Why I broke up with Portland to build my startup… and why we’re back together

[Editor: It’s been a while since we’ve had a guest post from Darius Monsef, founder of COLOURlovers (one of the first Portland Web startups I started following here on Silicon Florist). Want to hear more from Darius? Swing by PIE on Tuesday afternoon.]

She was a dream city with everything I hoped for. I was willing to work long hours and scrape by on the leanest of incomes to make things work. I tried again and again… but ended up having to abandon her to find real opportunities in new cities. On my journey I travelled to the mystical land of Startups. I saw over the wall into the secret garden and I’ve returned home to share what I’ve learned… and to be happily together with PDX again.

Falling In Love With Portland.

Before my story of leaving Portland begins, it helps to know how I got here. After leaving my childhood home in Hawaii and moving to Boston for college, I realized that the itch to build things was greater than my desire to be in a classroom and took a job with a small web design and development shop in Portland. (My mother’s side of the family has always been in Portland and I’d visited often growing up.) It was at this small shop that I cut my teeth building dynamic sites and services.

COLOURlovers was born one long weekend from two parents: Experimentation & Inspiration. I mocked up a design and wrote the code to allow people to choose a color, name it and then let others rate and comment on it. (HotOrNot.com for Color.)

This was a social experiment to see how others might see colors differently. Do you absolutely love this color? Does this one make you vomit in your mouth a little? When the MVP (minimum viable product—I didn’t use or know this term at the time) was working I shared it with a flash community I was a member of and started getting great feedback. From there I added the ability to add a color combination of 2 to 5 colors as a palette. And with that the site became more than just a rating site and an inspiration source for people looking for color ideas to jumpstart their projects.

tl;dw: Five weeks after I built COLOURlovers v.1 I left to Thailand to volunteer for a month after the Tsunami struck. I ended up staying for 5 months and cofounding an international relief organization. (LO Review Story.) After two years I stepped down from operations of the organization to return to tech and try and hit my home-run. So I can do that much more good in the world.

Breaking Up With Portland.

After returning to Portland, I took a small family angel investment to hire a developer much better than me to take over building the site. In its current state, tt was falling on its knees from continued organic growth combined with my shoddy coding. I found a local developer on craiglist and hired him to rewrite things. (Chris is now a partner in COLOURlovers and has written all the code that makes the site run now.) I started going to local startups events to meet other founders. I went to pitching events to try and meet investors. I wrote for blogs like this to get awareness in Portland. And the more I tried to really make something happen the more I realized that Portland and I needed to see other people.

I don’t love being Darius Downer and crapping on the Portland web startup scene, but somebody needs to critique what needs to be critiqued and bullshit needs to be called what it is. I care very much about Portland and would love to see the startup scene change, both for my own company and for every other founder hungry to build their ideas here. But Portland is not a great town for startup founders right now. And it won’t change from the top down. We as this generation of founders need to bleed more to make the road easier for the next to walk.

So, if I can help any of my fellow founders please let me know. I’ll bleed with you.

A Startup Community Needs 4 Things: Ideas, Talent, Ambition, and Capital.

We have amazing people with great ideas in Portland, some of the best creative comes out of this town. Portland also has skilled tech folks. We’re hiring our team out of Portland for this reason. And it isn’t like nobody has ever made it big out of Portland, there are several great PDX web companies (Urban Airship, Kongregate, and Jive Software, for example) whose ambitious founders overcame what obstacles were in their way.

What Portland doesn’t have is capital. Founder friendly, fast moving seed capital. I tried raising money in Portland—granted it was a couple years ago—but all I got was dicked around by a VC that didn’t really have money to invest and ended up just using me as a screen to social proof leads. And from the outside, my inexperienced and misguided attempts to pitch valley investors went nowhere.

A Startup Community Doesn’t Need 4 Things: Coaches, Advisors, Hired Guns, The Cullens

It totally makes sense that somebody would want to see that you’re willing to bleed for your ideas to test your commitment & passion. But run away from people asking you to bleed into their mouths. There is some truth in “those who can’t do teach…” And many of the people out there selling their coaching / advising skills haven’t had any material success in the space where they espouse wisdom. Be very wary of any coach who needs your money.

