Tech In Chicago on Smash Notes

Tech In Chicago podcast.

May 16, 2020

Tech In Chicago takes you inside the Chicago tech world. Each week Colin Keeley is joined by Chicago’s top startup founders and venture capitalists to talk about the amazing companies being built right here. Visit TechInChicago.co for more information.



Recently updated notes

Dave Bowen is the CEO of Purchasing Platform, an online marketplace for real estate developers to buy products for their properties. Before Purchasing Platform, Dave was the founder of Market Maker 4 (MM4), an e-sourcing tech startup, which he bootstrapped and sold for $22M in 2016. In this episode he talks about the pros and cons of bootstrapping a business, how to run a two-sided marketplace, and the pains and strategies for B2B sales.

Updated on May 16

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Sterling Douglass & Justin McNally, Co-Founders of Chowly, a restaurant technology company that integrates third-party online ordering platforms with restaurants' point-of-sale (POS) systems. 

Sponsored by:

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James Yi is the Founder and CEO of LeafTrade, a startup building a wholesale ordering platform connecting licensed cannabis vendors and dispensaries. Before LeafTrade, dispensaries were doing most of this work manually with emails, calls, and spreadsheets. With Chicago legalizing recreational cannabis it seemed like a perfect time to have James on. They also recently announced a $4.5M seed round.

Sponsored by:

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Stuart Frankel is the Founder & CEO of Narrative Science, which translates all the data companies produce into digestible information. The company started out producing software that turned raw baseball scores into stories for reporters. They have raised $43.4M in funding and have reinvented themselves multiples times in their decade plus in business.

Sponsored by:

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Konrad Waliszewski is the CEO and a co-founder of TripScout, a startup making a travel app that curates the best recommendations around the world and provides trip-planning tools. Konrad, a long time digital nomad, has visited 100 countries and Forbes has called him a “modern day Marco Polo.” Prior to TripScout, he was the COO of Speek, which raised $6m in venture capital and was acquired by Jive. Follow his adventures on Instagram.

Sponsored by:

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Steven Galanis is the Founder & CEO of Cameo, a startup that allows you to book personalized shoutouts from your favorite people. Cameo has raised over $65m in VC funding with a reported $300 million valuation from some big names including Kleiner Perkins, Lightspeed, and Spark Capital and Chicago’s very own Chicago Ventures, Origin Ventures, and Starting Line. Before founding Cameo, Steven was a film producer, account executive at LinkedIn, and an options trader in Chicago.

Sponsored by:

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Brian Bar is the Founder and CEO of Victory Lap, a sales bootcamp empowers candidates from all different backgrounds to find success in sales.

Before launching the business, Brian served as the VP of Sales for ThinkCERCA, where he devised a national distribution strategy, while simultaneously building out the sales organization. This experience, coupled with his work creating Groupon’s sales onboarding department (overseeing the hiring and development of over 1,000 entry-level sales representatives) led Brian to start Victory Lap.

He is a sought after expert for companies hiring, training, and managing Gen Y and Gen Z sales talent. Brian lives with his wife, daughter, and dog in Chicago, and enjoys summers in his hometown of Long Beach, IN.

Sponsored by:

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Jeff Hunt is the Founder of Snap36, a 360° product-photography startup that works with everyone from Amazon to small, family-owned businesses to optimize their e-retail photography.

Jeff got his start in the late 70s as a Kodak salesman and worked his way up the corporate ladder to the leadership team for Adobe’s European division.

But he always had an entrepreneurial streak. He launched three startups in the 90s. Two went public. One went from zero to $55 million in two years and then $55 million to zero in two months with the dot-com bust.

In 2008, with the world economy in a tailspin and e-commerce in its infancy, Jeff made his final leap of faith, quitting Adobe to launch Snap36.

The company now has big clients in a range of industries (manufacturing and automotive to CPG and footwear) and boasts millions in revenue.

 

Sponsored by:

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Brian Luerssen is the CEO & Tim Grace is the COO of DraftBit, a startup building a new way to build cross-platform, native iOS and Android apps in minutes instead of months, and they are both Venture Capitalists at LongJump Fund, a first-check venture fund designed to invest in the best new founders right when they begin their journey.

Before Draftbit, Brian was a Managing Director at Techstars and Tim was Head of Product at Trunk Club.

Sponsored by:

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Tom Smith is the Co-Founder of Truss, a commercial real estate platform that helps small businesses find office space. You can think of them as Airbnb for commercial real estate.

The company's marketplace allows one to find, explore, compare, lease and tour office, industrial and retail space, immediately receive feedback on tours and spaces, manage all documents in one place, among others, providing small and medium businesses with a cost-effective way to lease space for their business.

Truss has raised about $23 million since it was founded in 2016 with it’s most recent round led by Boston-based General Catalyst, who was also an early investor in Airbnb.

Other backers include Navitas Capital, Hyde Park Angels and Hyde Park Venture Partners, along with Jeff Boyd, the former CEO of Priceline, and Robert Mylod, a former Priceline executive and the chairman of Redfin.

Sponsored by:

Starting Line VC: A new Chicago-based venture capital firm, founded by Ezra Galston, one of our top early podcast guests and trusted partner of many of Chicago’s hottest startups. Check out what they’re up to at StartingLine.vc.

 

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Ashish Rangnekar is the CEO and Co-Founder of BenchPrep, a SaaS learning platform for education and training companies to create and deliver personalized digital learning programs across multiple devices.

They have helped millions of people all around the world learn better and faster by leveraging the power of technology.

The world’s leading education organizations, including ACT, Hobsons, McGraw Hill Education, HR Certification Institute, Houghton Mifflin Harcourt and Cliffsnotes use BenchPrep to help learners improve outcomes.

The company has raised more than $22M in venture capital funding from industry leading investors including New Enterprise Associates (NEA), Jump Capital, Revolution Ventures and Lightbank.

Ashish is interviewed by Paul Lee, Founder and General Partner of Builders VC, a $200M early stage venture fund, and formerly a General Partner at Lightbank, an early investor in BenchPrep.

 

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Gabriel Wyner is the Founder and CEO of Fluent Forever, a startup that aims to help anyone learn a language quickly and remember it forever. He launched a bestselling book 4 years ago and now has the most successful app Kickstarter of all time for his Fluent Forever app. As of this episode, he has raised over $430,000 and he still has another week left. 

Gabe is not your typical founder. He is a former opera singer/engineer who has a passion for learning new languages and just recently got thrown into the tech and startup world. He has a lot of great advice and brings a unique perspective to not only learning languages, but also building products. 

