What Entrepreneurs Can Learn from Socrates

What Entrepreneurs Can Learn from Socrates

Academic institutions worldwide, such as Stanford University’s Center for Teaching and Learning or Cornell University’s Center for Teaching Excellence, are searching for ways to improve learning outcomes – knowledge and skills that students take away from the classroom. These concepts are also finding their way into the entrepreneurial environment, as learning has become increasingly important in the today’s chaotic economy. [1]

Learning outcomes as a concept have been studied for thousands of years, reaching back to Socrates and his students. Socrates spent his entire life trying to understand a better way of conversation that could not only enlighten the student, but everyone in the classroom, including the teacher. His findings led to the creation of the Socratic method – a dialectical (discussion-based) process for the meaningful acquisition of knowledge.

Before we can appreciate the values that entrepreneurs can gain from the Socratic method, we need to first define the Socratic method and its role in entrepreneurial learning.

The Socratic Method (Re)defined.

Since Socrates never recorded his own teachings, our understanding of the Socratic method comes from the Socratic Dialogues, a series of stories written by his most famous student, Plato. The purpose of the Socratic method is to generate an open-ended discourse, so its own definition is vague and open to interpretation.

One way of defining the Socratic method is as “a systematic process for examining the ideas, questions, and answers that form the basis of human belief. It involves recognizing that all new understanding is linked to prior understanding, that thought itself is a continuous thread woven throughout lives rather than isolated sets of questions and answers.” [2]

Another way to understand the Socratic method is to understand what it’s not. This can best be viewed in Socrates’s direct opposition and reaction to Sophism. Sophism was another method of teaching in Ancient Greece in which a handful of intellectuals taught general wisdom about human affairs, such as rhetoric and philosophy, to children of the wealthy. While early Sophists were well-respected, later Sophists came to be known as deceptive (due to their use of rhetoric) and elitist (since they reserved their teaching to only those who could afford it). Critics accused the Sophists of doling out opinions on specific subject matter as opposed to actually encouraging independent thinking.

The Socratic method, on the other hand, is a way of thinking that allows individuals to define their own purpose for learning and explore this purpose through open-minded questioning of what they hold to be true.

Entrepreneurs can find value in the Socratic method because they, too, are bombarded by assumptions based on what others and they themselves believe to be the best plan of action for pursuing a business idea.

Entrepreneurial learning, or the acquisition of knowledge necessary for creating a business venture, is built around the constant questioning and testing of these assumptions – theories about what we hold to be true – for validity. These assumptions can range from beliefs about what the market wants, where opportunities lie, to the effectiveness of a new product feature.

The Socratic Method and Entrepreneurial Learning.

The nature of the Socratic method is indefinite and, therefore, has countless interpretations and applications. In examining the Socratic principles outlined by Rob Reich, a Political Science professor at Stanford University, we observed that the principles he advocates for in the classroom translates to entrepreneurial learning. We applied Reich’s interpretation of the Socratic method to entrepreneurship and found valuable insights relevant to starting successful companies.

Here are two quick takeaway on what entrepreneurs can learn from Socrates.

1. The Socratic method provides focus through clarity of purpose.

Reich encourages his students to use the Socratic method “to examine [their] values, principles, and beliefs”. In essence, this approach demands that you as an entrepreneur answer the question, “Why are we here? Why do we exist as an organization?”

Founders who define values, goals, and concepts for their company set a clear direction for the organization. By constantly questioning our belief system, we reach clarity of purpose. Clarity of purpose leads to a shared sense of accountability, keeping team members on the same page and in pursuit of the exact same outcomes. Organizations, then, are able to fully maximize human capital when everyone’s desires are aligned and pointing to a shared vision of the future. Like running a race, it makes sense for a company to first define its starting line in order to work towards an intended finish line. Furthermore, given the myriad directions that outside forces (markets, investors, competitors) can pull an organization, the Socratic principles of self-inquiry can help you stay the course through the inevitable distractions.

When a company clearly defines and communicates its belief system, it attracts customers and employees who share similar beliefs about the world. Apple is the most obvious and universally recognizable example of a company who does this extremely well. Their rallying cry of “Think Different” engenders fanatical loyalty and support for the Apple brand.

2. Use the Socratic method to develop and reinforce an entrepreneurial mindset.

Reich states that the “Socratic method is better used to demonstrate complexity, difficulty, and uncertainty than at eliciting facts about the world”. Note the keywords: complexity, difficulty, uncertainty. These words paint a realistic picture of day-to-day life at the beginning of a venture, and in so doing present an opportunity to learn.

Most people view this set of words as negative. An entrepreneurial mindset involves interpreting complexity, difficulty, and uncertainty as an opportunity to test assumptions, run experiments, and create knowledge from these activities.

Entrepreneurs start testing assumptions by defining current beliefs based on past observations or intuition. They then ask themselves or are asked by outsiders (investors, mentors, etc.) questions that serve as the basis for setting up experiments. Whether in the form of interviewing customers, doing competitor analysis, or conducting A/B testing, experimentation essentially tests what entrepreneurs hold to be true against reality.

The Socratic principles of defining current beliefs, developing a question, and setting up experiments to discover new insights are the core building blocks of entrepreneurial learning. The Socratic method is a powerful, world-changing idea for a reason, and entrepreneurs, whether consciously or unconsciously, follow a Socratic path as they grow their ventures.

[1] Fast Company’s This is Generation Flux: Meet the Pioneers of the New (and Chaotic) Frontier of Business

[2] Learn NC’s Socratic method

[3] Stanford University Newsletter on Teaching’s The Socratic Method: What it is and How to Use it in the Classroom

Time-Capped Education: Why 3 Days are Better Than 3 Months for College Students.

Time-Capped Education: Why 3 Days are Better Than 3 Months for College Students.

The demand for entrepreneurship education is rapidly growing at universities with almost 90% of students now believing that entrepreneurial skills are “vitally important given the new economy”. [1] With the rise of campus incubators (like those at Duke, UCLA, and Syracuse) and private incubators (like Y Combinator and Techstars), the opportunities for students to pursue ventures while still in college are dramatically increasing.

There are a number of avenues to accelerate your entrepreneurial journey – classes, incubators, etc. There is a strong case to be made for short format entrepreneurship programs as the most effective choice for that journey. After running over 100 3DS programs on 5 continents, our experience shows that entrepreneurial learning happens best in 3 days versus 3 months for college students.

Here’s why.

Time constraints create focus.

Parkinson’s law states that “work expands so as to fill the time available for its completion.” For example, think about the last time you procrastinated a school assignment and maniacally cranked it out the night before. Fighting against the clock (aka clutch time) leads to a state of intense focus and efficiency.

The idea of time-capping projects is not new. Productivity hacks like the Pomodoro Technique advocate for 25 minutes of intense work output interspersed with break intervals. Goal-setting theories like the SMART criteria – making goals Specific, Measurable, Assignable, Realistic, and Time-related – also preach creating time-bound goals.

The email-marketing powerhouse, Mailchimp, is a great example of a company that manipulates time for productive sprinting. Ben Chestnut, CEO of Mailchimp, encourages his team to consistently crank out new products by having them work in cyclical 1-week stretches of intense focus. The success of Mailchimp stems from the company’s ability to harness one of the most effective creative forces out there: time.

In terms of building a company over the span of a weekend, knowing that your team only has 72 hours intensifies the process of ideation, marketing validation, prototyping, and so on. Not only does this intensity increase focused productivity, it also leads to a heightened level of execution in a simulated high-pressure startup environment.

Short form immersions empower students to move fast and break things…without fear of failure.

Let’s first talk about the importance of failure. Failing is a stigma that’s deeply ingrained in our cultural consciousness. Failure is seen as the polar opposite of success. Success and failure, however, are not dichotomous opposites but rather necessary complements. Failure is embedded in the process of creating something great since, at its core, failure is simply “trial-and-error learning.”

The key to successful failures is to fail quickly and with a purpose. First, failing early (and cheaply) allows teams to avoid the pitfall of escalating commitment – a tendency to keep throwing energy and time behind a failing course of action. Scrapping a bad product you built in two days is cognitively and emotionally easier than scrapping a bad product you’ve been working on for the past two months. Secondly, successful failures have end goals in mind. They disprove or validate assumptions in order to reiterate a product or plan of action.

For short burst formats like 3 Day Startup, students are given permission to fail. Since the level of expectations is different for a 3-day event versus a 3-month program, students can view the exercise as a safe space for entrepreneurial experimentation. The 3DS “laboratory” gives students permission to fail and fail quickly.

Students can commit for 3 days.

Lastly, university students are generally resource-crunched individuals when it comes to time and money. While entrepreneurs obviously have to make professional and personal sacrifices, it’s impractical to ask students to make a long-term commitment to a startup idea without some level of validation. It’s like getting married without a few first dates.

A three day immersion is a manageable short-term commitment that’s less intrusive on the life of a university student. Once startup ideas are validated and show promise, students should take it to the next level and apply for that incubator or accelerator program.

[1] Time’s How Entrepreneurship Can Fix Young America

I’ve Got 99 Problems But a Pitch Ain’t One: What Entrepreneurs Can Learn From Rap Music

Allow Me to Reintroduce Myself
Two years ago I presented at an investor conference and when I used the phrase “making it rain” the audience of VCs and angel investors returned only blank stares. Ever since, I’ve been interested in exploring and discussing the relationship between rap music and entrepreneurship. A month ago I delivered a keynote at Startup Week hosted at The University of Texas at Austin. This piece is an adaptation of that talk.

Rap music is one of the few genres that embraces business principles. When was the last time you heard an opera singer, jazz guitarist, or dubstep producer talk about the business of what they do in their art? Rappers, however, talk about this topic all the time.


There are a staggering number of commonalities between rap and startups. For example, the culture of “performance enhancing substances” is heavily referenced in both industries.


Lil Wayne with codeine cough syrup and 3 Day Startup Alum Sri Sonti (cofounder of Remark, a 500 Startups accelerator company) with energy drink

Another common thread is that the parental approval rate for kids wanting to pursue a career in rap music or entrepreneurship is still relatively low. This is the case because both endeavors still maintain a high failure rate: 90% of new businesses fail and the number of rappers that fail is probably even higher.

Given these commonalities, there are several insights that these industries can provide to one another. Here is what entrepreneurs can learn from rap music.

Get a Cofounder

Rapper Snoop Dogg and Producer Dr. Dre/Business cofounder Steve Jobs and technical cofounder Steve Wozniak

Left: Rapper Snoop Dogg and Producer Dr. Dre / Right: Business cofounder Steve Jobs and technical cofounder Steve Wozniak

Rap music and startups resemble each other at the earliest stages. Rap music starts with a rapper and a producer. The rapper provides the words, the voice, and handles the more public-facing activities. The producer (also called a beat maker) creates the tracks that the rapper raps over. Some of the biggest names in rap music today found their initial success due to their own in-house producers (see: Drake and 40, Kendrick Lamar and Ali). Often this person not only supplies beats, but helps architect the sound of a rapper’s signature style.

This duality is eerily familiar to the beginning stages of a startup. Two people — a business and a technical cofounder—represent the best foundation on which to build a new company. The tech cofounder usually builds the software that powers the product, and the business cofounder runs operations, fundraising, or other activities that are needed for the startup.

Aside from the obvious benefit of having a cofounder with a set of skills that complement your own, having another person with dedication and passion that equals yours increases the chances of capturing opportunities by way of identifying early employees, discovering initial investors, and more.

And attaining success in a startup is difficult. There are ups and down in the process.  Having someone to balance you out is of enormous value. Single founders often endure a lonely journey.

The best way to choose a cofounder is to collaborate on projects, in hackathons, or at programs like 3 Day Startup. This is the fastest way to see a potential cofounder in action and test them out so you can understand their work ethic, capabilities, communication style, and sensibilities. How do they lead a team? How strong is their execution ability? How are they in front of a crowd? Can they build what they claim they can build?

Fail Fast
The RZA is the leader of the Wu-tang Clan, the biggest and most successful collective in the history of rap music. He is known for a gruff rapping style, grimy beats, and an obsession with kung-fu films and asian mysticism. But he had to try a few times before he found the winning formula — or what the startup world might refer to as product/market fit. Signed to Tommy Boy records in 1991, he released his first single “Oh We Love You Rakeem” under the moniker “Prince Rakeem”. Prince Rakeem’s persona was that of a smooth talking loverman character. This record flopped and rap music fans paid it little mind. Undeterred, the RZA re-emerged a few months later with an altogether new project: he and his neighborhood crew reformed as the grimier, gloomier Wu-tang clan and released one of the greatest rap records ever.

Prince Rakeem vs. The RZA

Prince Rakeem vs. The RZA

Grammy award-winning rapper Common followed a similar path: his first release, under the name “Common Sense”, represented a thuggish portrayal of life at the bottom. This release failed to gain the reception he was looking for so he retooled and eventually ended up releasing more emotional, progressively-minded lyrics referred to in the rap industry as “conscious.”

Common vs. Common Sense

Common Sense vs. Common

Initial failures provide learning and feedback to eventually reach success. Just like the The RZA and Common, several of the most famous startups in the world experienced a bump in the road before they hit it big.

Paypal began as a mobile payments company and pivoted several times before realizing that the greatest customer need their product met involved handling transactions inside the Ebay platform. This was the first step upon which Paypal created their dominance of online payment processing. Twitter, originally known as “Odeo”, represents another notable example of the founders going back to the drawing board. Odeo provided directory and subscription services for podcasts before scratching that concept in favor of short-burst messaging. Finally, Instagram began as a complicated, feature-heavy geolocation app with a Swiss army-like array of features. User behavior indicated that photo-sharing resonated most with their users so they scrapped the excess features and honed in on what really excited their users.

Practice Rapid Prototyping and Customer Feedback
The rap industry follows an extremely effective product development cycle unlike any other genre. Rappers use mixtapes as de facto beta products. A rap “mixtape” is not a cassette — it is an unofficial album not fully refined and developed, usually given away for free online. The goal of releasing a mixtape is to generate awareness and receive feedback from the market before the release of a full-length record.

Aspiring rappers release mixtapes through various channels, allowing them to build a following and catch the ear of more established rappers who run their own labels. This process is know as “co-signing” — in the startup world this could be compared to partnerships.

In the early 2000s, Lil Wayne proclaimed that he was the greatest rapper alive and the rap world let out a collective laugh. Up to this point, Wayne was considered an afterthought in the cannon of rappers on the Cash Money record label and mostly known for being the weak link in the Louisiana supergroup the Hot Boyz, which featured more marketable rappers such as Juvenile and B.G.

But he kept cranking out music at a rapid pace, eventually releasing 14 mixtapes in the early 2000s.

Lil Wayne mixtapes

Lil Wayne mixtapes

With each release, Lil Wayne was refining his sound based on feedback from listeners before releasing an official album. This proved to be successful for him. When he released Tha Carter III in 2007, the album achieved double platinum status.

Share Ideas and Tools: A Tale of Two Apaches
Ecosystems and communities matter for a slew of reasons. Good ecosystems encourage sharing ideas and tools. Rap music is built upon samples, which borrows beats or small snippets from other songs. A “break” — short for break beat — is the part of the song where the instrumentals and vocals drop out and all you can hear is the drums. Kool Herc, the father of hip hop, had the idea to get two copies of the same record and play the break beats one after another, creating an uninterrupted beat over which rappers could rap. Others starting copying this technique, searching for and sharing popular breaks from records. Some of the most famous rap songs ever are built on some famous breaks.

The image below maps out popular songs that sample the Apache break:

Songs that sample the Apache break

Songs that use the Apache break

The way the rap community uses breaks is exactly how the startup community uses open source software. Open source software is software developed and shared by hobbyists, amateurs, and professionals.

Coincidentally, one of the most important pieces of open source software is the Apache web server. This software runs major infrastructural components of some of the biggest software companies in the world.

Companies using the Apache break

Companies using the Apache web server

Represent Your Local Community
Unlike other genres, rappers constantly remind you where they are from. The regionality of rap is one of its greatest strengths: region-specific genres such as the Bay Area’s hyphy, Texas’ chopped and screwed music, and traditionalist East Coast rap all have unique signatures that provide identity, character, energy, and relevance to each community.

Startup ecosystems have similar regional differences, and coincidentally, these three rap music hubs* represent three of the largest startup ecosystems. In the startup world, the Bay Area is known for innovative consumer-facing startups. Texas, specifically Austin, is known for profitable B2B software startups. New York City is known for media and content-focused companies.

Note: Atlanta is the current center of the rap music universe but the Atlanta startup scene, while impressive, does not map as cleanly into this analogy

Note: Atlanta is the current center of the rap music universe but the Atlanta startup scene, while impressive, does not map as cleanly into this analogy

Rap regionality is a big deal because it is empowering on a local level. Successful regional artists provide success stories to others from that community. Global names matter and they always will: Global rap superstar 50 Cent and Facebook founder Mark Zuckerberg are similar in this respect. Both of them represent huge successes. But both of them emerged from fairly predictable sources, i.e. locales where lots of successful rappers and startup founders are from, respectively (50 is from Queens and Zuckerberg went to Harvard).

Tech N9ne (Kansas City), Nipsey Hussle  (Compton), or E-40 (Bay area) may not be household names in popular music. But each of these artists is stylistically inseparable from their hometowns; they embody the idea that someone from their community can make it in the rap game.

