Advice, Community, Mentors

How to filter through all your startup advice this Thanksgiving

“Here’s what you should do.” It’s a sentence you’ve probably heard a lot. Friends, family, peers, mentors, investors—they all have helpful advice, but when your cousin Billy gives you business advice this Thanksgiving that conflicts with advice an investor gave you just last week, what should you do?

First, take a big bite of stuffing.

Then think about it. Advice and feedback is important, but you simply can’t weigh all feedback the same. Startups at PIE have spoken to peers, investors, and dozens of mentors over the past few months and here’s how they’ve sorted through it all.

How invested are they? How much care / concern do they have for you and your goals?

Kai, cofounder of Krumplr thinks about this every time he chats with someone. “You learn a lot of how to read people over time—customers, your bosses, people you manage, and across many different cultures. I start out by saying, ‘Does the person I’m talking to like me or not? Does the person I’m talking to care or not?’ And that’s something that you can very quickly establish. If it’s a positive relationship, I multiple pretty much any critique I get by a factor of five.”

You might meet with someone who doesn’t care and isn’t willing to put in the intellectual effort. Their feedback may be vague—platitudes in a way—like “focus your message”, “find your target audience.” It might be helpful to ask probing questions to find out if they really understood your problem.

There are on the other hand also people who don’t really care but are still willing to put in the intellectual challenge. “Those are good people to listen to,” says Kai. And finally, people who care and invest their time and effort to understanding your problem and thinking about your solution. That’s a given, pay attention to their input.

How experienced are they?

This one’s a little trickier to navigate because it’s often easy to confuse loud volume and confident delivery with actual success and experience. Aunt Susan’s confident remarks on how you should launch your business may sound extremely persuasive, but being an excellent baker doesn’t mean she has relevant experience in your industry. The same is true with anyone else who gives you feedback—investors, mentors, peers. Just because something worked a certain way in their field doesn’t always mean it’ll translate to yours. Levi from Droplr looks for people who have a track record of experience and success. He’ll give them extra attention if they’ve achieved success in his particular industry.

Are they willing to tell you the truth?

Kevin from Nutmeg appreciates individuals who exhibit a sense of trust with no hidden agenda. “The most value we received from PIE were from mentors who weren’t afraid to call bullshit right away. They’d say, ‘you should do x, and here’s why.’” Are the people you’re hearing from worried about offending you or hurting you? You might want to be careful if all of a mentor’s feedback is as sweet as that pumpkin pie. There’s nothing wrong with good feedback, especially if you’re on your A game as a startup, but make sure the person you’re talking to isn’t afraid to make you cry if they need to.

Are you receiving repetitive feedback?

Imagine arriving home on Thanksgiving day only to find your friends and family sitting in a semicircle around the front door. You soon realize that this is a planned intervention. They have a message to tell you—it’s important and everyone seems to realize it except you. (Let’s hope this doesn’t actually happen!) The point is, while there are multiple ways to run a business, hearing repetitive advice from a number of people is probably a good indicator that it’s worth listening to.

What’s your gut telling you?

Lastly, here’s the comment I heard from nearly every startup. Learn to listen to your gut. Ultimately, it’s your business. Deep down inside you know where you want to steer this ship, and you wouldn’t feel comfortable going against this anyway. Use feedback as a way to rethink your direction, but at the end of the day, if you can’t convince yourself that the advice you’re hearing is good and true, you might just have to go with your gut.

And while you’re having that Thanksgiving conversation with your friends and family, don’t forget to get seconds on that stuffing.

One can always make better decisions with stuffing.

Alumni, Community, News

PIE alum news roundup

While we spent the past few months rambling about our current PIE class, the PIE alum network was still busy making things happen.

Awards, features, and funding—here’s a brief round up of what some of them have been up to:

Missed PIE’s Demo Day a few weeks ago? Catch all the pitches from PIE Demo Day 2014 here.


What’s it take to intern for a PIE startup?

A few of the PIE startups have spent the past month working with this year’s fresh batch of Epicodus interns. Since they’re wrapping up their internship this week, I got them together to find out what their experience has been like.