In This Episode You Will Learn:

  • Why Gabe had to learn multiple languages to become a better opera singer
  • How lying on a french test led to his discovery of spaced repetition
  • Why starting by translating a language is the wrong approach to learning new languages
  • Gabe speaks eight languages but doesn't believe he has an innate skill for it
  • The importance of learning pronunciation at the start
  • How he decided to make an app after having a successful book and flashcards
  • The value in making flash cards yourself
  • How he thinks about budgeting and spending the Kickstarter money
  • How Gabe approaches bootstrapping vs raising money for his company 
  • Gabe's view on the future with translation services and whether the desire to learn languages will ever wane
  • Why founders need to develop a circle of advisors

Favorite Books:

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Chris Gladwin is the CEO and Founder of Ocient, a startup building software that enables sophisticated users of data to handle massive amounts of information fast enough to make real-time decisions.

Two years ago Chris sold his data storage company Cleversafe to IBM for $1.3 billion. Cleversafe was the largest and most strategic object storage vendor in the world. The technology he started generated over 1,000 patents granted or filed, creating one of the ten most powerful patent portfolios in the world.

Prior to Cleversafe, Chris was the Founder and CEO of startups MusicNow and Cruise Technologies, and led product strategy for Zenith Data Systems. He started his career at Martin Marietta, and holds a mechanical engineering degree from MIT.

In This Episode You Will Learn:

  • The story of Chris’s senior prank and the lessons around forming a team, have a vision, and setting goals that translate to being an entrepreneur
  • The importance of not being too far ahead of the market and how you know if you have the timing right?
  • His experience developing a tablet computer 20 years before the iPad
  • Why Cleversafe was able to get a multiyear head start on everyone else in the industry 
  • How storage worked before Cleversafe
  • Why Peter Barris, Managing General Partner at New Enterprise Associates, doesn’t think Cleversafe could have happened in Silicon Valley
  • How the sale to IBM came about
  • Why you want to be bought not sold
  • What it was like delivering the news of the sale of Cleversafe to everyone
  • The impact on the Chicago ecosystem of the Cleversafe exit minting 80 new millionaires
  • How Chris landed his first reference customer for Cleversafe
  • How Chicago tech has changed since his first company in geography and scale
  • Why we still need a Chicago tech anchor
  • Chris's thoughts on Chicago's potential for Amazon HQ2 and what they should be indexing on
  • Why Chris requires 5-8 nonstop flights a day to any satellite office location
  • Chicago's biggest advantages over Silicon Valley? talent cost and talent retention
  • The similarities between being a founder and a poker player
  • Why you have to put yourself in a position to realize your ambition
  • What Chris focuses on? Building the team, raising money, and building a pipeline of customer information and feedback into the company 
  • The similarities between being a founder and a journalist

Favorite Books:

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Rebecca Sholiton and Nate Cooper are the Co-Founders of Wise Apple(formally Pak'd), a startup that delivers pre-made, customizable school lunches directly to families’ homes.

They just announced their $3.6 million seed round led by Pritzker Group Venture Capital and Levy Family Partners with Chicago Ventures, Greycroft Partners, BoxGroup and Irish Angels also participating.  Wise Apple was also part of Techstars Chicago class of 2016 which included previous podcast guests Bright and PartySlate

Use code "chicagotech" for $20 off your first week or this link for it to be automatically applied. 

 

In This Episode You Will Learn:

  • The inspiration behind Wise Apple
  • How they made their first lunches
  • How they collected 300 emails from interested customers on day 1
  • The importance of customizations to their business
  • The value of hand delivering your orders and collecting feedback
  • How they balance healthy and tasty for kids
  • How a new porn site led to the name change
  • What it was like working with the legendary Red Antler branding agency in New York 
  • Why Wise Apple won out as the name
  • Any concern around going with a name without having the .com locked down
  • How influential their Kellogg MBAs have been and whether they think they needed it
  • Why starting a business with a bunch of MBAs is a mistake
  • How Rebecca and Nate met
  • Whether copycats and competitors in the food space is a concern for them
  • How their space differs from the meal kit business
  • How they arrived at their price
  • The value in going through Techstars
  • The importance of balancing realistic numbers and unit economics  with a big vision
  • Why we need more female investment professionals
  • Why Rebecca won’t look at resumes unless there are non-white/male resumes included
  • The value in having a big anchor tech company in Chicago

Selected Links From The Episode:

Favorite Books:

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Brian Barnes is the CEO and Founder of M1 Finance, a startup making an automated investment tool that lets users put their money to work in a balanced portfolio without the hassle of actually managing it.

Just a few years after graduating from Stanford, Brian raised $9 million and moved back to Chicago to build the platform. 

In This Episode You Will Learn:

  • The motivation behind Brian starting M1 Finance
  • How Brian went about launching a MVP in the heavily regulated finance industry
  • How Brian raised $9 million pre-launch 
  • The benefits of robo-advisors over all ETFs
  • What M1 Finance costs and how they plan to differentiate from other robo-advisors
  • How Brian got his first customers
  • What Brian has learned about life and business from his mom Brenda Barnes, Former CEO of Pepsi and Sara Lee?
  • What the most effective marketing channels have been
  • How M1 Finance's message has evolved over time
  • How to communicate a relatively complicated product to consumers quickly
  • The importance of design in fintech 
  • Why Brian moved back to Chicago after going to Stanford and whether he thinks it matters
  • Why Chicago has to improve our risk appetite

Selected Links From The Episode:

Favorite Books:

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Michael LaVitola is the CEO and Founder of Foxtrot, a startup that could be thought of as a curated cornerstore with on-demand delivery. It is basically what you imagine your ideal convenience store would look like with an in store cafe and a ton of super cool beer, wine, food, gifts, and basic necessities. 

Use code "ab079e" for $10 off your first order

In This Episode You Will Learn:

  • Why Michael decided to start Foxtrot
  • What the first version of the product looked like
  • Why they moved away from on demand to retail
  • Why they splurged on pricey retail spots
  • Why they will be having a coffee bar in all their stores going forward
  • How they curate the products they stock
  • What are their best selling and weirdest products
  • What Michael thinks of Amazon's acquisition of Whole Foods
  • What the future of retail looks like
  • How they plan to differentiate themselves from Amazon's offerings
  • Why it is important to know who your ideal investor really is

Selected Links From The Episode:

Favorite Books:

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Julie Novack is the CEO and a Co-Founder of PartySlate, a startup building a two-sided platform that allows event professionals to share their work and party hosts to gain inspiration from it. 

PartySlate has raised $2.6 million from investors including Hyde Park Venture Partners, Hyde Park Angels and InvestHER Ventures.

