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.

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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.

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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!

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Justin Bibb is a proud Cleveland native who grew up in Mt. Pleasant on the southeast side of the city. He has dedicated his career to rebuilding neighborhoods and making cities safer, healthier, and more resilient. Justin currently serves as the Chief Strategy Officer of Urbanova, a start-up focused on solving the unique challenges faced by mid-sized cities.

Over the last 15 years, Justin has worked at the intersection of government, business, and the nonprofit sector as an executive and nonprofit leader. He interned for President Barack Obama when he was in the U.S. Senate and has served as Special Assistant for Cuyahoga County, Head of the Global Cities Practice at Gallup, and most recently, Vice President for KeyBank.

He co-founded Hack Cleveland in 2014 following the death of Tamir Rice and launched Cleveland Can't-Wait in 2019, a nonprofit focused on advancing racial equity and economic opportunity in underserved neighborhoods across the city. Justin also serves on the boards of the Greater Cleveland Regional Transit Authority, Teach for America – Ohio, Destination Cleveland, and LAND Studio Inc.

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Learn more about Justin’s Candidacy: https://www.bibbforcle.com/

Follow Justin on Twitter: https://twitter.com/JustinMBibb

Follow Justin’s Campaign on Twitter: https://twitter.com/BibbForCLE

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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 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 is based in New York City.

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This episode of upside is sponsored by SPMB. 

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 can do the same for you. 

Visit upside.fm/spmb to learn more.

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This episode of upside is sponsored by En Blazes. 

En Blazes is an Operations Strategy Agency that prepares your org for scale.

They’re offering a free guide to growing your team from experts in hiring, off-shoring, and diversity. You'll also receive a mini-course on valuing your business for sale.

Visit scale.enblazes.com to learn more.

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This episode of upside is sponsored by GoingVC. 

The good folks over at GoingVC, which was cofounded by our friend and past guest, John Gannon, have published a BUNCH of papers, guides, models, and all this amazing content to help people learn about VC trends and prepare for interviews - there's even stuff on how to get started as an Angel or early-stage investor.

Subscribing is a steal at less-than $200 PER YEAR. So sign up TODAY if you want to start your venture capital career TOMORROW - and be sure to use the discount code UPSIDEFM for 20% off your first year.

Visit goingvc.com/research to learn more. 

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

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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. Evan and his experienced co-founders are bringing a fresh perspective and modern software to the real estate industry which is notorious for being slow to adopt new technology. We discussed Evan's journey to becoming a startup founder, how he got his early start in real estate, his approach to building a rockstar team, and Symba's unique marketing approach.

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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 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.

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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 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.

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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 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.

You can subscribe to Think Like An Owner on iTunes, Spotify, Google Podcasts, Stitcher, Breaker, and TuneIn.

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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 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.

Learn more about the upside network

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