Scott Plank — who helped build Under Armour from the ground up, was the largest angel investor in WeWork, and is a seed investor in Fundrise — joins us to share what it really feels like to bet everything, lose big, win bigger, and keep moving forward.
In this conversation, Scott traces his path from building homes as a carpenter and selling bracelets in Guatemala to helping Under Armour grow from a family startup into a billion-dollar public company. He explains the financing strategies that kept the company alive in its early days, the lessons of scaling operations under intense pressure, and why he believes Under Armour couldn’t be founded the way they did in today’s world.
Scott also shares his experience as the largest angel investor in WeWork, unpacking why he saw value where others didn’t, and how he navigated both the spectacular rise and fall of the company. Along the way, he reflects on risk — when to push all in, when to shut things down, and how entrepreneurship is often about knowing when the world has changed.
Finally, he discusses his ongoing work in real estate and technology, including data centers and community development, and offers advice for the next generation of entrepreneurs. For Scott, the throughline is clear: success depends not just on grit, but on aligning values, timing, and the willingness to evolve when circumstances demand it.
- Listen on Apple Podcasts >>
- Listen on Spotify >> (or wherever you get your podcasts)
- Read a transcript >>*
