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Lessons Learned from a Massive Exit: A Candid Conversation with Kirk Simpson
Watch on YouTube ↗From Broom Closet to $537M Exit: Kirk Simpson on Building Wave and Starting Over
Watch on YouTube ↗Every talk is searchable — ask the archive about Wave ↗
About
Kirk Simpson and James Lochrie started Wave in 2009 in Toronto's Leslieville with a contrarian bet: give the world's smallest businesses — the freelancers and nine-person shops the big accounting vendors ignored — genuinely free accounting and invoicing software, and make money on payments and payroll instead of subscriptions. The bet nearly killed the company: by 2015 Wave was close to insolvent, and Simpson negotiated with Silicon Valley Bank from the office broom closet. Then the model caught. At its peak Wave was signing up 2,300 small businesses a day, and by 2019 more than 400,000 businesses were using the platform every month. H&R Block acquired Wave in July 2019 for US$405M (about C$537M) — at the time the seventh-biggest exit in the Canadian ecosystem — and kept the company operating under its own brand from its Toronto headquarters. Simpson stayed on as CEO until mid-2022, leaving after revenue passed $100M; former Mastercard and Afterpay executive Zahir Khoja succeeded him. As of mid-2026 Wave sells invoicing, accounting, payments, payroll, and advisor services to North American micro-businesses, and since February 2024 has paired its free Starter plan with a paid Pro tier.
Backers
Venture-backed before its exit: OMERS Ventures wrote Wave's first $500K cheque after Kirk Simpson pitched roughly 150 investors, and Charles River Ventures led a US$5M round in 2011. H&R Block acquired Wave in July 2019 for US$405M (about C$537M) in cash; it operates today as an H&R Block company headquartered in Toronto.
Around the web ×6
Quick answers
Is Wave still free?
As of July 2026, the free Starter plan still covers invoicing, estimates, and basic accounting. Since February 2024, new signups choose between Starter and a paid Pro plan (about $20 a month) that adds automatic bank-transaction imports, receipt capture, and reduced card fees. Wave's core revenue has always come from per-use payments and payroll fees rather than software subscriptions.
Who owns Wave today?
H&R Block, which acquired Wave in July 2019 for US$405M (about C$537M) in cash — at the time the seventh-biggest exit in the Canadian ecosystem. Wave kept its brand and Toronto headquarters, and powers H&R Block's books-to-tax offering for small businesses.
Where are the founders now?
Kirk Simpson stayed on as CEO for three years after the acquisition, stepping down in June 2022 once revenue had passed $100M; after building identity startup GoConfirm, he's now co-founder of Courtyard, helping small businesses find customers through AI (see his profile in this directory). Co-founder James Lochrie, Wave's original chief product officer, moved on before the acquisition and became an early-stage investor.