Make it Click

Borderless AI Media Lab
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On Make it Click, Willson Cross (CEO and Founder of Borderless AI) explores compelling, future-focused subjects—like AI, nailing early product-market fit, and early-stage investing—with experts, innovators, and big thinkers.

Episodios

  1. 2 sep

    From a Surf Trip in Tofino to $100M+ Raised: The Certn Story with Andrew McLeod | Make it Click

    What does it actually take to turn an idea into a company with hundreds of employees and more than $100 million raised?Certn co-founder and CEO Andrew McLeod joins Willson Cross on Make It Click for a founder-to-founder conversation about the nine-year journey behind one of Canada’s standout tech companies. Andy shares how an idea dreamed up while surfing in Tofino evolved through multiple pivots, why he believes founders should find the customer before building the product, and how Certn went from early prototypes and design partners to a global background screening business.They get into the parts of scaling that rarely make the highlight reel: raising the first dollar of venture capital, choosing investors you actually want around the table, competing in crowded markets, hiring the right leaders, and making the transition from scrappy founder to disciplined operator.Andy also shares some of the harder lessons he has learned as a CEO, including why being kind does not always mean being nice, why great leaders need to have difficult conversations, and why the best feedback is often the feedback people least want to hear.Plus, they dig into building a global company from Canada, work-life integration as a founder, the role of grit versus luck, and why there is no such thing as an overnight success.

  2. 29 jul

    Boris Wertz on why VCs Are Betting Everything on "Outliers" Now | Make it Click

    Boris Wertz, General Partner at Version One Ventures, sits down with Willson on Make It Click to break down how he deploys roughly half a billion dollars (CAD) into early-stage, mission-driven founders.He shares why he backs founders well before a category hits the mainstream, how his new $78M Fund Five and $30M opportunity fund allow him to double down on breakout companies like Clio, Jobber, Ada, and Coinbase, and why he believes the biggest outcomes concentrate in a vanishing few. Along the way, he retraces his own journey from founder — JustBooks, acquired by Amazon through AbeBooks — to full-time investor, and offers candid perspectives on AI's impact on the app layer, marketplaces, Canadian deal flow, and what truly sets an outlier company apart. Make it Click is an original podcast, hosted by Willson Cross and produced by Borderless AI

  3. 24 jun

    Nick Frosst: A Rock Star by Night, $7B AI Co-Founder by Day | Make it Click

    Nick Frosst is a co-founder of Cohere, the Toronto-based enterprise LLM company valued at $7 billion.In this episode of Make it Click, Willson sits down with Nick to talk about why Cohere bets exclusively on B2B, how on-prem deployments protect customer data in regulated industries, and why the consumer AI race has economics that don’t add up. Along the way, Nick shares his contrarian take on AGI hype, AI sovereignty in a shifting geopolitical landscape, and why he’d tell an 18-year-old not to start a company just yet. Outside of AI, Nick is also the frontman of indie pop-rock band Good Kid.

  4. 20 may

    Jack Newton & Dennis Pilarinos on $500M ARR, Apple Exits and AI | Make It Click

    Clio’s first investor found Jack Newton through a random blog post that almost never got read. Dennis Pilarinos sold his first company to Apple, then went back to building from scratch with Unblocked.In this episode, Willson sits down with Jack (CEO, Clio) and Dennis (CEO, Unblocked) to talk about the sliding door moments that define companies, why AI is transforming legal and developer tooling faster than almost any other industry, and what it really takes to build for the long haul.They get into managing a cap table across decades, building context engines that actually win markets, and why the founder brain never fully shuts off — even when you’re kayaking with your kids.

  5. 29 abr

    From Espresso Shots to a Billionaire Empire: Andrew Wilkinson's Quiet Blueprint | Make it Click