In This Episode You Will Learn:

  • Julie's motivation for starting PartySlate
  • The importance of throwing a great party for fundraisers
  • The wildest party someone has thrown using PartySlate
  • How to use content marketing and promotional events to drive traffic
  • Why you have to "super-please" one side of the market to start a two-sided marketplace
  • How PartySlate decides where to focus their content marketing efforts
  • The biggest benefits of going through Techstars
  • What Julie would like to see Chicago tech improve on
  • How we get more women involved in tech
  • The importance of role models for women in tech
  • The hardest thing about selling
  • The 3 most critical elements to being a high performing salesperson
  • What made her leave a large company for the startup world
  • The value of dreaming outloud about your idea
  • The fallacy of being protective about your idea
  • How Julie decided to expand geographically before proving out the business model in one geography
  • What their process looks for expanding in to new geographies
  • The importance of owning and managing technology
  • Advice for planning a great wedding

Selected Links From The Episode:

Favorite Books:

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Jeff Kahn is a Co-Founder and CEO of Rise Science,  a sleep behavior change startup that provides sleep coaching for elite athletes. They harness the science behind sleep, and give elite athletes the power to perform at their best with the help of continuous, personalized insights, guidance and feedback.

Rise Science is currently working with many major sports organizations like the Chicago Bulls, Jacksonville Jaguars, Miami Dolphins, West Virginia Mountaineers, and Tennessee Volunteers. Jeff's research and work has been featured in the NY Times, ESPN and the Wall Street Journal. 

In This Episode You Will Learn:

  • How the idea for Rise Science came about
  • What the first version of their sleep tracking looked like
  • How to determine how much sleep you personally need
  • Comparing different sleep tracking tools
  • The compliance rate with professional players
  • Why they sell the players on sleep tracking and not the coaches
  • What kind of performance improvements teams are seeing
  • What the ideal nap looks like
  • Whether morning (larks) or night (owls) people exist
  • Do owls or larks have a performance advantage in life/sports
  • The most common sleep mistakes athletes make 
  • How do justify $80-100k a year to GMs of professional teams
  • What Jeff’s sleep habits look like 
  • How you can improve your sleep

Selected Links From The Episode:

Favorite Books:

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George Souri is the Founder and CEO of LQD Business Finance, a startup providing quick, convenient, and affordable financing to small and medium-sized businesses that are traditionally underbanked. LQD is leveraging data to offer business loans in the $250,000 to $3 million range to help businesses scale faster. 

George is a serial entrepreneur, self-taught mathematician, and musician. He got his entrepreneurial start with a string of dance clubs at 18 years old before founding his own investment bank.

In This Episode You Will Learn:

  • What is alternative business lending
  • Why you should try to disprove your idea
  • How George got his start in entrepreneurship
  • The importance of viewing failure as opportunity
  • The power of small efficient actions
  • Why banks turn down good companies
  • How LQD made its first loans
  • The differences between consumer and business lending
  • The value of doing an autopsy on a business
  • The biggest red flags LQD sees when examining a business
  • Why you should be trying to find people that make you feel dumb

Selected Links From The Episode:

Books Mentioned:

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TroyHenikoff.TechInChicago.Podcast.jpg

Troy Henikoff is the Managing Director at Techstars Chicago, a Managing Director at MATH Venture Partners, and a Professor of Entrepreneurship at Northwestern University's Kellogg School of Business. If you haven't heard of Troy yet, he is one of the biggest figures in the Chicago tech scene and has been instrumental in getting Chicago tech to where it is today. He is also one of the nicest guys you will ever meet and a hard core cyclist. 

Prior to launching Techstars Chicago, Troy was a serial entrepreneur. He was the CEO of OneWed.com, President of Amacai, and co-founder and CEO of SurePayroll.com. Troy built the technology for Jellyvision (creators of “You Don’t Know Jack!”), was the President of Systemetrics, and his first company was Specialized Systems and Software. Troy has an undergraduate degree in Engineering from Brown University and a Masters Degree in Project Management from Northwestern.

In This Episode You Will Learn:

  • How cold is too cold when biking to work
  • The story of how Troy got into entrepreneurship
  • How Excelerate Labs came about
  • The story of creating BB8 for Star Wars
  • What the application process is like for Techstars
  • How to find the right balance between tenacious and coachable
  • Which entrepreneurs get the most out of Techstars 
  • What the timeline looks like for their 90 days in the program
  • What goes into making a perfect pitch in front of 500 venture capitalists
  • What companies really excite him
  • Why Mark Achler and Troy started MATH Venture Partners
  • Whether or not there is a signalling problem by only investing in some of your accelerator companies
  • Why Groupon would have been impossible to build in San Francisco
  • Why you have to be honest with yourself first

Selected Links From The Episode:

Favorite Books:

Sponsored By:


  • Propllr: a Chicago public relations firm that helps startups and innovators build credibility and awareness for their companies, people, products and services.

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Greg Tepas is the Founder and CEO of CarAdvise, a startup that makes car maintenance easy and transparent. CarAdvise acts as a personal auto repair concierge and advisor for car owners. They provide an unbiased opinion on proposed work and estimated cost to save car owners from the traditional mistrust and stress associated with car repairs. 

In This Episode You Will Learn:

  • Why Greg decided to build CarAdvise
  • How commercial car fleets typically handle repairs
  • How to begin building a two sided marketplace
  • How CarAdvise makes money
  • How the product has evolved
  • Impact of self driving cars on the car repair industry
  • Why you should be talking to everyone about your startup

Favorite Books:

Sponsored By:


  • Propllr: a Chicago public relations firm that helps startups and innovators build credibility and awareness for their companies, people, products and services.

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Jeff Judge is the Founder and CEO of Bright, a startup that helps SaaS companies quickly understand their core metrics, and gives them the tools to grow faster. Bright just graduated from the 2016 Techstars class here in Chicago. Before founding Bright, Jeff cofounded and led Signal (acquired) and he was an early engineer at Orbitz. 

In This Episode You Will Learn:

  • Why Jeff founded Bright after selling Signal
  • What kind of optimizations Bright can deliver
  • What setting up Bright entails
  • Why he applied to Techstars as an experienced founder
  • What he got out of the Techstars accelerator
  • Why he is a big fan of having a distributed team
  • The tools Jeff finds helpful to make a distributed team work
  • Why he would have raised money earlier 
  • Why he’d like to see Chicago tech be more collaborative
  • The motivation behind starting the Bright conference
  • How to plan a successful conference in just two weeks
  • What goes into making the perfect pitch
  • The importance of having the right support structure in enterprise selling
  • The value of submitting imperfect creations

Selected Links From The Episode:

Favorite Books:

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Rob Royer is the Founder and CEO of Interior Define, a startup that builds furniture on demand and will customize everything, including the size, shape, color, fabric, filling, and frame.

Rob was one of the early employees at Bonobos and took much of what he learned over to Interior Define, which he launched in 2014. Shopping for a big purchase like a couch online without sitting on it beforehand kind of seems crazy so we talk a lot about how they have gotten people over that hesitation. We actually recorded this episode sitting on one of their sofas in their Lincoln Park guideshop. 

