Have you ever faced a major career transition? How did you manage the challenges that came with it?

Glenn and Julie welcome Doug Motley, an accomplished real estate developer and the principal of Jackalingo Asset Management. Doug's journey from the banking sector to real estate development is nothing short of inspirational.

Growing up in Delaware, Doug has always been surrounded by a close-knit community, which played a role in shaping his career and entrepreneurial spirit.

Doug shares his appreciation for the changing seasons and how they reflect the ebb and flow of energy in local communities—transforming winter doldrums into the bustling vibrancy of summer.

He discusses his transition from a large banking institution to a smaller, more intimate real estate firm, where he taught himself financial modeling and rapidly rose to the position of CFO.

Throughout the episode, Doug emphasizes the importance of agility, persistence, and community-oriented projects. From launching JLAM in 2011 to his upcoming innovative retail center project, Doug demonstrates his commitment to creating spaces that benefit both investors and local residents.

The conversation touches on his unique ability to blend analytical skills with creative problem-solving, making complex real estate concepts accessible and engaging.

Empowering Moments

00:00 Delaware: Tight-knit community with easy accessibility.

05:54 Shift in work culture prompted career reevaluation.

09:01 Chose between expensive colleges; opted for scholarship.

11:10 Ignored Cornell summer program for beach summer.

13:44 Option for summer internship led to job opportunities.

19:41 Dewey Beach evolved into a year-round destination.

22:00 Each season here offers unique experiences.

24:16 Transitioned to small company, learned real estate development.

29:56 Determined not to waste potential observed in others.

32:11 Unbelievable timing, challenging, but educational finance experience.

36:38 Business partners decide to scale by delegating tasks.

40:33 Past ventures caused significant mental distraction and anxiety.

42:56 Exciting walkable retail center with restaurants, parks.

48:35 Improving everything I touch for community pride.

49:25 You always strive to improve, endlessly.

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Empowering Takeaways

**Seasonal Energy Dynamics:** - Doug Motley appreciates how different seasons bring distinct energy levels and activities, impacting both individual motivation and business operations.

**Career Transition & Adaptation:** - Doug's shift from a rigid corporate banking environment to a more casual, entrepreneurial real estate setting highlights the ability to adapt to different professional cultures and thrive.

**Community-Centric Real Estate:** - Doug emphasizes developing real estate projects that benefit the community, focusing on integrating transportation links and enriching undersupplied commercial areas.

**Self-Taught Expertise:** - Faced with a lack of immediate supervision, Doug self-taught financial modeling and planning, proving the importance of self-initiative in skill acquisition and career advancement.

**Persistence Against Failure:** - Doug’s approach to viewing failure as iterative learning rather than a dead end underscores the significance of persistence and adaptive learning in entrepreneurship.

**Mentorship & Support:** - Doug credits much of his success to mentors and champions who saw potential in him, highlighting the value of support networks in entrepreneurial journeys.

**Long-Term Community Impact:** - Doug's end game focuses on leaving lasting positive impacts on communities and projects, prioritizing sustainable and beneficial development over immediate financial gains.

**Balanced Perspective on Success and Failure:** - Doug’s reflections reveal a balanced view of success and failure, marked by continuous learning, adaptation, and a proactive approach to seizing opportunities and overcoming challenges.

Running a business doesn’t have to run your life.

Without a business partner who holds you accountable, it’s easy to be so busy ‘doing’ business that you don’t have the right strategy to grow your business.

Stop letting your business run you. At Harper & Co CPA Plus, we know that you want to be empowered to build the lifestyle you envision. In order to do that you need a clear path to follow for success

Our clients enjoy a proactive partnership with us. Schedule a consultation with us today.

Download our free guide - Entrepreneurial Success Formula: How to Avoid Managing Your Business From Your Bank Account.

Copyright 2025 Glenn Harper

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