Jenna Earnshaw

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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Canadian Founders Shouldn’t need to leave Canada. We need to fix our system. 🍁 Last week I was catching up with a founder from Canada. She had just returned from spending 3 months in SF. She said it was insane how the entire ecosystem there is built to incubate and launch startups but then also support them for the entire lifecycle through Series A and beyond.  In Canada we’re ok at getting companies started but then we have little support beyond that and we ultimately lose them to the valley. Her suggestion was to take all the money the Canadian government is throwing at our tech sector, and instead use it to send our Founders to SF for 3 months for a Founder crash course. As a Canadian, hearing that is super depressing but also accurate. My roadmap at Developer Capital is to find and fund great Canadian companies in the pre-seed and seed round, but then get them into the US for their Series A. Why? Valuations are better, risk appetites are sharper and it will help your sales when breaking into the US market. How can we as a country support them and encourage them to stay in Canada? The Challenge: Canada’s Startup Ecosystem is Broken 💔 If we don’t want to lose our brightest founders to the US, we need to re-evaluate our approach. We need to provide the SF experience right here at home. Here’s what we can do: ⚫ Access to capital. Yeah, im sure you’ve heard this before. Pre-seed doesn’t exist in Canada. Developer Capital is trying to change that but we’re only one firm. There needs to be more deal flow sharing amongst the pre-seed and seed stage funds. This one’s on us in the VC community. We can do better. We can share our deals. We can get out in the world more and meet Founders. Rather than waiting for others to validate our own opinions we can lead rounds and be first money in. ⚫ Ecosystem support. It’s pretty nuts the difference this one makes. When a company comes out of SF they instantly have access to a network of 1000’s of early adopter companies to go out and buy their product. And the VCs who invest ask all their Portcos to take a deep look at buying these great new products. Incestuous? Yes but it works, and gets these start ups to millions in ARR fairly quickly. ⚫ The right infrastructure: Accelerators and incubators sometimes get a bad rap, but the good ones do the job of acting like a bootcamp to get your company launched, understand how to get financed, and then how to iterate until you find product market fit. Canada needs to up its game and come out with a couple of AAA accelerators. If McGill is the “Harvard of the North” why can’t Canada have a “YC of the North”? I’m not pretending to have all the solutions. This is clearly a “hard problem to solve”. But as a proud Canadian I know we can do better and I want to be able for our best companies to stay here forever (whatup Shopify). We have the talent and the ideas; now we need the infrastructure and the networks to match. Let's make Canada a powerhouse! 🍁 🚀

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Would you move your startup for $10+ million benefit + 50% ish cap gains tax to the 🇺🇲? I did it before, why not again? #SiliconValley "Budget capital gains changes are a tipping point for Canadian #startups: survey." MaRS Discovery District, Communitech, Invest Ottawa survey of #Entrepreneurs and Founders. Canada is a great place to incubate companies with a huge quantity of early stage private and public capital and terrific policy support. So why go anywhere else as a founder once you have incubated in such a great place for entrepreneurs? #capitalgains, capital gains, capital gains. That's what this video is about. Thank you to Krista Jones and Christine Bomé and all my friends at MaRS DD for leading from the front. This survey gave me hope that Canada will once more be able to be an innovation champion. Please read the survey! https://lnkd.in/gqMm6yu7

