Author: 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, community builders, and later-stage founders.

Subscribe and see why Business Insider called our podcast "Almost as Good as Getting an MBA."
187 Episodes
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.
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 for critical infrastructure, driving development and pilot projects for emerging smart city technology. She is also a member of the Board of Directors for Starting Block Madison and Chicago:Blend and a Venture Partner at Republic. We discuss: - Feedback Loop 13:54 - Evolution in a Venture Firm 17:14 - What Level is a Deal Flow Done? 21:46 - Get a Deal Through 24:17 - Programmatic Venture 26:35 - Working Virtually from Austin 31:13 - Partner at Chicago Ventures 35:27 - Inbound Pitches 42:43 - Fragmenting Markets 48:53 - Personal Goals for the role 50:26 Chicago Ventures was founded in 2012. Learn more about Chicago Ventures: Follow Jackie on Twitter:
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 investors, empowering women VCs around the world to better find each other to connect, collaborate, and create a sense of community. We discuss: - Disconnect in large and a small companies 11:29 - Find the right stakeholder 13:23 - Working with Startup Founders 18:33 - Coming out of Corporate VC 23:19 - Women in VC 30:04 - Hannah Grey 36:33 - What does Hannah Grey Support? 35:51 - Economic Trends 44:13 - Pre Seed Fund 48:39 Haannah Grey was founded in 2020 and based in New York City. Learn more about Hannah Grey This episode is sponsored by SavvyCal. SavvyCal is the most intuitive and powerful scheduling tool on the market. In fact, we just started SavvyCal to book interviews with our guests! You can create personalized links in seconds and even allow recipients to overlay their calendar on top of yours. You really gotta see how this works, and you’ll wonder why it wasn’t always this easy. Sign up to create a free account at and when you're ready to test out a paid plan, use the code UPSIDE to get your first month free. Follow upside on Twitter Advertise with an upside classified
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 and the concept behind it. 12:42 - Unreal Engine 16:26 - Needing a Hit Game 19:15 - Creating Protoball 20:49 - Game Jam 22:25 - What makes a good game 23:52 - Scenes from Protoball 26:02 - Scoring 30:37 - Protoball as eSports 32:15 - Unserved Audience 33:31 - Free to Play 35:12 - Funding the game 38:05 - Game Development vs. Business Development 41:16 - Protoball open to public 43:50 Protoball was started in 2018 and based in Cincinnati, Ohio. Learn more about Protoball This episode is sponsored by Fundboard. You can build a tailor-fit list of startup investors in minutes with FundBoard. Learn more at Follow upside on Twitter Advertise with an upside classified
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, Console and VR. The Midwest Fund was born from The Fund, an NYC-based venture capital group. Founded in 2018 by an all-star cast of Jenny Fielding, Scott Hartley, Katie Hunt, Adam Carver and Matthew Brimer, The Fund has since expanded with micro-funds in Los Angeles, London and the Boulder/Denver region. And with each expansion, local founders and investors are tapped to lead each region. We discuss: - ChoreMonster 9:26 - Gylee Games and The Fund Midwest 10:19 - Chris Bergman as a game developer and creator 11:56 - Surrounding yourself with people that are really good 13:35 - Funding a gaming studio 16:59 - Game Studio Aspects 18:41 - Gaming and Venture Capital 19:51 - Pre-release marketing 23:27 - Pressure on the first game 29:03 - Strategy on acquisition model 30:46 - Twitch to become stakeholders 32:04 - Entering The Fund Midwest 32:56 - Investment Thesis 38:31 - Funded by founders, run by founders 39:50 - Raising as an operator vs as a VC 44:50 -- Learn more about The Fund Midwest: Learn more about Gylee Games: Follow Chris Bergman on Twitter: This episode is sponsored by Fundboard. You can build a tailor-fit list of startup investors in minutes with FundBoard. Learn more at Follow upside on Twitter: Advertise with an upside classified:
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 Fairbanks, as well as an M.S. in mechanical engineering from the Ohio State University. Before returning to Alaska, Ben worked in rocketry at SpaceX, designing and operating launch sites, and ran the first missions to return a first stage from orbit. The Launch Company was founded in 2015 and based in Anchorage, Alaska. Learn more about The Launch Company: Follow Ben Kellie on Twitter: This episode is sponsored by Fundboard. You can build a tailor-fit list of startup investors in minutes with FundBoard. Learn more at Follow upside on Twitter: Advertise with an upside classified:
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 a digital collectible– a digital object secured by cryptography and tracked on the blockchain. That’s just a fancy way of saying they’re probably scarce items that can be collected, and that hold value just like cryptocurrencies like ether and bitcoin. You can think of SuperRare like Instagram meets Robinhood. A new way to interact with art, culture, and collecting on the internet! Key points: - Getting to the world of crypto 10:45 - Difference of Bitcoin and Etherium 13:31 - What’s does SuperRare offer 14:58 - SuperRare 16:28 - Crypto Kitties 20:02 - Art world and Technology 23:00 - What is Digital art? 25:49 - Collecting digital art 26:45 - Value of digital art 30:57 - Audience of SuperRare 34:00 - Certificate of Authenticity 35:37 - SuperRare as a marketplace business 40:36 - Transaction fees and costs 45:52 - The future of art/museums 51:17 Learn more about SuperRare: Follow John Crain: Follow upside on Twitter: Follow upside on Twitter: Advertise with an upside classified:
