Ep. 32 | Navigating the Startup Landscape With Rick Turoczy  ## Metadata - Author: [[Overcommitted]] - Full Title: Ep. 32 | Navigating the Startup Landscape With Rick Turoczy - Category: #podcasts - URL: https://share.snipd.com/episode/8a47dbf6-353d-4cc6-8972-1f17c5093bfc ## Document Notes ## Highlights - **From Hobbyist Coder To Community Chronicler** - Rick traced his start from being a fifth-grade BASIC developer to writing about Portland startups and building community channels. - His blog unexpectedly became a hub that led to 18 years of chronicling and supporting the local startup scene. Transcript: Rick Turoczy Yeah, yeah. Happy to do it. Yeah. Portland, pretty accidental, quite frankly. It's like a series of happy accidents kind of thing. I used to be a very, very good developer in BASIC on a TRS-80 when I was like in fifth grade, back when you still had to press like play and record to save your files. But I continued to just kind of remain a hobbyist and involved in technology. But went to school, got a degree in English, wound up moving to Portland. And it was just really a random opportunity with a company that was hiring for an editor and copywriter that happened to be this thing called a startup. And I didn't know what a startup was or like that. I mean, I realized people started companies, but I didn't know that like you joined companies that were still at their formative phases. And my initial role kind of quickly transitioned from being a copywriter to being the guy who built pitch decks all day, every day for the founding team. And then continued to grow and learn about the organizations and kind of wound up following a few executives around to new startup gigs. So for about 12 years, I was just bouncing around from startup to startup, all venture funded, all tech companies here in Portland. And then, you know, thought I'd learned enough to do a company on my own. So tried that a couple of times and was just like, no, I'm not a founder. I'm like really good tactical support for visionary founders, but I'm not that visionary person. So kind of was spending a lot of time in the open source community. And because that's where a lot of the startup activity was coming out of. This is about 2005 or so. So it's at the point where open source is now being adopted by corporations and proprietary software pursuits. And at the same time, cloud infrastructure is becoming a real thing. So it's like this perfect storm of just like things that used to take us a room full of engineers and a room full of servers were suddenly being built in a matter of weeks or months by a handful Of developers. And I just found that super interesting. And so, again, didn't have enough technical acumen to contribute to any of those projects, but I was like, I'll just open source my marketing communication. And so I just started writing about what I saw happening in the community. And I blogged since the like previous century when you used to have to write code to put words on the internet, you know? And so I didn't expect it to be anything. I was just like, this will be my personal journal. Keep track of what's going on. And for whatever reason, it struck a chord. So people started sending me stuff and they're like, write about our startup, tell people about our event and all those kind of things. So that's really how it started. ([Time 0:01:18](https://share.snipd.com/snip/e8640ed0-978b-4872-8ec3-f1d8478ecf34)) - **Learning How To Learn Matters More Than Credentials** - Rick credits his English degree for teaching him how to learn broadly and confidently across topics. - Translating technical ideas into plain English proved crucial for communicating product and business value. Transcript: Rick Turoczy I think if I learned one thing there, it was actually how to learn, how to not be afraid of a new topic and how to embrace the learning around that topic. And that has probably been the thing that's most valuable. I think in that system, you wind up juggling a lot of topics and you're like, you know, inch deep, mile wide on any number of subjects, but have to pretend you're expert in them. And I feel that that works really well for especially early-stage startup founders who are kind of pretending they know what they're doing or trying to kind of fake their way through Stuff. And I still talk to my alma mater and other small liberal arts colleges, and they're kind of having a crisis of confidence right now. They're like, oh, we don't have a CS program, or like we're not teaching business acumen or those kind of things. And I'm always trying to remind them that like if you teach people how to learn effectively, then that's really, you know, an asset that people are going to be able to put to use regardless Of what they pursue. So I think it was really that. And it was one where you were almost forced out of your shell to explore new topics. Like that was part of the requirement was making yourself a well-rounded individual in terms of the educational perspective. So I think all of those things were really, really helped contribute. And then specifically from just an English perspective, like it's kind of like we've talked about a little bit, like just putting stuff in common English and not using acronyms or lingo Or like just being basic and explanatory can sometimes be hugely valuable in our industry. You know, people get really used to talking in code or lexicon that does not resonate with a regular individual. So I've found it's