Cascade Angels, Bend’s own organized angel fund, has been growing since its inception in 2014, both in the dollars it has to invest and the number of companies in its portfolio. To date the organization has invested $2.7 million into 17 Oregon companies. Most recently, the fund expanded its leadership team to include Robert Pease, who will join the organization’s co-founder Julie Harrelson. They will serve as fund co-managers.

Robert has more than 20 years of experience as a startup investor, founder, executive and consultant. He and his family moved to Bend last year from Seattle, and Robert dove into the startup scene immediately, working as a community advisor with Cascade Angels. If you’re headed to next week’s EDCO PubTalk, you can meet him in person–he’ll be moderating the panel discussion on SaaS marketing. In meantime, we caught up with Robert to learn more about his startup experience, lessons learned over his career, why he isn’t a fan of ping pong tables and how he really feels about barbecue.

Robert Pease

SUB: You worked with startups both as part of early teams and as an investor and advisor. What do you enjoy about working with early stage businesses? 

Early stage businesses are about what is possible and entrepreneurship is exciting, scary, rewarding, and soul crushing all within the same hour of a day. It takes a special kind of person and I am constantly in awe of great entrepreneurs.

SUB: Related, you experienced startup culture in Atlanta and Seattle through the early 2000s and came away with, among other things, strong feelings about ping pong tables at work. Do you hate ping pong? 

Hate is a strong word, but work is not a playground…it is work. You should never take yourself too seriously, but you should be very serious about your work. If you need to take a break, take a walk. It is better for you and doesn’t disturb anyone else.  Rarely are the highest performers at a company to be found playing ping-pong in the middle of the day. At least I’ve never seen that to be true – sample size of one and all that.

SUB: What do you count as your biggest startup success? What did you learn from it? 

There is a very thin line between success and failure. I have seen both sides and even some of the “exits” I have been through have been finishing well vs. cashing out.  It is better to be bought than sold, and you don’t want to underestimate both timing and motivation on both sides of a deal. I will say that over six startups (both success and failure) my greatest reward has been working with great people and having the opportunity to help their professional development. That is not always a priority as you are often “building the plane while flying it” but startups offer the opportunity to do more, earlier in a career than just about anything else.

SUB: When you have failed, what did you takeaway from the experience? Was it valuable? Painful? Both? 

I’ve experienced failed companies, failed products, failed campaigns. If you have the courage to try you will fail because you try often. Failing sucks, but you got to believe. If you don’t, your team won’t. If your team doesn’t believe, the market won’t.

SUB: You officially moved to Bend last fall. What drew you to Central Oregon’s startup community? 

I went to a PubTalk in 2015 after getting involved with LeadMethod here in Bend and was blown away. Blown away by the energy, talent, and authenticity of the people.  Amazing things happen when you mix great people, opportunity, and capital and Bend has all those things and more.

SUB: What do you hope to accomplish in your role as fund manager of Cascade Angels? 

Raising money is hard especially at the earliest of stages. While a return on investment is the primary goal, helping entrepreneurs be successful and partnering with them on a journey that can be difficult and lonely is what I look forward to the most. I’m excited to be working with Julie Harrelson and building on the great foundation she created for a seed stage fund focused on Oregon and the Pacific Northwest.

SUB: You come to Bend from Atlanta by way of Seattle. You have a smoker in your backyard and no giant hunk of meat within a 10 miles radius is safe. What do we need to know about barbecue? 

I gave up trying to find good barbecue when we moved to Seattle so make my own. And, for the record, it is a “barbecue” only if you are cooking it otherwise it is a “cookout.”  Grilling steaks? You are cooking, outside. Cook-out, get it? But barbecue. Barbecue is about taking less expensive cuts of meat, seasoning the heck out of them, and slow cooking them to a state of awesomeness. The craft is in the seasoning and smoke. Don’t destroy it with too much sauce. The meat should carry the flavor and sauce enhances it.

Kelly Kearsley

Kelly Kearsley, the co-founder of StartupBend.com, is passionate about startups, entrepreneurship and Bend. In addition to writing this blog, she creates content and manages content projects for global financial companies, tech firms and startups. She began her career as a newspaper journalist and later worked as a freelance writer. Her work has appeared in WSJ.com, Money Magazine, CNNMoney, MSNBC and Runner's World. See her work at kellykearsley.contently.com or kellykearsley.com.

You can reach Kelly by email at [email protected].
Kelly Kearsley