Brad Keywell

FounderPortfolioVideoNewsBlog

Brad Keywell

Brad's Annual Gifts

Hero Image

Year-End Gift: 2025- You Get to Choose Your Game. Choose Wisely.

Hero Image

Year-End Gift 2024: The Story of Time

Hero Image

Year-End Gift 2022: The Experiment of Life

Hero Image

Year-End Gift: 2021 – What Will You Do?

Hero Image

Year-End Gift: 2020 – It Starts With An Idea

Hero Image

Year-End Gift: 2019 – The Time Is Now

Hero Image

Year-End Gift: 2018 – Get Moving

Hero Image

Year-End Gift: 2017 – Great Ideas Start Here

Brad’s Blog Posts

Thoughts, Art & Other Fun Content(47)

Sam Zell, My Mentor (and His Two Final Gifts to Me)

Sam Zell, My Mentor (and His Two Final Gifts to Me)

  • May 23, 2023

  • Entrepreneurship
  • Life

Sam Zell was an iconoclastic risk-taker, adventurer, contrarian, industrialist, and quite simply one of the great entrepreneurs of our time. For me, Sam Zell was my mentor. And less than two months before his passing, he gave me two precious gifts.

GENERATION: RE – The Official Nomination

GENERATION: RE – The Official Nomination

  • March 23, 2023

  • Business
  • Life

Every generation is given a name – some more accurate than others. Consider this my nomination for the official name of the emerging generation (those born in 2000 to today): Generation:RE “What’s in a name?” mused Shakespeare. Demographers create generational groupings to examine economic trends and social changes over time. These groupings take on names, some […]

9 Takeaways from 9 Years of Chicago Ideas

9 Takeaways from 9 Years of Chicago Ideas

  • October 28, 2020

  • Entrepreneurship

The foundational design of Chicago Ideas is in sync with these times in which we find ourselves.

Two Pillars for Effective Remote Work: Asynchronous Clarity & Visible Value

Two Pillars for Effective Remote Work: Asynchronous Clarity & Visible Value

  • October 22, 2020

  • Business
  • Life

We are ten months into this everlong 2020. One hundred and thirty years ago, a German playwright first coined the phrase “Spring Awakening” as the title of his breakthrough play, first performed in 1891. It’s a phrase that comes to mind. It’s lingered in mine since March. This fall, our world is still awakening from this spring, although the “what” to which we are awakening is still not yet clear.

Being “In Integrity” with Yourself and Others

Being “In Integrity” with Yourself and Others

  • October 06, 2020

  • Life

I first learned about integrity from my parents, often in reaction to testing the rules — in particular, I remembered “borrowing” something from home and taking it into my third-grade classroom for show-and-tell, mistakenly leaving it at school, and then claiming ignorance of its whereabouts.

How We Overcomplicate Getting Better

How We Overcomplicate Getting Better

  • September 30, 2020

  • Entrepreneurship

I’d like to propose playing a game at work. For the sake of naming it, let’s call it the “Get Better At” game. The rules are simple: 1. Find a specific area/activity in which you or the team you’re a part of can get better. 2. Immediately develop a plan to get better. 3. Get on with it!

5 Tools to Learn How to Learn

5 Tools to Learn How to Learn

  • September 15, 2020

  • Education
  • Entrepreneurship

It’s been said that teaching is the art of awakening the natural curiosity of the mind. But how to teach best, and what lessons are the most valuable? Winston Churchill said “I am always ready to learn although I do not always like being taught.”

3 Challenges Data Science and Shale Production Share

3 Challenges Data Science and Shale Production Share

  • September 14, 2020

  • Business
  • Technology

Like shale production, data science is challenged by extracting, refining, and controlling the input that makes it productive. If data is the new oil, it’s a lot more like shale than fresh crude.