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 Splash, one of Ohio’s fastest growing companies, is helping people save on their student loan debt. We discuss: - Status Quo for Student Loans 6:34 - Coming up with Splash Financial 8:12 - Progress amidst the current situation 13:12 - Loan Forgiveness 15:53 - Think about growth 18:32 - Starting in Cleveland 21:38 - Hiring employees 25:12 - Challenges for Splash 29:26 Splash Financial was founded in 2015 and based in Cleveland, Ohio. Learn more about Splash Financial: Subscribe to Lay of The Land: Follow upside on Twitter: Advertise with an upside classified:
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 bylaws, open a business bank account, and easily pool capital from your members. We discuss: - Early interest in finance 6:51 - Investing as brothers 11:44 - Investing in real estate 12:54 - What is Tribevest 14:54 - Onboarding 20:16 - Difference if Tribevest vs. SPV 22:53 - Growth Strategy 26:32 - Tribevest Vision 29:24 - Subscription model 36:45 Tribevest was founded in 2016 and based in Columbus, Ohio. Learn more about Tribevest: Follow upside on Twitter: Advertise with an upside classified:
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. Prior to Huckabuy, Geoff was the Senior Vice President of Marketing and Analytics at Overstock. At Overstock, he developed expertise in SEO and managed everything from pricing algorithms to content generation, to buying rain jackets in New York City’s garment district. In 2007, he was named on Advertising Age’s “Top 40 Under 40” list. Huckabuy was founded in 2015 and based in Park City, Utah. Learn more about Huckabuy: Follow upside on Twitter: Advertise with an upside classified:
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!
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 successful business and to simply prost to future innovation. When Pigs Fly will air every Tuesday beginning February 2 on the upside podcast network. Subscribe to When Pigs Fly: Learn more: Follow When Pigs Fly on Twitter: Follow upside on Twitter: Follow upside on Twitter: Advertise with an upside classified:
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 sales job. In 2013, Craftom founder Caleb Musser was searching for a unique way to stand out with business owners while selling printers and copiers door-to-door. So he scrounged up vintage cigar boxes and sent them with personalized notes and gifts to unresponsive business owners. The reaction was eye-opening. Executives who wouldn’t take his calls before started connecting with Musser and giving him time on their busy calendars. The success of this home-spun hack revealed two key insights that are still engrained in’s DNA today: Customization and personalization are everything, and nothing beats quality materials and products. By combining cutting-edge design technology with quality products, Craftom has designed and created gifts that sit on the desks of Fortune 500 CEOs, NFL owners and Presidents of the United States. Craftom was founded in 2019 and based in Charlotte, North Carolina. We discuss: - Caleb Musser as a Salesman 7:54 - Musser & Co. 12:31 - Craftom 17:48 - The difference of the two companies 19:50 - Craftom being the main venture 20:46 - Advantage of adding technical components to your business 22:19 - How pandemic change business relationships 26:06 - Growth during the pandemic 27:26 - The key to cold outbound calls 29:07 - Why do customers choose Craftom 31:02 - Craftom being completely Bootstrapped 37:49 Learn more about Craftom: Follow upside on Twitter: Advertise with an upside classified:
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’ mission is to connect the right investors with the right businesses. Assure Syndicates is a one-of-a-kind hybrid that aligns with fellow investors while advocating for the founder. We provide fundraising guidance to founders, then commit our own capital to the deal. We discuss: - Investing vs. Operating 6:48 - Being a great venture capitalist. 7:31 - Special Purpose Vehicles as Investment 9:18 - Assure as a SPV expert 12:03 - Assure Syndicate's Purpose in the Marketplace 15:44 - 3 Skill sets in venture 18:23 - Assure Syndicate and VCs 21:23 - New trend of founder syndicating deals 26:59 - Landon Ainge getting on Assure 30:44 - Guide to build your own Syndicate 39:25 Learn more about Assure Syndicates: Follow Landon on Twitter: Follow upside on Twitter: Advertise with an upside classified:
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 founders and redesigned everything about business insurance from scratch. The company offers a platform that works with clients to manage, mitigate, and avoid risks. Vouch Insurance was founded in 2016 and has its offices in San Francisco and Chicago. Trent Hedge is the co-founder of Atmos (YC S20). Atmos offers the entire homebuilding process all in one place—from design to move in. Atmos was founded in 2019 with a presence in SF, Raleigh, Durham, and Charlotte. Learn more about Vouch: Follow Travis on Twitter: Learn more about Atmos: Follow Trent on Twitter: Follow upside on Twitter: Advertise with an upside classified: --- This episode of upside is sponsored by Ethos Wealth Management. Managing wealth with an eye toward the future demands vigilance and skill in today’s global economy. Over the years, Ethos Wealth Management has worked with clients and their other professional advisors – including attorneys and accountants – to create comprehensive wealth management plans designed to make the best use of their wealth today and help ensure its endurance for future generations. They can do the same for you. Visit to learn more. – Want to share information about your company, or an opportunity with the upside audience? Book a classified advertisement and your advertisement will be read in an upcoming episode of the show. Classified ads are priced at $100, and are: - read by Jay and/or Eric on upside - linked from the show notes - linked from this website,
