Inspiration & Advice11 Things I Learned from the Portland Startup Community

This guest post is brought to you by Maxwell Mirho, an Oregon native and a sophomore at Carnegie Mellon’s Tepper School of Business.


As a student at Carnegie Mellon University, I wanted to close my textbooks for a few months and spend the summer diving into the ‘real world’ of entrepreneurship. I knew there was much about being an entrepreneur that I wasn’t going to learn in the classroom. I decided the best way to a true education on the subject was to talk to the people on the front lines of the startup world.

Back in my hometown of Portland for the summer, I began networking within the local entrepreneurial community. In my free time, I skimmed through AngelList, consulted LinkedIn, found email addresses, and send out cold requests for meetings. I waited. When no responses came back right away, I began to think it was a waste of time.

Then suddenly I heard back from a couple people, and then from a couple more. Pretty soon, I had meetings with numerous executives and founders, and they were legitimately interested in talking to me. Over the course of the summer, I met with dozens of people at every level of the startup community from founders to venture capitalists.

What follows are 11 pieces of notable startup advice from my meetings.

Brian Forrester, formerly CEO of BuddyUp

Though BuddyUp eventually failed,  there are lessons in failure—perhaps moreso than in success. Even though Brian’s company went under, he had incredibly helpful advice, which included:

  • “Don’t just go to networking events.” At many networking events, you’re only going to meet other people like yourself with underdeveloped networks. Try finding events focused around someone important in the community, like technology showcases, and try your best to meet the people at the center of them. These people are already very well-connected and can make introductions.
  • “Get paid for what you’re already doing.” Before looking for more things to keep you busy, always seek recognition or (ideally) payment for something you’re already involved in. For a student like myself, that means making the most of extracurricular activities. To that end, I’ll be talking to my university advisors about getting class credit for my summer projects.
  • “Things that get measured, get done.” Brian believes that if you don’t constantly monitor progress with numbers and metrics, you’re less likely to finish what you set out to do.


Ben Nahir, Angel Manager at TiE Oregon

Ben is what one might call a “super connector.” In his position at TiE, he meets with an endless stream of people seeking funding from the angels that TiE represents. It’s probably safe to say Ben’s seen just about everything when it comes to fundraising pitches, and so he had some pearls of wisdom to pass along in that regard:

  • “Always ask yourself, ‘Do I really need outside investment?’” Ben emphasized the importance of entrepreneurs asking themselves this basic question. Convincing professional investors to put money into your company can be very validating, but the costs are high in both obvious and less obvious ways. If you can get to success with your own money, with cash flow from sales, or with support from friends and family, why would you take on the dilution, distraction, and hassle of venture funding?
  • “Don’t invest in the first 50 companies that pitch to you.” Ben received this advice when he started his job with TiE. Investment pitches are exciting by design. It’s easy to get starry-eyed, especially when the market is overheated. Slow down, get your bearings, and never forget the hard reality: most investments will be a loss.


Jon Underwood, CEO of cPay

After a good amount of pestering, I finally nailed down a meeting with Jon. His dynamic personality and intelligence were immediately evident, and the practical advice came fast and furious. Some highlights:

  • “Investors like entrepreneurs who have failed once.” Jon first heard this from venture capitalists that invest down in Silicon Valley. There are great lessons in failure. An entrepreneur who has failed is going to be smarter about a lot of things, potentially, than one who has only known success.
  • “You’re going to lose your early adopters.” Jon explained that in his experience with product development, there is always going to be a specialty group that likes what you’re initially selling. But to reach the broader market, you’re going to have to change your product in ways that will, almost always, result in the loss of your early adopters. It’s a situation Jon believes most early stage companies will face at some point.
  • “Word of Mouth Adoption (WOMA) is crucial.” In Jon’s experience, you need people to talk about your products. WOMA is crucial for generating the excitement that can lead to acceleration of a company’s sales, and it doesn’t cost you anything once it gets started.


Lou Doctor, President of CartLogic

Lou was one of the first people I met last summer, and his friendly attitude was a big confidence driver for me. Lou had a lot to share about e-commerce in particular, and his advice tended toward the operational aspects of building a team and running a startup. For example:

  • “You can only fail as a company because you don’t have enough money.” As obvious as this sounds, it’s also easy to forget. Treat every investment you receive as the last infusion you’re ever going to get, and make it last until the company is self-sustaining, however long that may take.
  • “It’s easier to fill demand for a current item than to create a new product.” Lou has a good deal of direct experience in this regard. Sometimes the money is in finding better ways to meet demand for an existing product, not in some brilliant new invention.
  • “Hire out of college.” Students are clean slates, original thinkers, and they can contribute much more than most managers assume. Lou sometimes uses simple pizza parties to lure college kids into a room, and then talks to them individually. If one of them asks smart questions, he might just offer them a job.

Many of the people I met with over the summer became more than mere connections; some have become mentors. Portland is, without a doubt, a great place to start a company. The community has avoided the intensity and exclusivity of Seattle and Silicon Valley. Friendly meetings flourish, and the sense of brutal competition doesn’t exist. People are supportive and willing to help, even if you’re just a humble student like myself.

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