How to Survive Your First Development

A 27-Year Maui Project, Septic Setbacks, and Real Estate Wisdom from Both Sides of the Border What do you do when a condo development takes nearly three decades to complete? If you're Dr. Jennifer Salisbury—real estate investor, educator, and ex-Navy Nuclear Propulsion Engineer—you grit your teeth, pivot with purpose, and document every lesson along the way. From her multi-year condo build in South Maui to launching a 48-pad tiny home development in Canada, Dr. Jen shares unfiltered insights into the real costs of development, the assumptions that kill deals, and the mindset needed to survive—and thrive—in the world of real estate. Whether it's negotiating with contractors, walking into City Hall, or learning to “be comfortable being uncomfortable,” this episode offers practical gold for developers at any level. Guest Bio Dr. Jennifer Salisbury, known as Dr. Jen, is a former U.S. Navy Nuclear Propulsion Engineer turned international real estate investor and educator. With a Doctorate in Education, her passion lies in teaching through her podcast My Life As A Landlord. She leads real estate projects across the U.S. and Canada, where she applies her skills as an efficiency expert and small business champion to create housing-focused communities. Her recent Maui multifamily development tested every facet of her experience—especially when it wrapped just before the devastating wildfires. Today, she continues her mission of helping people understand real estate while leading with transparency, resilience, and hard-earned wisdom. Episode Highlights and Chapters 00:00 Align with mentors and watch your assumptions 00:31 Focus your energy—don't be a jack-of-all-trades 01:00 Development always comes with a cost—hire experts 01:14 Education is key: learn a little every day 01:36 The true currency is time 01:52 Eugene introduces Dr. Jen and her 27-year Maui journey 02:08 The burn-it-all-down moments—and why she didn’t 03:06 Building eight fourplexes in South Maui during COVID 04:33 Why tracking progress was more important than IRR 05:14 Managing 60+ partners via weekly update emails 06:08 Weather, delays, and realities of building in Hawaii 07:27 Financing her latest affordable housing project in Canada 08:11 The septic tank dilemma and being 10 feet too close 09:00 How bad assumptions sabotage development 11:00 Oversupply and checking your pro forma projections 12:30 Why you can't model deals based on future appreciation 14:00 Developers pay either way—choose your pain 16:00 Who pays when something goes wrong? 18:00 Real example: Survey creep and septic tank relocation 19:35 The cost of catching mistakes late in the process 21:00 When an inspector finds a problem at final inspection 22:11 Why Eugene stopped running his own construction company 23:16 The value of a strong team and why motivation matters 24:16 Navigating regulatory layers in Canada and the U.S. 27:00 How Dr. Jen got a green light without a permit 28:14 14 tiny homes ready to deploy—but no land 30:00 How to start: city hall, insurance, and then the bank 31:30 Municipalities rarely reject—they just delay 32:00 Insider tip: meet your planner during counter hours 33:00 Free advice vs. paid consultation 34:00 Educate yourself—every single day 35:07 Dr. Jen's personal definition of success 35:56 Where to find and connect with Dr. Jen Contact Information Dr. Jen can be found at her website mylifeasalandlord.com and on all major podcast platforms and social media channels under the name My Life As A Landlord. She also shares content about her real estate ventures and life on her boat via YouTube. Connect with the host, Eugene Gershman, at https://giscompanies.co/podcast/