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👉 5 Things I've Learned Over 2 Decards of Entrepreneurship
Published 22 days ago • 7 min read
Hey Reader,
Before we jump into this week's topic, could you do me a huge favor? A couple weeks ago, I mentioned the new podcast I am co-hosting. I would be so appreciative if you could leave a 5-star rating on Spotify and/or Apple Podcasts. It helps us get more visibility for the podcast and therefore help more entrepreneurs like you. Thank you in advance!
Over the past 20 or so years I’ve started quite a few businesses. To be completely honest, I’m not sure what the total number is, but it’s probably more than I should have.
I’ve had some success, and I’ve had some failures, but I’ve learned so much that I wouldn’t take a single crazy idea back.
Here are just 5 of the things I’ve learned from starting my own businesses.
1. It’s Better to be A Business Owner Than to be Self-Employed
What's the difference?
An electrician who works for himself and is required to be at every job in order for that job to be completed is Self-Employed. An electrician who has a team of electricians who are competent enough to complete jobs correctly and efficiently on their own is a Business Owner.
When I founded FTF Records in 2005, our main source of revenue was local events we promoted. The issue was, I didn’t have anyone to run those events for me, so I needed to be at every one.
Self-Employed.
As these events got bigger and ran smoother, I brought on a partner who worked with me for a bit and learned how to book, promote, and run events on his own. He got very good at it. I’ll never forget being in San Diego for a business conference and receiving a call letting me know that the two events that weekend had went well and we had made a profit.
Business Owner.
I had built that business to a point where it could make money without me being there. It wasn't that I was never needed. I just wasn't always needed. I had created freedom for myself.
2. It Takes Longer Than You Think
Patience. Patience. Patience.
(Yes, that's all I meant to write for this one.)
3. Most People Won’t Help
Even though everyone you know will offer to help, remember that it is your dream. You’re the one who has the drive and you’re the one who will ultimately decide your company’s fate.
Most people claim to want to be business owners, but very few have the drive and willingness to sacrifice what is necessary.
I’m not telling you to turn down help. When a friend offers to help, schedule a professional sit down with them and discuss what they can help with, why they want to help, and what they are willing to do. Take your time in making a decision and be sure not to put too much on them at first. Test their abilities and dedication with a few small tasks.
Most importantly, don’t be disappointed or take it personally when they don’t pan out. Most people don’t know what it takes to work in a small business.
4. Everyone Wants to be the Boss. Nobody Wants to be the Owner.
When I was younger and first began venturing into entrepreneurship, everyone I knew would say they wanted to do the same thing; be their own boss. Who wouldn’t want to be?
The problem is; most people don’t know what that means.
It's easy to think of all the positives: making your own schedule, not being told what to do, etc.
Unfortunately, most people don’t step back and realize the difficulties of keeping your own schedule and staying on task without being told what to do.
“It would be so cool to work from home. Just sit around in my boxers and watch TV while I work.”
Yea, I’ve heard that a lot. Here’s the problem:
When you’re in your boxers, you work like you’re in your boxers. I’ve found time and time again that when I dress as if I am in an office, I work like I’m in an office. Yes, I am saying that when I work from home, I often dress professionally.
TV is entertaining. Things that are entertaining are distracting. When you’re distracted you don’t work.
5. Patience is Key
Yes. I meant to repeat this one. And yes again, this is all I meant to write. This is going to take longer than you think, and longer than you want it to. Stay focused. Stay consistent. Stay flexible. Stay patient.
I hope this helps
~ Jeff
*Keep scrolling for I’m listening to, links to check out, and a content creation idea!
✅ 19 Social Media Best Practices for Faster Growth
Whether you’re a startup, a creator, a big brand, or a nonprofit, social media best practices like the ones shared in this post can keep you on top of the social media game.
Remember, social media best practices can change fast. So it’s a wise idea to peep the to-do lists throughout the post even if you think your social strategy is already running like a well-oiled machine.
When it comes to social media platforms, Facebook is as crowded as they come. The social network currently has a staggering 3 billion active users — so almost a third of the world population has a Facebook account they use regularly.
Crowded as it may be, it’s still a powerful social media marketing platform for businesses and creators — if you have the right social media strategy in place.
Part of that content strategy involves figuring out the best time to post on Facebook for maximum engagement.
The team at Buffer analyzed more than 1 million Facebook posts sent through Buffer to pinpoint the best time, day, and post format for maximum engagement.
Success requires high-quality original content, deep understanding of user intent, and the ability to adapt to rapid changes in search behaviors and technology.
Google's AI overviews and core updates shook up search rankings. Watching rankings drop without explanation was frustrating, leaving many wondering if SEO even had a future.
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If you had to start your business, brand, or side hustle from scratch today, what would you do differently?
This type of content is powerful because it helps newer folks in your world avoid common mistakes, and gives them a clear roadmap based on real experience.
Here’s how to structure it:
Step 1: What’s the first thing you’d do differently? (Example: "I wouldn’t waste time on a fancy website—I’d focus on building an audience first.")
Step 2: What would you skip entirely? (Example: "I spent months perfecting my logo… turns out, no one cared and I changed it a year later anyway.")
Step 3: What’s one thing you’d double down on? (Example: "I’d start my email list immediately instead of waiting.")
You can create this as:
A social media post listing 3-5 things you’d do differently
A newsletter with a deeper breakdown of each step
Happy creating!
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Helping educators create and grow brands to promote a product or idea they want to share with others to better education. Tips, tricks, and resources for educators creating content and/or launching side hustles to share their passions.
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