How Habits Determine Your Success, with Jeff Winkler

By Published On: July 31, 2018Categories: Blog, Podcasts, The CTO Studio

How habits determine your success is something our guest for today knows firsthand! Jeff Winkler is the co-founder of Origin Code Academy, an organization that helps students get the skills they need to start and succeed in software development.

On today’s show we begin by talking about good habits, bad habits and affirmations. Specifically we dig into which books are most helpful, and what Jeff does to persevere in the face of the many challenges of an entrepreneur’s daily life. Join us to dive into those topics and more on today’s CTO Studio!

In this episode you’ll hear:


  • Why do you need to allow yourself to fail?
  • What do good habits get you more of?
  • Does anything happen right away?
  • What is Jeff’s personal affirmation?
  • Why must a C level leader be pathologically optimistic?
  • And so much more!

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As the leader of Origin Code Academy, one of the things Jeff talks to his students about is how successful habits are at the core of everything you do. If you boil it down to the simplest thing you just need to look at one area and answer these questions: What are your daily habits? What is the outcome you are going to reach tomorrow, next year, 5 years and even 10 years from now based on those habits? Your answer will show you if you’re on the right track or if you need to make changes.

And Jeff does this personally; he decided to challenge himself by getting up at 4:30am! He knew he had to do it for a month. So that’s what he did. He’s now made it a daily habit for the last six weeks. As a result his Inbox has consistently been at zero at the end of each week and he’s consistently had a plan for each day.

But that doesn’t mean he’s perfect. In his own life and in the classroom he knows perfection isn’t possible, but daily progress is and that is what the goal should be everyone.

In fact, when he fails at something he gives himself 15 minutes to be upset with himself and then he moves on with his day reciting his own personal mantra: as long as you don’t give up you will win.

Next we jump into the start of the Origin Code Academy. I asked Jeff what sets this organization apart from the others out there, and Jeff takes us back to the start of the company. He had started an app previously with a developer he found on Craigslist; they sold that to Class Pass. He knew he didn’t want to give up ownership in his next company if he had to and he felt like he could raise money if he built an MVP with revenue or user traction. But to get a prototype built would cost between $10k and $20k.

At the same time coding boot camps had recently come out, they were about a year old. So he decided to pay $12k to teach himself how to code and then he could build the MVP himself. It didn’t have to be a great MVP, it just had to be good so he joined a class. Everyone else in his class was there to change jobs or careers, he was the only one there to start a company.

Afterwards no one in his class could get a job and they were all pretty upset. As a naturally curious person he decided to go on a job interview. During the interview they asked him to take a code test, something he didn’t know was part of the process!

During the interview he also explained his biz dev experience and was talking to one of the investors. That person asked him what he was up to next and Jeff was telling him about how everyone in his coding class wasn’t able to get a job. The investor suggested he work on fixing that problem because it sounded like a problem Jeff was really upset about.

Initially Jeff was hesitant: schools are hard to scale. You have to get a building, train the proper teachers, etc. But after talking about it with the investor a bit more Jeff decided to do it. So Jeff came out to San Diego; there was no competition out here at the time so he went to a few co-working spaces to talk to people about whether there was a need for developers in San Diego.

James Martin from Co-Merge was someone he spoke with and James told Jeff there was a definite need for more developers in the area. After that Jeff negotiated for one classroom and took it from there. Three years later they are going strong and have helped over 105 people get jobs in San Diego.

The only students who haven’t gotten jobs are the ones who don’t return his calls and/or don’t show up for their meetings. Jeff fully supports all of his graduates during their job search process. His dedication and commitment are why at least 80% of his academy graduates are now employed as developers.

Which led me to ask if he’s found it’s more about soft skills today than coding curriculum? Jeff says that has always been the case, they are just more aware of it now.

He gives an example from the last 30 days: there’s an employer in Encinitas that just hired one of their students. Two weeks after hiring this student the employer was back to attend a job fair. Jeff asked how the student was doing and the employer said the student is the best because the student never bothers him!

All of his other employees will come to him with questions without exhausting all potential avenues, but when the student from Origin Code Academy comes to the employee with a question the employer knows the student has tried everything under the sun to solve the problem first.

That student has created a successful habit of looking for answers on his own, a habit he did not have before joining Jeff’s academy.

Also on this episode of CTO Studio, Jeff tells us the top objections he hears from CTOs about bringing in code school graduates, and why you as a CTO needs to have a talent pipeline for senior engineers.

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