What’s crazy is that less than 6 months ago, this group had their hands in completely different fields than what they’re in now. From the group is a high school teacher, another who worked in air traffic control, and others who did admin work and business development. They’re a diverse group that’s pretty proud of how far they’ve come with understanding and executing code.

To start, I spoke with Christian Danielson who’s working on refactoring the front end code base for Outdoor Project and the duo Catherine Chen and Justin Spears working with Read the Docs. “I initially began working on tackling some bugs,” Catherine said. The pair is also writing a bookmarking feature for Read the Docs users to further organize their documentation.

I also had a chance to chat with interns Jennifer McCarthy and Tanner Stewart who are working with PIE alum Switchboard. “They’ve got us building an app that they can use internally for meeting communication, but they also have us working in Switchboard code—building out some smaller features for actual users.” Tanner’s been working on some of their membership premium products.

So what’s it really like to intern for a PIE startup? In a fast paced startup environment, I figured that trying to keep up with it all would be a challenge.

“The challenges aren’t in actual code building,” Jennifer chimed in. “But this is the first time I’ve actually contributed to something that wasn’t built by me. I’m working with a new dev team that’s never existed in my career before. So I’d say the challenges are just getting used to that environment and figuring out where I fit in them.” The rest of the group seemed to echo her, almost chorusing around the theme PERSISTENCE. Every single one of them admitted to facing challenges, but they’d either ask questions until they resolved the issue, or they’d “google it” until they found the answer they were looking for.

According to Eric, cofounder of Read the Docs, it was an amazing experience for them too. “Not only have [the interns] been great people to work with, but it’s also been great helping people get into the field,” he said. “Being at PIE is neat because they get to see part of the startup process. They helped give feedback on our pitches and were good at finding issues only new people can find.”

So the next time you’re facing a challenge and trying to figure out how to kick ass, remember the Epicodus interns at PIE and perseverance. Catherine said it best: “there’s always going to be challenge, but this internship experience has shown me that each challenge can be tackled individually, and by taking that approach you find that you’re able to move forward every day—this is exciting.”

Interested to learn more about Epicodus? Visit their website to learn more.
Looking for a job or internship in Portland? Have you checked here? Portland Startups Switchboard.

Catherine and Justin with Read the Docs

Catherine and Justin // Read the Docs

Jennifer and Tanner with Switchboard

Tanner and Jennifer // Switchboard

Christian with Outdoor Project

Christian // Outdoor Project

Community, News

Video playlist from PIE Demo Day 2014

PIE demo day last Friday was a BLAST! Thanks to everyone who came to the theater, the simulcast and to those of you who tuned in via livestream. The Portland community never ceases to impress.

To those of you who were unable to join in on Friday…yes you’re late to the party, but the pitches are still as fresh as ever. Grab yourself a coffee and check out this pitch playlist from last Friday’s demo day.

See a pitch you liked? Give them an upvote on product hunt! And it’s never too late to join the conversation on Twitter with #PIEdemo.

Advice, Community

Presenting 101 — a few tips from Mike Pacchione

With demo day looming, PIE startups have already begun to experience both the joys of pitching and the pain of critical, straightforward feedback. We’ve received insight on the topic from a variety of mentors, and that’s just the beginning of the program’s pitch phase. Earlier this week we had storytelling expert, Mike Pacchione, share presentation basics with us.

But before we get into takeaways from his talk, check out this product pitch:

Interesting?! Errm…yeah, not really. Confusing/boring? Absolutely…which brings us to Mike’s first tip.

1. Understand that people are emotional

Mike shared with us that in order to connect with listeners, your pitch needs to go through the emotional part of the brain first (like a filter) before the listener will appreciate the logic behind it. I don’t know about you, but that pitch about the Turbo Encawhatever did NOT go through the emotional part of my brain so I never felt like I really needed to check in and even try to understand what was going on—plus, that dude was complicated. The problem is that the same thing happens with startups—most speak with abstract terms, speaking from logic to logic, and that’s where most communication falls short. Don’t start a pitch talking about your feature list, start it with a pull on emotions.

