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

Why many founders lose thousands of dollars hiring the wrong developers
The hidden risks of relying too heavily on off-the-shelf software tools
When it actually makes sense to build custom software
The problem with overloading your business with too many tech tools
Why entrepreneurship is far harder and more consuming than most people expect
The importance of validating your business idea before building anything
How founders can protect themselves from bad contracts and development traps
Why delegating early can accelerate business growth
The difference between building a prototype and building secure, scalable software
The power of community within Alberta’s growing innovation ecosystem

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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