Think back to when you were in high school. How did you do your hair? How did you dress? People generally develop a sense of personal fashion over the ensuing years into adulthood, after a few flings with different styles — and hopefully, some honest feedback from friends and family.

But Susan Koger, co-founder of the independent online retailer of women’s fashion known as ModCloth, says it’s perfectly “OK to look back and cringe.” She wasn’t talking about day-glow tops and friendship bracelets, though. She was speaking at the Entrepreneurial Thought Leaders (ETL) Seminar series, sharing advice on pursuing one’s passion, with students on the cusp of launching their own careers.

Her point: Your first attempt at anything new will likely be crude, and so you should give yourself the permission to just do it. If you stick with it and get better, yes, you will probably look back years later and wince. But next to no one crushes it the first time, anyway.

True, the stakes may seem higher if you’re an entrepreneur debuting your first rev to the world. But Koger, ModCloth’s chief creative officer, insists that getting started is better than waiting till it’s perfect.

Admitting to ourselves that we are bound to err is humbling. But in the business world, where showing confidence and competence are the norm, having humility may be what gives the entrepreneur an edge.

William Marshall, co-founder and CEO of startup satellite maker PlanetLabs, also had some wise words for those interested in entrepreneurship at another recent ETL talk. Actually, he cautioned students at Stanford — all deeply immersed in the Silicon Valley vibe — against “defaulting” to a startup the next time they have an idea that seems to have business potential.

Another non-intuitive bit of advice Marshall shared was to not get an M.B.A. Reflecting on his own career, the former NASA scientist said some of the best physicists he’s known didn’t study physics. “The same is true in business: The best business people didn’t study business,” Marshall says.

But his final bit of advice, in the video below, was to have humility. Rather than promise everyone that you’re going to create a great product, build it first and then show people how amazing it is. Marshall says they will be much more appreciative if you take that approach.

In that clip, Marshall briefly mentions hiring people smarter than you among his tips for future founders. Heidi Roizen, however, shares that same advice, but in much blunter terms. “My goal truly is to be the dumbest person in the room,” Roizen said at her ETL talk last year, titled “Adventures in Entrepreneurship.”

Roizen has spent her life immersed in the Silicon Valley ecosystem, as an entrepreneur, corporate executive, venture capitalist, educator and board member for companies public and private. She is currently is the operations partner at the venture capital firm DFJ and lectures on entrepreneurship in Stanford’s Department of Management Science & Engineering.

In short, she knows what she’s talking about.

As clashes between political parties, socioeconomic classes and ethnic factions dominate current events, it’s clear that we could all use a lesson in empathy. Taking the time to put oneself in the shoes of another and experience the problems they encounter everyday reveals unique opportunities to use our own energy and talents to help others and better connect with them.

In our personal lives, it seems intuitive that exercising empathy allows us to better bond with friends, family and acquaintances. It is, in fact, not so different in our professional lives: Approaching negotiations with the goal of helping the other person get what he or she wants, you both will be better off, according to Stanford lecturer Heidi Roizen, a recent speaker at the Entrepreneurial Thought Leaders (ETL) Seminar Series.

“The art of negotiation is finding the maximal intersection of mutual need,” said Roizen, operating partner at the venture capital firm DFJ, quoting her favorite lesson from her days as a student at the Stanford Graduate School of Business.

Often, the opportunities to practice empathy in a meaningful way exist outside of our own networks and communities. In those instances, that may mean venturing way beyond our comfort zone to truly know the pains others feel.

In her ETL talk last month, Code for America Founder Jennifer Pahlka shared the example of how her program’s fellows enrolled in California’s food-stamps program to find out why so many recipients failed to renew their claim and kept falling off the rolls.

By interacting with the time-intensive and non-intuitive online enrollment system themselves, the coders experienced the full frustration of those actually signed up for the “CalFresh” program. It inspired them to simplify the online process, and build an elegant smartphone app for the many recipients without access to broadband.

