Simon De Baene

I stayed up coding until 4am so many nights for two years when I started Lightspeed Commerce — to me, this is part of the entrepreneur journey. Had a blast reflecting on those early years and discussing the challenges and opportunities of navigating a tech startup with Harry Stebbings from 20VC. Some takeaways: - Achieving strong product-market fit requires an iterative, customer-centric approach — especially with early users. Lightspeed wouldn’t have achieved profitability if we weren’t so close to our customers. - Companies can take different paths to scale, each with its trade-offs — some bootstrap profitably for years before taking VC funding. Sometimes you need the slow-burn process to create something truly phenomenal. - Founders must be willing to adapt their sales and distribution strategies as the business matures, especially after going public. If you’re a founder or entrepreneur, I think this episode will provide lots of value. Thank you to Harry and the team at 20VC for having me. Links to the interview in the comments 👇

193

17 Comments

Short teaser of my upcoming COO podcast. In this episode, I chat with Jean (John) Lafleur, Co-Founder and COO Airbyte about fundraising, what the role of the COO means to him, how to build teams with talent density, and fighting entropy. I will be posting an update here next week and a link to the full interview! Follow me for more updates and COO interviews.

26

3 Comments

The best part of Revenue Kick Offs (besides connecting with the team) is hearing from individuals with high-growth company experience. Big thank you to Emmanuelle Skala for hanging out with us at our RKO to talk about her time scaling Toast from $20M > +$1B (and her other roles at Sophos, Influitive, DigitalOcean and Endeca). Some takeaways from her chat with Philip Braden: It's everyone's responsibility to surface inefficiencies in a business. It's not solely leadership's responsibility. As you grow, not everyone can be in the room anymore. You have to trust the people delegated to make those decisions. And it's not only leaders; it's a group of people where ideas are vetted, keeping leaders grounded in reality. Get very good at running very rapid tests. As you grow, it's imperative to test changes before full implementation. Assumptions/Emotions don't matter when you have a real reason to implement change. Don't get emotional about change. Ultimately, it will be better for your career. Embrace it. You can say, "Hey, if I were to change something, here are some things that might make a difference." If you need help understanding the WHY behind the change, feel free to speak up and ask. You should have a solid answer. Alignment = common objectives and truth in data 

87

7 Comments

🎉 Big News at Dreamcraft Ventures! 🎉 I'm very proud to announce the promotion of Mathilde Lyet to Investment Principal, effective October 1st. Since joining 12 months ago, Mathilde has demonstrated strong dedication to Dreamcraft’s mission and a unique blend of analytical rigor, empathy, and leadership qualities that make her an invaluable part of our team. Here’s my five keys on why she's earned it: 🔑 Analytical Mind – With her strong investment toolbox from across stages, Mathilde excels in deep analysis and articulate decision-making. She’s a powerhouse when it comes to running investment motions independently, consistently delivering high-quality work. 🔑 Constant Learner – Always seeking to further sharpen her already well-tuned instincts beyond numbers, particularly for early-stage. And I’ve enjoyed so much being one of her primary sparring partners there. That curiosity and drive for continuous improvement is key. 🔑 Top-Tier Sourcing – Her dealflow brings a unique piece to our firm’s puzzle, building strong relationships across the European VC ecosystem while staying ahead of trends. She keeps her pipe a bit contrarian and avoids the pitfall of too much crowded consensus. 🔑 Operational Excellence – In addition to her investment work, Mathilde has played an important role in optimizing firm operations. From co-leading the hiring of analysts to improving the structure of our investment meetings, her impact has been felt across the team. 🔑 Empathy Leader – Mathilde's combination of intellectual curiosity, emotional intelligence, and a no-nonsense approach makes her a founder magnet and cultural leader internally. There’s just a way of doing this job without being an asshole, and she’s nailing it. Her promotion is not only a recognition of her past accomplishments but a signal of the exciting future ahead. Mathilde, I’m excited to see how you’ll continue to shape Dreamcraft's success and culture as we move forward! Let’s all give her a huge congratulations! 👏 #Dreamcraft #Leadership #VentureCapital #Teamwork #PromotionCelebration

