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Assignment – Entrepreneurship Journal and Self Assessment

You will keep a journal for the duration of this course. You will make entries in the week following each of the weekends in which we meet. The journal is for you. However, to maximize the learning across students in the course, you will post one reflection from your journal in the weekly discussion forum (for MGMT801 this is set up in Canvas) and then comment on one post of a classmate.

For the journal:

You will probably want to set up a Google drive folder (or equivalent cloud repository) for your work products for this course, including the journal.

The journal can be just free form text (e.g., a Google Doc). The journal is for you. You will submit a PDF of the entire thing at the end of the course just so we can give you credit for the work you are doing for the course. (You may redact any portion of the journal that you don’t want the TA and instructor to see.) You are completely unconstrained as to what is in the journal, but its contents will likely be primarily about you as a person in the context of entrepreneurship: How you feel about the possibility of being an entrepreneur. What roles you might want to assume in a new venture. What problem areas you’re excited about.

For the discussion forum:

Extract one reflection from your journal and post it to the discussion. It probably makes sense to keep these posts to a paragraph or two, say 100-300 words. If you are stuck about a topic to reflect on, just pick the podcast, film, or book you enjoyed most recently and offer some reaction to it.

In addition to posting a reflection of your own, please respond to the post of a classmate. Your response can be to any post from any week.

First Journal Entry – Self Assessment

Create an entry in your Entrepreneurship Journal entitled self assessment and put a date on it. You’ll probably be interested in returning to this entry periodically in the coming months and years.

Here are the prompts for the self assessment. (Note: some of these questions come from an article in the First Round Review about co-founders.) These are not structured as a survey scale or anything, but rather just questions that reveal your feelings about some of the key personal issues associated with being an entrepreneur. You do not need to answer all the questions. You should answer the ones that really force you to think.

What Do You Bring to the Venture?
[Either for the focal venture for this course, or for a hypothetical TBD opportunity]

  • What are your strengths and superpowers?
  • What are your weaknesses? How do you compensate for them?
  • What would you want your role to be before the venture reaches product/market fit? What would you want your role to be after the venture reaches product/market fit? How do you see your role changing as the company starts to scale? 
  • If the CEO/Founder role becomes unavailable entirely (e.g. the board hires a professional CEO or an experienced executive), what would you want your new role to be?

Rate your competence in these areas (both as an individual contributor, and as a leader) on a scale of 1-10. Then rate your passion for each on that same scale.

  • Sales
  • Marketing
  • Product
  • Design (graphic, UI/UX, industrial design)
  • Engineering
  • Operations
  • Fundraising
  • Leadership
  • Company Building (e.g., organizing and scaling functions and systems)
  • Recruiting
  • Legal
  • Domain expertise (e.g., healthcare, data science – please specify)

Vision of Future

  • What are some examples of companies that represent aspirational outcomes for you?
  • What does the exit or end game look like for you? (e.g., “becomes my job and life,” “create value in 3-5 years and sell,” “invest 7-10 years to grow a big company and IPO”)
  • How do you think about the timeframe and pace of success? Are you willing to take the longer path? How long is too long?

Personal Motivation – Purpose, Fun, and Money

  • Why do you want to start a company — in general, and in particular right now? [or if you don’t want to start a company, why not?]
  • What is success to you? What motivates you personally? 
  • What impact do you want to have? Is your startup objective “getting rich” or “changing the world”? 
  • Is control or financial success more important? (i.e. Are you willing to step aside if the company is more likely to have a financially successful outcome or is it important for the founders to stay in control of the company’s destiny?)
  • What would you want your personal financial outcome to be at exit? What’s the number?

Financial Security

  • How anxious are you about the prospect of quitting your job and working full-time on starting a venture, with the prospect of not getting a paycheck for 6-12 months?
  • What is your personal runway? Current burn rate? Would you invest your own money (likely retaining higher equity in return)?
  • What is the minimum monthly salary you need to survive in normal times? To be comfortable? To feel like you’ve “made it?”

Commitment [may not be relevant if you aren’t committed yet.]