Anyone who attended Harvard can look to Zuckerberg’s success as a motivator. But it can be more motivating to see a local entrepreneur having regional success. This is why Dan Graham’s Build-A-Sign is important to Austin and Brett Martin’s Castle Branch is important to Wilmington, NC — these companies may not be well-known outside of their regions but they are symbolic of the potential of their respective ecosystems.

It is an exciting time for both rap and startups. Both of these cultural forces have boomed in popularity over the last two decades: demand for rap music and entrepreneurship are at all-time highs. The change in tide for both indicates a change in attitude of the new millennia. The current generation of young people that are driving our culture and shaping our economic future resonate with the values inherent in both rap and startups: innovation, a healthy sense of risk, and the power of community.

How Alumni Can Support University Entrepreneurship Education

Entrepreneurship is currently a hot topic and many universities are looking to attract the best aspiring entrepreneurs by expanding course offerings and programs outside of the norm. Entrepreneur.com does a good job of summing up some of these trends in a relevant article.

Many university entrepreneurship programs are funded by endowments or donations from successful alumni. So as a successful alumnus, what can you do to support entrepreneurship education at your alma mater and ensure that your funds will be utilized effectively?

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Why the University is the Ideal Startup Platform


The entrepreneurial spirit at the university level is willing and eager: nearly 90 percent of young people believe that entrepreneurship education is important according to the Young Entrepreneur Council. And with the advent of the internet, free access to resources, and lowered barriers to entry, students can now start companies with minimal capital. At 3 Day Startup, we help students start companies through our experiential education entrepreneurship programs. Through our work with 5,000 students at 45 schools across the world, we’ve realized that the university is an ideal startup platform.

Ambitious and smart people

College is by no means a prerequisite for starting a successful company, but there are a number of factors that allow it to give rise to startups. The first reason is that on average, institutions of higher education tend to attract both ambitious and smart people. When Forbes profiled young disruptors, innovators, and entrepreneurs in their annual list of 30 under 30, the 14 of the top 15 individuals highlighted in each category attended or graduated from college. In fact, many of the men and women profiled on this list attended an Ivy League institution. (The list touched on 15 industries that ranged from Education to Tech and profiled in depth one individual in each category.)

This raises an inevitable question: Why was the university experience a part of their entrepreneurial journey?

One simple explanation may be that ambitious and smart people strive to attend the very best educational institutions should circumstances allow, displaying the discipline and work ethic that’s critical to achieving such levels of future success when launching an early stage startup.

My Visit to Daejeon, South Korea: KAIST, Chul Hwan Kim, Mentors, and Growing an Entrepreneurial Ecosystem

Korea_Advanced_Institute_of_Science_and_Technology_logoThe Korea Advanced Institute of Science and Technology (KAIST) is the premiere science and technology academy in Korea. KAIST’s primary campus is in Daejeon and the location of an impressive research and science park one hour south of Seoul.

Seok-bong Lee is the head of DaeDeok Net, the foremost voice of the innovation and technology emerging from the Daejeon community. He invited me to speak with some of the leaders in this community so I jumped on a train and headed south to Daejeon two days after my talk at the STEPI Symposium. The day kicked off with a fantastic lunch including duck, fish, kimchi, and iced coffee. I had the honor of meeting Chul Hwan Kim, (Chief Director, KITE Entrepreneurship Foundation), Se-Jung Oh (President, Institute for Basic Science), Dr. Jooho Whang (President, Korea Institute of Energy Research), and several other faculty members and administrators.

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Korea and the Creative Economy Initiative: Shifting Towards an Entrepreneurial Culture at the 2013 STEPI Symposium

I had the honor of speaking at Korea’s Science and Technology Policy Institute (STEPI) 2013 International Symposium in Seoul last week. STEPI, a think tank led by Dr. Jong Guk Song, orchestrated this conference to address the new administration’s bold new vision for Korea’s future: the creative economy. Other speakers at this conference shared thoughts on new models of government-funded entrepreneurship and exciting new areas for growth in non-traditional sectors (e.g, space and deep sea exploration). My talk focused on entrepreneurship education models and recommendations for how Korea can maximize the number of startups emerging from universities. This post will share some of these experiences.  

From a Western perspective, the story relayed by Doug Yeum, head of Google Korea, was remarkable. Doug told us about how a friend of his in Seoul left the startup world to pursue a job with a large corporation because he thought it was needed in order for him to find a woman that would marry him. He acted on the cultural belief that if a woman couldn’t recognize the logo on his business card, she wouldn’t recognize him as a viable candidate for marriage.

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