Jay Gilbert

Reposting as I am a lover of great graphic design.

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Trolley isn’t just making moves—it’s rewriting the playbook. $23 million in Series B funding just landed, courtesy of Wavecrest Growth Partners leading the charge, with Pace Capital and GreenSky Ventures in the mix. Tim Nixon, the mastermind CEO and founder, is steering this Toronto-born powerhouse into uncharted territory, turning payouts and tax compliance into an art form. The kind that businesses don’t just appreciate—they can’t function without. This isn’t your standard “look, we got funding” story. Trolley is scaling the mountain of cross-border payments, dragging outdated systems kicking and screaming into the 21st century. Billions in annual payments, 2.5 million recipients, 210+ countries served—it’s global domination with a side of razor-sharp precision. They’re taking the internet economy’s wild west of payouts and whipping it into shape, slashing compliance costs by 35%, keeping 99.99% uptime, and moving money so fast, even banks are taking notes. And let’s not ignore the tech flex here: fraud prevention that catches what others miss, ID verification to keep things clean, tax compliance across 200+ jurisdictions, and parent-child account management that scales like it’s 2050. Toss in NetSuite integration, and Trolley isn’t just building a platform; they’re building the infrastructure for how global business gets paid. It’s no wonder heavyweights like Envato, Downtown Music, and GoTo have hitched their wagons to this rocket. But this is just the warm-up. With this fresh $23M injection, Trolley is gearing up to plant flags in even more territories, scale their go-to-market teams, and keep innovating where it matters—compliance and efficiency. Tim Nixon and his team aren’t just running a company; they’re orchestrating a global takeover with a fintech symphony that’s as ambitious as it is effective. This is the kind of momentum that doesn’t just shake up the industry—it reshapes it. For every startup eyeing global growth or every #Fortune500 chasing efficiency, Trolley’s making it clear: there’s a new standard in payouts. It’s faster. It’s smarter. And it’s here to stay. Tim Nixon, take a bow. The internet economy just found its backbone. #Fintech #Payments #TaxCompliance #IDVerification #Compliance #Efficiency #Technology #Innovation #TechEcosystem #VentureCapital #StartupFunding #StartupEcosystem #Startups

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Here’s one thing I know for certain. Surround yourself with an amazing team of professionals who excel at what they do. Meet Joanne Mondelli, Director of Engagement, and Natalia Reis, RGD, VP of Brand from the exceptional team at Q30 Design Inc. These talented professionals, alongside the entire Q30 team, have been an absolute pleasure to collaborate with on an exciting project I’ve been working on (more details to come, so stay tuned!). What I enjoy most about working with Joanne and Natalia is not only their unwavering commitment to delivering top-tier results but also their meticulous approach to project management. They bring a blend of creativity, strategic thinking, and attention to detail that’s rare and invaluable. I have complete trust in their expertise, knowing they will lead me in the right direction. Here’s the thing—when you hire professionals who align with your values and are experts in their field, you empower yourself to focus on what you do best. It's about working smarter, not harder. By trusting their leadership, I can channel my energy into the core areas of my business with confidence. Remember this: micromanaging leaders in their field not only disempowers them but also holds you back. When you allow people to shine in their respective roles, you enable growth, efficiency, and success across the board. Success isn’t about doing it all—it's about doing what you do best and letting the right people handle the rest. Trust your team, and watch how far you can go together. #collaborationovercompetition #leadership #empower #teambuilding #leadershipinsights #leadbyexample #management #humanfirst

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I’m trying to get as much as possible or from the Deceptive Patterns work into WCAG 3 because I know it belongs in there at some level. Think about it. Manipulative behavior from manipulating people working at companies that manipulate for the almighty source that is revenue, is inaccessible among other things. Comparison prevention for example. Hiding the lowest tier that is probably the least profitable but most affordable for people is inaccessibility. Hands down. Fake scarcity. Limited time only! When in fact there is plenty on-hand or in a backstock. Deceptive patterns need to go into WCAG3, period.

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A major setback for Canada's startup ecosystem as early-stage capital becomes even harder to come by. It's disappointing to see the challenges facing small businesses across the country exacerbated by this latest development. Let's hope the Government of Canada takes note of the impact this will have and takes steps to support our entrepreneurs. #startup #smallbusiness #entrepreneurship #Canada

