VEN

This is the hardest time of the year for a lot of professionals There is a brutal clash of professional, social, and seasonal elements. 💼 💼 💼 Professional --> Business Obligations are at their Highest The vast majority of companies have a fiscal year that aligns with the calendar year. This means that there is a mad push to get as much revenue in the door by December 31. And even if your company doesn't run on the calendar year, it's alsmot certainly true that most of your customers do. So there isn't much of a let up for anyone. 👨👩👦👦👨👩👦👦👨👩👦👦 Social --> Social Obligations are at their Highest Holidays and school breaks are heavily concentrated into this part of they year. This doesn't just mean "there are an extra few days off" but there is a broad social expectation that everyone will take estra time off to spend with friends and family. Add to this the time spent preparing for this social time: buying gifts, groceries, cleaning, etc. I think quality time away from work is critically important, but the reality is that days off compress business output, and (In North America, at least) this compression is the worst in November and December. ❄️ 🌨️ ❄️ 🌨️ Seasonal --> It's Cold and Dark If you are North of the equator, then it's really dark this type of year. There is plenty of research showing that this has major impact on our moods and energy levels. It's also colder for everyone, and oppressively cold for a lot of us. This reduces outdoor time and limits healthy activities. These clashing of these three things is no joke. I personally feel it every year. It's long. It's hard. It's utterly exhausting. Hopefully I can help some folks put their finger on this and help them buckle down for the grind.

While Halloween is fun for the children, let's not forget who the real monsters are.

I had two deeply contrasting experiences over the weekend relating to people and their attitudes toward work. 1. I was at a couple of social gatherings (I know). 2. I watched The Bicycle Thief. While socializing, I was struck by how people spoke about their work. There seemed to be three things folks bragged about the most: 👉 How little they do. 👉How much time they get to spend away from it. 👉How easy it is. I kept wondering: Is this what we are supposed to be aiming for? Optimizing for leisure and striving to do as little as possible? Then I watched The Bicycle Thief. Along with being considered one of the greatest films of all time, it does an amazing job of unpacking the desperation of a man in post-war Italy as he struggles to secure work and support his young family. That desperation must have resonated with audiences globally. Many in war-torn countries could barely make ends meet. Even in North America, while things were better post-war, a lot of the population still remembered the Great Depression and the fallout of those times. Here’s where I’m going with this: Most of our grandparents had no security. Many didn’t know where their next meal or paycheck was coming from. It makes sense that they sought security above anything else, and it makes sense that they passed these values down to their children. After all, the hungry ’30s weren’t so long ago. But… many people I talk to today don’t have the kinds of threats that job security solved 100 years ago. In fact, they typically face far fewer immediate threats at all. So my question is: What are we celebrating when we brag about how little we do or how much time we get off? 👉 Is it virtuous to only work 35 hours per week? 👉 Is it desirable to produce far less value than you are paid for? And in all honesty, I don’t care how people want to organize their priorities or lives. I don’t care if someone chooses not to work hard. But I do wonder: Should we really be celebrating the deliberate absence of effort or productivity? What do you think?

I know your type. You start a new job, you kill it for a bit, then you plateau. And that plateau feels endless. You know you don’t want to be there anymore, but you think there is something wrong with you. So you hack it out awhile. But things get worse. 👉You built your best stuff in a few months 👉Work just feels like meetings and arguments 👉You spend most of your time on maintenance and reporting You start looking around and you see a company that excited you. You go for it, get it, then the cycle starts all over again. If this sounds familiar, here’s the truth: it’s not them, it’s you. But that’s a good thing. Employers aren’t for you. You are a builder. And it is a really exciting time for builders. There are two paths to pull you out of this cycle. 1. Find cofounders and go build a company 2. Go fractional and start consulting I did the latter and it’s been the most rewarding step of my journey so far. Go for it.

It’s not just about the tools -- it’s about what those tools reveal. Tech stacks reflect more than just software choices—they tell you how a company thinks and operates. Is your company... 👉 Distracted by shiny objects? 👉 Never following through? 👉 Rigid and resistant to change? Or... 👉 Nimble and adaptive? 👉 Strategic and deliberate? 👉 Sturdy and confident? Can you see it in your tech stack?

I’m incredibly excited to announce I’m joining the board of advisors at Quill Design Studio! I believe that brand is going to be the number one differentiator that sets great companies apart in the coming years. Quill stood out to me because they’ve nailed what so many miss. In a world where AI makes bad design easier than ever, Quill is bringing intentional, thoughtful design back to the forefront. Why am I so bullish on Quill? First, they didn’t start with a website, or even a name—they started with customers. Founder Sophie Itenson built the service, got real users onboard, and validated the business before anything else. That kind of traction speaks volumes to the market’s demand and trust in what Quill offers. Second, they’ve created a breakthrough SaaS model for graphic design. And in a time when how your brand looks determines how your brand performs, companies that prioritize top-tier design will hold a major competitive edge. I couldn’t be more excited to be a part of this journey to help Sophie + Jake E. Windsor and the rest of the team build a design engine that will allow businesses to take control of their brand image and thrive in the long term. This is going to be a big one—let’s go! 🚀

Job hoppers: you may be looking in the wrong place. Maybe traditional workplaces can't give you what you need. It's very possible you're a natural entrepreneur.

Strong revops leaders are well-positioned for exec roles, but few get there. Why? Backbone. My observation is that we have done a poor job of advocating for ourselves as critical to an organization's success. Think about it. A great revops person will have a depth and breadth of knowledge that is extremely useful from both tactical and strategic points of view. ✔️ Deep knowledge of all GTM functions, people, operations ✔️ Deep knowledge of all company strategy ✔️ Deep knowledge of systems ✔️ Deep knowledge of customer profiles and TAM ✔️ Deep knowledge of data Someone who can speak to all of these things with clarity will be useful in any room at an organization. So why aren't we seeing more revops folks in executive level roles? It could be lack of visibility --> Some revops folks prefer to work in the background It could be org structure --> Some revops roles are relegated to serve single GTM stakeholders It could be perception --> Some companies see this role as a minor player in a larger GTM effort I'm sure there are many more reasons. But regardless, anyone who has command over all of the areas listed above has everything they need to contribute at the most senior level of an organization. to my revops people: fight your way to the table. It's possible. I know because I've done it.

CRM certifications are the worst way to grow in revops. I actually find there is a negative correlation between how many certifications someone has and how fireable they are. Good revops people need to understand business problems first. If you can do this, and you can communicate around this effectively, then you are going to be valuable to any business. Being able to configure a CRM is the easy part. It just takes a little practice and there is a ton of documentation and community support to help.

I got quite a bit of blowback on having the audacity to suggest that work-life balance is a trap and that working extremely hard is the best way to get ahead. But the nature of the criticism was funny... I was told by a few people that I'm spouting BS because employers will not, in fact, reward people who work extra hard. These people are proving my point!! My core point is that relying on employers to make you successful is a TERRIBLE idea. Employers give you salaries, perks, titles, and many other things in exchange for your freedom. They essentially own 40% of your time. For me, that's WAY too big of a compromise. When I suggest that people should show up early, work late, and do the hard things, I'm talking about building up the strength, confidence and skills to take control of your time AWAY from employers. This worked for me, but its the same story with almost every other founder I've spoken to. 👉 Do the work 👉 Push yourself 👉 Learn how to do hard things 👉 Get involved with other ambitious people Take control.