2016 Chicago Innovation Awards Summit

Highlights from the 2016 Chicago Innovation Awards Summit:

~ Talent & Disruption ~

~ Raising Capital ~

~ Entrepreneurs ~

~ The Panel ~



I: Navigating the warp drive when:

• Population growth and human migration are running at unprecedented levels
• Technology is evolving faster than education
• The skills gap is widening

migration map

We live in exponential times; this is not news. It’s merely fact. Human migration is at unprecedented levels, and while our Labor markets see increased supply and increased demand (which is good), the requisite skills gap is widening not narrowing (not good).

Skills Gap

In this Venn Diagram, Utopia would see a total eclipse, a single circle, but the pace of change is pulling these circles of supply and demand wider apart, the intersection where the skills available align with the skills needed, is shrinking.

For all of us this shift presents the opportunity to be more self-aware and adapt new skills through continuous improvement.


II: Analog vs. Digital

Our analog career model might have looked like this:

  • Go to school – learn skills – specialize – join a company – apply those skills – refine those skills over timeretire. With probably only 1, 2 or maybe 3 companies on your resume

A digital career model might look more like this:

  • Go to school – learn skills – specialize – join a company – apply those skills – acquire new skills as well as refine the oldretire (later, and plan to live longer). With probably 13 – 18 companies on your resume

This shift creates a challenge made all the more acute by the relative speed at which it is occurring. But the greater the challenges the greater the opportunities.

III: Change = Opportunity

These shifts in our labor markets create new ways to differentiate value for both employers and employees.

  • Employers of choice will do more to nurture talent and provide greater access to training, development and mentoring. While employees of choice will demonstrate ownership of their personal and professional development, as well as possess higher levels of self-awareness and an appetite for continuous improvement
  • Employers of choice will review performance in real time, through frequent and ongoing employee engagement, not through the lens of annual snapshots. Employees of choice will take ownership of every review, identify their own skill gaps, and share how they, the employee, plans to close them and in-so-doing add greater value to the organization
  • For employers, these changes present opportunities to adapt and attract (and better retain and engage) employees of choice. For employees, these changes present opportunities to adapt; to develop and demonstrate greater self-awareness and continuous improvement behaviors, and thereby both differentiate and increase their own market value

IV: Tours Of Duty

For Microsoft and LinkedIn this change presents a revenue opportunity: and her name is Lynda.


Mike Gamson, SVP Global Solutions, LinkedIn, provided a glimpse into our future, as LinkedIn might see it:

LinkedIn has unprecedented access to industry data with respect to labor and employment. LinkedIn can see (and can share) where these skills gaps reside, be that by vertical, geography, or even socioeconomic factors.

LinkedIn’s Lynda provides access to learning resources to help close these gaps.

By providing members with insights, (provoking self-awareness) LinkedIn might say to a member:

“Hey, we see you’re interested in Xyz position at 123 company, however you don’t have Abc skills or qualifications – and we can help connect you with the right resources…”

Providing access to online learning through Lynda, LinkedIn offers raw material for continuous improvement.

Oh, and if you’re not familiar with the MOOC List yet, either as an employee or employer, I guarantee you will be, and way before 2020.

V: This shift is only the beginning

Maeve Lucas, Managing Director of Talent Strategy at Accenture, provided a glimpse into our future, as Accenture might see it:

Maeve Lucas

Accenture’s publication: Workforce Reimagined: A collaboration at the intersection of humans and machines, provides in-depth considerations, including how machines (both the robotic and the artificially intelligent) will continue to blend in and alter our perception of the workplace.

The concept of a peripatetic labor force is perhaps as old as the words itself, however the increasing potential for the Uber-ization of labor – flexible, freely moving from project to project, where output and results are the motivation and reward – is another example of how technological advancement is changing the labor landscape.

Listening to these Chicago Innovation Summit Presenters, reminded me of the adage: that much of what helped you get here, won’t help you get there.

I believe higher levels of self-awareness and a passion for continuous improvement will increasingly become the differentiating factors in our value proposition, be that as employees or employers of choice.


