Why watching scrappy people crush it will never get old

I showed up late to the podcast game. Last summer, my cousin started talking about this podcast called How I Built This while we straddled dry-rotting green rafts at our family’s lake house in North Carolina, keeping those feet moving to fend off the mole-biting sunfish. (Where are you sweet summer?)

So I started listening to the podcast on my four-hour drive back to Maryland, thanks to the help of a tape adapter hooked up to my iPhone that’s so dysfunctional I must prop it up at exactly the right angle for it to even consider playing. And that’s when my obsession began, right there with all the truckers and mini vans cruising down Route 95.

What is it about these scrappy successful people who dive head first into their entrepreneurial drive and crazy ideas that gets me so fired up, motivated, inspired?


Spanx. LARABAR. Kate Spade. Framebridge. Instagram. Starbucks. Barre3. Airbnb. TOMS. WeWork.

The recipe did not exist. The product was not invented. The community was not there. The concept was unfathomable.

Recognizing a hole in the market means they stood completely alone with just their crazy idea to keep them company. Nothing existed, but they had a vision for that beautiful accomplishment and they invented the blueprints to build the successful empire. They were smart enough to learn on their own and ask questions, bold enough to max out credit cards and ask for wild investments, and confident enough to run hard and fast after an idea for building a brand with a blank canvas.

Me? I look at construction zones and just see a mess. (It’s why I wrote this post to remind myself that it takes time to build.) I just see the porta potties, but I want the vision for the final beautiful structure in the future.


The idea for Instagram came from a comment from Kevin Systrom’s wife Nicole while they walked on the beach in Mexico. She encouraged him with the idea to focus on photos. And she threw in her two cents to add filters to the app to build this idea for people to feel like their photos are worthy of sharing.

Pride stops us from wanting to thank someone we love for a great idea that leads to an accomplishment. I write off my mom’s ideas all the time (and then write essays about how she was actually right all along).

I’m not much of a planner. I’m a dreamer. Sure, I have a Google calendar and a paper planner, but I go in and out of writing and rewriting how I really should finally get my blood work done. I make lists on post-its and then shove them in random pockets and they get all wrinkled until I drop it in the parking lot at the grocery store. But I’m faithful to my poetic dreaming in my journal, my shouts that look like scribbles every morning as I listen to the dripping coffee.

We need all of us for success – the planners and the dreamers, the thinkers and the implementers, the timid and the fearless.


We all have a few friends who want to launch rockets to the moon, and then a few friends who want to throw a pity party requiring mandatory attendance for anyone within an arm’s length.

I had a conversation with a coworker the other day about how to tell a friend when she’s stuck in the Debbie-downer role and she refuses to ever act as the uplifting friend. (Conclusion: We don’t know how to break the news.) We sink into these designated roles and then seem too afraid to reverse it or shock people by showing up out of the blue to cheer them on with colorful signs on the sidelines.

What about these scrappy successful people? Maybe they aren’t the uplifting spirited friend, but they know how to invite the ambitious motivators who persevere through deep mud, slogging through a sloppy mess as if it was clean and polished all along.

I think it’s all contagious, if we allow ourselves to catch the bug. Even if it’s just the boost you needed to be successful in your ordinary day, to make your bed and get dressed and show up to work.


The host, Guy Raz, loves to ask the same question on every interview: “How much of your success was because of luck?”

Call it luck, or purpose, or fate. I’m on board with the CEOs and founders who believe it’s about what we do with what we’re given.

You’re standing right now in a moment in time. You have choices to make. (Cue the age-old fork in the road metaphor.) You get a spark, a little nudge that stirs inside of you.

What will you do with it? Will you start running with your spark, your passions, your crazy ideas, working morning and night to make sense of your cloudy dreams?

Will you notice the people weaving into your life, put there for a reason to connect you or motivate you?


These scrappy successful people take themselves seriously. They take their dreams seriously. And when they fail along the way? It’s messy and beautiful.


One response to “Why watching scrappy people crush it will never get old”

  1. […] like Joseph have long fascinated me. It’s why I write posts about how watching scrappy people crush it will never get old, or how it takes time to build (which I never like to relearn), or how to cancel your pity party. […]

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