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.

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For a deeper dive into these insights and more, be sure to listen to the full episode of the Onward podcast.

Have questions or feedback about this episode? Drop us a note at [email protected]. 

Onward is hosted by Ben Miller, co-founder and CEO of Fundrise. Podcast production by The Podcast Consultant. Music by Seaplane Armada. 

About Fundrise 

With over 2 million users, Fundrise is America's largest direct-to-investor alternative asset investment platform. Since 2012, our mission has been to build a better financial system by empowering the individual. We make it easier and more efficient than ever for anyone to invest in institutional-quality private alternative assets — all at the touch of a button. 

Please see fundrise.com/oc for more information on all of the Fundrise-sponsored investment funds and products, including each fund’s offering document(s). 

Want to see the specific assets that make up and power Fundrise portfolios? Check out our active and past projects at www.fundrise.com/assets.