  • Will this company be your primary activity? Do you have any other time commitments?
  • What is your expected time commitment right now? How do you see that changing in the next 6 months? 2 years?
  • How many hours/week are you willing to work? For how long? What sounds good? What sounds like hell? Do you have different expectations for different phases of the company’s lifespan (i.e. willing to work harder in the beginning)?
  • Do you feel it is possible for you to build a wildly successful company without burning out or damaging other parts of your life (family, health, etc.)? 


Gloria Lin. First Round Review. The Process I Used to Find my Co-Founder

The Triple-Diamond Model of Design

I’ve been a product designer my entire adult life. Here is one of the products I created, the Belle-V ice cream scoop. In full disclosure, I had a lot of help from a talented team. When people see the product they impute genius to the designer – wow, that’s amazing. How did you come up with that?

I’m using an example of a physical good for specificity, but I’ve experienced the same kind of reaction to digital products and services.

The reality is that I learned an effective process when I was in my 20s and I’ve applied that process repeatedly, sometimes weekly or even daily for 40 years. When you only observe the outcome, the results seem magical. But, the truth is that a fairly straightforward sequence of process steps can reliably lead you to a great result.

Design is just another word for the pull approach to innovation. All design processes are a sequence of steps that begin with some articulation of the “what” and result in some description of the “how” – the process moves from what to how.

Commercial phase-gate product development processes are just an elaboration of that basic idea, with lots of detail. My textbook on product design and development (Ulrich et al. 2020) is a comprehensive description of that detail. Most of you working in larger organizations probably use some sort of phase-gate process that is specific to your industry.

But, here I’m going to abstract a bit, and focus on the elemental design process – what is design at its very core. While design is the core problem solving approach within the product development process, design can be applied beyond product development. It’s almost a building block of being human – of dealing with life.

My goal is to describe the design process in a way that it can be used in myriad situations, from the creation of a new product from scratch, to the improvement of an existing product, and even for solving internal innovation challenges such as finding new ways to reduce waiting times in emergency departments.

To reiterate, the standard phase-gate product development process is a fully elaborated methodology that typically includes the roles of different functions within the organization. It emphasizes not only what to do in each phase, but the notion of a gate that must be cleared in order to proceed to the next phase. I am now going to boil that basic process down to its essence to give you a tool I call the triple-diamond model that can be used not just in zero-to-one product development, but also in almost any other problem solving situation.

To give credit where credit is due, the triple-diamond model is my extension and elaboration of the Double Diamond Model articulated by the UK-based Design Council, a non-profit organization with the mission of improving design practices.

The three diamonds correspond to three steps. 

  1. Clarify the job to be done in a jobs analysis
  2. Understand the needs of the customer or user. 
  3. Create a great solution concept.

In practice, a fourth phase is usually important – implementing that concept in a way that the organization can actually deliver the solution. This involves writing the code, designing the parts, and planning for production.

The three diamonds each represent a cycle of divergent and convergent thinking. For each diamond, the designer explores alternatives, and then focuses.

The first diamond answers the question, “What is the job to be done?” It starts with a target customer and the gap or pain point as you have first sensed it, and it results in a carefully considered reframing of the design problem in terms of a job to be done. In fact, one of the critical elements of an effective design process is not even really problem solving so much as problem definition.

The second diamond begins with a job to be done and develops a comprehensive understanding of the customer needs, which are those aspects of a solution that could result in satisfaction and even delight if satisfied. The convergent portion of the second diamond identifies one or a few insights, which are essentially important customer needs that were previously not known.

The third diamond uses those customer insights to pull many possible solution concepts and then selects one or a few for further refinement and testing.

Let me show you how the three diamonds played out for the Belle-V scoop. I started with a vague sense that ice cream was really hard to scoop. In diamond 1, I focused on the at-home consumer of ice cream and came up with the job to be done “How might we better dispense bulk ice cream into individual portions?” In the second diamond, I observed people scooping ice cream and noticed that the wrist angle was quite awkward, even painful for some people. That insight allowed me to pull several different solution concepts, including the one that eventually was embodied in the product, a more or less conventional scoop, but with the scoop angled relative to the handle.

