In this conversation, Karim breaks down how the rules of building and investing in startups are changing - fast.

In this conversation, we explore how founders, investors, and operators can navigate a market where traditional venture funding has slowed, IPO timelines have stretched, and liquidity has become harder to access.

Naseem shares how his team is identifying overlooked companies - profitable, growing businesses that no longer fit the venture hype cycle - and helping them access public markets in a different way.

We also unpack:

• What an “independent sponsor” actually does
• Why mid-market companies are stuck in today’s funding environment
• How public markets differ from private capital
• What makes a company a strong SPAC candidate
• The future of Canadian companies accessing U.S. capital markets

Ghassan Halazon, Founder and CEO of EMERGE Commerce, joins the StartWell Podcast for a candid conversation about what it really takes to build and operate e-commerce businesses at scale. From his early days leaving Wall Street to launch one of Canada’s biggest daily deals businesses, to building EMERGE into an e-commerce brand portfolio, Ghassan shares hard-won lessons from acquisitions, public markets, debt, restructuring, and the discipline required to survive volatile markets.

This episode digs into the reality behind e-commerce rollups, why diversified portfolios can break down in consumer businesses, and how EMERGE refocused around fewer, stronger verticals. Ghassan also explains why brand loyalty, community, and customer trust matter more than ever - and why most people should think twice before launching “just a nice little e-commerce store.”

Partnerships are no longer a side function - they’re becoming one of the most important growth channels in modern B2B.

In this episode of the StartWell Podcast, Chris Lavoie - founder of Partnership Mastermind - breaks down why partnerships are having a resurgence, what most companies get wrong when building partner programs, and how partner professionals can ramp faster with better training, community, and real-world practice.

Ben Wise and Darren Chiu are the founders of Captivate - a newsletter and training platform that turns behavioral science into practical tools for persuasion, communication, and change. In this conversation, we dig into the line between ethical persuasion and manipulation, why emotion drives decision-making more than logic, and how leaders can use simple tactics to run better meetings and offsites.

If you plan internal offsites, sales kickoffs, or team gatherings, this episode is a playbook: how to prime people before they arrive, how to open the day so you don’t lose the room, and how “labeling” emotions can instantly reduce tension and increase buy-in. We also explore persuasion in advertising, why small conversion lifts matter at scale, and how AI is best used as a thought partner - not as your voice.

Joseph Fung is a 5x founder and CEO with a simple obsession - building places where great people can do their best work.

In this conversation, Joseph walks through the real arc of entrepreneurship: bootstrapping companies to the brink, learning how exits actually happen, and why the hardest part isn’t 0-to-1 - it’s building something with longevity. We dig into his journey from an early white-label CMS business (built while in engineering at Waterloo) to TribeHR’s acquisition, and the lessons he learned inside a much bigger machine afterward.

Then we get into the messy reality of workforce development and talent - why most companies underinvest in employee growth, why “culture” only matters if it speeds up decisions under stress, and why software companies live or die by alignment and knowledge transfer.

We also unpack Uvaro’s pivot from tooling to outcomes, the challenge of government procurement cycles, and how 2025’s macro uncertainty created a sudden squeeze between banks and delayed contracts.

And yes - after shutting down a 60+ person company, Joseph went to China for two months of Shaolin-area kung fu training to reset his body, his mind, and his relationship with productivity.

Max Tremaine is the cofounder and CEO of Sherpa - the travel infrastructure company helping millions of travellers every week understand what they need to cross borders, apply for eVisas as an add-on inside travel bookings, and validate documents for airlines and travel operators.

In this conversation on the StartWell Podcast, Max breaks down how a painful personal travel problem turned into a global B2B platform - and why the travel world is shifting from “visa-free” to “pre-clearance everywhere” (eVisas, ETAs, and arrival systems). We also dig into the COVID-era inflection point that helped Sherpa scale from a couple airline integrations to dozens, the realities of selling into airlines and travel ecosystems, and why “hiring a bunch of people” is rarely the shortcut founders think it is.

