‘I don’t regret skipping 9-5 to build AI Agents’ with Chatforce CEO Robert Ciborowski
In this episode of The Time I Left My 9 to 5, we dive into the inspiring journey of Robert Ciborowski, CEO and co-founder of Chatforce. Skipping the traditional route, Robert transitioned directly from graduating from the University of Toronto to building his own startup. He shares his background, the challenges of founding a company, and the dynamic of working with three co-founders.Robert discusses Charforce's innovative approach to AI automation, their unique features, and the successful strategy that garnered early investor interest. He provides valuable advice for aspiring entrepreneurs on ambition, building the right team, and the importance of lifelong learning. This episode is a deep dive into the life of a young founder making waves in the AI-driven startup landscape.📲 Stay Up to Date with the Show:Host Instagram: https://www.instagram.com/maggieindataPodcast Instagram: https://www.instagram.com/thetimeileftmy9to5.podcastPodcast YouTube: https://www.youtube.com/@thetimeileftmy9to5.podcastChapters00:00 Highlight Overview01:20 Robert's Journey from University to Startup04:35 Early Coding and Game Development08:10 Building the Capstone Team12:39 Family Influence and Support17:13 The Six-Month Gray Area21:13 The Birth of Chatforce22:48 The Three Co-Founder Dynamic Revisited25:14 Empowering Knowledge Workers with AI Agents28:15 The Philosophy Behind Chatforce31:33 Getting Noticed by Investors39:50 Advice for Aspiring Entrepreneurs41:56 The Importance of Independent Learning43:59 Leveraging AI Tools and Resources53:09 Balancing Building and Learning Hosted on Acast. See acast.com/privacy for more information.
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How to Know When It's Time to Leave Your Job (7 Research-Backed Signs)
Welcome to the very first solo episode in the history of The Time I Left My 9 to 5 podcast! I asked on my Instagram what questions you had when it comes to considering leaving your 9 to 5, and I am answering all of them in this episode. I intentionally designed this episode to be research and statistics driven so that you can walk away with actionable frameworks that you can use to apply to your specific situation~What You'll Learn:✅ The Regret Minimization Framework - Jeff Bezos' decision-making tool for major life changes✅ Why 82% of businesses fail (and how to avoid becoming a statistic) ✅ The exact amount you should save before quitting (hint: it's more than 6 months) ✅ The "If-Then Planning" method that increases goal achievement by 300% ✅ How to stay accountable when you're your own boss ✅ The 10-10-10 Rule for making tough decisions✅ Why your nonprofit/teaching skills are actually gold in the corporate world📲 Stay Up to Date with the Show:Host Instagram: https://www.instagram.com/maggieindataPodcast Instagram: https://www.instagram.com/thetimeileftmy9to5.podcastPodcast YouTube: https://www.youtube.com/@thetimeileftmy9to5.podcast00:00 - Introduction 02:15 - "How do you report to yourself?" 03:35 - If-Then Planning Method 05:45 - "How did you know it was time?" 06:10 - Regret Minimization Framework 07:30 - The 10-10-10 Rule 10:25 - "How much money should I save?" 12:00 - Ramen Profitability Calculation 12:40 - "How to test a career pivot?" 13:50 - 4 Ways to Test Drive 15:25 - "Pivoting from nonprofit?" 17:20 - "Leaving a permanent teaching job?" 18:20 - Loss Aversion Psychology 19:25 - Get your answers answered Hosted on Acast. See acast.com/privacy for more information.
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C-Suite to Serenity: Letting Go of Prestigious Titles with Jenn Bieri
In this episode, Jenn, a former global head of business operations, discusses her challenging transition to becoming a yoga teacher and later a professional coach. She opens up about the identity shift, financial concerns, and personal growth she experienced during this transformative period. Jen shares insights into how she balanced multiple ambitions, navigated significant life changes, and ultimately found a fulfilling career in coaching and leadership development. Her journey underlines the importance of self-discovery, support systems, and continuous learning in achieving career fulfillment.📲 Stay Up to Date with the Show:Host Instagram: https://www.instagram.com/maggieindataPodcast Instagram: https://www.instagram.com/thetimeileftmy9to5.podcastPodcast YouTube: https://www.youtube.com/@thetimeileftmy9to5.podcast00:00 Introduction and Identity Shift02:14 Journey from Accounting to Tech03:18 Starting a YouTube Channel04:01 Transition to Full-Time Yoga and Coaching12:24 Navigating Financial Stability17:30 Coping with Identity Shift21:14 Building a Coaching Business30:14 Future Plans and Advice Hosted on Acast. See acast.com/privacy for more information.
