Yaz Sinan

"Entrepreneurship is painful and sometimes rewarding." This quote naturally came out during a check-in call with my good friend and fellow entrepreneur, Gilad, who is building a great product at Sequence (I just wish they were available in Canada) 😢 As soon as I said it, both Gilad and I reflected on how true that statement is in describing the journey of building something. Shoutout to all the business owners and entrepreneurs out there taking the pain with a pinch of reward. #startupjourney #pain #entrepreneurship #grit

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Who better to talk about Shopify's trajectory and future than Benjamin Lang • OLY.? In our 50th podcast episode, I had an extremely interesting conversation with Benjamin about a lot of awesome topics that are close to my heart, and I can't be more excited about what's happening in the Shopify ecosystem. For example: • B2B features • From only online commerce to commerce in the more broad sense of the word • The focus on TCO • Customer centricity I'm very grateful I had the chance to talk to Benjamin, and I hope we can do it again some time in the near future as things are moving so fast. Thanks a lot for your time and effort Benjamin! #deardigital #shopify #podcast

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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 👇

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Over the weekend, Tobi, the founder and CEO of Shopify, discussed the major reason investors passed on Shopify in the early days : market size. I remember that financing round, & I remember having the same concern, & making the same mistake. Living in the valley & driving on 101, the billboards & logo-adorned headquarters of successful companies provide a daily infusion of all the mistakes in I’ve made in guessing how a company or a market might evolve. Years later, I listened as Bill Gurley shared his thoughts about market size. He asked himself a question : whether the startup was increasing, decreasing, or maintaining the market size? (I can’t seem to find the link - but I have it in my notes!) I added that question to my diligence list when meeting startups. Now much later, having seen many companies create categories or reinvigorate aging ones, the question I ask myself has evolved. It’s not as the market size large enough? Instead, it the question is : do we believe this company can create the market? Market size is the output of all the players marketing, selling, building. Their efforts alter, distort, & juice the supply/demand curves of macroeconomics. It’s not a given - not an output or a steady-state CAGR. Often it’s the startups that engender the demand, change the market dynamics, & make markets massive by taking risks with products. When done right, these founders create category-defining businesses like Shopify (now worth $90b)!

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We wrangled our whole team to Ottawa to celebrate Downpay's 2 year anniversary 😭 I can't believe how far we've come. Downpay's first year was Denis and I figuring out our MVP and finding the core problem we wanted to solve. In August of 2023, we publicly launched Downpay on the Shopify App Store. Fast forward to today and it's insane how far we've come. ✨ 6+ team members have helped... ✨ 800+ Shopify Brands process... ✨ $40M+ extra GMV with partial and deferred payments. 😍 Not to mention metrics I'd never thought I'd see in my #productmanagement career. ⭐️ + 47% checkout conversion ⭐️ + 25% AOV bumps ⭐️ + 30% increase in online sales ⭐️ Millions in GMV processed in less than a day, TWICE I'm so incredibly lucky to be on this journey with all these amazing humans who have the best laughing faces. Denis Zgonjanin Ian Kelly Brittney Oberfeld Jeremy Hanson-Finger Alain Achkar BFCM, Holiday season, 2025, we're here for it! 💪🏻 Let's go. 🚀 #shopify #startup

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The 2024 Future of Work list highlights the next generation of startup companies that are revolutionizing the way we work. 3.4 billion workers show up for a job every single day. Most of those workers are unhappy, underpaid, and underappreciated. The Future of Work has now become an existential topic for companies around the world. Over the last decade, public Work Tech companies such as Workday, Atlassian, and monday.com have enabled companies to do more with less, automated repetitive tasks, and collaborated seamlessly across geographies and time zones. The companies recognized on the 2024 Future of Work 100 have raised a cumulative $30 billion in venture capital financing, with a total valuation over $140 billion. The ranking is represented by companies across 17 countries including Australia, Belgium, Canada, Chile, China, France, Germany, India, Israel, Japan, Netherlands, Singapore, Spain, Sweden, Switzerland, United Kingdom, and the USA. Airtable, a low-code platform for building collaborative apps, tops the 2024 list. The 2024 Future of Work 100 honorees showcase the diversity of WorkTech companies and highlight strong market capitalization, increased efficient growth, and a newfound focus on profitability. In addition, artificial intelligence (AI) has emerged as an important theme with 93% of the recognized companies have implemented AI capabilities across their product lines. Business Wire #futureofwork #worktech #collaboration #startups #venturecapital Acadian Ventures

