Matt Mayers

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

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.

15

2 Comments

"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

8

1 Comment

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

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

21

1 Comment

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)!

349

28 Comments

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

36

6 Comments

Shopify’s Winter ’25 Edition is here, and they’re calling it "The Boring Edition"—but it’s far from boring, just check out their website—I absolutely loved their vintage TV theme! This update focuses on small but impactful improvements to make the platform even better for merchants and developers. with 150+ updates, here are a few highlights: 1. Customer Account Extensions: Add loyalty programs, wishlists, and more—no coding required. design choices now carry over from checkout to login, and header menus are fully customizable. 2. Shop Campaigns: Available on all plans in the US & Canada, these risk-free ad campaigns now work on Google Shopping too. set your budget, pay only for conversions, and let Shopify do the heavy lifting. 3. Shopify POS Upgrades: Offline payments, customer metafields, and distance-based customer segments make selling in-store or on the go even easier. 4. Shopify Bundles: Improvements make bundles clearer in checkout and emails, with POS integration and detailed performance analytics. 5. Faster carts & checkouts: Shopify’s cart now loads 50% faster, and checkout buttons are up to 58% quicker, improving conversion rates across the board. 6. Sidekick for all merchants: Shopify’s AI assistant is here to provide personalized recommendations and help you navigate the platform like a pro. These aren’t flashy new features but meaningful improvements to tools we already use every day. Check out all the updates here: https://lnkd.in/dXxxfaDz #shopify #shopifyplus #ecommerce #shopifyupdates

1

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!

44

5 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

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

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

3

Losing Product Market Fit – The Canada Problem* ➡ Over the past 6 months I’ve done a lot of talking, and writing, about the importance for scaleups not to Losing Product Market Fit. Losing PMF happens when a scale up starts to get traction, perhaps £2m to £10m in revenue, but external forces start to pull the company away from its mission and destroying PMF. The best anecdote I’ve found over the past few months is from Marc Randolph, Netflix Founder, who calls this the “Canada Problem”. As Netflix were growing, they had the chance to move into Canada, something that would grow revenues 10%. They decided not to, this new geography would have become a distraction. There would be new languages, regulations and operational requirements, all of this would soak up aload of time and focus. So, Netflix leadership decided their time would be better spent on their core proposition - subscription DVDs in the US. Any time spent in Canada could be spent on their core proposition. Every time something came along that wasn’t subscription DVDs, such as selling DVDs online or physical rental machines, they focused on their core offering – ultimately defining what it meant to be a B2C subscription business. Randolph describes this throughout his book as "The Canada Problem". Earlier in the year I was privileged to speak at SaaStr where I talked about this alongside some other losing PMF topics. Jason M. Lemkin is someone I follow closely, so to speak at his conference was a real honour. This is a link to the conference…. I come in at 3 hours, 21 minutes and 25 seconds…. Apologies for the first 10 seconds where I get blinded by the lights. https://lnkd.in/eaetVsW8 So, if you’re a founder, and you’re ever been tempted away from your mission, remember Netflix Canada problem, and you just might just hold on to Product Market Fit! My three-part blog series on losing PMF is in the comments below. #losingPMF, #founders, #venturecapital *Canada is not a problem – just a metaphor for the dangers of losing PMF.

43

6 Comments

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.

33

3 Comments

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.

109

16 Comments

$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)

83

10 Comments

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.

46

24 Comments

Thanks for the call out Deedy Das! Appreciate the post! 🙏 I recently brought on a world class CEO Coach Matt Mochary. He also coaches Sam Altman, Brian Armstrong, Steve Huffman and many others. As I dissected this with him - he advised that VCs invest using the relationship method (investing in companies where there is a built up trusting friendly relationship) and the company profile ends up being secondary. While of course it is still important to have good metrics to close the deal - without the relationship VCs can and will find any excuse/reason/number NOT to invest. I know this to be true because every single round we have raised (we have raised $150M+) has been built on existing relationships. Our investors have been amazing and incredibly supportive - Bee Partners, Lightbank, Inovia Capital, Lion Capital, Acrew Capital, Titanium Ventures, Harley Finkelstein, Stephen Curry, Penny Jar Capital, Full In Partners, BDC, Hyphen Capital... However 2 things are different: 1 - While Henry Shi is now in SF and I spend a lot of time out there - I still live in Toronto and about half our company is here in Canada. Nothing compares to living in SF and naturally building relationships there. 2 - We did not start the company going up the 'standard' silicon valley path. Going through Y Combinator means you are in the inner circle to get picked up by Sequoia Capital, Andreessen Horowitz, Accel, Kleiner Perkins, Benchmark and so on... as there are strong relationships already built there. All this being said - it doesn't really matter 😀 While we may not be well known in the Silicon Valley echo chamber - we are helping millions of customers save, earn, build their credit score, and experience more of what life has to offer. We are growing fast, profitable, and will get to a great outcome! It just may take us a bit longer. :) 💪

66

6 Comments

Building a new category is tricky, and it's come to my attention that people don't know what FERMÀT is. So we asked...how would they describe it? Maximilien Langlois answer (Founder of HYPE10) was fascinating: “(FERMÀT) is a landing page solution that necessitates very little time to validate ideas and prove theories for an e-commerce brand.” Max isn't wrong. We build landing pages. But we're not a landing page solution; we're a full-funnel solution. And we help you do it quickly. With FERMÀT, you can spin up funnels at the same speed as ads. That’s the category we’re creating. I'm happy to see that Max is using the tool to experiment, innovate, and push boundaries. It's a testament to the versatility and power of our platform. So whether you're looking to validate theories, optimize marketing strategies, or boost conversions, FERMÀT is here to help you achieve your goals with efficiency. You can catch our chat with Max on our FERMÀT Friday channel, and his full answer in the video.

22

3 Comments