The StartWell Podcast

Former Anduril executive Eliot Pence left Washington DC to build the defense company Canada never had. Here's why he came back — and what's at stake.

Steven Wang, Rhodes Scholar, Harvard-trained lawyer, and CEO of Venture for Canada, joins Qasim Virjee at StartWell to talk about what it really takes to future-proof the next generation of Canadian workers, why the country has an experience gap (not a talent gap), and why buying a small business might be one of the most underrated entrepreneurial moves of our time.

Karim Gillani has had a front-row seat to some of the most important shifts in technology and finance over the past two decades. From early days in mobile payments to leading M&A at companies like Xoom and PayPal, and now as a co-founding General Partner at Luge Capital, his perspective on venture capital is shaped by real operational experience.In this conversation, Karim breaks down how the rules of building and investing in startups are changing - fast.

*Recorded at StartWell - Toronto's campus for corporate meetings & events: https://startwell.coGhassan 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.”

*Recorded at StartWell - Toronto's campus for corporate meetings & events: https://startwell.coBen 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.

*Recorded at StartWell - Toronto's campus for corporate meetings & events: https://startwell.coMax 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.

Goodlawyer CEO Brett Colvin explains why Big Law incentives are broken, how fractional general counsel works, and how scaling companies can modernize legal support with embedded in-house talent.

What if “networking” is broken - and leadership is lonelier than we admit?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.

In this episode, Qasim sits down with Katie Zeppieri, founder and CEO of The Mic Drop Agency, a PR and marketing firm working with venture-backed tech startups, reality TV talent and authors across North America. From her new base in Austin, Katie helps founders and executive teams tell their stories, earn trust, and grow faster.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.

In this episode of the StartWell Podcast, Ruslan Nikolaev, co-founder of Float, shares the journey of building a fintech startup aimed at revolutionizing financial management for Canadian businesses. 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!

This episode of the StartWell Podcast explores the multifaceted nature of community building in business as we sit down virtually with Joshua Zerkel; a community-led growth and engagement leader who has done amazing work for technology companies operating at massive scale; including Asana and Evernote.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.

In this episode of the StartWell Podcast, we sat down with Nik Milanović, founder of This Week in Fintech (the world's largest fintech community with 160,000 subscribers.)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.

For this second conversation with Carbon6 - 2 years after we last had them in studio, you'll get an insider's look at one of the most dynamic success stories in the Amazon seller software space. Carbon6's journey from ambitious startup to industry powerhouse unfolds through candid discussions with its co-founders, who share both the triumphs and challenges of building a tech company through acquisition and organic growth.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.