About Sam Penny — Coach for the Brave

If you're looking to sell your business for what it’s really worth — or you're ready to buy a business without making expensive mistakes — you're in the right place.

I'm Sam Penny. I help business owners and investors make bold, smart decisions in high-stakes moments. Whether you're preparing to exit or exploring your first acquisition, I coach you through the strategy, psychology, and structure required to win.

For Business Owners Ready to Sell

You’ve spent years building. Don’t let emotion, burnout, or poor advice rob you of what it’s worth.I coach business owners who want to:

• Sell for a premium — not a discount
• Prepare their business to thrive without them
• Create clean systems, strong valuations, and a confident exit
• Avoid leaving money on the table

I’ve built and sold multiple businesses myself, including a $10M+ eCommerce brand and a $10M+ medical device company. I know what’s at stake — and I help you take control before it’s too late.

A little more about me

You need to be remarkable to stand out from the crowd

I've always done things differently. My journey in small business has been rewarding, terrifying, exciting, punishing and worth every second. I worked my ass off to build my skill set to set up me for success, but to also give others access to what I know. I have built several businesses in mytime. Some great, some not so. But damn I've learned a lot along the way. I have a Bachelor of Engineering (Civil), an MBA (Marketing, Finance & Entrepreneurship) and studied at MIT's Sloan School of Business. I ran Cheese Therapy (Australia's largest online artisan cheese retailer) and created Max+Tom (artisan cheese range). I have had a successful medical device company that had distribution through 1,500 pharmacies and had a chain of 7 hair salons (I know, random!). There's loads more on top of this. In 2022 I had the privilege of delivering a TEDx talk about why people around the World should support small artisan producers. Some of the other recent random things I have done:

• Swimming the English Channel (2018)
• The 6th Australian to swim an Ice Mile (2019)
• The first person in the World to attempt to swim the English Channel in Winter (2019)
• Ran 120km in 24hrs on an athletics track (2024)

I love trying new things and seeing what happens. My favourite saying is
"If you aint the lead dog, the scenery never changes"
I love working with people who have artisan businesses because they make our World a better place. I want to help you realise your true potential and help you build a better business for you.

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Some podcast & interviews that I've done

One-on-One Coaching

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In this episode of Add To Cart, we are joined by Sam Penny from Artisan’s Bend, a curated marketplace for artisan producers. He is also behind the great online cheese shop, Cheese Therapy. According to Sam, they are now the largest cheese retailer behind Woolies and Coles. This is Sam’s latest venture and just one of the many strings to his bow - he’s a former soldier, engineer, extreme swimmer and cheesemonger...oh and he used to own hair salons. Slowing down is now at the heart of Sam’s business and the unique food and drink available through Artisan’s Bend is the kind that takes its producers time to get right. In this chat, we talk all about Sam’s colourful past lives, discuss how the success of his other business, Cheese Therapy, led to a marketplace, why content creation is a huge part of the business and what it feels like to go where no man has ever gone before.

Small Business Big Marketing

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Cheese Therapy founders Sam Penny and Helen Shadforth have single-handedly saved Australia’s artisan cheese making industry from going under following bushfires, drought, economic turmoil and now COVID-19. Host Tim Reid finds out how they did it.

The Greatness Machine

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On today's episode of The Greatness Machine, Darius chats with Sam Penny, who with his wife operates Artisans Bend (Cheese Therapy), Australia's largest artisan cheese retailer. Sam is passionate about strategy, marketing, and the pursuit of the perfect cheese. In the sports world, Sam made the first attempt to swim the English Channel in Winter, has run 120km in 24 hours, and swam an Ice Mile in 3.9-degree celsius water. You'll discover what life looks like as a serial entrepreneur. You'll learn about Sam's passion for cheese and how he became the "Cheese Monger." You'll also discover what it was like to swim the English Channel... in Winter! Join Darius and Sam as they explore the tasty world of cheese, entrepreneurship, and how it feels to swim in essentially frozen water. Topics include: • Life as a serial entrepreneur • How and why Sam shifted from running a medical device company to the role of "Cheese Monger” • What it was like to be the 191st Australian to swim the English Channel • And other topics...

That Voice Podcast

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If you're afraid to jump in the deep end when it comes to any type of speaking - this episode is for you. Hear from the first person in the WORLD to attempt to swim the English Channel in winter! Sam Penny is a hell of an inspiration and a shining example of why you should give it a go - whatever 'it' may be.

Effortless Swimming Podcast

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Our guest for todays episode is Sam Penny who is the first person who attempted to swim the English in winter. In this episode, we talked about Sam’s training, strategy and his journey in crossing the English Channel.

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Sam Penny is a pioneering entrepreneur in the gourmet food industry, best known for founding Cheese Therapy, a company dedicated to delivering artisanal cheeses to doorsteps nationwide. With a passion for supporting small-scale cheese producers and providing cheese lovers with access to some of the world's finest cheeses, Sam has built Cheese Therapy on the principles of quality, community, and sustainability. Before embarking on his journey with Cheese Therapy, Sam garnered experience in various sectors, including business development, marketing, and the culinary arts. This diverse background has equipped him with a unique blend of skills that was crucial in shaping the success of Cheese Therapy. Under his leadership, the company not only thrived as a business but has also created a vibrant community of cheese enthusiasts, connecting people through the love of cheese.

Some of the recent crazy things I've done

Swam the English Channel

I've never been a long distance swimmer but wanted to see what the journey would be like.

Swam an Ice Mile

Swimming a mile in 3.9deg water is CRAZY! This was a massive challenge that I set. It was scary.

World Record Attempt

I am the first person in the World to attempt to swim the English Channel in winter. Sometimes you just need to see what happens...