This, friends, is where stories come in…

2. Follow Duarte’s sparkline when structuring your story

Mike works for Duarte, a cool company that specializes in presentations and storytelling. (Psst—I even stumbled across his company profile.) Duarte’s CEO, Nancy Duarte, found a pattern among the best presentations, and when she drew it out, she came up with the following:

Duarte’s sparkline

Duarte's sparkline

The key here is that you’re trying to build tension throughout the entire presentation and you do this by consistently challenging what the audience is currently experiencing and believing. This outline can be mapped over Steve Jobs’ iPhone unveil in 2007 and over Martin Luther King Jr.’s “I have a dream” speech, and yet it’s one that you too can follow when you’re going through your presentation.

Let’s walk through what a startup pitch could look like using this same format:

a) What is…it like in the world today? As a tech startup, you might begin by painting a picture of the problems that people deal with in the absence of your product. What pain is your potential customer experiencing? This will not only help your listeners engage with your presentation on an emotional level, but it’ll keep them at the edge of their seat wondering how you’ll solve the problem and make everything better.

b) What could be…if your product was funded and introduced to the world? Show the contrast between a) what is and b) how much better the world is for those who use your product. This is an important moment. Do everything you can to help them understand how much of a difference this is from current circumstances.

c) What is…your competition doing? Your audience might have doubts in your product. They might wonder, “wait, isn’t someone already doing this? Is this the best solution on the market?” So follow them back through that. Show them where your competition is and where they fall short.

d) What could be…if you choose our product instead. (Here’s where you tell them why yours is better.)

Now that was the quick and dirty version and there are a couple more embellishments to it, so if you’re interested in learning more about the sparkline, here’s an excellent video from Nancy Duarte herself: Check out this video to learn more.

3. Practice a little bit every day.

If you’ve ever studied for a test the night before an exam, you’d know what it feels like to cram. It’s so much more effective (and I’m sure healthier) to understand your story, recraft it, and memorize it over the course of a few weeks than in a few hours. This tip seems obvious, but it’s not often put into practice. Devoting even just 30 minutes every day to constructing and practicing your pitch is much better than spending 4 hours the night before demo day. [Did you hear that startups?]

Practice starts today. “Let’s go, go, go.” [whistle blows]

Advice, Community, Mentors

Five questions with Duncan Davidson, Bullpen Capital

Duncan Davidson, Managing Director at Bullpen Capital, visited PIE today and shared valuable advice to all of us in the space. While all the startups asked him questions related to their specific businesses, I simply wanted to learn more of what it’s like to be on his side of the table. I didn’t pitch him, but I did ask him five simple questions.

What’s your most recent investment and what was the tipping point that convinced you to go all in with them?

Good question. [Yay, me! Starting off strong.] If I go through the last 5 deals we’ve done, they all have similar tipping points. Here’s a couple of those.

a) SpotHero, a parking company out of Chicago.

Parking is suddenly a hot category, and there’s a bunch of valet deals in San Francisco. SpotHero’s like Uber for parking spots, where they have deals with national garage chains.

We knew parking was big. We’ve watched parking for years. SpotHero was showing two things that was a tipping point.

i) They cut national contracts so they could go to almost any city with masses of available parking slots and parking garages (and with no extra work). They don’t have to go slug city by city.

ii) Their trajectory was taking off. Most of the other people we saw were struggling. We liked SpotHero’s trajectory.

b) StayClassy, a Saas for .org

Again, there are five other companies trying to do this, but it was theirs that had a trajectory that was taking off. That’s a common theme for us. We’re watching companies like they’re in a competitive horse race…when one takes off, that tips it.

What’s your process look like? How do you actually go about making that decision with the others in your firm?

Somebody comes in and pitches us. Everyone wants to show a demo and how cool their technology is. No, no. We don’t care about your demo. We want to see what’s your business, how well you’re doing, how fast you’re growing, and what’s your plan for the next year.

We start with a fact based–”here’s the reality of the business” approach. If you don’t get passed that filter we don’t take any more time on it.

Then the process after that is to have you answer a few very fundamental questions. We throw questions up at the person driving it. If they can knock the questions off, we go to the next five questions. When we’re out of your questions, we regroup and make the decision.