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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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Today at Antler VC Toronto, we had Michael Kravshik, CPA, CA, the founder of LumiQ come speak to us. The cohort is in week 5 of the 10-week residency. We’re still very much in the process of solidifying our cofounders and searching for product market fit. So Michael’s speech was timely, informative, and inspirational. Here were my key take-aways. 𝐎𝐧 𝐟𝐢𝐧𝐝𝐢𝐧𝐠 𝐩𝐫𝐨𝐝𝐮𝐜𝐭 𝐦𝐚𝐫𝐤𝐞𝐭 𝐟𝐢𝐭  🔸 Ideas don’t matter, the iterative test approach does; it’s more painful in the present but saves you lots of time in the future 🔸 Start with really broad assumptions, start validating those broad ideas, and then through the process of speaking to customers to get to the really narrow concepts 🔸 At one point Michael and his co-founder went through invalidating 25 ideas, which would seem discouraging but they grew and developed a lot through this process (even though they didn’t know it at the time) 🔸 At one point they did a mind-boggling 500 one-on-one interviews in the span of 6 weeks 🔸 The only sustainable advantage you can in a startup is knowing your customer better than anyone else 🔸 PMF is a moving target 🔸 PMF is treated as a verb at LumiQ 𝐀𝐝𝐯𝐢𝐜𝐞 𝐅𝐨𝐫 𝐅𝐨𝐮𝐧𝐝𝐞𝐫𝐬 🔸 Be curious, open-minded, and be willing to kill your babies 🔸 If you keep going, you will eventually create your own luck 🔸 Lots of people get stuck in sunk-cost fallacy land, but you should listen to your gut and pivot when it doesn’t feel right 🔸 Founders have a reputation for being like cockroaches, and rightfully so, shamelessness can take one quite far I also asked Michael during the QA on what his emotionally compelling reason was for overcoming so many challenges to get the company to where it is today, and his answer was really insightful and relatable. He said that 𝐛𝐞𝐢𝐧𝐠 𝐚 𝐟𝐨𝐮𝐧𝐝𝐞𝐫 𝐢𝐬 𝐚 𝐥𝐢𝐟𝐞𝐬𝐭𝐲𝐥𝐞 𝐜𝐡𝐨𝐢𝐜𝐞, 𝐧𝐨𝐭 𝐚 𝐜𝐚𝐫𝐞𝐞𝐫 𝐜𝐡𝐨𝐢𝐜𝐞. Furthermore, if you’re not crazy AND stupid you probably shouldn’t do this! Thanks for bestowing your wisdom on us Michael Kravshik, CPA, CA and I hope I captured your words and sentiments correctly! 😃 #startups

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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. 

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On Tuesday I caught up with Brandon Kuipers, one of the founders of Zox.    They have sold almost 10,000,000 products on Shopify since starting the business in 2011.   But they have been running into a problem: Like many stores, they offer hundreds of products and customers get overwhelmed and can't figure out how to find the products that are right for them.   They have solved their problem using an Octane AI smart quiz.   Here's what really stood out to me: ✅ Their quiz has solved decision paralysis for over 50,000 people so far. ❤️ Customers are loving the AI quiz, even sharing their results with each other. 🤖 The AI quiz asks shoppers a few questions, most of them free form where the shopper can type anything, and then it uses AI to write a personalized message to every single shopper and helps find them exactly the right handful of products that they will love out of the hundreds of products on the store. 🚀 They hadn't been able to make a quiz previously because they are constantly adding new products to their store. The AI quiz automatically updates itself with any new products without the Zox team needing to do anything special. ⚡ They made this quiz on vacation in just a few hours, most of which was just them thinking about what questions they wanted to ask in the quiz. I'm really excited about our AI quiz option on Octane AI. It's not our most popular quiz type just yet, but for some brands it is making previously impossible experiences possible.   We have a lot of plans for improving our AI quiz technology, we're overflowing with inspiration. I can definitely imagine a world where your quiz is creating itself (we already do this actually), automatically improving itself, and forming more and more personalized bonds with each customer.   What do you think of AI powered quizzes?

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Try more things. Fail more often. Learn faster. Burn brighter. Plant more gardens. Launch more startups. Make more babies. Build more community. Help others do the same. This is effective opportunism. Pronoia & Purpose. E/opp is a better meme than Hiis. Just as inspiring, but more secular. Gender neutral vs. male-coded. More conjectural, less prophetic. E/opp is building & growing your mind & body. Building & growing startups. Building & growing families & communities. Effective Opportunism.

