Guest post: The Portland startup community is failing. Good.

Editor: Darius Monsef is a serial founder who has wrestled with the challenges of the Portland startup community, off and on, for nearing two decades. His first company, COLOURlovers, went through Y Combinator and merged with Creative Market before being acquired by Autodesk. He cofounded Sightbox which went on to be acquired by Johnson & Johnson. His latest pursuit is Brave Care, another Y Combinator alum that is rethinking the delivery of pediatric care.

I’ve credited Darius among the founders who inspired me to start both Silicon Florist and PIE. He has written Silicon Florist guest posts from time to time. A recent spate of conversations around community motivated him to contribute his thoughts on the current state of the Portland startup community, again.

Apparently today I woke up and chose violence, because what I’m about to say will likely be perceived as an attack to some in the Portland Startup community… but, know that I frickin’ love the people who I’m about to talk about. I’ve given of my time, money, and equity to support them. This isn’t hate; this is honest love.

The common theme we hear is that the community doesn’t support the champions that put so much of their time and energy into supporting it. But if we’re talking about startups here, specifically ones that operate in the typical venture growth lane… let’s be honest about how most startups fail.

They fail because there is no market for their product, or they fail to reach enough of the market to sustain operations, etc. This is capitalism (yes there are problems with capitalism, and systemic issues that do not create equitable opportunities but let’s address one issue at a time), and capitalism is competition. Not everything will survive, but the best will.

If a founder said, “I’ve been pouring everything I have into this startup for the past 10 years, but I don’t yet have paying customers” I’d tell them the honest truth that they should let that startup die. I’m not telling them they should give up as a founder, but I would say there is about 9.5 years too many of data showing them the current path they’re on is not the one.

They should pivot and find a business model / product that is viable… or quit, regroup and come back again with something else.

One of the dangers to founders in Portland is how loving and supporting the community is. They’ll back you no matter what. They’ll roll up their sleeves to bail you out and rally to help when you’re in trouble. That’s great in extraordinary times… but that isn’t good when you’re first testing product / market fit. Portland is your grandma, who will buy whatever you’re selling because she loves you. She is not a real customer and you can’t use her enthusiasm to validate your idea.

If you operate a program to support startups and can’t take equity or charge founders (to be clear I strongly dislike programs that charge money), then clearly your program is not worth the trade of $/%. The answer here is not to make the program free as organizations like PIE have done. It is to make the program valuable enough for people to pay for it.

It is the exact same situation for a startup who can’t get people to pay for their product… the answer isn’t “well they won’t pay so I’ll make it free and lose money.” Unless that is a strategic plan to take market share in a winner take all space or where you can monetize at scale… but this isn’t viable for most startups.

Should folks like Rick stop supporting founders? Abso-fucking-lutey not.

Rick, for example, has been a friend and advisor to me for more than 15 years. He’s one of the most generous and humble people I know… but should PIE die? Maybe. Because if the current product can not find market fit, continuing to support him in PIE means I’m keeping a friend from finding a real way to drive impact for founders and also get him well compensated for his time.

There are so many things to fix in the startup world… creating equitable opportunities for founders from backgrounds that have systemically kept them out… supporting founders who have extra hurdles to clear because of their gender, race, abilities, etc. I want to fix these things. I mostly angel invest in these founders. But, startups are frickin hard as is…

Don’t be shitty and exploit or harm people in your pursuits, but if you need to take care of yourself first… so that you can then reach back to help others forward. Take that step forward. Share your resources with the folks behind you as you go. But, if holding yourself back because you want to help others up at the same time as you means nobody moves forward… then indirectly you harmed yourself and others because you missed an opportunity.

It sucks to see people fail at any endeavor. But it’s like feeling sad when somebody gets divorced because they were in a shitty marriage. We can be sad because we wanted better for them, but we should really celebrate that they are no longer in a relationship that failed to give them the love and support they deserve. And now, they will hopefully know their worth and seek a partnership that truly honors them.

So if your startup is failing, I’m sorry the effort you put in didn’t get you the reward you had hoped for. I’m happy to help you find a pivot or new opportunity for your passion, skills and experience… but I don’t feel bad about not supporting you continuing on a path that is harmful to you and your potential. I want the best for you.

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