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Why Discipline Doesn’t Work: Janis Ozolins on the Process of Elimination and Experimentation
Ever felt stuck in a job that doesn’t excite you? Or maybe you’ve spent months—even years—chasing a side hustle with no results? Janis Ozolins knows exactly how that feels. For four years, he tried everything—YouTube, blogging, podcasting—with zero measurable success. No audience. No money. Just relentless trial and error.But he never gave up. In this episode The Time I Left My 9 to 5 podcast, we dive into:How he stayed motivated when nothing was working (hint: it wasn’t just discipline).The exact moment he realized he was living in a bubble—and how a single book shattered his limiting beliefs.Why his first "successful" business model wasn’t sustainable—and how he finally found the sweet spot between passion and profit.The financial rollercoaster of entrepreneurship—how he planned his escape from the 9-5 (with a pregnant wife and a mortgage).The biggest mistake he made while building his side hustle (spoiler: it involves switching jobs at the worst possible time).If you’ve ever doubted whether you’re cut out for entrepreneurship, or if you’re tired of grinding with no results, this episode is for you. 📲 Connect with Janis:Instagram: https://www.instagram.com/jaozolins📲 Stay Up to Date with the Show:Host Instagram: https://www.instagram.com/maggieindataPodcast Instagram: https://www.instagram.com/thetimeileftmy9to5.podcastPodcast YouTube: https://www.youtube.com/@thetimeileftmy9to5.podcast00:00 Intro01:29 The Journey Begins: From Corporate to Creative04:37 The Struggles and Persistence10:01 Discovering the Visuals Niche18:45 Making the Leap: Quitting the 9 to 522:58 Financial Realities and Creative Freedom26:43 Staying Relevant in Content Creation31:32 Advice for Aspiring Entrepreneurs Hosted on Acast. See acast.com/privacy for more information.
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'I Left Private Equity to Start a Yogurt Company': Kiki Couchman on Building in Public
In this episode of The Time I Left My 9 to 5, Kiki Couchman is a Stanford grad who left her job in private equity to build a yogurt company with her best friend. Kiki is the cofounder of Beny Yogurt, and I have to say, she's probably one of the coolest founders I've ever interviewed in the history of this podcast. Kiki's story is one of calculated risk-taking and determination, as she left behind a successful career in private equity to build a consumer product from scratch with no investment funding.What I love about Kiki's story is her unique approach to building a business. Kiki and her co-founder Elan chose to build their brand in public, sharing behind-the-scenes moments on social media, and has already gathered over 12,000 loyal customers before the brand has even launched. Her always-on launch strategy, combined with the fact that the company is 100% bootstrapped, has forced her and her cofounder to think carefully about each step and every decision. With her forward-thinking mindset, bias towards action, and bravery, Kiki’s commitment is driven by creating a product that truly makes a difference in people’s everyday lives.Without a doubt, Kiki is an inspiration to anyone looking to make a change.I’m super excited to share this conversation with you, what made Kiki decide to leave her 9 to 5 behind, and how she has navigated the challenges and opportunities of building a business from scratch. But before we jump in, I’d love if you could subscribe to the channel if you’re watching on YouTube or rate the podcast if you’re listening everywhere else. You have no idea how such a small action can help me to continue bringing you more unfiltered, real conversations just like this one.📲 Connect with Kiki:Instagram: @couchwoman📲 Stay Up to Date with the Show:Host Instagram: @maggieindataPodcast Instagram: @thetimeileftmy9to5.podcastPodcast YouTube: @thetimeileftmy9to5.podcast00:00 Introduction 02:53 Kiki's Journey from Private Equity to Entrepreneurship 04:21 Building Beny Yogurt: Challenges and Strategies 10:49 The Role of Social Media in Business Growth 17:58 Partnership Dynamics and Personal Growth 24:07 Financial Decisions and Bootstrapping 29:06 Advice for Aspiring Entrepreneurs Hosted on Acast. See acast.com/privacy for more information.
In an era where the internet and creator economy are reshaping careers, a traditional 9 to 5 is no longer the only way to make a living. This podcast explores the stories of people who’ve chosen unconventional career paths—be it entrepreneurship, freelancing, or content creation. Join us as we invite guests from diverse backgrounds to share their journeys, insights, and advice on building fulfilling, nontraditional careers. Hosted on Acast. See acast.com/privacy for more information.
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