Full interview · Real Estate & Investing

Jason Signor

Founder & CEO · Big Sky Funds

Jason Signor on civil engineering, healthcare real estate, entrepreneurship, resilience, team-building, and creating win-win outcomes through uncertainty.

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The story in brief

Jason Signor's path moved from environmental science to chemistry, civil engineering, hospital design, and ultimately healthcare real estate. He founded a business just before the 2008 financial crisis, grew it across development, investment, and senior living, then faced another defining disruption when COVID upended a major transaction and devastated senior-living operations. Rather than treating a career as a straight line, Signor treats it as a series of informed bets: narrow the focus when evidence points somewhere stronger, protect time to recover, and make sure the people around you can win too.

Inside the conversation

The moments that
shaped the path.

01

A changing academic map

Signor attended three high schools, completed advanced study through TAMS, and changed fields several times before graduating from Texas A&M in civil engineering. His first post-college move was not a conventional engineering job but a season at a Wyoming guest ranch, followed by a relationship-driven move to Nashville and work designing hospitals.

02

Finding the commercial side of healthcare

An MBA at SMU helped Signor combine engineering analysis with sales, finance, and entrepreneurship. Hospital planning led into medical real estate, where he founded and scaled a national platform spanning development, acquisitions, and senior living. The financial crisis arrived months after he started, forcing resilience into the company's operating model from the beginning.

03

Narrowing the focus after disruption

COVID interrupted a transformative transaction and put senior-living communities under extraordinary pressure. Signor eventually stepped away from the broader company and concentrated on the medical-office investment work that had been most consistently successful. In building Big Sky, he emphasizes adaptable thinking, rigorous hiring, delegation, follow-up, and outcomes where partners as well as the firm benefit.

Career map

How the path unfolded.

The route becomes clearer in retrospect. These are the decisions, detours, and discoveries that moved the story forward.

  1. High school

    Three schools and advanced study

    He finished at the Texas Academy of Mathematics and Science after exhausting the math courses available locally.

  2. College

    Civil engineering at Texas A&M

    Environmental science and chemistry eventually gave way to a degree that connected systems with the built environment.

  3. 1999

    Wyoming, Nashville, and hospital design

    A guest-ranch summer led to Tennessee, where he began designing and planning healthcare facilities.

  4. Graduate school

    MBA at SMU

    Business school helped him combine engineering discipline with finance, sales, and entrepreneurship.

  5. 2008

    Founds a healthcare real estate company

    He launched just before the financial crisis and learned to diversify, adapt, and survive difficult timing.

  6. Growth

    Develops a national platform

    The business expanded across medical offices, development, acquisitions, and roughly 25 senior-living communities.

  7. 2020

    COVID forces a reset

    A major transaction collapsed as the pandemic transformed senior living and the economics of the business.

  8. Today

    Builds Big Sky Funds

    He focuses capital and operating expertise across real estate investments with a sharpened emphasis on proven strengths.

Carry this forward

Five ideas worth keeping.

  1. 01

    You are allowed to change direction; a varied path can make you more capable, not less focused.

  2. 02

    When circumstances turn against you, preserve time, adapt the plan, and keep moving.

  3. 03

    The best long-term deals leave the other people involved feeling that they won too.

  4. 04

    Exceptional performers combine initiative with follow-up so other people never have to guess whether the work is done.

  5. 05

    Purpose and generosity can create a deeper measure of success than status or short-term happiness.

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