Coaches are on the same spectrum as advisors and investors… but not on the end you want. Paul Graham once cautioned me about advisors: “Be careful about getting advisors. An advisor is just somebody who doesn’t believe in you or your idea enough to invest in it.”

And a hired coach is somebody that is primarily motivated by your cash. If they truly believed in what you were doing, they’d invest in you.

Coaches < Advisors < Investors < Baby Unicorns

With that being said, we do have two official advisors. Both are active entrepreneurs who have a ton of amazing experience. They’ve continued to give me advice and support without asking for anything in return. In appreciation for their time and their continued support, we made them advisors. I also have dozens of fellow founders that I count as advisors. Which brings up another piece of wisdom: Get advice from people actively in the game.

The kind of mentors, coaches, and advisors (incubators included) you want the most are people who are invested in you and your success. And their are tons of amazing successful entrepreneurs and investors out there actively investing in startups. You just might have to look outside of Portland to find them. I highly recommend Angel.co and am happy to help any startup ready to start pitching investors refine their pitch and put together a funding strategy.

(Full Disclosure. I was once on Team Edward, trying to survive as a bootstrapping entrepreneur by coaching other startups for cash. I hopefully gave greater value from my lessons learned than the blood I drank.)

And along with the for hire coaches there are organizations that I think could do a lot more to help web startup founders:


Most startup founders don’t know SCORE, because it is a dinosaur of an organization that is meant to help small business owners get started. While this may be useful for brick & mortar / mom & pop shops. It is not at all helpful to internet startup founders.

I reached out to SCORE to help get business plan advice and fundraising help. I was matched up with an older businessman and met him at the their offices. Only a short while into my meeting with this “advisor,” he told me that he couldn’t help me through SCORE, but if I worked with him outside of SCORE (gave him equity & finders fee) he could help me get investment.

The internet world moves fast. Hell, I’m only pushing 30 and I feel like an old dog in this game. SCORE doesn’t have advisors who understand the current web startup world and will have little value to provide you as a founder.


While better than SCORE, I don’t think OTBC is providing the value it can be to the startup web scene. I think they are a great resource to hardware, biotech, and physical product companies. But if OTBC really cared about helping Portland web founders, they’d be networking their faces off with SF & NYC investors and other successful startups. They’d be deal makers and intro-magicians helping Portland founders meet the investors they need and get partnerships off the ground with other successful companies.

I was a paying member for a couple years. I went to several of their events. One even I went to was a business plan writing workshop (FYI, you don’t need a business plan. AT ALL.) and I approached the speaker to introduce myself and get some specific feedback. He blew me off.


Like OTBC I think OEN provides real value to companies outside of the web startup scene. Their beauty pageant events will waste your time. Time if you invested building your MVP, you’d be launched.

Seeing Other Cities.

While bootstrapping COLOURlovers in PDX, struggling to raise, and take things to the next level I was recruited by the team at Microsoft working on Photosynth. I accepted the offer to move up to Seattle and head up building community and web product for their killer application, thinking that I could use the serious increase in pay to fund my startup and use my spare time to work on things.

I overestimated how far the extra cash would take me and underestimated how taxing a day working in middle management at MSFT would be. I wasn’t able to engage the startup scene in Seattle much but I was able to bang out a new project while up north (Friendscall.Me) and ultimately get it acquired.

With my entrepreneurial soul being sucked dry in Seattle, and with the extra motivation of an amazing woman (now my wife) I moved to San Francisco to live the startup dream.

San Francsico has been amazing. Even before getting into Y Combinator, simply having a city made up of founder peers was opening my eyes. (I wrote about the values of doing Y Combinator here.)

Not to overhype it, just honestly… SF has been like Disneyworld for me as a founder. But I still love Portland and think it can be a Disneyland. Let’s make some magic happen.

Make-Up Love’n with Portland.

I’ve wanted to share a lot of these thoughts for a very long time, but felt like I needed to exhaust my options, try every service I could, and prove things out before making any critiques.

Well, I love Portland. I REALLY want to see it thrive as a startup hub. We just raised a large seed round from some of the top VCs and Angels. We’re hiring here in Portland and supporting the local economy. And while SF will continue to be my homebase, I’ll be in Portland often and supporting the startup community as much as I can.