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Fundraising is a Tactic, Not a Goal. It’s time for founders to revaluate the pursuit of funding. Don’t get me wrong, raising capital is a milestone for a startup and can dramatically change the trajectory of your business. It’s also challenging to pull off — everything from your approach to how you sell it, to just some luck around the timing of the deal relative to what else investors have seen all has to go in your favor. But don’t treat it like your goal — a founder that optimizes for fundraising above all else is likely not spending enough time on their customers or product. As Paul Graham says, the defining characteristic of the best founders is that they are relentlessly resourceful. Scott Belsky puts it slightly differently 👇 👉 Check out my free newsletter for more insights: https://lnkd.in/dKZQKHg2 . #starrtups #funding #founders #investors #funding #founder #fundraising #VC #venturecapital #entrepreneurship #entrepreneur #angelinvestors #venturecapital #pitchdeck

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Sometimes startups are just too early. Essentially, their product vision is too far ahead of a future market shift. When we introduced our Fractional Office product (Flexday Suites) to Canada in June 2022, most landlords scoffed at the idea of accepting private office bookings by the day. One landlord exclaimed: "An office will never be rented on a daily basis - we are not hotels." Landlord views changed when we brought customer demand and launched our proprietary FlexServe technology. We made it real. The FRACTIONAL OFFICE category is picking up steam! In the past few days, we've added 3 more landlords to the platform - WTF Group, Hullmark and Lifetime Developments in Toronto alone. Welcome! What is also super-interesting is several other landlords are now adding fractional days-of-the-week products to try and catch demand from the fast-growing, fractional workspace category. Examples include Oxford Properties and their OxWorx initiative, MRP in DC and their HeyDay product, Tram Developments working with Cushman & Wakefield brokers to market fractional offerings and even iQ Offices and their new Sprint Spaces - now available though Flexday. 🌱 We believe these are the 'green shoots' of a fractional office future. ♻ Join us in creating a more sustainable, utilization-based office world.

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🚀 Just had an incredible experience meeting Keily Blair, CEO of OnlyFans in Toronto! Here's a mind-blowing stat: OnlyFans has paid out $15 billion to creators since 2016. Yes, billion with a B. 💸 The company takes 1/5th of the payments generated. With over 3 million content creators on the platform, it was fascinating to discuss the future direction of the business - which really has a ripple effect... OnlyFans has already shifted culture and how we think about creators. But their next big wave goes beyond content and culture—it’s about challenging traditional banking norms. With its massive financial footprint, OnlyFans is pretty well poised to reshape the financial landscape for lawful, profitable businesses often marginalized due to stigma. (👋 Shoutout to Sextech School founders, Women of SexTech, and other businesses that struggle to transact or even open business bank accounts.) Keily’s background as a partner at a law firm specializing in cyber, privacy, and security makes her the fit to take on the big banks. I love learning about how people found their ways into these sorts of spaces - for her, OF was a former client (and a fav client). I learned so much in our meeting. One last nugget that stood out: OFTV (their safe-for-work streamer) just licensed their first reality show to Netflix! At this point, the mainstream influence of OF, whether it's in entertainment or financial sector, is undeniably having a hand in what our future looks like.

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$150,000 in SDE. Would you even look twice at such a business? Scott Walton and his partner did, and they bought it. And another at around the same time that was doing $250k in SDE. (All figures Canadian.) So the combined SDE of both acquisitions is below the threshold that many searchers would consider. And yet... Scott doubled the businesses in 2023 and is gunning to double them again this year, which would mean $10m in revenue and well over $1m of profit going into 2025. And much more of that profit will go directly to Scott as owner versus servicing debt had they bought a $1m SDE business right out of the gate. One of the benefits of buying small is that you pay far less for the initial acquisition... meaning far less debt service... meaning if you can grow into the desired $1m of profit and beyond, you keep a lot more of that profit a lot sooner. Today's interview with Scott is how you might do just that. Some topics today: * Hiring a president so you can step out of the business (Scott was very much in the business at first; today his time is mostly devoted to strategic projects.) * Improving culture & introducing KPIs at a blue collar business * How they solved hiring by creating a full pipeline of blue collar talent * How they financed these deals without the SBA (they're in Canada) * How Scott gets very personal with sellers to arrive at a successful negotiation * Migrating from tech to the trades A dense and fascinating episode today. Here's Scott Walton, co-owner of Matrix Mechanical. Please enjoy. ( 👉 link to interview in comments below)

