The Only Obstacle Is Ourselves
How Rob Khazzam built Float by betting on Canada
Today’s read makes me especially happy, because it’s proof that Not Sorry is working.
A couple months ago, Ben Clayton reached out asking how he could help make Canada the place he wants to build. We planned to connect, but before we ever spoke, he sent me this note:
“I contacted the CEO of Float, had a call with him yesterday and am working on an article.”
That’s Not Sorry in action. Ben saw what he wanted to build, did the research, and made it happen.
I’m thrilled to run his piece on Rob Khazzam, who built Float, a Toronto fintech now serving 6,000+ Canadian businesses, the exact same way.
Onto winning.
By Ben Clayton
I am the biggest obstacle to creating the next great Canadian success story. So are you.
I believed that building something great meant eventually moving to the United States. Bigger market, more capital, more talent density. That’s just what serious entrepreneurs do.
Then I spoke with Rob Khazzam.
Rob is the co-founder and CEO of Float, a company aspiring to build Canada's most intelligent business finance platform. He taught me three things that changed how I see entrepreneurship in Canada:
The longer you wait, the harder it becomes
Ideas mean nothing; execution is everything
Canada is the right place, right now
Let me explain.
The longer you wait, the harder it becomes
Rob took the “safe” path. Western Ivey undergrad, then Private Equity on Bay Street, Canada’s equivalent of Wall Street. By conventional metrics, he was successful.
“For the last two years of my time in Private Equity, I was unhappy and unsatisfied,” Rob told me.
Leaving felt impossible. Startups sound attractive until you’re facing a pay cut, an unclear path forward, and questions from family about why you’d walk away from such a “great career.” For Canadians, the US often offers higher salaries and a favourable exchange rate. When it’s that easy to make more money south of the border, why take the risk to build something here?
“I felt a cultural aversion to risk-taking, to being aggressive, being ambitious,” Rob said.
That version of Rob is gone. When I speak with him today, his demeanour is battle-ready like a modern-day gladiator preparing for combat, except his battle is against outdated bookkeeping. And unlike a gladiator, he had just put his kid down for a nap.
The evolution from risk-averse professional to founder didn’t happen overnight. After five years in Private Equity, Rob realized the risk he’d worried about was largely imaginary. A mentor asked him one question: “What’s the worst that could happen? You find another job?”
Turns out, he did just that.
Rob joined Uber in 2014, back when the company was still fighting regulatory battles, like operation SLOG, around the world. He joined their International Launch team and spent time in Eastern Europe, helping expand from 66 cities at the start of 2014 to 266 by year’s end.
“I found the ownership intoxicating,” he said.
Over five years, Rob learned what building at scale looked like. By the end of his tenure, he was managing a $1B profit and loss statement in Canada. He’d settled into another comfortable role, itching to scratch that entrepreneurial itch yet again. And his mentor’s question rang through his brain once again: what’s the worst that could happen?
In late 2020 and early 2021, he began exploring ideas to build something more ambitious for Canada. Through extensive networking, he met Griffin Keglevich and Ruslan Nikolaev, then computer science students at the University of Waterloo, who had already been building together and experimenting with early ideas around modernizing business finance. They had encountered the same frustrating problem while interning at Shopify and Uber: the dreaded employee expense report.
Rob recalls, “I didn’t know what to expect when I met them. Our first meeting was meant to be an hour and ended up running more than three.” The three quickly bonded over a shared belief that business finance was far too complicated, and that embedding payments and financial services directly into software could deliver 10x better experiences for Canadian companies.
“I was blown away by how sharp and determined they were,” Rob said. “I went home and told my then girlfriend, now wife: this is it. This is the problem space and team I’ve been looking for.”
Shortly thereafter, in the spring of 2021, Float was born.
If Rob could change one thing, he would have started sooner. By the time you’re approaching thirty, many people have mortgages, obligations. The golden handcuffs of a stable career start to feel comfortable. A mortgage doesn’t care how many pre-IPO stock options you have.
“The vast majority of young people take the least amount of risk early in their career, when it’s actually the time they can afford to take the most,” Rob said. Looking back on leaving finance, he put it simply: “It would have been a lot easier at 24 than it was at 28.”
Of course, Rob at 24 wasn’t Rob at 28. He didn’t have the PE experience, the network, or the business judgment that came from watching deals up close. Would 24-year-old Rob have built Float? Probably not.
But here’s what Rob learned: there’s never a perfect time. You’ll always have a reason to wait. At 24, you don’t have experience. At 28, you have a mortgage. At 35, you have kids in school. At 45, you’re thinking about retirement savings.
The question isn’t whether 24-year-old you could build the same company 28-year-old you can build. The question is the same one Jeff Bezos uses in his risk minimization framework: At the end of my life, will I regret not having done this?
Rob wishes he’d started at 24 not because he would have built Float then, but because he would have built something. And that something would have taught him lessons that took years in corporate to learn.
The perfect timing doesn’t exist. Waiting for it only guarantees you’ll never start.