I realize that there are a lot of service providers here in town, the coaches and the advisors that are not going to like what I have to say. And trust me, being critical is not one of my favorite things. I’ve built my personal brand around LOVE!

But I’m not here for them. I’m here for my fellow founders and I’ll take your flames to support them.

If you have a startup that you’re bleeding for. Come bleed with me. I’ll do all I can to support you. And with the success of this generation, we’ll grow a thriving startup community in Portland.

Darius Monsef can be reached via his blog, COLOURlovers, or as @bubs on Twitter.

(Image courtesy Iwona Erskine-Kellie. Used under Creative Commons.)

  1. […] Why I broke up with Portland to build my startup… and why we’re back together […]

  2. […] Why I broke up with Portland to build my startup… and why we’re back together […]

  3. […] You remember COLOURlovers, right? Remember? They’re the Portland startup that left for the Bay, got picked as a Y Combinator company, and is currently in the midst of renewing their relationship with Portland? […]

  4. […] Why I broke up with Portland to build my startup… and why we’re back together […]

  5. Kudos to Steve Morris and the volunteers @ OTBC. I also participated in the FasTrack program and benefited greatly. My web-based company, SafetyPlan, is live and generating positive cash flow using OTBC’s very practical playbook. There is a lot of money sitting on the sidelines in PDX, and when/if it is time for SafetyPlan to tap it, I am confident that the investors will respond.

  6. @Bubs — there are multiple approaches and no one-size-fits-all solution. To highlight my point about how a strong business-side (and experience) eases the path to entry for regional Investors, I look at this mornings news about the Angel Oregon awards, the top dollars went to a venture that is that mix of tech and business experience I refer to. It’s a successful formula here. But, the business/entrepreneur talent is slim. Some may prefer to not spend money or efforts on business affairs and management during early stages, some may. Some Investment regions don’t care (or, have the infrastructure to bring to the table themselves); others regions prefer to see experienced business folks as part of the founding team.

    These are all generalizations, therefore bound to bring up exceptions. But, my original point is that experienced business-side entrepreneurs are in short supply in this region. If there were more, they would ease the way for more local investment rather than having to import dollars.

  7. Cotten Blackwell March 16, 2011 at 11:00 am

    Whoops, forgot to mention:

    *My startup* was a web / mobile app startup, but I still felt I needed help on the business fundamentals (market research, concept development, pricing, etc.) — which I got in spades at OTBC.

  8. Cotten Blackwell March 16, 2011 at 10:49 am

    I second the posts here by Elia Freedman and Steve Morris — OTBC does not deserve to be lumped in with the self-interested bloodsuckers you rightly warn about.

    I participated in the 10-week FastTrac program from the Kauffman Foundation facilitated by OTBC for the first time in 2008. I thought Steve Morris did an excellent job of bringing in helpful, practical speakers like Mark Paul, whose books I also recommend.

    Bottom line, my time and money spent at OTBC was a huge bargain, and I would recommend it to others. I just wish I had found them sooner in my startup process!

  9. Darius -I do appreciate your willingness to help other entrepreneurs, and I enjoyed the session at PIE last night. As Elia said in his comment, we need more people who are willing to give back. But there are a couple of points I need to comment on:

    “… a hired coach is somebody that is primarily motivated by your cash.
    If they truly believed in what you were doing, they’d invest in you.

    I’m sure there are some coaches that earn that description, but non profits like OTBC don’t. I believe places like OTBC and OEN add a lot of value. We couldn’t exist – we couldn’t do the fund raising we have to do (most of OTBC’s support comes form the City of Beaverton) without showing some revenue. But non-profit fees are hugely discounted. Example: our venture membership is $69/mo. If you get 4 hours of coaching for that in a month (it’s typically more) then that’s costing $17.25 per hour. Believe me, that’s not enough cash to be “motivated by”.

    Another example: our 3 month boot camp is $900 – think of it as $300 per month (and we’ll probably be able to offer some scholarships to lower that). For that participants get 24/7 access to the OTBC facility for up to 3 people. That’s office space for 3 people, including Internet, conference rooms, lots of white boards, staffed reception, free coffee, and the opportunity to spend3 months working next to a bunch of other entrepreneurs – for $300/mo. On top of that, there’s a lot of coaching, lunches with investors, and CEO guest speakers (yes, even including web entrepreneurs). $300/mo. is an incredibly good deal just for the office space for 3 people. So think of it as a great deal on office space, and the coaching is free.