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 mission is to power the innovators defining the future of finance through modern data technologies. That means automating the data supply chain with advanced infrastructure and machine learning, delivering high-quality data through cutting-edge tools designed for developers and engineers, and getting it all in the hands of people who are challenging the system. Learn more about Intrinio: Follow Rachel on Twitter: Follow upside on Twitter:
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, study guides, as well as community building resources. After teaching in Oakland for several years with Teach for America, Amanda DoAmaral began Fiveable as a way to help her old students who needed guidance in studying for their AP exams. In only a couple years, Fiveable has grown to include teachers from various types of backgrounds and boasts a 92% pass rate from their students. Since we chatted in November 2019, Fiveable has raised more than $3.8M in funding. We discuss: - TFA training and lack of teaching preparation - Teaching in Oakland and decision to leave - Start of Fiveable - Business growth - Live streaming vs. pre-recorded videos - Teachers/streamers on Fiveable - SAT/ACT prep - Measuring success - Dealing with seasonality of APs - Fiveable’s tiny team Learn more about Fiveable: Follow Fiveable on Twitter: Follow upside on Twitter: Advertise with an upside classified:
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” strip water, acids, metals, and other impurities out of cooking oil, slowing breakdown by several days and helping businesses save on costs while improving food taste. Since we chatted, FreshFry has raised $3.3M in July 2020 from Lightship Capital and the USDA. Learn more about FreshFry: Follow upside on Twitter: Advertise with an upside classified:
Today is the second episode in our December series called “Rewind.” Blake Lawrence is the founder and CEO of Opendorse. We first talked with Blake back in April 2019, and our episode aired on July 17, 2019. Since that time, Opendorse has grown a lot. They’ve not only raised a Series A, but just this week they announced a partnership with Team USA. Opendorse is the athlete-marketing platform that helps the biggest brands in sports share content on social. Founded by two former major college athletes, Opendorse was built seeking to make it easy for athletes and their partners to work together to engage their fans. Today, more than 7,000 athletes use Opendorse to share content with their 1.4b social media followers. Top sports properties including the PGA TOUR, LPGA, NFLPA, WTA, and New Jersey Devils, and college properties including Michigan, Clemson, and Nebraska Athletics partner with Opendorse to send content to athletes to share through their social media channels. More than 1,500 brands also use opendorse to engage professional athletes and their audience. Learn more about Opendorse: Follow Blake on Twitter: Follow upside on Twitter: Advertise with an upside classified:
Today we are introducing our December series called “Rewind.” In this series, we will introduce one of the companies we’ve had on the show, give a quick update, and replay that episode in its entirety. We think this will be a really fascinating look back on these companies to see how far they’ve come over the last 6-18 months. And we’re kicking this series of with Balto. We talked to Balto CEO Marc Bernstein in June of 2018. At the time, Balto described itself this way: "Balto helps sales, service, and accounts receivable reps win as much revenue as possible from every phone call. Teams use Balto’s artificial intelligence software to analyze phone calls in real-time – live while the call is still happening – and instantly provide reps recommendations on how to communicate as effectively as possible before it’s too late. For more information visit” Since our conversation with Marc in June 2018, Balto raised $1.3M in October 2018. Then, they raised another $3M in September 2019. Both of those rounds featured Stage Venture Partners, another former guest on this show. And then, just over a month ago in October 2020, Balto raised a $10M Series A led by Sierra Ventures bringing their total funding to date up to around $14.3M since we spoke with them. Today, Balto describes themselves this way: "Balto is the leader in real-time guidance for contact centers. Powered by AI, Balto's software solution evaluates both sides of a phone call and instantly delivers critical information that enables agents to perform at the highest level humanly possible. With Balto, contact centers deliver world-class customer experiences, increase conversions, and decrease agent ramp time. Current customers include contact centers in sectors such as insurance, telecommunications, retail, financial services, and healthcare. For more information, visit" Super similar, but a little different. We are big fans of Marc here on the show, so we love seeing his team continue to grow and succeed. Now, we’ll share with you the original interview with Marc from June 2018. Knowing where the team has gone now, it’s an awesome listen to hear where they started. We’d love to hear your thoughts on this episode as you listen, you can tweet at us @upsidefm or email us And check out our new branding! We’ve refreshed our show artwork here, as well as our entire website. Check it out and let us know what you think. Follow Balto: Follow upside on Twitter: Advertise with an upside classified:
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