Jenna Earnshaw

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)!

350

29 Comments

🤝 Influencer App Node Sells for $13 Million to Talent Agency Dulcedo Group, a Montreal-based talent agency, has bought the startup Node, described as an "AI-powered influencer marketing platform." If you look at influencer M&A activity, most startups are bought for either their existing relationships or their technology. In the case of Node, their 5,000 content creators/micro-influencers and their AI technology are what was attractive to Dulcedo Group. These add to a larger agency's credibility in the realm of "influencer marketing" and can help them win new clients. The ability to mention your "AI capabilities" and your existing relationships with creators are major selling points. The creator economy is one of the biggest trends in media, marketing, and advertising. There is a limited (but growing) supply of native influencer/creator-related agencies and platforms and there is a massive amount of more traditional agencies who know that they need to build out their creator capabilities. They either build that capability in-house or acquire that capability via another company. These supply and demand dynamics will shape the creator economy over the next 3-5 years. More influencer M&A is definitely on the way! #influencers #influencermarketing #creators #creatoreconomy #marketing #advertising #media #entertainment #agencies

18

1 Comment

💎 When I launched my first startup, I was convinced our product was revolutionary. I poured my heart and soul into building the perfect app, certain that users would flock to us once we went live. I had dreams of millions of users, hockey stick growth charts and our servers overloading. Man, was I in for a rude awakening 💔. The most dangerous assumption founders can make is to think that if you “build it, they will come”. Far too many founders believe that creating an amazing product is enough - that users will magically discover and adopt it. The truth? It's far more challenging. Your users don't just appear, you have to fight for every single one. 1️⃣ Building a great product is only the first step. There's a vast graveyard of products that were built but never properly distributed. These were potentially game-changing products that faded away in obscurity, not because they necessarily lacked quality, but because they lacked visibility. 💯 Founders must commit significant time, money, and energy to attracting (and retaining) users. This means leveraging multiple channels: ▪ Email marketing ▪ Content marketing ▪ Social media ▪ Influencer marketing ▪ Events ▪ PR ▪ Partnerships ▪ Community building ▪ Paid ads Each channel requires its own strategy, setup and ongoing optimization. 🔥 So to all the founders out there, don't fall into the trap of neglecting user acquisition. Start planning your growth strategy from day one. Make it as big of a priority as your product. Test different channels and approaches, double down on what works, and be prepared to pivot when needed. Roll up your sleeves and get ready to hustle for growth 🚀. It’s the only way. What hard lessons did you learn while building your startup? How did you acquire your first 100 users? What user acquisition channels worked for you? Share your experiences and insights in the comments below! 👇 #startups #growth #marketing #founders

39

21 Comments

🚀 AI-Powered Fintech on the 23% Share Rise 🚀 ... being an E-Commerce company. Earnings update 🤑 Shopify just pulled the Toronto Stock Exchange out of a 5-week slump with impressive second-quarter results. The tech sector is on the rise, thanks to Shopify's 23% share increase, fueled by its AI-powered e-commerce solutions that outperformed analysts' expectations and set a positive tone for the upcoming quarter. While global FinTech investment cooled in H1 2024, AI and RegTech are shining bright amid the uncertainty. Case in point: NCR Voyix, with a workforce of around 15,000 across 35 countries, has agreed to sell its digital banking product (serving 1,300 financial institutions and over 20 million active users) to Veritas Capital for $2.45 billion. On another note, Monzo Bank, a leading Open Banking and Neobank, just hit 10 million customers in the UK. This highlights a clear trend in how Gen Z prefers to manage their finances, and it’s a trend to watch closely. Stay tuned! #FinTech #AI #Ecommerce #StockMarket #DigitalTransformation #GenZ #RegTech

26

🚀 Summer Editions just dropped and it’s another massive release from Shopify! Just in time for editions.dev tomorrow in Toronto. Shopify is rolling out fantastic new features that I’m excited to dive into. 1. Managed Markets (formerly Markets Pro) Duties included in prices, making international sales seamless. This simplifies cross-border transactions for our merchants, enhancing global reach and customer satisfaction. The last nail in the coffin for the managed markets vs Global-e debate! 2. Search and Discovery Enhanced search capabilities allowing merchants to efficiently manage large inventories. We built a store with 1 million SKUs using this feature, demonstrating its robustness. This reduces the need for third-party search solutions, lowering costs and improving site performance. 3. Hydrogen Builder A powerful tool for building customized storefronts while maintaining ease of use for business users. Hydrogen allows us to create highly tailored and powerful storefronts without compromising on user-friendliness. This is a game-changer for merchants looking to enhance their online presence. 4. Automatically Ship to Store & Pickup instore Automatic ship-to-store and store transfers. We are already integrated to import these transfers into WorkMate, our app, and with our API into your ERP or accounting software. This unlocks in-store fulfillment for our merchants some with up to 1,000 stores, significantly unifying their inventory availability. 5. Post-Purchase POS Extensions New extensions for post-purchase processes. Increased extensibility throughout the POS system will enhance the post-purchase experience, driving customer satisfaction and loyalty. One thing we were hoping for a GA release was account extensions GA. Eagerly waiting to use that for some of our massive B2B brands we’re migrating to Shopify this year. Shopify consistently delivers features that unify their platform, ensuring consistent extensibility across all aspects. They are trailblazing the path for the trillion-dollar retail and B2B opportunity, expanding their reach as the leading commerce stack. These advancements just show the value Shopify continues to deliver as a product-led company that improves at a pace no one can compete with. Check out the latest features from Shopify Editions Summer 2024: https://lnkd.in/g4Xqd_pR #Shopify #Ecommerce #TechInnovation #ShopifyPlus #RetailTech #WorkMate #HydrogenBuilder #SearchAndDiscovery #POS #TeifiDigital

34

5 Comments

Initially, Shopify struggled to raise VC because of 1 misunderstood metric. Today its market cap is $86.5B. 😳 Investors evaluating Shopify were stuck on the fact there were already 10,000 e-commerce merchants, causing concern around TAM. But if you don't get TAM right, you won’t be able to calculate slope, which is what you’re supposed to be investing in anyway. You need to answer two questions to get that evaluation right: → Is this a trend that’s going to continue to grow significantly? → Is this a company that’s capable of catalyzing that growth? If investors had answered the above, they would have seen that the addressable market was likely to grow exponentially—and that Shopify was going to be the primary enabler of that growth. In theory, investors get it. But in practice, it's actually very hard to invest in because you have to be able to understand the dynamics of why that increase will happen. One indicator is the rate and quality of progression in a product’s service, particularly if you're a user of a similar product. AI is a great illustration of how this is happening right now. Its progression rate is astonishing. If a service provider's service is getting better over time, you should invest in it with the assumption that it’s progressing exponentially. That's why I'm bullish on Notion right now. The way they've implemented AI indicates that as AI improves, Notion will accrue increasing benefits. Take their recent announcement that inside Notion, users can call on their other apps for information, reinforcing themselves as the front page of where you do work, making it your OS. I break it all down in the video below. Comment any topics you want me to cover for future Whiteboard Wednesdays. 

31

9 Comments

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

8

Weekly Update 8.2.24 ⚡ • One month ago, I posted about how we shifted our operating cadence to better manage the tension between dedicated deep work time vs. managing increased merchant onboarding volume as we scale our Shopify App. A few shifts we made as an organization: 1. Engineering cycles — 2 week sprint on new functionality, 1 week focused on maintenance/tech debt. This ensures we continue shipping at a face clip while dedicating 1 week towards housekeeping. So far so good. 2. Dedicated deep work time — Jennifer is leading the charge by carving out 9 am - 1pm on select days for sacred deep work time, allowing her to focus on her top priority. Others on our team will follow lead by carving out dedicated deep work time and silencing notifications during these hours. I'm delinquent on this! I'll follow suit on this next week. 3. Product-led engineering — we've been inspired by companies like PostHog that champion product-led engineering and people like Arnaud Lassignardie, who takes extreme ownership. Our engineering team at TryNow increasingly makes product decisions, interfaces directly with merchants, and pulls forward our product roadmap. Typically, Product Managers define the "What to build" and Engineers define the "How to build." At TryNow, we're increasingly relying on Engineering to define select components of the "What" in addition to the "How." This level of ownership makes for better products. Josh Rathke, excellent work leading the team in this shift! • Onboarding Ian Schneider, Director of GTM at TryNow.com. Grit and Empathetic Leadership are two core value of ours at TryNow. Ian is as gritty as they come and leads with empathy. He's off to an electric start — 8 new deals created in week 1! ⚡ 🔥 • We're onboarding brands across a variety of new verticals (#TryNewThings): pajamas, fine jewelry, color cosmetics, streetwear, bedding, wedding dresses, and premium sandals. #TryBeforeYouBuy #TryNewThings #Shopify

