HR & business leaders

10 Avoidable Startup Mistakes I Wish I Could Undo

My first year of business was a whirlwind of lessons learned, imposter syndrome, and in-the-face-grit. I had highs that put me on cotton-candy clouds as sweet as they looked, and lows lower than I can limbo—and I used to be a gymnast!

Let me try and bullet it out for you: 

➡️ March 2020: I was working as a content and social media manager for a coworking space. As you know, the world went into lockdown. My salary was cut to 70%.

➡️ April 2020: I picked up freelance writing to try to get back to my 100% income. 

➡️ July 2020: I walked out of that first lockdown with 4-5 clients earning more with them than my 100% salary with the coworking space. I quit the coworking job. 

➡️ June 2021: My portfolio of SaaS brands doubled. With each publication came more interest for my work.

➡️ July 2021: I launched dslx, a creative copywriting agency specializing in content for B2B SaaS. I brought on a part-time project manager and assistant editor. We recruited 60+ freelance writers for the agency’s books. 

➡️ September 2021: The dslx website went live, and my previously part-time employee agreed to a full-time contract. We onboarded two new clients. 

That brings me to today. What’s interesting, even in bulleting this last year or so, is that I chapter my progress by my wins—not by my losses. However, that doesn’t mean they’re not there. They’re just not what I chose to determine my success. 

My mistakes, failures, f**k ups—whatever you want to call them—were rife. Today, I keep them as lessons. Fail fast—I’m sure you’ve heard it before. Learn faster is something startup founders need to hear more of. We define our own narratives, both for ourselves and our businesses. 

So, in this article, I won’t be sharing my mistakes. I’ll be sharing my lessons learned because of them so that you can learn via them. Let’s go to school. *Hits CMD-Z*

Ray working on his laptop at a café

A photo of me making mistakes

10 Startup lessons I learned so you don’t have to 

1. Hire talent you know 

I know this one is controversial. HR pros will tell you that you run this risk of limiting diversity and, therefore, innovation when you run in your circles. However, I’m not talking about full-time hires here. I’m in the world of gig-work, and I needed people I could depend on. I also loved the idea of building something with people I’ve helped build. 

Some of my clients today were my interns in previous roles. They’re now out there crushing it in SaaS. 

My illustrator for the monsters on my website I met at a yoga retreat in Spain. She’s now completing her studies in Sweden.  

My logo designer was an intern I had at the coworking job; she’s now living and working in NYC.

My now full-time hire was also an intern from the coworking job. I had coached her over a nine-month internship to become the talented writer she is today. 

I’ve been able to trust these people. They’ve helped me build what I have today, and I’m very grateful they were and are a part of it all.

One of dslx's first monsters

One of the many monsters that featured on the first version of the website

2. Be transparent with what you can afford 

If your startup is self-funded, then there’s a high chance you will be a little strapped for cash in the beginning. That’s okay, but be transparent about it before you entertain buying any services from someone. 

Your budget should be one of the first things you mention. By doing so, you’re managing expectations, and a freelancer can either say: “hey, this isn’t for me” or “hey, let me adjust the scope of this project to be within your budget.” 

When you’re transparent with what you can afford, you save everyone time and any awkward conversations further down the line. 

Just a note: I don’t think entrepreneurs talk about money enough. We seem to have developed this toxic relationship with it, in which it’s taboo to talk about costs. Let’s change that. 

3. Don’t get greedy 

Talking about money brings me on to my next point, don’t get greedy. It can be so tempting to say to yourself, “hey, I’m doing well; I’m going to charge more.” Charge more because you deserve to be paid more. Maybe that’s because you’ve completed a course, you’ve upped your skillset, you’re offering more services, or your product has developed. 

Don’t charge more to see if you can get more—especially not from your current clients. They’ve been good to you, so be good to them. 

4. Say no to contracts that don’t serve you 

This is a tough one and one that I wish I had done. However, lesson learned. Say no to contracts and clients that raise red flags. If you can spot the red flag in the first place, that’s enough of a signal for you to steer clear of that client. 

No matter the size of the contract, it is not worth the stress and the detriment to your mental health. So, put yourself first, know your worth, and say no to things that will lead you astray from your mission or cause you to be unhappy. 

5. Own your niche 

This is a lesson I’m still learning. It’s something I knew I should have done from day one, but in my excitement, I wanted to do it all—rather than own my niche. My niche is B2B SaaS. It’s what I know, it’s what I’m good at, and it’s 90% of my client base. 

