Highland

Most people think great leadership is about charisma. It's not. After working with hundreds of founders and leading Classy from 0 to $100M+, I've noticed something interesting... The best leaders are actually obsessed with 3 very unsexy things. You won't see these on inspirational posters. You won't hear about them at leadership conferences. But they're the difference between good and great. Here are the 3 obsessions all great leaders share 👇 _____ 📌 PS. Join our free newsletter & community of 100,000+ https://lnkd.in/gfMMvV6c 📌📌 PSS. If you're a founder or CEO, you should check out Highland , my community + accelerator to help scale you & your teams. Apply here: https://lnkd.in/gWqNamTw

My biggest mistake as CEO almost killed my company. Don’t fall for the same trap. During our Series C at Classy, we had multiple interested investors. But only one offered a valuation that was 20% higher than the others. Like most founders, we went with the highest valuation. Big mistake. The next 3 years were hell: - He tried to push the founding team out - The culture tanked - Performance dropped - Everyone was miserable It was like having a cancer we couldn't get rid of. Eventually, I rallied our existing investors to buy him out. The company rebounded almost immediately and later hit $1B. But I learned a brutal lesson: The right investor at a lower valuation is infinitely better than the wrong investor at a higher one. When raising capital, don’t judge investors by the size of the checks they can write. Instead, evaluate them based on: - Strong culture fit - Aligned vision for the future - Track record of supporting founders Whatever you do, don’t get caught up in the valuation game. The wrong investor is never worth those few extra zeros. ____ 📌 PS. Join our free newsletter & community of 100,000+ https://lnkd.in/gRxdayew 📌📌 PSS. If you're a founder or CEO, you should check out Highland , my community + accelerator to help scale you & your teams. Apply here: https://lnkd.in/gWqNamTw

This is what founder support actually looks like. No BS motivational quotes. No 'crush it' culture. Just real founders helping other founders solve real problems. Every other week we host Office Hours - a private session where Highland members workshop their challenges, pressure test their operating frameworks, and get unfiltered feedback from peers, and Scot Chisholm, who've been there. Because here's the truth: Building a company is hard as hell. And conventional wisdom usually gets it wrong. Want to join us? We're accepting applications for our next cohort of founders. Link in comments to apply 👇

How to crush your 1x1 (one-on-one) meetings… A 1x1 meeting is one of the most important tools for company building. It's a simple meeting between manager and direct report - sounds boring right? But in a short amount of time, you can align & influence behavior for weeks. But most people get these meetings wrong. Give me 2 minutes and I'll show you how to get the most out of your 1x1's: ________ 1/ Be consistent & be present The worst thing you can do is make your 1x1's irregular, or not give 100% attention. For frequency & duration, I've found that 60 minutes every other week is perfect. Keep things informal & mix up the setting. Try and get out of an office setting. You can move a 1x1, but don't cancel. Canceling says, "my other priorities are more important than you". ——— 2/ Let your direct report lead Put your coaching hat on and spend 80% of the meeting listening. But give the person a meeting structure to help guide. Here's what I use: → 15 min: an update on their goals → 30 min: they set this agenda → 15 min: manager brings anything forward For the last 15 minutes I usually pick two items, one in each bucket: Praise something you observed and give feedback on something that needs coaching. ________ 3/ Give & take feedback 1x1s are the perfect place for honest and open dialogue between the two of you. You also want to get honest feedback on how you're doing as a manager. Ask questions like: - How can I help you hit your goals? - Are you waiting on me for anything? - Anything you'd like to better understand about the business? ________ 👉 Bonus tips: • Use a notepad to jot down topics throughout the week for your next 1x1. Managers should create a note for each direct report. • Break the ice by starting 1x1s with a non-business question: how was your weekend? How are things in your world? Relationships first, and business second. • Once a quarter, extend the 1x1 to 90 minutes. Focus more on career & personal development. 📌 PS. Join our free newsletter & community of 100,000+ https://lnkd.in/gRxdayew 📌📌 PSS. If you're a founder or CEO, you should check out Highland , my community + accelerator to help scale you & your teams. Apply here: https://lnkd.in/gWqNamTw

I became a 10x better manager & leader... When I started focusing on high-leverage activities above all else. And I mean really focusing on them. Not just checking them off a list and moving on. These are things that are relatively simple to do, but have a massive impact. Sometimes for years! But they feel like a pain in the ass to most people. Which is awesome for you. Because while everyone else glosses over the things on this list... You'll be: - Hitting your goals - Keeping people motivated - Freeing up your time - Scaling your company What would you add? ___ 📌 PS. Sick of newsletters yet? Here's one you'll actually read: https://lnkd.in/gRxdayew

In my last 15 years in business, I’ve built teams of 300+. And studied what the best have in common. Then I came across a book called "Great Teams" That analyzed hundreds of sports teams... And it was so similar, I had to share it with you. Here are the 6 things that all great teams have in common 👇 Leaders, pay attention! ______ 📌 PS. Like this post? Try the only leadership newsletter you'll ever need:https://lnkd.in/gRxdayew

"I implemented that tactic in our sales team the next day." That was the feedback I received from one of our Highland founders after our recent fireside session with Mark Roberge and Scot Chisholm. The tactic? Mark's Red-Yellow-Green method for defining your Ideal Customer Profile (ICP) and strategically allocating your sales and marketing efforts. Here’s the breakdown: -Green: Home-run fit. These are your ideal customers. Focus all your outbound efforts here—cold calls, marketing campaigns, everything. -Yellow: Potential fit. Don’t proactively target these, but if they come inbound, evaluate carefully. -Red: Poor fit. Say no, even if they reach out. Yes, even when it’s tempting. Why is this so powerful? -Eliminates the guesswork/subjectivity when evaluating sales prospects. -Creates clarity and efficiency across teams with a shared framework. -Maximizes the ROI of your marketing spend by focusing on the best-fit customers. Simple but effective. Mark’s blog breaks it down in even more detail: https://lnkd.in/eB7QxG_x

I made these three mistakes myself. It cost us millions in wasted time and money. But this was before I brought on the incredible Hiten Shah as one of my advisors at Classy… And he helped me clean up my mess in three key areas. Ten years later I had the great privilege of interviewing him live in front of the Highland community… And as my kids would say, Hiten cooked To this day I think Hiten’s one of the most incredible, and underrated, startup thinkers out there. If you started a company - or dream of starting one someday - this week’s article is for you. I highlighted three core areas where most founders waste millions… With Hiten’s advice on how to navigate each + my own personal take. This is the first of many experts we’re going to highlight in the newsletter. Hope you enjoy it as much as did. Check it out here 👇

When founders break bread together... 🚀 Last night's Highland NYC dinner brought together an incredible mix of leaders across tech, CPG, and everything in between. From robotically handwritten cards to revolutionary cat litter (yes, really!) - the range of innovation at one table was mind-blowing. Huge thanks to our Highland members Alex Fram-Schwartz, Holman Gao, Yogesh Shetty, and Fletcher Struye, our community manager, for hosting some amazing founders. This is what Highland is all about - bringing ambitious founders together to share war stories, learn from each other, and build lasting relationships. Who's joining us for the next one? 👇

Most speaking advice makes you more nervous, not less. Here are 6 public speaking tips that actually work: ___ 📌 PS. Join our free newsletter & community of 100,000+ https://lnkd.in/gRxdayew 📌📌PPS. If you're a founder or CEO, you should check out Highland, my community + accelerator to help scale you & your teams. Apply here: https://lnkd.in/gWqNamTw