219 episodes

Named a top 27 business podcast by Fortune, upside examines startup investing outside of Silicon Valley.

Every Wednesday, we speak with an early stage founder. We interview them as if we are angel investors considering the company as an investment opportunity.

Each show has three segments:

1.) Intro: independent research of the company
2.) Interview: interview with the founder
3.) Debrief: breaking down the opportunity

Sometimes, we share Coffee Chats interviewing venture capitalists, community builders, and later-stage founders.

Subscribe and see why Business Insider called our podcast "Almost as Good as Getting an MBA."

upside Jay Clouse and Eric Hornung

    • Business
    • 4.9 • 126 Ratings

Named a top 27 business podcast by Fortune, upside examines startup investing outside of Silicon Valley.

Every Wednesday, we speak with an early stage founder. We interview them as if we are angel investors considering the company as an investment opportunity.

Each show has three segments:

1.) Intro: independent research of the company
2.) Interview: interview with the founder
3.) Debrief: breaking down the opportunity

Sometimes, we share Coffee Chats interviewing venture capitalists, community builders, and later-stage founders.

Subscribe and see why Business Insider called our podcast "Almost as Good as Getting an MBA."

    [Powderkeg] The founding story of Indianapolis darling startup Lessonly

    [Powderkeg] The founding story of Indianapolis darling startup Lessonly

    Culture, when built correctly can be your key differentiator. When built incorrectly it can be your Achilles' heel.

    Today we do a deep dive into the founding story of Indianapolis darling startup Lessonly. Lessonly is a market leader in training software and was acquired by San Diego-based Seismic in 2021.

    We sit down with co-founders Max Yoder and Conner Burt to discuss Lessonly's development over the last decade and why culture has always been a North Star in the companies evolution.

    Max and Conner both started their professional career by means of the Orr Fellowship, a two-year, Indianapolis-based fellowship focused on developing the next generation of business leaders and entrepreneurs.

    Max began working on Lessonly after winding down his first startup. Conner was working in sales at ExactTarget (acquired by Salesforce) at the time. The two were roommates and Conner became an early adopter of the original Lessonly platform, where he used it to help train an international sales team of ExactTarget.

    Learn more about the Lessonly journey and hear the words of wisdom this dynamic duo has about growing a high-performing, venture-backed tech company.

    If you like this episode, please subscribe and leave a review on iTunes. You can also follow on Soundcloud or Stitcher.

    • 40 min
    [When Pigs Fly] #42: Making Medical Bills Bearabill (feat. Lisa Matsuyama & Forest Satterfield of Bearabill)

    [When Pigs Fly] #42: Making Medical Bills Bearabill (feat. Lisa Matsuyama & Forest Satterfield of Bearabill)

    Making medical bills Bearabill.

    We chat with Lisa Matsuyama and Forest Satterfield, the founders of Bearabill, to learn how they're building a startup that predicts future healthcare costs, identifies medical billing errors and overcharges, and how they're negotiating on your behalf for lower bills.

    • 56 min
    [Lay of The Land] #15: Justin Bibb (Mayor-Elect of Cleveland)

    [Lay of The Land] #15: Justin Bibb (Mayor-Elect of Cleveland)

    Lay of the Land’s fifteenth conversation is with Justin Bibb, the new Mayor-elect of Cleveland.

    This conversation originally aired on March 18, 2021 and covers a lot — through a lens of technology, entrepreneurship, and equity, we explore Justin’s vision for the city of Cleveland.

    • 50 min
    Powerspike // connecting brands and creators on Twitch with a self-serve advertising platform [UP094]

    Powerspike // connecting brands and creators on Twitch with a self-serve advertising platform [UP094]

    Interview Begins: 8:51
    Debrief Begins: 51:07

    A.J. Damiano is the co-founder and CEO of Powerspike.
    Powerspike is the easiest way to sponsor influencers in the esports & gaming space. Powerspike helps you create campaigns, connect with Twitch influencers and teams at scale, without all the busy work – making it simple to advertise on Twitch.
    Their platform merges influencer marketing with programmatic advertising, enabling brands to create an influencer campaign just like they'd make a media buy.
    The process takes 4 minutes or less, and saves the average brand over 150+ hours of work.
    There's no negotiating, no having to tediously search through lists of thousands of influencers, and most importantly, no heavy lifting. Simply tell PowerSpike what you want, and it delivers results.

    We discuss:
    - Twitch back in 2014 12:35
    - Getting Brand Sponsorships 20:21
    - Pitch Model Pre Techstars 22:25
    - Pitch in Today's time 23:10
    - Brand Safety 26:39
    - Creator's Inventory Management 30:18
    - How to be on Powerspike 33:40
    - Creator's on Powerspike 34:48
    - Building the Marketplace 38:02
    - Powerspike's Business Model 40:24
    - Best for Powerspike 41:48

    Foodnerd was founded in 2015 and based in New York City.

    • 1 hr 3 min
    [Chicago Capital] Ezra Galston of Starting Line on Resiliency, Starting Line Fund II, & the State of Chicago Tech

    [Chicago Capital] Ezra Galston of Starting Line on Resiliency, Starting Line Fund II, & the State of Chicago Tech

    This week on the feed we're featuring the Chicago Capital Podcast.

    Chicago Capital is hosted by Matt Castellini and explores the Venture Capital and Entrepreneurial ecosystem in Chicago.

    Matt is currently getting his MBA from the University of Chicago Booth School of Business while working in early stage VC.

    He grew up in the Chicagoland area and attended Notre Dame for undergrad. He became obessesed with podcasts and podcasting after college. He finally decided to start one when I saw an opportunity to spotlight a city that I felt was not receiving the national recognition it deserved.

    Matt is also the author of Venture Scenes, where I blog about Startups, Venture Capital, and Movies.

    Ezra Galston is the Founding Partner at Starting Line, a Chicago-based early-stage venture capital firm that invests in leading consumer products and brands.

    In this episode, they cover:
    Fundraising Resiliency
    Starting Line Fund II
    Building to Conviction
    Post-Investment Value-Add
    The Challenges of the VC Feedback Loop
    State of Chicago Tech

    • 53 min
    [Middle Tech] Symba: Evan Knowles on Building the Only Mobile-First CRM for the Real Estate Industry

    [Middle Tech] Symba: Evan Knowles on Building the Only Mobile-First CRM for the Real Estate Industry

    This week on the feed we're featuring the Middle Tech Podcast.

    Middle Tech was created to advance the business ecosystem in this region by providing news, entertainment, and educational content related to startups, entrepreneurship, and technology.

    • 59 min

Customer Reviews

4.9 out of 5
126 Ratings

126 Ratings

Namoono3 ,

Excited About Upside

Eric and Jay, I am so excited about upside and the concept of building a business outside the valley. I can’t wait to hear more 👍👍👍

carogal ,

!!!

Loved the episode with Jackie! I hope you circle back with her once the world normalizes a bit. Informative and interesting!

ALAZ1 ,

Great show

Jay and Eric are natural conversationalists and they shed light on the leaders in tech ecosystems outside Silicon Valley!

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