138

12 Comments

I’ve never read a book written by a friend, until now. Fin Heureuse is only available in French for now. In it, Derek Morin reverse-engineers his startup exit in just 24 months. And he does it with flawless execution. Knowing the person behind the words you're reading is a feeling I might not get to experience often, but I loved every page of this book. Here are 3 things that stood out to me: → The ugly > the bad > the good Derek doesn’t hold back. He even shares how he planned to push some people out right before executing his exit plan. → The recipe + the ingredients + the cooked meal From revenue numbers to growth metrics and the accounting books, he shares it all. You’ll also see how he course-corrected in real-time. → From decision made to the finish line, step by step He lays out the 24 months in chronological order, event by event, sharing what he learned along the way. It was a short, fun, and informative read. Reading Derek’s book encouraged me to do two things: → Be more surgical about our growth and direction, even without an exit in mind. → Start planning my own book, a dream I aim to achieve one day. Now while I work on convincing Derek to write the English version, I highly recommend it to my French-speaking founder friends. -- That’s Derek Morin, a successful founder, author, and friend. Follow him to learn how to build a no-BS startup.

11

5 Comments

When you’re new to a role, you have a rare gift: the chance to see a company with fresh eyes. It’s an opportunity to make real change — but there’s a caveat… It doesn’t last forever. I’ve seen this first-hand returning as CEO of Lightspeed Commerce. So, how do you seize this moment? I think the first (and most crucial) step is listening. Don't go in with an agenda — find out what’s working (and not working) from a product or strategic direction, and be sure to get everyone’s opinion from the frontline to the boardroom. I’d love to hear from colleagues who have jumped into new leadership roles: How did you make the most of your first 90 days?

282

26 Comments

Two uber smart leaders in the NocoLoco Ops space are here to tell you that making tech work for you is a smart way to stay agile. It also helps you move into a state of flow and achieve revenue abundance that only this kind of tech can provide! Now is the perfect time to look at your current processes. Get clear and brutally honest about what Ops are actually working for you. Even if you are unsure of what process you need, I recommend reaching out to Alexandre Kantjas from 9x Manuel Ensinger Circula for a conversation. #NocoLocoOps #SystemsThatFlow

2

1 Comment

i want to talk about "admin flavors", something i start to notice, is how Shopify is secretly replacing many business and ops tools. many brands we worked with at Autrement, have one way or another a business tool, a custom built technology that reflects team expertise, some brands use ERPs, some have it in-house, some use both, especially in b2b, or retail. a tool that unifies many aspects of the business, each business is unique thus each business stack has its own challenges, its own flavor i call it. what's the relation between this and that? good question. the concept of "admin flavors" is a key outcome of this approach. a flavored admin is a customized version of Shopify (operating commerce system and backoffice), tailored to meet the specific needs of different businesses especially verticals. - for instance, fashion retailers might have integrated size guides and lookbook and e-merchandising management tools inside shopify. - while food and beverage businesses could benefit from recipe databases and nutritional information blocks. - electronics retailers might have specialized warranty management and technical specification tools built into their admin interface. these customizations improve operational efficiency and allow brands to maintain their unique workflows. shopify is an open and extendable platform at its core, they give you the building bricks (extension components and apis), a map where you add them (extension points) these blocks act as bridges between shopify and other business tools, enabling seamless integration of various operations. as this process unfolds over time—an admin extension here, another there—you end up with a unified operational system. a tool that centralizes everything you use across different platforms. instead of switching between tools, which can cause significant issues, especially regarding privacy and permissions at scale, you have a single, controlled environment. in a disjointed system, a staff member might be denied access to a resource in one platform but inadvertently granted it in another for a specific task, leading to potential security breaches. a unified system helps mitigate these risks, that will ported by shopify. looking to the future, we may see the emergence of industry-specific apps offering pre-configured admin flavors for different verticals. I've personally observed this in fashion, where some solutions have moved outside Shopify to build this up, because Shopify's current admin extensibility state isn't yet mature enough to fully accommodate these tools. However, it's only a matter of time before it will be.

