The two questions founders ask us most on AskTechTO are how to raise from US VCs and whether to move to San Francisco. Both point at a map.

Earlier this spring we had four founders from the three-week Game On program in San Francisco and then four investors who write cheques on both sides of the border. Nobody answered either one with a city.

Here's the split.

Fortress Canada. Pascal Dessureault (Co-Founder, Tablevoice) named it, and it's the cleanest description I've heard of something I see constantly. Win Canada first, then go south once you feel ready. It sounds like discipline. What it does is hide a sales problem behind a slow pipeline. Chris Neumann put the cause under it: we protect a lot of our businesses here, so Canadian buyers don't feel under existential threat. They take the meeting, then take another one. That's not a slower market. It's a safer one, and safety shows up in your funnel as meeting number 12.

The acquirer slide. TX Zhuo of Fika Ventures spotted this one, and he sees decks from both countries. Canadian decks carry a slide listing potential acquirers, which tells him the founder is already picturing an exit inside a range. American decks say they're going to be number one in the category, and if that means buying Salesforce, fine. One asks who might buy you. The other assumes you're the buyer. Another investor on the panel said the ecosystem self-inflicts it, because the doctors and dentists on a Canadian cap table want to hear about exits.

The $5M USD finish line. Founders keep telling me $5M USD in revenue is the win. It's the starting line. If you can't say where the company goes after it, that number is a ceiling you set yourself, and every investor reading it knows.

The ask at the end of the meeting. Nima Jalalvandi (CEO and Co-founder, Ready Plan Go) flew down to SF planning to meet a hundred VCs. Chris sent him after customers instead, so he changed one line. He stopped asking for an intro to an investor and started asking for an intro to an accounting firm. He went from one client in Pennsylvania to 4x the revenue. Investor intros are easy to give and worth almost nothing. Customer intros cost the other person something, which is why they count.

It's not where you live. It's where your buyer lives. Pascal spent four months and twelve meetings on a group of Toronto restaurants and still had no signature. He ran the same demo in the US and got yeses on the spot, then 3x'd across four American cities. Same product, same pitch, same kind of customer. What changed was a buyer who feels the clock.

That is a border effect, and it's worth being precise about which side of the transaction it sits on. Your address isn't the variable. Your customer's market is. Time both cycles, then ask every prospect what breaks if they do nothing for six months.

Ambition, said out loud. Own the wedge that gets you to $10M USD, then say plainly it's your step to $100M USD. Most founders think it and are too embarrassed to write it down. Your American competitor has done nothing and is promising twenty times the revenue inside a year. Over-learn to over-promise, then over-deliver.

Pitch the Americans first, even if you plan to raise here. Isaac Souweine keeps getting handed a spreadsheet of twenty firms, every one the most obvious name on the front page of TechCrunch. Expand the list. Then his actual tactic: pitch all the Americans, and tell the Canadians you're pitching them. Nobody wants to lose a deal to a US fund. He also thinks you can usually hold a slice of the round back for the smaller investors who will do the work.

Speed is a design choice, not a personality. Jason Gray of Pioneer Fund decides in 48 hours. He can do that because he front-loads the diligence before the call, and he built the fund that way because raising capital as a founder in Canada was, in his words, one of the worst experiences of his life. Andre Charoo has gone from twelve hours to two years on the same decision. So ask a fund how it actually decides, and who has to say yes. That answer tells you more than the brand does.

Not all money is the same money. Andre's framing is that some capital carries advantage and some is only fast. A Valley cheque can mean you're one of a hundred, with nobody checking in until IPO prep. The smaller local investor is often the one who works. One of the four said out loud that 90% of venture capitalists destroy value. The test another gave: could you sit through a two-hour dinner with this investor and not want to leave.

Only one of the nine things above turns on a postcode, and it isn't yours. It's your buyer's. Three weeks in San Francisco bought those founders a faster customer and a better ask. It didn't buy them an address, and not one of them moved. One is in Vancouver, one commutes from Montreal, one is a digital nomad.

Isaac put the bar where it actually sits. “Power law means power law. It used to mean a billion-dollar company. It now effectively means a ten-billion-dollar one.” His framing was an Olympic one. “You're not trying to win the local swim race. You're trying to be the gold medalist.”

If that sounds like too much, know that it's the bar every fund is holding you to. Most of them won't say it in the meeting.

Dive deeper on our YouTube channel: four founders on what actually changed, then four investors on who they'd back.

Selling and fundraising across the border is the conversation at every Together Toronto. The next one is Monday, September 14.

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