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EP225Lessons from 20 Years of Building Businesses


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Brooke has been building businesses for 20 years, and she’s changed a lot over time. So, what advice would she give her younger self? Listen in as Brooke sits down with her husband Brett to reflect on 2 decades of entrepreneurship, sharing the good, the bad and the ugly of her journey to business success!

Question Highlights

  • When you compare who Brooke was 10 or 15 years ago to the current Brooke, what is the biggest difference in terms of how you approach business decisions?
  • Can you talk about the very first job you took at the mall when you were 15 years old? And some of the corporate jobs that you had before you decided to become an entrepreneur?
  • Going back to the original LLC that you started, 360 Your Life, what do you think was the biggest failure within that company? How did you grow that business? What did that journey mean to you? And what did it teach you the most?
  • When it comes to all of the things you have built over the past 8 years, what is your biggest personal or professional success?
  • What would the current Brooke tell the younger Brooke on a personal level? What would be your best piece of advice?
  • How does the current Brook measure success?
  • Over the last 20 years, I’ve watched you grow professionally, I’ve watched you grow spiritually, and I’ve watched you grow personally. What is the one thing that has not changed within you during your journey?
  • What did you love about the old Brooke that maybe the new Brooke has forgotten a little bit about?
  • What is the most important piece of advice that you would give your younger self about money?
  • If you were 10 times more bold, what would you be doing right now?

In this episode, you’ll learn about…

  • [3:10] How Brett supported Brooke through her entrepreneurial journey
  • [7:20] Why taking messy action is much better than no action at all
  • [9:33] Brooke’s experience doing jobs she wasn’t passionate about for money or status
  • [20:27] The hard question Brett asked Brooke when her first business was struggling that inspired the creation of Live Out Loud
  • [28:30] How Brooke’s goal to pay for her girls’ education kept her going on the bad days
  • [33:58] Brooke’s challenge to go ALL IN on what you’re called to do
  • [36:14] Measuring business success by the impact you make on others
  • [37:23] How Brooke’s commitment to being a champion for women has not changed over time
  • [41:50] Brooke’s advice on setting giving goals and investing in yourself
  • [44:47] Asking people in your network to introduce you to their communities
  • [46:58] Brett’s insight on leaving a corporate job to work with your spouse

Show Notes

Brooke has been building businesses for 20 years, and she’s grown and changed a lot in that time. So, what advice would Brooke give her younger self?

What mistakes did she make in her entrepreneurial journey? What is she most proud of? And what did she learn along the way?

On this episode of The Live Out Loud Show, Brooke sits down with her husband Brett to reflect on two decades of entrepreneurship, describing how her approach to making business decisions has changed and what meaningful goal kept her going on the most difficult days.

Brooke challenges us to go ALL IN on what we’re called to do and measure success not by money or status—but by the impact we have on others.

Listen in to understand how Brooke’s commitment to championing women has not changed in the last 20 years and get her best advice on setting giving goals and investing in YOURSELF.


Love Out Loud Foundation

5 Things I Wish I Knew When I Started My Business on The Live Out Loud Show EP171

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