🏠 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) Timestamps  00:00 Introduction 03:38 Interest in Judaism 06:38 Becoming religious  10:51 Importance of Shabbat in business 12:54 Is religion true? 17:13 Challenging the arguments for Judaism 22:53 Controversial topics in the Bible 27:56 Going to Jewish seminary (Yeshiva) 31:10 Running a nonprofit 34:50 Are people "good" or "bad"? 37:38 Practical spiritual advice for business 39:39 The EQI model 42:16 Prayer  44:25 Advice for struggling entrepreneurs  48:49 Creating a "power phrase"  51:40 Book recommendations 

Timing is everything when building a startup. It can make the difference between a billion dollar exit and utter failure. Its why one of the most important questions a venture capital investor will ask startups is "why now". What changed about the market that allows you to create significant value and build a hyperscale business NOW. Michael Durance of xiVentures joins me to discuss his successful career in big tech, building successful startups, and VC investor. A theme that runs through our discussion is how market timing impacted his decisions, and how it made building a successful business relatively easy. And how poor timing almost destroyed another. In 1 case, good timing resulted in a +$1 billion exit. And in another case, poor timing resulted in disaster. Michael shares important lessons in how to manage some of the market forces, developments in tech external to your business, and macro conditions are outside our control BUT have a substantial impact on our business. We also discuss his decision to become a VC, how he invests as a former operator, and his investment criteria. This is a truly special episode with a lot of learnings for aspiring entrepreneurs. You won't want to miss it! Michael's LinkedIn xiVentures 

How do billionaires really manage their money? What’s the difference between creating wealth and actually preserving it across generations? In this episode of The Profit or Pivot Podcast, I sit down with Mo Lidsky, a serial entrepreneur, author of five books, and co-founder & CEO of Prime Quadrant, a leading family office advisory firm serving over 250 ultra-high-net-worth families with more than $23B in assets under advisement. Mo’s entrepreneurial journey started at just 17 years old, when he launched his first business by accident and sold it two years later for hundreds of thousands of dollars. Since then, he’s built and exited multiple companies, and today helps some of the wealthiest families in the world navigate wealth management, investing, and legacy planning. In this episode, we cover: Mo’s entrepreneurial journey and lessons from multiple exits How family offices work and why billionaires use them The biggest mistakes wealthy families make when managing wealth Insights into the venture capital and private equity landscape The mindset and ingredients behind building a successful business If you’re an entrepreneur building your first startup or preparing for an exit, an investor curious about how the ultra-wealthy think, or simply interested in the world of family offices and generational wealth, this episode is packed with insights you won’t want to miss. _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ About Mo Lisdky Mo Lidsky is the Chairman and CEO of Prime Quadrant, advising over 250 ultra-high-net-worth families representing more than $23B in assets. A serial entrepreneur, he has built, bought, and sold companies across sectors from education and e-commerce to auto restoration and microfinance. Passionate about philanthropy, Mo chairs the Prime Quadrant Foundation and has served on the boards of leading hospitals and universities in Canada and Israel. He is also the author of five books on wealth, investing, philanthropy, and relationships, and a frequent speaker on issues affecting affluent families. Mo holds multiple degrees from Yeshiva University, an MBA from the University of Toronto, and a PhD from Apsley Business School. Above all, he is most proud of his role as husband and father to five children. Mo's books Learn more about Prime Quadrant 

Entrepreneurs focus on how to create wealth but most DON'T think about the day after exit. How do they use their wealth, plan for the future, protect their legacy, and invest in their community. Mark Halpern, the Founder of WEALTHinsurance.com, became the most famous insurance broker in Canada by focusing on answering these questions for Canada's most successful business leaders. In this episode, we dive into Mark's journey from aspiring journalist, middling insurance broker at a large agency, to one of Canada's top life insurance providers (and its most famous). Today, his clients include successful business owners, professionals and ultra wealthy families. Mark helps them preserve their wealth and pay less tax using "strategic philanthropy" by converting taxes to charitable gifts. For example, he shares a great story how he helped his client book a $1 million donation to a hospital immediately by ONLY paying a few thousand every year for life insurance. This was a win for his client's business because his peers, customers and colleagues saw him as incredibly charitable (which he is). Surprised something like this is possible. So was I! Mark shares insight into how he found his niche that enabled him to stand out in a crowd of 30,000 insurance brokers who nominally offer similar services. And, after finding his niche, how he bucked traditional sales and marketing tactics to become the most well known life insurance broker in Canada. And even more important, he discusses how to live a well balance, meaningful life, without compromising his financial and business ambitions. Mark's opinions and insights are frequently published on TV, radio, podcasts and written media. His expertise as a keynote speaker is sought after for conferences and conventions, earning him at least $10,000 per engagement, all of which are donated to charity. His insights, advice, and perspective is valuable for any aspiring entrepreneur and successful entrepreneur. You don't want to miss this episode!   Connect with Mark & learn more about his services: Mark is a thought leader in Canada’s Life Insurance, Estate Planning and Philanthropy communities. He has mentored dozens of insurance advisors and developed a one-of-a-kind mentoring/coaching program. Website  LinkedIn  Coaching & Mentoring Program  “The New Philanthropy” Mark’s Ted Talk  Mark’s Sizzle Reel that explains what he does    DISCLAIMER: This is not paid promotion. I've known Mark for over 15 years and consider him a mentor. I think he is one of the most successful entrepreneurs in the "boring" business category in Canada and believe my audience can benefit tremendously from listening to his perspectives and considering using his services.

