We’ve officially hit 100 episodes of Own the Exit! In this milestone conversation, Caleb and Aaron reflect on the lessons learned from two years of weekly episodes, highlight unforgettable guest moments, and—for the first time ever—answer the same Exit Round questions they’ve asked every guest.

From how to build with the end in mind, to why your business shouldn’t become your prison, to the importance of stacking skills and planning your freedom, this episode is a candid and inspiring look behind the scenes of the journey so far.

TAKEAWAYS

• How and why Own the Exit was created
• The biggest lessons learned from the incredible guests hosted on the show
• Why most entrepreneurs accidentally build a cage instead of freedom
• The myth of “selling your soul” to your business
• The five Exit Round questions every entrepreneur should ask themselves

FOLLOWS

⁠Oak IQ Investments⁠

⁠Own The Exit⁠

⁠Aaron Investing⁠

⁠Caleb Investing⁠

CHAPTERS

00:00 Celebrating 100 episodes of Own the Exit

01:08 Why we started this podcast

02:33 The theme of building with the end in mind

04:15 What we learned from 100 guests

06:31 The winding, non-linear entrepreneurial journey

07:56 The most powerful guest lessons

09:16 Why your business shouldn’t be your prison

11:06 Answering The Exit Round for the first time

18:06 What we’d tell our younger selves

20:05 How we create freedom through business

23:18 Why you need a plan and an exit strategy

24:11 Thank you for 100 episodes!

KEYWORDS

entrepreneurship lessons from 100 episodes, how to build a business with the end in mind, business exit strategy planning, how to create financial freedom through business, time freedom for entrepreneurs, scaling a business sustainably, avoiding entrepreneurial burnout, business planning and goal setting, why most entrepreneurs fail to exit, how to make your business run without you, exit strategy for small business owners, building a sellable business, lessons from top entrepreneurs, creating passive income while scaling, avoiding the business owner trap

WANT TO LEARN MORE?

Join us on ⁠LinkedIn⁠, dive into our enriching content on ⁠YouTube⁠, and explore ⁠our website⁠ to discover how to secure your future through intelligent passive investments!

If you enjoyed the show, please LEAVE A 5-STAR REVIEW and SHARE this episode with someone who wants to build a stable future. Listen to all episodes on ⁠Spotify⁠, ⁠Apple Podcasts⁠, or any preferred podcast platform!