Tech In Chicago

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

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:

• Red Antler, branding agency behind Casper and All Birds
• Carter Cast, Professor at Northwestern Kellogg and Venture Partner at Pritzker Group Venture Capital
• Troy Henikoff, Managing Director at MATH Venture Partners
• Brian Luerssen, Former Techstars Chicago Managing Director
• Dan Willoughby, Techstars Chicago Director
• Amanda Lannert, CEO of Jellyvision

Favorite Books:

• Wuthering Heights by Emily Brontë
• The Sun Also Rises by Ernest Hemingway
• All The Light We Cannot See by Anthony Doerr
• The Devil in the White City: Murder, Magic, and Madness at the Fair That Changed America by Erik Larson
• Born to Run: A Hidden Tribe, Superathletes, and the Greatest Race the World Has Never Seen by Christopher McDougall

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

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:

• WiSTEM

Favorite Books:

• Born to Run by Bruce Springsteen
• Bossypants by Tina Fey
• Tune In: The Beatles: All These Years by Mark Lewisohn
• Elon Musk: Tesla, SpaceX, and the Quest for a Fantastic Future by Ashlee Vance
• Shoe Dog: A Memoir by the Creator of Nike by Phil Knight

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

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:

• Michael Krasny, Founder of CDW
• Alex White, Founder of Next Big Sound
• David Cohen, Founder of Techstars
• Sam Yagan, CEO of Shop Runner
• Brad Feld, VC at Foundry Group
• Sphero
• Fitbot
• Casey Jenks, Founder of Fitbot

Favorite Books:

• The Fountainhead by Ayn Rand
• Made to Stick: Why Some Ideas Survive and Others Die by Chip Heath
• Venture Deals: Be Smarter Than Your Lawyer and Venture Capitalist by Brad Feld

Sponsored By:

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