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Just had to share this gem from Collision Conf in #Toronto. Among the #startups and VCs, I spotted a guy with a shirt saying, "Ask me about my CAC." Naturally, I asked. Sebastian Fallenbüchl, BASc., the wearer, shot back, "My CAC is getting lower as you just approached me." Genius. Seb’s witty remark was more than just a laugh — it was a reminder that business is about people. Metrics like CAC are crucial, but so are the connections and conversations that drive them down. Takeaway? Be #approachable. Humor and humanity can make all the difference. Thanks for the insight and the laugh, Seb. Here’s to more moments like these! #Networking #BusinessInsights

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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

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Stop paying "fundraising advisors" $10K to teach you how to beg VCs. The raw truth about fundraising that most Canadian founders won't tell you: "Stop chasing VCs. Make them chase you." Why? Because the founders winning at fundraising aren't playing the typical Canadian "wait and see" game. They're rewriting the rules. This Thursday: Joining an exclusive breakfast with Toronto's top seed & series A founders who've collectively built $200M+ in value. Including: a founder who scaled to $15M ARR in 24 months (with their exact playbook). At our last breakfast, we broke down: • Why chasing VCs kills your leverage • How to create genuine FOMO (not the fake kind) • The exact timeline to close rounds faster • Why Canadian founders need to stop being so "nice" • How to make investors compete for your round The reality? Most Canadian founders are leaving millions on the table by: ❌ Letting VCs string them along ❌ Playing the endless pitch game ❌ Losing momentum in drawn-out processes ❌ Not setting hard deadlines ❌ Missing the power of compressed timelines Top founders? They're flipping the script: ✅ Setting their own deadlines ✅ Compressing investor meetings into 1-2 weeks ✅ Building businesses VCs can't ignore ✅ Creating authentic momentum ✅ Leading rounds, not begging for them Qualification: • $1M+ ARR or raised Want the unfiltered playbook? 💡 Comment if you: • Hit these numbers • Know someone who has • Want to nominate a founder Invite-only. Limited seats. Location shared privately. No BS. No theory. Just real founders sharing what's actually working right now. Virio Toronto Tech Fest Aceocial Max Woo 👋 #TorontoTech #StartupCanada #VentureCapital #Startups #Fundraising

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Nobody launches Consumer brands because they're obsessed with building a tech stack. Most of the time, people launch Consumer brands because they have a passion for their space, or a story to tell. And luckily the Shopify ecosystem made it so that any artisan can sell anywhere, and any consumer can buy from any artisan. It's beautiful—and I want to make it even more accessible for shops. They won't have the same ad budgets as legacy brands, but we may be able to give them something else. See, I used to work at Turo. There, we had access to funding, tech, and software in ways I didn't realize were possible beforehand. As a result, we grew—fast. I saw first-hand what being so well-resourced like that did for our business, and now I want to do the same for artisans globally. That starts with data. I want to give the tech all the big players use, to everyone. It will level the playing field—at least with data—and make ecommerce a meritocracy, not a game of budgets. If we make data a commodity, ecommerce as a whole is better off. That's our mission with Polar Analytics, so follow along if that sounds interesting!

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This is a really good post by Ghassan Halazon. It's easy for armchair quarterbacks to say "Canadians sell our companies out too early", or "we don't think big and therefore sell out early", but it's never that simple. I don't agree with Ghassan that first-time founders should always take the offer (eg. Google could have sold to Yahoo in 1998, and I'm sure Shopify had multiple interested suitors on their path to an IPO), but he's probably right in most situations. The first exit I had as a VC was a 5x return over about 4 years. I recall the negative comments I received from people in the ecosystem that we sold out too early to the Americans (Microsoft was the acquirer), and that we weren't thinking big enough. But none of those critics saw the slowing sales pipeline, or the increasingly competitive sales cycles, or the churn rates, or the difficult fundraising. No matter how good things are, there are always risks to the business. Most companies plateau long before they achieve a market dominating position, and distinguishing between approaching that final plateau vs. just a slowing blip before the next growth wave is difficult for entrepreneurs that are usually 'half-glass-full' people. And, on a related point, despite what many say, it is never that companies sell out early because they lack the access to capital needed to scale. They may lack capital at a valuation they desire, but that's different, and in fact a datapoint on where a business is on its path to plateauing or market domination.

