Episode 17 now available!

Ep 17 - Angela Damiani, CEO & Co-Founder, NEWaukee

​Building Belonging in Startup Communities​

Founders have almost nowhere to say "I don't know if this is going to work." Angela Damiani helped build a place where those conversations can happen and feel heard.

You can't express doubt in front of your team. They're looking to you to lead. You can't say it to your investors or your board. And you're probably not going to put it on LinkedIn.

Angela started NEWaukee 17 years ago as a social club hosting meetups before meetup.com was even a thing. Took five years to figure out the money side. Now they're a brand engagement agency doing around 200 productions in a six-month window, 40% of their work outside Wisconsin. They originated the Milwaukee Night Market, which went from a couple dozen people to tens of thousands.

But coming out of the pandemic, she felt lonely. Where are my people? One party in August 2021 became Midwest Founders Community. Four years later, it's a decentralized network of founders across the upper Midwest with twelve organizers and events in multiple cities. Almost no funding. All organic.

All that and more inside this episode

→ Listen to the Interview​

Topics discussed

• How NEWaukee went from free social club meetups to a brand engagement agency doing 200 productions in six months
• Why belonging requires intentional, repeated warm invitations, not just marketing
• The Milwaukee Night Market origin story: from a couple dozen people to 100,000 attendees
• Starting Midwest Founders Community after feeling lonely coming out of the pandemic
• Why MFC is structured as a network, not an organization, and why that distinction matters
• Founder loneliness: having almost nowhere to express doubt in front of your team, investors, or board
• Her critique that Wisconsin's investor class wants sure bets while founders are the ones taking real risks
• Social architecture: designing experiences that intercept people where they already are
• The long-term vision for MFC to have its own founder-led fund
• How a co-founder leaving after 15 years gave her clarity that she wasn't going anywhere

→ Listen to the Interview​

Key learnings

It Took Five Years to Figure Out the Business Model

NEWaukee started as a social club hosting meetups before Meetup.com was even a thing. Angela and the early team were insistent that their programs stay free, so they tried everything else to make money. Selling merch. Chasing sponsorships. Selling concessions. It was a rat race. Low price points, high turnover, corporations that didn't really care. About five years in, they finally asked: why don't we just treat this like an agency? Time plus materials. Bespoke experiences for clients who actually want to pay for them. That shift changed everything. Seventeen years later, they're doing around 200 productions in a six-month window.

Belonging Requires Repeated Warm Invitations

This one stuck with me. Angela's framework for creating belonging isn't complicated, but most organizations miss it. You need intentional, repeated, warm invitations. Not one email blast. Not a single social post. You have to keep reminding people: you're welcome here, this is for you, we want to see you, it doesn't matter that you missed the first one. That scratches something deep in all of us. Angela called it our fifth grade self. You want to be told you can sit at the table. That someone saved you a seat. Most marketing ignores this. It shouts into the void and hopes people show up. The antidote is personal outreach, over and over.

She Started Midwest Founders Community Because She Felt Lonely

Coming out of the pandemic, Angela realized she didn't know where her people were. She had spent years in the startup space through Nuance (NEWaukee's recruitment spinoff) and a B2B SaaS startup called Rivet. But when the world opened back up, she felt disconnected. The existing startup programming didn't appeal to her. So in August 2021, she and a few others hosted one party called Founder Fest. Founders telling stories, hanging out with other founders. She had hosted thousands of events by that point, but this one felt different. It felt like it was for her. People asked when the next one was. Four years later, MFC is a decentralized network of founders across the upper Midwest with twelve organizers and events in multiple cities.

MFC Is a Network, Not an Organization

This distinction matters. Angela has been very clear that Midwest Founders Community is not an organization. It's a network of founders. That framing keeps it neutral. No territory to defend. No institutional turf wars. Just a place for founders to come play together. The goal is simple: connect founders to community, capital, and customers. Different organizers bring different energy depending on what they're passionate about. Some focus on events. Some focus on mentorship. Some focus on investor intros. It evolves based on who's in the leadership seats at any given time.

Wisconsin's Investor Class Needs Higher Risk Tolerance

Angela didn't hold back on this one. Her critique: founders in Wisconsin are willing to take risks, but the investor class wants sure bets. Banks, VCs, angels, even enterprise customers. They all want precedent. They want to see it work somewhere else first. But every product or service that has changed the economy or our lives started as a fringe investment. If you want revolutionary technology or seismic cultural shifts, you need earlier bets on things that feel weird. Angela's long-term vision is for MFC to have its own fund because she doesn't have faith that existing institutions will lower their risk tolerance. She thinks it'll take founders who understand that risk to do it themselves.

The People Who Thrive Love the Chaos

NEWaukee's business is seasonal. Nobody wants to host anything in January. So from May to November, it's an onslaught. Back to back to back. Around 200 productions stacked on top of each other, many of them outside, braving the elements. The people who thrive at NEWaukee love that dynamism. Nothing feels routine. Every day feels new. Angela said they spend a lot of time as a team talking about how to maintain personal resilience through the heavy stretches. It's not for everyone. But for the right people, it's energizing.

Social Architecture Means Designing for Action

Angela used to push the term "social architecture" before landing on "experience design" as the easier sell. But the framework underneath is the same. You have to be intentional about the setting, the invitation, and all the parameters around whatever you're designing if you want people to take action. Her clients come to her with the same problem: their ideal customer doesn't care. They're not paying attention. But that's not an indictment of the brand. Nobody's paying attention to anything. We live in an overstimulated time. So the question becomes: what can we create that intercepts people where they already are, instead of shouting into the void trying to get them to come to us?

A Co-Founder Leaving Gave Her Clarity

A few years ago, one of Angela's longtime business partners wanted out. He was ready to be done. That moment forced her to ask herself a question she hadn't really sat with: is this still what I want? The answer was yes. NEWaukee is still her favorite platform to build from. The place where she feels the most creatively satisfied. She still loves leading the team. That clarity was a gift. She said founders don't always ask themselves that question enough. You get so fixated on grinding and solving problems that you forget to check in. For her, the answer was clear. She's not going anywhere.

You Can Choose Again

Angela started NEWaukee so young that she didn't have much previous work experience. What that gave her was a deep sense of agency. She feels like she's choosing everything in front of her. And if something comes up that she doesn't like anymore, she can choose again. She doesn't have to make the same choice. There are consequences, sure. Not every choice is a raving success. But after doing this for seventeen years, she knows she's in the driver's seat. Her job as the founder and leader is to stay clear-eyed about that.

Upcoming episodes 👀

• Justin Byers (Axio BioPharma)
• Jon Eckhardt (UW Madison School of Business)
• Joey Friedli (SpecterSight / Formerly Trashpoint)

What is the Startup Wisconsin Podcast?

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