Working For A Dream

EP 16: Drew Laine — Finding Fulfillment As A Serial Entrepreneur


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Drew Laine is a serial entrepreneur who, in the past, has done his fair share of chasing after the next shiny thing. 

 

He’s started a wide variety of companies, from lead generation to insurance, software, printing, and, today, sports manufacturing. Some have been successes, some haven’t. He’s learned from them all. But perhaps his most impactful learning came out of his hockey company, the Penalty Box. 

 

Growing up “with a stick in his hand,” Drew has always been a major hockey fan. And when, through the Penalty Box, he came to see how local hockey communities were rallying around young hockey players in need and organizing for them on Facebook, he wanted to be a part of that. The Penalty Box Foundation started small, supplying a handful of kids with free hockey bags. When he was sent a video by a foster mom of one of her foster kids opening the bag with tears in his eyes, Drew knew the Foundation had already moved it way to the core of his purpose.

 

“Seeing the charity and the giving side of it gives me the basis to everything I do,” he says. “I’ll tell you, the fire I feel every day waking up knowing I’m making an impact on the sport that I love, on a community that I love, on the people that need it — it’s everything to me.”

 

In this episode of the Working For a Dream Podcast, Patrick and Drew talk about the “freedom to dream” that comes with entrepreneurship, what makes the hockey community so special, and the gift you get when you give back.

 

What You’ll Learn:

  • How an idea one couple-of-beers-deep night became The Penalty Box
  • How Drew has learned to combat the loneliness of entrepreneurship and find a community that gets it
  • The value of failing “so many d*** times”
  • And much more!

 

Favorite Quote:

“The feeling that you can make an impact through your hard work and really drive change is everything to me at this point. Other companies that I've had in the past, it was all, ‘Oh, this seems like a good idea.’ We go after it and there's no heart. There's no desire, there's no passion. I can't wake up in the morning and look myself in the eyes and see the fire and desire to get up and kick a** like you do when you get excited... it didn't feel like this, man.”

— Drew Laine

 

How to Get Involved:

Connect with Drew: 

DrewLaine.com

Instagram

Facebook

YouTube

 

Connect with Patrick: 

LinkedIn

Facebook

Instagram

...more
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Working For A DreamBy Patrick Bolanos

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