Cover Story: Anastasia Williams

Your title, Entrepreneurial Community Navigator, isn’t a typical one. What does it actually mean, and what brought you into doing this work?

Most entrepreneurship support looks like a referral. Someone comes in with a problem, you hand them a resource, and you hope it sticks. What I’m trying to do is different: build an ecosystem where entrepreneurs are truly connected to each other, and where the region itself becomes a resource. The title reflects that. I’m not a business counselor or coach; I’m trying to build something.

I came to this work through an unexpected path. Before this role, I built and ran a marketing consultancy and membership community for entrepreneurs in the fiber arts industry – knitters, crocheters, yarn dyers: people running small creative businesses. It sounds niche (and it is), but the problems were universal: isolation, inconsistent income, and not knowing who else was navigating the same thing. I learned a lot about what it actually takes for entrepreneurs to support each other, rather than just coexist (or compete). When the opportunity came to translate that experience into place-based work in Siouxland, it felt like the correct next chapter.

You’re currently in the process of rebranding your organization as Startup Siouxland. What’s driving that change, and what does it say about where you’re going?

The old name, Iowa’s West Coast Initiative, made sense as a legal entity, but it didn’t say anything to attract the people we’re actually trying to reach. If an entrepreneur in Sioux City heard it, they’d have no idea it had anything to do with them. That’s a problem when your whole job is to be recognizable and strengthen networking in a community.

Startup Siouxland is a deliberate claim. Startup isn’t just for tech companies in San Francisco; it’s for anyone building something from scratch, whether that’s a restaurant, a trucking company, or a SaaS product. And Siouxland is the word people here already use for this region. It crosses state lines the way the actual community does. The name is an argument: that this region has a startup culture worth naming and worth showing up for. We’re just making it easier to find the door.

What does the entrepreneurial landscape in Siouxland actually need right now that it isn’t getting?

Hope! You may have heard the many self-deprecating jokes about Sioux City floating around, and while I am the first to applaud a great joke, I’ve also watched that humor do real damage. When a region habitually condescends to itself, it makes it harder for people to bet on themselves, start something meaningful, or simply stay here. 

What I think we need is a culture of belief, not just among entrepreneurs, but broadly. Because when someone launches a business here, and it works, that’s not just a business success. It’s evidence of something bigger. It changes what feels possible for the next person watching. That’s what I’m trying to build toward: a region where people feel this is a genuinely nourishing place to put down roots, and where that is visible in the businesses growing here. 

Building a business in a place like this is different from doing it in a major metro. What does the regional context actually change, and what advantages do you think people here underestimate?

There’s something I’ve noticed here that I haven’t found replicated anywhere else, and I’m going to say it plainly even though it sounds terribly cliche: the people are remarkable. I don’t mean that in a generic civic-pride way. I mean that when someone in this community is building something, the people around them show up. They make introductions without being asked. They share what they know and make a point to be present. In a larger metro, you have more of everything: more capital, more talent density, more press. But you’re also one of thousands of people trying to get noticed. Here, there’s still room to matter to people.

That’s an underrated advantage. Relationships move faster here. Trust builds faster. And for an entrepreneur, that’s not a small thing; that’s often the difference between getting traction and staying stuck.

What do you think has to change in mindset, in infrastructure, in culture for this region to reach its potential?

The mindset shift I keep coming back to is reciprocity, and I don’t mean networking, which often has a transactional undertone. I mean genuinely giving without expectation of receiving anything in return. This may look like sharing a contact, showing up to someone’s launch, telling a fellow business owner what worked and what didn’t, etc. This kind of culture typically doesn’t happen automatically, and in a region where people have sometimes felt like they’re competing for limited resources (scarcity mindset and all that), it can feel risky.

But the silo problem is real, and it’s costing us as a community. There are people doing incredible, overlapping work across this region who have never been in the same room. When that changes, like when an entrepreneur who has been working out of their basement finally joins a peer group and realizes they’ve been struggling with the same problem for two years that someone else has already cracked, that’s when the ecosystem starts to compound. And that’s what I’m trying to create the conditions for.

What’s something you’ve learned from the entrepreneurs in this region that genuinely surprised you or changed how you think?

