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upside

Jay Clouse and Eric Hornung

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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, commun ...
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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…
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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, Twitte…
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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! ———— Justin Bi…
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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 p…
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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 a…
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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. Ev…
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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 ShareTh…
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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 …
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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 searche…
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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 sta…
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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…
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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-f…
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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…
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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 …
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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 LeadPa…
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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 ge…
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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…
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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 …
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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 maintenan…
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Interview Begins : 7:37 Debrief: 45:43 Jack Greco is the co-founder of ACV auctions. ACV auctions is an online marketplace for used cars. As of November 2019, the company was valued at more than $1.5 billion. Jack has built a reputation for supporting other founders in the Buffalo area as one of the most active angels and advisors in the region. He…
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Interview Begins : 6:57 Debrief: 37:08 Karla Gallardo is the CEO of Viwala. Viwala provides loans for women entrepreneurs who have high-impact businesses as well as a network of mentors and entrepreneurs who aim to reduce the gender gap in Mexican businesses. We discuss: Idea for Viwala 8:52 Banking Culture in Mexico 11:23 Revenue Based Lending 13:…
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Interview Begins 6:53 Debrief 52:25 Patrick Lightbody is the co-founder of Reclaim. Reclaim is a smart calendar assistant that can save you up to 40% of your workweek. Reclaim aligns your priorities to the time you spend every week, empowering you to rapidly rebalance your schedule and defend your time to work on what matters. Like a power tool for…
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Interview begins: 6:28 Debrief: 41:25 John Gannon is the co-founder and general partner of GoingVC. John has mentored thousands of current and aspiring VCs through his VC Careers blog and email list, which counts VCs from top firms like Sequoia, KPCB, and Bessemer as subscribers. GoingVC was founded in 2016 with the goal of providing individuals wi…
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When we filmed Test City, USA in the summer of 2019 about the startup ecosystem in Columbus, Ohio, we knew the timing was special. Little did we know how good that timing was! Columbus has continued to gain momentum over the last two years. Here's a sample of the changes for companies and individuals featured in this film: Beam Dental - Raised $55M…
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Interview begins: 7:16 Debrief: 43:38 Ginger Rothrock is a Senior Director at HG Ventures. HG Ventures supports innovation and growth across The Heritage Group by investing and partnering with private companies developing new technologies and approaches in both our core and adjacent markets. We leverage the world class expertise of The Heritage Gro…
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Interview begins: 7:00 Debrief: 38:33 Tom Cottingham is the founder and CEO of Flyover Future. Flyover Future is a digital newsletter covering innovation and start-ups in the heartland. They cover the investors, the innovators and the ecosystems that help innovation thrive. We help our readers discover the amazing companies and initiatives througho…
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Interview begins: 7:07 Debrief: 38:45 William Hsu is a founding partner at Mucker Capital. He started his career as a founder, creating BuildPoint, a provider of workflow management solutions for the commercial construction industry not long after graduating from Stanford. Based in Los Angeles, Mucker invests in Seed and Series A rounds in Southern…
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Interview begins: 5:59 Debrief: 50:11 Rob Petrozzo is the co-founder and Chief Product Officer for Rally. Rally is a liquid financial marketplace for buying & selling equity shares in ultra-rare assets the same way you buy & sell stocks. Together, we Rally to make investing behind ideas, emotions, and communities safe, easy, and accessible. They we…
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Interview begins: 5:16 Debrief: 43:55 This week we’re revisiting CC058, a coffee chat with Peter Livingston of Unpopular Ventures. In this episode, we explored syndicate investing. Unpopular Ventures is led by Peter Livingston, whose experience is almost entirely in startups – as both an operator and investor. He was the first engineer at iRhythm (…
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Interview begins: 6:23 Debrief: 50:32 This week we’re hosting an upside feed takeover from When Pigs Fly! When Pigs Fly is a podcast covering the Cincinnati business ecosystem on the upside podcast network. And in this episode, they talk to Scott Shane, the Managing Director of Comeback Capital, to learn precisely what venture capital is, what inve…
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Interview Begins: 6:16 Debrief: 37:03 Michael Cohn and Sean O’Brien are the Managing Directors of Overline. Overline is an Atlanta-based, founder-operator led venture capital firm focused on investing in seed-stage businesses, primarily in Atlanta and the Southeast region of the United States. We partner with founders throughout their seed stage an…