Beware of the Apostrophe Ts

Beware of the Apostrophe Ts

  • September 10, 2020

  • Entrepreneurship
  • Life

I’ve been in the groove of a morning habit. For a few minutes when I wake up, I try to just sit in bed and think. Not that long — but enough time to give some consciousness to my unconsciousness (a/k/a my dreams) and see what comes to mind as I greet the new day. One of the first mornings practicing the habit, something came to mind that I immediately wrote down: “beware the Ts — ask why.”

Interview Someone You Love

Interview Someone You Love

  • September 03, 2020

  • Entrepreneurship
  • Life

Of course, you should also interview your colleagues (whether you love them, like them, or barely know them). And there are lots of other people in your life, I’m sure, with whom an interview would open your mind, open their heart, and open new possibilities. But let’s start with an interview — your interview of someone you love.

Why We Must Learn the Other Montessori Method

Why We Must Learn the Other Montessori Method

  • August 31, 2020

  • Education

Maria Montessori saw clarity through the noise. The noise — decades of education to teach her about how to preserve the order of so many things, a level of education that would clutter most brains and leave people with little room for originality and creativity.

Long Live the New (and Improved) Corporate Org

Long Live the New (and Improved) Corporate Org

  • August 21, 2020

  • Business

The corporate matrix is dead. As the coronavirus crisis has set in, workflows are transitioning to asymmetric and entrepreneurial teams, especially at tech companies. Many organizations elsewhere have failed to get rid of the corporate matrix. The matrix creates dual reporting relationships for a single employee — one functional, one product-oriented.

9 Decision Biases & How to Control Them

9 Decision Biases & How to Control Them

  • August 17, 2020

  • Business
  • Entrepreneurship
  • Life

I can tell you one thing for sure — I have made lots of mistakes. Lots and lots of them. And that’s where the fun really happens — as an entrepreneur, the fun is trying to figure out which moves are mistakes, and which are logical and rational steps towards something valuable and important.

Why You Must Prioritize a Quick No

Why You Must Prioritize a Quick No

  • August 10, 2020

  • Business
  • Entrepreneurship
  • Life

No. That’s right, “no.” And quickly. Ok — I know I’m in Jeopardy format. So, the question is this: “What’s the next best thing to a quick yes?” A quick “no” is not easy, but it’s necessary. To be impactful and purposeful with collaborators, prioritizing a quick “no” is the next best thing to a quick “yes.”

What Is Your Mindset?

What Is Your Mindset?

  • July 22, 2020

  • Entrepreneurship
  • Life

You’ve heard it over the years from parents or perhaps from teachers: “you can do anything you set your mind to.” It’s interesting that the reference in the saying is literally about “setting” your mind.

Bad Data Leaves Money on the AI-Enabled Factory Floor

Bad Data Leaves Money on the AI-Enabled Factory Floor

  • July 08, 2020

  • Business
  • Entrepreneurship
  • Technology

Opportunity & Unrealized Potential. Manufacturing industries are failing to capitalize on the tremendous potential of artificial intelligence and machine learning. While some may blame the limits of technology, a dearth of data science talent, or the resistance of workers rooted in inertia, the root cause of the friction is a lack of data integrity.

Four-and-a-Half Rules You Must Break: A Message to 2020 Grads

Four-and-a-Half Rules You Must Break: A Message to 2020 Grads

  • June 15, 2020

  • Education
  • Entrepreneurship
  • Life

Class of 2020, I’m here to tell you that you need to break some rules. But first I’d like to tell you about five monkeys, a group of scientists, an experiment. And some bananas.

Appreciation: The Common Thread of Commencement

Appreciation: The Common Thread of Commencement

  • June 03, 2020

  • Education

One of the greatest graduation speeches of all time (in my humble opinion) was delivered by the late author David Foster Wallace to the Kenyon College class of 2005.

Out of Many, One

Out of Many, One

  • June 03, 2020

  • Life

In this moment, one truth arises above all else: Black lives matter. I do not claim to understand the experience of being Black in America. I do, however, claim to care that the experience of being Black (or any skin color, ethnicity, or orientation) in America should bring with it the same rights and privileges and protections and treatment as that of being white.

