upside

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 Less…

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…

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, en…

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 yo…

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 curren…

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 relate…

This week on the feed we're featuring the Fast Frontiers Podcast by Refinery Ventures.

Refinery Ventures is based in Cincinnati, Ohio. They bridge the gap and mentor teams between post-seed and Series…

On this episode, Elio interviews Sam Baddoo, Founder of Fleri. Fleri helps immigrants protect the people who matter most back home with health insurance. Every year immigrants in the Diaspora send bi…

This week's feed drop features Alex Bridgeman and his podcast, Think Like An Owner.

Alex's guest is Badge Stone. Badge started his search journey with Stone Pump & Trench that was on the verge of bank…

This week, we’re sharing a quick update about what’s coming up for the feed for the rest of the year. 

Due to some competing life priorities, we need to take a short break from recording new interview…

Interview Begins 8:35
Debrief Begins 42:37

Sharon Cryan is the founder and CEO of Foodnerd.

Foodnerd specializes in 100% plant-based superfood products that are designed to increase the world's understa…

Interview Begins 5:05
Debrief Begins 25:39

Samantha (Sam) German is a Client Partner in SPMB’s Emerging Markets Practice.

SPMB is one of the fastest-growing retained executive search firms in the countr…

John Fein and Chris Marks are the managing partners of Firebrand Ventures.

John started Firebrand Ventures in 2016, and we interviewed him in 2018.

Prior to founding Firebrand, John served as Managing …

Interview Begins 8:02

Debrief 50:00

Kendrick (Ken) Nguyen is the co-founder and CEO of Republic.

Republic empowers everyone to invest in the future they believe in by providing access to startups, real …

Interview Begins 8:16

Debrief 54:58

Derrick Reimer is the founder and CEO of SavvyCal.

SavvyCal wants to take the friction and awkwardness out of scheduling time with people. They’re an indie SaaS compa…

Interview begins: 6:52

Debrief: 44:32

Rachel Sanders is the co-founder and CEO of Rootine.

Rootine was founded in Nashville, Tennessee, in 2018 and creates custom daily vitamins based on your DNA, lifes…

Interview Begins: 7:25
Debrief Begins: 46:24

Nick King is the co-founder and CEO of Vint.

Vint is the first fully transparent platform for anyone to invest in fine wine and spirits. They democratize thi…

Today we are launching the upside network on Product Hunt! We've put a ton of work in preparing for this campaign, and we'd love for you to check out our campaign.

Just visit https://upside.fm/hunt to…

Interview Begins: 9:01
Debrief: 59:30

Victor Gutwein is the Founder and Managing Partner of M25

M25 is an early-stage venture firm based in Chicago, investing solely in tech startups headquartered in th…

Interview Begins 8:09

Debrief 48:37

Andy Hakes is the founder and CEO of AirExpert.

AireXpert offers maintenance control, quality assurance, base, line, and vendor maintenance, enabling users to experie…