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Interview begins: 5:49 Debrief: 51:25 Abby Mercado is the co-founder and CEO of Best Shot. Best Shot is a patient’s companion in fertility treatments, providing medication management & education, streamlining the pharmaceutical ordering experience and enabling safe, supportive micro-communities led by experts. Abby is a former venture capital inves…
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Interview begins: 7:15 Debrief: 55:14 Jackie DiMonte is a partner at Chicago Ventures. Prior to joining Chicago Ventures, Jackie was a principal at Hyde Park Venture Partners, working with portfolio companies such as RoadSync, Podchaser, Fixer, FactoryFix, and PartySlate. Before that, she worked at Silver Spring Networks (now Itron), an IoT company…
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Interview Begins: 7:12 Debrief Begins: 55:03 Jessica Peltz-Zatulove is a Founding Partner at Hannah Grey, a first check venture capital firm investing in customer-centric founders reimagining everyday experiences to improve work and life. She is also the co-founder of Global Women in VC, the world's largest and most active community for women inves…
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Interview Begins: 8:19 Debrief 46:25 Zachary Spradlin is a co-creator of Protoball, a futuristic first-person sports game merging basketball, soccer, and high tech style. Players athletically jump, slide, run, and dash around the arena trying to pass the Protoball through the opponents goal. We discuss: Failed Kickstarter Campaign 10:22 Protoball a…
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Interview begins: 7:58 Debrief: 47:33 Chris Bergman is the founder and CEO of Gylee Games and a General Partner at The Fund Midwest. Gylee Games believes in building big worlds. They believe in games that can be enjoyed in smaller chunks, not requiring hundreds of hours, but a delightful experience in short bursts. Gylee Games creates games for PC,…
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Interview begins: 6:51 Debrief: 53:55 Ben Kellie is the Founder and CEO of The Launch Company The Launch Company is building the world’s first multi-user, mobile launch site for this planet and beyond. They develop standardized hardware, ground support equipment, and processes. Ben has a B.S. in mechanical engineering from University of Alaska Fair…
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Interview begins: 11:40 Debrief: 58:48 John Crain is the Founder and CEO of SuperRare. SuperRare is a marketplace to collect and trade unique, single-edition digital artworks. Each artwork is authentically created by an artist in the network, and tokenized as a crypto-collectible digital item that you can own and trade. Each artwork on SuperRare is…
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Interview begins: 4:27 This week we’re hosting an upside feed takeover from Lay of The Land! Lay of The Land is a podcast covering the Cleveland business ecosystem on the upside podcast network. And in this episode, Jeff talks with Steve Muszynski, the founder and CEO of Splash Financial. Jeff and Steve discuss the student loan crisis and how Splas…
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Interview begins: 5:22 Debrief: 41:15 Travis Smith is the founder and CEO of Tribevest. Tribevest makes it easy to launch an investor entity, pool capital, and experience wealth-building with friends, family, and people you trust. Tribevest’s all-in-one-platform helps you assemble your tribe, align on your expectations, file your LLC, author your b…
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Interview begins: 6:33 Debrief: 46:48 Geoff Atkinson is the founder and CEO of Huckabuy. Huckabuy’s Software improves your search results, drives more organic traffic, and makes your website faster. Their software creates Google’s Perfect World on your website to queue up the perfect conversation with Search Bots and grow your organic traffic. Prio…
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Interview begins: 5:52 Debrief: 34:02 Nick McCullum is the Director of Growth for Passiv. Passiv turns your brokerage account into a modern portfolio management tool. Passiv allows you to set a target portfolio and get email notifications when your portfolio drifts from that target. Passiv then lets you rebalance with one click! We discuss: What ma…
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This week we’re excited to introduce you to the first new show on the upside podcast network: When Pigs Fly. Hosted by Allie Martin and Patrick Bailey, When Pigs Fly is a podcast that uncovers Cincinnati's rich business history from the 1800s to today. We talk to companies to learn the ups and downs of entrepreneurship, what it takes to grow a succ…
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Interview begins: 5:01 Debrief: 40:42 Caleb Musser is the founder and CEO of Craftom. Craftom is a B2B gifting and shipping platform that makes it easy to send hyper-designed corporate gifts, products and office equipment to anyone, whether they’re working from home, in the office, or somewhere else entirely. It started with a cigar box and a tough…
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Interview begins: 6:02 Debrief: 42.:02 Landon Ainge is the Managing Director of Assure Syndicates. Assure Syndicates is a division of Assure. Assure is the pioneering leader in providing comprehensive structuring and administrative management services (specifically Special Purpose Vehicles) to the private investment ecosystem. Assure Syndicates’ mi…
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Trent and Travis Hedge are brothers from Columbus, OH, who left for Silicon Valley. But since that time, both have continued to visit and advocate for Ohio and other parts of the country. Travis Hedge is the co-founder of Vouch Insurance (YC S19). Vouch Insurance is an insurance company designed for startups. It was developed by founders for founde…
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Today is the final episode in our “Rewind” Series. Rachel Carpenter is the co-founder and CEO of Intrinio. Intrinio is a financial data company on a mission to power fintech innovation by providing affordable, high-quality data to developers and engineers from fintech companies, large institutions, hedge funds, startups, and universities. Their mis…
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Today is the fourth episode in our December series called “Rewind.” Amanda DoAmaral is the founder and CEO of Fiveable, which is based in Milwaukee Wisconsin. Fiveable is an online streaming and content platform helping high school students study and master their AP exams. Started just two years ago, Fiveable offers live and pre-recorded videos, st…
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Today is the third episode in our December series called “Rewind.” Jeremiah Chapman is the founder and CEO of FreshFry. We first talked with Jeremiah back in July 2018 in episode 12 of this show. FreshFry, located in Louisville, Kentucky, creates plant-based product that helps food service businesses extend the life of frying oil. FreshFry’s “pods”…
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