The Profit or Pivot Podcast

What happens when AI stops helping employees and starts replacing them entirely?

Sam Pasupalak joins Matan to explain his plan to build an AI CEO, why he believes today’s LLMs fall short, and how buying small businesses could help test his thesis. Sam co-founded Maluuba, the AI startup acquired by Microsoft for $160 million.

In this conversation, he traces the evolution from early voice assistants to deep learning and ChatGPT...

Yishay Waxman built Platterz into a Canadian tech success story with roughly a $100 million run rate.

Then COVID hit.

Offices shut down, revenues disappeared, and the company was forced to lay off more than 70% of its employees.

Instead of shutting the company down and returning the remaining capital, Yishay and his co-founder pivoted. Years later, the business was acquired by Gusto.

Margins are tight. Inventory is expensive. Customer acquisition costs keep rising. And in Canada, raising venture capital for consumer products is almost impossible.

In this episode of The Profit or Pivot Podcast, I sit down with Dani Kagan, co-founder of Mave & Chez, to discuss what it really takes to build a premium consumer ...

Roman Baber was excommunicated from the Conservative movement in Canada because he stood up to COVID related government tyranny in 2021. He was kicked out of the Progressive Conservative Party of Ontario, and spent several years in the political wilderness.

In hindsight, his stance was measured, appropriate, and necessary, during a time of fear, mass delusion, and government lies.

And fortunately, his story doesn't end there.

He wa...

After October 7th, everything changed.

Not just on the ground in Israel… But in the digital battlefield where narratives are shaped, distorted, and weaponized.

In this episode of The Profit or Pivot Podcast, I sit down with social media superstar Hillel Fuld to break down what’s really happening. Hillel built his career advising startups and telling stories in the tech world. But after October 7th, he shut it all down ...

Every founder wants to raise money.

But few understand what they’re actually competing against. In this episode of the Profit or Pivot Podcast, I sit down with Jeffrey Fidelman to break down what really happens behind the scenes in venture capital and why most founders never even get a shot.

Here’s the reality:

Top firms are reviewing thousands of deals every year. One fund alone can see 5,000 applications annually and ...

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Ever wonder how someone becomes a venture capitalist?

Winter Mead is the founder of Coolwater Capital, the YC for VC funds. He's invested in over 90 funds and has helped launch hundreds of VC firms. Venture operates in circles of trust. Those circles aren’t arbitrary, they’re built over decades. Ecosystems compound rel...

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Everything is degrading in major cities like Toronto.

Violent crime has skyrocketed, homelessness is rampant, living is increasingly unaffordable, and we are paying more in taxes & receiving worse services. In the latest episode of The Profit or Pivot Podcast I am joined by Toront...

Jim Ferry, a Partner at Volition Capital with $1.7B AUM, recently posted a VC analyst role and received 2,500 applications in one week.

That number alone says everything. In this episode of The Profit or Pivot Podcast, we unpack what that level of competition really means, why traditional career advice is broken, and how hiring managers actually think when they’re flooded with applicants who all look the same on paper.

If you...

Who you know in business is critical to your success, especially as a startup. And meeting the right people whether its best employees, partners, customers, and investors often requires networking and meeting new people in person.

But what if you're an introvert like me and dread networking and meeting new people in person?

There are a few simple and easy steps you can implement to overcome your fear, get out of your comfort zone a...

Max Abergel signed one of the most influential rappers in the world without an intro, a résumé, or permission. He literally slipped past security and walked into a green room.

That moment led to a long-term partnership with Waka Flocka Flame, an artist with diamond-certified records, collaborations with Nicki Minaj and Drake, and a brand that stretches far beyond music into business, philanthropy, and politics.

But this episode isn...

Every brand is trying to influence you but only a few succeed. Why? Because great brands understand human psychology better than their competitors.

In this episode of the Profit or Pivot Podcast, I sit down with Rena Nickerson, the General Manager of the Quaker and Sabra brands in Canada, who has spent her career understanding how people think, what motivates them, and how to turn that into real business growth.

We go deep into the...

Ever wondered how the Russian oligarchs were made? This episode gives you a glimpse into that world… through someone who lived it, built through it, and survived it.

In this episode of The Profit or Pivot Podcast, Matan speaks with Marat Ressin, an entrepreneur who built and bought over 30 businesses after the fall of the Soviet Union, escaped the rising control of the KGB to Canada, and went on to build the #1 ranked univer...

By his mid 20's, Ryan Henry became Head of Engineering for a fast growing mobile game developer. It was his first exposure to scaling a tech company, which he later leveraged at Freshbooks, a Canadian "unicorn" startup (over $1 billion valuation). At Freshbooks, Ryan hired 100 engineers in 1 year, a real rocket ship. He shares his insights on scaling a business, hiring the best people, how AI will change the tech landscape, and oth...

Geoff became an accidental entrepreneur building a 150 employee business and becoming a prolific angel investor with investments that include a $500 MILLION exit.

Geoff's journey illustrates the unpredictable path of entrepreneurship, highlighting the importance of adaptability, continuous learning, and being open to unexpected opportunities. Geoff and I discuss how to build a business, the many tough choices one has to make, and t...

By age 22, Alex Siplyarsky failed in his 1st business, was $40,000 in debt, and had his 1st child on the way.

Life looked bleak and he didn't know how to dig himself out of this deep hole. However, Alex defied the odds. Initially struggling with sales, he transformed his life by understanding what makes buyers tick and how to overcome an initial "no" and influence people to buy.

Starting with the humble beginnings of selling chocol...

🏠 Is Canada’s dream of home ownership officially dead?

In this episode of the Profit or Pivot Podcast, I sit down with Mark Freedman, entrepreneur, investor, and former Head of Product who helped lead a startup to a $100M+ exit, to talk about building and scaling businesses, product leadership, and why real estate in Canada and other major cities is becoming increasingly out of reach.

Mark shares how he helped grow a SaaS co...