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Toronto is home to Toronto Tech Fest. What started out early this year as a week long celebration of Toronto's founders, builders, and innovators at the leading edge of technology, soon ballooned into one of the city's largest tech gatherings spanning the entire innovation ecosystem and tech community. Generating this energy in Toronto, has been one of the most rewarding moments of my life as an entrepreneur and community builder. Here's the impact we've had in Year 1: ✨ 90+ events held across 4 days ✨ 255+ co-hosts and partners activated ✨ 10,000+ signups with people flying in from New York, Chicago, SF, LA to attend. By creating a platform for all participants (founders, investors, builders, community leaders) to create, connect, and catalyze each other, we amplified the power of the tech community at the grassroots to foster real change and opportunity for the Toronto innovation ecosystem. By the community, for the community. So now, with Collision moving to Vancouver in 2025, those of us who believe in the innovative future of Toronto must take up the torch 🔥! We at Toronto Tech Fest are committed to carrying forward the spirit of innovation in Toronto, across next year, and for years to come. This means activating our tech community and investing in even more innovative programming that draws in new talent, adds value for founders, builds bridges with local businesses, and showcases why the tech community in Toronto is world class. Let's fight for this future together! Comment below 👇 or connect with me or Mell Truong via DM if you're interested in joining us to make a lasting impact on Toronto innovation in 2025 and beyond.

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Fun video from my recent book launch event, hosted by CIBC. Spot someone you know in the crowd, drop their name in the comments, and I’ll write you a haiku below. It was a beautiful gathering of friends and colleagues, including video interviewees Sean Thompson, Paul Lightfoot, Molly Blomquist, and the brilliant Charlene Li, who served as our incredible moderator. The crowd was filled with people building  breakout companies the right way. We explored how operating from a deeper intuition leads to stronger companies, especially in an ecosystem that seems intent on promoting failure. Some key takeaways: how to  • Transform yourself to transform your company • Determine if a business can be turned around  • Be in the 10% of successful startups through patience, learning, and focus It’s rare in life to come out with a vulnerable version of yourself and have it so well-received. I’m so grateful for all of you who made it. If you’re interested in applying these principles, let’s connect. #BookLaunch #Entrepreneurship #Leadership #Reignition

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We released our annual Economic Impact report (with Public First) yesterday, with a focus on AI's impact in 🇨🇦 . These highlights below square with what I hear daily from customers. Canada's AI future is bright, let's get after it! * Generative AI has the potential to boost Canada’s economy by $230 billion and could save the average Canadian worker over 175 hours a year, freeing them up to concentrate on more fulfilling parts of their job. * 80% decision makers from businesses that are early adopters of technology agree that AI will make Canadian businesses more productive. * In total, it’s estimated that Google Cloud is saving 145 million business hours for the Canadian economy each year. This is equivalent to at least $10.1 billion a year in business time savings for the Canadian economy. * It’s estimated that Canadian businesses have saved $420 million in costs and efficiency by transitioning from more costly on-premise servers to Google Cloud.

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There have been three pivotal times in Vendasta’s journey when I knew we had something extraordinary on our hands, and this is the most powerful yet. ⚡️ AI has reached a point where it’s not just a tool but a transformative force, and I can’t wait to share how it’s shaping Vendasta’s vision for agencies. On November 14, I’ll be presenting live (I'm coming back from speaking at a conference the day before, because I don't want to miss it!🌍), showing you the product in action and how our AI tools are opening doors for agencies to scale, capture leads, and drive revenue like never before. We’re putting groundbreaking power into your hands—and it’s truly something special. 💡 Don’t miss this chance to see what the future holds. Join us and 1,000+ of my closest friends ;) 👉 https://lnkd.in/gZqiix5d #VendastaConnect #AI #AgencyInnovation #ProductVision #FutureOfWork

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I just came across this awesome example of how Shopify Inc's CEO Tobias Lütke ran a company-wide remote work experiment in 2017 that helped the company's anti-fragility when Covid-19 hit three years later. Background - Shopify is always trying to help employees stay curious, for example getting employees to use the mouse with their left hand for a day. In line with this, in 2017 Shopify closed the company’s offices for a month, requiring their then 800 employees to work from home. This was a strategic move to enhance the company’s adaptability. During that month, the company and its leaders encountered unexpected hurdles, such as interns struggling to find food without the office kitchens. This challenged the employees to get creative, for example - the kitchen staff bought and ran a food truck! Lütke explained their philosophy on building adaptability in an interview with The Motley Fool "One of the things that we've been trying to do is ... inoculate the insides of the company from the crazy changes that exist on the outside. All of us are on boats in very stormy waters in the industry today, because there's a million different micro trends that are all hitting us in the form of tidal waves at the same time." (1) Imagine how much this experiment readied Shopify's leaders for Covid - a time when they simultaneously needed to go remote and respond to a massive increase in the number of entrepreneurs needing their help? This builds on Lütke's views on the importance of "Antifragility," where a system responds to disruption not just with stability, but by getting stronger. This concept was introduced in Nassim Taleb's book of the same title, one Lütke loves and tells everyone to read (as he said in an interview with Andreessen Horowitz General Partner, Sriram Krishnan (2)). Antifragility is such an important idea for building adaptable companies that MIT teaches the concept to its entrepreneurs. Bill Aulet explains how and why the Martin Trust Center for MIT Entrepreneurship does this in an article by MindFrame Connect https://lnkd.in/e_vyxzg5 Enjoy! Sources 1: https://lnkd.in/ewmUkshD 2: https://lnkd.in/e6SkrH5N