The Golden Links of Destiny

The Golden Links of Destiny

  • April 28, 2020

  • Life

I believe we humans are far too often guided (and, sadly, irrationally crippled) by fear or by a default setting pointed towards ‘longstanding tradition’ (which often proves baseless).

What I’ve learned about scaling a Platform company

What I’ve learned about scaling a Platform company

  • December 05, 2019

  • Business
  • Education
  • Entrepreneurship
  • Technology

This month, Uptake signed the 20th partner in our Platform ecosystem. These collaborators range from companies that maintain some of our country’s largest manufacturing plants to providers of edge devices for our leading utilities.

An Even Better Education: Learn How to Learn, Not Just What to Learn

An Even Better Education: Learn How to Learn, Not Just What to Learn

  • November 20, 2018

  • Education
  • Entrepreneurship

Teaching is the art of awakening the natural curiosity of the mind. But what lessons are most valuable? Most of our years in classrooms consist of listening, memorizing, regurgitating — and then repeating that cycle. So I ask — were you taught how to learn?

How Can You Be More Creative? Embrace Daily Rituals

How Can You Be More Creative? Embrace Daily Rituals

  • October 12, 2018

  • Life

I’m fascinated with rituals. While habits are defined as “regular tendencies or practices,” rituals represent a higher level activity, “a solemn ceremony consisting of a series of actions performed according to a prescribed order.” Whether or not you realize it, your rituals are part of your secret formula for getting stuff done—and doing it well. Your rituals help define you—your beliefs, your activity, your soul.

Future of Jobs

Future of Jobs

  • September 10, 2018

  • Business
  • Life

Charles Darwin would have a lot to say about how humans will adapt to this Fourth Industrial Revolution. For one, I believe he’d tell us that we’ll evolve.

3 Hacks To Save Time And Energy

3 Hacks To Save Time And Energy

  • August 07, 2018

  • Life

Thomas Thwaites set out to build a toaster from scratch. (Photo Credit: Daniel Alexander.) I believe everything can be done faster and better, period. If you’ve ever spent time with me you would probably know that.

The next generation of U.S. global leadership in innovation will require closer collaboration between Technology and Defense

The next generation of U.S. global leadership in innovation will require closer collaboration between Technology and Defense

  • July 18, 2018

  • Technology

Driving on the freeway in the Bay Area today, you might find yourself surrounded by autonomous cars and trucks. Many people associate driverless vehicles with big tech from the West Coast — Uber, Google, and Amazon, to name a few.

Survival of the (Digitally) Fittest

Survival of the (Digitally) Fittest

  • June 11, 2018

  • Entrepreneurship

One the first American industrial magnates was also one of our first self-made entrepreneurs. He was a ruthless businessman, eliminating his competition by drastically reducing costs and cutting shrewd deals.

Technology is Solving the Wrong Problems

Technology is Solving the Wrong Problems

  • June 08, 2018

  • Technology

FaceTime with 32 friends, updates to Siri and a walkie-talkie on your Apple Watch are just a few of the feature update announcements coming out of Apple’s World Wide Developers Conference this week.

Dr. Irwin Adam Eydelnant: 4 Insights from the Mind Behind the Museum of Ice Cream

Dr. Irwin Adam Eydelnant: 4 Insights from the Mind Behind the Museum of Ice Cream

  • May 18, 2018

  • Entrepreneurship
  • Life

Dr. Irwin Adam Eydelnant, Founder & Creative Scientific Director of Future Food Studio and BEVLAB, is changing the way we think about food.

AI For Good…Maybe a Little Hope?

AI For Good…Maybe a Little Hope?

  • May 12, 2018

  • Life
  • Technology

As someone who lives on the front lines of AI at Uptake, I hear those terms and I react with optimism. Here’s why. Artificial intelligence (“AI”) and Machine learning (“ML”) are being used to do good. You might not read about it in the headlines, but it’s happening.