With clients referring new clients in the same field, it’s also a niche that’s growing. Yet, I launched dslx saying we’d do it all! 

Maybe we will, in the future. But, right now, I need to knuckle down and stick to what I know, with what I’m good at, and with what I have handshakes in. That’s B2B SaaS. If you see me going for anything else, give me a clip round the ear and tell me to focus.   

6. Find your USP and shout about it 

What is your unique selling point? What can you and your business achieve that no one else can? What sets you apart from your competition? Market research for startups is so essential for nailing what you stand for and understanding your uniqueness. 

For example, I’m dyslexic. I never thought I’d lead a business with my dyslexia at the forefront of it all. It’s something I’ve hidden from the professional world my entire life. However, when I spoke out about it, I was met with a resounding yes, and it rapidly transformed into my USP. 

dslx is a mission-driven agency. We empower dyslexic and diverse writers to write. We show writers that your diversity is your superpower. I hope we can show writers how to harness their superpower so they can thrive in doing what they love. 

7. Hire outside of your skillset

As a startup owner, you’ll want to do it all. You’ll want to have your fingers in all the pies, and who can blame you!? We’ve got blueberry over there, apple over here, the one in the corner is a meat pie that tastes just like the one your grandmother made when you were a child. Get where I’m going with this? 

We can’t have it all. As much as we want to, business owners need to let go of the things they don’t excel in and hire experts. Make time for why you started your business in the first place, and don’t get caught up in things you don’t enjoy. 

One of the first things I did was hire an accountant. I detest numbers. I used to call them letters when growing up. I detest them because I’m not good with them. Outsource your resources, and stick with what you know.

Ray Slater Berry talks on the mistakes he made and lessons learned in launching a business

I had just signed a client when I took this photo 

8. Ask for help 

Do not be afraid to ask for help. There is ZERO shame in it, and you’ll be surprised by the number of people who will jump at the opportunity to help you. 

Help comes in different shapes and sizes. Maybe it’s a share of a social media post, maybe it’s an introduction to a potential client? Ask for help, and it will come knocking. 

9. Look after your clients before acquiring new ones 

Another mistake I learned quickly. In my eagerness to grow, I said yes to a lot of clients that came my way. This meant yes to client projects that started the next week, and I lost sight of those clients who had been with me for months. 

I cannot stress enough, if you’re on the service side of things, to prioritize your current clients. They’ve been with you for the long run. I’m not saying new clients will churn, but your old clients deserve just as much attention as they did on day one. 

10. Shoot your shot & share your journey

You are the first and last person you can rely on to have your own back. I’m not saying this because something negative happened to me; I’m saying this because I shot my shot, and it paid off.

A screenshot showing goal.cast's Instagram page where they featured Ray Slater Berry's Instagram reel

There I am, beating Simone Biles to the podium—who knew!

I made one video on TikTok about my business journey and where I am today. That video took off. It got picked up by an Instagram account called Goalcast that shared it with their 1.9 million followers and racked up 911k views.

From that one TikTok video I was:

➡️ Invited to talk on two podcasts, The Invernadero Mind Podcast, and the ​​intuitionology podcast 

➡️ Invited to share my story at Neurodiverse Pride 

➡️ Runner up in the UK’s Next Entrepreneur Competition 

➡️ Invited to become a storytelling coach 

➡️ Able to acquire two new clients 

➡️ Inundated with writers’ applications that believed in dslx’s mission

A snippet of Ray Slater Berry's viral reel about becoming a dyslexic founder or a content writing agency

The TikTok video that sent my story viral

At the same time, I garnered thousands of new followers, fans, whatever you want to call them, who believed in me and my journey. They’ve sent me messages of encouragement, and have told me they’ve started writing again after seeing my videos. For some, it was the nudge they needed to go freelance themselves. They now hold me accountable for my progress, and I’m extremely grateful for that. 

Got it? Now go and make mistakes 

So, I’ll leave you here and tell you to get out there. Go and make mistakes, learn your lessons, stay on your toes, and build a business you’re proud of. 

Note: you’re not allowed to make the same mistakes I did if you got this far in the article. 

The biggest lesson I hope you walk away from this post is, we write our own narratives. You only f**k up if that’s what you choose to label it as. 

Now get out there, make mistakes learn lessons, and create a narrative that no matter how many times it reroutes, pauses, or all-together pivots will still lead you to success. 

I am the text that will be copied.