I: The Landscape Today:

• Local Angel Markets are thriving, helped by lower costs required to start a venture, and a growing investor confidence following a string of great exit stories in the area. I’d venture this activity is also helped by a lack of higher yields available in other traditional (lower risk) investments, which is all good news for entrepreneurs and venture fund managers

• Illinois Venture Capital Association (IVCA) members manage more than $100 billion in investments in private companies

• An example fund includes: The Illinois Technology Development Account (TDA), a $75 million fund created in 2003 by the Illinois General Assembly, which has created more than 3,000 jobs and attracted private capital to Illinois companies, while earning a positive return for taxpayers

• The Illinois TDA is increasing threefold to ~$220m

• This investment fund isn’t funded from operating expenses, but rather through a change in mix of state investment funds, likely diluting bond allocations, in favor of creating the associated stimulus (employment and tax revenues) and the opportunity for higher yields, fueled by increasing confidence, following recent successful exit stories

II: How Does a Private Equity or Venture Capital Fund Typically Work?


The IVCA provides a cool Info Graphic, like this one above, to help simplify the answer. You’ll also find additional resources and contact information all through their website: www.illionoissvc.org

III: Advice When Pitching:

• It’s not all about you: Open your pitch with how the VC is going to make money: you have at best 30 seconds to catch their interest, and in all likelihood less than 10 seconds to bate your hook. Be prepared, because if you miss, they may literally walk out on you

• Okay, now it is all about you: They’re hooked (good) now as you reel them in it’s not the line of your [really awesome] idea they’re evaluating. It’s you: how buttoned up, committed and capable are YOU with execution?

• But, you’re not that special: There are innumerable opportunities and innovative ideas out there. Investors are surrounded by opportunities, they’re not actually looking for another one, they’re looking for the one: the person or people who they believe can and will execute an awesome idea

• And now you are that special: Okay great, you’ve got a neat idea, but can you really convert it into an output, profitably, and within the laws of physics when it comes to liquidity? Probably, yes, but you’re also going to need to surround yourself with talent

• Lastly, consider what inspires others: You have a great idea that could improve the lives and livelihoods of others you might find you attract more investors, when they believe in both you and your mission. Whereas if you have a great idea that doesn’t go much further than to serve your own ego, don’t be too surprised if you don’t secure the support you’d hoped for


IV: Company Sale or IPO: How much further is it?

For IPO, Pam Buchanan, Managing Director, NASDAQ says, current lifecycle timelines for reaching IPO are trending at between 8 and 10 years

Top Tip: put the groundwork in early on laying the foundations for solid financial processes and the executive readiness for the rigor and scrutiny associated with going public

Consider how neglecting or compromising on this rigor at the upfront will cost you more on the back end, both time and money, put the foundations in early (if you can) and you’ll spend less in the overall

V: For Sale or not for Sale

“[For] that is the question: Whether ’tis nobler in the mind to suffer the slings and arrows of outrageous fortune, or to take arms against a sea of troubles” ~My sincere apologies to William Shakespeare, Hamlet, Act 3 Scene 1


Given the inherent risks of survival (according to Forbes 1 in 10 new ventures fail) it’s perhaps not surprising, and not unreasonable, that so many companies, from Idea stage, through to the phase of New, and early Growth stage, put every available dollar into product, service, brand, marketing and sales – to survive they may well have no choice

But for certain, whether it’s IPO or an M&A Sales Transaction, when critical mass reveals an inflection point is on your horizon, you’ll need a revolution in your finance function in order to maximize your hard earned and hard won value prop, then re-enegage those afterburners to navigate and survive due diligence

I’ve successfully navigated exactly this phase in the business life-cycle of founder-owned Technology & Services companies, both here in Chicago and London. For more on this, read my Linked In post: Veni | Vidi | Vici




I: Foster a culture that challenges conventional wisdom


Challenge: Moving borrowed life-size, replica, wild animal, stage props across neighboring states for a pop-up promotional event

Innovative Action: transport the props on an open flatbed (rather than a conventional closed container truck) and during the day rather than overnight

Result: Vastly increased promotional reach and awareness with minimal incremental cost to timeline or budget

II: Think big, re-imagine the overlooked or the everyday


Challenge: re-purpose extensive and redundant payphone architecture in NYC

Innovative Action: leverage the same culture that thinks and behaves per #1 above, to re-imagine and redefine what’s possible, then walk the talk, put in the effort, and respond to the de Blasio Administration’s RFP