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Hamish McKay has run an absolute masterclass of building in public. Building in public can be controversial, especially if you’re in a market with a low barrier to entry (the Shopify App Store) and you’re fully aware that a few ankle biters are incentivized to grab some of your nascent market. However, in a platform-based ecosystem, it’s understandable and even necessary. If your whole company depends on a third-party platform to be a viable business, you have to be really careful of your primary vendor becoming your primary competitor. My hypothesis? To be taken seriously by enterprise customers, Shopify is continuing to clean up the App Store and quietly removing unmaintained or low-quality apps. I’d also bet that there are going to be a new tier of apps along the lines of, “Shopify Basics," so that new enterprise merchants don't feel like the only way to take advantage of Shopify is layering on a pile of apps. Everyone knows Amazon Basics, right? Amazon uses their treasure trove of consumer data to identify popular products and create a generic line of equal or better quality offerings. Batteries, binders, and bookshelves are all sourced, manufactured, and sold by Amazon directly. Amazon chooses the products to source and sell themselves based on data from the vendors who took the risk of selling on Amazon. We’ve all heard of the handful of large brands who refuse to sell on Amazon - or if you’re Walmart, go so far as to refuse to consider vendors who use AWS for their infrastructure. (Spoiler alert... Amazon never needed you to sell on their platform to identify market trends, they just learned about your margins.) I imagine Shopify has a few highly-paid MBAs in their strategy department combing through app store data, segmenting the data by merchant size, billing volume, or even API usage to determine which apps gain the most traction among merchants. Then, they make the decision whether to build, buy, or ignore. Hamish has set himself up to be bought by Shopify, and I bet it happens sooner rather than later. If Shopify simply rips him off, they send a very public message to the app development ecosystem that will stifle ongoing innovation. If they buy him, similar to their other acquisitions, they remind the ecosystem that you too can get rich by taking on the risk to build in this ecosystem. For us, our primary risk is the Shopify Search & Discovery app. It’s a phenomenal app and eliminating the need for apps like Boost Commerce, Fast Simon, and SearchSpring. Why pay a third-party app for functionality that Shopify offers for free? Our business risk is further amplified by sitting between not just one, but two platforms: Shopify and Google - who are actually partners! We get to watch the innovation (aka competition) happen in real time, and our success will depend upon who can build and maintain better AI-powered search algorithms for large merchants. Based on the AB tests we’ve run, our bet is on Google.

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Here's a brief demo of KOTS, the first of fifteen new products from our team at Mindlace

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Last week, Zach and I visited a large partner rolling out Yembo across 400 locations in the US and Canada. We spent the entire day with them, working with their teams to understand their workflows. It wasn’t just about integrating Yembo. It was about: → Identifying gaps, → Fine-tuning our product to streamline processes, → And setting them up for long-term success. We met with their executive team, diving into their future vision. ↳ We outlined specific initiatives, ↳ Shared Yembo’s future direction, ↳ And presented a roadmap showing how we’ll power their growth. At Yembo, our mission is simple: Make our customers' lives easier. We’re focused on building partnerships where we can add real tangible value. -- At Yembo we use AI to make property inspections easy using smartphone photos and videos. Our virtual surveys provide photo ID of each item, streamlined guided video calls, built-in estimating, and the platform gets new features shipped each week. If you're a moving company, book a demo here: https://hubs.li/Q02PjX_g0

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Deep Pockets Over Party Rounds It's YC demo day in 2 weeks and fundraising around the Summer 24 batch is already at fever pitch. Many founders are experiencing a lot of demand and it's tempting to raise a bunch of money from lots of small checks. I'm biased but if you are lucky enough to have plenty of interest, I suggest you engage those with deep pockets. 1. Most Companies Need More Money. Regardless of your momentum now, most companies end up needing a little more capital to reach the next round. If you've only raised from angel investors, they most likely won't be able to add much more to their position. 2. Term Sheet Minimums. Plenty of lead investors will ask for a minimum amount to be raised for the next round to close and for them to wire the funds. If your cap table has funds who can participate at the later stages, this relieves a lot of the pressure to fundraise beyond securing the term sheet. 3. Investor Network. Most funds are measured by who invests in their companies after they do and at what price. So your fund investors are heavily incentivized to help you fundraise your next round, if they've invested a large enough check. #startups #fundraising

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If I was an A player / high performer seeking employment right now, I'd look for jobs at organizations running one of these business operating systems: Scaling Up: A Gazelles Company, Metronomics, or EOS - Entrepreneurial Operating System. There are several reasons for this: -Core Values-Driven CEOs: Many will have CEOs that actually live their company core values (and insist everyone else does, too), giving you the best chance possible to thrive -A Player Team: Because these organizations are more likely to use Topgrading to hire, you'd be part of a drama-free, A Player team (do not underestimate the importance of this; if you've had bad team members or have been dismayed by workplace drama, you understand) -Get Paid More: Compensation will likely be at the high end for your role because these organizations understand the value the A Player creates -5D Focused Leadership Teams: Leadership teams are focused on Overcoming the Five Dysfunctions of a Team, resulting in less workplace politics (doing the wrong thing for the wrong reason) and way less stupidity from leaders All of these things will result in the most fulfilling working environment you've ever had. Remember the "Great resignation"? That may as well have been a myth to my clients. Why? Nobody leaves an A player team. NOBODY. That was a problem for companies that don't live there core values and that tolerate B and C players. Unfortunately, there isn't a public list of these companies. That would be one incredible A Player recruitment website. But there are a few things A players can do to find these employers: 1. Reach out to the organizations above to find out if they know of companies in your area using their systems/tools 2. Reach out to your local chapter of Entrepreneurs' Organization or Young Presidents' Organization - that's where the self-aware leaders using these systems/tools congregate ***Important interview question all candidates for all candidates to ask: Is your CEO a member of EO or YPO? Self-aware leaders tend to join these peer learning associations, and that's the kind of leader you generally want as an employer/leader.*** 3. Reach out to Metronomics, Scaling Up, or EOS coaches in your area to find out which of their clients is currently hiring. I'll be posting some of my clients' open positions - as well as background on the company - here in the near future. Find a company that is deserving of your behavior and talents. #Metronomics #ScalingUp #EOS #Hiring #JobSeekers #Jobsearch #employerofchoice #topgrading #fivedysfunctionsofateam #corevalues #YPO #EO #Grovertalent #talent #Aplayers #Aplayerhiring

