In this episode, we dive into the entrepreneurial journey of a second-generation business builder. Inspired by the financial struggles he witnessed at home, he pursued a career in accounting and later launched a successful bookkeeping firm for construction businesses in Canada. He shares lessons learned from rapid startup growth, the importance of accurate financials, and how those insights led to his current venture: building AI-powered error detection software for bookkeepers. This candid conversation is full of valuable insights for any entrepreneur navigating finance, hiring, and finding product-market fit.

Leeroy Beeby is from South Africa, living in Toronto, Canada. He is a Qualified Chartered Accountant, Entrepreneur and Businessman, and Co-Founder of Check The Level, your automated bookkeeping assistant.

Watch this episode on YouTube: https://youtu.be/dTXAAcZw9ww

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Website: www.checkthelevel.com

Instagram: @checkthelevel

Email: [email protected]

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The Entrepreneurial Elevation Podcast and content posted by Kelley Beveridge is presented solely for general informational, educational, and entertainment purposes. The use of information on this podcast or materials linked from this podcast or website is at the user's own risk. It is not intended as a substitute for the advice of a physician, professional coach, psychotherapist, or other qualified professional, diagnosis, or treatment. Users should not disregard or delay in obtaining medical advice for any medical or mental health condition they may have and should seek the assistance of their healthcare professionals for any such conditions.

Transcript

[00:00] Leeroy shares how growing up in an entrepreneurial household in South Africa shaped his passion for business and accounting, particularly after witnessing his parents' struggles with finances.

[02:30] He details his journey from working in Bermuda to moving to Toronto, studying at the University of Toronto, and being introduced to the local startup ecosystem.

[04:45] The choice to target construction companies stemmed from personal connections and research that revealed a high failure rate in the industry—largely due to poor financial tracking.

[07:30] Leeroy explains how he and his co-founder developed a tool to help construction companies with job costing and cash flow by offering better bookkeeping.

[10:15] After experiencing rapid growth with a bookkeeping firm, Leeroy identified a new opportunity—building an “error detection assistant” for QuickBooks that flags mistakes and boosts financial accuracy.

[13:20] He shares candidly about the stress and lessons learned from building a 7-figure business with 20 employees in just 18 months—and how it influenced his move toward a more scalable model.

[17:00] Advice for entrepreneurs: Know your numbers, use AI tools for basic financial understanding, and don’t try to do it all—get a good bookkeeper and understand the basics of your P&L and balance sheet.

[22:00] Leeroy outlines common errors like inconsistent tax coding, incorrect invoice dates, and a lack of financial review, which his tool helps identify.

[27:00] He shares a story of how his software helped improve team training and performance in bookkeeping firms, creating better communication and feedback culture.

[35:00] Leeroy emphasizes learning outside of your comfort zone, always seeking feedback, and building a business that aligns with your long-term vision and lifestyle.