really helpful for me to be able to like convey that stuff in standard English, where it forces me to ask questions where I'm like, what do you mean by that? Like, I don't understand. How would I explain that to somebody else? Like, that's been helpful as well. ([Time 0:05:20](https://share.snipd.com/snip/b274009a-785e-4924-9828-bb7bf48f0e69)) - **Portland's 'Aggressive Humility' Shapes Startups** - Portland's culture blends high skill with low self-promotion, creating "aggressive humility." - That temperament yields well-rounded people who value life outside work and shape a distinct local startup identity. Transcript: Rick Turoczy Great question. Yeah, I was a huge fan of Portland. Like before I moved here, I was a dumb jock. Like I played sports all through school. And so even in high school, wound up over here playing sports quite often. And then in college, I was here a lot. And I really enjoyed my college experience. But, you know, when I graduated, most of my graduating class was moving to Seattle. And I was like, kind of done with college. I kind of need to move on to that next phase of my life. And so Seattle was close to Portland. That was one of the compelling things was it was close enough to kind of stay in touch with friends. And the other part was, you know, I'd grown up all over, but my high school years were in a small rural town. And so Portland had this compelling like small town-ish mentality, even though it had a larger metropolitan culture available to it. And I found that really compelling about the community. I think in the time that I've been here, so I moved here in the mid-90s, so 30 years, and in the time that I've been here, like, it's come into sharp relief that Portland has this really interesting, I refer to it as, like, aggressive humility. Like, the people here are really smart and really creative, but they don't self-promote. They don't brag about it. They're just kind of, oh, this is just the thing I do. I do this little thing. And then you find out later they're like the CEO of a billion dollar company or something. And it's like, I love that part about it. It's super charming. And I think it also lends to, because people aren't living to work, like they might be in the Bay Area where it's like work or your startup is the be all and end all. I think, you know, people have more pursuits and creative outlets and like they're interesting, well-rounded people. That always makes for compelling just communities and engagements and people you get the chance to chat with. I think Portland is a unique place on the West Coast, especially when it comes to technology. Like for somebody who's worked in tech in Portland for 30 years, I'm not sure it's really a tech town. Like I think we've kind of made a run at it a few times, but that might not be the most compelling ecosystem for us. And I think, you know, as the West Coast culture has kind of become more homogenous, like 80% of the culture on the West Coast is the same regardless of where you're located physically. If you're in San Diego or LA or Seattle or Portland, like you get good food, you have access to the outdoors, like all that kind of stuff. And it tends to be those more specific aspects of the community that tend to attract people. And so I think there's almost a selection bias for Portland. Like if you're really hard charging startup type, you're probably going to gravitate to the Bay Area. If you're more business corporate type, there may be some things that are compelling about Seattle. And so I think we find that people, we wind up with a kind of similar group of people because of that selection bias. And that can be both good and bad for a number of reasons. But it also feels like other regions on the West Coast specifically have, they've been defined already. And Portland still feels like it's trying to figure out exactly what it is or what it wants to be. And I find that compelling as well and interesting. Like we haven't really owned our own narrative. We don't really have a brand unless it's defined by somebody else. And so it's kind of a constant creative work in progress. ([Time 0:08:02](https://share.snipd.com/snip/9ca8535f-b4a6-496d-95a9-3c149e8bbcd0)) - **Experiment Early To Find Your Founder Fit** - Experiment quickly and accept failure to discover where your strengths and gaps lie. - Try roles early to decide if you want to build a product or run a company before committing fully. Transcript: Rick Turoczy Very interesting. Yes, I have learned from my career. Like one of those, you know, you sometimes have those random like things that just kind of stick with you forever and just kind of become a touch point, no matter how minuscule they may Seem. Like I can still remember, like I was cleaning out my garage or something and came across a brochure. We used to do brochures. They were printed pieces of collateral that people would hold in their hand before we did all the digital things. And like, it was a brochure I'd worked months and months and months on and really been like, you know, painstaking work, trying to make it the perfect document possible. And I remember opening it up and seeing a typo on the first page. And it was just like one of those things. It was like, if I was so obsessive about this and that still got by me, then most people aren't noticing most mistakes we're making most of the time. And that really inspired me to, like, people come back sometimes and they're like, you told me to do this and