How to Win on Linkedin

One of the influencers I work with received a DM from Elon Musk three years ago that read “Linkedin is so cringe it makes my toenails curl” At the time, Elon was right.

Linkedin has been around since May 5th, 2003 and after 12 months they were up to 500,000 users. Today, the United States has the most active user base with over 250 million Linkedin profiles. What are all of these people doing there? Why do they care? How does this benefit them at all?

I have built a 12,500 person Linkedin following which results in about $200,000 in monthly inbound deal flow for my company. In some ways, my personal Linkedin is my company. Here are some lessons that I have learned along the way that could help you grow and eventually earn money from Linkedin.

Many folks are on Linkedin to find their next job, self promote, and market their own product. In the past few years, the platform has seemingly turned the corner and become a great place to publish both insight, and humor as well.

When I was a software sales rep, a VP of sales told me that he has made an entire career off of his 30,000 Linkedin followers. He had a formula of maxing out his connections on a weekly basis by filtering his network to automotive, then to first and second connections, then filtering to personas such as General Manager, and sending his 200 connection requests per week so that his account gained at least 200 followers weekly. Connections and followers are not outwardly displayed differently on your profile.

This is a fine strategy, but eventually you need to begin posting something if you actually want to grow. My thesis is that you have to post something either insightful or funny. If the post does not rise to that occasion, then ditch it.

Humor

Humor is a risk, especially if you are not funny, or too funny. The funny posts are great for audience growth. Even if a post does not get a lot of likes, you will score a lot of impressions because people are stopping on the post to digest it, and it will be served to a wider audience. Look at this post below with a meme I made comparing a Swiss Banker to a Chevrolet dealership General Manager, only 40 likes, but 10k+ impressions. Also, all of those impressions came from a senior audience made up from founders, general managers, owners etc.

Satire has found its footing on Linkedin with legends like Corporate Bro, Corporate Dudes, Johnny Hilbrant, Corporate Sween, Corporate Natalie and Sully Finlay all leading the pack. Check out the Corporate Dudes Meme Generator. I use this to source memes for my own account and clients. These dudes make humor much easier.

Insight

Insight is the most valuable thing to post on Linkedin, but you need to refrain from making it self congratulatory. This post below took a little bit of research about AI investment, and although it flopped from a likes standpoint, there must have been something appealing for the algorithm to serve it to 8500 people, mostly founder and CEO titles. Tagging other companies helps, using the …more button to tease an expanded thesis helps too.

Formatting

The biggest hack in formatting right now, is an image with text above it tagging multiple companies, people, and even your own company at the bottom in a recurring convention. I screenshotted a viral founder post I found on X, and then tagged the person on Linkedin and explained the nature of his viral post. It resulted in a lot of outreach from folks, including the founder himself.

Also, use the …more button to your advantage, if you create a hook, which is a creative controversial or humorous first line, perhaps place your second line of writing a few lines lower, so that the reader must click the …more button to read the post. This stokes engagement.

Polls

My friends make fun of how often I put a poll on Linkedin, but I consider it an engagement hack. If you put a question out there, and purposefully constrain the answers, you will get a ton of engagement including people gleefully telling you the answers that you forgot to put there.

My best poll recently demonstrated a touch of industry expertise while soliciting engagement from people within the industry I value most, automotive. 680 Votes, over 2,000 dealership general managers saw this post.

Sentimental Content

I went against my intuition and posted a video of my daughter recently on Linkedin. It crushed. I always swore off using my children in advertising, but this is hard to resist. Again, the right personas engaged, the content was too good to ignore. 1,500 dealership general managers were served this clip.

Growth Through Comments

To grow a valuable audience, you need to engage with large accounts and provide a valuable comment that attracts engagement from the followers of that larger account. Again, it needs to be funny or insightful or don’t post it.

Help People Get Jobs

Something that has helped me grow my account a lot is encouraging others on the job hunt, and helping my friends get their jobs filled on Linkedin. It has gotten to the point that when some folks are looking for a new employee, they reach out to me first. Help people fill jobs, help your network get jobs. This comes back to you 10x.

Take Risks

I almost didn’t post this one below. However, 2,100 dealership general managers saw this post, it got a lot of engagement, and was the most successful post I had made in 45 days.

Where is Linkedin Going?

Linkedin is coming into its own, and I could see it eventually becoming better for long form content. Right now major creators like Chris Koerner do not currently post their podcast episodes on the platform because Linkedin lacks the correct formatting to find episodic content.

So, we are in the early innings, most of the content is cringey, but that is what you need to start right away. Encourage your college aged kids to grow their account, post often and take some risks!

They could become the next Fernando Mendoza!

Suggested Follow

My favorite follow on Linkedin the the Netflix co-founder, Marc Randolph. Marc is a great writer, has unparalleled expertise, and seems to really care about imparting a motivational message to his followers. Linkedin just named him one of the top voices of 2026.

Mistakes to Avoid

Freddy Media would like to share our best practices with you.

Here are some products we find useful, and would encourage you implement in your company.