Of course, really, it’s diamonds all the way down. The triple diamond model focuses on the concept development process, but when the team proceeds to build the product based around a concept, it will almost certainly use additional cycles of divergent and convergent techniques in order to solve downstream problems, say for establishing a product architecture, or implementing specific components of the solution. For example, even after we had converged on the solution concept of an angled scoop, we did a huge amount of exploration to find the final form of the object. Another diamond focused on the detailed design of the shape of the scoop and handle. And for that matter, there was another diamond when we considered the surface finish of the scoop – divergent exploration of alternatives and then convergence on tri-valent chrome plating.

Some of you are thinking that this model seems pretty tidy for a very simple piece of hardware like an ice cream scoop, but may not apply to more complex goods and services, say to enterprise software or to a hotel experience. I have a couple of reactions to those reasonable thoughts. 

First, as an aside, there’s a reason they call it HARD-ware – it’s hard. Even a simple object like an ice cream scoop presents a lot of complexity and challenges when it comes to actually getting it to the marketplace. 

But, more substantively, for new, zero-to-one systems, software, or services, you must still devise an overarching solution concept. For example, consider LinkedIn – the top-level solution is essentially a user-created resume-like profile with the ability to establish a connection between two individuals, and then the ability to search 1st, 2nd, and 3rd order connections in the resulting professional network. Such an overarching concept could be developed with the triple diamond model. 

For established systems, the triple diamond will be unlikely to be applied to the entire product or suite of products, but rather more likely to a feature within that more complex product. For example, once LinkedIn had become a successful product, the triple diamond model could still be applied, but to a new feature, say the creation of the follower feature, which allows individuals to follow another person and get updates that person publishes, but without requiring the individual to become a bi-lateral connection.

Problem Solving, Design, and Design Thinking

I happened to be on a holiday ski trip when I was preparing for this video. (I know, that doesn’t sound like that much of a holiday.) I kept thinking to myself, skiing is fun, but it’s a huge annoyance to actually get on the slopes. For most novice skiers, you have to procure skis, boots, poles, helmet, goggles, and warm clothing. Then, you have to put all that stuff on. Then, while fully dressed in really warm gear you have to walk awkwardly from transportation to a ski lift, sometimes navigating a flight of stairs. Then, you put on the skis. By then you are sweating and your goggles are fogged up. Next you wait in a line. Then you get on a windy and cold ski lift and become quite chilled. When you finally get to the top of the mountain, you stare at a map trying to figure out the best route down. Finally, you get to slide on the snow, which is actually quite fun. I’m an incurable innovator and so I found myself posing the question, “How might we improve the experience of getting skiers onto the slopes?”

If I were a trendy corporate consultant, I would call this a “design thinking” problem. But, I’m actually a bit of a crusty old designer. I’ve taught design for more than 30 years. So, I have to ask “what exactly is design thinking” and how is it any different from plain old design?

Well, first let’s first go back to the definition of innovation and design.

I define innovation as a new match between a solution and a need. Innovation can result from a push – starting with the solution and looking for a need. For example, what might we use the blockchain for? Or, it could start with the need and pull the solution, like I framed the skiing challenge. “How might we improve the skier experience?” Design is innovation anytime you are pulling a solution from a need.

So considering our definition, the short answer to what is design thinking is that it is design. Really. You apply the same process to creating a better ski experience as you do to creating a better ice cream scoop, or a better fitness app. In fact, the word design thinking annoys a lot of designers, because they are usually less interested in thinking about problems than in actually solving them. 

Once I cool off a bit about the weird term “design thinking,” I realize there may be a gem of an idea in there, and that a bit of nuance may in fact be warranted.

A useful definition of design thinking might be that it is design of things we don’t normally think of as designed.

For example, here are some problems for which the design process could be used, resulting in solutions that would not normally be thought of as designed artifacts.

  • How might we improve the patient experience in the emergency department at our hospital?
  • How might we improve the convenience of using a bicycle for transportation?
  • How might we create a delightful food delivery service?

A lot of people talk about needing to apply more design thinking in business. I find myself wondering if the desire for design thinking is really just a reaction to the use of too many spreadsheets and PowerPoint presentations, disconnected from customers and from exploration of solution concepts. This reaction reflects a desire for a different and better culture of innovation.

