Bringing Entrepreneurial Thinking to an Old Business Model

Kaihan Krippendorff
September 29, 2022

What is your position with Outthinker?

I’m the founder of Outthinker. We started in 2004 as a traditional consulting firm but soon realized that we needed to approach things differently. We changed the name in 2010, and started talking about outthinking, a term for spotting innovative opportunities others ignore, challenging accepted dogma, and unleashing disruptive strategies. We wrote a book called “Outthinking the Competition” in 2011 and realized it spoke to people, so we moved away from traditional consulting to a membership model, called the Outthinker Strategy Network.

How did this organization get started?

In 2004 I was working for McKinsey & Company and wanted to seize that moment to promote, research, and write books full time. I started to realize my passion for speaking events. It grew from there and became a life of its own. We trained others in the Outthinker Process – a proprietary framework to help companies generate unique and innovative strategies – and trained companies such as Microsoft, JP Morgan Chase, L’Oreal, Raytheon, refining the program as we went along.

Today, the Outthinker Process is a systematic framework to design your strategy that has helped companies accelerate their growth by 50%. There are five steps: Imagine, Dissect, Expand, Analyze, and Sell (together they spell out IDEAS). Going through the steps helps teams develop a common language to discuss strategy and innovation and gives them a process they can use not once, but repeatedly, to come up with strategic options that their competition will not expect.

What have been some of the biggest accomplishments made during your time with them?

We’ve seen a lot of exciting client success stories. MacMillan Publishing launched two new businesses based on ideas that came out of applying the Outthinker Process. One of those businesses, Fierce Reads, is an innovative way to help authors find their audience and create novels. Another idea, in the science industry, is an alternate way to peer review scientific journals.

Internally, our biggest accomplishment took place in early 2020, when the entire speaking industry was disrupted by Covid-19 lockdowns. We put our heads together to brainstorm, “What could we do with a bunch of speakers who were all stuck at home?” and pivoted quickly. Once we had the idea, we didn’t sleep. We put together a one-day, 24-hour virtual summit featuring more than 20 influential thought leaders. We were proud to have some of the best-known authors and speakers, such as Rita McGrath, Scott Galloway and Salim Ismail participating. Participants from Europe, the Middle East, Southeast Asia, all over the world participated. We raised more than $180,000 for Covid charities.

Other accomplishments we’re proud of include publishing five books and working with some amazing clients: JP Morgan Chase, Cisco, Boston Globe, Bank of America, Procter and Gamble, IBM, Equifax, Notre Dame University and Shell. We have grown our membership group, the Outthinker Strategy Network, to bring together heads of strategy of multi-billion-dollar companies to share ideas and help each other deal with strategic challenges.

What limitations does an old business model have?

One problem that we hear over and over from our network of chief strategy officers, is legacy business models are limited by quarterly profit goals. It’s fundamentally hard to think a few years into the future and be disruptive if you are only focused on what’s happening in the next three months. Hierarchical organizational models also make it difficult for employees at all levels to move quickly, take charge, and innovate. It’s a problem we spend most of our days thinking about and trying to solve.

What advice would you give to people wanting to bring in entrepreneurial thinking to their business?

We’ve spent a lot of time studying internal innovation and what inspires it. Most employees want to be creative and innovative, but there are specific obstacles they face that hold them back. We’ve come up with seven areas that will break down those barriers and unleash entrepreneurial thinking:

1. Activate intent

2. Make sure everyone in the company understands what your strategy is

3. Generate lots of options

4. Train employees to design new business models that do not threaten the existing business model

5. Empower employees to conduct experiments

6. Pull together a cross-functional team to propel ideas forward

7. Put structures in place to reward and celebrate innovation

What are the benefits of bringing in this mindset to an organization or company?

New research that we are working on shows there is a strong correlation with activating entrepreneurial mindset and attracting top talent. It increases revenue growth and the value investors place in your company. Generating growth from within is more valuable in the long-term. Employees feel inspired and empowered to make decisions which enables them to take action more quickly, which then results in a more customer-centric culture.

How can associations thrive and grow to stay relevant?

We think that traditional standalone companies will move to ecosystem models to serve greater purposes and solve bigger challenges than competition and profit. As companies fragment and work together in different ways, the association will become the critical glue around those missions.

We’re also working on a new book, Proximity, featuring a chapter focused on healthcare and medicine. The book describes how company strategies are shifting to a world where goods and services are delivered increasingly closer to the point of demand in time and space. If you want to understand where the world is headed, envision a future in which we identify and provide cures for illness at the moment care is needed.


The list below reflects the most common barriers and their solutions.

1. Intent: Facing early obstacles, many would-be internal innovators abandon their intent. They eventually give up looking for chances to innovate. Successful ones keep their intention alive and are more likely to spot innovation opportunities.

2. Need: Most employees do not understand the innovations that their organizations need. Even if they are inspired to look for new ideas, they look in the wrong places and propose ideas of little strategic value. Successful ones take the time to learn market forces affecting their company, understand what their organization cares about, and sense unmet customer needs. 

3. Options: Would-be internal innovators often grow frustrated because they become fixated too early on a few innovative ideas–or worse, just one. It’s much more strategic to continually generate new ideas and manage them like a portfolio of options. 

4. Value blockers: Innovative ideas often conflict with a company’s current business model. Successful innovators find ways to engineer their ideas, so that rather than conflicting, they enhance the company’s standing.

5. Act: Established organizations often ask employees to prove that an idea will work before giving permission to take action. This puts would-be internal innovators in a Catch-22: They can’t take action, so they can’t prove that their idea will work, so they can’t take action. Yet, most new ideas are better suited to the opposite approach—taking action in order to prove the idea—and successful innovators devise ways to do just that.

6. Team: Corporations hamper internal innovation through their structure: They use siloed hierarchies, act slowly, and value results over learning. Successful innovators recognize that pursuing new ideas often requires the opposite, and so they pull together a cross-silo team that runs at a rapid pace and is geared toward learning rather than delivering results.

7. Environment: Getting support for new ideas is politically complicated because the leadership behavior, types of talent, structures, and cultural norms that help established organizations operate tend to hinder creativity. Successful internal innovators find “islands of freedom” from which they can access the talent, structures, cultural norms, and leadership that support innovation.

Ready to learn more? Head to the latest episode of House Call – An Affinity Strategies Podcast hosted by Claire Vincent. Kaihan shares the advantages of an entrepreneurial mindset including cultivating a positive environment for innovation and how innovation manifests in health care: