Linda Weston, Founder of Rapporto and former Exec. Director of Oregon Entrepreneurs Network

Linda Weston is former executive director of Oregon Entrepreneurs Network, and currently has her own business Rapporto helping entrepreneurs build their own businesses, whether by offering mentorship or helping them make valuable connections. As you might guess, she has accumulated a lot of wisdom to share. I hope you’ll enjoy our conversation!

Book Recommendation: The Underground Railroad by Colson Whitehead

Topics Discussed:

  1. Linda is drawn to areas where she can create opportunity, whether as a leader in a destination marketing organization, the start-up general manager for women’s professional basketball team in a league that was just starting, or executive director at Oregon Entrepreneur’s Network.
  2. She is currently at her own company, Rapporto where she works with entrepreneurs to get their businesses off the ground.
  3. She looks for clients who are passionate, coachable, and have the tools to be successful.
  4. What most successful entrepreneurs have in common. They manage risk well and are willing to take chances. They take feedback well and adjust. They are often brilliant. They think about things differently and see things differently from a lot of people. They are all in.
  5. “There really are a lot of them (entrepreneur’s) who do not color inside the lines”
  6. Most dangerous mistakes founders make: not being prepared before seeking outside investment, mistakes in hiring (in terms of not looking far enough into what the company will need in the future)
  7. Problems with failing to do enough research on a business idea before jumping in
  8. “Often, the best entrepreneurs have seen a problem in their own life.” And what that might look like
  9. How often can a company get paid in advance?
  10. The risk associated with getting paid ahead of when you deliver.
  11. Her own experience with bearing risk as the manager of her basketball team, at times writing personal checks for advertising on behalf of the organization.
  12. Are there lessons she thinks you can learn in entrepreneurship that you can’t learn in other businesses?
  13. Entrepreneurs born or made? She says born. They’ve always been this way.
  14. Non-founder factors that might make a business really successful, or unsuccessful.
  15. Big takeaway: Creating a team. You need a variety of talents, temperaments, and perspectives to have an organization that can handle all its needs well. Each person should be good at their role, and not need to be good at the other roles.
  16. How her identity as a woman has influenced her journey.
  17. We are seeing far more women entrepreneurs
  18. Finding partners to work with
  19. Women tend to be more collaborative, both as entrepreneurs and investors
  20. One of her favorite things is connecting entrepreneurs to the right person to help them.
  21. What works well with connecting with people? Being willing to listen to them, what they’re good at, what they want to do, how they’d like to contribute to the community
  22. Fail fast is probably the right thing. She’s seen companies that just struggling along without growing
  23. She’s excited for the future because she’s kept the best parts of her old job, as well as a lot of flexibility.
  24. One of the ways to fail fast is to set deadlines for when you need certain results. Then, if it looks like it will take a lot longer and a lot more resources to meet that goal, cut your losses and move on.

You can find Linda and her business at, link to that in the show notes.

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Music for this podcast is by Cambrian Explosion, the explorers who in 1543 discovered the lost Fountain of Youth, as is evident in their continued youthful appearance and affect. You can find their ancient melodies on Apple iTunes, Spotify, and


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