31

2 Comments

“The best product doesn’t always win. But the product that’s heard and seen the most? It often does.” A Canadian founder I recently spoke with was all-in on “hiring slow”—so much that he was stuck in analysis-paralysis. He’d review ROI data constantly, yet avoided ads entirely because he believed the returns weren’t high enough. And while he was focused on product quality with constant RnD.. It led to one big problem: no one knew it existed. I realized his issue wasn’t the product, or even the ROI—it was that no one saw his product. "When no one knows you exist, they can’t choose you." Here's what I told him: "You can have the world’s best product, but without visibility, it’s not going to move." This is where so many founders get stuck, pouring effort into perfecting their offerings without realizing that action and visibility are just as critical to success. If you feel trapped in *“action coma,”* endlessly analyzing without results, it’s time to flip the switch. Slide in my DMs.. And I’ll share what I’ve learned over 8.5+ years about consumer behavior and the psychology of purchase and how to connect with your customers on the channels that count. .................................................................................... Download my free Guide below to stop Inaction and Make the best Strides forward! #GrowthMindset #FounderTips #ProductMarketing #theRealGyan #MarketingStrategy #FounderGrowth #ProductVisibility

4

6 Comments

📈 It’s More Challenging for Immigrant Founders: Why "Founder-Environment Fit" is Crucial Before Product-Market Fit Starting a business is challenging for any entrepreneur, but immigrant founders face additional hurdles. Beyond creating a product that fits the market, we must first find the right founder-environment fit—an often overlooked but essential step in the startup journey. This chart highlights the path to growth for startups, showing that immigrant founders need to find environments where their ideas and ambitions can thrive before even thinking about product-market fit. Without this alignment, scaling becomes even harder. 🚀 Why Founder-Environment Fit is So Important: - Immigrant founders often face challenges like limited networks, unfamiliar business landscapes, or legal barriers. - Finding the right environment helps lay the foundation for success—only then can founders focus on building, scaling, and reaching maturity. Immigrant Founders Who Found Their Fit: - Jason Huang (NVIDIA): Taiwanese-born, co-founded NVIDIA, which became a leader in AI and graphics technology, with a market cap of over $3 trillion. - Elon Musk (Tesla, SpaceX): South African-born Musk built Tesla and SpaceX into world-changing companies, now valued at over $900 billion combined. - Sergey Brin (Google): Russian-born, co-founded Google, which handles over 90% of global search traffic. - Jan Koum (WhatsApp): Ukrainian immigrant whose messaging platform WhatsApp was acquired by Facebook for $19 billion. - Hamdi Ulukaya (Chobani): From Turkey, Hamdi turned Chobani into America’s top-selling Greek yogurt brand in under five years. And many more... Key Stats to Highlight: - Immigrant founders have created 55% of U.S. unicorns (startups valued at $1 billion or more). - Immigrants are 2x more likely to start a business compared to U.S.-born citizens. Empowering immigrant founders is essential—not only by providing resources but by fostering environments where they can thrive. By breaking down these barriers, we can support the next wave of innovation and progress. #ImmigrantFounders #Entrepreneurship #FounderFit #EmpowerDiversity #StartupSuccess #InnovationJourney

107

16 Comments

Important fact about most startup (and VC) success stories. It is convenient to overlook this, but the best companies and products are not built on any specific timeline. The best people win, and that is the only thing that has consistently and repeatably truly won over the test of time.

39

1 unexpected advice a founder gave to my startup When I just started hanging out with tech founders in Toronto, there was one advice an exited founder gave me. First I smiled, then immediately followed it. Record your calls with people and watch it. Why? We screw up 90% of our potential with our own communication style. Might be the most cringe and worthy exercise ever. “Basically’ “yeah no”, “no ya”, not being able to directly answer a question and sooo many more surprises. Communication is everything, especially in an early startup. Not smart podcasts and books (oh no how so😂?) ⚡️Follow me for unfiltered advice on your career and startups⚡️ Shoutout to Shopify & Jocelyne Murphy for hosting cozy pitch afternoons at Shopify office.