I do think that good designers exhibit a few desirable elements of culture. Interestingly, most of these elements don’t need to really be confined to design. Here are five:

  1. Designers exhibit a bias for action.
  2. Designers tend to be optimists, exhibiting a culture of yes.
  3. Designers tend to use exploratory prototypes early in the problem solving process.
  4. Designers tend to be skilled at visual expression.
  5. Designers tend to use empathic methods for understanding customers.

Despite my enthusiasm for all things design, I won’t argue it is universally the best approach to problem solving. For example, it would be a mistake to abandon elements of Six Sigma, Total Quality Management, the Toyota Production System, and data-based approaches. It would also be a bad idea to use a design process to find the volume of a geometric shape, a task better suited to an algorithm.

But, for a huge set of challenging problems, design is a great approach. It is fundamentally divergent and open-ended in its perspective on addressing user needs, and that’s useful whether you are designing a bridge, enterprise software, or an insurance claims process.


Karl T. Ulrich, Steven E. Eppinger, and Maria C. Yang. 2020. Product Design and Development. McGraw-Hill. New York.

Double Diamond Model. UK Design Council.

Opportunity Identification

I’ve written a lot about opportunity identification in my books Product Design and Development, Innovation Tournaments, and The Innovation Tournament Handbook. The topic is also covered fairly extensively in the course OIDD 614 Innovation Management. Consider this chapter a quick summary of the big ideas in the context of identifying entrepreneurial opportunities.

Often the Opportunity Finds You

On my weekly podcast I have interviewed about 500 founders. For about half of these founders, the opportunity found them; they did not go looking for an opportunity. For example, consider Flava Naturals, founded by Alan Frost. Here is how he describes the origin story.

“I told you we should eat more chocolate!” I looked up from my coffee and there was my wife holding out the New York Times, and looking very happy. She’d just read an article about a Columbia University study that linked chocolate to enhanced memory. (…) But I was a biotech exec accustomed to how the media could exaggerate the importance of findings in small studies. I love chocolate too, but was skeptical, to say the least. So I dug deeper. Sure enough I found dozens of placebo-controlled studies that demonstrated meaningful benefits of cocoa flavanols on brain, heart and skin function. There was a catch though, and a pretty big one. The best results seemed to require consumption of 500-1,000mg of cocoa flavanols a day — that’s 5-10 average dark chocolate bars! (…) So began my quest to develop a decadent chocolate with the naturally preserved flavanols proven so healthy. And a business was born.”

Alan Frost, Founder and CEO Flava Naturals

Another common pattern is that entrepreneurs experience a pain point themselves and then set out to create a solution to address their own needs, and hopefully those of a larger market. Tammy Sun founded Carrot fertility services when she found that her employer did not cover fertility benefits as part of her health insurance, and that there were no enterprise solutions for managing fertility services for employees. She then set out to found a company to meet that need.

A third pattern, probably least common, is that an individual or team seeks out an entrepreneurial opportunity but has no particular problem area in mind. For example, Alan Cook founded, grew, and sold a first business in the pet care space, an opportunity born out of frustration with conventional litter boxes for cats. After a brief sabbatical, he sought to start another company, but this time was agnostic about the specific problem area. With the help of members of his previous team, he generated and considered about one hundred distinct opportunities, from pre-packaged spices to reconfigurable furniture, before focusing on another pet care product, this time for dogs. He pursued that opportunity not because he experienced a need himself — Alan doesn’t even have pets — but rather because he felt his prior experience gave him an unfair advantage, always a good thing for an entrepreneur.

A Personal Innovation Tournament

If you are motivated primarily by purpose, then the opportunity obviously matters a lot — after all you are setting out to do something specific in society. In that case, the entrepreneurial opportunity had better be aligned with that purpose. However if your goal is fun or financial return, does the selection of opportunity even matter very much? Put another way, is there not an opportunity to be financially successful or to have fun in pretty much any area of the economy? Sure, to some extent, you as an entrepreneur can probably find a viable opportunity almost anywhere you look. However, you will likely spend at least five years of your life pursuing a new venture. You might as well be quite deliberate about which opportunity you pursue. In my opinion, a good rule of thumb is that when considering taking the entrepreneurial leap, you should generate and evaluate at least ten different opportunities. 

The process of identifying or generating a large set of opportunities and then selecting one or a few to pursue further is an innovation tournament. This tournament need not involve a large group of people. In fact, you can run that tournament by yourself.

