Startup Wisconsin Podcast

Matt Howard started EatStreet as a junior at UW-Madison in 2010. Back then, ordering delivery meant calling a restaurant, reading your credit card number over the phone, and, in EatStreet’s case, sending the order to the restaurant by fax machine.

He bootstrapped the company for two and a half years before raising outside capital, eventually bringing in more than $55 million and growing EatStreet to 350 full-time employees and 4,000 delivery drivers. But as competitors raised billions and poured money into the same markets, Matt found himself navigating a very different company than the one he started.

Matt joins guest host Laura Strong to talk about building EatStreet from a college startup into a major food delivery company, learning how to raise and deploy venture capital, making a high-stakes bet on last-mile delivery, competing against heavily funded rivals, deciding when it was time to leave the company he built, and how those lessons now shape his work helping early-stage founders through SeriesUp.

How Matt bootstrapped EatStreet before learning venture capital was even an option
Why different stages of a startup require different people, leadership styles, and ways of operating
What Matt learned about founder identity, letting go, and building the next generation of Wisconsin startups

(00:00) Introduction
(02:00) Starting EatStreet as a UW-Madison student
(04:57) Growing up in rural Wisconsin and choosing Madison
(08:05) What Matt learned scaling EatStreet
(10:02) Bootstrapping before discovering venture capital
(12:41) Raising on the founder and the story, not just the numbers
(15:09) What Matt looks for in early-stage founders
(17:03) What EatStreet's first institutional round unlocked
(20:09) Using data to scale into new markets
(21:07) The decision to enter last-mile delivery
(23:40) Going against the board on a company-defining bet
(24:48) Why teams need to change as companies grow
(28:31) Competing when rivals raised billions
(31:18) Knowing when it was time to leave EatStreet
(33:05) Building SeriesUp around early-stage founders
(38:55) Why leaving a company is not the same as failing
(43:41) The mentors who shaped Matt's founder journey
(47:33) What made building EatStreet in Madison special
(49:07) Wisconsin's challenge with venture capital
(56:06) Why passion has to be paired with execution

Connect with Matt Howard: https://www.linkedin.com/in/matt-howard-64492935/
Check out SeriesUp Consulting: https://seriesup.com/

Valency Fund

Flexible funding solutions designed for sustainable growth of Wisconsin companies.

Learn more at https://www.valencyfund.com/

Subscribe to the Startup Wisconsin Newsletter

https://www.startupwi.org/

Upcoming Tech and Startup Events in Wisconsin (400+ every year)

https://www.startupwi.org/events

Follow us on LinkedIn

https://www.linkedin.com/company/startup-wisconsin/

Connect with Jacob Miller:

https://www.linkedin.com/in/kineticbear

Interested in being a guest? Reach out!

[email protected]

Startup Wisconsin's mission is to connect, educate, inspire, and grow tech startup communities across the state, not just during events, but year-round. This podcast is part of that vision, creating deeper connections and sharing the knowledge that helps Wisconsin's startup ecosystem thrive.

This podcast is made by your friends at Headway.

https://www.headway.io

Justin Beck started PerBlue with his lab partner Andrew Hanson while they were students at UW-Madison. They set out to build a location-based game for the first touchscreen phones. He turned down job offers from Microsoft and Google to keep the team together, and the company grew into Parallel Kingdom, DragonSoul, and Disney Heroes. Along the way, PerBlue turned down an acquisition offer from Zynga, raised venture capital, and sold DragonSoul while keeping the company and its team intact.

Justin later founded Playback Rewards, a platform that pays players for playing mobile games. He ran into a venture market that was focused almost entirely on AI.

Justin joins guest host Laura Strong of Valency Fund to talk about how he approaches risk, what it takes to bootstrap and raise capital, why selling a game instead of the company worked out, what he would change about scaling too long, and how AI is changing who can start a company and how much it costs.

Tune in to learn:

• Why a mentor's advice that a job offer will still be there later helped Justin walk away from Microsoft and Google
• How Justin gave investors an exit and kept the PerBlue team together by selling one game and spinning out a new company
• Why Justin would scale down earlier if he did it again, and what AI means for early-stage founders and the next chapter of capital

Jump into the conversation:

(00:00) Introduction
(01:28) Starting out at UW and the company that didn't make it
(03:17) How PerBlue began in an electronics lab
(06:15) Funding the early days with a Google grant and family money
(09:27) Turning down Microsoft and Google to keep the team together
(12:57) Why risk is a moment in time
(15:37) The Zynga offer and raising a seed round instead
(19:25) How DragonSoul led to selling the game, not the company
(24:52) Building Disney Heroes
(28:52) Starting Playback Rewards and raising in the AI era
(31:53) Thinking flexibly about the capital stack
(35:28) Getting further with less capital
(38:59) How to win when everyone is using AI
(43:11) Which role makes Justin the happiest
(45:15) Running boards and building trust with investors
(50:57) Why time kills deals
(52:04) Book recommendations for founders