If we’re following a category (like parking), then we’re already well educated. So when a company walks in the door and shows they’re winning in that market, we can make a fast decision. If it’s a market we don’t know well, we either don’t do the deal or spend a lot of homework (and it’s a very slow process) until we get up to speed.

One of the mistakes venture people make is the grass is always greener. In a market we know very little about, everybody looks like a pretty girl. In a market we know well, everybody’s an ugly chuck. So we’re better off dealing with the ugly children than the pretty girls just because we have experience to tell us what they don’t know.

How do you interact with the founders after investing?

We have two types of founders. One type are experienced, they know what they’re doing. Our interactions with them are occassional and usually on-demand. If they need help, they call us.

We have another class which are newbies—in their first time through—and they just have to learn things. “How do you run a good executive meeting, how do you run a board, how do you deal with problems A, B, and C?” So in that case, we’re a lot more proactive in helping them through their problems. When we talk to the people that we deal with, they almost say the same thing:

“You’re not in our face like a lot of venture people, but you’re there when we need you.”

You’ve been on the other side of the table before–as the founder of a startup with a successful exit. What is the one thing startups should know when looking for investment?

You’ve heard of the three rules of real estate, right? Location, location, location.

For example, you’re McDonalds—where do you put a fast food joint? You find the best traffic pattern.You want a house? There’s a certain logic to why that house is the right house on the street and the next house is the wrong house. Location is everything.

Likewise, there’s four rules of venture capital. Ready?

Too early, too early, too early, too late.

The one thing to know, people, is timing. Timing is everything. All startups build on the shoulders of past technical development. There comes a moment where the technology comes together and coalesces–then new things can happen. If you’re too early, then it’s too expensive—you’ll never get there. If you’re too late, you’re not Whatsapp that’d already sprinted past you. So getting that timing right—when the coalesce of opportunity and technology hit—jumping on it fast is everything.

What do you know / have you heard much about the Portland landscape? What’s the startup culture look like to you compared to other places?

Startup culture is a type of culture that’s prevailing the world. I go to Australia, I go to London, I go to Japan, I go to Singapore and Turkey—you find that the startup culture is pretty much the same. They can read all the same blogs, like TechCrunch. They’re all taking hipster styles. There’s a commonality.

Thomas Friedman, from the New York Times, wrote a book called, “The World is Flat.” It’s actually not true. The world’s actually very spiky. But if you go from spike to spike, like Bangalore to Singapore and you skip over all the places in the middle, it all looks the same. It’s spiky, but there’s a consistency. So when you go from startup community to startup community, they’re similar all over the world.

I find Portland to be very similar. The people are technically really smart, they’re versed pretty much in what’s going on. Their understanding is pretty good. The bad part is that this is a very thin ecosystem—the depth of mentors, the depth of funding, the depth of other people challenging you.

There’s a reason why steel concentrated in Pittsburg and cars in Detroit. There’s a reason why Hollywood is where the studios are. And the reason is, there’s a certain economic force to get all the best people in the same place where they can deal with each other face to face. So people come to Silicon Valley wanting to be king of the hill and deal face to face with the best people they can. That sort of thing is almost impossible to replicate.

The main problem with Portland is you could have a very good startup culture, but you’re never going to match what’s down there. The answer is two fold:

a) either accept that and just do really cool companies (and maybe they get funded in Silicon Valley), or
b) find something unique in the Portland ecosystem that you can be the world class center of. You have some skills here to do that.

Seattle may become the cloud center because Amazon, Microsoft are there. I think of Portland as the new Tuscany. Dealing with different food ideas, craft coffees, beers (you’ve got the great Hops here). You’re in the magic latitude for hops and things like that. The point is: food. You might be the great advances in food if you want to be.

Or another is you have cheap energy here. You could become a great data-center / cloud place. You have economic advantages for that. If I were in the Portland community, I would try to figure out what we could do better than anybody else in the world, own that, and become the place that attracts people from all over the world for that because you have a great city, a great lifestyle, and a lot of educated people here. People want to live here.