There are two parts to an innovation tournament — (a) generating the initial candidates and (b) selecting the exceptional few. Let’s start with the end in mind and consider selection criteria. Then, I’ll give some guidelines for generating opportunities.

Selection Criteria

The motives and selection criteria for a new venture depend on you and your co-founders, if any. You might want to do something in Brazil or be involved in the skiing industry. Make a list. Be very specific about the desirable attributes of your future business. This list is usually quite personal. For instance, when I started MakerStock, one of my selection criteria for this new business — after having made and sold scooters for 20 years — was that our product would not be intrinsically dangerous, as are wheeled vehicles. In my old age I prefer not to think about customers getting injured with my product. You will have your own set of hopes, fears, and desires.

In addition to any idiosyncratic preferences you may feel, the following questions are always important:

  1. Would you be excited, passionate, and proud to tell others, including your family, what your venture does?
  2. Is there enough TAM that you can create an enterprise of significant value? (See the chapter on market sizing.)
  3. Do you have a credible thesis for how you might offer value relative to existing companies (e.g., superior solution, strong brand, network effect)? (See the chapter on alpha assets and sustainable advantage.)
  4. Are your skills, credentials, and/or prior experience particularly relevant to success?
  5. How much capital will be required to pursue this opportunity? Is this capital requirement aligned with your vision for the type of business you hope to create, say a closely held lifestyle business versus a venture-backed company that goes public?

After considering these questions and your personal preferences, explicitly articulate your selection criteria so you can use them to evaluate the opportunities you are considering.

Here is a template (as a Google sheet) to use in evaluating opportunities.

Guidelines for Generating Opportunities

The process of generating opportunities usually plays out over weeks, months, or even years. Start a list. Accumulate ideas as they arise from whatever source. In addition to passive accumulation of ideas, you’ll benefit from focused, deliberate efforts to generate opportunities. Here are some guidelines, techniques, and heuristics for generating more and better ideas.

Push versus pull. Two distinct approaches to innovation are push and pull. With push, you start with a solution — say blockchain technology — and go looking for a market need. With pull, you start with a pain point experienced by consumers or businesses and you devise a solution. As a general rule you should take the pull approach. Identify a problem that potential customers have and then develop a solution that solves it better than existing options. The push approach can work on occasion, say when you start with a fundamental innovation in materials science that has the potential to be broadly useful. However, the push approach has proven to be much more risky than when you start with a pain point that is clear and obvious.

Second-best ideas. Learn from other entrepreneurs and ask them for ideas. Most successful entrepreneurs have dozens of ideas. They are working on their best idea, but you should ask them what is their second-best idea. Many will happily give you ideas and maybe even help you get started. 

Imitate but better. find successful ventures in a field that interests you and improve on their offerings by adding new features or benefits, reducing costs or risks, targeting new segments or markets or creating a unique brand identity. Hundreds of interestiong new ventures are listed by AngelList, WeFunder, StartEngine. YCombinator. Crunchbase, and other organizations. Existing start-ups are a treasure trove of information on what has been tried, what is working, and what approaches have failed. You will not usually want to go head to head with an exact replica of an existing company for two reasons. First, differentiation is a good thing allowing multiple companies to flourish by serving different segments. Second, there’s no particular reason to believe a start-up a few months ahead of you has taken the best approach.

Scour social media. Use social media platforms like Reddit, Quora, and Twitter to find out what customers are talking about, what problems they have and what solutions they are looking for. Monitor trends, hashtags, influencers and feedback. Journalists, bloggers, and conference organizers are in the business of sensing. While their insights are available to everyone, not everyone is viewing those insights through an entrepreneurial lens.

Careful of gold rushes. On-line forums and media outlets will occasionally exhibit fad-like behavior and herding. For instance, as I write this, these forums are crowded with excitement about large language models, chat bots, and artificial intelligence. Unquestionably opportunities abound. However, you can not typically observe the number of rivals entering a new market, and some markets are gold rushes, with too much competition. You may be better served by a quieter niche.

Import from another geographic region. Innovations are often geographically isolated, particularly if introduced by smaller firms. You can sense opportunities by identifying outstanding products or services in a distant region and then considering how you might adapt them to a different place.Translating the innovation from one geographic region to another can be a source of innovation.  

