It’s not every day you hear an accounting executive talk about seasonal allergies and emotional support. But that’s exactly where my conversation began with Lawrence Levinson, Vice President of Customer Success at Wave —a cloud-based accounting platform built specifically for small businesses.
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From his office in Toronto (while I held down the “vacation capital” of New Jersey), Lawrence joined me on The Rundown with Ramon to unpack not just numbers and invoices, but the emotional journey behind every entrepreneur’s bank balance. And what unfolded was a surprisingly human look at an industry most small business owners dread.
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Key Takeaways:
- Wave is on a mission to make accounting painless—and even empowering—for small business owners.
- The company offers a suite of tools from invoicing to bookkeeping, payroll, and advisory services tailored for entrepreneurs earning anywhere from $500 to $5 million.
- Wave emphasizes simplicity, emotional understanding, and community as pillars for financial success.
- AI is being used to streamline repetitive tasks like auto-categorization, but Wave maintains a human-first approach.
- Emotional resilience, community, and incremental progress are key to thriving as a small business owner.
From Shoebox Accounting to Trusted Simplicity
Wave was founded in 2010 by small business owners who had felt the pain of managing their finances with outdated tools. The company began with one radical idea: accounting should be free, intuitive, and beautiful.
“People were telling us, ‘Your software is gorgeous—but we still don’t want to use it,’” Lawrence admitted with a laugh. That realization gave birth to Wave Advisors, a team that helps entrepreneurs with bookkeeping and accounting coaching—either incrementally or fully outsourced.
Whether you’re a solopreneur earning $700 or a microbusiness doing $500,000 a year, Wave serves entrepreneurs in every stage of their journey. Lawrence breaks it down as: Start, Survive, Thrive.
- Start: You’re just sending your first invoice.
- Survive: You’re tracking expenses and managing cash flow.
- Thrive: You’re running payroll and preparing for long-term growth.
Wave’s product suite scales along with each phase—from free invoicing tools to smart categorization, payroll management, and embedded payment options.
Why So Many Entrepreneurs Avoid Accounting
Lawrence was honest about the emotional minefield around bookkeeping. “The word ‘IRS’ triggers people,” he said. “Cash flow, reconciliation—these aren’t just financial terms. They’re emotionally loaded.”
And he’s right. Most business owners don’t start a company dreaming of spreadsheets and tax filings. They’re coaches, designers, landscapers—creators with passion, not accountants.
That’s why Wave focuses on building a customer experience that doesn’t intimidate. “Our job is to take the worst part of your day and make it delightful,” he said.
Best Practices from the Front Lines
As someone who oversees all customer-facing operations at Wave, Lawrence has a front-row seat to what works—and what doesn’t—for business owners. His advice?
- Separate business and personal expenses. This simple step can save hours of confusion and stress at tax time.
- Stay on top of transactions. Snap photos of receipts immediately. Use Wave’s mobile tools to automate the process.
- Reconcile monthly. Don’t wait until the end of the year. Small, consistent steps build long-term peace of mind.
- Use automation. Wave’s invoicing system sends payment reminders—so you don’t have to chase clients down awkwardly.
- Schedule your financial hygiene. Treat your bookkeeping like a recurring appointment, not an afterthought.
The biggest insight? Many entrepreneurs are willing to pay just to be held accountable—just like hiring a personal trainer. Wave has built that into their offerings.
AI That Works Quietly (and Respectfully)
Yes, Wave uses AI—but not in a way that feels overwhelming or intrusive.
Right now, AI is helping with tasks like auto-categorization of expenses. “If we see a pattern in your transactions, we’ll suggest categories to save you time,” Lawrence explained. But Wave is cautious about going further. “AI sounds smart, but it can be confidently wrong. That’s risky in finance.”
Instead of chasing AI headlines, Wave is focusing on real-world applications that enhance customer experience while preserving accuracy and trust.
The Emotional Journey of Entrepreneurship
Beyond the tools, Lawrence offered one of the most compassionate takes I’ve ever heard from a SaaS executive.
“Don’t take this lightly,” he told me, referring to the leap into entrepreneurship. “Social media glamorizes business ownership, but it’s a hard road. It takes resilience, courage, and community.”
He emphasized listening to customers, launching before you’re “perfect,” and remembering that business—like love—is built on consistency, not hacks.
His final point was one many founders overlook: Find a community. Being in business can feel lonely. But there are countless others dealing with the same challenges—and many are eager to help.
Final Thoughts: A Platform Built for People
Wave isn’t just trying to be a cheaper or simpler alternative to traditional accounting software. It’s trying to make the emotional load of financial management lighter.
And as Lawrence put it best: “Happy customers buy more. They also forgive more. That only comes from building real trust.”
If you’re looking for a platform that understands not just your balance sheet—but your entrepreneurial journey—Wave might be the quiet partner you didn’t know you needed.
Visit waveapps.com to explore their free tools and see if it’s the right fit for your business.
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