Growing up in Chicago's south side and now growing a business in Chicago's tech hub, Chris Motley has come full circle. But when you dig a little deeper, it becomes clear that Motley was constantly carving out his own unique path towards becoming a CE0 and founder of a rapidly growing startup providing solutions to the job search process.

Upon graduating from Columbia, Chris began his career as a trader at Goldman Sachs.   After a few years, he switched gears and joined 1888 Mills, a global home and commercial textile manufacturer.  While at 1888 Mills, Chris served as Director of Global Strategy Sustainability and later became Executive Vice President, all while picking up an MBA from Northwestern’s Kellogg School of Management.

Frustrated with the inefficiencies he saw plaguing the job search process, Chris pitched an idea to solve the issue at Chicago’s 2011 Startup Weekend.  The idea captivated fellow attendee Kunal Parbadia, and a few months later the two co-founded Better Weekdays.

Touting itself as the GPS for Your Career Journey, Better Weekdays helps students and professionals navigate the tricky and frustrating job search process by matching their values with career opportunities.  JobScript, an online self-assessment and development tool created by the team at Better Weekdays helps you recognize your unique strengths and provides clarity and targeted professional development to the job search process.

Job seekers utilize comprehensive and validated feedback provided by JobScript, enabling them to develop a plan for their professional life.  Better Weekday users then go on a private job-matching platform providing opportunities aligned with their preferences and job compatibility.

Targeting students and alumni from top universities, Better Weekday’s currently offers it’s assessment for free to students from schools such as Northwestern, Michigan, and Notre Dame.  You can watch Chris discuss Better Weekdays during a recent Technori Pitch event here. To learn more about Chris and Better Weekdays, check out my interview with him below and check out their website betterweekdays.com

Q: What is wrong with the current model behind staffing and recruiting? In a word - everything! Specifically, resumes don’t adequately capture an individual or determine success.  Also, there is little objectivity in the current process. 

There are three big insights that validate what we are doing: 1) By the time one is 30, they will have had 4 different jobs - and there needs to be a platform to facilitate these inevitable transitions, 2) universities are not necessarily funded to provide career services to alumni, thereby fueling the current staffing/recruiting model and 3) companies that  traditionally recruit college graduates don't have access and visibility to certain campuses/alumni pools to objectively select quality talent in a cost effective way. Better Weekdays seeks to be the GPS for one's career journey - a private platform to help individuals actively manage their careers.  This enables us to provide our corporate customers with "best fit" candidates at half the cost of traditional sources. 

Q: What made you decide that culture fit is the most important determinant of success for a “better weekday”?
 We didn't decide culture fit is important - the market did - and as a result, it is a key component of our job matching process.  In established organizations, people tend to outgrow their jobs (in startups, it is the opposite).  Specifically, the rate at which employees acquire skills is much faster than the time it takes for their roles to change - leading to unhappiness and attrition.  If someone is a good fit - defined by their motivations, abilities and personality being aligned to their job and work environment - they will be happier and tend to stay longer.  With the cost of replacing an employee at 1.5x the salary, its easy to recognize the value an extra year can contribute to the bottom line.     

Q: Why the decision to initially focus on recent grads/alumni from top 50 universities?  
We no longer limit ourselves to top universities.  Originally, it was a function of focus and recognizing that the path to get more universities on board is least resistant when you have top universities on board.  Also, we wanted to leverage the admission standards of selective schools to entice companies to be interested in our value proposition.

Q: What makes JobScript better than your average Meyers Briggs Test that most students take to find out what occupation would fit their personality?
JobScript is a career assessment that takes the most holistic perspective of an individual in the context of finding meaningful work.  Other tools, including MBTI, were not specifically designed for this purpose.  It is also important to note that JobScript is only part of the "career DNA" that we capture from an individual.  We also capture their preferences and work experience, which, provides a very holistic picture of a candidate before the 1st interview.

