Episode 15 now available!

Ep 15 - Jillian Bichanich, Serial Entrepreneur

​Building Two Mission-Driven Startups​

"It shouldn't be this hard to do good in this world."

In this episode, we sit down with Jillian Bichanich, a Wisconsin-born founder and builder, to discuss how she is growing two mission-driven startups at the same time. Jillian shares her journey as the co-founder of Cubbi, an app designed to support families navigating disabilities, and as the founder of Pocketchange, a platform dedicated to helping consumers shop based on their values.

Jillian explains why following "what feels alive" has guided her entrepreneurial path and how facing rejection and chaos shaped her drive. We explore the unique partnership she shares with her co-founder and her experience of bootstrapping both companies. Jillian also reflects on the importance of aligning business with personal values, and her vision for revolutionizing industries with purpose-driven ventures.

→ Listen to the Interview​

The Startup Wisconsin Podcast is Presented by Valency Fund​

Topics discussed

• Running two mission-driven startups at the same time without burning out
• How Cubbi pivoted from a paid app to a free, sponsor-funded model after one brave bet
• Bootstrapping Pocketchange from branding to MVP on a near-zero budget
• The co-founder relationship that survived a year of rejection without a single fight
• Why Jillian left Silicon Valley and chose Madison for the values, not the venture capital
• Wisconsin's need for more real-time founder storytelling, not just post-success highlights
• Pocketchange's upcoming launch

→ Listen to the Interview​

Key learnings

Follow what feels alive, not a rigid schedule.

I asked Jillian how she manages two startups at once, expecting some disciplined time-blocking system. That's not how she operates. She follows what feels alive. Some days she works nearly 24 hours straight on Cubbi. Other days she's deep in Pocketchange. She doesn't force a fifty-fifty split because she doesn't believe that's how anything in life actually works.

What's interesting is that her approach isn't scattered. It's the opposite. She told me that when she forces things, whether the timing is wrong, the people aren't right, or she's not in the right headspace, it never works and she spirals wasting energy. She spent years as a self-described Class A perfectionist and people pleaser, valedictorian, five college degrees, doing everything she thought she was supposed to do. Running two companies broke her out of that mold.

For founders who think you have to pick one thing and go all-in or you're not serious: Jillian's experience is a counterpoint worth considering. The learnings from one company have helped her avoid problems in the other. Connections made through Cubbi have directly supported Pocketchange. When your startups share a common thread, they start to feel less like separate businesses and more like one ecosystem.

When traditional fundraising fails, stop waiting for permission.

Jillian and her co-founder Christine spent a year doing the grind. Pitch competitions. Investor meetings. They had the data, the mission, the team, the user feedback. And the doors didn't open. They got ghosted more often than they got actual nos.

So they stopped waiting. They found someone willing to give them $13,000 and built the MVP themselves. They pushed it out to parents. Mom influencers picked it up. They grew organically and eventually got traction in the UK because the problem Cubbi solves is global. Looking back, Jillian told me she's actually glad they didn't get that big check. The scrappy path forced them to figure things out in ways that made the company stronger than a well-funded version might have been.

This is a pattern I keep hearing from Wisconsin founders. The traditional fundraising path is brutal, especially for women, for mission-driven companies, for anyone who doesn't fit the typical investor mold. But the founders who find a way around it often end up more resilient because of it. That doesn't mean the funding gap isn't a problem. It absolutely is. But Jillian's story is proof that resourcefulness can be its own advantage.

A co-founder relationship without ego changes everything.

Jillian was pretty open about this: she and Christine have gone through the depths of hell building Cubbi. They've disagreed. But they've never fought. Their skill sets are completely different, which helps. Christine brings deep expertise in special education advocacy and has helped families win over $15 million in outplacement and support. Jillian handles tech, finance, and marketing.

But beyond the division of labor, what makes it work is the absence of ego. When Jillian told Christine she was starting Pocketchange, Christine didn't feel threatened. She asked, "How do I help? Do you want me to go get some press?" Jillian said it plainly: "The egos are not in the building."