it worked really well. So I kind of stick with it. It's like, just half-ass everything. Like, don't be so like, I have to be all in. I have to be perfect. I have to do whatever. Like, it's really been this, like, if you want to do something, don't worry about going all in, just try it. And you need to try things and experiment to figure out where your skills or expertise actually exists. And with founders, you kind of have to push them to do that because they're expected to do everything. Like I think one of your recent conversations, the founder was talking about, like, I knew how to build product, but I didn't realize I had to do all these other things to be a founder. And you're never going to be perfect at all of those things. You're never going to be an expert at all of those things, but you do want to try them or at least risk failing at them to figure out where the gaps in your knowledge are, where you can excel For the company. You know, I have conversations with founders all the time where I'm, especially technical founders, where I'm like, are you sure you want to be the CEO of this? Like, do you want to just lead product or be the CTO maybe? And they're like, no, no, I totally want to be the CEO. I'm like, okay, but you don't get to do any of the fun stuff anymore. You have to do all that other stuff and somebody else is going to be building product and doing the things that you enjoy. So, so much for startups and founders, apart from that experimentation, is helping them have the courage to fail so they can figure out where they can be successful or to have them say, Like, this isn't what I thought it was. Like, for me as a founder, it took years and years for me to figure out that I didn't want to be a founder. If I can help somebody else figure that out in three to six months, everybody wins because that person's really focused on what they want to be doing and what they should be doing. But they would never know that if they didn't have the opportunity to try it, to experiment with what they were doing and likely potentially fail because that's mostly what startups Do. Like they just don't. So there's so many moving parts. ([Time 0:15:20](https://share.snipd.com/snip/002d013e-91d8-4288-9664-324d6a332e06)) - **How PIE Evolved Through Iteration** - PIE began as a co-working space and evolved into an accelerator that pairs startups with established organizations. - They iterated across sectors like consumer products, AR/VR, and corporate innovation to find mutually valuable collaborations. Transcript: Rick Turoczy Pi, at its very most basic, is just this ongoing experiment to figure out how more established organizations like a corporation or an educational institution or maybe a government Entity can effectively collaborate with startups and startup founders for mutual benefit. So we don't want it to be a one-way thing. We want the established entity to be deriving value from it. We want the startups to be deriving value from it. We've been working on it for about 15 years. It started as a co-working space. And then really, we kind of got into the situation where co-working is a hard model to begin with. And what we started to realize was if you're a co-working space, you have to take anybody who can pay for a desk, whether they're contributing to community or not. And then we were also encountering people who are like really great stewards of community who just couldn't afford co-working. And we're like, what are we doing here? This isn't the right model. And so we kind of pivoted into the startup accelerator model, which people throw that term around. It's basically just mentorship for startup founders over a very short period of time, usually accompanied with some investment of capital of some sort. And so we just continued to kind of iterate on that. We copied a few other models and kind of mucked around and put something together and then continued to try different things. We originally started in SaaS mobile kind of stuff. The only thing that remained consistent year over year then was we really felt the shared workspace was valuable. We felt it was valuable to have founders around other founders for both peer support as well as just like emotional support. And then we learned a lot during the pandemic where like this model does not work terribly well if it's not in a physical space. Like the space itself does a lot of work that we didn't even realize it was doing. And we've also experimented not only with different organizations, but different participants, different types of products. So our original partner was Widening Kennedy. If people don't know who Widening Kennedy is, they're a global advertising firm that they came up with Just Do It. They're like the old spice guy and Coca-Cola polar bears and like that kind of stuff. And they really wanted to just learn more about innovation and technology. That's why they began the pursuit. We did a great program with Daimler. Daimler Trucks has a corporate presence here. We helped them build an external and internal accelerator for employees to address problems that were occurring in the corporation and use kind of startup thinking to solve things Like that. And we experimented with like digital storytelling. So like what back then was AR, VR, XR kind of stuff, video game things. We have a partnership with Autodesk, which has a major Portland presence around manufacturing or founders who are building a physical object, ideally one with some electronics