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DTC is a graveyard. Shopify has ~4M active merchants of which only ~100-200k are making any meaningful revenue. This is because majority of the new brands and stores being set-up are dead on arrival. At Monk, I've interacted with over 200 brand owners and operators over the last couple of years and also seen merchants using the app grow/stay steady/decline month and month and there's a clear pattern. It boils down to 2 things: 1. Category/niche Some categories are objectively worse than orders to build a DTC business in due to competition, limited TAM or poor margin structure. Choosing the right category has a massive impact on your odds of success 2. Product differentiation Most brands that fail have an undifferentiated product in a competitive niche with no clear advantages. There needs to be a very strong reason to buy from your website specifically - this is your differentiation, something that the buyer cannot get in marketplaces like Amazon or on other brands. Spending a large about of time trying to answer the 'why' of your product will set you apart from the hoards of brands that don't scale.

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This is John Fish:  He has ~1M on YouTube & a massive book club.  He skipped traditional VC and took investment in himself. --- Meet John Fish At 10, he was already coding his first app. By 16, he was working as an engineering intern at Shopify. For college he went to Harvard. But he wants to try to become the #1 creator on BookTube. Here's why that's an interesting decision: --- John has a serious love for reading. One that he's managed to parlay into a large (and growing) online business empire. It all started with his YouTube channel, which has almost attracted enough book lovers to earn him that coveted gold play button. (~1M subscribers) --- From there, he branched out into physical products by launching a notebook that is part journal, part daily planner. This helped him form a stronger connection with his audience and served as his first source of repeat revenue. --- Now, he's working on a SaaS app called Bookshelved. It helps users... • Discover new titles  • Track their progress  • Save and categorize their best insights  • Connect with other avid readers It also has a paid book club, which is his first source of subscription revenue. --- All that hard work eventually caught the attention of Slow Ventures. They've been writing checks from $500,000 up to $2 million for 5% of the entire financial output of that individual creator over the next 30 years. They recently wrote a check to John to help accelerate growth across his entire enterprise. --- Here are 5 reasons why... 1. A Sizable (and Growing) Distribution Channel John has grown his YouTube channel to almost 1M subscribers and uses this for awareness and distribution. 2. Defensible Differentiation John doesn’t just review books, he dives deep into their themes using an analytical, yet approachable style that appeals to a wide audience. 3. Business Acumen John uses his tech background to run data analysis that helps him understand his audience better than anyone else. This helps him optimize his content strategy and diversify his revenue sources by layering on in-demand physical products and software tools. 4. An Emerging Market 34% of Gen Z readers are finding their next title on YouTube. John has a strong foothold in an expanding market whose purchasing power is growing. 5. A Clear Path Forward Most importantly, John has a compelling plan for the money. He'll add features to Bookshelved and scale his content which benefits the entire enterprise. --- His story is a powerful example of how creators can leverage their creative talent to build successful businesses and this is exactly what we are building towards with my company Crowdsurf. With Crowdsurf, creators can raise up to $5 million from accredited and unaccredited investors in exchange for a small percentage of their future revenue and IP. And anyone can invest for just $50. If you're interested check out the website in my bio and follow Preston Troutt for more creator and startup highlights.

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Appreciation post for Shopify, especially the App Store team - It’s been there for more than a decade now. I haven't seen anyone appreciating the option for merchants to leave reviews for the apps they’re using on Shopify. Those reviews are a game-changer for Shopify SaaS founders like me. Running a SaaS company isn’t easy, and having long days is the new normal no matter what stage you're in. Whenever I receive a Slack alert that there is a new Shopify review for Vajro, it brings me immense happiness. It doesn’t matter whether it’s positive or negative. Someone took their time to write about us and share their feedback publicly is a different feeling altogether. It gives an opportunity to feel & express genuine gratitude towards the merchant. All the other benefits - organic ranking, seo, social proof - are all secondary. There are thousands of app developers in the ecosystem, and I’m pretty sure every single one has felt this. The mental calmness these genuine reviews provide is underrated, and nobody talks about it. p.s. Yes, we’ve set up an alert in our Slack for whenever someone leaves a review. Our whole team celebrates every single review together ❤️ You should do that if you haven't done it yet.

