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What happens when you start a business in an industry you were never planning to enter?


In this episode of Owner’s Roundtable, Jeff McLarty sits down with Rea Hailley, co-founder of New Idea Machine, to unpack the unfiltered realities of entrepreneurship, building in the tech ecosystem, and why many founders unknowingly walk into expensive software mistakes.


Rea’s journey into entrepreneurship was anything but planned. A casual conversation on a dog walk turned into the launch of a software development company built around one mission: helping founders avoid the costly pitfalls of custom tech development.


From navigating the overwhelming world of tech stacks to confronting the emotional highs and lows of building a company, Rea shares the lessons she’s learned while growing a business in one of the most complex industries for non-technical founders. This conversation explores the unromantic side of entrepreneurship, why founders need to ask better questions before building software, and how transparency can reshape the relationship between developers and business owners.


If you’re thinking about launching a tech product, this episode delivers practical insight from someone who’s learning the game in real time.

What You’ll Learn in This Episode

About Rea Hailley

Rea Hailley is the co-founder of New Idea Machine, a software development agency focused on helping founders and business owners build smarter digital products. With a background in business and experience as a Merchant Success Manager at Shopify, Rea combines entrepreneurial insight with a commitment to transparency in an industry that often feels difficult to navigate.


Beyond her work with New Idea Machine, Rea is also a host on the Leaders, Innovators and Bold Ideas (LIBI) podcast, where she interviews entrepreneurs, innovators, and founders from Alberta’s growing tech ecosystem. Her mission is simple: help founders build better products by giving them the knowledge they need before writing a single line of code.

Resources discussed in this episode:

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