Result part I: win the RFP and be attached to a groundbreaking project with LinkNYC: a first-of-its-kind communications network that will replace over 7,500 pay phones across the five boroughs with new structures called Links. Each Link will provide super-fast, free public Wi-Fi, phone calls, device charging and a tablet for Internet browsing, to access city services, maps and directions

Result part II: find your company on Google’s most wanted list for acquisition

Innovation NYCLink

What I loved most and took away from Chris Pezzello’s presentation was how he and his team had not let their association with transit advertising define (or confine) their potential for re-imagining human interactions, connectivity, and advertising within urban spaces.

III: Think Big, or Think Sideways, but most of all Think

Sam Yagan asked us to think about the difference between Spark Notes and Cliffs Notes. The key difference being, there isn’t one, except Spark Notes was born online and Cliffs Notes wasn’t.

Today the Cliffs Notes landing page describes itself as “CliffsNotes — the original (and most widely imitated) study guide” – ouch!

Cliff Notes

I can only speculate that the Cliffs Notes board might still be feeling the sting from a drop in shareholder value after losing (monopoly) market share through a lack of forward thinking and requisite innovation – maybe?

Doubtless they’re scrambling to regain market share, but a generation (or two) has since moved on.

With hindsight it would have been far easier for the incumbent to remain dominant and out in front, but they didn’t.

IV: Lessons learnt along the way

Having sold his first company at 22 years of age, Sam Yagan achieved a great deal early on, and he hasn’t stopped, therefore I found his firsthand insights all the more fascinating and intriguing


With hindsight Sam appeared to regret the timing of his selling Spark Notes. Implying to me that perhaps the $30m valuation was premature. Or that perhaps post acquisition, Barnes & Noble didn’t do more with the potential. I don’t know.

My take away is that in business, when we are in the moment, we never know for sure if we’re hitting the sweet spot (to use a golf or tennis analogy). Or as an artist once observed, when is it time to put down the brush? When does one more stroke detract from perfection rather than add value to it?

>Evaluating talent:

• Sam Yagan places a high value on those who have a clear idea about how they are going to help solve meeting the challenges the enterprise is focusing on, and he looks for this when interviewing talent

Keep Calm

• Sam also prefers higher levels of emotional intelligence (EI), and consequently looks for people who demonstrate a lack of drama. For a super quick overview on EI and its value in business and life, see my blog post: Keep Calm & Carry On

>Navigating Business Life-cycles:

• Having successfully navigated business life cycles, from an Idea Company, to New, then Growth, and Mature; Sam Yagan echoed Pam Buchanan’s earlier observation, that Executives add real value

• Sam also acknowledged this value was not apparent to him when starting out, but proved itself true as these milestones of business transformation were reached

From my own experiences, given the inherent risks of survival (according to Forbes 1 in 10 new ventures fail) it’s perhaps not surprising, and not unreasonable, that so many companies go through these stages putting every available dollar into product, service, brand, marketing and sales – to survive they may have no choice.

But for certain, whether it’s IPO or an M&A Sales Transaction, when critical mass reveals an inflection point is on the horizon, you’ll need a revolution in your finance function in order to maximize your hard earned and hard won value prop, then navigate and survive the associated due diligence.


>OkCupid | Match.com | Tinder:

With OKCupid, Sam explained how the material differentiation came they decided to share with users the data insights that were available.

Other online dating service providers had access to similar data, but chose to remain silent or clandestine. Perhaps fearing the user would be deterred from participation if they were fully informed of the typical success ratios.

But by sharing the insights and telling members a 3 in 10 response rate was the norm, the market responded well, seemingly appreciating and valuing knowing how the individual stacked up against the average experience.

Tinder now brings the game-ifi-cation of dating, in App, and mobile. The press may not often portray Tinder as tender, but it’s certainly caught fire.

Sam Yagan echoed the Innovation Summit Panel’s observations on creating a culture that is allowed to fail in order to see innovation thrive.

