Ep. 19: 10 Lessons I’ve Learned as an Entrepreneur

Today is our first solo episode of the season and we’re diving into 10 lessons that I have learned in my past two years of full time entrepreneurship. 

So grab a cup of coffee and let’s dive in! 

In this episode, we discuss:

  • [6:20] Lesson #1: You don’t need to have it all figured out
  • [8:26] Lesson #2: You cannot do it alone
  • [11:42] Lesson #3: Don’t invest just because everyone says you should
  • [14:03] Lesson #4: Button up your contracts with a lawyer
  • [16:52] Lesson #5: Systems will be your best friend 
  • [20:59] Lesson #6: Your role should change
  • [25:00] Lesson #7: Get your team invested in your vision for your brand
  • [27:55] Lesson #8: Entrepreneurship is a roller coaster 
  • [30:49] Lesson #9: Have a greater mission than money 
  • [33:11] Lesson #10: Celebrate your small wins 

Lesson #1: You don’t need to have it all figured out

This lesson was a really freeing one because I felt like I needed to have everything all figured out the second I left my corporate job. When it comes to entrepreneurship, you start as the CEO so while there aren’t always new positions to reach towards, there are always bigger goals to be hitting. 

What’s fun about entrepreneurship is that you are the one who gets to create those goals and work towards hitting them. It’s about what you want to achieve, not the company you work for. You don’t need to have it all figured out in order for it to work out. If you don’t have it all figured out, you’re not alone. Many of us are just winging it and are still able to achieve amazing results. 

Lesson #2: You cannot do it alone

As an entrepreneur, you need to build a team before you are ready. Hiring a team before you’re ready means reinvesting in your company before it feels comfortable. When you build a team, you are setting yourself and your brand up for long term success. You cannot build a brand by yourself and trying to do it alone is the reason why so many small businesses fail. 

When you start hiring, you are able to release control on some tasks, which frees up your time for other endeavors. That release of control is so challenging but will help you continue to step into your role as CEO of the company. 

The first hire I ever made was someone to help with engagement for my clients. At the time, I was still working my full time job and was unable to find the time to do daily engagement tasks for my clients. So, I hired an engagement specialist to help with posting and engagement. Without that hire, Ninety Five Media would not be what it is today. 

Lesson #3: Don’t invest just because everyone says you should

Oftentimes we become influenced to make investment decisions based on what our peers are doing. The truth is, you may not need what everyone else needs. My best advice for this is to find what you are weakest in and invest there. 

For example, it could be onboarding new clients. Can you automate those tasks on your own? If not, what kind of software can you invest in to help you automate these tasks? Once this software is set up, you have more time to do the needle-moving tasks that only you as a human can do.

The first step is to audit your strengths and weaknesses and hire people or utilize software to fill those gaps for you. 

Lesson #4: Button up your contracts with a lawyer

When we start a business, we often start with DIY contracts because we don’t feel ready to invest in a lawyer to help us with our contracts. Yet, we would ultimately save ourselves a lot of money and stress by having them done by a professional to begin with. 

At some point in your business, you will need to fall back on your contract, especially as a service provider. We have dealt with this numerous times at Ninety Five Media and having a solid contract really helped secure money that we were owed. If you don’t already have a contract created by a lawyer in your business, I recommend that you prioritize that expense sooner rather than later. 

Lesson #5: Systems will be your best friend 

I am a huge proponent of having systems in place as a business owner. When I say systems, I mean creating workflows that you and your team can fall back on. As your company grows, you are going to find that you are having to repeat yourself a lot – so creating systems helps to streamline that process. 

By creating systems, you’re actually empowering your team or your clients to understand what’s supposed to happen without needing to involve you. When you look at systems in your business, there’s two different sectors. 

One is the systems you create for your team, and how you want them to execute tasks and what your standards are for how your team does things. The second sector is the systems for your clients so that they know what to expect and they know your boundaries. 

Lesson #6: Your role should change

When we start a business we typically wear a variety of hats and our role will evolve as our business grows. This all ties back to lesson number two of hiring before you’re ready. 

For example, say you hire someone to help with sales. Then that role is no longer on your plate and you can do whatever you want with that extra 5 to 10 hours per week. It would be best to fill that time with needle-moving activities that only you as the CEO can do. 

