Why I Struggled As A First-Time Entrepreneur

I was 25 years old when I started my consulting business. My focus was on social media marketing services for small to medium-sized companies…or so I assumed.

The American dream of my business venture began in my neighbor’s kitchen as we huddled around her laptop designing my logo and coming up with my business name. The next day I found a printing shop that produced my high quality business cards with an embossed finish on thick, white card stock (they were pretty kick-ass looking cards). The day after, I started meeting with everyone and anyone that would take a meeting with me.

I still cringe at my first “accounting” software (MacFreelance) which gradually evolved to Quickbooks after I got over my initial fear of numbers. Every day was a roller coaster of meetings, proposals, luncheons, more meetings, speaking, follow-up calls, and trying to find time to do the actual work I was pitching!

In hindsight, I wish I knew about the agile/lean business models and was able to validate my product/market fit long before I started pounding the pavement. I also realized that despite my fear of numbers I needed to sit down and map out my sales projections and lead generation pipeline. Instead, I wrote a 10-15 page business plan that I never executed on and was more appropriate for a business plan competition than an actual startup marketing plan.

If you’re thinking of starting a business or are already a business owner but struggling like I was, here is my advice I want to share with you after being in that situation…

1. Swallow Your Pride and Ask For Help. After months of sending out proposals and no deals, I finally sought out help in sales/marketing and got honest feedback. It was hard to sit there and hear everything you are doing wrong, but I was determined to figure out how to correct it.

2. Know Your Strengths. I tried to be anything and everything in my business and it left me spinning my wheels and frustrated. After complaining of this feeling multiple times to a mentor and good friend, he said “I’m not going to help you until you take a Strengths-Finders test and a Myers Briggs.” I knew what skills I possessed but I didn’t know how I naturally fit best in my business and how that would affect it’s long-term growth. I learned I’m passionate, a natural communicator, process-driven, insightful but get bored easily doing same tasks over and over. I also discovered that I could apply these characteristics to my personal branding.

3. Learn When To Say “No.” When you are an entrepreneur, your time is literally divided among a dozen or more tasks each day. It may be tempting to take on additional board positions, have a coffee meeting with a mentee or consider a potential partnership. However, make sure to mentally take a step back and ask yourself what true outcome do you want from it. If it doesn’t generate that desired outcome, just politely decline or instead offer an alternative solution.

4. Execute, Measure, Learn…and Execute Again. After a few attempts at trying to execute on my own company’s lengthy strategy plans, I instead turned to agile/lean methodologies and focused on executable projects broken down into measureable deliverables. I created my own marketing “experiments” as well as with other clients to focus more on market validation, channel testing and scalable marketing solutions.

5. KNOW Your Customer. The reason you started a company was to solve a problem. You can’t be a solution provider if you don’t really know your customer’s behaviors, thoughts, emotional connections, and their painpoints. Before you even consider a product/service launch, spend a couple of months gathering as much customer research using methods such as face-to-face interviews, usability testing, ethnography research, user stories, buyer personas, and such. Oh and don’t forget to document, document, and document some more all this valuable research.

I’m happy to share additional tools and resources (as well as more lessons learned) so please feel free to comment or reach out to me.