All my failures as a business owner so far

When I created my podcast, I knew I wanted to do an episode on my biggest business owner failures because if you look at people’s lives on Instagram or through their email lists, it might seem like everyone is doing great and everything is amazing. But from my many one-on-one meetings, market research, networking coffee chats, and various interactions, I’ve realized that behind closed doors, it’s a different story. A lot of people are facing unprecedented challenges in their businesses.

Several factors contribute to this. First, there’s a lot of uncertainty within the economy, leading to a scarcity mindset. People aren’t assuming they’ll make the same amount they currently do, so they’re hesitant to commit to bigger purchases long-term. Additionally, we’re experiencing a bit of a downturn from the COVID boom. During the pandemic, people were excited about trying new things, new programs, and new services. Now, they’re either satisfied with how things are, have already done it, or have decided they don’t want to.

So, for this last episode of season one, I wanted to be real and vulnerable. I’m unfiltered, after all. Let’s dive into my biggest failures as a business owner so far, what I’ve learned from them, and what you can learn too.

My 5 business owners failures

1. The delusional math of starting a business

My first failure was the delusional math I did to decide that I was going to create a business. Initially, I thought I wanted to be a motivational speaker. I did some really bad back-of-the-napkin math: “Oh, all I need is this much to live, and if I book this number of speaking gigs a month, I’m good.” What I didn’t account for were taxes, health insurance, and the effort required to book gigs.

Regardless of the business, be it speaking gigs, clients, or selling courses, there’s always a funnel involved. It’s not just about needing to book five gigs a month; it’s about understanding how many leads you need to find those gigs. If I need five gigs, I might need to find ten interested people. And what does it take to find ten interested people? Maybe I need to go to a networking event every week and find five ideal clients there.

You have to back up from your target number to understand how achievable it is. However, it’s impossible to know all of this starting out. If I hadn’t been delusional, I probably never would have left my corporate consulting job and started a business.

So, the lesson I learned was: you have to pay your taxes, and you can’t just do simple math without considering all the steps involved. Think about the cost in terms of money and time to achieve your goals.

2. The Galentine’s day gift box

My second failure was my Galentine’s Day gift box. In 2021, I decided to create a gift box for Galentine’s Day. It included a cute hat, a cozy, some artwork for your desk, and more. At the time, I had 400 Instagram followers and about 22 people on my email list. I confidently purchased 100 hats, thinking I could convert 25% of my followers into customers.

I spent a ton of time setting up WooCommerce on my website, taking product photos, and creating content. Ultimately, I sold seven boxes, mostly to friends and family. Now, I’m stuck with about 70 hats and 35 cozies.

The lesson here? You’ve got to validate your offer before creating something you think everyone will like. Without having your ideal buyer tell you they want your product, you’re setting yourself up for disappointment. Market research is crucial.

3. My first podcast, “Overcoming Should”

My third failure was my first podcast, “Overcoming Should.” In this podcast, I interviewed people about different “shoulds” and included insights from a therapist. I did around 20 episodes and decided to stop because it took a ton of effort and moved the needle zero for my business. It was a passion project that cost me time and money without any return.

I learned a lot about podcast logistics, but creating a podcast is a lot of work. If it’s not moving the needle for your business, it might not be worth the time investment unless you’ve won the lottery. I also learned never to do a podcast with two guests on every episode; the logistics are just too complicated.

4. Misguided target audience for my first course

My fourth failure was launching my first course, Create with Confidence, initially targeting nine-to-five professionals. I had experience with marketing and communication roles and thought they’d benefit from learning design skills. However, nine-to-fivers are less likely to invest their own money in courses.

It wasn’t until I pivoted to targeting business owners that the course enrolled students more easily. Business owners are more likely to invest in courses because they know it will benefit their businesses directly. The lesson? It’s easier to sell to those who benefit directly from your offer.

5. Forgetting what works can be business owner failures

My fifth and final failure is neglecting what works. Often, when I get booked with client work, I abandon the marketing strategies that helped me book those clients in the first place. I stop networking, promoting myself, and doing the things that got me there because I’m too busy.

The lesson here is to consistently and sustainably market your business. Reflect on what’s working, do less of what’s not, and keep doing what’s working, even when you’re booked. Consistent marketing is crucial to avoid a deficit when clients fall off.

Free resources to grow your business

For business owners who want to attract ideal clients and close sales: Check out my free crash course, 3 Simple Steps to Profitable Branding.

For service-based business owners: Watch my free masterclass, 5 Things Your Homepage Needs to Book More Clients, co-created with Emily Conley.

The podcast for service providers, coaches, and freelancers

marketing strategy, online business growth, and work-life balance

Definitely Tune In!

I got a sneak peek before the launch and I definitely recommend a listen!! Felter is candid, informative and full of insightful content for business owners!! I am so excited to continue following along and listening to the podcast; it’s transformative and helpful for anyone willing to put in the work to succeed!! ??

-Apple Podcasts

hosted by:

Lauren Felter

owner of Felter Unfiltered | the designer that non-designers love

Get all the service-based business strategy

sent to your inbox every week

Website Lead - SAF Podcast