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Ready to leave entrepreneurship or another field behind and jump into a stable tech career? In this episode of the Hacker Proof HQ Podcast, host Daniel sits down with Juwon “The Techie” Isola‑Osobu, a Senior Product & Solution Design Manager who has helped more than 1 000 students land their first roles in tech juwonthetechie.com.
Juwon explains why he chose to quit entrepreneurship, how he built a successful career in tech and the strategies he recommends for beginners — including those with zero experience. You’ll hear about the biggest challenges newcomers face (like imposter syndrome and lack of mentors) and how to overcome them, plus tips on building your personal brand and networking strategically.
Key Takeaways:
– Practical steps to get into tech when you’re starting from scratch.
– Real talk on obstacles (fast‑changing tools, job‑search fatigue) and how to stay motivated.
– Why personal branding and community make a huge difference in your career journey.
– Insights from Juwon’s training program, which has supported over 1 000 aspiring technologists juwonthetechie.com.
Timestamps:
0:00 – Intro & Juwon’s background
3:20 – Why he left entrepreneurship
7:45 – First steps to break into tech
15:10 – Challenges & how to overcome them
24:00 – Building your brand & networking
31:00 – Closing thoughts & resources
Like what you hear? Subscribe to Hacker Proof HQ on RedCircle (or your favorite podcast app) for weekly episodes on tech careers, cloud security, cybersecurity and DevSecOps. Join our newsletter at hackerproofhq.com for free resources and job tips. Follow us on Instagram and TikTok @hackerproofhq for daily insights, and feel free to rate and review the show—your feedback helps others discover it!
By Hacker Proof HQReady to leave entrepreneurship or another field behind and jump into a stable tech career? In this episode of the Hacker Proof HQ Podcast, host Daniel sits down with Juwon “The Techie” Isola‑Osobu, a Senior Product & Solution Design Manager who has helped more than 1 000 students land their first roles in tech juwonthetechie.com.
Juwon explains why he chose to quit entrepreneurship, how he built a successful career in tech and the strategies he recommends for beginners — including those with zero experience. You’ll hear about the biggest challenges newcomers face (like imposter syndrome and lack of mentors) and how to overcome them, plus tips on building your personal brand and networking strategically.
Key Takeaways:
– Practical steps to get into tech when you’re starting from scratch.
– Real talk on obstacles (fast‑changing tools, job‑search fatigue) and how to stay motivated.
– Why personal branding and community make a huge difference in your career journey.
– Insights from Juwon’s training program, which has supported over 1 000 aspiring technologists juwonthetechie.com.
Timestamps:
0:00 – Intro & Juwon’s background
3:20 – Why he left entrepreneurship
7:45 – First steps to break into tech
15:10 – Challenges & how to overcome them
24:00 – Building your brand & networking
31:00 – Closing thoughts & resources
Like what you hear? Subscribe to Hacker Proof HQ on RedCircle (or your favorite podcast app) for weekly episodes on tech careers, cloud security, cybersecurity and DevSecOps. Join our newsletter at hackerproofhq.com for free resources and job tips. Follow us on Instagram and TikTok @hackerproofhq for daily insights, and feel free to rate and review the show—your feedback helps others discover it!