    In this episode of Make it Click, Willson Cross sits down with Andrew Wilkinson in Victoria, BC to trace the full arc, from college dropout pouring espresso shots to quietly becoming one of Canada's most prolific business builders. He gets honest about the failures along the way, the ADHD diagnosis that reframed everything, why he stopped drinking, and how AI is now letting him build without scaling headcount.Most founders think the only path to building something big runs through Sand Hill Road. Andrew Wilkinson proves otherwise.Andrew is the co-founder of Tiny, a holding company that owns 25+ businesses, including AeroPress, Letterboxd, and Serato, generating over $250M in annual revenue. He built it without venture capital, without a board breathing down his neck, and without sacrificing the businesses he loved to the highest bidder. He also wrote the book on it, literally: Never Enough: From Barista to Billionaire.If you've ever wondered whether there's a smarter, quieter way to build wealth without giving away your company, this one's for you.You'll hear about: the Warren Buffett-inspired acquisition model that changed everything · why B2B SaaS might be the next e-commerce · using AI agents to run businesses lean · the real cost of public persona and people-pleasing · and what financial freedom actually feels like when you get there.Key moments: 00:00 – Introduction04:38 – The $500 BBQ job that started everything05:38 – How Andrew lost it all on cat furniture and an online DJ school06:21 – The Warren Buffett idea that became Tiny07:00 – AeroPress, Letterboxd, Serato — following passion into acquisitions14:00 – Why Andrew never raised venture capital22:00 – The difference between being rich and being free31:00 – The ADHD diagnosis that reframed his entire career38:00 – Why he stopped drinking and what changed45:00 – Divorce, vulnerability, and the email that broke all his records52:00 – Why B2B SaaS might be the next e-commerce57:00 – Using AI agents and Claude Code to run businesses lean01:04:00 – Two meetings a week and total freedom — what his days look like now

  6. 14 abr

    How Borrowell Turned a Problem Into 4 Million Users | Make it Click

    In this episode of Make It Click, Willson (Borderless AI's Founder), sits down with Andrew Graham, CEO & Co-Founder of Borrowell, to learn what it actually takes to build a lasting FinTech company in Canada, without a idea or a roadmap (and in Andrew’s case, with a newborn at home).From hot-desking at TMU's Digital Media Zone to leading a platform trusted by nearly 4 million Canadians, Andrew shares how he went from political staffer to Harvard MBA to corporate executive and why he walked away from all of it to solve a problem he couldn't stop thinking about.- Why you don't need an idea to start a company, just a problem worth solving- The double-sided fundraise nobody warns you about when building a lending business- How Borrowell turns competitor ad spend into their own growth- What building a remote-first Canadian company actually looks like at scale- Why there's never a perfect time to take the leap (and why that's actually good news)If you've ever wondered what separates founders who survive the early chaos from those who don't, or what it really looks like to build something meaningful over a decade in Canada, this conversation is worth your time.Because sometimes, the thing that makes a company click… is falling in love with the problem before you ever find the solution.

  7. 31 mar

    What Makes a Startup “Click”, Before It Even Exists? w/ Matt Cohen | Make it Click

    In the first episode of Make It Click, hosted by Borderless AI Founder Willson Cross, we sit down with Matt Cohen, Founder & Managing Partner at Ripple Ventures, to unpack what actually makes a startup work, before there’s even a product, customers, or sometimes even a company.From backing founders at the idea stage to helping companies navigate pivots, shutdowns, and everything in between, Matt shares how he evaluates early signals most people miss and why team, problem, recruiting, and fundraising matter more than any pitch deck.In this episode, we get into:- The traits that truly separate great founders from the rest- Why many startups fail - How early-stage investors think about risk, pivots, and second chances- The difference between Canadian and U.S. founder ambition- What founders need to figure out about their life before starting anythingIf you’ve ever thought about building a company, or wondered why some ideas take off while others stall, this conversation offers a clear look at what’s really happening behind the scenes.Because sometimes, the thing that makes a company “click”… isn’t what you think.--- Keep the conversation going: Follow Borderless AI on LinkedIn: linkedin.com/company/hireborderlessConnect with Willson: https://www.linkedin.com/in/willsoncross/Connect with Matt: https://www.linkedin.com/in/matt-cohen1/Interested in diving deeper? Check out our Media Lab: https://www.hireborderless.com/media-lab

  • 7 episodios

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On Make it Click, Willson Cross (CEO and Founder of Borderless AI) explores compelling, future-focused subjects—like AI, nailing early product-market fit, and early-stage investing—with experts, innovators, and big thinkers.

Información

  • Creador
    Borderless AI Media Lab
  • Años de actividad
    2026
  • Episodios
    7
  • Clasificación
    Explícito
  • Copyright
    © Borderless AI Media Lab
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    Make it Click