Ideas mean nothing; execution is everything
Remember the last time you submitted an expense report? The receipt dated June 30th, but your credit card statement showed July 1st? Your finance team makes you wait a month, then schedules a 30-minute meeting to sort it out while you’re still carrying a $500 charge on your personal card.
Float eliminates those problems by automating what used to take finance teams days to complete. Corporate cards, expense management, and bill payments, all built for Canadian businesses.
“It was a ‘duh’ product. We never struggled for product-market fit,” Rob told me.
The hard is often not the idea, but actually building the business.
Rob’s differentiator, he says, is that he does things when other people don’t.
“A lot of what I thought about business building was wrong. Insights are easy, but getting stuff done is the hard part.”
He learned this from watching another Canadian success story: Shopify. CEO Tobi Lütke once spoke about hiring on a podcast. As Shopify grew, impressive developers applied for jobs, but hiring didn’t get easier. Lütke realized the challenge wasn’t finding skilled workers, but rather finding people who would take full ownership.
“The hardest thing is not intelligence. It’s courage,” Rob said.
At Float, courage means shipping fast. The team measures themselves on output, not hours. They don’t wait for perfect. They build, learn, and iterate.
“I’m not sorry for having high expectations. I’m not sorry for wanting to be the best. I’m not sorry for demanding excellence from myself and from my team,” Rob said.
Canada is the right place, right now
Yes, the US market is bigger. Yes, US salaries are often higher. But here’s what Rob and his co-founders discovered when they nearly started Float in the United States.
“We had been diluted into thinking that in Canada, we can’t have better things, and things always come to Canada late and watered-down,” Rob said.
So they looked at the numbers.
Canada has over a million small and medium-sized businesses employing over 5 million people. A $10 monthly subscription on just 10% of that population is a $60M annual recurring revenue business.
“Our addressable market has proven to be so much larger than we originally predicted,” Rob said. “Many Canadian businesses are 20 years behind the technology curve.”
Float found a big market, hungry customers, and competitors who don’t believe the market is worth building in.
What about talent?
Canadian schools like the University of Waterloo regularly produce more founders in prestigious Silicon Valley accelerators like Y Combinator than many Ivy League schools. They’re among the most highly represented institutions at big tech companies in San Francisco. You can’t walk two blocks there without bumping into someone who has spilled a Tim Horton’s Double Double on a Go Train.
The exodus of Canadian talent to the US, ”Brain Drain,” as it’s commonly called, is real. But it’s not the whole story. And it’s reversible.
The inflection point is here. Canada is reducing barriers to interprovincial trade. Tax policy is shifting to favor business investment. The infrastructure for building great companies exists.
We just need entrepreneurs.
What Now
If you’re considering a move to Silicon Valley, run the numbers first. Could your business work in Canada?
If you’re an investor, back Canadian founders building for the Canadian market. Float proved the returns are there.
If you’re choosing between that $200k offer in San Francisco and a startup in Toronto, remember Rob’s wisdom around there never being a perfect time to take a startup leap.
And if you have a mortgage and kids? You don’t have to quit your job tomorrow. Start building something on the side. Test your idea. Talk to customers. The risk of waiting is greater than the risk of starting.
I’m writing this as much for myself as for you.
Canadians are known for being polite. But it’s time to stop apologizing and start building.
The longer we wait, the harder it becomes.
Give me a call in five years. If I haven’t taken my own advice by then, I better have a good reason.
Rob’s Not Sorry
Written by Rob Khazzam
I’m not sorry for having high expectations for Canada or for insisting we unleash the full potential of our >1M Canadian SMBs. I’m not sorry for rejecting low customer service standards, demanding 24/7 digital-first experiences, and fighting complacency throughout our country and industry.
Three Winning Principles I Live By
Where there’s a will, there’s a way.
Most things that look impossible are just unsolved.
The job of a founder is to refuse the default constraints and keep pushing until a path forward is found.
Resourcefulness beats resources almost every time.
Winning is a conscious choice.
You will encounter failure constantly; it is inevitable in life and your career.
What matters is whether you learn fast, adjust, and keep going.
The people and teams that ultimately win are the ones that simply refuse to stop.
Courage is rare, bet on yourself.
Intelligence is abundant. Courage is not.
The willingness to take risks, speak plainly, and pursue ambitious ideas when others doubt you is what creates progress in the world.
One thing to takeaway
Stop being passive and go build something. The world is not built by people who are smarter than everyone else, it is built by people who take action. If you care about Canada’s future, start something and keep going.
Thanks for reading. Subscribe to join us in championing the unaplogetic.
 | A guest post by
|
Rob's path is interesting because he actually had the "safer" option wired in - Ivey, Bay Street, the whole playbook - and still chose to build. I wonder if that actually made it easier or harder. Like, did having the escape route make him more confident to stay, or did it take longer to convince himself he didnt need it?
The "Canada is the right place now" thing feels true, but I'm curious what changed. Was it just that the talent and capital got better, or did Canadian founders finally stop waiting for permission from Silicon Valley?