Interview begins: 7:15
Debrief: 55:14

Jackie DiMonte is a partner at Chicago Ventures.

Prior to joining Chicago Ventures, Jackie was a principal at Hyde Park Venture Partners, working with portfolio companies such as RoadSync, Podchaser, Fixer, FactoryFix, and PartySlate. Before that, she worked at Silver Spring Networks (now Itron), an IoT company for critical infrastructure, driving development and pilot projects for emerging smart city technology. 

She is also a member of the Board of Directors for Starting Block Madison and Chicago:Blend and a Venture Partner at Republic.

We discuss:
- Feedback Loop 13:54
- Evolution in a Venture Firm 17:14
- What Level is a Deal Flow Done? 21:46
- Get a Deal Through 24:17
- Programmatic Venture 26:35
- Working Virtually from Austin 31:13
- Partner at Chicago Ventures 35:27
- Inbound Pitches 42:43
- Fragmenting Markets 48:53
- Personal Goals for the role 50:26

Chicago Ventures was founded in 2012.

Learn more about Chicago Ventures: http://chicagoventures.com/
Follow Jackie on Twitter: https://upside.fm/classifieds

Jackie DiMonte of Chicago Ventures // ascending the venture career ladder and opening an office in Austin [CC071]

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."

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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.

[Powderkeg] The founding story of Indianapolis darling startup Lessonly

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.

[When Pigs Fly] #42: Making Medical Bills Bearabill (feat. Lisa Matsuyama & Forest Satterfield of Bearabill)

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.

[Lay of The Land] #15: Justin Bibb (Mayor-Elect 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.

Powerspike // connecting brands and creators on Twitch with a self-serve advertising platform [UP094]

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

Jackie DiMonte of Chicago Ventures // ascending the venture career ladder and opening an office in Austin [CC071]

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