Entrepreneurs share what stopped them from starting their first company

Nick Swekosky

Nick Swekosky

CEO of Market Metrics

The first thing that stopped me was a lack of an existing community to use our service.

My first company was an event-based marketplace that made it easier for consumers and businesses to connect through live experiences.

To solve the chicken-and-egg problem, we created a “Tinder for Events” app and seeded it with Eventbrite events.

Once we gained an initial user base of approximately 2000 consumers, I quit my job and began onboarding businesses.

Market Metrics

Neal Chauhan

Neal Chauhan

CEO of ToySoldierStudios

While I didn’t realize it at the time, I found myself crippled with a fear of perfection before starting my first company.

I wanted to offer clients the best service with the best products, and didn’t want to get started until I was able to do that.

After months of self reflection, I realized that the “perfect product” couldn’t exist until I embraced failure, and improved my skillset over time.


Petra Beumer

Petra Beumer

Mindful Eating Institute

Fear of going out on my own. Fear of letting go of the ledge.

Fear that manifested itself as a small mindset, which was conditioned by my working class upbringing.

My passion and my calling were stronger and I pushed through those fears and false beliefs.

I have never regretted my decision for a second.

Three years later I am still self-employed, fulfilled and very grateful!

Mindful Eating Institute

Jessica Williams

Jessica Williams

JMW Career Consulting

These 3 areas held me back for 5 years until I got truly fed the hell up I just decided to jump with blind faith.

  1. I did not recognize how many programs, marketing structures, and operating systems were required to make a company run.
  2. I was unsure if I would succeed in a highly saturated industry such as career coaching and resume writing. I talked myself out of researching the industry and held myself back.
  3. I had no idea how to run a business, I was always an employee not the Head Woman In Charge.

JMW Career Consulting

Paul Burke

Paul Burke

VP of Simple Slides

It took me over 40 meetings to find the right co-founder.

I was right out of college working at a startup and wanting to partner with someone technical to build an app.

While some people just weren’t a good fit, most people flat-out rejected my offer.

I actually told myself I wasn’t going to pursue the idea any further until my very last meeting I connected with the person who would eventually be my co-founder.

That propelled me to keep going.

Simple Slides

Jessica Rose

Jessica Rose

CEO of Copper H2O

I wanted to start my first company for many years, but was stopped by self-doubt and the belief that it was impossible to successfully start my own business while still working a traditional 9 to 5 job.

This was obviously a false limiting belief, as I eventually managed to successfully start the business and grow it for two years while having a full time job.

My biggest tip for those who dream of starting a business is to take the plunge and hustle on the side while continuing with their full time job.

While it will make for a busier working life, it can be done and it will permit you to test the waters before jumping into entrepreneurship full time.

Copper H2O

Mony Gueorguiev

Mony Gueorguiev

CEO of Maidily

I was overwhelmed and afraid of stepping into the “unknown” because I had no experience in starting businesses, coupled with the fact that it would require a financial investment.

After a long time of feeling tired of being in the “rat race”, that feeling overpowered my fear and I decided to take the leap and start my own e-commerce business.

Eventually, I sold the e-commerce business, after building it into 6-7 products across 3 brands.


Ambra Schillirò

Ambra Schillirò

CEO of Social Cloud

I wanted to start a company in China as early as 2010, but it wasn’t until 2014 that Social Cloud was born.

What stopped me those 4 years was a lack of confidence, since for me being an expert in marketing and communication was not enough as the country was completely different than my own.

I spent 4 years working on my knowledge and connections, and during that time met my future business partner, which gave me the strength to make it happen.

It also really helped that my father pushed me a lot to chase my dream.

Social Cloud

Connie Vanderzanden

Connie Vanderzanden

CEO of Accounting Department, Inc.

I had convinced myself no one would pay me, and my full-time job I hated gave me comfort and security.

My mind could not make the connection that what I was doing for my employer at the time, and clients were happily paying for, would be the same thing I would do in my new business venture.

Having money conversations and selling the services and ultimately myself, was just not a skill set and comfort level I had 19 years ago.

At that time, I didn’t know any entrepreneurs, my entire family was paycheck-to-paycheck employees.

Money was something you earned to pay for things you already bought.

That lack mindset about how money flows is dangerous for a small business.

It took me many years to learn how to look at money and resources differently.

Profit With Connie

Blake Burch

Blake Burch

CEO of Shipyard

Originally, I felt like I didn’t have enough experience to start a company.

Despite many years of experience with big brands and learning tons of skills across role, I had never seen the inner workings of a SaaS-based business to feel confident in building one from the ground up.

I realized there were many people running businesses that were younger than me and who had less experience, so I decided to take the plunge myself to avoid continuously making excuses for why I wasn’t doing it.

Being open, adaptive, and resilient is all you really need to get started because it will help you gain all the experience you be successful since you will figure it out along the way.


Krista Neher

Krista Neher

CEO of Boot Camp Digital

I was approached by a business to do consulting and training on social media, but prior to that I hadn’t thought about starting a business.

I didn’t have a business plan or know how to setup a company, so I was intimidated by the setup and red tape. It seemed overwhelming to get started.

My mentor told me that I didn’t actually need any of those things, just focus on getting people to pay you first, then do the business setup.

I signed 3 clients before I even had a tax ID or business name.

I started my business with revenue, not business planning.

Boot Camp Digital

Charlie Camisasca

Charlie Camisasca

CEO of The eCommerce Boardroom

Misaligned priorities prevented me from starting my first company.

I always had this deep-seated desire to start a business, but other things always came first.

I’m all for work-life balance, but the reality is that entrepreneurship requires a singular focus, especially in the early stages of your venture.

You need to be very intentional about carving out time to further your business goals.

Eventually, you will form the necessary habits to keep improving and growing, and forming these habits was integral to getting my business off the ground.

The eCommerce Boardroom