TLB 12: How To Retire At 38 By Starting And Selling A Startup, With Jake Desyllas

By Fumnanya Bernard | Uncategorized

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May 31


Fumnanya Bernard took quite a bit of an effort to get in touch with Jake due to the lifestyle he’s living right now. Today on “The Limit Breaker Show”, Fumnanya got Jake to share his work experiences and the reasons why he started and sold his business.

Listening to this episode of The Limit Breaker show is sure going to help crush those frustrating limits of working a job to starting your own business.

A Little Insight About Jake

Jake Desyllas wanted maximum freedom and the chance to spend every day doing only things that he loves. So far, he has published two books:“Becoming an Entrepreneur” and “Job Free” and now he is a perpetual traveler, a minimalist, he is playing in a band and also a podcaster.

Together with his wife, Jake is now travelling the world and living on different places.

Jake’s Experiences On His Consultancy Business

In 2000, Jake started a consultancy business specializing in pedestrian movement advising shopping center developers, retailers and property developers on how to make their buildings and centers better for pedestrian.

Take A Risk And Don’t Be Afraid To Face Criticism

Don’t hold yourself back because you’re worried on making mistakes and it would be embarrassing. People around you criticize you for your mistakes but we are strong enough to endure the embarrassment and learn from our mistakes. Failure is a sign that you are doing something. Jake’s advice is “Don’t let the fear of embarrassment hold you back and don’t let your fear prevent you from reaching your own potential”.


Do not be limited by the circumstances of your birth.

[2:39] Who is Jake Desyllas: Jake is an author, investor, entrepreneur and host on The Voluntary Life Podcast. He writes about entrepreneurship, financial independence and freedom.

[3:51] Jake’s story: As an entrepreneur, he started a consultancy specialized in pedestrian movement and flows in the year 2000 where he was enthusiastic about making the world better for pedestrians. He sold the consultancy in 2007 to a multinational engineering company and worked there as a director for three years after which he quit. Now he is enthusiastic about entrepreneurship and finding other ways of finding freedom.

[5:38] On Jake’s book called “Job Free” which is about different ways of achieving financial independence.

[6:39] How Jake came across the idea of having a life without having to work: As a teenager, he had a conversation with a man named Peter who had become successful in London’s financial sector after going through a difficult childhood. Jake learnt that you can change course in your life. After selling his business, Jake decided that there is a certain amount that you need to survive in life and that you do not need so much stuff to be happy in life.

[12:01] How Jake started and sold his company: He started his business after being involved in research involving simulation of pedestrian movement. After starting his business, he faced challenges namely, lack of entrepreneurial experience and having to re-orientate his mind to selling and what customers needed.

[16:51] How long it took for the business to be profitable: It took five years for Jake’s company to be profitable and along the way, he learnt some lessons such as the importance of spending money wisely when you take on a lot of investment early and having to scale and sustain the growth of a company.

[18:57] Starting a business is a learning experience and as an entrepreneur, you will have to address your limits. It makes you stronger and is key to survival as a business.

[19:55] What kept Jake motivated and his Why: He was genuinely passionate about making the world better for pedestrians and he believed in the mission of what he was doing. He had a genuine interest in how to make a difference. He found the business and its challenges rewarding and fulfilling.

[22:26] On having a vision: You have to inspire the people who work for you about the vision of the company. You have to be the chief enthusiasm inspirer.

[24:07] In his current lifestyle, Jake is most grateful for the freedom to be able to do what he chooses to do. Freedom is one of the key benefits of entrepreneurship.

[25:17] How Jake would rebuild everything if he lost it: Jake mentions the importance of resilience, understanding customers and selling and that he would focus on them. He also talks about the minimum viable product and says that he would have focused on it as well.

[26:58] What Jake would have advised those who are going to quit their job to focus on: Jake talked about his background in startups and how he built and sold a startup. He highlighted some of the other characteristics of startups and how they may not suit the personality of some people. There are other options available as well. He would advise people to look at the different ways they can quit and see which one suits their personality and preferences.

[28:56] Jake outlines four different roots to job freedom in his book, namely, extreme saving that focuses on saving more than 50% of your income, unjobbing that involves making money doing things that you really enjoy, lifestyle business that involves starting your own business doing what you want, and startup that involves creating a business that makes impact and has the opportunity to grow.

[34:38] On extreme saving and how it works: You have to learn how to save and invest your money and how to take a low cost approach. Jake mentions the kind of investment called passive investment that involves investing in a portfolio and allowing it to accumulate over time.

Getting to know Jake

[37:35] Jake’s personal mission statement: Finding freedom in an unfree world.

[38:08] Jake mentions places he has visited in the world, such as Latin America and Hong Kong

[39:12] On the advice Peter gave to Jake: Jake talks about having confidence. In the end, you have to take the leap into the unknown with entrepreneurship. Another piece of advice Jake talked about that reminds him of Peter is that by the time you reach some point in your life, it becomes your responsibility to make the circumstances of your birth irrelevant.

[41:48] Three people, living or dead, Jake would invite to dinner are Derek Silvers, author of the book “Anything You Want”, Richard Branson, and Steve Jobs and they would talk about business.

[42:50] Books that have helped Jake the most in life and business are “Getting Things Done” by David Allen, which is on organizing your productivity, “Getting to Yes” by Fisher and Ury on negotiation and “How I found Freedom in an Unfree World” by Harry Browne, which is on freedom in entrepreneurship and personal freedom.

[45:05] Tools and resources Jake uses that make his life easy online: Jake uses a task management application called OmniFocus for Mac and iOS to manage commitments, tasks and projects.

[46:09] Parting advice from Jake: If you want to take any of the entrepreneurship paths mentioned, you will have to take a risk. Don’t let the fear of embarrassment hold you back.

[48:21] Where to find Jake: You can find Jake on The Voluntary Life podcast and at

Mentioned on the show:

Anything You Want: 40 Lessons for a New Kind of Entrepreneur

Getting Things Done: The Art of Stress-Free Productivity

Getting To Yes

Job Free: Four Ways to Quit the Rat Race and Achieve Financial Freedom on Your T


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