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upside

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."
180 Episodes
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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: https://splashfinancial.com/ Subscribe to Lay of The Land: https://pod.link/1539921799 Follow upside on Twitter: https://twitter.com/upsidefm Advertise with an upside classified: https://upside.fm/classifieds
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: https://www.tribevest.com/ Follow upside on Twitter: https://twitter.com/upsidefm Advertise with an upside classified: https://upside.fm/classifieds
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: https://passiv.com/ Follow upside on Twitter: https://twitter.com/upsidefm Advertise with an upside classified: https://upside.fm/classifieds
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: https://pod.link/1549482801 Learn more: https://whenpigsfly.fm Follow When Pigs Fly on Twitter: https://twitter.com/WhenPigsFlyPod Follow upside on Twitter: https://twitter.com/upsidefm Follow upside on Twitter: https://twitter.com/upsidefm Advertise with an upside classified: https://upside.fm/classifieds
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 Craftom.io’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: https://craftom.com/ Follow upside on Twitter: https://twitter.com/upsidefm Advertise with an upside classified: https://upside.fm/classifieds
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: https://syndicates.assure.co/ Follow Landon on Twitter: https://twitter.com/LandonAinge Follow upside on Twitter: https://twitter.com/upsidefm Advertise with an upside classified: https://upside.fm/classifieds
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: https://vouch.us Follow Travis on Twitter: https://twitter.com/The_HedgeFund Learn more about Atmos: https://buildatmos.com Follow Trent on Twitter: https://twitter.com/trenthedge Follow upside on Twitter: https://twitter.com/upsidefm Advertise with an upside classified: https://upside.fm/classifieds --- 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 upside.fm/ethos 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, upside.fm
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: https://intrinio.com Follow Rachel on Twitter: https://twitter.com/Rachel_Ann_C Follow upside on Twitter: https://twitter.com/upsidefm
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: https://fiveable.me/ Follow Fiveable on Twitter: https://twitter.com/thinkfiveable Follow upside on Twitter: https://twitter.com/upsidefm Advertise with an upside classified: https://upside.fm/classifieds
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: https://www.freshfry.me/ Follow upside on Twitter: https://twitter.com/upsidefm Advertise with an upside classified: https://upside.fm/classifieds
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: https://opendorse.com/ Follow Blake on Twitter: https://twitter.com/Blake_Lawrence Follow upside on Twitter: https://twitter.com/upsidefm Advertise with an upside classified: https://upside.fm/classifieds
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 Baltosoftware.com” 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 balto.ai." 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 hello@upside.fm. 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: https://balto.ai/ Follow upside on Twitter: https://twitter.com/upsidefm Advertise with an upside classified: https://upside.fm/classifieds
This year has been unlike any other. And this Thanksgiving is likely to be unlikely any other, too. With the difficulties that 2020 has brought everyone – founders, investors, and communities – there are still some bright spots to celebrate. In today’s short episode, we talk about some of the positives 2020 has brought us and startup communities that we can still be thankful for. From the upside family, we hope you have a safe and happy Thanksgiving! Follow upside on Twitter: https://twitter.com/upsidefm Advertise with an upside classified: https://upside.fm/classifieds
This week we're excited to introduce you to the first new show on the upside podcast network: Lay of The Land.
