Episode Details

From building a $100M software business to watching it fall apart—here’s what really happened.He built a software company from the ground up and scaled it past $100M in sales.

Matthew Whyatt started his first tech business at 22—and learned the hard way what happens when growth, partners, and focus drift off course.In this episode, Matthew breaks down the real story behind scaling fast, losing focus, and the lessons that reshaped how he thinks about sales, leadership, and building sustainable companies.

He shares why sales is the lifeblood of every business, how founder-led sales eventually breaks, and what it actually takes to build a repeatable sales culture.If you’re a founder navigating growth, sales, or scaling challenges, this conversation is full of hard-earned lessons.

What you’ll learn in this episode:

How Matthew scaled a software business past $100M in sales

Why diversifying too early can derail focus on your core business

How misplaced trust and lack of verification can destroy a company

What breaks when a founder-led sales team tries to scaleHow to build a repeatable sales culture rooted in diagnosis, not pitching

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Here's what you're in for:

00:00 Introduction and Guest Welcome

00:36 Starting a Business at 22

01:14 Early Marketing Strategies

01:57 Expansion and Diversification

04:26 Challenges with Business Partners

11:07 Boardroom Dynamics and Decision Making

22:41 Sales Culture and Ethical Practices

26:11 Opening a New Zealand Office

27:28 Financial Troubles and Trust Issues

29:04 Tax Problems and Internal Mismanagement

30:06 Data Supplier Issues and Business Liquidation

32:49 Rebuilding and Moving Forward

37:45 Sales Strategies and Lessons Learned

40:43 Advice for Founders on Sales Culture

49:40 The Importance of Diagnosis in Sales

55:42 Final Thoughts and Contact Information

ABOUT MATTHEW WHYATT

Matthew is a sales and go-to-market expert with over 25 years of experience in software and SaaS. He has built, scaled, and exited multiple software businesses and has been involved in more than $100M in tech sales.

He is the founder of TechTorque, where he helps software and SaaS companies sharpen their strategy, improve their sales process, and build revenue-driving marketing engines.Matthew is also the host of The CEO and the Salesman, a podcast focused on practical lessons from founders and operators on what actually works in business.

You can reach out to Matthew through:

LinkedIn: https://www.linkedin.com/in/matthewwhyatt/ Website: https://techtorque.com.au/

ABOUT JASON KIRBY

Jason Kirby is the co-founder of Thunder, a tech-enabled investment bank helping founders reach their ideal target outcomes through capital strategy and M&A. He is a serial entrepreneur with four exits and decades of experience in fundraising, M&A, and business building.

In his career, he has coached hundreds of entrepreneurs on fundraising, investing, capital strategy, M&A, and business development. He’s transacted over $135M and his firm Thunder has transacted over $200M+

You can reach out to Jason through:

Email: jason@thunder.vc

LinkedIn: https://www.linkedin.com/in/jasonrkirby/

ABOUT $100M EXITS