Consider lead user innovation. identify users who have a high need for your product or service and are ahead of the market in terms of innovation. Observe how they use your product or service and what modifications they make to it. Incorporate their feedback and suggestions into your product development.Firms have ample incentive to innovate. Innovation, after all, can result in new sources of cash. But lead users and independent inventors may have even greater incentives. Lead users are people or firms that have advanced needs for products or services that are not being met by other companies. They must either tolerate their unmet needs or innovate themselves to address them.

Poke around universities. Major research universities are wellsprings of opportunities and have produced such successes as Google (Stanford), Genzyme (MIT) and many others. Some of the opportunities spring from faculty-led research, particularly in the life sciences. Others are created by the legions of bright young students who enroll to chart new directions in their lives and careers.

Learn from Others

Here are several interviews I’ve done with founders that have particularly interesting origin stories. Sample the ones that interest you. Most interviews are about 25 minutes long and the origin story is usually in the first third of the interview.

Coravin (Greg Lambrect) – wine dispensing

Eat Just (Josh Tetrick) – alternative protein

Rebellyous Foods (Christie Legally) – alternative protein

Frutero (Mike Weber and Vedant Saboo) – ice cream

Flava Naturals (Alan Frost) – nutraceuticals

Carrot (Tammy Sun) – fertility services

The Infatuation (Chris Stang and Andrew Steinthal) – restaurant guide


Ulrich, Eppinger, Wang. Product Design and Development. Chapter “Opportunity Identification.” 2020. McGraw-Hill.

Terwiesch and Ulrich. Innovation Tournaments. Chapter Opportunity Identification. Harvard Business Press. 2009.

Terwiesch and Ulrich. The Innovation Tournament Handbook. 2023. Wharton School Publishing.

Introduction to Entrepreneurship

It’s more fun to be a pirate than to join the navy.

Steve Jobs

What is Entrepreneurship?

Entrepreneurship is the creation of a new economic entity to do a job in society.

The hallmarks of entrepreneurship include a focus on solving a problem, creative exploration of solutions, experimentation to reduce uncertainty, formation and operation of a new organization, and dynamic planning based on new information. Skills in these areas are valuable not just in starting a new company, but in addressing new problems in existing organizations. Thus, many but not all of the elements of this handbook are relevant to those engaged in innovation within established enterprises.

Founder Motives

Kerr and colleagues (2018) provide a comprehensive review of the academic literature on founder motives. (See “Notes” at the end of each chapter for links to references.) You can read that paper if you want to go deep. But, if not, here’s the TLDR. Founders are usually motivated by multiple factors to start businesses. These motives can be usefully divided into three broad categories: purpose, fun, and money.


Uma Valeti, a cardiologist by training, and founder of Upside Foods (formerly Memphis Meats), told me that he started the company because he wanted to detach slaughter from meat production. He recalled a birthday party he attended as a child in India in which there was a party celebrating life in front of the house, while others were killing an animal in back of the house. That event made a deep impression on him. Many years later when he worked on the technologies for growing human heart tissue in a medical context he recognized that his knowledge could be applied to another purpose in which he believed deeply. To pursue that purpose, he founded Upside.

Listen to some founder stories. A significant fraction will include phrases like “I had to do it” or “If I didn’t do it, who would?” or “I felt the world really needed this solution.” These are all expressions of purpose — a motive to create something new in order to provide a solution to a personally important problem to the world.


Steve Jobs said, “it’s more fun to be a pirate than to join the Navy.” That was certainly true for Jobs, but maybe not for you.

Some distinctive characteristics of the daily experience of being an entrepreneur include:

  • Nearly complete autonomy (as long as you don’t run out of cash).
  • Highly diverse tasks (from shopping for insurance to designing a user interface).
  • Privilege of working with a small tight-knit team, largely of your own choosing.
  • Ability to see immediate results of your work.
  • Creating something from nothing, whether a product or a company culture.
  • Continual opportunities to learn something new.
  • Complete absence of boredom.