We’re excited to share with you a major project that we’ve been working on behind the scenes! Starting in 2021, the upside podcast network will be launching a growing number of localized business podcasts. The upside podcast network helps local teams to produce high-quality shows covering their local business ecosystems. Hosts on the ground will interview business leaders in their local communities, produced and supported by upside. The journey begins this month with our first show: Lay of the Land. Hosted by Jeffrey Stern and TheTagan, Lay of the Land covers the Cleveland business community. In this week’s episode, we’ll talk about why we’re building a network, what it means for the future of business podcasts, and how you can get involved. Want to get in touch about your own show? Email us: hello@upside.fm Learn more about Upside: https://upside.fm
Interview begins: 7:01 Debrief: 45:09 Sarah Hill is the CEO and Chief Storyteller of Healium. Healium is a virtual and augmented reality tool for the self-management of stress powered by the user's own brainwaves and heart rate. Healium is the world’s first biometrically-powered VR/AR immersive media channel controlled by the user's brainwaves and heart rate via consumer wearables. Hill's XR experiences are clinically validated in 3 peer-reviewed journals and have been viewed more than 7 million times. After 20 years as a TV reporter covering trauma, Sarah’s media diet of reporting the day's headlines ultimately made her sick. Sarah developed Healium for herself as well as the 41 million others who struggle with anxiety. Healium was founded in 2015 in Columbia, Missouri. Learn more about Healium: https://www.tryhealium.com/ Follow Sarah Hill: https://www.linkedin.com/in/sarahhill1/ Follow upside on Twitter: https://twitter.com/upsidefm Key points: - From a TV reporter to being a CEO of Healium 7:51 - Neurofeedback 12:36 - Neuro meditation 18:50 - How is Healium different from other apps 20:48 - New upcoming technology 28:15 - Media diet 29:34 - Team at Healium 32:46 - Digiceutical 35:36 - Healium making money 41:15 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 upside.fm/ethos 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, upside.fm
Interview begins: 6:56 Debrief: 54:04 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 provably 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: https://superrare.co/ Follow John Crain: https://www.linkedin.com/in/johnacrain/ Follow upside on Twitter: https://twitter.com/upsidefm 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 upside.fm/ethos 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, upside.fm
Interview begins: 6:34 Debrief: 51:42 Vanessa is the Co-Founder and COO of Nexme. Nexme is an on demand real estate platform that delivers instant access to homes and full-service, professional real estate agents. All at the click of a button. Nexme charges buyers and sellers a 1.5% commission fee — roughly half of the traditional rate. It connects the site’s users with licensed real estate agents who have at least two years experience and done 10 transactions. Through the agents, it provides home sellers with services including staging, photography and open houses. Buyers and real estate agents have the opportunity to rate each other and properties being listed. The company does not take a commission from sales, but rather charges agents, inspectors, builders and others involved in the process a monthly subscription fee. Nexme was founded in 2019 in Seattle, Washington. Key points: - Analyst transition to product marketing 13:58 - Picking a Startup 16:32 - Moving to Seattle to starting Nexme 19:22 - The becoming of Nexme 28:20 - What is Nexme 29:42 - Balancing the sellers and buyers 36:14 - Nexme in the market 38:36 - Brokerages 40:35 - Starting with Nexme in Seattle 43:55 - Disruption in the real estate world 49:47 Learn more about Nexme: https://nexme.com/ Follow Vanessa Alvarez: https://www.linkedin.com/in/valvarez1010/ Follow upside on Twitter: https://twitter.com/upsidefm 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 upside.fm/ethos 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, upside.fm
Interview begins: 7:18 Debrief: 59:34 Rob Eloff has spent his career investing, living, and working in developing markets. Prior to co-founding Lateral Capital he was a Venture Partner with Conversion Capital and established Frontier Dawn Partners, an evergreen vehicle for capital deployment to early-stage, technology-enabled founding teams in sub-Saharan Africa. Rob started his career in capital markets at JP Morgan, Johannesburg, became an Executive Director at Goldman Sachs and Investment Director at ACI. He spent ten years based in Johannesburg, Moscow, and London transitioning across hedge fund coverage and private equity buyout advisory in markets including sub-Saharan Africa, Eastern Europe, and Latin America. Rob holds a masters degree in finance from Cambridge University and a bachelor's degree with dual majors in philosophy and economics from the University of Cape Town. Key points: - South Africa over the years 9:22 - BRICS 12:35 - Philosophy and Finance 15:51 - Is 10 years time horizon long enough? 17:17 - Lateral Capital 19:51 - Investing across countries 23:51 - Difference and Similarities in investing in Africa to other countries 27:46 - Scorecard in determining the next country 32:39 - Lateral Capital looking for investments 36:59 - Impact of financialization in Africa 50:23 Learn more about Lateral Capital: https://latcap.co Follow Rob Eloff: https://www.linkedin.com/in/rob-eloff-54991b72/ Follow upside on Twitter: https://twitter.com/upsidefm -- This episode is sponsored by Enterprise Rising Conference. This year, Enterprise Rising is October 20-21 and totally online. If you're an enterprise SaaS startup then this will be the best online event you could attend all year. Get your tickets here and use promo code upside to save an additional 20%. – This episode is sponsored by Taft, Stettinius & Hollister, a full-service law firm known for assisting entrepreneurs across the Heartland. Click here to learn more about Taft – This episode of upside is also 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 upside.fm/ethos 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, upside.fm
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