Q: Since your company is focused on recruiting and hiring, what matters most to you as a founder and CEO when it comes to finding new employees?                                                              It is crucial that someone has the motivations, abilities, and personality for the job that they have to do at Better Weekdays.  We eat our own dog food - every current/potential employee goes through JobScript as part of the screening process.  

Q: If you could only ask a potential hire one or two questions, what would they be?                 1) What have you built and why (if they have not built anything - why did you make the choices you made thus far in your career journey)? and 2) Can you explain something to me that you know VERY well (ideally it should be related to the job they applied for)? 

 Q: Better Weekdays puts a good amount of focus on the idea of personality types and characteristic, what is the most important characteristic when it comes to being an entrepreneur?
 A key framework that underlies our technology is Career Archetypes.  There are 9. For example, Artistic Creativity, Human Development, and Process Efficiency.  These archetypes are the manifested by the combination of one's Motivations, Abilities and Personality (MAP) and we measure the dominant archetypes in every individual.  For an entrepreneur, my view is that Entrepreneurial Challenge, Motivational Energy and Strategic Decisions matter most.  I hope that I'm right, because those are my 3 dominant archetypes!  

Planning a social event with friends in the city can be an exhausting, frustrating, and expensive process.  For Chicago residents, CitySwarm is looking to take the hassle out of social events and allow young, outgoing people to explore their city in an easier and more social way.  Launched back in February of 2011, CitySwarm has been riding the wave of group-buying startups and has found their niche serving Chicago’s young professionals seeking easy and effective ways to add some variety to their social experience.
 
After you quickly sign up and create a profile, CitySwarm sends you their weekly newsletter detailing their upcoming events.  Whether it’s a Cubs game, a craft beer tour, or a sailing trip, CitySwarm has a wide variety of events that provide hassle-free entertainment to young Chicagoans looking to explore the city and meet new people.  I caught up with CitySwarm’s founder Lindsay Saewitz to discuss her entrepreneurial journey as well as the ins and outs of running a company like CitySwarm.  

Q: How does CitySwarm get the word out about events?
We use a variety of ways to get the word out. Our weekly email is the primary way we get our events out there, and then we supplement that with social media and posting it on a variety of event sites.

Q: What has been the response from the venues hosting CitySwarm events?
Overall very positive. We feel like we're delivering valuable marketing exposure at low-to-no cost, and our partner venues have echoed this sentiment. 

Q: What unique features about Chicago make it the perfect place for an idea like CitySwarm?
The sheer size of the young professional demographic make it a great place, but of course beyond that is all of the amazing things there are to do. With the change in seasons there's always something festive going on, and a new bar or restaurant opens every week.

Q: Do you envision expanding CitySwarm to other major cities going forward?
To be determined:) In my mind I can see a CitySwarm in every city, but getting to that point would certainly be a challenge.

Q: Did you ever plan on becoming an entrepreneur?
Nope...I always envisioned myself at a large corporation, which is where I began right out of college. There's things I really like about that environment, and I may end up there again one day, but I really wanted to take a gamble and start my own business. I felt that it was the right time, and that if I didn't do it when I did I would have regretted it.

Q: What ways in particular did your marketing and online sales background help you grow your business?
It was everything. When I graduated college, the last place I thought I would be at was in an entry level sales position making 125 cold calls a day. But it taught me how to do business and how to sell - essential to anyone starting a business. My marketing skills helped me create a brand and grow the list, and communicate the value to businesses. 

Q: What has been the biggest challenge of running your own company?
For me personally, it's been being alone without much help or support from colleagues or a mentor. I've said in other interviews how I like working alone, which I do, but what I do miss is the camaraderie and emotional support of a team. I've been lucky to find some awesome people in the startup community who keep me sane, though! 

Q: What are some upcoming CitySwarm events you are excited about?
I love our fall events, specifically Sunday Funday on the Farm. Everyone gets decked out in boots, cowboy hats, and plaid - and it's just so fun spending the day outside the city. In general November and December are pretty festive, so I like that our events like the Thanksgiving Cooking Class and Holiday Trolley help celebrate the season.

