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: 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 …

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 busine…

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. Dave is taking a different approach with Purchasing Platform and t…

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 raise…

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 S…

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, co…

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 ha…

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 Draft…

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, manag…

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 educa…

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 …

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 vend…

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 …

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 Wil…

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 …

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 Lea…

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 m…

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, sel…

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 wher…

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 Thi…

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…

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 lik…

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. Ear…

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…

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 be…

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.…

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, overse…

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 exper…

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 consum…

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 activ…

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 loo…

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 late…

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 count…

Constance Freedman is the Founder and Managing Partner of Moderne Ventures, an 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…

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…

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 droppi…

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. listen o…

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 e…

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-…

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 s…

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 s…

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/emplo…

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, H…

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 f…

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 ne…

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 C…

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. listen on iTunes listen on stitcher In This Episode You Will Learn: …

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. listen on itunes listen on stitcher In This Episode You Will Learn: How Hyde P…

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 …