In This Episode You Will Learn:

  • How Rob got involved with Bonobos
  • What he learned at Bonobos and brought to Interior Define
  • How he got into the furniture industry
  • The importance of partnerships in the lifestyle space
  • Why they added customization options
  • How they got PR in their early days
  • How do they convince someone to spend thousands of dollars on a sofa they haven’t seen in person
  • The importance of having a guide shop as an online brand
  • What their most effective marketing channels are today
  • How they picked the location of their guide shop
  • The benefits of having the office directly above the guide shop
  • How to sell a big potential hire from a larger company on working at a startup
  • Future products that Rob’s excited about 

Selected Links From The Episode:

Favorite Books:

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Mia Saini & Laura Lisowski are Co-Founders of Oars + Alps, a new e-commerce startup selling men’s skincare products that target an "athleisure guy on the go". Their first products are a face moisturizer, a deodorant, and a face wash in stick form. 

Mia Saini is a graduate of MIT and Harvard Business School and a former reporter for Bloomberg TV. Early last year, Mia quit her job at Bloomberg and her Co-Founder Laura Lisowski quit her job at Facebook to start building Oars + Alps out of 1871.

In This Episode You Will Learn:

  • The difference between men's and women's skin care
  • How they decided to start with these products
  • Where the name comes from
  • How they met on a party boat in Thailand
  • The benefits of being an outsider in the industry
  • How they choose ingredients
  • Why you have to set the price before making product decisions
  • What men are doing wrong in their grooming
  • How they plan to cut through the noise and get the word out
  • How they position their brand
  • Another startup brand they look up to
  • The value of content and influencer marketing
  • How they landed features in Esquire and Bloomberg within months of launching and how you can to

Selected Links From The Episode:

Sponsored By:


  • Propllr: a Chicago public relations firm that helps startups and innovators build credibility and awareness for their companies, people, products and services.

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Zach Kaplan is the Founder and CEO of Inventables, which makes software and hardware for 3D carving. Their flagship products Easel, Carvey, and X-Carve are used by a new wave of makers to make everything from circuit boards to skate boards. Zach was named a “modern Leonardo” by the Museum of Science and Industry and a 40 under 40 by Crain’s Chicago Business. Inventables has the stated goal of putting a 3D carver in every classroom by the end of the decade.

In This Episode You Will Learn:

  • The differences between carving and 3D printing
  • What can you make with a 3D carver
  • Who is buying and using these carvers
  • How they prepared to raise $600k on Kickstarter
  • How they plan to get a 3D carver in every school by the end of the decade
  • Why they decided to make their very expensive software free
  • How they plan to make money while giving away software
  • What the future of 3D printing and carving is
  • What will be the result of having all these carvers available

Favorite Book:

Multipliers: How the Best Leaders Make Everyone Smarter by Liz Wiseman

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Amanda Lannert is the CEO of Jellyvision, which makes ALEX, an interactive decision-support tool that talks you through traditionally boring and confusing human resource decisions like picking health insurance and makes them fun and engaging. The Jellyvision of today has one of the more interesting founding stories, which Amanda describes in the beginning of this episode. It was born from the ashes of You Don't Know Jack. 

Amanda was named CEO of the Year at the Moxie Awards in 2014 and 2015. Under Amanda’s leadership, Jellyvision has doubled its revenue three out of the last four years.

In This Episode You Will Learn:

  • How Jellyvision got into the B2B space
  • The value of a liberal arts background in tech
  • How Jellyvision got its first customers
  • Keys to selling to big businesses
  • How their product evolved and what eventually led to growth
  • How important humor is to their brand
  • Whether their diversity is intentional or accidental
  • How they are trying to improve diversity
  • How they attempt to identity redact interviews
  • How to build a strong culture across team members of different generations
  • The impact of remote workers on their culture
  • How Jellyvision caters to introverts in an extroverted office
  • Amanda’s favorite interview questions
  • How they ended up with a room dedicated to a massage chair
  • Why Amanda would like to see more audacious dreams from Chicagoans
  • How to find mentors
  • What is the best bang for your buck networking

Selected Links From The Episode:

A Few of Amanda's Favorite Books:

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Eddie Lou is the CEO and Co-Founder of Shiftgig, a mobile, two-sided labor marketplace connecting large venues in the service and hospitality industries with locally available and previously vetted hourly workers. Shiftgig is one of the leaders in the gig economy, acting as a technology bridge connecting millions of workers with millions of shifts. 

Shiftgig has raised $35M in venture funding from many local VCs including Chicago Ventures, Pritzker Group Venture Capital, and Corazon Capital. 

Before founding Shiftgig, Eddie was a general partner with OCA Ventures, where he invested in software, consumer internet, and business services companies. 

In This Episode You Will Learn:

  • Why Eddie started Shiftgig after being a venture capitalist for many years
  • Who are the people working in the gig economy
  • What have been their most interesting gigs
  • How they got their first customers
  • How they pivoted away from their social network idea
  • How they dealt with a business model that wasn't working and struggling to raise capital
  • Eddie’s keys to building a two-sided marketplace
  • What he’s learned as a VC that has benefited him as an entrepreneur
  • Why he would like more series B investors in Chicago
  • Why he would like to see more risk taking from executives
  • Why Shiftgig acquired BookedOut
  • What's the future of the gig economy
  • What's next for Shiftgig
  • Why you shouldn't be afraid to talk about your idea
  • What's the best way to reach out and cultivate potential mentors

A Few of Eddie's Favorite Books:

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Dan Wagner is the Founder and CEO of Civis Analytics, a startup that helps companies, non-profits, and campaigns leverage their data to develop smarter strategy, make better decisions, and build stronger, data-driven organizations. 

Before founding Civis Analytics, Dan Wagner was the Chief Analytics Officer on President Obama's 2012 campaign, overseeing a 54-person team of analysts, engineers and organizers that provided analytics and technologies for voter contact, digital, paid media, fundraising and communication. After a discussion with Eric Schmidt, Executive Chairman of Alphabet Inc., on election night, Dan decided to keep his team together and start a company. 

In This Episode You Will Learn:

  • How Civis Analytics started with great people and no set idea
  • How President Obama built an empowered meritocracy in his 2012 reelection campaign
  • The differences between building a company and a campaign
  • How Civis Analytics got their first customers
  • What you need to do excellent data science
  • Why the government is getting involved in fighting cancer 
  • The timeline for making progress on the cancer moonshot
  • Why they decided to build an innovative data science company in Chicago
  • Why Dan would like to see more risky financing in Chicago
  • The three things you need to ask yourself before starting a company

Selected Links From The Episode:

A Few of Dan's Favorite Books:

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Tracey Wiedmeyer is the CTO and a Co-Founder of InContext Solutions, the leader in scalable virtual reality (VR) shopping and retail solutions. InContext Solutions lets manufacturers and retailers simulate real in-store shopping situations to ideate, evaluate and activate all types of merchandising, display, layout and other in-store shopping experiences within a VR store environment before implementing them in the real world. Just last month, they closed their Series E round of funding, bringing their total funding to $42.5M. 

