From Haircuts to Donuts: The Journey of a Serial Entrepreneur feat. Thomas Matthews

04/17/25 • 43 min

What does it really take to grow a successful business from the ground up?

Today we sit down with entrepreneur Thomas Matthews for a candid conversation about the challenges, pivots, and lessons that have shaped his journey. Growing up in a large family of eight, he learned early on the value of hard work and determination. His entrepreneurial spirit ignited when his uncle gave him a chance to cut hair, leading to a thriving clientele built on exceptional customer service and word-of-mouth referrals.

From launching his first venture to scaling into new opportunities, Thomas shares real-world wisdom on mindset, mistakes, and staying hungry. As someone who has found success customer service, real estate, and the restaurant world, he has some great stories to share and will motivate you to take a chance by chasing your dreams.

Get ready for stories, strategies, and a few hard truths about what it really means to build your own path in business.

Here’s what we discuss in this episode:

🚀 How Thomas launched and grew his business

💡 Lessons learned from early failures and pivots

🔁 The importance of adapting and staying hungry

💬 Real talk on leadership, risk, and mindset

👥 Why your circle matters more than you think

0:00 – Thomas’ background

5:01 – Consistency with clients

9:09 – Hair studio

12:28 – Property company

22:58 – Managing risk

28:29 – Donuts

33:34 – Overruled! Segment

Visit us online: https://www.scottvicknair.com/

Watch the Podcast on YouTube: https://bit.ly/3TgD9jP

Send us a text

What does it really take to grow a successful business from the ground up?

Get ready for stories, strategies, and a few hard truths about what it really means to build your own path in business.

Here’s what we discuss in this episode:

🚀 How Thomas launched and grew his business

💡 Lessons learned from early failures and pivots

🔁 The importance of adapting and staying hungry

💬 Real talk on leadership, risk, and mindset

👥 Why your circle matters more than you think

0:00 – Thomas’ background

5:01 – Consistency with clients

9:09 – Hair studio

12:28 – Property company

22:58 – Managing risk

28:29 – Donuts

33:34 – Overruled! Segment

Visit us online: https://www.scottvicknair.com/

Watch the Podcast on YouTube: https://bit.ly/3TgD9jP

Previous Episode

FOX 8 Sales Director Andy Delaporte Talks Media, Hockey & Wine

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Today we’re welcoming on a close friend of ours and someone we’ve grown to know well thanks to our shared love of wine. Join us as we sit down with Andy Delaporte, the Director of Sales for Fox 8 WVUE, to discuss a smattering of topics over a wonderful glass of Italian wine.

We’ll get into his unexpected path into media and learn more about what makes a great salesperson, how to manage and motivate a team, and the power of relationships in business. But Andy’s story goes well beyond his successful sales career, so we talk wine, converting hockey fans, and the importance of building a strong personal network.

Here’s what we discuss in this episode:

📺Andy’s Unexpected Journey into Media

💼 Sales Tips & What Makes a Great Salesperson

🏒🎸 New York Islanders & The Grateful Dead

🍕🍤 The Great Restaurant Debate: New York vs. New Orleans

0:00 – Intro

1:26 – Andy’s First Media Job

8:32 – Tips on Managing a Sales Team

10:01 – Qualities of Great Salesperson

15:02 – The Grateful Dead

18:18 – For the Love of Hockey

22:10 – Overruled!