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Sasha Tripp

Meet Sasha Tripp, the real estate entrepreneur who turned a $700,000 home-building disaster into her greatest testimony of resilience and growth.

Real Estate
Charlottesville, Virginia
Story House Real Estate

Sasha Tripp’s journey from a religious studies major to a successful real estate entrepreneur was anything but linear, yet it led her to create Story House Real Estate in Charlottesville, VA, while also coaching and training real estate professionals nationwide. Over her five-plus years with Strategic Coach®, she has experienced tremendous transformation, but it was during her darkest entrepreneurial moment—a home-building disaster that resulted in $700,000 in unexpected liens—that Strategic Coach’s principles proved most valuable.

“Every single important business decision I’ve made has been supported by Strategic Coach. During the worst crisis of my life, it gave me the community, tools, and energy management I needed to not just survive, but have our best year in business ever.”

- Sasha Tripp

Member since 2019

Coached By: Chad Johnson
Workshop Location: Chicago

The Entrepreneurial Awakening

As a religious studies major graduating in 2005 into a market recession, Sasha found herself with “no marketable skills.” Realizing she needed to either upgrade her skills or enter sales, she chose real estate for its low barrier to entry, and immediately faced the worst real estate recession in years.

But something clicked. “For the level of work ethic that I had, the sky was the limit in real estate, and I enjoyed working for myself.” After surviving those early years and launching Story House Real Estate, Sasha was riding high—until disaster struck. When her trusted builder went bankrupt mid-construction, she faced $700,000 in liens for work that had already been paid for. “Before Strategic Coach, I would mull over adversity a little longer. I’d get paralyzed.”

Crisis As The Ultimate Test

Sasha faced “the hardest thing I’ve experienced in my life.” The house cost had doubled, required extensive work, and forced her and her husband to become general contractors on a 10,000-square-foot property they never wanted, all while raising a one-year-old and running a business.

But instead of paralysis, Sasha found strength in her commitment and faith. “I committed to finishing that build and learning the skills that we were going to have to learn to get through it.” And the timing couldn’t have been better—COVID hit just as she was navigating this crisis, and Strategic Coach’s pivot to virtual workshops became a lifeline.

The workshops provided something invaluable: a community of unbiased people she could speak to in confidence without damaging her local reputation.

Most remarkably, during this three-and-a-half-year ordeal, her business had its best year ever.

Building The Future With Strategic Coach

The transformation in Sasha’s life over five years with Strategic Coach has been dramatic. “I was still getting out of a very ugly divorce. I was single. I wanted a child, but I was going through infertility. I had a brand-new company. A few short years later, I found the love of my life, got married, had a baby, and have a business that’s thriving.”

Strategic Coach gave her permission to stop holding herself back. “I think the biggest change for me is that I don’t feel like I have to play small anymore ... it gave me permission to just show up unapologetically.”

Now, Sasha is implementing a significant business model transformation after discovering her true 10x vision: coaching. “I’d rather train 10 of my agents to go sell a few houses each than sell 10 houses myself.” The Strategic Coach® Program continues to fuel her vision of 10x impact rather than just 10x revenue. “It’s going to be an exciting next five years.”

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