My Journey As A 20-Something Entrepreneur

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My Journey As A 20-Something Entrepreneur

My Journey As A 20-Something Entrepreneur

20 something entrepreneur

Leaving Corporate World To Become A CEO

I just couldn’t stop thinking about building my business – day and night. So on July 31, 2014 I left my amazing job as a Marketing Advisor at Constant Contact, and became a full-time, 20-something entrepreneur.

Before my days at Constant Contact, I had worked for a digital marketing agency doing web design, search engine optimization (SEO), display advertising, retargeting, and social media marketing campaigns for small businesses across the country. I also had a freelance gig on the side where I helped businesses in my community.

When the agency later filed bankruptcy, I had the opportunity to work at Constant Contact (a company I had admired for years) where I became a Marketing Consultant for small businesses and advised around 80 businesses/day on their marketing across the US, Canada, and UK. Then after 3 years in the making, working late nights and weekends, I had finally built up my freelance business where I was able to go off on my own and be financially independent.

My first month in business was just as I expected. I opened an office nearby, I attended a ton of networking events, I slept in, I did what I wanted and when I wanted, because I was the boss now.

Fast forward one month later, my biggest client (who was a key source of recurring revenue) came into my office, distraught, and said, “Lindsay, I’m having so many issues with money right now – I can’t pay your invoice.

“Don’t worry about it.” I replied.

I had talked to this client (a 50-something year old man with 3 successful businesses) at least 3 days a week for the last 2 years, so I knew his character, and I knew that this must have been a difficult conversation for him to have.

Knowing in the back of my head that he would eventually get it to me, I brushed it off and said “don’t worry about it right now, we’ll figure it out later I’m just focused on getting you to where you need to be.” After a 2 hour meeting, he went back to work.

The next day, he wasn’t responding to my emails or calls. I figured after our 2 hour meeting, he was busy catching up, so I didn’t think about it all too much. The following morning, I received a voicemail around 8:30am from his office manager asking me to call her back immediately.

It was then that I received the news, my biggest client had committed suicide the night of our meeting due to his financial struggles.

Shocked, disappointed, upset, in denial, angry, all of these emotions running through my mind – this was only my second month in as an entrepreneur and my whole world just went upside down. 

When you’re in business for yourself, every single day is a roller coaster ride.

One minute, you could bring on a large client that can change your entire world. The next minute, another one of your clients could file bankruptcy. You have to be prepared for anything that can be thrown your way.

As I look back, I think if it wasn’t for him, maybe I wouldn’t have made the jump to go out on my own. But his death was definitely a swift kick in the rear that I had to rebuild 3 years of work in the making to fill the gap of income I was relying on from him(&fast!) I figured, “well the only way is up from here!”

Fast forward to today:

A few takeaways from my journey:

  • Have a business plan and at least 6 months worth of income before you make the leap in case any curve balls are thrown your way.
  • Don’t refer business if you don’t know the business/individual’s work product. Just because someone is “nice” and you know they would take great care of a friend or one of your own customers doesn’t mean they we receive quality. (Think: you refer your friend to a really nice hairdresser & they leave the salon with a haircut from Edward Scissorhands!)
  • Be confident in your value & walk away from clients who don’t value your time or experience. I’m in business to help businesses thrive and have a mutually beneficial relationship with the business owner. If I wanted someone telling me what to do and not respecting my time, I’d go back to work as an employee.
  • Don’t forget to charge! Early on, I was cutting breaks left and rate to clients. I was running all over Massachusetts to meetings that usually were just people trying to pick my brain. One story I’ll always keep in mind when even considering cutting someone a break, is the time I met with a new client who was pleading with me that $150 was their max budget for marketing and they were on the verge of going out of business. After feeling “bad” and agreeing to take on the project, we walked out of the meeting and they jumped into a brand new Bentley. #NeverAgain
What lessons did you learn in your first year as an entrepreneur? Share them with me in the comments below!

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