Read the full episode recap: startupwi.org

Connect with Justin Beck: LinkedIn
Check out PerBlue: perblue.com
Connect with Laura Strong: LinkedIn
Follow us on LinkedIn: Startup Wisconsin
Subscribe to the Startup Wisconsin Newsletter: startupwi.org

Valency Fund

Flexible funding solutions designed for sustainable growth of Wisconsin companies.

Learn more at https://www.valencyfund.com/

Subscribe to the Startup Wisconsin Newsletter

https://www.startupwi.org/

Upcoming Tech and Startup Events in Wisconsin (400+ every year)

https://www.startupwi.org/events

Follow us on LinkedIn

https://www.linkedin.com/company/startup-wisconsin/

Connect with Jacob Miller:

https://www.linkedin.com/in/kineticbear

Interested in being a guest? Reach out!

[email protected]

Startup Wisconsin's mission is to connect, educate, inspire, and grow tech startup communities across the state, not just during events, but year-round. This podcast is part of that vision, creating deeper connections and sharing the knowledge that helps Wisconsin's startup ecosystem thrive.

This podcast is made by your friends at Headway.

https://www.headway.io

Rukmini Banerjee spent her career inside companies like CUNA Mutual, Fetch Rewards, and Vouch Insurance. Starting a company was never part of the plan.

Her parents were living with her older sister in Melbourne, her in-laws were in India, and family members were scattered around the world. Rukmini started seeing how much of the day-to-day burden was falling on the person physically closest to her parents.

Rukmini joins Jacob Miller to talk about the moment that pushed her into entrepreneurship, what families actually need when coordinating care, the feature users surprised her by loving, building CuroNow with co-founder Pat Setji, going through Creative Destruction Lab Wisconsin, and why Madison’s startup community has made such a difference.

How Rukmini turned a personal caregiving challenge into the foundation for CuroNow

(00:00) Introduction

Connect with Rukmini Banerjee: https://www.linkedin.com/in/rukminibanerjee/   

Valency Fund

Flexible funding solutions designed for sustainable growth of Wisconsin companies.

Learn more at https://www.valencyfund.com/

Subscribe to the Startup Wisconsin Newsletter

https://www.startupwi.org/

Upcoming Tech and Startup Events in Wisconsin (400+ every year)

https://www.startupwi.org/events

Follow us on LinkedIn

https://www.linkedin.com/company/startup-wisconsin/

Connect with Jacob Miller:

https://www.linkedin.com/in/kineticbear

Interested in being a guest? Reach out!

[email protected]

Startup Wisconsin's mission is to connect, educate, inspire, and grow tech startup communities across the state, not just during events, but year-round. This podcast is part of that vision, creating deeper connections and sharing the knowledge that helps Wisconsin's startup ecosystem thrive.

This podcast is made by your friends at Headway.

https://www.headway.io

Kai Heineman puts 50% of her startup evaluation on the team.

That may sound surprising when the product is what customers ultimately buy. But in the early stages of a company, the team has to navigate uncertainty, raise money, find customers, change direction, and keep showing up when progress gets difficult.

Kai is a venture manager at Creative Destruction Lab at the University of Wisconsin–Madison, where she leads the health and wellness stream. CDL works with seed-stage science and technology companies through a nonprofit model with no fees, no equity, and no IP requirements.

In this conversation, Kai explains how CDL works, why the program focuses founders on three critical objectives at a time, and what separates founders who thrive from those who struggle.

Jacob and Kai also discuss why CDL chose Wisconsin, what visiting founders discover when they come to Madison, and how the program connects global startups with local mentors, investors, healthcare organizations, and UW–Madison students.

(00:00) Introduction

(02:20) From biology student to startup builder

(04:33) How Creative Destruction Lab supports startups

(06:45) Mentorship expands from local to global

(08:30) Inside CDL’s intensive session days

(10:52) Why founders focus on three objectives

(13:26) Why CDL launched in Wisconsin

(15:04) How corporate partners support CDL

(16:11) CDL recruits scalable startups worldwide

(17:34) Why visiting founders embrace Madison

(19:09) How Droxy scaled through CDL

(20:32) Connecting UW students with global startups

(22:33) Why seed-stage startups fit CDL

(24:17) Why strong teams make successful startups

(28:05) How to join the CDL community

(29:35) Apply by July 24 for CDL

(30:39) Why founder community determines success

Connect with Kai Heineman: https://www.linkedin.com/in/kai-heineman/  

Check out Creative Destruction Lab: http://www.creativedestructionlab.com/  

Valency Fund

Flexible funding solutions designed for sustainable growth of Wisconsin companies.