69

1 Comment

🥂 Exciting news! Novel is opening our Partner Program to the public!😮‍💨😮‍💨 Something surprising I've discovered this year is that nearly everyone knows at least one e-comm brand owner or marketer personally. Unsurprisingly, the largest Shopify Brands on Novel have come from referrals. People try & buy from people they trust. Time to start rewarding Novel's unsung evangelist! Heres how it works: - Sign up for free: https://lnkd.in/epXqXuCE - Receive your own unique link for sharing to other brands. - Promote your link; email, social, directly to brands. No need to intro Novel. - Get 30% of ALL revenue from every brand who installs using your link. - Track brand installs and commission payments in your personal dashboard. - Pull commission money directly into your bank account, every month. With recent platform updates, Novel's onboarding is a now a 30second self-serve process, so it has never been easier for brands to quickly give us a try. Shopify apps don't typically do this but I have a really good feeling about it.

24

1 Comment

I’ve noticed many founders don’t realize how much non-dilutive capital is flying under the radar in Canada. So I’ve shared a list of alternatives you should know about before choosing to raise capital: 1. Business Scale-up and Productivity (BSP): BSP provides funding to help you scale your operations and increase your market reach. It’s a great way to drive growth without sacrificing equity. 2. Industrial Research Assistance Program (IRAP): IRAP offers financial support for research and development. It’s perfect for taking your technical ideas to the next level. 3. Scientific Research and Experimental Development (SR&ED): SR&ED provides tax incentives for technical development. It’s one of the most generous programs in Canada, helping you reclaim a portion of your R&D costs. 4. FedDev Ontario: If you’re based in Southern Ontario, FedDev offers funding to help businesses scale, innovate, and compete globally. It’s a solid option for companies looking to make a big impact. 5. Canada Small Business Financing Program (CSBFP): This program helps small businesses access loans for purchasing or improving assets like equipment or property. It’s designed to help companies grow and invest in their infrastructure. 6. CanExport SMEs Program: If you’re looking to expand into international markets, CanExport provides funding to cover costs related to market research, business travel, and participation in international trade events. 7. Canada Media Fund (CMF): For those in the digital media industry, CMF offers funding for the development, production, and marketing of innovative media projects. 8. Ontario Centres of Excellence (OCE) Programs: OCE offers various funding programs aimed at driving innovation and commercialization in Ontario. Their programs often focus on collaboration between businesses and academic institutions. 9. Mitacs Accelerate: This program provides funding to support research internships, allowing companies to collaborate with universities to solve specific challenges while benefiting from academic expertise. 10. Strategic Innovation Fund (SIF): Targeted at larger-scale projects, SIF offers funding to support R&D, commercialization, and the growth of innovative businesses in Canada. 11. Women Entrepreneurship Strategy (WES) Ecosystem Fund: This fund supports organizations that help women entrepreneurs grow their businesses. It’s part of a broader effort to increase women’s participation in the economy. 12. Innovative Solutions Canada (ISC): This program helps Canadian startups by funding R&D projects that address government challenges. It’s a great way to secure funding while working on real-world problems. 13. Alberta Innovates: For businesses in Alberta, Alberta Innovates offers several funding programs to support R&D, commercialization, and business growth. They focus on fostering innovation in sectors like energy, health, and technology. Have I missed any?

16

3 Comments

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.

14

2 Comments

A lot of Canadian founders are getting robbed. Yup, you read that right. If you’re a founder that: 1️⃣ Generates revenue in USD 2️⃣ Or, has raised USD funds and if you’re operating in Canada, chances are you need to convert some of those USD funds to CAD to pay your operating expenses or if you’re lucky, maybe you have a cash balance that you want to put away in a GIC for some nice interest. Founders: how are you currently converting your currency? I love our Canadian banks, don’t get me wrong, but they take a massive bite out of your profits when it comes to foreign exchange. DO NOT TRADE CURRENCY WITH YOUR BANKS. Sorry to all my bankers reading this! I know so many founders who learned this lesson the hard way and hopefully this post will save a few of you from making that mistake. Moral of the story? Go find yourself an awesome FX trader. Of course, happy to introduce you to ours (no benefit to us, I just want to help our start-up ecosystem in Canada WIN!)

150

83 Comments

Wonder why Alexandre L. and I get along so well? We use Pluvo. ☂️ I’ve said it before, and I’ll say it again. If you want your business to succeed – you need a solid financial plan. A bulletproof financial plan is going to: 🤔 Remove guesswork from your decision making  🔥 Reduce friction between leaders in your organization  🔋 Improve your organizational health Pluvo makes sure that CFOs and CEOs are on the same page, unlike any other product on the market. Give Pluvo a try, and see how a good financial plan can turn your business into a great one. See more on our website! 🌧️ #financialplan #fpanda #fintech 

38

1 Comment