The Profit or Pivot Podcast

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 chocolates in middle school, Alex honed his sales skills through telemarketing and even selling diamonds. These experiences taught him how to build confidence, handle rejection, and thrive.

Alex developed his GRAC principle, which is his philosophy of selling:

Give value first, Resilience, Accountability, and Continued growth.

💡 His journey is a masterclass in entrepreneurship, focusing on relationship-building, marketing insights, and knowing when to pivot.

Alex offers practical advice. If you are building a business, looking to develop your sales skills, or looking to be inspired, you don't want to miss this episode!

🏠 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 company from $600K ARR to over $10M and what those lessons taught him about value creation, conviction, and execution. Now, as a partner at Stonefield Capital, he turns that same discipline toward real estate lending and investing, and offers an unfiltered take on Canada’s housing market.

We discuss:

• Why owning a home in Canada may soon be impossible for most
• The real cause of the housing affordability crisis
• Lessons from scaling a business to a $100M exit
• Why conviction and discipline matter in every market, housing or tech
• Why most startups underprice their products (and how to fix it)
• The art of letting go of bad customers

Whether you’re a founder, product leader, or investor, Mark’s journey is packed with lessons about growth, conviction, and building lasting businesses, and it’s a must-watch for anyone who cares about building wealth, investing smart, and understanding the future of real estate in Canada.

About Mark Freedman

Mark is a seasoned technology and financial services professional/entrepreneur with a track record of driving rapid growth and operational scale. Most recently, he helped grow Mortgage Automator from a 12-person, $500K revenue startup into a 65-person, $10M ARR company, culminating in a nine-figure acquisition within four years.

Before that, Mark held diverse roles across sports engineering, higher education, and financial services, as well as a brief period in consulting. He now serves as Managing Partner at Stonefield Capital, a private lending firm based in Canada, where he has helped grow assets under management by over 30% year-over-year, currently surpassing $50M.

A lifelong technologist and father of two, Mark is passionate about community building, mentorship, and leveraging technology to streamline traditional finance operations.

Connect with Mark

LinkedIn

Email:  ✉️ Mark@stonefieldcapital.ca

Join me as I sit down with Jeremy Zuker, a seasoned entrepreneur who has successfully built and sold multiple marketplace startups.

In this insightful conversation, we'll delve into: Growth Strategies: Learn how Jeremy scaled WagJag to 180 employees and $50 million in revenue.

• Bootstrapping Success: Discover why Jeremy chose to avoid venture capital and the benefits of bootstrapping.
• Overcoming Challenges: Hear about the tough decisions and setbacks that every founder faces.
• Building Strong Teams: Learn the importance of company culture and team dynamics.
• Angel Investing: Gain insights into Jeremy's perspective on investing in early-stage startups.

Don't miss this opportunity to learn from a seasoned entrepreneur and gain valuable insights into the world of startups and investing.

Learn more about Jeremy, Spacer & Scoop Commute

🇨🇦 Canada is not the country it once was.

Economic stagnation, failing institutions, rising crime, a massive brain drain, a housing crisis, and a political class unwilling to confront the growing divisions and hatred. In this episode of The Profit or Pivot Podcast, I sit down with Melissa Lantsman, Deputy Leader of the Conservative Party of Canada, to discuss what’s gone wrong in Canada and what it will take to fix it.

Melissa offers a candid look at the erosion of Canadian values, the failure of leadership, and how antisemitism has become normalized in our streets, schools, and political discourse.

We dive into:

•  
• Why Canadians are losing faith in their institutions
• Why the Conservative Party lost the 2025 elections & lessons learned
• Trump's role in the election, tariffs & thoughts on him as POTUS
• The failing economy, rising crime, housing crisis & other issues, & how to fix it
• The surge of antisemitism and how politicians enable it
• The culture of fear that stops people from speaking the truth
• What it will take to rebuild national confidence and unity

This episode is an unfiltered look at a country in decline, and a call for courage, moral clarity, and leadership before it’s too late.

_ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _

About Melissa Lantsman

Melissa is the Member of Parliament for Thornhill and Deputy Leader of the Conservative Party of Canada. Elected in 2021, she previously served as the Shadow Minister for Transport and as a Senior Advisor to leading Canadian political figures.

Melissa believes in breaking the mold and in bringing new ideas and energy to Ottawa. She represents the next generation in Canadian politics. Born and raised in the community she now serves, Melissa was taught by her immigrant parents to work hard and to stand up for what’s right. Those are values that have guided her in all points of her life and career.

Melissa is an award-winning communicator and was amongst Canada’s most sought-after public affairs executives. She has served on various boards of directors, was a regular TV commentator and hosted her own radio show. Her writing has been featured in Canada’s largest circulation publications. Melissa is not afraid to speak out for the things that matter, and she doesn't back down from holding the government to account.

Instagram / Facebook / X / YouTube: @MelissaLantsman

Substack 

Website 

How do you build a venture capital firm in a market that isn’t mature? And what does it mean to be an entrepreneur shaped by experiences in Iran, Israel, and Canada?

In this episode of The Profit or Pivot Podcast, I sit down with Sion (Zion) Balass, co-founder and Managing Partner of The Group Ventures, a Toronto-based VC firm. Sion shares his remarkable journey, born in Iran to Iraqi Jewish parents, moving to Israel after the revolution, building a startup in computational drug discovery (AI before “AI” was cool), and eventually co-founding one of Canada’s most concentrated and hands-on venture funds.

We dive into:

• The unique challenges of building a venture fund in Canada
• Why Israel’s startup ecosystem vastly outperforms Canada’s
• His “every company counts” approach to venture investing
• The role of government in entrepreneurship and where it fails
• A candid conversation on the rise of antisemitism in Canada since October 7, 2023

Whether you’re an entrepreneur, investor, or simply curious about the intersection of business, resilience, and identity, this episode offers an unfiltered look at the realities of venture capital and leadership today.

 Subscribe for more candid conversations with entrepreneurs, investors, and leaders who share their Profit or Pivot stories.

Watch the video version on YouTube 

About Sion Balass

As Founder and Managing Partner of The Group Ventures, Sion Balass leverages two decades of global tech leadership to scale early-stage companies into market leaders. From the fund's base in Toronto, and originally from Israel, Sion applies his international experience from the US, Germany, the UK, and Canada to guide founders on their path to global expansion. His hands-on support spans the entire company lifecycle, including architecting go-to-market strategies, securing funding, and navigating complex M&A transactions. Sion provides critical guidance through active board roles and as a trusted advisor, with a deep focus on digital health and AI.

 

Connect with Sion

Learn more about The Group Ventures 

Are you an entrepreneur feeling stuck, overwhelmed, or questioning if you should keep going? You’re not alone. In this 21-minute compilation, we've pulled together the most powerful insights from guests of The Profit or Pivot Podcast, founders, investors, and business leaders who have faced struggles just like you.

This episode is packed with real talk and actionable strategies to help you:

• Push through doubt and failure
• Build resilience in tough times
• Find mentorship and guidance
• Stay focused on what really matters

Whether you’re in the early grind of a startup, running a small business, or chasing your next big idea, this collection of wisdom will give you the clarity and encouragement you need to keep moving forward.

👉 Don’t forget to like, share, and subscribe for more insights on startups, venture capital, and entrepreneurship.

Watch the YouTube video here.

Jonathan built a successful news app that reached the top 10 on Apple's app store and decided to let the startup fail. In this video, Jonathan and I discuss his winding journey as a startup founder, the challenges he faced, why he let his startup fail, and why and how he ultimately revived it.

Also, we discuss how he made a lot of money trading stocks, why he is bullish on crypto and why he thinks Ethereum is the future of money. And unlike most of my guests, he is a family office investor with insights into how he and his family are approaching investing in this tumultuous time for VCs, startups and businesses in general.

I rarely speak with someone like Jonathan who has eclectic experiences and has found a lot of success very early in his career. If you're an entrepreneur, stock trader, crypto enthusiast or venture capital investor, you don't want to miss this discussion!

Connect with Jonathan:

LinkedIn 

Family Office 

How can ancient Jewish wisdom guide the way we live, work, and build businesses today?

In this episode of the Profit or Pivot Podcast, I sit down with R. Josh Kaller who is an entrepreneur, attorney, real estate investor, and community leader, to explore the intersection of Judaism, spirituality, and business. In addition to being a real estate attorney and investor, Rabbi Kaller is building a nonprofit like a business, where he can impact the community in a sustainable way.

Josh shares how his Jewish values shape his approach to leadership, decision-making, and self-improvement, and why success in business is about more than profit, it’s about purpose, community, and growth.

We also don't shy away from controversial and difficult topics like why should someone accept Judaism as a valid way to live life, is religion nonsense, and what to do when ethics comes against your financial interests. 

What You’ll Learn:

• How Jewish teachings influence business ethics and leadership
• Why faith and spirituality can guide smarter business decisions
• The role of self-improvement in entrepreneurship
• Balancing profit, purpose, and personal values
• Lessons from Josh’s own journey as a Jewish entrepreneur

If you’ve ever wondered how to bring faith, meaning, and values into your professional life, this episode is packed with wisdom and inspiration.

YouTube video version

About Rabbi Josh Kaller

Rabbi Kaller is the Managing Director of Olami Toronto where he leads a team of 10 in the mission of educating young Jews to engage with their Jewish heritage and become great leaders. He is also an executive coach to some of the most successful entrepreneurs in Toronto.

He maintains his boutique real estate development shop focused on South East Florida and is practicing law in Florida as well, mainly for the family business.

Connect with R. Kaller

LinkedIn 

Learn more about Olami and its programs here

Explore Judaism

R. Dovid Gottlieb (referenced in the show)