Your photos are worth more than you think.  It’s a simple idea, but it’s one that means a lot to people like Corbett Drummey.  Knowing he wanted to turn this idea into something more tangible, Corbett and his co-founders got together a few months ago and decided to launch Popular Pays, a platform that allows Chicago businesses to connect with local Instagram influencers to form a mutually beneficial bartering relationship.

The team at Popular Pays is not the first to tackle the concept of social media currency, but the beautifully designed app integrates seamlessly with Instagram and has struck a chord with customers and vendors throughout Chicago.  Now your artsy pic and clever filters can get you a cup of coffee or a slice of pie in a simple and mutually beneficial exchange. 

While the service only works with businesses in Chicago for now, Popular Pays is looking to expand by engaging with its followers on Twitter to decide where to bring the app next.  Their answer so far?  Istanbul, Turkey.  I got a chance to catch up with Corbett and chat about his thoughts on Chicago, Istanbul, and of course Popular Pays.  

Q: Where did the idea for popular pays come from?
On some fateful day in October 2012, my co-founder Allan was drunk and leaning against our fridge when he said, "I want to throw a party that you can't get into unless you have 500 followers." True story.

Q:  Are there vendors/businesses that work better with Popular Pays than others?
It works when you have a product worth sharing. But then again, in this digital age, if you don't have a product worth sharing then you don't have a product at all.  

Besides that, it helps to have a well-lit space. We've shown that Pop Pays works for everything from a cup of coffee to a skydiving trip, but it can be hard to take a photo in a really dim bar or restaurant. Still, our users have surprised me – I've seen some really good and creative pics in spaces I didn't think would work too well.

Q: How does the process of creating transactions/barters work?
In terms of the process, it's simple:

•Users look at our app to see what Swaps are available to them (we call deals "swaps" as in swapping your social currency for a product) 

•They pick one.

•They extend their phone to the cashier to confirm the transaction; the cashier swipes the screen to confirm (just like you swipe a screen to unlock an iPhone). 

•The cashier gives the user the product that appears on the screen.

•The user shares a photo (we don't charge merchants unless a photo is posted. Even if users don't post, it's still worth the merchant's time: 23% of our users in August bought an extra product once inside the store. And they often become long-term customers – something we're working on tracking.)

Q: What if I only have 100 Instagram followers, can the platform provide value to me?
Not yet – we've started out by focusing only on Instagram, and only with those who have 500+ followers. But we think social currency is universal, and we do plan on expanding in terms of opening it up to everyone and every network.

Q: How do you and your co-founders (Allan Holmes & Nathan Michael) work together, who does what? 
Between myself/Nate/Allan, we act as GM/Biz Dev/CMO, but it all blends together. And we live together, so we have those roles too. Those are more like Chef/Interior Decorator/Social Butterfly.

Q: So whats the deal with Istanbul topping the leaderboard? 
They love us over there! And we love them. We asked our followers on Twitter to vote with a Tweet to pick what city we go to next, and Istanbul is kicking ass: seventeen tweets in the first two weeks after we started asking people to vote.

Q: What has it been like working out of Chicago's 1871? 
Phenomenal. The network effects are a huge plus. We've met everyone from mentors to experienced lead developers. Plus it's open 24/7 with super-fast wifi and a better selection of food than your neighborhood 7Eleven. There's even an Intelligentsia inside the space. And scooters and skateboards lying around. Start-up heaven.

Q: What other startups or founders do you look to for inspiration? 
Elon Musk – it's pretty cool to make your millions and then bet it all again on a new project. There's also that dude who named his company after a fruit. He was OK too.

If you were to guess how Gerome Sapp would follow up a successful career in the NFL, stastistically speaking, tech startup founder shouldn't be your first guess.  Sapp however will be the first one to tell you,“I’ve been beating statistics all my life.” Sapp first began to stand out during his high school football days in his hometown of Houston, earning all American honors as a defensive back and ranking highly on numerous lists for top high school players in the country.