For me, these attributes are mostly positive, and my own skills and capabilities are pretty well suited for these aspects of entrepreneurship. Entrepreneurship also comes with some characteristics experienced as negative by some people:

  • The complete absence of boredom may be experienced as unrelenting and intense demands on attention.
  • Significant stress about possibility of running out of cash.
  • May be a solitary effort, especially initially.
  • Requirement to do what needs to be done, sometimes including packing boxes or cleaning the office, without an ability to delegate to competent corporate employees.

On balance, most entrepreneurs seem to find the daily work of entrepreneurship fun, and preferable to working within an established enterprise owned by someone else. For some entrepreneurs, the adrenaline and satisfaction from the daily work of entrepreneurship is the most important motive for their career choice. For me, entrepreneurship has been personally demanding. I am extremely thankful to have been a full-time CEO when I was 39-43 years old. I’ve enjoyed being a part-time co-founder many other times. I’ve also been a business owner with ultimate responsibility for an established business for twenty years, but that has a very different stress profile from starting something from nothing. I do not need to have the experience of full-time founder and CEO again, and can get just the right level of fun without a lot of stress from being an investor and advisor.


The mean financial outcome for a capable and educated entrepreneur is likely a bit higher than for those who work in corporate jobs. However, the mean value masks a huge amount of variation. The modal and median outcome predicts that you will fail to realize significant value and would have been better off financially if you had kept your job instead of becoming a founder. Large financial payoffs are realized by a small fraction of entrepreneurs. In approximate terms, about 25 percent will do better than break even financially relative to staying on a traditional career path. About 5 percent of founders with your skills and capabilities will become reasonably wealthy (say USD 5-10mm after-tax pay out), and 1-2 percent will become downright rich (say USD 20mm+ after-tax pay out). For most people, the only way to have a decent chance at becoming wealthy in life (other than being born into it) is to start a business. But, it’s just a decent chance, say 10 percent or so, depending on your definition of wealthy. The probability distribution is also quite different for different types of ventures (more on that below). On the other hand, for most of you, the down side is not that bad. You had an amazing adventure. Worst case you gave up (a) savings worth a year or so of living expenses and (b) the opportunity cost of not having earned a market-rate salary for the years your business struggled. Then you went back to a regular job and did just fine. (See Botelho and Chang; and Amornsiripanitch et al. for a more comprehensive exploration of the implications founders returning to corporate jobs.)

I don’t have a large enough sample for statistical validity, but of the 100 or so Wharton alumni entrepreneurs I have followed closely or invested in, 100 percent live comfortable lives, take vacations, and send kids to college. Five-ish are what most would consider rich (e.g., USD 100mm+). Ten-ish are pretty wealthy as a result of entrepreneurship. Twenty-ish did just fine – let’s say better than having taken a corporate job. The other 65 percent would likely have been better off financially if they had devoted the attention they gave to their venture to a corporate job, and many of those are back working at such jobs.

If you really want to dig into the details on financial outcomes, the Angel List data is probably the best. An index of the available data is here:

You can find the data on venture returns here, from which you can impute a probability of a successful financial outcome.

Angel List has also integrated its experience into a white paper here: 

Types of Ventures

Not all ventures assume the same level of risk and uncertainty.

Read this article from Outside Magazine about Steve Despain (or listen to the Audm version of the story linked in the article). Steve is the founder of Firebox Stoves, a small business tightly coupled to his personal passions and lifestyle. What motivates Steve? How attractive is the Firebox Stoves business to you? (Here, I’m not necessarily asking you about your passion for the outdoors…but about owning and running a small business aligned with your passions.)

Now consider Blake Scholl (founder of Boom Supersonic). Here is an interview I did with Blake when he had just recently founded his company.

What motivates Blake? What does the financial payoff probability distribution look like for Blake vs. Steve? To make this concrete, what is the probability of a zero outcome for each? What is the probability of USD 100mm outcome for each? Estimate some probabilities in the middle, say USD 1 mm and USD 10 mm.

Rich or King?

A key dilemma most founders make is to be rich or to be king. (See Wasserman for a full elaboration of the dilemma.) The skills and capabilities required to lead a large, successful organization are quite different from those required to kick start a new venture. Some founders, such as Bill Gates, Mark Zuckerberg, and Jeff Bezos, did just fine in making the required transition. More typically, a founder faces a dilemma. Do I prefer to retain full control and manage my own kingdom, even if small, or would I prefer to step aside if necessary to ensure a huge financial outcome for investors, including me. Founders do not have to make this decision on day one, but still benefit from thinking through their preferences in advance. A self assessment of your skills and capabilities, and your relative preference for financial success versus control, should influence the type of venture you start.