Tinder, by example, came out of exactly such an environment, and while it (is perhaps) the one in many that survived outside the sandbox, the receptivity is undeniable:

• 100 million downloads (3/6/16)
• 10 billion matches (3/25/16)
• 1.4 billion swipes PER DAY (2/21/16)


I: Innovating vs. Impersonating

• Innovation, a word sometimes used when impersonation is what’s really happening. Metaphorically speaking, perhaps the emperor, or CEO, wears no clothes if boasting of innovation, when in truth the need for change is being driven by merely copying others and trying to keep up. Your employees can see through it. How might this manifest in performance and behavior?

Innovation Bright

II: Embrace failure | Failure is just feedback

• To be truly innovative you must create a business culture that allows for failure, else how can you expect true innovation. “Steve Jobs didn’t succeed in spite of his failures, he succeeded because of his failures” Failure is feedback

• A culture that says ‘It’s okay to fail’ (so as long as you truly tried) will empower courage, ownership and foster loyalty

III: Interview questions for candidates

• What do you see that we’re doing that we could improve and you could help us address?

• Look for people who can demonstrate in their own lives how they’ve overcome a challenge, demonstrated resourcefulness, acted on their curiosity, proven their determination and taken ownership of their destiny

shradha agarwal

• Look for people who don’t seek perfection – consider if perfection is merely a self-made illusion, a perverse form of procrastination
• Consider “scrappy perfection” – if it’s good enough, and if it’s the best there is for xyz reasons, then it will do – for now

IV: What gets measured gets done:

• Be honest with yourself: how is innovation evidenced, recognized and measured through your performance review process?

• Take the blame, share the fame, make sure you’re not the smartest guy in the room

• Is innovation embedded in the culture, from the top down, or is simply paid lip-service, but no aligned with performance, review and rewards?

V: What’s The Mission:

If your walking mantra is “I want to be a billionaire” then you’re probably not going to make it.

If your walking mantra is “I want to solve a problem, for the betterment of others” then you might.

The mission, the why? has to be bigger than you. It can’t just be about you. And if people believe in the why, they will take risks, even the biggest risks of all.


As a NASA astronaut, Dr. Mary Ellen Weber put this into context for me when explaining considering going into space. A pursuit where the risks are both high and extreme, and for which NASA provides no insurance. I did learn that an astronaut may however approach Lloyd’s of London for coverage, if they wish!

The mission, the bigger picture, is what motivates and drives the team, and has them taking ownership and being willing to take calculated risks, even with their own lives.

For further context Dr. Mary explained how the historical statistical data available for space flight correlates to an equivalent of 10 commercial air distastes per day between O’Hare and DFW.

No one (in their right mind) would take those risks, certainly not for you, nor for themselves; but for the mission? well then they just might, and we know that they do. You have to believe in something bigger and greater than yourself.

Listening to Dr. Mary reminded me how my late Grandfather, serving as a British Marine throughout WWI, and whenever asked: “If he served King and Country?” would reply: “Just Country”

Innovation Blue

From right to left the Chicago Innovation panel comprised:

• Michael Krauss (Moderator), President, Market Strategy Group
• Ed Wehmer, President & CEO, Wintrust
• Hardik Bhatt, Chief Information Officer, State of Illinois
• Brenna Berman, Chief Information Officer, City of Chicago
• Shradha Agarwal, President & Co-Founder, Context Media
• Dr. Mary Ellen Weber, Founder, Stellar Strategies & Former NASA Astronaut

Warm thanks to the following Chicago Innovation Summit Contributors:

• Tom Kuczmarski (Interviewer), Co-Founder, Chicago Innovation Awards
• Bruce Leon, President, TandemHR

• Maeve Lucas, Managing Director of Talent Strategy, Accenture
• Mike Gamson, SVP, Global Solutions, LinkedIn

• Kevin Willer (Interviewer), Partner, Chicago Ventures
• Maura O’Hara, Executive Director, Illinois Venture Capital Association
• Pam Buchanan, Managing Director, NASDAQ

• Chris Pezzello, Vice President and General Manager, Intersection
• Sam Yagan, Vice Chairman, Match Group

The event was sponsored by Chicago Innovation Awards & The Executives Club Of Chicago

My own special thanks to

• The IVCA for forgiveness in the use of their info-graphic
Phys.org for forgiveness in the use of their info-graphic
Special Ramblings for their data on Tinder adoption and usage
Forbes for their data on Start Ups and M&A Success

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