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Every entrepreneurial journey will result in either profit or pivot. In this podcast, I sit down with top-tier founders, VCs, & innovators to uncover the critical decisions that fueled their massive success. We dive deep into their journeys, exploring practical strategies you can apply. Each episode delivers actionable advice & inspiring stories designed to motivate & empower you on your own path. My mission? To decode the art of successful decision-making better than anyone in the world. Rated the #1 podcast in the world (by my mom).
Episodes
2 hours ago
2 hours ago
1 hr 2 min
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, then explains his next bet: combining world models, continual learning and LLMs to operate businesses with no human involvement.
Matan challenges him on the practical questions: Why couldn’t OpenAI or Anthropic build this? What would prove the technology actually works? And if AI handles the operations, what happens to employees?
The conversation ends with a spirited disagreement about universal basic income, human creativity, consciousness and the path to artificial general intelligence.
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EPISODE PARTNER - pulsefx.com
PulseFX is a Canadian foreign exchange and global payments consultancy that helps private clients and small‑to‑medium businesses move money across borders more efficiently. The firm focuses on reducing hidden FX costs, improving exchange rates, and helping clients manage currency risk when dealing with international real estate, suppliers, or global revenues. PulseFX combines modern payment technology with hands‑on, human guidance so clients can make better decisions when moving large sums internationally
Get 25% off your FX today by visiting my link:
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ABOUT THE GUEST
Sam Pasupalak previously co-founded Maluuba, an AI research lab acquired by Microsoft for $160M, where he worked alongside Turing Award winners Yoshua Bengio and Richard Sutton to build foundational deep learning technology.
Sam is now building Skyfall to solve the hardest open problems in frontier AI: long-horizon planning, data inefficiency, and brittle performance in dynamic real-world environments. To achieve the team's vision of a completely autonomous enterprise, the team is developing a next-generation frontier model using Continual Learning and World Modeling. The team spans San Francisco, Toronto and Bangalore, working at the intersection of world modeling, continual learning, and autonomous systems.
Connect with Sam
X: https://x.com/spisallyouneed
LinkedIn: https://www.linkedin.com/in/sam-pasupalak-57b4a220a/
Learn more about Skyfall
https://www.linkedin.com/company/skyfallai/
https://skyfall.ai/ S
kyfall AI is buying SaaS businesses for up to $1million to automate them. Those interested should reach out to their team at contact@skyfall.ai to submit their business.
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ABOUT THE SHOW
The Profit or Pivot Podcast features candid conversations about building businesses, investing and the decisions that shape both. Subscribe for more conversations with founders, operators and investors.
JOIN THE CONVERSATION
Would you trust AI to run your business? What’s the first decision you would, and wouldn’t, delegate?
Aug 27, 2026
Aug 27, 2026
52 min
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.
But Yishay's story goes much further than Platterz.
Over a 30-year career in technology, he helped build and scale companies through the dot-com era, the 2008 financial crisis and COVID. Along the way, he worked with companies including Angry Birds and Candy Crush and helped build another business that was acquired for $240 million.
After October 7th, Yishay decided to make another major change.
The attacks affected his family personally. His wife landed in Israel that morning, his nephew was at the Nova festival, his cousin was taken hostage, and a close friend's son was killed. Eventually, Yishay decided there was something more important he wanted to do with the next chapter of his career.
Today, he runs Clarim Ventures, investing in Israeli technology companies and helping Israeli founders access North American capital and relationships.
In this conversation, we discuss:
- Building a $100M business and watching revenue disappear
- Why Yishay refused to quit
- Angry Birds, Candy Crush and the early mobile internet
- The impact of October 7th on his family
- Why he believes Israeli entrepreneurs are different
- Why he's investing his capital in Israel
- What's gone wrong with Canada's economy and tech ecosystem
- Why he thinks founders shouldn't expect a 9-to-5
- The biggest lessons from 30 years as an entrepreneur
This is a conversation about entrepreneurship, resilience, Israel, Canada, success, failure and what actually matters after decades of building companies.
