upside

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.

Join the Powderkeg community

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, Twitter

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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.

————

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

————

Subscribe on Apple Podcasts

Connect with Jeffrey on Linkedin or on Twitter

Follow Lay of The Land on Twitter 

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.

Learn more about Powerspike

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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.

–

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

Subscribe to Chicago Capital Podcast
Follow Matt Castellini on Twitter
Learn more about Starting Line
Follow Ezra Galston on Twitter
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Join the upside network

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.

Subscribe to Middle Tech
Learn more about Symba
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Join the upside network

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.

Subscribe to Fast Frontiers
Learn more about Refinery Ventures
Learn more about High Alpha
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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.

Subscribe to 614 Startups
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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.

Follow Alex Bridgeman on Twitter
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Join the upside network

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

Follow upside on Twitter

Advertise with an upside classified

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 with chemicals or preservatives, allowing them to maintain up to 98% of nutrients.

We discuss:

• UBE Attorney 9:31
• Japan Healthcare 14:07
• Law School to Foodnerd 18:05
• Sprouted Foods 23:11
•  Foodnerd 28:18
•  Lab Experience 30:33
•  Foodnerd Funding 38:56

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

Learn more about Foodnerd

Follow upside on Twitter

Advertise with an upside classified

–

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 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.

–

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 savvycal.com/upside and when you're ready to test out a paid plan, use the code UPSIDE to get your first month free.

–

This episode is sponsored by SnapShooter.

Over 40 percent of businesses will suffer a data loss at some point in their history. That’s the type of event that could destroy your business.

SnapShooter is a software as a service that’s built for backups.

SnapShooter has processed over 145 petabytes That’s a staggering amount of data.

New users can setup 1 free backup job with no credit card required. Go and check out their integrations with AWS, DigitalOcean, WordPress, Laravel, CraftCMS and many more.

Use code upside for 10 percent off your first year of SnapShooter. Learn more at upside.fm/snapshooter.

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-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.

We discuss:

• Executive Recruiting During Pandemic 6:19
• Proximity Matters 8:49
• DEI (Diversity, Equity and Inclusion) 13:28
• Compensation Factor 16:50
• National Companies on Remote Hiring 21:38

Learn more about SPMB

Get in touch with Sam

Follow upside on Twitter

Advertise with an upside classified

–

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. 

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.

Learn more about Firebrand

Follow upside on Twitter

Advertise with an upside classified

–

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.

–

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.

–

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 savvycal.com/upside and when you're ready to test out a paid plan, use the code UPSIDE to get your first month free.

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.

Learn more about Republic

Follow Ken on Twitter

Follow upside on Twitter

Advertise with an upside classified

–

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.

–

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.

–

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 savvycal.com/upside and when you're ready to test out a paid plan, use the code UPSIDE to get your first month free.

–

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

SavvyCal was founded in 2020 in Minneapolis, Minnesota.

Learn more about Savvycal

Follow Derrick on Twitter

Follow upside on Twitter

Advertise with an upside classified

–

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.

–

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.

–

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 savvycal.com/upside and when you're ready to test out a paid plan, use the code UPSIDE to get your first month free.

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 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.
–

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.

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 has offered diversification benefits in both good times and bad times. In 2008, the S&P 500 dropped 38%, while wine remained stable.

Vint takes a small sourcing fee for each offering. Vint also purchases between 0.5% and 10% of each offering.

We discuss:

• Value vs. Growth Investing 8:49
• Vint's Concept 13:53
• Wine Industry 17:51
• Wine Investment 21:42
• Future of Wine Trading 24:35
• Catalysts 29:47
• Whiskey Market 33:55
• Approach on Getting Experts 38:52

Vint was founded in 2019 in Richmond, Virginia.

Learn more about Vint

Follow upside on Twitter

Advertise with an upside classified

–

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.

–

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.

–

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 savvycal.com/upside and when you're ready to test out a paid plan, use the code UPSIDE to get your first month free.

–

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.

Click here to visit our Product Hunt campaign

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 the industry, and they enjoy challenging traditions. They invest broadly, and our unique, analytical approach to venture investing aims to reduce the risk, while maintaining the high returns typically associated with this stage of investing. They emphasize our expansive networks, and thrive on collaboration - helping to syndicate deals, encouraging fair terms as a best practice, and prioritizing relationships. 

A Kauffman Fellow (Class 22) and former leader in Hyde Park Angels, Victor founded M25 in 2015 and quickly grew it to become the most active venture firm in the Midwest. 

We discuss:

• Generational Entrepreneurship 12:27
• Starting small with VC 19:04
• Value Negative Capital Before 21:36
• Angel Groups Before and Now 23:51
• Knowing the Best Deals in the Region 26:18
• M25's Model 29:46
• Maintaining Reputation 33:50
• Trending Opportunities in the Midwest 37:58
• Concerns in the Midwest 41:11
• Expanding beyond the Midwest 44:52
• Midwest on Early Stage VCs 52:28
• M25 Summit 55:07

M25 was founded in 2015 in Chicago, Ilinois.

Learn more about m25
Follow Victor on Twitter

Follow upside on Twitter

Advertise with an upside classified

–

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.

–

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.

–

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 savvycal.com/upside and when you're ready to test out a paid plan, use the code UPSIDE to get your first month free.

–

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 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.

Learn more about AireXpert

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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.

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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.

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