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At Tech To The Rescue, our team is always focused on having an *impact mindset.* So, naturally, I was excited when I discovered this report that explores everything from corporate giving to company courage (one of my favorite concepts). But what exactly is an impact mindset? I love how Benevity defines it: “Embedding positive social and environmental impact through an enterprise’s culture, brand, and operations.” This perfectly aligns with why I’m so passionate about our mission at Tech to the Rescue. We don’t just do a good deed and move on. We build systems and habits that embed impact as a continuous and integral part of our daily work. More importantly, we also try to impart that mindset on others, whether tech companies who join our call or people we meet out in the world. We are always on a mission to spread the importance of collaboration. It’s important to recognize that adopting an impact-focused approach isn’t just good for society, it’s a powerful advantage for businesses. As Benevity puts it, “Embracing an impact mindset gives companies the chance to not only meet today’s challenges but to build resilience in their business, culture, and communities.” It’s a critical shift, moving us beyond reactive responses and toward a more strategic, forward-thinking future. If you want to learn more about how businesses can embrace an impact mindset, I highly recommend checking out the report. Link in the comments. #ImpactMindset #TechForGood #CorporateResponsibility

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Women’s Enterprise Centre of British Columbia (WeBC). Offers $150k loan to women entrepreneurs for startups to scale and grow, to acquire a business, and for business expansion projects. https://lnkd.in/eqCs-iWu

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Such a great blog post which I suggest every founder read. So many golden nuggets in here. But one that stands out: What are some qualities that you see in the most successful founders? Well, I love smart people, with high IQs, and high EQs, that’s great. But, of the founders that I see, the highest correlation with success is with their grit quotient. They’re not necessarily the smartest people in the world, but their grit and determination are unbelievable. They never give up and always find a way to blast through any obstacle they face. It’s the mentality of “succeed or die” – it’s that kind of determination that wins. #gritcotient #grit #founder #highperformancemindset

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Hello Canadian 🇨🇦 and New Zealand 🇳🇿 product leaders! You asked for one more get-together before the end of the year! Following the great response to our first couple Lean Coffee events, we will be hosting another Lean Coffee on Tuesday December 17 at Noon PST / 3 pm EST, which is Wednesday at 9:00 am NZDT. Bring your topics of interest! We will get them on our Miro board and vote on the most interesting topics to discuss. Enjoy a moderated discussion of the top voted topics with your peers in product leadership. You will receive ongoing access to all the Miro board with all Lean Coffee notes for your reference. Details in the Product Leader Summit # Canadian Product Leaders slack channel. Details also in the Product Leaders slack channel. If you are a product leader with Director-level or above experience, we would love to have you join us! DM me for more info, or to be added to the calendar invite. #ProductLeaderSummit #ProductLeaders #LeanCoffee

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Lots of media 📢 over the last week since the launch of our fresh new e-commerce platform that is already revolutionizing the landscape across Ontario! Thank you Bell Media, CP24 Toronto's Breaking News, Trend Hunter, Strategy Online, Yahoo Finance, CHCH TV, LinkedIn News, Post City Magazines, Zoho, and many others for the continued support! Many of our new members this week have shared what they like most about Go Lime Inc. --- and a big thank you to our marketing team for collecting these insights from our few dozen customers that have bought 100% online!   🍋‍🟩 "In today’s digital world, you can buy nearly everything online—so why should HVAC systems be any different?" 🍋‍🟩 "No one likes dealing with pushy salespeople or navigating complicated contracts. That’s where Go Lime has changed how we view the entire category." 🍋‍🟩 "We loved purchasing our new Water Heater online on your super easy to navigate site --- it's as easy, transparent, and hassle-free as any other seamless online shopping experience. Yes, it really was that simple! We had our new Energy Efficient Water Heater installed the next day!" 🍋‍🟩 "We did not realize we were over paying by up to 50% for our 15 year old water heater --- thank you Go Lime for giving us the option to buy a new tankless option including installation that pays for itself vs what we were paying to RENT."   It took many months and 1000's of hours of market research to understand how we could better serve Ontario Households and we feel we are absolutely shaking up an industry that hasn’t evolved in decades. Unlike most companies that hide their prices, trap you in long-term rental contracts, and send pushy salespeople to your home, we believe in full customer transparency. Our pricing and options are all online, upfront, with no need for an in-home visit. Plus, with our Go Flex subscription plan, you can buy your equipment whenever you’re ready if you prefer to pay monthly — with no strings attached! We're also dedicated to providing affordable, sustainable solutions for every household across Ontario. Whether you're upgrading to an energy-efficient water heater or going for a complete net-zero home, Go Lime has you covered.   Go Lime offers a modern approach that saves you both time and money. At the heart of it all is a simple belief: it’s your home, your comfort, and your choice. We empower you with full control—without the usual industry hassle. Shop online with Go Lime today! Thank you to our growing team that is fueling this fresh 🍋‍🟩 revolution --- and yes...we are just getting started! #Sustainability #PurposeBuilt #Teamwork #CustomerChoice #Hiring