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EPISODE PARTNER - pulsefx.com
PulseFX is a Canadian foreign exchange and global payments consultancy that helps private clients and small‑to‑medium businesses move money across borders more efficiently. The firm focuses on reducing hidden FX costs, improving exchange rates, and helping clients manage currency risk when dealing with international real estate, suppliers, or global revenues. PulseFX combines modern payment technology with hands‑on, human guidance so clients can make better decisions when moving large sums internationally
Get 25% off your FX today by visiting my link: www.thatfxguy.com
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ABOUT YISHAY WAXMAN
Yishay's tech career began in 1996 in Israel, where he sold voicemail, SMS and ringtones to Telecom companies in over 85 countries. In 2005, Yishay co-founded Jumptap, one of the leading mobile advertising platforms, a company that spanned Boston and Israel, achieving revenues of $100M +, employing over 300 people, and culminating in a $240 million exit. In 2015, he co-founded Platterz, now known as Thriver Inc., which grew to over 200 employees and reached a $100 million run rate pre-COVID before being acquired by Gusto in 2024. Today, Yishay is laser focused on his 2 funds Clarim Ventures, a seed-stage fund backing the next generation of Israeli AI companies & Triple Threat Partners exclusively investing in the top Israeli cybersecurity companies.
Reach out to Yishay:https://www.linkedin.com/in/yishaywaxman/
Learn more about Clarim VC
Jul 21, 2026
Jul 21, 2026
51 min
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 brand from scratch.
What started as frustration during pregnancy became a luxury slipper company backed by investors, featured on Dragons' Den (getting a deal with 2 Dragons), and built around premium manufacturing, thoughtful branding, and obsessive product design.
We also discuss one of the most overlooked parts of fundraising: choosing the right investors.
We cover:
- Why consumer startups are so difficult to build
- Why founders should be careful who they take money from
- Dragon's Den behind the scenes
- Building a luxury brand customers actually trust
- Building a business while raising a family
- Why Canada is such a difficult place to build startups
Whether you're a founder, investor, or simply interested in how great brands are built, this episode offers an honest look at entrepreneurship beyond the headlines.
THIS IS NOT SPONSORED by Mave & Chez but they graciously offered a promo code to our viewers:
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Jun 18, 2026
Jun 18, 2026
42 min
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 was elected to the Federal Parliament in 2025 as the Member of Parliament for York Centre. Not only was York Centre the only Toronto riding won by the Conservative Party of Canada, but he also successfully flipped the seat from the Liberals.
Roman is one of those rare politicians that acts from principal rather than political expediency. And in this conversation he doesn't hold back:
- Carney's failed economic agenda
- The rise of anti-Semitism
- Immigration
- DEI
And many other important topics...
Watch on YouTube
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EPISODE PARTNER - pulsefx.com
PulseFX is a Canadian foreign exchange and global payments consultancy that helps private clients and small‑to‑medium businesses move money across borders more efficiently. The firm focuses on reducing hidden FX costs, improving exchange rates, and helping clients manage currency risk when dealing with international real estate, suppliers, or global revenues.
PulseFX combines modern payment technology with hands‑on, human guidance so clients can make better decisions when moving large sums internationally
Get 25% off your FX today by visiting my link: www.thatfxguy.com
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ABOUT ROMAN BABER
Roman Baber is the Member of Parliament for York Centre, located in North York. He is a member of Parliament’s Standing Committee on Justice and Human Rights.
Roman previously represented York Centre in the Provincial Legislature from 2018 to 2022.
Roman is a lawyer, called to the Ontario Bar in 2006 and until his election to the Provincial Legislature in 2018, practiced commercial and insurance litigation. He attended high school at W.L. Mackenzie, obtained a B.A. from York University and graduated law school at Western.
Roman was born and lived in the Soviet Union until age eight. He moved with his family and lived in Israel until age fifteen. In 1995 along with his family, Roman immigrated to Canada, directly to the heart of York Centre at Bathurst & Sheppard. Roman is an avid fan of the City of Toronto, subways and the Raptors.