Learn more at https://www.valencyfund.com/

Subscribe to the Startup Wisconsin Newsletter

https://www.startupwi.org/

Upcoming Tech and Startup Events in Wisconsin (400+ every year)

https://www.startupwi.org/events

Follow us on LinkedIn

https://www.linkedin.com/company/startup-wisconsin/

Connect with Jacob Miller:

https://www.linkedin.com/in/kineticbear

Interested in being a guest? Reach out!

[email protected]

Startup Wisconsin's mission is to connect, educate, inspire, and grow tech startup communities across the state, not just during events, but year-round. This podcast is part of that vision, creating deeper connections and sharing the knowledge that helps Wisconsin's startup ecosystem thrive.

This podcast is made by your friends at Headway.

https://www.headway.io

“If you're a founder without any sort of Forward BIOLABS, you have some experiments that you need to do. And without anything like this, they have to think, ‘Well, how am I gonna get that done?’”

Jessica reflects on her 20 plus years of experience moving academic discoveries into the marketplace and explains why biotech founders face such high barriers to entry. From expensive lab equipment, safety requirements, and regulatory testing to complex logistics, she breaks down how shared lab space and on-site support can save startups significant time and cost. She also shares how Forward BIOLABS began as a “napkin scratch” idea that required fundraising, stakeholder alignment, and quick validation through early tenant companies.

We also discuss how Forward BIOLABS fits into Wisconsin’s broader innovation ecosystem, including partnerships across universities, nonprofits, and industry. Jessica highlights collaboration with organizations like WARF and WiCell, the strength of biotech talent in Madison, and why many companies choose to stay in Wisconsin as they scale rather than relocate to coastal hubs. She also shares examples like Elephas Bio, which grew from early-stage tenancy into a major personalized medicine company.

Why biotech startups struggle with space, equipment, and regulatory complexity

(00:00) Introduction

Connect with Jessica Martin Eckerly: https://www.linkedin.com/in/eckerlyjm/

Valency Fund

Flexible funding solutions designed for sustainable growth of Wisconsin companies.

Learn more at https://www.valencyfund.com/

Subscribe to the Startup Wisconsin Newsletter

https://www.startupwi.org/

Upcoming Tech and Startup Events in Wisconsin (400+ every year)

https://www.startupwi.org/events

Follow us on LinkedIn

https://www.linkedin.com/company/startup-wisconsin/

Connect with Jacob Miller:

https://www.linkedin.com/in/kineticbear

Interested in being a guest? Reach out!

[email protected]

Startup Wisconsin's mission is to connect, educate, inspire, and grow tech startup communities across the state, not just during events, but year-round. This podcast is part of that vision, creating deeper connections and sharing the knowledge that helps Wisconsin's startup ecosystem thrive.

This podcast is made by your friends at Headway.

https://www.headway.io

“I cannot wait till like I'm somewhere up in Northern Wisconsin, I stop and open the door, and there's the founder of a company that came from this process.”

In this episode, I sit down with Jon Eckhardt, Pyle Bascom Professor at the Wisconsin School of Business, to explore the university’s push to become more founder forward. Jon shares why entrepreneurship should be treated as a true career path, with support systems similar to medicine, law, and engineering.

Jon reflects on the experiences that shaped his thinking, from serving in the Army to co-founding gener8tor and studying entrepreneurship through data science. He explains how UW-Madison uncovered startup activity happening across nearly every discipline on campus, proving entrepreneurial talent exists far beyond business school.

We also discuss the origins of tech transfer at Wisconsin, the limits of traditional commercialization models, and why the future of entrepreneurship support should focus more on cultivating founders themselves. Jon shares how lower startup costs, shifting capital dynamics, and stronger statewide collaboration could help position Wisconsin as a leader in innovation-driven entrepreneurship.