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Canada might be 1/10th the size of the US population, but Canadians still deploy capital into startups, but at 1/25th the rate of the US. If you're a Canadian founder you should meet some notable Toronto venture capitalists, ready to back your journey! 1. Relay Ventures-ventures Focus: Pre-Seed and Seed Stage Ventures Sector: Urbantech, Proptech, Fintech, Sportstech Top Portcos: Boomerang, Bird, Ecobee 2. Real Ventures Focus: Early-Stage Ventures Sector: Tech Enabled Businesses Top Portcos: Mejuri, Integrate AI, Unbounce 3. Radical Ventures Focus: Early Stage Ventures Sector: Artificial Intelligence, Disruptive tech Top Portcos: BirchAI, RoadBotics, Nabla Bio 4. Golden Ventures Focus: Seed Ventures Sector: Agnostic Top Portcos: ApplyBoard, Yesware, tacked 5. Alate Partners Sector: Real Estate, PropTech Top Portcos: Bird, Altrio, PadSplit 6. iGan Partners Focus: Seed Ventures Sector: Digital Health and MedTech Top Portcos: Meta, Akira, Think Research 7. Whitecap Venture Partners Focus: Seed and Series A Ventures Sector: B2B software and Med Tech Top Portcos: GoBolt, Real Matters, Clearwater 8. Ripple Ventures Sector: B2B Software Top Portcos: Wisely, Artemis, Plannuh 9. Loyal VC Sector: Tech Enabled Businesses Top Portcos: MyTM, ZestIOT, Avant Meats, BetaStore 10. Portage Focus: Seed to Series C Ventures Sector: Fintech Top Portcos: KOHO Financial, Albert, League, Clark Ready to connect with the perfect investor for your startup? Drop “LIST” in the comments, and I’ll tailor a personalized investor lineup just for you. Who’s your favorite VC firm in Toronto? Give them a shoutout in the comments! At Thunder.vc, we specialize in matching your fintech startup with venture capital firms that align with your sector, growth stage, and goals. Let’s find the right partner to fuel your growth!

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For the longest time, we thought AI would completely replace human CS. It's becoming increasingly clear that we were wrong. The past few months have seen huge corporations held liable for rogue outputs by the models they used for support. ➝ Air Canada's chatbot promised a customer an unintended hefty discount  ➝ A GM dealer chatbot was talked into selling a Tahoe for $1 As if the errors aren't enough, actual human support teams aren't huge fans of it either. Everyone wants to use the "cool new thing", but nobody wants to be replaced by it. The errors and concerns all converged into a new way of thinking about AI and support: When the stakes are high, copilots might make sense instead of human replacements. The new thinking is that AI-powered tools will be there to assist humans with support, but not replace them altogether. Think of it as having perpetual access to your smartest co-worker (the bot would be trained on your internal knowledge base). We may still be a bit away, but the idea is fascinating. I'm fascinated by the idea, and I'm not alone. Intercom took the first step by launching their own AI copilot. Down the line, the full replacement may happen. But for now, it looks like copilots could be the solution. All the benefits of an AI model, without the rogue outputs and with a human-in-the-loop. I really am curious—what do you think of this? Can you see your brand hopping on board?

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This plays right into Shopify's B2B expansion, doesn't it? BigCommerce has ~40k merchants, with the lion's share being B2B Shopify grew 150% on B2B last year and is a key focus area for them for the next 2 financial years This can play right into Shopify's hands where either - The acquirer makes a mess of it forcing BigCommerce merchants to find alternate platforms or - Shopify themselves acquires these merchants and shuts down BigCommerce entirely Follow along to see how this unfolds.

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