How a Single Tweet Became the Start of My Entrepreneurial Career

This is how my company wouldn’t exist and I wouldn’t be doing what I’m doing now if I hadn’t reached out to a particular someone on Twitter.

As part of my “Actionable Guide of Where to Start When Looking for New Clients”, I mentioned something I have found to be very, very important:

Never underestimate any conversation you have with anyone, anywhere, at any given time.

This has proven to be so important and significant for me and here’s why.

8 years ago, I tweeted out a question to a real estate agent regarding a condo development I was interested in. He was extremely helpful, down to earth, and gave a lot of great advice on investing in the condo market in general. We continued to email and tweet back and forth for a bit.

I referred him to some family and friends who were talking about investing in a particular condo because I thought it would be really beneficial to have him on their side.

One friend met with him and purchased with him. Said he was great. Another family member decided to meet with him and I thought it would be a good chance for me to come along and meet him as well.

We met, they purchased, and he shook my hand saying he’d like to take me out to lunch as a way to say thank you for the referrals.

At this point, I’m working in retail, still in university, and really have no idea which career route I want to go with my life (which is a looooong story on its own). So there’s no real agenda here.

We went for lunch and we got to talking about how I found him, the market, my interest in the market, what I do, what I’m interested in etc. He told me about what he’s trying to do with his real estate business as well.

Not thinking anything of it, I told him I worked for Apple at the time, and I help users with purchasing Apple products and learning how to create stuff on them as well. I said if he ever needed help with anything to let me know, I’d be more than happy to help.

He mentioned I could be a good resource for him. I said thank you for the lunch and the advice he’s given me and that was that.

I decided to email him later on and say if he ever need help with anything I could help him on an hourly basis or whatever.

He was interested and so we met again and we agreed on an hourly rate for whatever he threw my way to help him with paperwork, his website, online ads, etc.

15 hours per week of admin, blog posting, Google Adwords, website changes etc. This was the beginning of Yolevski Creative Media.

I’m going to skip a bunch of stuff and just say this continued for a couple years, then decreased in hours a bit when I began working at a startup in downtown Toronto.

After working full time at a startup for 8 months, doing quite well, he reached out to me and told me he wanted to meet with me again.

He said he loved the work I was doing for him and wanted my services full time. He wanted me to help him build his brand in a more involved role.

This mean’t leaving my job with benefits, comfort, sustainability, and any possible future there. On the other hand, this moment gave me the opportunity to become the entrepreneur I had always been itching to be.

He said I could take him on as a client, and I’d still have time to get other clients and grow my business. He knew of my previous career changes, and my constant need to try something new and on my own. He understood all this about me and spoke to these needs.

He gave me the opportunity to start my own business with the financial security of a guaranteed first client.. a big consistent first client.


This is what I would consider a starting entrepreneur’s dream.

I couldn’t pass on this opportunity and go back to a typical 9–5 job (even though the startup was very cool and not a typical office job. But still, it wasn’t mine).

So basically, without him I wouldn’t be where I am today and he is still my biggest client and I couldn’t be more proud of the work we do together.

This all started from a single tweet. Lesson?

Never underestimate any conversation you have with anyone, anywhere, at any given time.

You always want to be the best version of yourself at all times regardless of who you are speaking, being introduced to, or just infront of.

Because, well, you never know.

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