In This Episode You Will Learn:

  • Why Tracey and his co-founders started InContext Solutions
  • How he raised their seed capital from his family over Christmas
  • How similarly do people behave in virtual reality vs the real world
  • How InContext Solutions recreates stores
  • How they landed their first customers
  • How they try to lure tech talent away from quant trading
  • What he’d like to see big companies improve on
  • Why you have to focus on ROI and business cases when selling to large enterprises
  • Whether we are in a simulation or not
  • Where the future of virtual reality is heading in 5-10 years
  • What the future of retail may look like
  • How they landed a partnership with Intel
  • How a partnership with a big company can benefit a startup

Favorite Books:

Best Sources to Learn More About Virtual Reality:

Key points in this episode

Mark Lawrence is the CEO and Co-Founder of SpotHero, an on-demand parking app and website that makes drivers’ lives easier by helping them find and reserve a parking for up to 50% off. Mark along with his co-founders started the company after managing to rack up thousands of dollars in parking tickets. SpotHero is now one of Chicago's bigger consumer startup success stories. They raised $20 million in Series B funding last year, are in 15 cities, and have a team of 120 now. 

In This Episode You Will Learn:

  • Why he and his co-founders started SpotHero
  • How the product has evolved from the initial idea
  • How they got their first customers
  • What was going through his head when competitors were raising massive rounds
  • Keys to growing a marketplace business
  • How SpotHero approaches launching in a new city
  • Why "If it's not a fuck yes, it's a fuck no" when hiring
  • The benefits of meditation and floatation tanks
  • Keys to keeping the culture as company grows

Selected Links From The Episode:

Favorite Books:

Sponsored By:


  • Propllr: a Chicago public relations firm that helps startups and innovators build credibility and awareness for their companies, people, products and services.

Key points in this episode

Canh Tran is the CEO and Co-Founder of Rippleshot, a startup that detects payment card data breaches. They take a big-data machine learning approach, more common in search, genetics and advertising, and apply it in a novel way for the payment processing industry to help banks, merchants and processors proactively monitor suspicious fraudulent activity and implement smarter fraud risk management strategies when card compromises do occur. It is a massive industry with a lot of room for improvement. 

In This Episode You Will Learn:

  • How Rippleshot catches data breaches
  • Why banks need outside help
  • Where the name comes from
  • What they are looking for in breaches
  • The ingeneious ways credit cards are stolen
  • How safe is our future when we pay with wearables
  • How they got their first customers by starting small
  • Why criminals target smaller banks
  • The differences between Silicon Valley, Chicago, and St Louis
  • What Canh would like to see chicago tech improve on
  • The differences between 1871 and Catapult
  • The benefits of growing up abroad
  • The impact a handwritten thank you letter
  • What the future of fraud loss looks like
  • What gets Canh up in the morning

Selected Links From The Episode:

Favorite Book:

Key points in this episode

Raaja Nemani is a Co-Founder and CEO of Bucketfeet, a footwear startup that collaborates with a global community of artists to design limited-edition shoes.

The idea began in Argentina when Aaron Firestein gave Raaja a pair of hand-designed canvas sneakers inspired by the city blocks of Buenos Aires. On the rest of Raaja's journey, these unique looking shoes sparked non-stop conversations across six continents with people of all races, religions, genders, and cultures. Upon returning home, he decided to start Bucketfeet with Aaron. 

In This Episode You Will Learn:

  • The founding story
  • What the first shoes looked like
  • Where the name Bucketfeet comes from
  • How they sold their first shoes
  • How a party at Brian Splay's house jump started sales
  • Why Bucketfeet walked away from a Nordstrom deal
  • What is next for Bucketfeet

Selected Links From The Episode:

Favorite Book:

Key points in this episode

Shaily Baranwal is the CEO and Founder of Elevate K-12 and Classblox. Elevate K-12 provides digital instruction and online resources to  millions of at-risk students across the US. Since launching in 2008, Elevate K-12 has provided over 1 million hours of online instruction and has averaged a 35 percent increase in student test scores. Shaily's latest product, Classblox, is for consumers and it offers on-demand, online classes taught by real teachers. Students take hour long virtual, interactive classes from vetted teachers in subjects like algebra, Spanish, and ACT prep. 

Shaily and her company’s mission is to help ensure that every student gets one-on-one, online instructional support, irrespective of geography, demography and ethnicity. 

In This Episode You Will Learn:

  • How Shaily started Elevate K-12 while still in school
  • What makes Elevate K-12 better than MOOCs
  • How they are able to provide personalized teaching for a reasonable price
  • Why Shaily started her company in Chicago
  • Why she hasn’t moved the company
  • Why she’s a big fan of distributed teams
  • How she was able to bootstrap for so many years
  • Why she decided to finally raise money
  • How she made her first sales
  • What she wished she knew when she got started
  • Why attitude and passion are everything when hiring
  • Why she likes to hire athletes

Selected Links From The Episode:

Favorite Books:

Sponsored By:


  • Propllr: a Chicago public relations firm that helps startups and innovators build credibility and awareness for their companies, people, products and services.

Key points in this episode

Kayne Grau is a Co-Founder and CEO of DRIVIN, a startup changing the way used-car dealers source their used-car inventory. Before founding DRIVIN, Kayne was the CTO at Cars.com.

Using proprietary technology and actionable local market data, DRIVIN sells, sources, acquires and delivers used-car inventory for used-car dealer partners across the country. DRIVIN helps dealers understand what’s selling locally and how to price effectively. DRIVIN has raised $17.5 million from investors including Brad Keywell, Eric Lefkofsky, Mitch Golub, and Columbus Nova Technology Partners.

In This Episode You Will Learn:

  • How inefficient the used car market is
  • The origins of DRIVIN
  • How Lightbank companies are started up
  • How involved Eric Lefkofsky and Brad Keywell are after coming up with an idea
  • What makes Eric and Brad's new startups repeatedly successful
  • Why DRIVIN went the B2B instead of B2C route
  • How they got their first customer
  • The best way to buy/sell used car as an individual
  • What can Chicago tech improve on? 
  • Impact of self driving cars on used car business

Selected Links From The Episode:

Favorite Books:

Key points in this episode

Constance Freedman is the Founder and Managing Partner of Moderne Venturesan early stage venture fund and accelerator investing in technology companies in real estate, mortgage, finance, insurance, and home services. These are multi-trillion dollar industries that make up well over 20% of the US GDP and are ripe for innovation.  Prior to launching Moderne Ventures, Constance was the head of Strategic Investments at the National Association of Realtors where she launched and managed its investment arm, Second Century Ventures (SCV), and founded its accelerator program, Reach. 