Should you leave your steady corporate job to start a business? In this episode of The Profit or Pivot Podcast I speak with Talia Abramowitz, a partner at Deloitte, the largest professional services firm in the world ($70B in revenues) and the founder of Deloitte Ventures, a $150 million corporate venture capital fund. Talia shares how she carved out entrepreneurial opportunities within the corporate giant, built a 500-person AI practice from scratch, and what it really takes to launch a corporate venture fund. Whether you're a founder raising capital, an investor seeking insight into CVC strategy, or a corporate leader itching to innovate from within, this episode is for you. 🔍 Topics We Cover: Why she chose to stay in corporate despite wanting to be an entrepreneur How Deloitte Ventures was created and what it looks for in startups Why Canada’s venture ecosystem lags behind (and how to fix it) Evaluating founders and spotting red flags during diligence When to quit your job to build a business Is a modern university degree useless 💬 Question for You: Are you debating whether to stay in your job or start your own thing? Drop a comment, let's talk about it. 📢 Subscribe for more conversations with leaders who built, pivoted, and profited. Want to watch the video version? Check it out on YouTube. _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ About Talia Talia is the Managing Partner of Deloitte Ventures, a $150M corporate venture fund focused on emerging tech companies. She helped launch the fund in 2022. A 20-year Deloitte veteran, Talia previously served as the COO for Deloitte’s Financial Advisory practice and for Omnia AI, the firm’s artificial intelligence practice which she helped build into a ~$100M business. Talia has more than a decade of experience providing valuation and M&A advisory services. Connect with Talia here  

Mark Nashman shares his journey from successful entrepreneur to successful venture capital investor. We learn about Mark's incredible story building Clarity Systems, a financial software business that he grew to over $50 million in revenues before selling to IBM. We also discuss Mark's perspective on investing in startups, what he looks for, red flags and some advice for entrepreneurs. Mark is a rarity amongst entrepreneurs today. He never relied on huge financing rounds to build his business. His insights into finding product market fit, building a business, and decision to sell will be helpful for any startup founder. Connect with Mark on LinkedIn  Incapital Ventures INcapital Ventures invests in early growth-stage technology companies primarily from Israel, with an established product market fit and solid traction and operations in North America. Our reputation as “bridge builders to the North American market” provides us access to exclusive and attractive opportunities in Israel.

In this episode of The Profit or Pivot Podcast, I sit down with Sonya Meloff, co-founder of one of Canada’s most successful sales recruitment agencies. She helped thousands of companies, from startups to enterprises, hire top-performing salespeople and scaled her business to 8-figure revenues before exiting. If you're a founder hiring your first sales rep, scaling your go-to-market team, or just want to sharpen your sales skills, this is a masterclass. We dive deep into: Sonya’s accidental entry into sales and how she became a natural closer Her time at Monster.com and what it taught her about digital disruption and sales culture The moment she walked away from a multi six-figure salary to start her own firm and landed her first client before leaving the office Her unique methodology for hiring top sales talent What every founder needs to know before hiring their first salesperson The #1 trait she looks for in every sales hire How to sell anything by asking the right questions and reframing the value Handling rejection, founder-led sales, and why everyone is in sales whether they know it or not 💡 Whether you’re a founder hiring your first SDR, a sales leader building a team, or just trying to sharpen your own sales skills, Sonya delivers real, battle-tested insight from the front lines. Video version on YouTube _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ ABOUT SONYA Sonya Meloff is a Canadian entrepreneur and sales recruitment expert, best known for co-founding Sales Talent Agency Inc., a leading sales recruitment firm specializing in hiring sales professionals. Since founding the agency in 2007, she has helped thousands of companies, from early-stage startups to global enterprises, hire top-performing sales talent. In 2024, she sold her shares in the business to her co-founder and is now actively exploring new entrepreneurial endeavours. Sonya holds a Bachelor of Arts in Political Science from the University of Calgary. She began her career with Hays in London, England, before returning to Canada to take on leadership roles in sales. As Director of Enterprise Sales at Monster Canada, she helped grow the company’s revenue significantly and became the youngest and first female recipient of Monster’s Salesperson of the Year award. In addition to co-founding The Great Canadian Sales Competition, which became Canada’s largest student competition, she also co-founded Salesclass, a leading global sales reskilling program that has successfully trained 500+ Sales Development Representatives. Sonya is a recognized mentor, speaker, and mother of three, known for balancing business leadership with a strong commitment to family and community. CONNECT WITH SONYA  Linkedin  