Tech must address problems of consequence, not just convenience

Tech must address problems of consequence, not just convenience

  • May 10, 2018

  • Technology

Americans are falling out of love with the tech industry. We shouldn’t be surprised. Positive news coverage of the tech sector declined from 60 percent to 16 percent between 1986 and 2013, according to a study last year by the Information Technology and Innovation Foundation.

The Upside Podcast – Dr. Irwin Adam Eydelnant: There Are No Rules

The Upside Podcast – Dr. Irwin Adam Eydelnant: There Are No Rules

  • May 09, 2018

  • Entrepreneurship
  • Podcast

Dr. Irwin Adam Eydelnant is a food design technologist known as the “Willy Wonka of Toronto.” As founder and principal of the Future Food Studio, he spins up out-of-this world experiences that have changed the way we interact with and experience food and drinks. And, unless you’ve been taking a hiatus from social media, you’ve surely heard about one of his most famous projects, the Museum of Ice Cream, where he served as founding partner of the museum’s NYC launch.

The Upside Podcast – David Axelrod: What Baseball & Politics Can Teach Us About Culture

The Upside Podcast – David Axelrod: What Baseball & Politics Can Teach Us About Culture

  • April 25, 2018

  • Life
  • Podcast
  • Sports

David Axelrod has been hailed a political mastermind. A former newspaper reporter-turned-political strategist, David has worked behind-the-scenes on more than 150 campaigns. His most famous client? President Barack Obama. From 2004-2012, David helped the President to three victories: the 2004 Senate race, the historical 2008 Presidential election, and his 2012 re-election, where he served as chief strategist and media advisor. Today, David is the director of the Institute of Politics at the…

What Baseball & Politics Can Teach Us About Leadership: 4 Lessons from Political Strategist David Axelrod

What Baseball & Politics Can Teach Us About Leadership: 4 Lessons from Political Strategist David Axelrod

  • April 25, 2018

  • Entrepreneurship
  • Life
  • Sports

On October 27, 1960 in New York City, five-year-old David Axelrod went to see John F. Kennedy on the campaign trail in Stuyvesant Town at the corner of 21st and 1st. As he sat on top of a mailbox and watched the young presidential candidate speak to the crowd, he had a sense that something big was happening.

The Upside Podcast – Sarah Feinberg: Lessons from the White House to Silicon Valley

The Upside Podcast – Sarah Feinberg: Lessons from the White House to Silicon Valley

  • April 10, 2018

  • Entrepreneurship
  • Podcast

In the second of The Upside’s series with political disruptors, Brad chats with Sarah Feinberg, former chief administrator at the Federal Railroad Administration (FRA). From the Hill to the White House to Silicon Valley and back, listen in as they discuss what she’s learned during her unique career. Feinberg – one of Uptake’s advisors – shares what it’s like to be inside the White House “situation room,” mitigating potential crude oil train disasters at the FRA, and influencing Silicon…

The Upside Podcast – Arne Duncan: Reimagining Chicago

The Upside Podcast – Arne Duncan: Reimagining Chicago

  • March 29, 2018

  • Life
  • Podcast

In the first of The Upside’s series with political disruptors, Brad learns about the big item atop Arne Duncan’s bucket list, the cause he believes to be the “ultimate non-political bipartisan issue,” and what it’s like to play basketball with President Obama. The former U.S. Secretary of Education shares his take on the future of learning: from leveling the technology playing field to streamlining college applications, and why we’re long overdue for big-time disruption. And, why data…

Building a Bucket List of Consequence: My Conversation with Former Secretary of Education Arne Duncan

Building a Bucket List of Consequence: My Conversation with Former Secretary of Education Arne Duncan

  • March 27, 2018

  • Education
  • Life

A few months ago I sat down with Arne Duncan for a conversation on The Upside. He’s well-known as the former Secretary of Education under President Obama, and as a pragmatic leader who spent his career pushing for innovation and positive change for students – a sometimes daunting task.