related To it, because they like figuring out both the circuit boards and the housing. And so that was what motivated them to engage in that. And then for people who aren't familiar with Portland, one of my co-founders always refers to Oregon as the Silicon Valley of consumer products. We have more like footwear and apparel and food and beverage and coffee and blah, blah going on here than probably anywhere else on earth. And so we took the opportunity to focus on some consumer products companies and test the accelerator model with them as well. So it's really like, it's just a learning platform. It's a way of delivering education and mentorship. ([Time 0:19:17](https://share.snipd.com/snip/fe156a5d-4cef-4a04-ba2b-db7d429d47b0)) - **Build Practical Support Into Founder Programs** - Create safe peer spaces and active check-ins to surface founder burnout early. - Use small supports (meals, babysitters, funds) to restore founders' capacity and prevent collapse. Transcript: Rick Turoczy Brad's cohort, we actually, it was our first one. And we actually encountered this issue where the company that Brad would eventually go to work for was like the superstar in that class. And they would show up to every like group meeting and they'd be like, oh, we just raised millions of dollars and we just launched this product. We just did this. And you'd see the rest of the class just go like everybody be like, I didn't get anything done this week. So we had to like that taught us that it's like you have to put some guardrails in to say we love it if you're doing great. But this is really about sharing your challenges and where you're finding difficulties. And we don't want we dismiss that progress, but there should always be someplace where we're looking to improve or work on things. And we continue to kind of refine that model. A lot of my work as kind of just like herding cats, it tends to be like looking towards that negative space of being like, you've been checked out for two weeks. What's going on? Like, do we like, do we need to do something to help you? Do we, you know, we had a little slush fund where it was like anybody on staff could use it if they found a founder was struggling. Like we had a founder who was like feeling he'd been working way too much, was burnt out. We were sensing that like it just wasn't healthy. And so we were like, we're going to pay for a babysitter and dinner. Go do that. Stop thinking about the startup and go do the thing. You know, just being open and present to like these are people trying to build things and how do we support those people? I had also pursued, speaking of failures, I had also pursued something unsuccessfully that I still think has merit. Aggregate services in benefit of the startup. So they'll be like, oh, here's a legal team. Here's an accounting team. Here's a design team. Like these are all the resources that you can use. We had pursued a grant to do the same thing with a professional therapist. Like we wanted, we wanted to see like, if you brought therapy into this environment, would that make for more successful, resilient, kind of formidable founders and companies? We can never get anybody to quite buy off on the grant. Like, we got positive feedback. We just couldn't finance it. But I was always curious to see also, like, which of therapeutic environment would be best for a founder. Like is it group therapy? Is it individual? Is it like what? So we wanted to test some of that stuff too. Taking care of themselves physically, mentally, emotionally, they have a much better chance of being successful at what they want to do, but they have to have the time to do that. That can't be forcing them to do all the things. You have to figure out how to structure that the right way. But it is, it's the most corrosive, like, I don't know why anybody does it. Being a founder is awful. Like it's, it's the worst thing you could do to yourself. ([Time 0:25:24](https://share.snipd.com/snip/b831139d-a6a9-490f-b257-39d44decd51f)) - **Cohort Dynamics Taught Guardrails Are Needed** - A standout cohort member dominated meetings with success updates, which discouraged peers from sharing struggles. - That taught PIE to enforce norms emphasizing vulnerability and learning, not constant wins. Transcript: Rick Turoczy We just did this. And you'd see the rest of the class just go like everybody be like, I didn't get anything done this week. So we had to like that taught us that it's like you have to put some guardrails in to say we love it if you're doing great. But this is really about sharing your challenges and where you're finding difficulties. And we don't want we dismiss that progress, but there should always be someplace where we're looking to improve or work on things. And we continue to kind of refine that model. ([Time 0:25:44](https://share.snipd.com/snip/64373bbf-27ba-4c8b-82c2-ef74c07bde56)) - **Decide If You Want A Product Or A Company** - Ask whether you want a product to exist or to build a company; prioritize the business if you aim to be a founder. - Be willing to kill a beloved product if it's necessary for the company's survival. Transcript: Rick Turoczy Like just do that., if you start a company to do it, then you're building a whole other thing in addition to building a product. So one of the things we always ask founders is like, do you want this product to exist? Or are you trying to build a company? And the qualifying question there is, let's say we have to kill that