In 2014, Constance was recognized by Crain’s Business in its prestigious 40 under 40 award and was also named on Crain’s Chicago Top Tech 50.  In both 2014 and 2015, Constance was recognized on Swanepoel’s Power 200 Most Powerful Individuals in Residential Real Estate and in 2015, named in Inman’s Top 101 in Real Estate.

In This Episode You Will Learn:

  • The most exciting tech developments for Moderne Ventures
  • Why venture capital firms start accelerators
  • How important an accelerator is for the deal flow
  • What the decision making process looks like for the accelerator and investments
  • Where they find the best companies for their accelerator
  • How to break into venture capital
  • How to find the right limited partners (LPs)

Selected Links From The Episode:

Key points in this episode

Nick Moran is a co-founder and Managing Director of New Stack Ventures and Moran Capital Partners. He also started the very popular The Full Ratchet podcast, where he interviews venture capital and angel investing experts on successful startup fundraising and investing strategy. Nick asked me to interview him for his 100th episode and I thought the content was so good that I decided to repost it here. 

In This Episode You Will Learn:

  • How Nick got into venture capital
  • Why he started The Full Ratchet
  • His key takeaways after 100 episodes
  • Where he finds his deals
  • What an ideal startup looks like to him
  • What resources he recommends to investors and entrepreneurs
  • Nick's investment thesis and how he evaluates startups for investment
  • The best and worst things about the startup ecosystem in Chicago

Selected Links From The Episode:

Favorite Books: 

Key points in this episode

Philip Tadros is a true serial entrepreneur and restauranteur. He is the founder of Doejo, a digital agency, Dollop Coffee, a cafe and bakery, Bow Truss Coffee, a coffee roastery and cafe, The Budlong, a hot chicken restaurant chain, SPACE, a co-working space, and Aquanaut Brewing, a craft brewery. He opened his first coffee shop at 19 after dropping out of college and now runs the largest network of independently owned coffee shops in Chicago. 

Crain's recently ran a special report questioning some of Phil's business practices titled "One of Chicago's most connected entrepreneurs has made more than a few enemies". We dive into what really happened in the second half of this episode and what he's learned from the experience.

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In This Episode You Will Learn:

  • How Phil got his start as an entrepreneur after dropping out of college
  • The differences between the beer and coffee community
  • How he differentiates himself in the competitive food industry 
  • Phil's side of the story on the Crain's special report
  • What he’s learned from the experience
  • How he and his team handled the bad press

Selected Links From The Episode:

Favorite Books: 

Key points in this episode

Dima Elissa is the founder and CEO of VisMed3D, a startup providing 3D surgical patient replicas for state-of-the-art treatment and training of doctors. Based in Matter, the startup is on the cutting edge of personalized medicine. In addition to her startup, Dima devotes considerable time, energy, and guidance to other women entrepreneurs. 

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In This Episode You Will Learn:

  • How Dima decided to pursue 3D printing 
  • How Dima landed her first partnership with big healthcare
  • What the best bang for you buck networking is
  • The value in 3D printing for surgeons
  • What the future of medical 3D printing looks like
  • The value in snapchat for her company
  • What to watch out for as a first time founder

Selected Links From The Episode:

Favorite Books: 

Key points in this episode

Star Cunningham is the Founder and CEO of 4DHealthware, a startup that provides artificially intelligent "nudges", SMS and email messages, to patients with chronic conditions based on data collected via 250 wearable devices like bluetooth glucometers and activity trackers. Medicare now reimburses healthcare providers $40 per patient per month for every 20 minutes spent managing care outside a doctor’s office and 4DHealthware interactions count. Star has raised $770,000 to date and is on the verge of becoming the 12th African American woman ever to secure more than a million dollars in venture funding for her tech startup. Before founding, 4DHealthware, Star was at IBM for about 10 years. 

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In This Episode You Will Learn:

  • Why Star decided to found a company after working in big business
  • How she landed the first partnerships in healthcare
  • The power of nudging people in the right direction
  • The future of wearables and artificial intelligence
  • How to get more diversity in tech
  • The importance of getting young black girls into tech
  • What she thinks about diversity quotas
  • When founders should start thinking about diversity

Selected Links From The Episode:

Favorite Book: 

Key points in this episode

John Roa is a serial tech entrepreneur and long time Chicagoan. He got his entrepreneurial start by creating a computer repair business at 14 and hasn't stopped since. Last year, he sold ÄKTA, his tech-consulting and design firm, to Salesforce.  Now John is planning to invest in other Chicago startups via Roa Ventures, a fund that focuses on "early-stage investments, projects and experiments". He has also created the non-profit, Digital Hope, and enjoys playing competitive poker and traveling extensively. 

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In This Episode You Will Learn:

  • How John got started as an entrepreneur
  • Why he started AKTA and where the name comes from
  • What John attributes the success of AKTA to
  • How John made the the decision to sell AKTA? 
  • If he would take venture capital if he could do it again
  • Problems he sees in taking venture capital
  • Why he's investing instead of starting another startup
  • John's criteria for his next startup
  • What draws John to travel? He has been to 50+ countries. 
  • How to build a brand as a new angel investor?
  • Similarities between poker and startups
  • What Chicago tech is good at & what we could improve on
  • Why John doesn’t believe in giving advice

Selected Links From The Episode:

Favorite Book: 

Key points in this episode

Stu Grubbs is a Co-Founder and CEO of Infiniscene, a startup building the easiest way to livestream video. They enable gamers, and now Facebook and Youtube streamers, to easily create beautiful live broadcasts in their web browser without any experience or expensive hardware. As Stu mentions during the show, a lot of Chicago startups are new tech solving old problems so it is awesome to to have a startup empowering live streamers being built here. It is definitely both a cutting edge problem and solution. 

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In This Episode You Will Learn:

  • How difficult it is to setup a lifestream today
  • Why quality will always be the differentiator with content creators
  • How big e-sports is today? Hint: a lot bigger than you think
  • How e-gamers make more money on content then competition
  • What Infiniscene got out of Techstars
  • Why starting a company is the real way to see if you are good at something
  • How a landlords faith in him allowed Infiniscene to survive
  • What kept him going when he was penniless
  • How he ended up hiring his biggest critic
  • Whats the most exciting stuff he saw at E3
  • How live streaming may work in virtual reality
  • How they have developed culture early in the company
  • The importance of one-on-one's for culture
  • Why they founded Infiniscene in Chicago
  • Why every call should be a video call on a distributed team
  • Why he looks for cultural fit first when hiring

Selected Links From The Episode:

Favorite Books: 

Key points in this episode

David Rabie is the Founder and CEO of Tovala, the creator of a smart oven that cooks perfectly made meals by baking, boiling and steaming them in under 30 minutes. The meals can either be delivered prepackaged from Tovala or be made using a crowdsourced recipe. Last winter, Tovala graduated from Y-Combinator and a few months ago Tovala launched a successful Kickstarter campaign that raised $255,603 with over 1,000 backers. Before starting Tovala, David was an MBA at Chicago Booth, and he worked for the co-founder and CEO of Veggie Grill and ran Groovy Spoon – a bi-coastal chain of frozen yogurt stores. He also spent time working at Google and Foundation Capital. 

