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 many of Chicago’s hottest startups. Check out what they’re up to at StartingLine.vc.

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:

• 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.

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:

• 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.

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 they just raised their Series A.

Topics Covered:

• Selling a bootstrapped business for $22M

• Deciding to join an established business vs starting a new one

• Issues with joining an established business as a CEO

• Changing a startup’s culture

• The revolution of mobile home communities and manufactured housing.

• Building a niche marketplace

• Losing & winning back their biggest customer

• Focusing on internal communication as much as external

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.

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:

• 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.

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:

• 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.

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:

• 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.

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:

• 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.

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:

• 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.

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.

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.

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:

• Sandman Series by Neil Gaiman
• Getting Things Done: The Art of Stress-Free Productivity by David Allen

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:

• Snow Crash by Neal Stephenson
• The Codebreakers: The Comprehensive History of Secret Communication from Ancient Times to the Internet by David Kahn

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:

• Sapiens: A Brief History of Humankind by Yuval Noah Harari
• The Count of Monte Cristo by Alexandre Dumas père
• Behave: The Biology of Humans at Our Best and Worst y Robert M. Sapolsky

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:

• New Venture Challenge
• Craig Wortmann, Professor at Northwestern Kellogg
• Eater

Favorite Books:

• Shoe Dog: A Memoir by the Creator of Nike by Phil Knight
• Setting the Table: The Transforming Power of Hospitality in Business by Danny Meyer
• Steve Jobs by Walter Isaacson

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:

• Zeke Markshausen, Designer at IDEO

Favorite Books:

• Internal Time: Chronotypes, Social Jet Lag, and Why You're So Tired by Till Roenneberg
• The Promise of Sleep: A Pioneer in Sleep Medicine Explores the Vital Connection Between Health, Happiness, and a Good Night's Sleep by William C. Dement
• Decisive: How to Make Better Choices in Life and Work by Chip Heath and Dan Heath
• The Sales Acceleration Formula: Using Data, Technology, and Inbound Selling to go from $0 to $100 Million by Mark Roberge

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:

• Richard Feynman, theoretical physicist
• Principles by Ray Dalio
• Nash equilibrium
• Al Goldstein, Founder and CEO of Avant

Books Mentioned:

• A New Kind of Science by Stephen Wolfram 
• The Economics of Life: From Baseball to Affirmative Action to Immigration, How Real-World Issues Affect Our Everyday Life by Gary Becker
• Thinking, Fast and Slow by Daniel Kahneman
• Antifragile: Things That Gain from Disorder by Nassim Nicholas Taleb

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:

• Steve Jobs by Walter Isaacson
• 41: A Portrait of My Father by George W. Bush

Sponsored By:

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

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:

• Fredrik Olsen, CTO at Bright
• Brian Flanagan, CPO at Bright
• Troy Henikoff, Techstars Chicago Managing Director
• Brian Luerssen, Techstars Chicago Managing Director
• Dan Willoughby, Techstars Chicago Program Manager 
• SaaStr Annual Conference
• Bright Conference

Favorite Books:

• The Hard Thing About Hard Things: Building a Business When There Are No Easy Answers by Ben Horowitz
• Managing Oneself by Peter Ferdinand Drucker
• Checklist Manifesto by Atul Gawande

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:

• Maxwell Ryan, Founder of Apartment Therapy
• The Everygirl
• Monica + Andy
• Trunk Club

Favorite Books:

• Sapiens: A Brief History of Humankind by Yuval Noah Harari
• Harry Potter by J.K. Rowling

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