We also get practical about AI - not as hype, but as a real operational advantage. Max shares how Sherpa uses LLMs to spot changes in government systems earlier and reduce response times from weeks to hours, while still keeping humans accountable for architecture and trade-offs.

We talk about Collin’s book, The Terrifying Art of Finding Customers, and why he wrote it in the first place: he didn’t want to regurgitate another “sales development playbook.” Instead, he wanted to name the part founders don’t want to face - that the hardest, most terrifying work isn’t outreach. It’s discovering whether a real, urgent, expensive pain actually exists in the market.

Collin shares the classic founder failure mode in one phrase: “show up and throw up” - demoing everything you built before you’ve earned the right to talk about solutions. He learned this the hard way building Voltage CRM: plenty of people told him the idea was “cool,” then none of them would pay. That mistake becomes the foundation for the book’s thesis: the deeper the pain and dissatisfaction you uncover, the easier selling becomes downstream.

Then comes the proof point that reframed everything for him: product-market fit strength is a multiplier. Collin tells the story of running campaigns for Uber and seeing performance so extreme it couldn’t be explained by tactics alone - it was demand. From there, we explore product-market fit as a spectrum (not a checkbox), and how founders confuse product-customer fit with product-market fit - finding “Bob,” the one buyer who loves you, instead of a market that needs you.

We finish with practical selling discipline (buyer-verified pipeline stages, MEDDICC-style qualification), plus where AI actually helps today: research, signals, and internal enablement - not mass-generated messaging.

In this episode, Christine Song (Founder, 529 Society) breaks down why big conference rooms and name tags don’t create real relationships - and why she believes leaders need a third space outside of work to talk honestly, pressure-test decisions, and build trust without politics.

Christine shares how a single LinkedIn post led to 600 applicants in 30 days, why she chose to keep 529 Society intentionally small (and vetted), and how she designs intimate, high-trust dinners and operator-founder-investor cohorts across Canada. We also dig into what founders often miss when they only spend time with other founders, how “character” becomes a business advantage, and why IRL connection is becoming more valuable as online trust erodes.

If you’re a founder, exec, operator, investor, or builder who’s tired of performative networking and wants a more real peer network - this one will land and you'll probably want to join her community.

The conversation starts by untangling a common misconception: PR is not a guaranteed lead machine. Katie positions PR clearly in the brand awareness and reputation bucket. One launch or one media hit won’t move the needle on its own. Instead, PR is about showing up consistently in the right places so your market becomes familiar with you—and that familiarity compounds into trust.

AI has changed the game too. Drafting a press release or basic content can now be done with tools like ChatGPT, but that only gets you part of the way. The real value of an agency lies in strategy and execution: crafting the right angle, timing the announcement, pre-pitching journalists, and tying earned coverage into broader marketing and paid efforts.

Katie also talks about the rise of founders as media channels. People often discover a company through its leaders first, so she walks through how to choose your thought-leadership pillars and pick formats that suit you—whether that’s video, newsletters, op-eds, or podcasts.

Through a case study with insurtech entrepreneur James Benham, Katie shows how long-term PR, speaking, and owned content can help a founder successfully enter a new vertical and become a recognized authority.

The episode closes on a powerful theme: treat content as a sales and relationship engine, not just a broadcast. Repurpose every shoot, test formats using data, and think like an investor about where your time and marketing dollars go.

We discuss challenges he faced in the financial landscape, the importance of data in making financial decisions, and the need for localized solutions in Canada. 

The conversation also touches on the supportive startup ecosystem in Canada and the future of Float as it continues to innovate and expand its offerings!

We discuss the impact of economic downturns, particularly the 2008 financial crisis, and the lessons learned from such experiences. 

Peter emphasizes the importance of resilience, community support, and understanding market trends in building successful businesses. He also introduces his venture advisory studio, which aims to support startups in navigating the complexities of entrepreneurship. 

The talk includes a discussion on rising costs of living in Canada and the implications for individuals and entrepreneurs. 

Peter's passion for solving problems he sees in the grocery business setup the motivation for founding a company called Tre'dish and we discover why he's excited to still be an entrepreneur - years after finding success through exits from previous ventures.

