniel Burka. Thank you Accomplice. If you’re heading to New York, one hidden gem we’ve found is the Wyndham hotel. It’s no Ritz Carlton but it sits just outside of Soho so it qualifies as Chinatown so it’s much cheaper. Rooms are bigger and nicer than what you typically can get in New York. The location is within walking distance of most people you’d be meeting.
9. Work from cafes or your hotel room. Paying for the hotel Wi-Fi is often cheaper and more efficient than trying to find cafes with good Wi-Fi, plugs, a bathroom, and enough open seats. But if you’re out in the city, the “coffeeshops with wifi” Foursquare filter is how we find places to work from. Sometimes we choose a place that has food and coffee so we don’t have to move when we want to eat. If you need multiple seats, one of the most dependable spots in New York is Project Cozy, a 7-minute walk from the Wyndham hotel mentioned above. There’s a Sweetgreen around the corner. The first time I went to San Francisco, I was surprised by the lack of cafes with good Wi-Fi. I thought it‘d’ be a requirement that every cafe had great Wi-Fi in the tech capital of the world. But I get it. Tech can get overwhelming if it’s everywhere. The most dependable spots in San Francisco are Philz and Starbucks.
10. Eat healthy without spending a lot. We go for acai bowls for breakfast (NY map; SF map). Sweetgreen salads for lunch (NY map; SF map). Not too expensive relative to other options and consistent quality. Another option we love in New York is by CHLOE. Plant-based fast food located through out the city. Otherwise, we use this Foursquare filter to find cheap, healthy food (NY map; SF map).
11. Workout at the YMCA or public parks. Most YMCA’s have a free day pass or their day passes will likely be the cheapest of any gym in New York or San Francisco. Otherwise, you can use this search for parks that have free workout areas (Free outdoor work out parks: NY map, SF map).
12. Book a Recharge if you’re doing the overnight flight from SF to NY. Recharge allows you to book 4 and 5-star hotels by the hour. It’s an easy way to get a few hours of sleep and shower before your first meeting.
13. Fly into Newark instead of LaGuardia or JFK in New York. Newark is less crazy of an airport and traffic to get into Manhattan is often better.
14. Get a US phone plan. You might not need to worry about this if you’re based in the US. But if you’re based in Canada, you can get unlimited U.S. calling and texting for $10. Before they offered this phone plan we used to just operate on Wi-Fi in the US. We’d take pictures of maps for directions. We’d take calls in Wi-Fi zones. Not the most optimal but it gets the job done if your US phone options aren’t great.
15. Get a Nexus/Global Entry pass. For a one-time $50 fee, you skip airport lines between the US and Canada for 5 years. Global Entry allows you to skip lines in the US for a one-time $100 fee. Here’s where you can see if you’re eligible to apply for a Global Entry pass.
With the exception of taking a bus, we still do all of these things when we travel for Unsplash. We’ve found a system that hits the sweet spot. We feel good when we travel and we don’t feel we’re overpaying for luxuries that don’t provide that much benefit.
You don’t have to be based in New York or the Bay Area to raise money or build a company. But you might have to travel there. They’re still hubs where many of your partners or people might be. Hopefully, some of these ideas can help you get and stay there with peace of mind, without breaking the bank.
And while you’re at it, enjoy your trip. It’s fortunate we work in an industry that can bring us to a couple of the greatest cities in the world.