    It would be great if we had an investment fund so, like Y Combinator and TechStars, we could invest. We’re working on some options along those lines for the future. But we didn’t want to wait – so for now, we need to charge.

    “Get advice from people actively in the game.”

    Agreed. And it’s true, none of our coaches are running a successful web company right now – if they were, they probably wouldn’t have 4 hours per week to donate. (And yes, aside from me, all of our coaches donate their time.) Instead, we get get speakers who are in the game – including web entrepreneurs. But I think you under estimate the value of coaching from entrepreneurs who are “between gigs” (having been at 3 startups – 1 successful, 2 not – that’s the way I think of myself) and from other experienced execs and investors, whether or not they started a web company. There are quite a few web entrepreneurs who believe they got a lot of value from OTBC coaching – just check out the testimonials on the OTBC website. None of them are huge successes – yet – but give them time.

  10. @Jmartens

    You looking to invest?

  11. I agree with many of your points but would add one more thing that a start-up needs: luck. A little bit of luck to have the right idea, a little bit of luck to have it at the right time, a little bit of luck to find the crucial first team members and so on. It might be different for the serial entrepreneur but I think anybody who does this the first time will agree that a start-up can be a very lonely place. And for those lonely times organizations like OEN, OTBC or Starveups are very helpful. It would be great to have more organizations like this in Portland, it would be great to have many more successful serial entrepreneurs involved in those organizations, it would be great to have many more of these entrepreneurs be filthy rich and invest their money in the next generation of Portland start-ups, but – Portland is not that lucky (yet).

  12. @ Sam2.

    I think we both care about supporting the Portland startup culture, we just have different approaches to helping solve the problem. I totally get your viewpoint on working to help current local VCs and investors be wooed into feeling comfortable about investing in web startups. But I’ll leave that to a better man.

    I’m going to focus on supporting local founders to find a level of success where they can turn around and invest in their own community and I’m going to leverage my connections to investors that get it and are willing to invest in Portland companies even if they don’t live here.

  13. @bubs — My point was that you can ease the traditional VC or old-school Angel (Pacific Northwest breed) if you play by some of their rules and don’t go all Silicon-Valley on them (“five year projections are meaningless…” even though they are).

    I’m not disagreeing with you in principal, but in practical terms of achieving the seduction.

    So, yes, here in the great PNW, having some business acumen on-board helps with the seduction. Having a business plan not only helps someone really think through their product (along with it’s pitfalls and competition), but, it smooths the seduction as well. We don’t have a pool of Super Angels or Super-Angel-Wannabees hovering about. We have old school money who will “play,” provided they are wooed on their own terms.

    On the whole, people want to see successful businesses here, not just deals that flip or crater and then result in someone doing larger seed rounds for some other venture. The PNW will NEVER have that mentality, at least not in my lifetime. Having teams of Cofounders that are a combination of tech and business oriented could create a lasting value here; rather than fleeting value elsewhere.

  14. Did Paul give you some Customer Driven Development books? Perhaps something like The Four Steps to The Epiphany? Those are indeed helpful concepts for understanding how to build products your users want.

    You may be the one of the success stories, but I’ve seen a lot of non-tech founder companies fail by being stuck under the development contract bus. I wrote about that here: http://siliconflorist.com/2008/08/11/heres-the-deadliest-catch-hiring-an-agency-to-build-your-startup/

    As for business plans… I’ll have to disagree. (And we still have no business plan and are doing just fine.)

    While it is obviously useful for the team to know what it is they’re building and why… A lot of the far off planning that goes into a business plan matter a whole lot less in an industry that changes super fast. This point is similar to the ones I made in the link above about hiring an agency. When it takes weeks if not months just for the company to spec the project and then give you a quote, that sort of rigid approach doesn’t support iterating and pivots very well.

    In the early stages of a web startup, I think the broad vision is more useful than detailed long term plans. If you’ve proven out your market a bit and have early solid traction… and are prepping for massive growth… then having the detailed plan becomes more useful as the team scales and layers of organization become more important.