Take some time to audit what your role looked like six months, a year, or two years ago and make sure that your role has changed significantly. If it has not, that means that it’s time to release control. Doing this will help you scale much faster. 

This is one of the hardest lessons I have had to learn and every time I bring someone new onto the team, I make sure that I am crystal clear on the tasks I am passing off. This helps create great systems and workflows so that whoever is stepping into the role is set up for success. 

What often happens is that when we release control on a task and it doesn’t go well, we want to take back that task and never try to outsource anything again. It’s usually not the person doing the task’s fault. Instead it’s typically a reflection of the person who passed it off.  At that point, we need to look back and think “what could I have done better here?”

Maybe you could have given them more information about the project or shared some sort of tutorial with them. Think about what you could have done better that would have set them up for success, and then go back to the drawing board. When we experience this “failure” of passing off these roles, it makes us afraid to outsource again. 

The truth is, things don’t have to be that bad for us to pass them off. It just has to get to a point where someone else could do that task, potentially even better than you can. There are always going to be things that you cannot pass off so once you identify the things that you can, it’s really important to rip off the bandaid and hand them over. 

Lesson #7: Get your team invested in your vision for your brand

It is really important to take your team along for the ride with you. When we don’t share this information, it’s hard to expect a team to be invested in the brand that you are growing. Even when you are being extremely transparent with your team, you can’t expect them to ever be as invested as you are in the business. Your business is your baby and you should always be the one who’s the most invested in its growth, future, and scalability. 

The problem arises when your team is not invested at all. What we really want to happen is that your team is invested in the vision, and therefore they work with you to bring that vision to life. There is nothing more powerful than having a team who is backing your vision and wants to help your brand succeed. That is truly the secret sauce behind every successful business. 

Lesson #8: Entrepreneurship is a roller coaster 

There are going to be days where you want to give up and go back to corporate or just hide in bed. What’s going to keep you going is your why. 

It is totally normal to feel like it would be easier to go back to corporate some days. There is no other job where you have the pressure of running a business when you’re working for someone else. Even if you’re an executive of a company, you still have other people to bounce ideas off of and you will still always have a boss. There will always be ups and downs when you own a business so don’t give up the first time you feel down. 

Lesson #9: Have a greater mission than money 

If you started your own business just for the money, it’s going to be very challenging. There are a lot of ways to make money and being an entrepreneur certainly isn’t the easiest route.  If the money is all you’re in it for, then you should probably reevaluate. 

There has to be a mission greater than the money. This mission is going to help you get out of your funk on those hard days and come back to business with a fresh mind and burning passion to keep going. Just because your business makes a certain revenue does not mean that you are bringing all of that home. There has to be other indicators of success that you are on the right path with your mission. 

Lesson #10: Celebrate your small wins 

As entrepreneurs, we’re the type of people who create these massive goals, hit them and then move onto the next goal. We rarely take a moment or two to stop and celebrate. 

That can be very detrimental because then you are always striving towards the next goal. While there isn’t anything inherently wrong with achieving your goals and then moving onto the next one, it is so important to internalize hitting those goals. These will always be memories we look back on. 

In 2020, I created my first free offer that would build the company’s email list. I posted about the freebie in a Facebook group in hopes of getting just 20 sign ups. Within 24 hours, the post had gone viral and my list had grown from 0 to 500 people. 

I was so excited about it and shared the news with my coach later that day and my coach immediately asked how I was planning on celebrating this milestone. I said, “well I got a Starbucks this morning” and that could be my celebration. My coach stopped me and told me that I needed to celebrate in a bigger way so I bought myself a new ring. While I don’t make a new purchase every time Ninety Five Media has a win, when I look at that ring, I feel that same giddiness that I felt when I got those 500 signups to our freebie. 

Celebrating your wins doesn’t mean you have to buy a material possession. You should celebrate in the way that feels good to you. Doing this will help you manifest that feeling again and continue hitting those goals. 

 I would love to hear your biggest lesson from today’s episode. it would just mean so much to know that this helped you and that you are well on your journey prepped a little bit better than I was. You can DM us on Instagram at Ninety.five.media.

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