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/