(00:00) Introduction

(02:24) Army lessons that shaped Jon’s leadership

(03:32) Using data science to study startups

(04:24) Building gener8tor and mentoring founders

(06:06) Discovering hidden founders across campus

(09:33) Thousands of students have startup ideas

(13:52) How tech transfer started at Wisconsin

(17:01) Why founders matter more than patents

(20:39) Treating entrepreneurship as a career path

(23:43) Exposing students to entrepreneurship early

(27:54) Measuring startup success at UW-Madison

(33:58) Connecting student founders across Wisconsin

(39:34) Why startup costs are collapsing today

(45:06) The truth about bootstrapping startups

(52:04) What comes next for founder forward initiatives

Connect with Jon Eckhardt: https://www.linkedin.com/in/joneckhardt/

Check out University of Wisconsin-Madison: https://entrepreneurship.wisc.edu/

Check out the Empowering the Wisconsin Idea Report: https://news.wisc.edu/content/uploads/2024/09/EmpoweringtheWisconsinIdea-Report-Final4-Accessible-3.pdf

Valency Fund

Flexible funding solutions designed for sustainable growth of Wisconsin companies.

Learn more at https://www.valencyfund.com/

Subscribe to the Startup Wisconsin Newsletter

https://www.startupwi.org/

Upcoming Tech and Startup Events in Wisconsin (400+ every year)

https://www.startupwi.org/events

Follow us on LinkedIn

https://www.linkedin.com/company/startup-wisconsin/

Connect with Jacob Miller:

https://www.linkedin.com/in/kineticbear

Interested in being a guest? Reach out!

[email protected]

Startup Wisconsin's mission is to connect, educate, inspire, and grow tech startup communities across the state, not just during events, but year-round. This podcast is part of that vision, creating deeper connections and sharing the knowledge that helps Wisconsin's startup ecosystem thrive.

This podcast is made by your friends at Headway.

https://www.headway.io

“If nobody else is going to do this, I'm gonna jump in with both feet and I'm gonna make it happen.”

In this episode, I sit down with Justin Byers, founder and CEO of Axio BioPharma, to explore how his company is solving one of biotech's most overlooked bottlenecks: the broken flow of data between early-stage research and large-scale manufacturing. Through AI-powered data pipelines, Axio is helping get life-saving therapies to patients faster and more reliably.

Justin traces his path from bench scientist to biotech founder, sharing hard-won lessons from building a company in one of the most regulated industries in the world. He also makes the case for why high-throughput domestic drug manufacturing is more than a business opportunity. It's a national priority.

We also dig into Midwest BioCapital, Justin's pre-seed and seed-stage fund backing the next generation of Midwest biotech startups, and why the partnerships you choose in those earliest stages can make or break everything that follows.

(00:00) Introduction

Connect with Justin Byers: https://www.linkedin.com/in/justin-byers-03760931/

Valency Fund

Flexible funding solutions designed for sustainable growth of Wisconsin companies.

Learn more at https://www.valencyfund.com/

Subscribe to the Startup Wisconsin Newsletter

https://www.startupwi.org/

Upcoming Tech and Startup Events in Wisconsin (400+ every year)

https://www.startupwi.org/events

Follow us on LinkedIn

https://www.linkedin.com/company/startup-wisconsin/

Connect with Jacob Miller:

https://www.linkedin.com/in/kineticbear

Interested in being a guest? Reach out!

[email protected]

Startup Wisconsin's mission is to connect, educate, inspire, and grow tech startup communities across the state, not just during events, but year-round. This podcast is part of that vision, creating deeper connections and sharing the knowledge that helps Wisconsin's startup ecosystem thrive.

This podcast is made by your friends at Headway.

https://www.headway.io

“Every entrepreneur in Wisconsin has a place in this community.”

In this episode, I chat with Angela Damiani, CEO and Co-founder of NEWaukee, a brand engagement agency that has been making waves with its innovative activations, events, and community-building efforts. Angela shares the story of how NEWaukee, initially a social club for entrepreneurs, evolved into a thriving agency and a leader in fostering Wisconsin’s startup culture. She discusses the creation of the Midwest Founders Community (MFC), a decentralized network connecting founders across the region, and the inspiring work of elevating the Wisconsin tech scene through collaboration and mutual support.

From building a brand experience agency to leading an influential community of founders, Angela reflects on the importance of connection, mentorship, and a culture of belonging. She also shares the challenges of balancing multiple businesses and how she's helping others navigate the ups and downs of the entrepreneurial journey.

• How the Midwest Founders Community connects founders to capital, customers, and fellow entrepreneurs

(00:00) Introduction

Connect with Angela Damiani: https://www.linkedin.com/in/angeladamiani/

Valency Fund

Flexible funding solutions designed for sustainable growth of Wisconsin companies.

Learn more at https://www.valencyfund.com/

Subscribe to the Startup Wisconsin Newsletter

https://www.startupwi.org/

Upcoming Tech and Startup Events in Wisconsin (400+ every year)

https://www.startupwi.org/events

Follow us on LinkedIn

https://www.linkedin.com/company/startup-wisconsin/

Connect with Jacob Miller:

https://www.linkedin.com/in/kineticbear

Interested in being a guest? Reach out!

