What happens when entrepreneurs stop improvising their finances and start building smart, sustainable systems? They scale faster, reduce burnout, and gain the freedom to actually grow their business.
On our first season of Greater Than The Sum, we spoke with Canadian SMB owners and experts who’ve lived this transformation firsthand. From late-night check-writing to scalable fintech stacks, their stories offer a playbook for entrepreneurs and finance professionals alike.
Here are the top takeaways from the first season:
1. Take financial management seriously — early
Christine ran multiple businesses — from media and apps to consulting — before realizing she had overlooked one thing: the financial foundation. It wasn’t until she took a financial workshop (thinking she already knew everything) that she realized just how much she didn’t know. That wake-up call sparked a new level of financial discipline — and a dramatic turning point in her business growth.
Peer tip: Don’t wait 10 years to build financial literacy. Invest early in understanding cash flow, hiring advisors, and building systems that scale.
Watch or listen to the episode.
2. Automate early, automate often
Paying over 150 contractors biweekly used to consume days of staff time — and countless questions from contractors wondering when they'd be paid. Noah adopted Plooto to automate and centralize their payment workflow. The impact? Huge time savings, fewer questions, happier vendors, and more focus on strategic work.
Peer tip: Look for automation that also improves the experience — for your team, your vendors, and your clients. Trust and transparency matter.
Watch or listen to the episode.
3. Understanding cash flow is key
Freightzy grew fast — and so did the complexity of its finances. Sean described the chaos of check-based payments: vendors cashing them unpredictably, clients paying 30+ days out, and no clear cash picture. It wasn’t until they digitized payables and receivables (with Plooto's Quickbooks integration) that they finally gained visibility — and peace of mind.
Peer tip: If you can’t answer “how much cash do we actually have?” at a glance, it’s time to upgrade.
Watch or listen to the episode.
4. Great tech is nothing without great people
Across every episode, one theme stood out: behind every smart system was a sharp human. Whether it was a fractional CFO, a savvy bookkeeper, or a trusted accountant, founders repeatedly credited their financial turnaround to the people who helped them see the full picture — and make better decisions.
Peer tip: Automate the low-value tasks so your experts can focus on
high-value strategy.
Watch or listen to the episode.
5. Sustainable growth beats fast growth
Startups often chase rapid growth or stretch themselves to the brink. But multiple guests emphasized the value of growing intentionally. That means making smart financial bets, not cutting corners on operations, and investing in tools and talent that can grow with you.
Peer tip: Don’t just plan for tomorrow. Plan for next year — and the years after that.
Watch or listen to the episode.
6. Build trust through process
Handling investor funds — especially in small, syndicated angel rounds — comes with intense scrutiny. Startup TNT took a big risk moving off e-transfers to Plooto for investor payments, but the result was a massive boost in credibility, professionalism, and growth. Trustworthy, automated payments became a backbone of the operation.
Peer tip: Your financial operations reflect your brand. Make sure they build trust.
Watch or listen to the episode.
7. Avoid burnout by delegating + systemizing
Burnout came up in every conversation. Founders learned (often the hard way) that delegation, process, and automation aren’t luxuries — they’re survival tools. Freeing up your mental space and your calendar is what gives you the clarity to grow, innovate, and thrive.
Peer tip: If you’re doing it all yourself, your business can’t scale.
Start handing it off.
Watch or listen to the episode.
The future belongs to financially fluent founders
If there’s one lesson that connects all four of these founders, it’s this: you can’t do it all yourself, and you shouldn’t try. Whether you're running lean or scaling fast, technology is a powerful way to multiply your time and reduce the weight of manual financial tasks.
The right tools don't just save time; they give you the space to focus on what really matters: growing your business, building strong customer relationships, and making smarter decisions.
Understanding your cash flow in real time isn’t a nice-to-have; it’s essential. You need visibility into where your money is moving and confidence that it’s going where it should. With the right financial systems in place, you can securely delegate tasks to team members or external partners without sacrificing control or oversight.
Invest in systems that give you clarity, control, and room to lead.