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How can a startup effectively balance fundraising and growth when the two are sometimes at odds? In our latest episode of DIB Innovators, I chat with Matt Shieh, Co-founder and CEO of Canopy Aerospace who dives deep into this crucial topic. Matt shares his strategic approach to managing fundraising efforts while ensuring sustainable company growth, especially in the challenging and particular environment of the DIB. He discusses leveraging startup accelerators such as Polsky Center at the University of Chicago and Techstars for networking opportunities and investor introductions, and highlights the importance of understanding customer problems to create effective defense solutions, allowing that to guide your mission and path. Tune in to hear Matt's invaluable insights and learn how Canopy Aerospace is navigating the competitive landscape of the aerospace industry! Full episode: https://hubs.li/Q02Qvjpq0 🎧 Listen on Apple: https://hubs.li/Q02QvjKK0 🎵 Tune in on Spotify: https://hubs.li/Q02QvlBw0 📺 Watch on YouTube: https://hubs.li/Q02Qvjg10 ✍️Read our Blog: https://hubs.li/Q02Qvjpq0 John M. Howard Eric Shu Meghan Welch Decisive Point Caruso Ventures Industrious Ventures Mana Ventures Fulcrum Venture Group Techstars Colorado Office of Economic Development and International Trade Douglas County Economic Development Corporation #spacetech #defenseindustrialbase #SMBsintheDIB #cybersecurity #nationaldefense #defensetech

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Two weeks ago I travelled out to Montreal and did my first “talk” (I wasn’t supposed to give a talk) at Evolving Web’s EvolveDrupal event. A few things I comfirmed about myself: 🦸‍♂️ I’m not scared of talking in front of people. Like at all. I truly love being a showman and I may have missed a speaking or acting calling earlier in life. Who knows maybe I’ll start doing it now. 😂 I lead with Humor. I always have in my daily life. I love making people laugh but it was interesting to see the rapport build quickly even in a group setting using humor. 🤡 I believe that edifying yourself and then quickly letting people know you don’t have all the answers is the fastest way to build trust. Everyone can talk about how good they are at something but few will talk about the things they are bad at, and in the end, I personally tend to trust the people who are aware of what they can and CAN’T do. 😳 The notion of “do it scared” has always been an interesting one for me. Mainly because I don’t get many options in life to do things that actually “scare” me anymore. So doing this even though I was anxious was a great way to confirm the “do it scared” notion is accurate and I’m better off for it. Ps. This photo was probably taken after I first realized that the deck I worked on the night before and the animations I created weren’t going to work so… improv it is. #speaking #conference

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What's an "Outreach Cocktail"? Well, it's kinda like a Molotov Cocktail but meant for effective cold outreach instead of the streets of San Andreas. (s/o all my GTA players out there) So what are the ingredients for an "Outreach Cocktail"? Easy... 1. Timing 2. Relevance 3. Humor How do you use it? Whether it's a cold call, email, or DM - you're going to want to mix all three ingredients in your message to hook your prospect's attention and generate enough interest. Here are some examples for each... ⏰ Timing: A trigger that identifies when is the optimal time to reach out - Hiring for a new role - Evaluating one of your competitors - Released new 2025 initiatives on a press release ✨ Relevance: Why does your product/service address their situation - Because they could be having trouble sourcing candidates - Because they could need a lower-cost provider compared to your competitor - Because they could see road bumps with compliance to achieve their 2025 goals 🤡 Humor: Just have fun with it - There is no magic bullet or one "line fits all" here but the point is to be creative and let your personality shine. - If you're on the phone crack a joke, if you're DMing them send a gif, etc... Try making this cocktail yourself and let me know how it goes. But be cautious... it's highly explosive.

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