30

New episode of IEP with Allan Leinwand from Webflow (previously Shopify, Slack, & Zynga), who's focused on bringing development superpowers to everyone ! GREAT takeaways from our conversation: 💡 An unexpected lesson Allan learned in his career: Hiring the right people makes you a better leader. 💡 The best CTOs do two things really well: drive the industry forward and engage in hands-on technical work. 💡 Engineering teams have to balance tech debt and innovation. Allan's approach is to address P0s and P1s immediately. Allocate resources to avoid recurring problems. And once the urgent issues are resolved, dedicate time to innovation. 💡 AI accelerates development, from writing code to running automation to conducting PR reviews. Allan is most excited about using AI to enhance workflow efficiency significantly. 💡 Allan predicts the future of web development will shift towards integrated platforms. Consolidation of products into cohesive platforms will streamline development and solve the “Franken platform” problem. Thanks Allan for joining the podcast and sharing your wisdom 🙏 #podcast #GenAI #webdevelopment

23

2 Comments

A lesson from Shopify: Stop obsessing over churn. I just listened to an incredible podcast featuring Archie Abrams, VP of Product and Head of Growth at Shopify, and it left me buzzing with ideas about what it truly means to build a resilient, customer-first business. One question stood out: Why doesn’t Shopify obsess over churn? Here’s what I learned: 1️⃣ Optimize for the long game. Shopify doesn’t view churn as a core problem—it’s a natural outcome of their mission to empower entrepreneurship. Their mindset? If you lower the barriers to entry and help as many people start as possible, a few will scale to massive success. Those success stories make the entire cohort worthwhile, even if churn rates are higher. 2️⃣ Embrace experimentation, but remain accountable. Shopify runs countless experiments, but what’s different is their timeline for accountability. They’re tracking impact years down the line to ensure their initiatives drive sustainable growth—not just short-term spikes. For a founder like me, this is a powerful reminder: shipping fast is important, but the real value comes from continuous learning and long-term refinement. 3️⃣ A hundred-year vision. Shopify’s north star is to build for the next century, not the next quarter. Every decision is grounded in what will benefit their merchants for decades. This kind of thinking is rare—and deeply inspiring. As I reflect on Brij’s journey, this long-term mindset encourages me to stay patient and focused on building a platform that will deliver value for years to come. Our long term bet? A platform that truly bridges the offline & online worlds. Is it easy? Nope. Will it take time? Yep. Is our vision huge? You bet it is. Check out the link in the comments. #churn #saas #growth

16

If you're a Canadian entrepreneur, investor, or founder then this past week has made it painfully clear that when it comes to innovation and economic recovery the calvary won't be coming and is in fact running in the opposite direction. The federal government and associated regional innovation support agencies (ie Invest Ottawa) are failing to look at solutions aimed at effectively addressing an overall decrease in entrepreneurship and economic activity across the nation and it is now on us, as resilient Canadian entrepreneurs, to empower those who can bring the most value to the table if we are to strive for the quickest path forward towards economic recovery and helping the average Canadian family better their quality of life. I am proud to announce that RHA Ventures Inc. has answered that call 👏 In the face of rising costs for domestic businesses in Canada and competition from abroad, RHA Ventures, an Ontario-based venture capital firm specializing in cutting-edge technologies, announced today its investment in Real Life Robotics, a Waterloo-based company designing real robots for real businesses. This investment marks a significant milestone in the development of Real Life Robotics and underscores RHA Ventures' commitment to supporting true, tried, and tested founders and Ontario’s growing startup ecosystem despite an overall decrease in entrepreneurship across the rest of Canada. “Real robots, real people, and real-world challenges are what differentiate RLR as a technology company. We could not be more thrilled to have RHA Ventures, a group of experienced founders and problem solvers, on board as strategic advisors and investors as we help elevate Ontario globally as a home for first-in-class robotics and automation technology - empowering businesses with transformative robotics solutions that unlock new levels of efficiency, reliability, and scalability,” - Cameron Waite, CEO of Real Life Robotics. The numbers clearly show that the cost of getting involved in a business or launching a new product is too high for the average inexperienced Canadian and our economy has slowed in growth accordingly. On a macro level, we are placing too high an importance on new founders in a down market when we should be rewarding and doubling down on our true, tried and tested investors, founders and legacy businesses who have shown they are willing to take the risk. Thank you, Brian Foster and the rest of the team at RHA Ventures Inc. for taking this first step of the journey with us 🙏 https://lnkd.in/gSr5TP48

