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Writer's pictureJohn Lim

MF 181 : Moving Forward from Blue Collar Worker to Entrepreneur, with Jonathan Rivera

Updated: Jun 17, 2022


Moving Forward is also available on Apple Podcasts, Stitcher Radio, Google Podcasts, Spotify, and Amazon Music.


Jonathan Rivera is a blue collar worker turned real estate entrepreneur. Today, Jonathan will share how he is moving forward in business and why the smart goal is to work less.


Successes at a glance:

  1. Entrepreneur in real estate.

  2. Founder of The Podcast Factory.

Jonathan’s story:

Jonathan started out in the blue collar world. From childhood, he was raised and taught the “programming” of learning a trade, having something to fall back on. This led him to become an electrician which he did for 9 years and as Jonathan candidly shares he “hated” every minute of it. Jonathan did good work, moved up the ranks and by age 23 he was running jobs. But his heart wasn’t in it. Underlying this discomfort was that Jonathan felt there was more to the world and that he had more to offer than what he was doing. Jonathan started exploring real estate, seeing it as a way to break free of the rat race. Jonathan read a lot of books and dreamt about it for a couple of years. It wasn’t until Jonathan’s mom passed away that he decided to make a change. It was that loss that caused Jonathan to reflect on his life. He saw that his parents struggled throughout their lives and Jonathan realized that when his mom passed away, his parents still had bills and a mortgage. Jonathan took that as a cautionary sign not to live the same way. Jonathan left his job with $500 and got his real estate license. He made it work, even though it wasn’t easy. Jonathan didn’t do the side hustle route. He made a clean break. As he reveals on this episode, he had to. He was depressed and his work as an electrician was suffering as a result. Jonathan had to move in with his dad in the very beginning as cash was tight and he was just getting started. However, Jonathan’s timing was fortuitous. He started in real estate in 2004 while the market was still booming. Within a month, he was already closing deals and making way more money than he would have at his former job. But in 2008, things came tumbling down, causing him to feel some major doubts about his decisions up to that point. Jonathan hit such a low point that it took almost two years to climb back out of it. Throughout, what kept Jonathan going was that he couldn’t go back to his prior life as an employee. Jonathan made some big changes. Prior to this, Jonathan took a hands-on approach, doing a lot of the construction. He describes this as spending too much time “in the business” as opposed to “on the business.” He shares three big lessons: 1) he had to be the leader, the steward of the business, 2) he had to put money away for the rainy days, and 3) he had to understand where the business comes from and really understand the metrics and marketing.


Jonathan’s big why:

Today, Jonathan is still in real estate and has expanded to podcasting. During the downswing, Jonathan discovered podcasts, having already been a consumer of audio books. He dived into shows on marketing and entrepreneurship, finding both content and inspiration. Jonathan used this information to help him become a better marketer for his business but also discovered an entirely new niche of audio content.


Biggest challenge today

Jonathan’s goal is to do less. This may sound counter-intuitive but as he shares, being busy does not always translate to success. Thus, the challenge is to maximize your efforts in the right places so you are doing less to achieve more. This means being comfortable with a mindset that runs completely counter to the programming that most us of are used to.


Moving forward past that challenge:

Jonathan tracks his time down to the minute, to see where he’s wasting time and where he could be delegating tasks. By auditing his time, Jonathan is making sure he has enough allocated to personal development, creating assets and the important priorities.


Knowledge bursts:

  1. Time management app:

    1. Toggl

  2. One thing that Jonathan does that runs counter to what most people say is the right thing to do:

    1. Work 20 hours a week (his “do less” mantra). Jonathan is trying to get it down to 15 so he can allocate more time over several businesses.

  3. Best gift for under $30:

    1. The BestSelf Journal: elegant, simple, and keeps him accountable.

  4. How is Jonathan moving forward today:

    1. Reading 10 pages of a biography a day – currently, Titan: The Life of John D. Rockefeller, Sr.

Support the Podcast:

  1. The Corporate Cliches Adult Coloring Book: makes the perfect stocking stuffer or white elephant gift.

  2. Try out Audible (affiliate link).

  3. Try out Amazon Prime (affiliate link).

Who is Jonathan in five years:

For Jonathan, the future is about maximizing quality time with his wife and son. To facilitate this, he plans to live a life where his businesses are automated as much as possible so that he is working 4 days a week with significant passive income streams. Part of this vision includes a $3M condo overlooking a mountain where they spend at least 3 months of the year enjoying the ski slopes. Jonathan’s vision is about having the financial freedom to enjoy life with his family.


Parting wisdom:

“Do work.”


Connect with Jonathan:

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