The Startup Sessions Interview

Over the past year, I’ve been working with the legendary, massively smart and overwhelmingly delightful, Michael Knouse.

From March to May, Michael and I worked together designing his logo, business cards and website, and he was nothing short of a dream client. What makes up a dream client? Well, it’s not an exact science, but for now I’ll define it as one-part personality, one-part initiative/really understanding your business, and one-part business idea/project. And let me tell ya, Michael has all three going for him.

Since Michael is a local Portlander, and I was so sad when our project was over, I volunteered to take him out for some celebratory beers at a local pub in our neighborhood. We got to talking over some Boneyard IPAs, caught each other up on our pasts and started to look toward the future. It was then I let him in on my big news: I had just put in my two-weeks notice at my corporate job and was ready to pursue freelancing full-time. Immediately, Michael wanted to interview me for his show, and I couldn’t have been happier to oblige!

So, here we are! In this interview, I’m not talking about design or color palettes, e-mail opt-ins or mood boards. But I am talking about:

  • How I built up my side freelance business enough to finally quit my full-time day job to pursue my dream.
  • Why my day job was the best training ground for growing my business.
  • What finally pushed me to make the big leap.
  • How to create a solid financial transition plan.
  • Why we keep making excuses to stay at our day jobs.
  • What I would have done differently if I had to do it over again.

Hope you enjoy this little glimpse into my business, and please start following the inevitable climb of The Startup Sessions! You’ll be glad you did!

Natalie McGuire

Hi, I'm Natalie McGuire!

I'm a website designer + digital strategist who believes in design with strategic ease. Meaning, gorgeous design is informed by customer insights that make your business a whole lot easier. If you want to stop losing customers by having "just another pretty website," work with me.

Stop losing customers by having
“just another pretty website.”

Natalie McGuire Designs: Design with strategic ease


Natalie McGuire Designs stands against inequality, injustice, hate, discrimination, and systemic racism, and is deeply committed to investing in diversity and inclusion, and standing up for what is just, inclusive, loving & equitable.