63

8 Comments

I rarely share podcast episodes here. But this one is a MUST listen to both INVESTORS and founders operating in bricks&mortar hospitality & retail technology. So many true, real, no BS points Dax Harry Stebbings. 👏🏼 Be bold enough to operate with a sales strategy and approach that many VCs won’t understand or approve but that works wonders in that space and builds this amazing, sticky, powerful model that most platforms in the space can’t crack or are afraid to (because it doesn’t tick some boxes you read/hear about from the tech/VC experts) 🚀 A growth trajectory that changes and originally is not on the typical VC path but then, once the “cockroach”, groundwork is done you’re in an exciting and unique position to scale with a product market fit that’s hard to beat - PMF and growth not achieved due to endless millions raised but a real PMF that makes thing sticky, powering your product-led growth 👊🏼 Stay super close to your customers. No matter how big you become, but especially in the first 5-10 years literally speak to them DAILY. Not many manage to make it work for hospitality or retail SMEs, it’s one of the hardest group to find PMF with. But once you nail it - you’re like a constantly growing massive mountain 🏔️ - sky is limit & no one can’t move you no matter what. Don’t build businesses to please an investor’s thesis/POV which you’re currently talking to or following on LinkedIn. Build a business together with your ICP customers and bring them the most value you possibly can. The rest will follow. Even the ticked boxes that you read so much about.

13

3 Comments

Sidewalk Labs (Part of Google), another showcase of Canadian politicians bending over for a big US corp, with ZERO tangible results 💩 Roxana and I attended a "private investor demo" session in 2019. A block of wood was passed among the audience, supposedly the NEXT BIG BREAKTHROUGH in urban development! Demo concluded, by observing a piece of wood! Building blocks of future skyscrapers! The promise? With this, Google will build a "Smart City" for us, the peasants of Toronto, in Queens Quay 🏖️🏢 Sidewalk Labs' website now points to a newer Google scam, it reads: "Build Sustainably with Google Earth"! Bait and switch, but let enough time pass so no one remembers 🤢 https://lnkd.in/gd3B-a6m Guess now the investors and Ontario Government | Gouvernement de l’Ontario have shit loads of these wooden blocks, ready to shove up somewhere, to find a use for! All because the name "Bloomberg" sounds authoritative enough to our ears? Surely that's capital well spent, instead of investing in local talent! 🤔 Will Canada's tech ecosystem ever crawl out of Silicon Valley's shadow, and stand on its own? ⌚👀⛔

46

2 Comments

Acquisition offers often start by having initial conversations.   But what happens when those initial conversations evolve into something much bigger? Here's how Étienne Mérineau and the Heyday team’s journey unfolded: Etienne was approached by a product manager from Hootsuite interested in a demo of his platform. At the time, it seemed like a straightforward request, with no hint of M&A on the horizon. But shortly after, Hootsuite went silent. During this period of silence, Etienne received inbound interest from other players in the market. Some discussions even progressed to term sheets and offers, though none were compelling enough to move forward. While Hootsuite remained quiet, it turned out they were busy finalizing an acquisition of a company adjacent to Etienne's. When the news broke, he assumed they were out of the picture.   But Hootsuite had a different strategy in mind—they saw Etienne’s company as a perfect fit to build upon their recent acquisition and bolster their story ahead of a potential IPO. It wasn't until Etienne directly confronted them, clarifying that he was already in talks with other serious investors and potential buyers, that Hootsuite made their intentions clear. The takeaway from Etienne’s experience?   In M&A, timing, patience, and strategic insight are key. It's essential to remain open to all opportunities while also being direct about your expectations and goals.   It's not just about the demo—it's about understanding the bigger picture and navigating the complexities with clarity and purpose.