That kind of partnership is rare, and Jillian knows it. For anyone evaluating a potential co-founder, this is the bar. Not just complementary skills, but the ability to genuinely celebrate each other's wins without keeping score.

Sponsor-based revenue can unlock your mission when bootstrapping hits a wall.

Cubbi started as a paid app because that was the only way to keep the lights on. But Jillian always wanted it to be free. The families using Cubbi are already navigating an expensive, exhausting system. Charging them felt wrong.

Last December, Jillian and Christine had a moment of clarity. They decided to put all their eggs in one basket and pursue corporate sponsors who genuinely cared about the mission. Not brands looking for a PR play, but companies whose VPs and executive teams actually wanted to use their resources to make a difference. A brand called Aerofoliology came on as their first major partner, and the entire model shifted. Cubbi became free for families.

Jillian described it as the first domino falling. Once that partnership landed, everything else started to move. For bootstrapped founders who are stuck on the revenue model question, this is worth studying. The answer might not be charging your users or chasing VC. It might be finding mission-aligned sponsors who see the partnership as a win-win.

Entrepreneurship is a mirror of your human essence, not a separate identity.

This one stuck with me. Jillian doesn't see business and personal life as two separate things you're trying to balance. She sees your business as an amplification of who you already are as a person. If you're a good person who shows up every day, pays attention to your customers, and cares about your mission, you're going to do well. Or at the very least, you're going to learn what you need for the next thing.

It sounds simple, but it's a fundamentally different lens than the "hustle culture" version of entrepreneurship. Jillian isn't performing founder life. She's just being herself, and the companies reflect that. It's worth asking yourself: does my business reflect who I actually am? If the answer is no, that might be the root of whatever friction you're feeling.

The wind tunnel of chaos is real, and you need someone to hold onto.

Jillian described a period in the Cubbi journey where she started to feel small. A million nos. Getting ghosted by investors. Wondering if she and Christine were crazy for believing in something no one else seemed to see. She called it a "wind tunnel of chaos," and the image is perfect. Everything around you is loud and disorienting, and you're just trying to hold on.

Thankfully, she had Christine. They held each other up when things got wobbly. For solo founders, this is a real warning. The wind tunnel will come. You need someone in your corner who believes in the mission when you're starting to doubt it. That could be a co-founder, a mentor, a peer group, even a podcast community. But you can't do it completely alone.

Madison's startup scene feels different because the doors are still open.

Jillian has worked in Silicon Valley. She's lived between Vegas and Redwood City. And she chose to come back to Wisconsin. Her reason: the values, the kindness, the approachability. In Madison, almost anyone will take your call. If something isn't a good fit, people introduce you to five others who might be.

She made a sharp observation: the tech and entrepreneurship landscape in other places has become "closed gate." She feels like things have shifted even from ten years ago. Madison still has that open door energy. It's not about Harvard degrees or being the seventh employee at Meta. It's about showing up, being resourceful, and helping each other out.

But Jillian also made a clear ask: Wisconsin needs more storytelling. There are incredible founders across the state doing amazing things, and not enough people know their stories. Everyone has the polished Instagram feed, but nobody talks about the hard stuff until they've already made it. Jillian wants more real-time honesty. The kind where a founder says, "Yesterday was one of the crappiest days I've had in business, but I showed up today and things turned around." That's the storytelling that helps other founders keep going.

Upcoming episodes 👀

• Russ From (Wayfi Wireless)
• Angela Damiani (Midwest Founders Community)
• Joey Friedli (Trashpoint)
• Justin Byers (Axio BioPharma)
• Jon Eckhardt (UW Madison School of Business)

What is the Startup Wisconsin Podcast?

It's a new show where you can learn about Wisconsin's growing tech scene. Hear the stories of startups, founders, investors, and the incredibly generous people making it happen every single day.

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jacob@startupwi.org