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  • Blake Nubar became a successful entrepreneur after starting and navigating four failed startups.
  • Mastering digital marketing and pivoting from agency-style work to products was his turning point.
  • He now runs a digital marketing company, invests in real estate, and travels extensively.

This as-told-to essay is based on a conversation with Blake Nubar, a 36-year-old business owner in Florida. Business Insider has verified the financial claims. This story has been edited for length and clarity.

I studied business management in college, focusing on entrepreneurship, and graduated in 2011.

I was dead broke, so I started on a traditional career path. I dreamed of entrepreneurship but didn’t have the money to start there.

Nearly 15 years later, I’m now a successful entrepreneur making six figures a month from my business, but it took a lot of failures to get here.

My first job was at an engineering firm, which funded my first startup

I used my paychecks to fund my first business venture, Footpriint, a mobile app that allowed college students to access campus events. I had never developed an app, so there was a huge learning curve.

I created a spec document outlining exactly what the app would do and then hired a development team on Elance (now known as Upwork).

Due to my inexperience, I didn’t know that the resources needed to pull a project like this off were far greater than I could supply. Funds became tight as I got further into the project, and I couldn’t invest anymore.

After my first startup failed, a 9-5 job was still not how I pictured my future

Being told what to do at my job and when, and essentially being capped at what I could earn, didn’t align with how I saw my future.

I next started a business in 2012 called Learn Everywhere, a digital product business that failed soon after.

I left my engineering job in 2013 and took a job at a private equity company that funded startups. This new job gave me more income for my next idea: a company called Orator that my friend Ace and I started together.

Orator was an educational company that transformed learning material for students into a visual product. It failed two years into its existence due to a lack of knowledge of how to market and sell and the amount teachers were willing to spend on learning material.

I was invited into my fourth startup in 2015

While I was still working at the private equity company, one of the investors took me out to dinner one night and asked if I wanted to join him in starting a fitness company selling supplements to end consumers and educational materials to personal trainers. With a background in developing educational material, this seemed like a no-brainer. I left my job at the private equity company the next day.

Our first big project was to create a personal training certification. I needed help, so I began team building. I brought Ace on and hired a sales rep and an internet marketing specialist.

We spent nine months building the product, a full course that included a book, mobile app, training videos, resources, and templates. When we were finally ready to sell it, we couldn’t. I had no background in digital marketing then, but I decided to learn it out of frustration of not making sales yet again.

In 2016, I left the fitness partnership to pursue online marketing

I had enough savings to live lean for a year. I invested every waking minute in developing the skills needed to become a successful online seller.

I started to help business owners and entrepreneurs learn how to sell more of their products and services online, which I needed in previous ventures. I wanted to teach the lessons I had learned the hard way.

Ace and I cofounded a digital marketing company called Laptop Freedom in 2017. I created a profile on Upwork to generate interest, and my strategy was to undercut the market.

The first client I had this opportunity with was Brian Page, an online entrepreneur just starting out. I helped Brian create his overall marketing plan. We generated traffic by advertising on joint venture lists, sold $1 million in course revenue in 43 days, and finished the year with $7 million in sales.

Word traveled fast about Brian’s success

People asked if we could replicate this success for their offers, so we took on more clients, including Kevin Harrington and one of the realtors from Million Dollar Listing.

In 2019, we decided to do the same with our own products and services. I pivoted the digital marketing company from agency-style work to educational products. We started accounts on Facebook and Instagram, as well as an email list, which all have around 250,000 followers total and growing.

Our first digital product was completed in 2020. We created a launch campaign to bring it to market that utilized affiliates, joint venture partners, Facebook ads, and my current audience — and we generated $450,000 in revenue in a single weekend.

When I first started, it was chaotic, but now the business has infrastructure, processes, systems, and a road map

I’ve created systems so that I only work around 10 hours a week max, depending on the project. We hired an operations manager to run day-to-day operations.

We use customer relationship management software for front-end marketing and back-end client fulfillment, financial management software to pay employees and contractors, and operations software.

I use my income to invest in real estate and travel

I tried stocks but couldn’t stand the up-and-down volatility, and crypto wasn’t for me either. I understand real estate, and it works.

I found an operator — my business partner and I are the bank, and he handles the logistics. We invest in distressed residential properties, which we rehab and sell, and apartment complexes.

I also use the money I make to travel. My wife and I travel six months a year and then take a breather. We’ve been all around the world.

I’m glad I overcame the failures because my businesses helped me create a life of freedom.



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