32

5 Comments

If you're thinking about selling your SaaS company, this is THE episode to listen to. Huge thanks to Francois Lanthier Nadeau for telling his story from start to finish with 0 holdbacks 🙌 This episode is about your power as a seller, necessary buyer due diligence steps, questions to ask your acquirer to determine cultural fit, things to do before signing the LOI, figuring out what "dream exit" means for all the stakeholders, and much more. Live in 2 weeks.

17

💡 Why Every New Founder Needs to Hear This: Real Talk About the Highs and Lows of Entrepreneurship I had an amazing time on the latest episode of Collisions YYC with Jade Alberts and Tyler Chisholm! There’s something truly special about having real conversations with these two—discussing both the highs and the lows of being an entrepreneur. 🎢 In this episode, we dive deep into what it really takes to navigate the rollercoaster of startup life—how to manage those big wins, like landing a new client, and how to push through the tough moments, like missing payroll. We shared some hard-earned lessons on avoiding the common mistakes founders make, staying grounded through the chaos, and most importantly, knowing when to keep going and when it’s time to pivot. 🌱 For all the new founders out there: This journey isn’t easy, but it’s totally worth it. Prepare yourself for the challenges, and keep in mind that the highs and lows are all part of the adventure. 🚀 🎧 Tune in to hear these raw, real, and invaluable insights from Team Awesome: https://lnkd.in/e6CKrASG 💬 I’d love to hear your thoughts—what challenges have you faced as a founder? And how did you know when it was time to pivot or keep pushing through? #TeamAwesome #KeepBeingAwesome #Koridor #Entrepreneurship #FoundersJourney #CollisionsYYC #StartupLife #YYCFounders

13

1 Comment

One of my favourite phrases in business is ‘your focus needs focus.’ It’s easy to get excited about new opportunities—starting a brokerage, investment company, or even a tech startup. And that’s great! But here’s the key: don’t spread yourself too thin. Bring in smart, capable people to help run those ventures so YOU can stay laser-focused on your main one. Trust me, when you do that, both projects will thrive. #Entrepreneurship #BusinessGrowth #mortgagebroker #Leadership #BusinessMindset"

3

SaaS tools focus on product differentiation so much they forget the one thing that actually matters... Distribution advantage. In today's Whiteboard [Thurs]day, I'm diving into: 1. How the launch of our FRMT couture line highlighted the difference in distribution advantage opportunities between DTC and SaaS. 2. How SaaS can achieve high growth using its distro opps. [ICYMI: We launched FRMT, our luxury couture line called "Style As A Service," taking ordinary pieces of clothing and blending them with timeless craftsmanship. Link below to check it out.] Aside from being an experimental marketing campaign sold through FERMÀT funnels, this venture accomplished the hardest thing in the sea of software: Being memorable. How? "Moonshot marketing" - Rabah Rahil, CMO of FERMÀT. Within DTC, the distribution advantages are a dime a dozen. You've got: ➝ Meta ➝ Influencers ➝ Riding the wave of cultural moments ➝ And so on... Within SaaS, you have fewer options: ➝ Truly fresh ideas (like an outlandish couture line) ➝ Product-driven distribution trick (+1 product that makes you want the primary)  ➝ Partner-driven distribution trick (I.e. what eBay is to Paypal) Our FRMT line has taught me SaaS has these 3 major options. So experiment within these to figure out your distro advantage and product differentiation (aside from good engineering). It's how you'll be top of mind and make a high-growth company grow even faster. For us, it's so far so good on FRMT. I'll let you know how it goes.

36

9 Comments

🚀 Our first LIVE episode is out! In this special live recording from the Elevate Conference, I sat down with Dax Dasilva, the visionary Founder and CEO of Lightspeed Commerce, to discuss Bootstrapping to a Billion-Dollar IPO. 👉 Listen to Episode 211 here: https://lnkd.in/gKga3M3h We'd love to hear your thoughts! Share your key takeaways in the comments below. #TankTalks #RippleVentures #Lightspeed #Entrepreneurship #Leadership #Innovation #ElevateConference #Podcast

10