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Look out Toronto — Conversations in Commerce is coming for you next month! Ever felt frustrated and abandoned a purchase because the checkout process was a nightmare? You're not alone. That's why we're delving deep into the crucial topic that affects every single transaction: the checkout process. These days, customers now expect checkouts to be personalized to their preferences and super easy to navigate. The key to success lies in providing a seamless experience but challenges like technology limitations and business constraints can hinder your efforts to create that ideal experience. Don't fall behind with a clunky checkout process. Come learn from the city's very best. June's fireside chat will reveal how top leaders have tackled obstacles to enhance the checkout experience. We've got some great speakers in the works so stay tuned. 👀 Register here: https://lnkd.in/eHveecdB Shopify, Signifyd, Zowie Diff, a VML Company

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Last week ResVR announced the successful completion of their most recent funding round. Led by Founder Nathan Nasseri, who worked his tail feathers off to get his startup into all the very best spots so his venture could select investors based on strategic fit, ResVR is now very positioned to carry it's fight forward. The company is moving assertively into the market at the bottom of the recession or at the earliest stages of the recovery. Either way, the team is ready to catch the wave of growth that comes with a bounce back from the bottom. Real estate remains Lex Luthor's favourite asset class, and smart, accessible and useful technology products can change how real estate developers and home builders take their businesses to market and more importantly make more money and create more tailored environments for their customers. More tailored home environments create happier people. If you haven't figured out the difference between a house and a home yet, you will. And once you do, you'll work to make your house a home fast and will willingly spend the money to do so. ResVR sent out a press release to announce its success and it's hit thousands of accredited and respected trade publications from the Chicago Tribune, The Globe and Mail to more industry specific partners in venture capital and home building. Celebrate your company's wins! Always. #resvr #startups #proptech #realestate #pressrelease #takethewin #sharethewin #saas https://lnkd.in/gNiMV95H

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I was geeking out last night with an old co-worker in Toronto from the DataRobot glory days. We had one of best creative teams in tech, we really did. The projects were bold, incredible creative talent, award winning content. The best the marketing has to offer: Content worthy of your attention. The More Intelligence Tomorrow podcast and team were 🧑‍🍳 😘 I was reminded of the profound power of words. The words you are reading now can change you, with the right recipe of ideas you might even quit your job. You might even feel an emotion you weren't anticipating. You could even cry. Here is AI having some fun below, playing with this concept of #wordpower: THE FINITE "Your daughter just asked why grandpa's chair is empty. Somewhere, a clock is ticking. Your father's laugh now only exists in your memory, and you can't quite remember if it had that rough edge to it. Time isn't running out - it's already gone." Feel: A vacuum in your chest that makes breathing feel like theft Act: You cancel tomorrow's meetings to teach your child how to make his pasta sauce THE LEAP "That project you keep in your bottom drawer isn't just paper - it's the life you're too afraid to live. Your safe job pays well, but at night your dreams speak in 'what-ifs' and your heart beats in 'somedays'. When was the last time you felt truly alive?" Feel: Lightning in your veins, terror dancing with ecstasy Act: You start writing your resignation letter at 3 AM, hands shaking, soul soaring THE UNSAID "The last text you didn't send. The coffee you didn't share. The words that died on your tongue when pride spoke louder than love. They say time heals, but regret? Regret carves canyons." Feel: Your heart attempting quantum physics - breaking and healing simultaneously Act: You finally type "I miss you. I was wrong." and hit send before courage fails THE MIRROR "Look at your reflection. Really look. Behind those eyes lives every version of you that died so this one could live. The coward who became brave. The broken who learned to heal. The silent who finally screamed." Feel: Your skin becomes too small for all the souls you've been Act: You begin writing the story you've been terrified to tell THE AWAKENING "In the space between seconds, between breaths, between being and becoming - you exist in infinite possibility. Your life isn't happening to you. It's screaming for you to happen to it." Feel: Reality cracks like an egg, spilling raw possibility everywhere Act: You buy the one-way ticket, leave the map behind, and finally begin living your story instead of someone else's script I think humans will never understand the true power of language and the impact it can truly have an other human. A big part of this badass creative team exists at: Deep Vibe I miss the creative dream team: Heather Ferguson Michael Gilday Isamar Perez Uroš Perišić Nicholas King Danielle Kieschnick Brendan Coughlin

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