Get to Know GYST

We believe life happens and the idea of not being alive is so overwhelming, most of us put off making plans. At GYST, we help everyday busy people put end-of-life plans together one small step at a time from Advanced Care Directives to managing your Digital Life.

Our Story

Life goes sideways sometimes. When it did for GYST's Co-founders, we found ourselves overwhelmed and under prepared.

  • One of us lost her husband in an accident. She was left with no emergency savings, an unsigned will, and outdated insurance policies.
  • Another lost his mother, who was the primary caretaker for his paraplegic father. He was living out of state and had to immediately drop everything and navigate the elder care system. Ouch.
  • Another co-founder's father had a life-threatening accident outside the US. He had not made his wishes clear about what to do if he found himself in the ICU.

And as it turns out, we are in good company. More than half of the US adult population doesn't have an estate plan. Slightly less than half those age 40-59 find themselves caring for our aging parents and younger children. And most of us don't have savings to cover those what-if situations.

What's holding us all back?

  • 42% of us are overwhelmed by the information out there today
  • 35% don't know where to start
  • 31% simply get stuck

Our Team

Jessica Ostrow, CEO & Co-Founder at GYST Now, Inc.

Jessica Ostrow

CEO & Co-Founder

Jessica Ostrow is an entrepreneur that is laser focused on bringing a modern solution to market, helping consumers get results around the important plans in life, GYST. She brings over 20 years' experience in developing business strategies, consumer and business-to-business marketing, technology product management as well as managing operations and working across global markets. She has led marketing communications and advertising organizations for leading brands at Microsoft, POSSIBLE, a WPP agency, as well as provided strategic marketing consulting services to technology companies including Getty Images, The Bill & Melinda Gates Foundation and others mobile and technology companies. Her passion is consumer products and services.

Chanel Reynolds, Co-Founder & VP of Engagement and Community at GYST Now, Inc.

Chanel Reynolds

Co-Founder & VP of Engagement and Community

Chanel Reynolds is both a digital professional and an entrepreneur having founded She brings those experiences and her focus on stories and communities as a Co-Founder of GYST. Her site launched in 2013 and reached millions worldwide, inspiring people everywhere with her story and giving them the 'kick in the pants' they needed to take care of the basics. Her story and the site have been featured in in The New York Times, The Huffington Post, LifeHacker, BoingBoing, and on CBS, ABC, NPR, and Redbook magazine.

Previously, Chanel was an Interactive Strategist and Program Manager with leading creative agencies, producing digital experiences for clients such as Nike, Samsung, Microsoft, Tom's of Maine, and Starbucks. Her roots are in the arts and non-profit world as the founding Managing Director for, launching a contemporary arts center, and even spending a year as an international adventure travel guide.

Phil Shigo, Co-Founder & VP of Business Development at GYST Now, Inc.

Phil Shigo

Co-Founder & VP of Business Development

Phil Shigo is an entrepreneur who believes passionately in new ideas that show the potential to move the world forward. Prior to co-founding GYST, Phil was Managing Director at Creature, an independent creative agency with offices in Seattle and London. Phil spent over 15 years at Microsoft leading various efforts in product management, corporate marketing and business development was part of the co-founding team that developed Expedia.

Chip Cressman, Lead Engineer at GYST Now Inc.

Chip Cressman

Lead Engineer

Chip Cressman is a web technology enthusiast based in Seattle, WA. As principle of Cressman Consulting, he works with a variety of cutting-edge startups, providing development support, platform architecture and product management. He previously held roles at VML, Moby Inc., and Glympse, working on award winning projects for some of the world's largest brands, including XBOX, T-Mobile, Telus, Microsoft, Fluke Biomedical, and the WPP Group. Outside work, Chip pretends to be a professional cocktailian, an amateur photographer, a part time long boarder, but only if the sun is shining.

Joe Alterio, Design and UX Lead at GYST Now, Inc.

Joe Alterio

Design and UX Lead

Joe Alterio is a digital-native creative director, storyteller, and designer, who has been pushing the digital medium forward while creating engaging and useful experiences. He's spoken at SXSW, SIC, SDCC and other venues about online experiences.

Joe Shepter


Joe Shepter is a freelance journalist and ghostwriter, primarily serving global executives in a range of industries. His clients routinely appear in major publications like Forbes, Fast Company, Inc., The Huffington Post, and The Guardian; and their books have been accepted by major publishers, including Wiley and McGraw Hill. Joe is also a Cannes-winning advertising copywriter and has worked on projects for brands that include Coca-Cola, Microsoft, and AT&T.