I expected passivity. Not resistance exactly, but a kind of polite disengagement; people being too busy or guarded. What I got at my first Founders Table was enthusiasm, vulnerability, and an immediate request to meet more frequently. Nobody argued about their calendar. In fact, they asked if we could do it every week.

That changed everything for me. I came in thinking my job was to convince people that community was worth their time when, really, the desire was already there; it just hadn’t found a home yet. 

Can you share a story about an entrepreneur you’ve worked with that really shows what’s possible here?

There’s a dancewear designer I met at our BIG Challenge pitch competition last November who has become a really good example of what this ecosystem can do when it’s working.

She came in facing a capacity problem. She’s one person doing an extraordinarily specialized job, and when it became clear she was going to need help, the reflexive advice she kept getting was: get an intern. Find someone young and cheap. That advice wasn’t wrong exactly, but it wasn’t really seeing her business with a long-term lens.

I invited her in to talk. She ended up presenting at a First Friday Coffee event and getting feedback from the community. She came to a few Founders Table meetings at Winnie’s. Over time, she is starting to get a clearer picture of what her actual goals are, what her business really needs to become, and who she will need in her corner (literally and figuratively) to get there.

And this is what I want to build more of: opportunities where founders can have their assumptions challenged in a safe space and come out the other side seeing their businesses more clearly.

When entrepreneurs come to you, what do they usually think they need, and what do you find they actually need?

Almost everyone comes in thinking they need capital. A grant, a loan, an investor. And sometimes they’re right about that, but more often, what I find is that the capital question is premature. The thing underneath it is a business model that still has the founder doing literally e-v-e-r-y-t-h-i-n-g, with no real picture of what it looks like when they’re not.

There’s a version of entrepreneurship that’s really just self-employment in disguise, and there’s nothing wrong with that, but it’s important to know which one you’re building. A lot of my conversations end up being about helping founders see that distinction, and figure out what they actually want their business to become before they go looking for money to scale something they haven’t fully designed yet.

You run several types of gatherings: peer advisory sessions, networking events, and pitch feedback mornings. What are you actually trying to build through all of that?

It feels lame to say it, but I’m trying to build something that’s worth showing up to. We’re all crazy busy, we have very minimal attention spans, and there’s no shortage of networking events in the area where you stand around with (or sometimes without) a name tag and leave wondering why you came. I’m trying to avoid that.

All the formats that I’m building have a specific job to do. Our First Friday Coffee events are structured so that founders get constructive feedback in real time. Our Founders Tables (in Sioux City, Remsen, and Akron) are peer-advisory groups, rather than just a speaker series. My goal is for founders to leave with something they can actually move forward with. If they don’t… it feels like I’ve wasted their time and I’m pretty sensitive to that.

Underneath it all, what I’m really trying to build is density. Meaning that we have enough touchpoints, enough trust, and enough repeated contact between the right people that the ecosystem begins to build its own momentum. The events are just one mechanism in which we can do that.

What does success look like for this ecosystem in five years, not just for Startup Siouxland, but for the region?

Ten years feels more honest to me than five. Ecosystem building is slow work, and I’d rather under-promise and over-deliver.

But the vision is a region where if you have a business idea, you’re never alone. Where entrepreneurs are celebrated before they’ve proven themselves, supported by their neighbors, connected to mentors, and surrounded by a community actively rooting for their success.

On the ground, it looks like college students tangled up in the community rather than counting down the days until they can leave for somewhere bigger. It looks like the retired business owner in the same room as the twenty-two-year-old who just launched her first Etsy shop, next to the founder who just closed her first round. All of us (across this whole region) invested in the same community and believe it’s worth staying for.

For someone reading this who has an idea they haven’t acted on yet, what do you want them to walk away believing?

I want them to believe that it’s possible. That you can build a real business here, have a genuinely wonderful life here, and be surrounded by people who actually care about what you’re trying to do.

And I want them to know that the first step doesn’t have to be a business plan or a pitch deck (even if everyone says it is); it can simply be showing up somewhere. Come to a First Friday Coffee or join us for a Founders Table meeting at Winnie’s. Let people know what you’re building, and the rest will follow.

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