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In This Episode You Will Learn:

  • Why he decided to pair food delivery with a smart oven
  • How they came up with the name Tovala
  • How David found his first engineer
  • How they decided on the price of the oven and the food
  • How they prepared for their successful Kickstarter campaign
  • What they got out of Y-Combinator? 
  • Why they decided to come back to Chicago after Y-Combinator?
  • Why he wishes he had found a co-founder earlier
  • How to test for cultural fit and avoid mishires
  • The importance of establishing connections with VCs before you need money

Selected Links From The Episode:

Favorite Books: 

Key points in this episode

Landon Shoop, along with his wife Jennifer Shoop, started Fizz, a team management tool that makes developing employees easy. At his old job, Landon became frustrated while preparing for another yearly performance review and he decided there must be something better. Together they developed a HR tech platform that allows for real-time employee/employer feedback. Landon and Jennifer haven't raised any outside money yet, but they already have some impressive traction. It was great to talk product with promising entrepreneurs just getting started. 

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In This Episode You Will Learn:

  • How to decide whether your idea is worth pursuing
  • How to sell your product
  • Why they decided to build upon Slack
  • How they came up with the name? Hint: Focus is your scarcest resource
  • How they approach work/life balance as a husband/wife founding team

Selected Links From The Episode:

Favorite Books: 

Key points in this episode

Michael Slaby is the Founder and Head of Mission of Timshel, a startup that has developed a platform called The Groundwork to give organizations and brands more powerful digital tools to analyze all the data they are producing, help them organize supporters, get their message out, and raise money. According to Federal Election Commission records, Hillary Clinton has spent almost $500,000 on Timshel’s services since announcing her candidacy last year. Before starting Timshel, Michael was the CTO of Obama for America in 2008 and Obama’s Chief Integration Officer in 2012,  overseeing the campaign's integration of technology, digital strategy, and analytics. 

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In This Episode You Will Learn:

  • How an "argument of violent agreement" got Michael into politics
  • The differences between the 2008 election and 2012 election
  • What the team took from the 2012 campaign to Timshel
  • How Timshel balances being a for profit company and having a social mission
  • How Timshel is helping Hillary Clinton's campaign
  • Why they started a podcast
  • Why we need to improve the availability of early stage capital here in Chicago (None of Timshel's investors are from here)
  • Why Michael thinks Chicago has a bright future in impact analytics
  • How entrepreneurs can balance the line between optimism and insanity

Selected Links From The Episode:

Favorite Books: 


  • East of Eden by John Steinbeck (where the name Timshel comes from)

  • This Is Water by David Foster Wallace (given to every new employee) 

  • Shantaram by Gregory David Roberts

Key points in this episode

Jason Kunesh is a co-founder and CEO of Public Good Software, a startup aiming to make donating to non-profits as easy as ordering something on Amazon. Before starting PGS, Jason was the Director of UX for Obama's 2012 reelection campaign and part of the founding team at The Point, which later became Groupon. Jason is also a member of the adjunct faculty at the Starter School, owner of the best Fu Manchu in Chicago, a mentor at Impact Engine, and an advisor to the American Design and Master-Craft Initiative and UX for Good.

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In This Episode You Will Learn:

  • How he got involved in the Obama campaign?
  • What it is like demoing your product for the president?
  • What the team learned on the Obama campaign and then applied at Public Good?
  • Why charities for animals outperform charities for the homeless?
  • Why non-profits are scared of innovation?
  • How he got into tech? 
  • Why you should be public about your failures?
  • Why Chicago is the best place to start a non-profit focused company?
  • What we need to to do to take Chicago tech to the next level?
  • How startups are like bands?
  • How to get a team to work together? Hint: Encourage transparency/dialogue/dissent
  • Why you really have to understand your motivations as a founder?

Selected Links From The Episode:

Favorite Books: 

 

Key points in this episode

Gale Bowman is the founding director of Irish Angels, an angel network dedicated to early stage investments in which a founder, board member, or active investor is a student, graduate, parent, or faculty member of the University of Notre Dame. After graduating from business school in 2012, Gale launched Irish Angels and has since grown the angel network to 150 investors and invested $10 million in seed and Series A investments. 

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In This Episode You Will Learn:

  • Where Irish Angels sources their best deals?
  • What is the biggest mistake that first time founders make? 
  • What is the future of university-affiliated angel networks/vc funds?
  • What are the benefits of an angel network over a venture capital fund?
  • What an ideal founding team looks like? 
  • What abilities an ideal CEO has? Hint: Sales and Metrics
  • What a typical week looks like for VC/angel network director? 
  • How to land your first job at a startup? 
  • How build relationships in the startup community?

Favorite Book: How to Win Friends & Influence People by Dale Carnegie

Selected Links From The Episode:

Key points in this episode

Craig Vodnik is a co-founder of Cleverbridge, a global subscription billing provider. Founded in 2005, Cleverbridge has grown to 300+ employees with offices in Cologne (Germany), Chicago, San Francisco and Tokyo. They have done this all without raising any outside money. At the beginning of his career in 1995, Craig served as the Webmaster of the Chicago Tribune, where he launched its first website. Outside of Cleverbridge, Craig helps develop other entrepreneurs as a mentor at 1871, Catapult Chicago, Junto Institute, University of Illinois at Urbana-Champaign Enterpriseworks Entrepreneur-In-Residence and as a board member of Hyde Park Angels.

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In This Episode You Will Learn:

  • How they maintain their company culture with offices in different countries? 
  • Why you should bootstrap for as long as you can?
  • When is the right time to take venture capital?
  • Why we need more risk taking in Chicago?
  • What fantasy football can teach you about business?
  • How to go about finding and cultivating mentors?
  • Why he decided to join Hyde Park Angels and become an angel investor?

Favorite Books:

Selected Links From The Episode:

Key points in this episode

Jacob Babcock is the founder and CEO of NuCurrent, a wireless power company that has designed the world's fastest, smallest, and most efficient wireless power antennas. If you have ever wondered why we still have to deal with all these charging cables, this is the podcast for you.

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In This Episode You Will Learn:

  • How Jacob made the transition from law school to founder of a very technical startup?
  • What a future with wireless power will look like? 
  • How NuCurrent is stealing business away from multi-billion dollar competitors? 
  • Chicago's storied history as the birthplace of wireless power
  • How to test if someone will make for a good startup employee? 
  • The one big thing he wishes he knew when he started NuCurrent

Favorite Books:

Key points in this episode

Jeff Carter is a co-founder of Hyde Park Angels, one of the most active angel groups in the United States, and he is currently raising a VC fund, named West Loop Ventures. Before becoming an angel he was a trader for over 25 years and he continues to trade independently. 

