Ep019: Esther Dyson on Asking the Difficult Questions

By February 21, 2017Podcast

Esther Dyson is perhaps one of the most coveted investors of our time….Not only does she have an impeccable track record (including investments in MeetUp, Evernote, Square, 23andMe, LinkedIn, Facebook, Startup Health, HealthLoop, Patients Like Me, and dozens of others), but her insatiable thirst to explore the impossible and the undiscovered makes her un-matched in her ability to identify opportunity where others do not. On this episode, we get into the mind of Esther’s core investment philosophy, explore the influences of her upbringing, and discuss her quest to make health profitable through her latest venture, Way to Wellville. We discuss why asking the right questions is key to solving the mysteries of business, why our health system is so broken, and what we can do to help course correct an industry that has repeatedly failed us.

All this and more on today’s episode. Now, That’s Unusual.

About Esther Dyson

Esther Dyson is a Swiss-born American journalist, author, businesswoman, investor, commentator and philanthropist. She is a prominent angel investor focused on breakthrough startups in healthcare, government transparency, digital technology, biotechnology, and space.

Esther Dyson is currently focusing her career on health as the Executive Founder of WaytoWellville, an initiative focused on investing in health as an asset. The goal is to build networks through community organizing to increase access to and use of beneficial services, activities and resources to improve the health of residents in five model communities. Ultimately, Dyson hopes to utilize big data to demonstrate the economic value of investing in health and affect large scale change.

After graduating from Harvard with a BA in economics, Dyson began her career as a fact-checker for Forbes before heading to Wall Street where she worked as an analyst. This led to a partnership with Ben Rosen in the emerging personal computer and online world. She bought Rosen Research in 1983 and renamed it EDventure Holdings. After 25 years with the company, Dyson sold it and pursued an interest in angel investing and health care.

Dyson is unmatched in her ability to identify opportunity where others do not, and she is currently on a mission to make health profitable.

Key Interview Takeaways

Ask good questions. Dyson credits her success to an ability to craft the right questions and listen to the answers with a truly open mind. She believes that her true education began after she finished college (where you learn about things people already know) and became a reporter, working to discover the things people didn’t already know.

We must shift our focus from health care to health. Dyson argues that health care is expensive and remedial, a function of chasing after our health once we’ve already lost it, whereas health is the capacity of the human body and mind to renew itself.

Zip code determines individual health more than any other factor. Too many Americans are born into an environment that destroys their health rather than building it. WaytoWellville seeks to transform the health ecosystem in five communities, providing a prototype to initiate large scale change.

To affect change, people must be accountable for making it happen. Dyson contends that much like building a physical bridge, building a community that is conducive to health requires standards, workers, a budget, deliverables, etc. Meaning well is not enough.

To overcome the challenge of personal accountability, peer groups must be led by members of their own community. A network of support at the neighborhood level is the only way to change behavior, thus WaytoWellville helps communities launch and run their own programs.

If we invested in health rather than health care, costs would go down. Dyson is working to make the economic case for investing in programs aimed at providing health coaches to help people understand how to take care of themselves and their children long before they need an expensive high-end practitioner.

Empower people to make the right decisions. We are currently influenced by advertising, the behavior of those around us, pricing and agricultural policies to make decisions that are not in our best interest or the best interest of our health. The public must be given the power to manipulate themselves – to their own advantage.

Learn More About Esther Dyson




Antifragile: Things That Gain from Disorder by Nassim Nicholas Taleb

“The Heroism of Incremental Care” by Atul Gawande






To subscribe to the podcast, please use the links below

Click Here to Subscribe via iTunes

Click here to Subscribe via Stitcher (Android users)

If you like the show, please consider leaving the show a review in iTunes or Stitcher. A couple minutes of your time can help the show immensely! Thanks!

%d bloggers like this: