upside
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."
Episodes
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 cu...
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.
Follow When Pigs Fly:
Facebook, Instagram, Twitter
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. Really enjoyed this conversation and hope you do too!
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Justin Bibb is a proud Cleveland native who grew up in Mt. Pleasant on the s...
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, e...
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 podcast...
[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.
Evan Knowles is the co-founder and CEO of Symba, the real estate industry's only mobile-first CRM. Evan and his experienced co-founders are bringing a fresh perspective and mo...
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 A funding where they invest $1M to $2M.
Tim Schigal is the Managing Partner at Refinery Ventures, and the host of Fast Frontiers. Tim created ShareThis, a social media pioneer that nearly a billion people use to share online co...
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 billions of dollars to Africa oftentimes to pay for healthcare. Without direct insight into how the funds are being spent and whether adequate treatment is being provided, immigrants are left to worry about whether the money they...
[Think Like An Owner] Badge Stone – Earning His Badge and Making His Mark in Search Fund Investments
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 bankruptcy when he acquired it. After turning it around, he acquired another company called Perimeter Security. He sold both and made investing in searchers his full-time role through his firm, WSC & Company, alongside two ...
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 interviews. But our feed isn’t going dark – each week, if we don’t share one of our own interviews, we’ll be hosting a feed drop of other great shows in the startup and investment space.
And along the way, we’ll be jumping in to ...
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 understanding or accessibility of truly nutrient-dense foods.
They use raw, sprouted, organic ingredients that are GMO-free and never pressurized or treated with chemicals or preservatives, allowing them to maintain up to 98...
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 country, closing hundreds of C-level searches every year.
For over 40 years, SPMB has specialized in recruiting upper management and board members to VC-funded startups everywhere from early-stage to growth stage.
They ...
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 Director for Techstars, a leading startup accelerator with over 40 programs around the world. While at Techstars he ran three accelerator programs in Kansas City and invested in 30 startups. Companies that have gone thr...
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 estate, crypto, and video game investments. Focused on creating a diverse, sustainable, connected world, Republic has facilitated over $600 million in investments from over one million global community members.
Previ...
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 company with a little bit of financial backing from TinySeed and a few angel investors.
Previously, Derrick co-founded Drip, which was acquired by LeadPages. He hosts The Art of Product Podcast, where he shares what he i...
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, lifestyle, and blood level data.
Follow Rachel Sanders: https://www.linkedin.com/in/rachel-soper-sanders/
Website: https://rootine.co/
Key Points:
- The genius behind Rootine 8:53
- Fads and the underlying truth 9:55
- What make...
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 this high-returning asset class with SEC-qualified collections.
Fine wine has returned over 9% annually and has low volatility over the long term. Wine has offered diversification benefits in both good times and bad tim...
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 leave us feedback, questions, or a little love! Your support goes a long way.
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 the Midwest. Since they launched in 2015, they've become the most active investor in the region.
They are led by two of the youngest fund managers in the industry, and they enjoy challenging traditions. They invest broadly...
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 experience reduced repair times, decreased delays, and lowered time costs, while mitigating the risk of FAA compliance.
Andy has been an aircraft maintenance guy & aviation geek since 1989. A founding member of the Aire...
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