Apr 22, 2026
Apr 22, 2026
51 min
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 to focus entirely on Israel advocacy, bringing his understanding of media, distribution, and narrative to a much bigger fight.
⚔️ What We Get Into
- Why Israel is losing the PR war
- Why facts don’t change minds anymore (and what does)
- Where criticism of Israel crosses into antisemitism
- Why antisemitism keeps resurfacing across generations
- Why Hillel believes things could get much worse for Jews in the West
- His perspective on figures like Donald Trump and shifting global alliances
- The story of being banned from Australia for 3 years
- Why Israel punches far above its weight in startups
- The cultural mindset that drives innovation
- Lessons founders everywhere can learn:
🎧 Watch on YouTube
EPISODE PARTNER - pulsefx.com
PulseFX is a Canadian foreign exchange and global payments consultancy that helps private clients and small‑to‑medium businesses move money across borders more efficiently. The firm focuses on reducing hidden FX costs, improving exchange rates, and helping clients manage currency risk when dealing with international real estate, suppliers, or global revenues. PulseFX combines modern payment technology with hands‑on, human guidance so clients can make better decisions when moving large sums internationally
Get 25% off your FX today by visiting my link: www.thatfxguy.com
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ABOUT HILLEL FULD
Hillel is a technology journalist, global speaker, and startup marketing advisor. Forbes called Hillel, “The man transforming Startup Nation to Scale-up Nation”, and Hillel was also named Israel’s top marketer, and among the 100 most influential social media personalities worldwide.
For over a decade, Hillel helped technology companies on their journey from idea to revenue and collaborated with leading companies including Google, Microsoft, Oracle, and many others. Hillel also wrote about the Israeli technology ecosystem for publications including TechCrunch, Inc Magazine, FastCompany, and more.
On October 7th, all that changed, and Hillel made an immediate decision to shut down his consulting business and refocus his time and energy on defending Israel online given the atrocities of that day and the spike of antisemitism that followed. Since October 7th, Hillel’s content has reached several billion impressions across his various platforms on which he has hundreds of thousands of followers.
Hillel has also spoken to audiences around the world about topics including Israeli innovation, marketing, entrepreneurship, and most recently, about the war and Israel’s ongoing military and geopolitical challenges.
You can read more about Hillel at HillelFuld.com and follow him across social media at the screen name @Hilzfuld where he shares his take on various topics pertaining to Israel and the future of western civilization.
Mar 31, 2026
Mar 31, 2026
8 min
Anti-Semitism is an evil and accelerating phenomenon around the world.
I break down my thoughts on its root causes.
Mar 18, 2026
Mar 18, 2026
1 hr 8 min
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 only focuses on the top fraction. Most are rejected in minutes. Not because the idea is bad, but because the founder didn’t know how to present it.
We get into the mechanics of fundraising, what actually gets an investor’s attention, and why most founders lose before the first meeting even happens.
We go deep into:
- What actually happens when your deck hits a VC inbox
- Why first impressions (deck + outreach) decide everything
- The 3-slide framework every pitch deck should follow (and why most get it wrong)
- Why unrealistic market sizes instantly kill credibility
- How VCs think about market size, growth, and scale
- The biggest mistakes in cold outreach (and how to actually get responses)
- The real reason most founders never get funded
Jeff also breaks down something most people ignore:
Fundraising isn’t a side task. It’s a full-time job. Done properly, it requires structure, consistency, and hundreds of touchpoints, not a few warm intros and a pitch deck.
If you’re a founder trying to raise capital, break into VC, or just understand how competitive this game really is, this episode is a reality check.
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EPISODE PARTNER - hiredonna.com/matan
Find elite offshore executive assistants to help you grow your business or manage your increasingly busy life. Donna's assistants go through a 6-week paid intensive academy, ensuring that only the past are matched with employers. Only 1/400 applicants pass their filters, tests and academy.
My listeners get 30% off for the 1st three months when you tell them I sent you (or use my link above).