  15. I am leading a web-based software start-up in Portland. We hail from the business side and are not programmers. This has brought both advantages and challenges to our start-up endeavor. I have found OTBC to be of great help to us. My coach Mark Paul gave me two books that helped me understand the key to forming a start-up business. If I had gone to OTBC earlier, I might not have wasted months trying to “sell” and instead had my customers design my product, price it and tell me how they want to buy it. In my experience, these lessons are useful regardless of wether you are a web business or traditional business. As far as not needing a business plan, perhaps you don’t need to show one to an investor but if you haven’t thought through your business in substantial detail, you are missing something and that will cost you and or your investors time and money. Planning is key to a successful business. Start-up teams with a well defined product, customer, value proposition, technology, competitive advantage, sales and marketing strategy and exit have a chance. Those without wont hear the bullet that gets them.

  16. For the record, in my 14 years of running a mobile software company, I have met lots of wonderful people here who have helped me along the way and have had highly successful careers with start-ups and established companies. I met some of them through SAO, OEN and OTBC, and others I met on my own. People like Pat Cox, Bob DeKoning, Steve Morris, Dick Luebke and Holly Files, just to name a few off the top of my head, have been outstanding resources over the years.

    Now, do we have enough of these high-caliber folks around? No. And do we have deficiencies in the funding environment? Yes. Personally, while I am not a Portland fanboy per say, I hope that I can build a business here that will allow me to invest back in this community, bringing my own web/mobile experiences to the table for them. What we need are more people who will contribute back to this community, as Scott Kveton and Jason Grigsby do, not less.

  17. “Interesting views…”


    “Portland spawns an awful lot of successful start-ups, maybe not in web, mobile, or software, but take a look at other industry segments and you’ll see some real success stories.”

    Yup. The whole post above had nothing to do with the other industries, I mentioned several times that I was speaking specifically about the web startup scene.

    “I do see the aforementioned retiring corporate execs doing local investing. But the prudent investor tries to pick segments he/she understands personally.”

    Exactly. The investors in Portland don’t understand the web world well.

    “The last two decades are littered with hundred million dollar investments that went in the toilet.”

    And hundreds of million dollar investments in Real Estate, Stocks, etc. that went in the toilet as well. Nobody is saying that all investing is smart investing. But web startups don’t needs millions of dollars to get off the ground. I’m not saying that a napkin idea from green founders should get a million dollar seed round.

    But what I think PDX could really benefit from is some web experienced angels willing to write 10-50k checks without much standard VC grief.

    And to be clear on how we both approach things, it looks like you’re a professional advisor & service provider… so I understand where your perspective is coming from.

  18. Interesting views. Lots of them b.s. tho. Start-ups need grey haired advisors. Keeps the investor’s money from all going for ramen, red bull, and pinball machines. The last two decades are littered with hundred million dollar investments that went in the toilet. Can’t get your start-up financed? Maybe it’s not the earth shattering idea you think it is.

    Portland spawns an awful lot of successful start-ups, maybe not in web, mobile, or software, but take a look at other industry segments and you’ll see some real success stories.

    I do see the aforementioned retiring corporate execs doing local investing. But the prudent investor tries to pick segments he/she understands personally.

    Finally, one of the most important things to remember when pitching investors or VCs? They aren’t looking for a reasont to say “yes”. They are looking/listening for a hundred reasons to say “no.”

    Keep that in mind as you craft your pitch, and your pitch team.

  19. Great post, but I think you may have left out the discussion of the larger culture of PDX that is, in many ways, anti-start-up. Not in specific business way, but in the way of how people value relationships there. Friends vs business partners.

    I grew up and started a small creative biz in PDX (non tech). After 3 years of struggling and having a lot of over coffee meetings that in retrospect were more just hanging out – even if inspired – I moved to NYC. 7 years in NYC, and if you asked me when I started my business, I wouldn’t even include the Portland years, PDX seemed that silly after working in a real major market.

    I loved PDX, still do, but for the opposite reasons that have to do with work. And while poor biz/management talent and tough to get money can exist anywhere, the bottom line is PDX is largely comprised of a lot of people that don’t have a lot of big biz and big picture experience, and it shows. People will spend hours discussing how amazing the sauce is going to be and nobody is talking about the meat.