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In This Episode You Will Learn:

  • How Hyde Park Angels started?
  • Why traders make for good angel investors?
  • Why having pornographers and money launderers latching on to your product early is a great sign? 
  • Why it has been easier to find LPs for West Loop Ventures outside of Chicago? 
  • Why you have to be a great analyzer of people and not just ideas for seed investing?
  • Why it's important to have a vision for the future as a seed investor?
  • Why VCs can bet on ideas, but angels have to be on people?
  • Why being coachable is so important for entrepreneurs?
  • How an entrepreneur/investor relationship is like dating? 
  • Why he makes a point of blogging everyday?
  • What we have to do to keep growing the Chicago tech scene? 

Favorite Blogs:

Favorite Books:

Selected Links From The Episode:

Key points in this episode

Katlin Smith is the founder of Simple Mills, a food startup that only uses simple, whole food ingredients. While working as a consultant, Katlin discovered she had a gluten-sensitivity and started experimenting with her almond-flour baking mixes on the weekends.  Shortly after launching her almond flour muffin mix, it became the best selling muffin mix on Amazon. Simple Mills is now in over 2,000 stores nationwide, including in Whole Foods and Mariono's in Chicago. 

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In This Episode You Will Learn:

  • How she came up with the idea for Simple Mills?
  • Why it's important to be the "chief sales officer" as the founder of a startup?
  • Why she started with baking mixes?
  • Why nuts are so expensive?
  • What she loves about being an entrepreneur?
  • What the process is like to bring a new food product to market? 
  • How she has found and cultivated her advisors? 
  • How the challenges of being a founder change as your startup grows?
  • How she approaches getting into new stores?
  • Why she thinks Chicago is the easiest city to network in? 

Favorite Books:

Miscellaneous Things Mentioned:

Key points in this episode

Ezra Galston is a VC at Chicago Ventures. At CV, Ezra focuses on consumer facing investment and is actively involved with BloomNation, Kapow Events, Luxury Garage Sale, Shiftgig, SpotHero, Zipments, and Havenly. He writes one of my favorite VC blogs at BreakingVC.com and his thoughts on startups have also been published in the Wall Street Journal, TechCrunch, VentureBeat, and Re/code. Before becoming a venture capitalist, Ezra was a professional poker player and the Director of Marketing for CardRunners Gaming. 

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In This Episode You Will Learn:

  • How Ezra got into angel investing? 
  • What motivates Chicago Ventures?
  • What's the one question every founder should ask of their VCs?
  • Why Ezra prefers growing a business over starting one?
  • Where Ezra sources his investments from?
  • Why producing content as a VC is important? 
  • How they look for outliers in the entrepreneurs they back?
  • How Ezra finds and cultivates his mentors? Hint: cold emailing 
  • Why Ezra thinks e-commerce companies are underestimated?
  • What Ezra wishes he knew when he first got into the venture industry?
  • Why some venture capital investments never get announced?
  • Why Ezra thinks Chicago is so good at building great business? 
  • What we can do to make Chicago even better for startups? 

Favorite Books:

E-Commerce Companies:

Investors Ezra Admires:

Miscellaneous Things Mentioned: 

Key points in this episode

Neal Rothschild is the founder of Rooster, a 6-minute daily podcast that updates you on all the news you need to know. Neal just launched Rooster at the beginning of this year and it was great to interview a founder just getting started on a really promising startup. Neal initially came up with the idea while walking back and forth to the school he was teaching at in Romania. Before Rooster, Neal was also a journalist with pieces published in the New York Times and USA Today. 

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In this episode we cover:

  • Why he decided audio is the most effective and efficient way to get information?
  • How he landed on the name Rooster?
  • Why critical feedback is the best feedback? 
  • What the process is like producing a daily podcast?
  • How he stays on top of all the news in the world? Hint: Twitter lists

Neal’s Idols in New Media: 

Neal’s Favorite Books: 

Key points in this episode

Aaron Dallek is a serial entrepreneur and Co-Founder of Opternative - the world’s first online eye exam. The exam can be taken from anywhere, at anytime, and a doctor issued prescription can be used to shop everywhere. The exam only takes 25 minutes and a digital prescription is delivered in 24 hours or less.
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In this episode we cover:

    -How to raise money in the current down market - In February 2016, Opternative closed their Series A ($6 million) from Jump Capital, Chicago Ventures, Pritzker Group, Tribeca Venture Partners, Corazon Capital, and NextGen Partners.
     -How they built an online eye exam that rivals the traditional phoropter
     -How to recruit the best talent against larger companies with deeper pockets
     -Why you have to take things one step at a time as an entrepreneur

Aaron’s Favorite Book: The Art of the Start 2.0: The Time-Tested, Battle-Hardened Guide for Anyone Starting Anything by Guy Kawasaki

Key points in this episode

Ryan Coon is the founder of Rentalutions and a former investment banker. Rentalutions provides all-in-one landlord management software. Whether you manage one unit or multiple buildings, Rentalutions gives you the ability to receive electronic rent payments, manage leases, find the right tenants, and deal with maintenance issues.
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In this episode we cover:

    Making the transition from investment banking to entrepreneurship
    Starting a company for the right reasons
    How the Chicago tech scene has changed
    Finding your first customers

Ryan’s Favorite Book: The Monk and the Riddle: The Art of Creating a Life While Making a Living by Randy Komisar

Key points in this episode

Rod Rakic is the founder of OpenAirplane, a plane sharing marketplace. OpenAirplane makes it easy for pilots to find, book, and pay for aircraft rentals online or on their phones. Renting an airplane is now as easy as renting a car.
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In this episode we cover:

    The benefits of private aviation over commercial travel
    The secret to avoiding parking fees at airports
    Why you ask for advice instead of money
    Making things work as a distributed team

Rod’s Favorite Book: The Customer Support Handbook: How to Create the Ultimate Customer Experience for Your Brand by Sarah Hatter

Key points in this episode

David Gardner is the founder and CEO of ColorJar, a Chicago-based creative tech agency. Before founding ColorJar, David was a professional basketball player and a founder of a social network in India. ColorJar specializes in branding and creating custom websites and mobile apps and has worked with everyone from Fortune500 corporations, to venture-funded startups.
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In this episode we cover:

    Why he decided to start an agency
    What makes a great name and brand
    How to approach building a new brand to cut through all the noise
    Why user personas are better than talking about demographics
    How the Chicago tech scene has changed in his 8 years since founding ColorJar
    The surprising benefits of having a distributed team
    Why employees and employers should date (contracting) before marrying (full time)
    Why he prefers to hire freelancers
    Why you should follow your instincts

David’s Favorite Book: Blink: The Power of Thinking Without Thinking by Malcom Gladwell

Key points in this episode


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