December 29, 2023

My Top 50 Posts of 2023

The best of startup founder advice in 202

What You'll Learn

It’s f’n hard to start something new.

And this year was a stark reminder of just that!

Nine months ago, I started posting content for startup founders on LinkedIn and Instagram, mainly to get a bunch of thoughts out of my own head.

When I was in the thick of it running Classy, I became frustrated by the lack of quality content for startup CEOs. For SaaS, there were some great blogs like Jason Lemkin’s and David Skok’s, but these weren’t focused on the role of a startup CEO–what to do, and what not to do. How to become a real leader and scale a team. 

What I really wanted was guidance from a successful CEO who had been through it already… but I couldn’t find that anywhere.

So I made a promise to myself that someday, if Classy was successful, I would share all of my own learnings as a startup founder & CEO. And maybe these learnings would be helpful to other founders/CEOs going through a similar thing.

That’s what 2023 was all about – the start of sharing this journey.

And honestly, I was blown away by the response. I went from posting stuff that only got a handful of likes to a community of 76K followers in only 9 months. And, probably, the most exciting development… launching my first Startup CEO Accelerator and Community

But the journey is just getting started. 

I’m extremely grateful for every single person who decides to click “follow,” read my blog or join our Startup CEO Community. And I don’t take these relationships lightly. You can rely on me to continue delivering throughout 2024 and beyond. 

For now, I thought it’d be fun to take a look back at my top posts of 2023 across LinkedIn and Instagram. Out of 200+, here are the top 50! 

See you on the other side (2024).

Much love,

Top 50 LinkedIn Posts of 2023

  1. How to Crush 1×1 Meetings
  2. Most Teams Secretly Don’t Trust Each Other
  3. The Real Reason You’re Losing Top Performers
  4. 12 Simple Habits to Become a High-Performing Manager
  5. The Only Three Meetings You’ll Ever Need
  6. 5 Lessons for New Managers
  7. My Top 3 Rejections with Raising from Investors
  8. My Top 7 Mistakes Raising $200M from Investors
  9. How to Create a Strategic Vision Like Elon Musk
Access my 1-4 method template to copy for your company.
  1. How to Create a Mission Statement That Doesn’t Suck
  2. 21-Year-Old College Grad
  3. How to Ask for a Raise
  4. How to Give Yourself a Personal MBA
  5. Don’t Become the Manager Everyone Hates
  6. Stop Giving Sh*tty Feedback
  7. How to Become a Top 1% Leader
  8. How to Adopt a Winner’s Mindset
  9. 10 Worst Pieces of Startup Founder Advice
  10. 6 Highly Effective Public Speaking Hacks
  11. Most Meetings Are a Total Waste of Time
  12. Top 7 Mistakes as CEO
  13. 10 Signs of Great Culture
  14. 7 Ways to Master Resilience
  15. How NOT to Take Things Personally as a Leader
  16. 6 Steps to Become a Top 1% Manager
  17. These 5 Rules Transformed My Schedule… and Life
  18. How to Beat Imposter Syndrome
  19. They tell you it’s product or market that kills a startup, but after investing in 20+ startups…
  20. 7 Leadership Blindspots
  21. 3 Things Great Managers Think About All Day
  22. Using the PDP Test – Test Your Boss’s Leadership
Take the PDP Test for yourself!
  1. How to Display More Confidence Than You Actually Have
  2. 6 Steps to Become a Great Manager AND a Great Leader
  3. How to Lead Like a Minimalist
  4. How to Crush Your All-Hands Meeting
  5. Resumes are Overrated
  6. Stop Focusing on Culture
  7. 7 Imaginary Rules I See Holding Most Leaders Back
  8. If You Struggle with Public Speaking, Read This
  9. I Lost an Amazing A-Player Once…
  10. 7 Critical Lessons for First-Time Founders
  11. Top 7 Interview Questions To Hire A-Players
  12. 5 Non-Obvious Traits of World-Class Leaders
  13. Which one are you? Founder & CEO or CEO & Founder
  14. How to Resolve Conflict as a New Manager
  15. The Ideal Compensation Package for any Startup Founder
  16. 7 Business Things You Won’t Give a F*ck About in 5 Years
  17. What a Top CEO Actually Does
  18. 8 Tips to Strengthen Your Work Relationships
  19. The Only 3 Metrics You Need to Track

Top Instagram Reels of 2023

In case you like to absorb your content in shorter videos, here are my top 15 Reels from 2023. 

I’m having a lot of fun figuring out the video space and have big plans for 2024. Don’t forget to follow

  1. How Anyone Can Innovate
  2. How to Get the Most Out of Investor Meetings
  3. Using Rejecting as Fuel
  4. How to Get Through Imposter Syndrome
  5. How to Build Trust Across Your Team
  6. The Only 3 Meetings You’ll Ever Need
  7. Never Freeze up During Public Speaking
  8. How I Make Decisions
  9. Be Careful Who You Raise From
  10. Work-Life Balance as a Startup Founder
  11. Stress Hacks I Wish I Knew at 20
  12. The #1 Reason Startups Fail
  13. How to Deal with Bad News
  14. 80-20 for Personal Growth
  15. Don’t Be the Manager That Everyone Hates

Three ways I can help you in 2024:

Are you a founder, executive, or manager? I’d love to support your professional growth. 

  1. Connect on LinkedIn and Instagram – where I post practical tips about leadership and startups every day.
  1. Subscribe to my free newsletter – where I go deep on a variety of management and operations topics that will make you a better leader & operator. 
  2. Join Highland – my executive coaching program for founders, where we help you become a top-tier CEO who can scale into the tens of millions & beyond.

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