Well, Portland…what do you say? The new Tuscany of the States? The data-center capital of the West? What makes Portland so unique? Let us know with a comment below.


Catching up with XOBXOB

Half way through the PIE class and everything is well underway. While some companies are working on their brand visuals, others are working on strategy. We had a stacks session yesterday and a 404 session coming up later today. It’s all heads down (exaggerated), learning from mentors, and bouncing ideas back and forth with investors.

Seating is clustered and arranged by company, and the solo founders cluster sits to my left. So I’ve rolled over to Bob from XOBXOB, to catch up with him, hear his story, and get his take on this whole PIE thing.

Bob, are you a Portland native?

I’ve always been in the Northwest. I grew up in Seattle and spent most of my life there. I was in Portland for a couple of years in the 80’s and actually loved it, but I ended up moving back to Seattle. It was like a game of ping-pong because I returned to Portland three years ago. (Don’t worry, I have no immediate plans to move back to Seattle.)

What got you started on XOBXOB?

I came down to Portland for a job, and there was a startup weekend—I had always wanted to do that. So I participated in a team that was in a similar space to XOBXOB. We ended up being one of the top teams in the end. The rest of the team decided to go their separate ways, but I realized that I had found my calling—that I should’ve been in the startup world decades ago.

I’ve really been fascinated with the Internet of Things space, even though that’s wildly hyped right now. I think it’s inevitable that our world is going to be fully connected. Just to be part of that emerging technology is fascinating, so I decided to continue on the same theme and created XOBXOB shortly after that.

How has coming into the PIE space impacted the way you work?

The biggest change is the availability of casual interaction with people. There have been lots of interesting serendipitous conversations. Even in co-working spaces they tend to be a little bit insular, but this space is so interactive, it’s a chance to be inspired by what other people are doing. It truly helps pull a solo founder out of themselves.

Tell me more about your PIE experience. Takeaways so far?

Any talk that has to do with messaging has been having a big impact on me. Because of my background, I tend to strive for clarity and brevity, but I was realizing after Jeff’s presentation that that is not compelling. A dry, concise description of my product is not going to make listeners enthusiastic about the potential in XOBXOB. That’s not what usually excites people about a product.

It’s like the difference between–”Stainless Steel Kitchen Knife” vs “Samurai Tomato Cutter.” You’ve got to give it a name and a personality.

If you think about it, you’re not buying a product, but you’re buying an experience with that product. So in my world, which is kind of technical, it’s really not about the features of my product, it’s about the experience they’re going to get. I keep hammering my head against that wall because that’s the real learning I need to take away from this. I know how to develop a product, and I know how to do design, but creating a compelling story is something I need to work on—and that’s great!

It’s kind of like you’re juggling, because at any given time—it’s all in the air. You just have to keep working on technology, domain names, how would you position this to a consumer right now—

Oh, pardon me. I should let you get back to juggling, then.


Alumni, Community

5 Questions with Vadio’s Elliot Swan

We recently shared news that PIE Alum Vadio, the platform that allows streaming music services to sync their audio with corresponding music videos, had raised $2 million.

Now we’re all aware of the fact that no company gets to $2 million without first facing a few challenges and tough decisions. So today we’ve caught up with Elliot Swan, cofounder of Vadio, and asked him to give us a glimpse into some of his experiences along the way.

1. When did you decide to jump ship and start your own company?

We had been working on Vadio part-time on the side and had a basic prototype put together that we would slowly continue to build and show around. I remember one evening suddenly coming to the realization that if I really wanted to see whether this thing would fly, I needed to take the full leap. And I knew I couldn’t live the rest of my life always wondering if something could have come of this had I only taken a risk and tried.

2. What was one of the biggest challenges entering this industry?

The music industry is notoriously complicated, so getting buy-in from all the relevant stakeholders took a lot of work. I see too many music startups try to brashly jump into the middle of the industry and claim they’re here to change the world without bothering to get to know people or understand how things work. It can be tough, but patience and humility go a long way.

3. How has being in the Portland community helped your company become what it is today?

Portland has a great startup community, and everybody wants to see everybody succeed. It’s amazing being able to walk down the street to a handful of other startups and ask for input.