    In a word, small time. As a broad generalization of course. Start-ups are brutal business and about getting ahead and surviving – now more than ever – they’re not about making friends and hanging out…the pdx scene never really respected that. They got it, but just didn’t embrace it. Which is fine, and again a reason to love the city. But look, I don’t live in NYC to make friends, and if I told a Portlander that, they’d prob give me shit for it, that it’s not cool. and that there is the big reason PDX was stifling for work.

    When I go back there to visit friends , for the first few days I see all the things I miss, but after interfacing w/ people for a few days I quickly remember why I left.

  20. @ Chris,

    I guess it’s a little chicken & egg. When startups have exits or when their founders get liquid, they’re able to invest in other startups. It this kind of seed capital that fast moving $ that helps a startup scene thrive. IMHO. SV has lots of investors like this. (75% of our investors are founders/early-hires)

    Portland does have investor folks, but I think a lot of them got their $ from being long term employees at places like Intel or from more brick & mortar business ventures. They don’t understand the web world as well and are less likely to invest in seed stage companies.

    Unfortunately Portland hasn’t had a lot of big startup successes… yet. I hope our generation can slog through the challenges now to become the next generation of seed investors later.

    I know there are other companies in the PDX area that are bootstrapping and working their way up. I think Rick is doing a killer job keeping this site as a voice for the startup scene in PDX… and PIE is a fantastic place for people to come hack together. I’d love to start organizing more Founder events here in PDX. I have a weekly breakfast with fellow founders down in SF and I think it would be awesome to get something going up here too.

    No offense to those on the edge of founder land… but one thing that got frustrating when I was up here trying to network with other startups before was that a small % of people at the web tech / startup events were actually working on their startups full time. I want to support them too and I think there is a way to organize events to help them get some questions answered and fears mitigated to help them go full time… but I really want to be able to sit down with a group of peers that are going / went through the same things.

  21. Thanks for this article. Good to hear others perspective.

    The lack of capital flow in pdx is well documented. I’d love to hear deeper insight into why capital isn’t flowing here.

    I’d also love to hear much more about companies who are bootstrapped, not just because we’re one of them, but because they often get little to no press in the major tech blogs. TC, Mashable, RWW, Fast Company… all guilty.

  22. @Mr Diggles-

    We have to be careful not to measure the “lack of capital” in PDX based on your company’s experience. Just because a company doesn’t get capital doesn’t meant that there isn’t any. Not all businesses are exciting to individual angels and not all businesses make sense for venture capital.

  23. Wow, you completely nailed the Stump Town capital community or lack thereof. I made my rounds in ’05 & ’06 and ran into the exact same scenarios with the local VCs and Angels. Most were living off the stories of wins they had a decade prior, the others were living off walking dead companies from an underfunded VC with little ability to raise more cash.

    We found that the organization most dedicated to fostering an environment ripe for startup growth was our law firm. They gave countless hours of their billable hours towards council and meaningful introductions to VCs in and outside of Portland. Shouts out to Ater Wynne, LLP.

    Great article.

  24. @ Colin.

    Ahh… The great K one that shal not be mentioned 🙂

    (COLOURlovers has always been highly supported by the Kirupa community. We actually just hired on a Kirupian from the old days.)

  25. Sam.2,

    “No matter how clever and wondrous your code and concept may be, you need experienced people with business acumen to come on board, either early-stage or not long thereafter.”

    While I agree that sometimes a tech founder who has no business / social skills could really benefit from a business saavy co-founder, I would say that a BD role is not needed to found a successful startup and that role can often be hired on later… or brought on for a much smaller equity chunk.

    “…Someone who has no fear of spreadsheets and creating the types of reports that real Investors want to see”

    In my experience, investors don’t want business plans and 5 year financial projections at the seed stage… and seed stage, web startups is what my whole post above and conversation is about. If you’re opening a physical product business, then those things become more important.

    “Investors will take risks, but only if you give them a bit of the old “familiar” that’s in their own language.”

    That depends on who the investors are. If you get investors who are in the web scene and understand what’s going on, then you’ll speak the same language as them… If this is an old school venture dude who hasn’t invested in seed stage web startups much… then yes. (Portland needs more of these seed / micro-VC investors who deeply understand the startup industry.)