product in order for this company to survive. Are you willing to kill that product or is that just what you really want in the world? And that can be one of the things that helps people figure out if they're truly on kind of a startup founder trajectory, because startup founders want to build a business and they will Figure out products that make that business successful, but the business is more important than the product. And then unfortunately, if they take that venture capital path, then making money becomes more the focus than even the business or the product. ([Time 0:30:40](https://share.snipd.com/snip/5fce480d-cab3-4cbc-b79a-e9cddc9f01d9)) - **Easier Building Makes Selling Harder** - Building products is far easier today, but selling them remains the persistent bottleneck. - Lower engineering barriers shift friction to distribution, timing, and market fit. Transcript: Rick Turoczy Yeah, mostly cultural, I guess, is the best way to put it. Like when I started in startups, even into the early pie days, you were still crazy to be starting a company like people would be like why don't you just go get a job like why are you starting A thing that's dumb and so like today it's like well today every kid coming up through the system wants to be a creator or youtuber or whatever but startups are part of popular culture. And we've had like whatever, 15 years of Shark Tank, like constantly feeding people that, oh, you should start a company and do a thing. And I think that's become a whole new challenge because of that mythology. So, you know, when we started, it was hard because nobody thought you should be doing that. And now we exist in a world where everybody's like, well, if you're not doing a startup or a side project, are you even really doing anything? And so there have been a lot more people in the industry and a lot more folks struggling with things than they did in the past. I think, you know, the other part of it is, and I don't want, this is not meant to be negative or dismissive, like, it's a lot easier to build a product these days than it was before. And so that can also be something that kind of leads to issues and problems. I mean, when somebody even like with my lack of technical acumen can spend some time with Claude or ChatGPT and code up enough of a thing that works well enough to do the thing I need it to Do, like that's also kind of almost a garbage in, garbage out problem. It's like because the barrier is so low, people may think they have an idea that's viable that's not really an idea that's viable. And so the bigger challenges now are educational, dissuading people from taking the track they think they need to take because of what they've heard, because of what goes on in the industry. It's still just, it's still, no matter what people say, it's still hard to raise money. It's still hard to build a company. It's still hard to build a good product. And I heard something really good from a venture capitalist here in town named Diane Freeman, who works at Voyager. The other day, thought it was a really important point. Like, no matter how easy it gets to build product, raise money, what have you, you still have to sell the thing and somebody still has to buy the thing. So like that, that remains like a huge friction point that will remain hard forever, even if it's, you know, giving your agent your credit card so it can go buy something, it still needs To be buying something and somebody still needs to be selling it. So it's like there's just all kinds of facets where one part of it as one part seems to get easier, the other part seems to get harder and it always kind of balances out. There's always something hard. There's always something that's slightly easier. ([Time 0:32:53](https://share.snipd.com/snip/30b51167-3d4e-4067-b69f-077e31a0c888)) - **Portland Picks: Books, Science, Coffee** - Rick recommends Powell's bookstore and OMSI as quintessential Portland experiences. - He also highlights Deadstock coffee for its cultural crossover between shoes, design, and community. Transcript: Rick Turoczy Second, seconding Powell's. Powell's is just like, it's a full city block of books, like all used. I think they sell some new, but it's a used bookstore. So definitely that. If you come here with kids, go to OMSI. Like most, it's the Oregon Museum of Science and Industry. And I think in most cities, the museum that's central to the city is an art museum. And for us, it's really OMSI, which is experimental and fun. But to pick the, you can't go wrong. Every five blocks is a new neighborhood in Portland full of great restaurants and coffee shops and those kinds of things. So it's really hard for me to pick a favorite, but I would say the quintessential coffee shop for Portland right now for me is Deadstock because it's a sneaker themed coffee shop that Was started by a former Nike shoe engineer. And it's just really one of those where it's such an interesting cross-section of a town that tends to be very siloed in its creative pursuits. Like tons of great food people, but they don't necessarily cross over with the shoe people or they don't cross over with the artists or whatever. And so it's just always nice to see that those two things collide in that place. And they're always everybody from like, you run into elected officials to like, famous people who just happen to be in there. It's just a really interesting place. ([Time 0:40:03](https://share.snipd.com/snip/923b8f7c-5a89-4460-a6db-8f25b72b3eb6))