Why I Left My Dream Job to Go Out on My Own

In early 2019, I was given the opportunity to work for a company (Roofstock) that I had long considered my dream job.

Roofstock was my gateway into real estate investing in 2017. I bought 2 properties that year and was hooked. All I could think about was growing my little portfolio to the point where it paid for all our expenses.

To be able to help spread the word about real estate investing and get other people started on their own investing journey has been a unique experience that I tried not to take for granted.

During that time, our team achieved some pretty amazing things:

  • We grew the blog from basically nothing to over 175k monthly visitors
  • We dramatically reduced our customer acquisition costs and hit new records in activity on the marketplace during a rocky year
  • Started a podcast on remote real estate investing and grew it to over 20k downloads per month in less than 9 months

But today was my last day as an employee at Roofstock.

Here’s why (and what’s next)…

As an investor, I spend a lot of time thinking about the future. I’m delaying gratification today (i.e. foregoing a bigger house, nicer/newer cars, etc.) for the goal of financial freedom in a decade or so.

But that got me thinking…

If I were to hit that goal tomorrow, what would I do with my time.

Sure, I’d surf more, read more, spend more time with friends and family… but then what? Knowing myself, I’d need some other pursuit to keep me fulfilled.

So I dug deeper. Maybe I’d help people invest in their own deals once I had enough experience under my belt to actually give good advice.

Or I’d use my skills as a marketer to grow websites and monetize them. It’s basically what I’ve been helping companies do for the last 6+ years and I love the game.

And then it sort of hit me.

What’s stopping me from doing that now? I’ve been dreaming about starting my own business for years – why put it off until later in life?

Some were excuses, but it mostly boiled down to the safety and security of a steady paycheck. We have a mortgage and a toddler, with plans for another kid at some point.

But what if I just remove some of that financial risk by starting a service business instead? Instead of growing my own websites now, I can help multiple companies do it as a consultant. I already do some SEO work as a side hustle, so I know I can scale it out if it has my full-time focus.

There’s also the monetary component. I have friends who run marketing services businesses and they make a great living. This would give me the opportunity to be in control of my earning potential (for better or worse), and being able to earn more means I can funnel that into more small multifamily investments.

So after months of deliberation and long conversations with my wife, I’ve decided to finally take the leap and start an SEO consulting business.

I’ve wanted to go out on my own for years, but the same excuses kept coming up…

“Is now the right time?”

“Can I really get enough clients to replace and surpass my salary?”

“I’ve been consulting on the side for years, but can I really turn this into a full-time gig?”

I’ve realized there will never be a perfect time. Luckily, I’ve built up a bit of a financial cushion and have been having conversations with a couple of companies to get started with when I did decide to make the move.

Another thing that helped me: realizing that the worst thing that could happen was that I would have to go back and get another job as a full-time employee. I hope to never be employed again, but it’s good to think about your worst case scenario and realize it’s not the end of the world.

So here we are. Day 1 of going out on my own. I’m super excited to start growing my client base and helping awesome companies attract more customers.

Hopefully in a year, I’ll get to look back on this exciting and anxiety inducing time and realize it was the best professional decision I’ve ever made.

While you're here...

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2 Responses

  1. Hey Emil! Loved reading this blog post — gave me a lot of inspiration as well 🙂 I’m glad you’re doing well and venturing out on your own!

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