    “You need the experienced business team who can open doors to markets, partnerships, business affairs (without it costing you a Retainer) and investors”

    Again, this really depends on what you’re building. If you product / service integrates with more traditional Fortune 1,000 companies, then yes… somebody with more traditional BD experience is super helpful. If you’re just trying to get Firehose access to Twitter, you can navigate that yourself. And not sure what else you mean by business affairs… Most startups should have minimal overhead costs in the early days as they build and launch their product… At some point you can hire an outsourced HR firm to run your payroll, health insurance, etc. But you can handle this yourself for the first phase.

    “There’s a great shortage of business-side co-founders or equity partners available in this town who can add the weight and credibility needed for local/regional investment.”

    I think the problem there is that the current investors in the PNW are the old-school VC types that want the business plans and 5 year projections. These are not seed stage investors. The only credibility you need to get investment from great seed stage investors is talent & some form of proof you’re building something great.

    “It’s slim pickins on that side of the talent pool here.”

    I’m curious, have you been hunting for somebody like this? Why?

    “If you don’t want to start a real-business that has a Plan, head South.”

    Not sure what you mean by “real-business” but maybe you could give me some examples of those? I know a lot of successful web startups that never had more than Page 1 of a Business Plan written.

  26. Really great post! Thank you for your honesty here.

  27. @Bubs,

    I would like very much to speak with you in person about Portland. Either there, or when you’re back here (San Francisco).



  28. More that’s missing in PDX…

    No matter how clever and wondrous your code and concept may be, you need experienced people with business acumen to come on board, either early-stage or not long thereafter. Someone who has no fear of spreadsheets and creating the types of reports that real Investors want to see (particularly, if they are more on the shy and conservative side). i.e. Investors will take risks, but only if you give them a bit of the old “familiar” that’s in their own language.

    You need the experienced business team who can open doors to markets, partnerships, business affairs (without it costing you a Retainer) and investors — Not investors who will coin-in so you can attend groovy conferences (they don’t exist and likely never will here).

    There’s a great shortage of business-side co-founders or equity partners available in this town who can add the weight and credibility needed for local/regional investment. Not the kind of cred you get from an interview at SXSW, but, the kind of cred that’s needed here in the hinterlands to make people comfortable with taking new risks. It’s slim pickins on that side of the talent pool here.

    The examples of start-ups who’ve done well in PDX represents ventures that were equal parts tech and business. Younger start-ups tend to overlook this necessity. If you don’t want to start a real-business that has a Plan, head South. If you have a Plan and the team to pull it off, there are dollars around.

  29. Glad to see ColourLovers grow after all this time. I remember it from its infancy back on that little flash community that started with a K. 😉

  30. @ Blorch
    Yes, you can count web as “web: sites, services, apps, mobile apps, etc.” I was using it to generally refer to startups that revolve around the internet.

    @ Mr.Diggles
    I remember seeing Garetts wallets at the sat. market and then popping up in retailers all over… that’s some serious hard work making a physical product and then getting retailers to take it on. I’m glad SCORE was able to help you early on, that’s the first success-ish story I’ve heard about them.

  31. amen brotha, amen.

  32. I love this post!!!

    My business parter Garett Stenson and I started db clay – the hip wallet company that emerged from Garett’s success from hand making duct tape wallets and selling them at Saturdays Market.

    We used SCORE at the very beginning and it made a huge impact on our business. I always recommend it to others but they never seem to follow through with it even though it is endless value provided for free. As we moved forward we experienced the “coach” syndrome and had people coming out of the woodwork telling us what we should do – however when it came down to doing any heavy lifting those coaches sat on the bench.

    If anyone in PDX knows that our city lacks capital it’s Garett Stenson. He had conversations with every angel, VC and bank under the sun and even though they all were impressed with our business plan it never went beyond conversation. Despite the fact we had 600 retailers, massive conversion on our website and global consistent press. Lame!

    All in all I agree. Portland is what made us and broke us in a lot of ways. But the lack of capital is by far the biggest. Investors would ALWAYS say “sorry, I can’t invest right now… but can I buy a few wallets?” Comedy.

    Thank you for posting this. COLOURlovers is a staple for me to this day in my design approach.

  33. Amen to all points, doubly so for Coaches, OTBC, and OEN.

    You could just as easily swap “web” for “mobile software” as well. One other addendum: The West Side is for Hardware- if you’re looking to start a Software business, move your sights to Portland.

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