Expect to hear Josh and StartWell founder/CEO Qasim Virjee share their personal journeys which led to work building communities, perspectives on the recent rise of online communities as marketing tools, differentiation between persona-based and company-based communities and a whole lot more.

We highlight the necessity of creating value for community members and the implications of community dynamics in the future of work. We consider the importance of community in professional development - especially as the modern workplace evolves so fluidly. The conversation also delves into mentorship plus how to leverage 'content' for community engagement, integrating community into the customer journey, and the necessity of adapting marketing strategies to foster community building. We end with some recommended tools for developing communities online.

Scott Knox, President and CEO of the Institute of Canadian Agencies (ICA), discusses their "Brands Need More Canada" initiative.

Canadian agencies excel at delivering integrated campaigns with smaller budgets compared to larger markets like New York or London. This efficiency, combined with Canada's diverse workforce, makes it an ideal testing ground for global brands.

We spend a little time introducing our "Canadians Create" video podcast series, which is a StartWell production being made in partnership with the ICA. The series aims to showcase the depth of thinking and capability within Canadian agencies to a global audience - by telling the stories behind case studies of excellent Canadian creative work.

Nik discusses the company's first Toronto meetup event and shares insights about fintech ecosystems in Canada, highlighting how Canadian markets are often overlooked by US investors despite having significant potential and talent.

For their first ever Toronto fintech meetup, This Week in Fintech received 450 attendee applications - and only had 150 spots available.  Nik believes that Toronto is has a healthy fintech (and tech) ecosystem and this event proved it.

In addition to talking about his company and events, we discussed the importance of in-person connections as well as where trust can evolve in the workplace.

If you're part of fintech, or interested in this space - we recommend watching this episode and checking out Nik's website.

This isn't your typical business chat. Alistair brings an incredibly fresh perspective on why startups need to stop obsessing over product features and start focusing on what really matters - getting attention and converting it into profitable demand. He's got over 163 case studies backing this up, from clever marketing hacks to brilliant system disruptions.

What we love about this discussion is how Alistair breaks down why the timing for this message couldn't be better. With AI and cloud computing making it easier than ever to build products, he argues that distribution and marketing are now the real differentiators. You'll hear some fantastic examples, including a wild story from the 1300s about a castle siege that perfectly illustrates the power of strategic bluffing in business.

The conversation gets particularly interesting when we talk about value chain disruption and how companies like IKEA have revolutionized their industries by simply reassigning steps in their process. We also explore why startups must fundamentally disagree with the status quo - otherwise, what's the point?

The book itself is a bit of a rebel - it's got secret Morse code messages, Easter eggs, and a design that looks like classified documents. It's clear Alistair and his co-author practiced what they preach by making the book itself subversive.

Whether you're a startup founder, working in tech, or just interested in innovative business strategies, this conversation will challenge your thinking about how to stand out in today's market. Expect to walk away with a completely new perspective on what it really takes to succeed in the startup world - hint: it's not another feature update.

The discussion kicks off with a look back at Carbon6's original mission: creating the ultimate toolkit for Amazon sellers by acquiring and combining existing software solutions. But what makes this story particularly compelling is how the company pivoted and evolved. You'll learn how they transformed from a pure acquisition strategy to building their own products and fostering strategic partnerships, all while growing their revenue 7x and maintaining profitability.

The conversation takes you behind the scenes of building a unified company culture, as the founders share how they successfully integrated multiple acquired companies into one cohesive organization. There's a particularly interesting segment about their innovative technical architecture – a "central spine" that allows them to efficiently integrate new acquisitions and products.

You'll get practical insights into managing rapid growth, as the team discusses scaling to 140 employees across multiple global locations while maintaining a strong company culture. The founders are refreshingly honest about the challenges they faced, including the shift from being "guys with a dream" to running a mature, profitable enterprise growing at 100% year-over-year.

What makes this conversation especially valuable is the balance between high-level strategy and practical details. Whether you're interested in M&A, tech entrepreneurship, or the Amazon seller ecosystem, there's something here for you. The founders share specific examples of how they structured their teams, approached partnerships, and made key decisions about resource allocation.

The chat starts with a clear-eyed look at how Canadian and American entrepreneurship differ, especially when it comes to risk-taking and market dynamics. James draws from his experience at Clearco and other ventures, breaking down revenue operations in a way that actually makes sense.

The discussion gets real about B2B sales challenges today. James explains why credibility matters more than ever and why blasting thousands of emails just doesn't cut it anymore. There's a good bit about how LinkedIn has changed the game for professional networking - both the good and the bad.

One of the more interesting parts is when James compares bootstrapped and VC-funded companies. Having bootstrapped his own consulting practice, he talks honestly about keeping that direct line between what you do and what you get - something that often gets lost in the VC world.

They don't shy away from the tough stuff about Canadian business, including our banking system and those big monopolies we all deal with. The conversation covers how our massive geography and smaller population create unique challenges for scaling businesses here.

What works about this discussion is how it mixes big-picture thinking with real, day-to-day experiences. Whether you're running a company or working in sales, you'll probably find something useful in their take on building sustainable businesses in Canada.

They wrap up talking about why business should be fun and how to keep relationships real in the corporate world. It's a solid overview of what it's actually like to build and run a business in Canada today - no sugar coating, just straight talk about the challenges and opportunities out there.

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The interview offers fascinating insights into the early days of bootstrapping a tech company. You'll hear how they found their technical co-founder through a now-defunct website called techcofounder.com – talk about serendipity! Vitaly candidly discusses the challenges of starting with minimal seed funding and how they managed to turn that initial constraint into a strength, forcing them to build a sustainable business from day one.

What makes this conversation particularly valuable is Pecherskiy's practical wisdom about product development. He dispels the myth that you need a perfect product to succeed, sharing how StackAdapt started with basic features and evolved through constant customer feedback. There's a great section about how they approached solving the complexity in programmatic advertising by focusing on creating an intuitive, comprehensive platform.

The discussion takes an interesting turn when exploring global expansion. You'll learn how StackAdapt grew beyond Canada, now operating in 16 countries with a truly international team. Vitaly offers valuable perspectives on the challenges of breaking into different markets, particularly in Europe and Asia, and how they learned to adapt their North American approach for global success.

Throughout the interview, there's a recurring theme of sustainable growth and customer-centricity. You'll appreciate Vitaly's honesty about the stresses of early-stage entrepreneurship – he even jokes about his graying beard! The conversation provides real, actionable insights about expanding your total addressable market and the importance of thinking globally while acting locally.

Whether you're an entrepreneur, working in tech, or just interested in business growth stories, this interview offers a refreshingly honest look at building a successful global technology company. It's particularly relevant for anyone interested in bootstrapping, enterprise software, or international business expansion.

Our conversation traced the Trust's remarkable ~50-year evolution - including the recent transitions as Prince Charles III became the King of England, highlighting their innovative approaches to tackling youth unemployment in Canada. 

We delved into critical discussions about leadership transformation and organizational culture, especially in the post-COVID landscape where we all have to deal with fundamentally altered workplace dynamics and community connections.

A significant portion of our conversation centered on Canadian identity and the King's direct engagement with indigenous leadership - a testament to the organization's commitment to meaningful change.

The discussion included perspectives on entrepreneurship, relating tales from Startwell founder Qasim Virjee’s pioneering work enabling internet connectivity in East Africa to building community spaces at StartWell over the past seven years.

Throughout our exchange, despite addressing serious challenges facing Canadian youth, there remains a persistent thread of optimism about future possibilities and the power of community-driven solutions.

Kyle Norton joined us for this episode of the StartWell Podcast to explain his perspective on the best way to develop revenue operations with systems and a team that is truly committed to holistically helping customers through the product/service they are selling.

In his current role as CRO at Owner.com, Kyle leads sales, partnerships, onboarding, success, support, revenue operations and enablement - which has enabled him to develop tightly knit systems for optimizing value the organization and its customers.

With 15 years of experience under his belt (and multiple belts at that - he used to own a mixed martial arts academy), Kyle's perspective is informed through experiences running large teams at rapidly scaling companies including League and Shopify.