In summer of 2020, at the peak of chaos in the healthcare industry, Michael raised a venture capital "Seed" round for his healthcare software startup. How did Michael turn a crisis into an opportunity, grow his business, and set himself on the path to success? Some of the topics covered: Michael's background, how and why he started Verto How he developed an innovative solution in healthcare that few people could create and implement How Michael adapted, grew, raised money and thrived as a healthcare software when customers stopped buying new software during a pandemic When to pivot, and when to pivot back Managing a remote workforce Building a mission driven business and a strong company culture Staying mentally healthy About Verto Verto has developed a Digital Twin Platform for healthcare that uses smart integrations to stitch data from multiple health data sources together to create a truly interoperable technology to bring every patient to their best possible health outcome. https://verto.health/

In this episode of The Profit or Pivot Podcast, host Matan Hazanov interviews Brice Scheschuk, a trailblazing entrepreneur who co-founded Wind Mobile and sold it for $1.6 billion. Bryce takes us behind the scenes of his journey, from his early days in Saskatchewan and the naval reserve to disrupting Canada’s telecom oligopoly with Wind Mobile. He shares heart-pounding moments, like securing a $200M deal with an Egyptian billionaire just days before a critical deadline and navigating a near-bankruptcy crisis that led to a massive exit. Now a seasoned investor with stakes in 50 venture funds and 130 direct startup investments, Bryce reveals why he’s jaded about the venture capital ecosystem and offers a refreshing perspective with his “Play Your Own Game” philosophy. He also shares practical advice for founders struggling in today’s tough market, focusing on resilience, mental health, and staying laser-focused on product-market fit. This episode is a must-listen for entrepreneurs, investors, and anyone looking to build a sustainable business in a noisy world. What You’ll Learn: How Bryce hired 1k employees in 1 year to reach a million customers Lessons from hyper scaling a company The high-stakes drama of raising capital and scaling a telecom giant Why Bryce believes the VC model is broken for most Canadian founders Actionable strategies for founders to build resilient, customer-focused businesses The importance of mentorship and mental health in entrepreneurship _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ ABOUT BRICE Brice is the Managing Partner of Globalive Capital (www.globalive.com). He was a co-founder and CFO of WIND Mobile as well as CEO of Globalive Communications. Brice has over thirty years’ experience building and operating companies at Globalive, WIND Mobile, Leitch Technology and PricewaterhouseCoopers. He obtained his CPA, CA designation at PricewaterhouseCoopers and B.Comm (Hon.) Finance from Dalhousie University. Brice served as a Maritime Surface Officer in the Royal Canadian Naval Reserve. Brice serves on numerous boards and advisory committees (public, private, and not-for-profit) and is a frequent speaker on scale-up entrepreneurship and innovation. He is a co-founder of MindFrame Connect (www.mindframeconnect.com), a not-for-profit focused on elevating the craft of mentorship, improving entrepreneurial resiliency and alternative capital paths to venture capital. Brice is a supporter of Build Canada (www.buildcanada.com). His interests include Canada’s innovation and start-up ecosystem, entrepreneurial finance, mentorship excellence, resiliency, financial literacy, political moderation/centrism, military veteran transition, fitness, travel, good food, good books, and great friends.   _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ Connect with Brice: Globalive LinkedIn X Mindframe Connect 

Avi Abrams shares his journey from aspiring VC to one of the 1st hires in a high growth startup raising $50 million, and how he eventually leaves to pursue his goal of building a business from 0 to 1.

In this episode, Matan Hazanov sits down with Igor Sorokin, the marketing mastermind behind One Core Media, an 8-figure boutique marketing firm driving results for global giants like Canadian Tire, Kijiji, Cisco, and even Floyd Mayweather.

Chris Carder shares his incredible journey as an aspiring journalist to successful entrepreneur, academic, and builder of startups at scale.

Join host Matan Hazanov for an incredible discussion with Allen Lau, co-founder of Wattpad, the global storytelling platform that sold for an astounding $660M USD.

On October 7, 2023, Israel was brutally attacked by Hamas terrorists resulting in the worst single day massacre of Jewish people since the Holocaust. With the country now at war, how does civil society cope with 10-15% of its labour force being called up to military reserve duty? David Shore, a Partner at OurCrowd, the most active venture capital investor in Israel joins me to discuss the situation in Israel and how startups he invested in continue building and succeeding. Israel is one of the largest startup ecosystems in the world, consistently punching above its weight given its small population and hostile neighbours. For context, in Q4 2023, VC investments in Israel were US$1.4 billion compared with Canada's ~$1.1 despite being in the middle of a war and having only 1/4 the population. In this episode, we delve into David's journey from an equity analyst on Bay Street (the Canadian Wall Street) to venture capitalist. David has decades of experience analyzing, supporting, building and investing in startups. His insights into what is required for success is invaluable for any entrepreneur. We also discuss what Canadian entrepreneurs can learn from their Israeli peers. We address the war, learn how Israeli startups are managing, and discuss how those lessons can be applied in Canada and elsewhere. Video version: https://youtu.be/DS-YpFb9h0M