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About Jeffrey Fidelman
Jeffrey is an investment banker & entrepreneur with 10+ years of experience advising early-stage companies and emerging investment managers. He is the Founder & Managing Partner of Fidelman & Co., a strategic advisory firm launched in 2015 to help founders & fund managers prepare for & execute capital raises with discipline, clarity, & data-driven strategy. At Fidelman, Jeffrey has advised hundreds of startups & emerging managers across technology, fintech, healthcare, & consumer sectors. The firm specializes in fundraising strategy, investor targeting, financial modeling, valuation, and execution support through its Fundraise as a Service (FaaS) platform, which combines structured processes with real-time investor intelligence.
Prior to Fidelman, Jeffrey held senior roles at Morgan Stanley and HSBC, where he gained experience across capital markets, portfolio management, & revenue strategy. Earlier in his career, he was involved with venture investing, providing him with an operator-level perspective on early-stage growth and capital formation. Jeffrey graduated cum laude from Harvard University & is frequently sought out by founders for his practical, execution-oriented approach to fundraising and investor readiness.
Connect with Jeff:
Jeff's Services
Fundraise as a Service (FaaS) is a structured, execution-driven approach to raising capital. It replaces ad-hoc outreach with a disciplined framework—covering investor targeting, messaging, materials, and follow-ups—so founders can run a repeatable, professional fundraise while staying focused on building their business.
FundEx is a purpose-built fundraising operating system that powers modern capital raises. It centralizes investor intelligence, outreach workflows, pipeline tracking, and performance analytics into a single system of record. Designed to bring structure and accountability to fundraising, FundEx enables founders and fund managers to manage their raise with the same rigor as sales or operations—turning fundraising from a fragmented process into a measurable, scalable operating function.
Feb 26, 2026
Feb 26, 2026
50 min
Episode Partner - hiredonna.com find elite executive assistants (use my link below for discounts)
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 relationships the same way companies compound capital.
But the deeper insight is this: VCs are also fundraisers.
Every venture firm answers to limited partners. They raise funds, demonstrate performance, defend strategy, and differentiate in a crowded market. That means every investment is not just a bet on a founder, it’s a bet that must be defensible to institutional capital.
Founders who understand this dynamic immediately gain an edge.
In this episode, we break down how venture capital actually works. If you’re building a company or allocating capital, this conversation will sharpen how you think about incentives, access, and positioning.
What We Cover:
- Why breaking into venture “circles” is hard and why that’s rational
- The role of trust and pattern recognition in writing checks
- Why cold outreach rarely works the way founders expect
- The structural reason VCs favor repeat founders
- How LP dynamics shape every investment decision
- Why founders who understand fund math raise capital faster
- The real alignment (and constraints) between founders and investors
EPISODE PARTNER
Find elite offshore executive assistants to help you grow your business or manage your increasingly busy life. Donna's assistants go through a 6-week paid intensive academy, ensuring that only the past are matched with employers. Only 1/400 applicants pass their filters, tests and academy. My listeners get 30% off for the 1st three months when you tell them I sent you (or use my link above).
My link: hiredonna.com/matan
ABOUT WINTER & COOLWATER
Winter Mead is the Founder and Managing Member of the investment firm Coolwater Capital, which exclusively focuses on emerging managers and technology investments. Coolwater is an academy for training, building and scaling emerging managers, a curated community of VC investors and early-stage investment specialists, and an investment firm. Coolwater has helped launch over 300+ emerging managers in the last four years, establishing strong ties and trust with these managers, who form the foundation of the Coolwater community. Coolwater has made over 90 investments into its accelerator ecosystem supporting the next generation of founder investors and new technologies.
Winter is also the author of "How To Raise A Venture Capital Fund" and an upcoming book, "How To Set Up A Venture Capital Fund." Prior to Coolwater, he played a key role in an evergreen investment fund at SAP and co-founded the LP transparency movement called #OpenLP. Winter's extensive experience includes private equity and venture capital roles in San Francisco, institutional fund investments, direct technology investments for SAP, and angel investing. He also served as junior faculty at Stanford Graduate School of Business, holding degrees from the University of Oxford and Harvard University, and now resides in Utah with his family, passionately solving business challenges.
Connect with Winter on LinkedIn
Learn more about Coolwater