[email protected]

Startup Wisconsin's mission is to connect, educate, inspire, and grow tech startup communities across the state, not just during events, but year-round. This podcast is part of that vision, creating deeper connections and sharing the knowledge that helps Wisconsin's startup ecosystem thrive.

This podcast is made by your friends at Headway.

https://www.headway.io

“There’s no reason every small business in Wisconsin shouldn’t use this.”

In this episode, I chat with Russell From, President and Co-Founder of WayFi Wireless, a company revolutionizing connectivity for businesses and nonprofits across Wisconsin and the world. He shares the inspiring journey of how WayFi Wireless uses cutting-edge technology to fix cellular dead zones by leveraging wifi, without the hefty costs traditionally associated with infrastructure.

From working at Verizon to tech founder, Russell discusses WayFi Wireless' 10,000+ global deployments powered by PassPoint technology, bridging the digital divide by offering free connectivity to users that’s funded entirely by carriers. He also  shares their recent "Best Open Roaming Deployment" award, their work with the Coverage Across America Program in Wisconsin, and the hard-earned lessons he’s gathered while building a startup from the ground up.

(00:00) Intro

(00:36) Meet Russ of WayFi Wireless

(02:03) From Verizon engineer to founder

(06:38) Why Passpoint and open roaming took off

(12:40) Pivoting to Wi-Fi and scaling to 1,200 locations

(22:22) The business of Wi-Fi monetization

(28:41) How blockchain speeds up carrier payments

(35:57) Lessons from corporate to startup life 

(42:05) The transition from funding to self-sustaining growth

(46:08) Big wins and international expansion

Connect with Russell From: https://www.linkedin.com/in/russfr/

Follow us on LinkedIn: https://www.linkedin.com/company/startup-wisconsin/

Connect with Jacob Miller: 
https://www.linkedin.com/in/kineticbear

Valency Fund

Flexible funding solutions designed for sustainable growth of Wisconsin companies.

Learn more at https://www.valencyfund.com/

Subscribe to the Startup Wisconsin Newsletter

https://www.startupwi.org/

Upcoming Tech and Startup Events in Wisconsin (400+ every year)

https://www.startupwi.org/events

Follow us on LinkedIn

https://www.linkedin.com/company/startup-wisconsin/

Connect with Jacob Miller:

https://www.linkedin.com/in/kineticbear

Interested in being a guest? Reach out!

[email protected]

Startup Wisconsin's mission is to connect, educate, inspire, and grow tech startup communities across the state, not just during events, but year-round. This podcast is part of that vision, creating deeper connections and sharing the knowledge that helps Wisconsin's startup ecosystem thrive.

This podcast is made by your friends at Headway.

https://www.headway.io

The Startup Wisconsin Podcast is presented by Valency Fund.

“It shouldn’t be this hard to do good in this world.”

In this episode, I 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.

(00:00) Introduction

(00:33) Meet Jillian Bichanich of Cubbi and Pocketchange

(01:40) Cubbi’s mission to support families

(06:42) How Cubbi transitioned to sponsor funding

(09:38) Jillian's path to founding Cubbi and Pocketchange

(12:16) Building a strong co-founder partnership

(15:42) How Jillian balances two startups

(19:24) Why ego-free collaboration is essential for success

(22:46) Building a values-driven shopping app

(25:37) From branding to MVP the hard way

(28:03) Why Madison is ideal for entrepreneurs

(37:28) Cubbi’s new "pay what you can" model

Connect with Jillian Bichanich: https://www.linkedin.com/in/jillianphyllis/

Valency Fund

Flexible funding solutions designed for sustainable growth of Wisconsin companies.

Learn more at https://www.valencyfund.com/

Subscribe to the Startup Wisconsin Newsletter

https://www.startupwi.org/

Upcoming Tech and Startup Events in Wisconsin (400+ every year)

https://www.startupwi.org/events

Follow us on LinkedIn

https://www.linkedin.com/company/startup-wisconsin/

Connect with Jacob Miller:

https://www.linkedin.com/in/kineticbear

Interested in being a guest? Reach out!

[email protected]

Startup Wisconsin's mission is to connect, educate, inspire, and grow tech startup communities across the state, not just during events, but year-round. This podcast is part of that vision, creating deeper connections and sharing the knowledge that helps Wisconsin's startup ecosystem thrive.

This podcast is made by your friends at Headway.

https://www.headway.io