In this conversation, you'll learn about a systems approach to revenue operations plus Kyle's thoughts on work ethic, the Canadian context for entrepreneurship and much more!

Watch the full episode as a video here: https://startwell.co/blogs/business/the-fearless-approach-to-scaling-revenue-operations-kyle-norton

That number is massive - and is one of the motivating factors behind Mac Gebara's work with Emma-Jean Pride at Atrium; a boutique consultancy focused on developing leaders at fast-growing companies.

According to Atrium's market research, over $300B is spent annually on corporate training yet 75% of managers and leaders say they are dissatisfied with the training they receive from their company.

This episode of the StartWell podcast digs into how Atrium is solving the problem of leadership development through bespoke mentorship programming.

*Watch the full episode here: https://startwell.co/blogs/business/defeat-self-doubt-the-power-of-mentorship-in-leadership-development-mac-gebara

Jeremy joined us for this episode of the StartWell podcast to recap changes in tech since the pandemic - how education has shifted online and how companies are actively pursuing up-skilling and re-skilling workers to future-proof their existing workforce.

This episode will be enlightening to anyone working in HR/People & Culture as well as startup founders and team leads.

Lighthouse Labs is one of the country's first tech educators - now offering coding bootcamps for topics from web development to cybersecurity and data analytics. *Full episode in video here: https://startwell.co/blogs/business/the-future-of-coding-jobs-and-tech-education-jeremy-shaki-from-lighthouse-labs

They discuss the impact of social media on consumer behavior and the need for a more holistic approach to business, prioritizing the needs of people and the planet alongside profits.

This engaging discussion provides insights to anyone in marketing or running their own companies in competitive markets! *Watch the full episode as video in the StartWell Magazine

In this episode of the StartWell Podcast we hear Jean's career history (which began in fashion) and perspectives informed by her work driving strategic approaches in advertising - including anecdotes from client work; including a recent project to help the Canadian Olympic Committee connect their mission with young Canadians.

*View this episode as a video in the StartWell Magazine here.

Brands must take calculated risks and create spectacles to capture attention. Differentiation and establishing an identity are crucial, as is prioritizing customer needs.

For this episode of the StartWell Podcast, we sat down with Saul Colt of the Idea Integration Company - and discussed the challenges of creating a distinct brand personality in the digital age, navigating tensions between identity and expression.

You'll hear shared insights on leading a creative agency, including the importance of hiring trustworthy employees and striking a balance between creative and strategic expertise. There are also nuggets of wisdom offered on the challenges of managing client scope and the significance of thorough planning and preparation in content creation.

*Watch the video recording of this session here.

Through his experience at Uber, Dan learned a lot about transportation and when he was approached to further develop Canada's first online retailer for used cars, he jumped at the opportunity - and has since grown it into the largest operator in segment.

This is a fun and insightful conversation for anyone interested in the Canadian business landscape - from startups to scaleups, and comprises the 60th episode of the StartWell Podcast.

*Explore more via The StartWell Magazine: https://startwell.co/pages/magazine & the full show page for this episode here: https://startwell.co/blogs/business/from-venture-capital-to-running-ubereats-and-building-canadas-premier-online-car-store-dan-park

For this, the 59th episode of the StartWell (https://startwell.co/) Podcast, Roy shares his experiences and perspectives as a startup founder, tech innovator, investor and Torontonian.

His current occupation is as a cofounder of https://unified.to/ - a simple way for companies to unify data between multiple SaaS applications.

*View a full film of this episode in the StartWell Magazine here.

• The company's foundation story
• How Gwella is positioned to take advantage of legalisation when it eventually happens for psychedelics
• Why MOJO had to reposition its brand early on, and how it has found a groove which is allowing it to sell globally
• Why selling product through Amazon was initially difficult and how Stefany's team changed things to acquire a great product review rating and ensure better supply management.
• Why the company has high value for content and community.

• https://www.sbs.ox.ac.uk/programmes/oxford-impact-measurement-programme
• https://www.innoweave.ca/
• https://www.evaluatingimpactinvesting.org/
• https://ventureforgood.org/