Founder Characteristics

Founders are not typically kids. The mean age of founders of the fastest growing 0.1 percent of companies is 45. (See Jones, KIm, and Miranda.)

Founders do not require particular personality traits. No personality trait is predictive of success in entrepreneurship specifically, although the “big five” trait conscientiousness does predict career success more generally. (See Kerr, Kerr, and Xu.)

As long as you are not allergic to risk and uncertainty, your personality profile (e.g., introversion, agreeableness or lack thereof) probably does not disqualify you from entrepreneurship.

How do Founders Spend Their Time?

Every founder and every start-up is unique. Still, looking at the experiences of other founders can be instructive. Here is an unusually detailed analysis of how one founder spent his time in the first two years of his start-up.

Entrepreneurial Narratives

Entrepreneurs often follow the hero’s journey and so their stories can be compelling. Take some time to immerse yourself in some entrepreneurial journeys. Select from the following options.


  • Chip Wars. (This is a fantastic and comprehensive history of Silicon Valley and the semiconductor industry. This book will teach you about entrepreneurship, technological innovation, competitive advantage, and geopolitics.)
  • Shoe Dog. (If you can’t stand to go deep on semiconductors, try running shoes.)
  • Let my People Go Surfing. (Memoir by Yvon Chounaird, founder of Patagonia, and a pioneer in corporate responsibility.)
  • The Wright Brothers. (Fantastically interesting book, at least to me.)
  • Truck Full of Money. (Entrepreneurs can be quirky. Paul English, founder of Kayak, is the subject of a fascinating book that goes deep on character. If you like this one, then make sure to read Mountains Upon Mountains, Kidder’s biography of Paul Farmer, founder of Partners in Health – a social venture.)


  • General Magic (film) – This is the basis of a case discussion in my course on Product Management (Wharton OIDD654), so you might wait on this one if you plan to take that course.
  • Print the Legend (film) – about the formation and growth phase of Makerbot, the 3D printing company.
  • (Docudrama just for fun.) The Entrepreneur – The story of Ray Croc, who built the modern McDonald’s corporation.

I know these films and books mostly feature white American males. (Chip Wars does feature Morris Chang, a Chinese-American entrepreneur, and includes mention of the remarkable contributions to the semiconductor industry of Lynn Conway, whose personal story as a transgender female is incredible.) If you have some suggestions for more diverse stories, please send them to me.


Interview of Uma Valeti, founder of Memphis Meats (now Upside Foods). by Karl T. Ulrich. SiriusXM Launchpad. February 28, 2017.

Mollick, Ethan. The Unicorn’s Shadow: Combating the Dangerous Myths that Hold Back Startups, Founders, and Investors. University of Pennsylvania Press, 2020.

Jones, Kim, and Miranda.

Wasserman, Noam. The founder’s dilemmas: Anticipating and avoiding the pitfalls that can sink a startup. Princeton University Press, 2012.

Tristan L. Botelho, Melody Chang (2022) The Evaluation of Founder Failure and Success by Hiring Firms: A Field Experiment. Organization Science 34(1):484-508.

Amornsiripanitch, Natee and Gompers, Paul and Hu, George and Levinson, Will and Mukharlyamov, Vladimir, “Failing Just Fine: Assessing Careers of Venture Capital-backed Entrepreneurs Via a Non-Wage Measure,” National Bureau of Economic Research Working Paper, No. 30179, June 2022. (Summarized by Harvard Business Review here )

Azoulay, Pierre and Jones, Benjamin F. and Kim, J. Daniel and Miranda, Javier, Age and High-Growth Entrepreneurship (April 2018). NBER Working Paper No. w24489, Available at SSRN: 

Kerr, Sari Pekkala, William R. Kerr, and Tina Xu. “Personality Traits of Entrepreneurs: A Review of Recent Literature.” Foundations and Trends in Entrepreneurship 14, no. 3 (July 2018): 279–356.

Angel List Power Law paper