4. What’s a small change you’ve recently made at Vadio that’s resulted in large positive results?

Anybody over here would tell you I love A/B tests. One we recently ran tested various wording options for the buttons that launch our players — we increased click-throughs by 10% just by adding a single word!

5. PIE’s 2014 class is already one-month in to the program. Having been through PIE and now a couple years out, what’s one piece of advice would you give to its participating founders?

For the next 3 months you will be constantly surrounded by super-smart people. Get to know all of them! You have no idea how valuable they will be to you and you will be to them over the years.

6. (Bonus question:) What’s your favorite music video?

Hands-down, Dance Thief by Con Bro Chill. It deserves way more views.

I had’t heard of Con Bro Chill before this, but the moment I started watching their music video, I knew it had PDX + weird written all over it. Portland—let’s bump up these views!


PIE teams compete in Hood to Coast

When teams from the PIE class aren’t pushing their products forward, they’re finding ways to continually push themselves. Last weekend, five athletes from PIE participated in an overnight long-distance relay race, Hood to Coast (which also happens to be one of the longest and largest relay races in the world*).

Just like building an amazing product, it didn’t come without some intense preparation and a hint of pre-performance anxiety.

“If you would have asked me a week ago if I would ever do this to myself again I would have responded with a very confident ‘NO!’ The training is rough, and more than anything I was bitter about how much time it took up in my day to day routine,” said Megan Fisher of BlkDot. “Typically I run 2–3 miles, tops. The thought of running 19 miles with a total of 45 min of sleep in 48 hours isn’t something I was fully confident that I could pull off. It’s pretty amazing to push yourself to limits you didn’t think you could reach.”

Krumplr’s James Stuckey is no beginner when it comes to races like this. “I think I’ve done it seven times,” he told me. “Right now, I’m training for the New York marathon in November and then the Paris marathon in April.”

In my mind, I was thinking—wait a minute. You’re a developer in a startup, you’re part of an accelerator, AND you’re a steadfast runner?

“I’m running about 30 miles / week, which is an interesting challenge with the whole startup thing going on.” – James Stuckey

Yes. He’s everything.

Kirsten ran on team #shrimpbird, and while she obviously wins at pretty much everything PIE related, I was curious to hear how she fared last weekend. Her thoughts were short and succinct:

“How was H2C? A man once tweeted, “pushing that last 5% harder than your competitor is so often the difference between success and failure.” So thats what I did. I won hood to coast and I won a van full of new friends.”

Sean from Switchboard who also ran on team #shrimpbird chimed in with his experience too. Grab a tissue.

“Hood to Coast isn’t really about running or the runners. It is about the volunteers. A wise man reminded me that “without them, we could not run.” Obviously we could run without them, but it wouldn’t be the same. This year team #shrimpbird was lucky to have the greatest volunteer in the history of the Hood to Coast – Boots. He went above and beyond the call of duty, driving all the way to Astoria after his shift at Exchange 24, just because he didn’t want to get in the way of the runners. There would be no team #shrimpbird without Boots.”

Congratulations Megan, James, Sean, Kirsten and Tara for still being able to make it to work by Monday morning. Also great job on the race—I hear that’s quite an accomplishment.

*Source: Wikipedia. (Don’t take my word for it.)


James ran the 9th leg at the Hood to Coast. Yes, he road-killed quite a few people.


Here, Boots is giving an inspirational speech the night before the race.


“Before my first run – I wasn’t so perky at the end, until someone handed me a beer.” –Megan

Hood to Coast runners

#HTCFAIL – these runners waited 20min to 2hrs for their vans to arrive due to poor planning at exchange 30.

Team Shrimpbird

Team #shrimpbird at the finish line (without Boots – he was bringing supplies from Portland for our post-race feast).

How was H2C? A wise man once tweeted "pushing that last 5% harder than your competitor is so often the difference between success and failure." So thats what I did. I won hood 2 coast and I won a van full of new friends. — Kirsten

Kirsten, after winning hood to coast.


Boom. Done. nuff said.