After a stellar four years of playing safety at the University of Notre Dame, Sapp was drafted to the NFL, where he excelled as a member of both the Baltimore Ravens and the Indianapolis Colts.  Searching for something beyond his football career, Sapp took his first shot at entrepreneurship with a sustainable apparel company called Morph & Thro, which he founded along with two other former Notre Dame football players in 2008.  Starting the company from scratch, Sapp learned the important lessons of building a business from the ground up, but the lesson of persistence was the one that stayed with Sapp the most.  “I knew next to nothing about the apparel business, especially sustainable apparel,” Sapp said, “but it was something we believed in.  I know it sounds cliché, but I really discovered that it you are really passionate about something and you really believe in it, you can do anything you want to.” 

Sapp’s years spent on the football field gave him a competitive edge and bolstered his earlier attempts at founding a company, but as he explained, it was a magazine article that led him to his newest and most recent venture.  The subscription to Entrepreneurship Magazine from his aunt opened up Sapp’s eyes to the fascinating intersection of technology, innovation, and entrepreneurship.  In particular, Sapp remembers an article featuring Groupon as “a business created to service the needs of thousands of different companies.”  Powered by his newfound appetite for technology companies and revived interest in brands and social influence, Sapp began to draw out the high level concept behind Fluencr, a social media marketing platform for brands and their top ambassadors, eventually putting it down on paper and taking concrete steps to launch the business last year.

Fluencr helps brands identify and utilize built in ambassadors by leveraging and rewarding their existing social media influence.   By using Fluencr, major companies identify and connect with individuals who prove they can be socially influential for their brands.   Additionally, by linking their major social networking accounts like Twitter and Facebook to Fluencr.com, consumers who prove their social influence to the brands and their accompanying social media campaigns can get rewarded based on how much attention they bring to the brand.  So a fan of Nike with a couple hundred twitter followers could tweet a picture of his or her favorite Nike basketball shoes and potentially get a new pair for free.   Users can also get their friends to join in and create teams to promote social media campaigns of their favorite brands.  

 Attempting to solve the lucrative issues of social media ROI is a problem all companies big and small face. Fluencr provides the answer by tracking, measuring, and scoring all the social engagement a user generates from their action, determining their effectiveness in generating social buzz around the brand and their content or products. In addition to creating a valuable and measurable connection between brands and their top ambassadors, Fluencr has the ability to tap into any social network’s API and gather potentially helpful data for its users from that network.  

As Fluencr’s founder and CEO, Gerome stays quite busy, especially when it comes to traveling the country to pitch Fluencr to potential clients and investors. “The overall response has been extremely positive because any time brands can get some real ROI numbers, they really appreciate it and can understand the benefit,” said Sapp.  While his message and pitch for Fluencr has remained the same, Sapp admits he has worked on tweaking the delivery over time to make it more efficient in order to appease the occasional short attention span here and there. 

While excited about the prospects of Fluencr and its ability to easily access ambassadors and connect brands with them, Sapp took some time to reflect on what he has learned so far during his new career as a startup founder and entrepreneur.  “Make sure you know what you are getting into and the challenges that come with being an entrepreneur,” Sapp advises.  “Not everyone can take being told no or this won’t work for 364 days out of the year, but you still have to go in on that last day knowing your right.”   Without a doubt, Sapp’s success and experience on the football field has carried over into his journey as a startup founder, giving him the proper mindset to succeed with Fluencr going forward.  

“I learned in football, you’re going to lose a game or have a bad one, but that’s life.  What you do that next game or next play is what matters, and that mentality has followed me into the business world,” Sapp said. “Now that I no longer compete on the football field, my competition is in the business world, it’s just a matter of how much work I can put into it.”  

Gerome Sapp cites Entrepreneur Magazine, Fast Company, Inc. Magazine, and Mashable.com as good resources to keep abreast of what’s going on in the business and technology worlds. Feel free to add any other sites/blogs/resources you use in the comments below.