Brand Development & Adventure Capitalist

Join The Fun



What the heck is Middlestetter?

We can’t help to wake up every morning and think “Life’s a garden: dig it” – then brush our mullet and head out for another day of whatever adventure is ahead. We are stoked to work on projects big & small with each one bringing us joy. So if you’re here just trying to figure out what the heck is going on. Short story… We run businesses, work with businesses and help businesses grow; and have fun doing it.

We offer 3 engagement options:

  • Wholly owned brands
  • Partial ownership / Collab & Adventure Capital
  • Consulting advisory board engagements

where you want to be; Sooner.

Stressed out? Always late? Missing out on Life? Working harder than ever?

Yeah, we’ve done that too.

Your guidance counselor lied to you. You don’t have to work hard to live well, but you do have to work smarter.

Getting to that sweet spot, the place where its always “summertime and the livin’s easy” – that’s what we want to do with you.

We don’t sell anything, we collaborate with your business via Brand Development and Adventure Capital – We only succeed when you succeed. We are not about to go back to working hard for little – so rest assured that you’re going to succeed.

Matt Middlestetters offline Oregon cabin


Matt Middlestetter Fishing

Adventure, Entrepreneurship & Service; Work on what you love, and love to work.

Entrepreneurship has always been a part of Matt Middlestetter’s life. Starting as a teenager in the garage with a skateboard wax company that somehow wound up with international distribution. Then fast forward 20 years to the sale of his multi-million dollar technology business. Through the years we have maintained the same approach. Love what you do.

Middlestetter has collaborated with brands big and small – the principals are the same. Microsoft, Intel, Daimler Chrysler, Kellogg’s to your local coffee shop. Anything for a cup of jo. 

Middlestetter knows the most important thing about business is to support you in living your best life, not be your life. And speaking of life, what are you doing with it? How does your business service your personal goals and others?


Brand Development

Craft Unique Offerings, Increase Client Satisfaction, Create a Company Culture, Develop a Sustainable Marketing Funnel

Adventure Capital

Active Investment, Development & Growth, Expansion or Franchise


Tried & True Growth Planing, Client & Culture Problem Solving, Brand Brainstorming and Traditional Business Consulting

Exclusive Partnership

MSP Coaching

Are you an IT Managed Service Provider?

Middlestetter has an exclusive partnership with Bering McKinley the top management consulting firm in the industry.

What are you waiting for?

Matt Middlestetter snowboarding in Canada with bird on head