College Basketball Doesn’t Just Build Character, It Reveals Character

College Basketball Doesn’t Just Build Character, It Reveals Character

  • March 22, 2018

  • Entrepreneurship
  • Life
  • Sports

So said Marv Levy, the Hall of Fame NFL coach (and native Chicagoan). With the NCAA basketball tournament well underway, my version of that insight is this — college basketball doesn’t just build character, it reveals character.

Rewarding Brilliance, Creating Failure (and Innovation)

Rewarding Brilliance, Creating Failure (and Innovation)

  • February 15, 2018

  • Entrepreneurship
  • Technology

In 2008 and 2009, coders, mathematicians and at least one psychologist became singularly focused on one problem: Improving Netflix’s recommendation algorithm.

The Fourth Industrial Revolution Empowers People -Not Machines

The Fourth Industrial Revolution Empowers People -Not Machines

  • December 01, 2017

  • Entrepreneurship
  • Technology

Today, the World Economic Forum (WEF) named Uptake a Technology Pioneer, an exclusive list of 30 of the most innovative companies globally. Our company joins the ranks of Google, Twitter, Airbnb, and Mozilla.

Down, But Not Out: How Artificial Intelligence Will Save Industry From its Costliest Challenge

Down, But Not Out: How Artificial Intelligence Will Save Industry From its Costliest Challenge

  • August 20, 2017

  • Technology

One of industry’s biggest challenges is also its most expensive. Downtime is a multi-billion-dollar problem that’s continuing to grow larger and more complex. It’s an increasingly important issue facing global companies in today’s connected world.

Make Love and Belief Interchangeable

Make Love and Belief Interchangeable

  • March 20, 2017

  • Life

It’s rare that someone will question your love for your own children, but 10 years ago my friend Brandon did just that — and it changed the way I view my relationship with my daughters — now ages 15 and 16 — forever.

Best Advice: Change the Game

Best Advice: Change the Game

  • March 01, 2017

  • Business
  • Entrepreneurship
  • Life

When Jeopardy! producers told Arthur Chu he’d been selected as a contestant, he knew he wasn’t ready. But instead of giving in to eventual defeat, Chu hunkered down and began scouring the game show’s forums, watching — and rewatching — classic episodes on YouTube and even turning to IBM’s Jeopardy! contestant, the computer Watson, for inspiration.

The Internet: Turning Lemons into Lemonade

The Internet: Turning Lemons into Lemonade

  • March 01, 2017

  • Entrepreneurship
  • Life
  • Technology

Used car dealers get a bad rap. Sure, they have enshrined themselves in our society by their cheesy commercials, their sometimes sleazy business deals and, not to mince words, the often shoddy cars they offer for sale. But really, that’s not the fault of the car dealers — it’s human nature. A quirk of behavioral economics — the lemons problem, to be exact.

The Ultimate Entrepreneurial Risk: Student Debt (Flipping the University: Part 2)

The Ultimate Entrepreneurial Risk: Student Debt (Flipping the University: Part 2)

  • February 05, 2017

  • Education
  • Entrepreneurship
  • Investment
  • Life

In 2012, a team of ex-Google employees decided to launch their own company: a venture capital firm of sorts with a twist called Upstart. While traditional venture capital structures give funding to companies, Upstart’s financial backers monetarily support individuals. All they ask for in return is a share of future income.

The Next Cinderella Story

The Next Cinderella Story

  • January 07, 2017

  • Business
  • Life
  • Sports

One of my favorite sports teams is not one you’re going to see game highlights of on ESPN’s SportsCenter. In fact, you’ve probably never heard of them. The 2006 Redwood City 7th- and 8th-grade girls’ basketball team, however, is the stuff of modern sports legend.

In an Automated World, Human Connections Can Still Thrive

In an Automated World, Human Connections Can Still Thrive

  • October 22, 2016

  • Life
  • Technology

By Brad Keywell and Adam Waytz, Associate Professor at Kellogg School of Management at Northwestern University.

Brad Keywell

    FounderPortfolioVideoWords & Stuff

© 2025 Brad Keywell