Sparking Conversations One Shoe at a Time - Raaja Nemani / Co-Founder of Bucketfeet

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:

What Does the Future of Education Look Like? - Shaily Baranwal / Founder of Elevate K-12 & Classblox

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.

Disrupting the Used Car Market With Data - Kayne Grau / Founder of DRIVIN

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:

Why Join A Tech Accelerator & Why VCs Start Accelerators - Constance Freedman / VC @ Moderne Ventures

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 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:

Sponsored By:

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

What An Ideal Startup Looks Like & Deal Sourcing With A Podcast - Nick Moran / The Full Ratchet

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: 

 

 

    How To Deal With Bad Press & Competing In The Crowded Coffee Market - Philip Tadros / Founder Doejo & Bow Truss

    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.

    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: 

    Personalized Medicine, 3D Printing, Snapchat & Networking - Dima Elissa / Founder of VisMed3D

    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. 

    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: 

    Artificial Intelligence, Healthcare Startups, Wearables & Diversity - Star Cunningham / Founder of 4DHealthware

    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. 

    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: 

    Investing In Design-Led Companies & What Chicago Tech Is Missing - John Roa / AKTA & Roa Ventures

    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. 

    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: 

    Livestreaming, Virtual Reality, E-Sports & Hiring Your Biggest Critic - Stu Grubbs / Founder of Infiniscene

    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. 

    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: 

    The Future Of Food Tech & How To Raise $100k In Your First Day On Kickstarter - David Rabie / Founder of Tovala

    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. 

    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: 

    How To Decide If Your Idea Is Worth Pursuing & How To Sell Your Product - Landon Shoop / Co-Founder of Fizz

    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. 

    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: