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 culture has always been a North Star in the companies evolution. Max and Conner both started their professional career by means of the Orr Fellowship, a two-year, Indianapolis-based fellowship focused on developing the next generation of business leaders and entrepreneurs. Max began working on Lessonly after winding down his first startup. Conner was working in sales at ExactTarget (acquired by Salesforce) at the time. The two were roommates and Conner became an early adopter of the original Lessonly platform, where he used it to help train an international sales team of ExactTarget. Learn more about the Lessonly journey and hear the words of wisdom this dynamic duo has about growing a high-performing, venture-backed tech company. If you like this episode, please subscribe and leave a review on iTunes. You can also follow on Soundcloud or Stitcher.

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.

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.

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, enabling brands to create an influencer campaign just like they'd make a media buy. The process takes 4 minutes or less, and saves the average brand over 150+ hours of work. There's no negotiating, no having to tediously search through lists of thousands of influencers, and most importantly, no heavy lifting. Simply tell PowerSpike what you want, and it delivers results. We discuss: - Twitch back in 2014 12:35 - Getting Brand Sponsorships 20:21 - Pitch Model Pre Techstars 22:25 - Pitch in Today's time 23:10 - Brand Safety 26:39 - Creator's Inventory Management 30:18 - How to be on Powerspike 33:40 - Creator's on Powerspike 34:48 - Building the Marketplace 38:02 - Powerspike's Business Model 40:24 - Best for Powerspike 41:48 Foodnerd was founded in 2015 and based in New York City.

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 podcasting after college. He finally decided to start one when I saw an opportunity to spotlight a city that I felt was not receiving the national recognition it deserved. Matt is also the author of Venture Scenes, where I blog about Startups, Venture Capital, and Movies. Ezra Galston is the Founding Partner at Starting Line, a Chicago-based early-stage venture capital firm that invests in leading consumer products and brands. In this episode, they cover: Fundraising Resiliency Starting Line Fund II Building to Conviction Post-Investment Value-Add The Challenges of the VC Feedback Loop State of Chicago Tech

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.

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 content every month. ShareThis, based in Palo Alto, CA, was one of the fastest growing companies in the country, growing to $50 million in less than four years which earned him the EY Entrepreneur of the Year in his region. Tim also launched and managed Cintrifuse, one of the best performing fund of funds in the country, investing in 15 top-tier early stage funds across the U.S. Tim has been in venture capital since 1998. In this episode from December 8, 2020, Tim interviews Scott Dorsey, co-founder and managing partner at High Alpha, a venture studio in Indianapolis. Scott is the former CEO and co-founder of ExactTarget, which was acquired by Salesforce in 2013 for more than $2.5 billion dollars. A couple of powerhouses in this episode! You can learn more about Refinery Ventures at refinery.com. OK, enjoy this episode of Fast Frontiers, right after this.

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 are sending will contribute to their loved ones wellbeing. Fleri is changing that by allowing immigrants to purchase health insurance for the loved ones creating a win-win-win-win situation for the policyholder, patient, doctors and insurance companies. First, the policyholder knows that they are providing access to high-quality healthcare for their loved one and they can see what treatments have been received. Next, the patient has access to vetted physicians and receives care in clinically sound facilities. The doctors are able to treat patients with the ability to pay thereby providing capital for infrastructure investment and finally, insurance companies have the premiums to build robust networks and offer more affordable plan options. Fleri is building a commercial solution to what has been an intractable problem in the developing world by creating a robust healthcare insurance ecosystem with incentives for all stakeholders.

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 other partners. Badge has invested in over a hundred searchers and has extensive experience as both an investor and operator. WSC’s seven-person team is based in Charlotte, North Carolina and is investing and of its second fund, a $100 million fund closed earlier this year focused on the traditional search fund model. During our discussion, we talk about turning Stone Pump & Trench around, lessons learned from over a hundred search fund investments, a few notable companies, he’s been a part of, what’s typically missing in a new company, and a wide range of discussion on board construction and usage for entrepreneurs and investors alike. This episode is fantastic and I learned a ton and I think you will too.

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 share how we’re continuing to build the upside network behind the scenes.

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% of nutrients. Foodnerd was founded in 2017 and based in Buffalo, New York.

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 work with companies specializing in: - Technology - Consumer - Media - Finance - Health - Sustainability ...and more They bring the knowledge of a large, global firm and combine it with the personalized service and attention of a boutique. SPMB has been doing this for a long time. And they are bringing their Silicon Valley success and heritage all across the country. They have a dedicated team focused on serving clients in the Mountain West and Midwest emerging tech markets. They have successfully relocated dozens of top-tier candidates from the East and West Coasts to the Central US and Canada – including Chicago, Indianapolis, St. Louis, Bozeman, Phoenix, Edmonton, Toronto, Denver, Boulder, Austin, Salt Lake City, and beyond.

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 through Techstars programs have raised a total of over $9 billion in funding and have a collective market cap of over $25 billion. Prior to Firebrand, Chris was the Founder and Managing Partner of Blue Note Ventures, an early-stage venture fund investing in great technology companies and serving entrepreneurs committed to authentic leadership. After co-investing in several companies together out of their respective funds, it became obvious that Chris and John not only shared a similar investment strategy, but also an underlying set of values around how they partnered with entrepreneurs. In late 2019 they decided to join forces and merged Firebrand and Blue Note.

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. Previously, Ken was the General Counsel for Angel List from 2014-2016. We discuss: -Ken on AngelList as Non-Engineer Role 8:52 - AngelList Syndicates 10:00 - JOBS Act 12:57 - Republic's Launch Timing 18:01 - Republic's Mission 22:04 - Republic's Business Model 24:51 - Equity Crowdfunding 29:10 - Focusing on the Product Experience 32:31 - ROI in Crowdfunding 35:35 - Upside from Retail Deals 42:47 - Arbitrary Cap 43:58 Republic was founded in 2016 in New York City, New York.

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 is learning building the company. We discuss: - Starting at the software industry 11:15 - Drip Before SavvyCal 14:35 - Business Takeaways 17:21 - Sexy Software Business 19:43 - Idea on SavvyCal 21:01 - SavvyCal Reaching it's Market 24:06 - What's Weird About Scheduling Links 28:42 - SavvyCal's Feedback 30:47 - SavvyCal and it's Competitors 34:25 - SavvyCal's Indefinite Free Trial 39:51 - Hybrid Bootstrapper 42:59 - SavvyCal Wanting To Be A Multi-million Business 46:08 - Minneapolis Startup 50:38

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 makes Rootine? 11:52 - Rootine personalizing your vitamins 16:53 - Results with Rootine 20:20 - Rootine earning as a business 21:14 - Commercializing Rootine 26:51 - Raising capital for Rootine 27:44 - Data privacy and security 29:55 - Rootine's Demographics 35:30 - Distribution 37:40 – 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

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.

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.

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.

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 risk of FAA compliance. Andy has been an aircraft maintenance guy & aviation geek since 1989. A founding member of the AireXpert crew, he’s worked in Tech Ops and on the heavy iron for several decades. We discuss: - Airplane Maintenance 10:49 - Idea Behind AireXpert 13:20 - Aviation Business Model 17:34 - Outsource Maintenance 20:03 - Airline Maintenance Process 22:53 - AireXpert 27:39 - Evolution of AireXpert 28:42 - Target Airlines 30:22 - Operational Validation 33:22 - Pricing Model 35:44 - AireXpert and 3rd Party Vendors 39:55 - AireXpert Funding 45:36 AireXpert was founded in 2018 in Buffalo, New York.