I love to mine my experiences for lessons. I feel so lucky that I get a chance to start over and do things differently with all the lessons I’ve learned from my experience building my first business.

During that seven-year journey, I experimented with dozens of different strategies and tactics to scale it. Here’s what worked, and what I’m absolutely doing differently next time.

I hope these lessons help you if you’re considering starting a business or adding a subscription product to an existing business.

What Worked

Systems that kept things running smoothly

There’s nothing more satisfying than an airtight system, right? Just me? In my first business, which focused on helping people meal plan for the week, having a seamless internal system was key. Subscription models thrive on streamlined systems. Without them, providing consistent content, services, or products to our customers would have been a chaotic nightmare. So, I dove headfirst into finding ways to automate and speed up our process. This not only made everything run like a well-oiled machine but also gave us a stress-free work environment.

Community

My company fostered a positive, open-minded, compassionate community. Showing up consistently is the key to building a thriving online community. That alone made all the difference. My brand attracted the kindest, most welcoming folks who were just as excited as I was about everything food and cooking. It was amazing to see how our Facebook group flourished over the years. We kept moderation light and mostly let our customers share their mouthwatering food photos. It was (and still is) one the safest spaces to talk about food without diet culture getting in the way.

I want to make it clear that my company, its systems, and the community are still going strong. I may not be at the helm anymore, but they’re still thriving!

Differentiation

Let’s face it, standing out in the online world can be tough, especially in the food industry where competition is fierce. But even in a niche like meal prep, I found a way to rise above the noise. How did I do it? By taking a stand and deciding not to participate in weight loss and diet culture. Instead, I focused on Intuitive Eating, which no other meal prep company did. It was a bold move, and it meant turning away potential customers who had weight loss goals. But you know what? If you want to be different, you’ve got to do it with confidence. I never shied away from being loud about the anti-diet philosophy behind my company. That unapologetic approach helped us carve out our own corner of the market.

Another aspect that made us different was the custom software for meal planning that our members used online. While many custom meal planners exist, going in this direction allowed us to design a meal planning platform that aligned with our values.

Offer, Price Point & Demographic Alignment

It took me two years after starting my company to figure out a product that solved the right problem, at the right price point, for the right audience. But once I did, it really took off. The price point I ended up with did present some challenges down the line, but ultimately I knew it was the right move.

I’m glad I experimented with different products and prices, even though those first two years were tough. Keeping a weekly content subscription alive for 5+ years is no small feat, and the price point I chose allowed me to have the volume of customers to keep it going.

The Team

When I thought about starting and owning a business at age 24, I couldn’t wrap my mind around the idea of having a team. But as time went on, I couldn’t deny the value of having a team of incredible individuals. We started with contractors and eventually grew into a small team of full-time employees. I couldn’t believe that these talented people wanted to work with me and my company for as long as they did. It was a humbling experience. They were self-starters, full of positivity, and a joy to work with. Their creativity and reliability truly took our business to the next level.

Other things that worked for me:

• Flexibility during the workweek.
• Having work that kept the creative juices flowing.
• Being able to pivot easily as needed.

What I’m Doing Differently Next Time

Start With Standalone Digital Products

One big mistake I made in my first business was finding success with a subscription product first. While having a subscription product allowed me to quickly go full-time with the company, it made creating new products challenging. Even with an amazing system, subscriptions require regular weekly attention. We had to create new content weekly which left little time to focus on building something new. We attempted to build a few standalone products, but I think I was already too burnt out to push them to the finish line.

Next time, I’m switching it up. I want to find success with standalone products like ebooks and self-guided courses or other digital products first before launching a membership or subscription service. Failing to get other products aside from the subscription off the ground held us back from overall company growth and supporting the community.

Pricing

I learned the hard way that my target market in my first business was not going to include “premium product” customers. This became clear during the first (and only) time I launched a $200 product around meal planning and accountability.

So while making the choice to have a commodity product (the subscription was originally $7.99/mo) helped us grow quickly, it meant the business required a high volume of customers to join each month in order to grow.

In the five years I ran the subscription, we had over 25,000 people purchase a membership. That is absolutely wild. But even with a healthy churn, keeping the numbers up was challenging.

In my next business, I plan on having a range of products with different price points to avoid this pitfall.

Diversified Marketing Channels

When just starting out in business, a common piece of advice is to focus on and excel at one marketing channel instead of trying to master them all. I did that with Instagram, but kind of stopped there. We dabbled in TikTok, YouTube, Facebook and Pinterest over the years, but nothing stuck like Instagram.

It got to a point where feeding the Instagram beast was so demanding that we struggled to give the time and attention to other channels. Many businesses struggle with this, but it’s important to figure it out.

When Instagram stopped working for us, we scrambled to figure out other channels quickly, which ultimately didn’t work. We didn’t feel like we could pull the plug on Instagram either, and continuing to share content on a platform that hardly moved the needle for us felt soul-sucking.

In the future, I’m going to spread the love more and work on growing multiple channels even if it means slower growth. I’m excited to figure out a sustainable way to post across multiple platforms long-term instead of directing all resources to one and figuring out the rest later.

Collaboration

I’m a lone wolf who wants to be a collaborator. I had many opportunities to collaborate in my business that I didn’t dive into because it felt like too much of a lift. But I know how important relationships are, not just for business, but for mental health and learning! I feel I could have learned a lot more and had more opportunities for growth if I had collaborated frequently with other founders.

This one is more for me, personally, but I want to build collaboration into my next business. It’s a good way to learn, open my mind to new possibilities and serve my customers and community with different types of resources.

Built-In Giving

Leveraging my business to give back and donate was always on my mind, but I never executed it. Like collaboration, I want to build a system for giving back in my next business. It’s important to me, but I had no idea where to start. Therefore, I never started. Next time, creating a system for giving will be a top priority to figure out early on. I’m excited to get creative with this and learn how to consistently give back to communities and causes that align with my values.

Contractors Instead Of Employees

Things can change — maybe I’ll feel differently in a few years. But I think moving forward, it’s better for me as a manager to stick with hiring contractors instead of full-time employees. I never felt like I gave enough to my employees (even though I know I gave them a lot) as a manager who could develop their talent. I think I’m being hard on myself, but I truly believe they deserved more from a development standpoint.

This is hard to talk about and I hate to admit this, but having employees negatively affected my mental health in a way I didn’t realize until I had to let them go due to financial reasons. It’s probably because I was so burnt out, but I didn’t realize how much pressure I had on myself to support the company AND the group of individuals helping me support the company. My burnout made me feel like I was constantly letting the community and my employees down.

After their last day at my company, I felt some of that relief. I also felt guilty for not being able to pay them more. I know I did my best when it comes to salary, but I knew they could be making a lot more somewhere else and dreamt of being able to compensate them more.

Other things I’m doing differently next time:

• Work with an SEO expert sooner. I left so much money on the table.
• Just make the damn mobile app! I should have broken ground on that earlier.
• Experiment with paid advertising more. I was always so resistant to doing more of it.
• Never have sales or discounts. It created a volatile cash flow situation for my business.
• Design a business that doesn’t require me to work on weekends or change how I eat to produce content.

It’s interesting how some of what worked also posed challenges.

After reading this back, I noticed that pricing and having a team appeared on both lists. And the systems I mentioned in the first section, were also what held us back from making new products (mentioned in the second section).

I guess my takeaway from this is… it will never be perfect and some strengths in businesses can also present as weaknesses.

If you enjoyed this post, I’d love to connect with you in my newsletter! Sign up here to read it on the first of every month when it drops.