But most importantly, the coders kept low-income families from going hungry, and in the process they gained a healthy dose of personal fulfillment.

Sometimes, an entrepreneur’s challenge is recognizing what problem to address. In a world so rich in opportunities, the choice isn’t always quite as clear as we’d like.

But consider this for a moment: Might we be asking the wrong question altogether? Perhaps it’s not a matter of recognizing what problem we’re best suited to work on, but rather, just taking the plunge to help out, experience the journey and see if anything in it speaks to us.

In his ETL talk, Shah Selbe reflects on his own volunteering experiences, underscoring the profound effect they had on what he does now as a bona fide “National Geographic Explorer.” By taking the time to volunteer for what he considers worthy causes, Shah said he gained a deeper understanding of the challenges out in the world, while gaining credibility for working on problems for completely altruistic reasons.

Having empathy is, of course, critical for entrepreneurs seeking to understand and solve people’s pain points. But on a more human level, it helps form meaningful relationships with those in our network — and possibly, compels us to volunteer our time and talents in order to serve those beyond who could really use our help.

The DFJ Entrepreneurial Leaders Fellowship is an exciting new offering at Stanford that will provide 12 outstanding masters-level engineering students with an immersive set of experiences designed to prepare them to lead entrepreneurial ventures.

“Photo Using living cases with Silicon Valley entrepreneurs and investors, workshops and field trips, the selected students will learn the attitudes and actions needed to bring bold ideas to fruition. The Stanford Technology Ventures Program (STVP), which is the entrepreneurship center at Stanford School of Engineering, runs the program, with generous support from venture capital firm Draper Fisher Jurvetson (DFJ).

“Stanford attracts the best young minds in the world and then equips them to make positive contributions as entrepreneurial leaders. We at DFJ have been fortunate to work with many of those entrepreneurs to help them bring their ventures to life,” said Heidi Roizen, operating partner at DFJ.

Roizen, who has two Stanford degrees, is already a valuable contributor to Stanford. She has been a lecturer in the Department of Management Science & Engineering for the past six years, where she teaches a course titled “The Spirit of Entrepreneurship.” Roizen says, “We see the DFJ Entrepreneurial Leaders Fellowship as an opportunity to provide a deeper entrepreneurial educational experience for masters students before they leave campus.”

Stanford engineering students working on a master’s degree are invited to attend one of two information sessions at STVP. The first session will be on Wednesday, Oct. 15, from 5:30 to 6:30 p.m. The second will be on Thursday, Oct. 23, from Noon to 1 p.m.

The DFJ Entrepreneurial Leaders Fellowship (DFJ Fellowship) will run through the winter, spring and summer quarters. In winter, students accepted into the program will attend “The Spirit of Entrepreneurship” (MS&E 178), as well as the DFJ Entrepreneurial Thought Leaders lecture series. In addition, they will meet each Monday night for a dinner seminar featuring special guests from the Silicon Valley ecosystem. 

Also during winter, the students will begin developing their own professional goals, with support from the teaching team, and will be matched with corporate or venture capital mentors. They will also be coached as they find stimulating summer internships that will allow them to use the leadership skills they are developing. 

Spring quarter, students will continue to attend the weekly Entrepreneurial Thought Leaders lectures. In addition, pairs of students will lead evening seminars, working with the teaching team and choosing the topic to be explored.

At the end of spring quarter, the students will present their plan for achieving their professional goals. Then in summer, students will work at a startup company of their choice, enhanced with educational and social programming with all of the DFJ Fellows.

Students who go through the Entrepreneurial Leaders program will be encouraged to help their successors the following year. This pay-it-forward model has been a huge component of the Mayfield Fellows Program (MFP), which served as a model in developing the DFJ Fellowship. MFP is a work/study experience, also run by STVP, that has been immensely successful over the past two decades in helping selected undergraduates at Stanford realize their goals as entrepreneurial leaders.

“This new program is designed around the specific needs of School of Engineering masters students, providing them with a collection of experiences that will prepare them to lead entrepreneurial ventures,” said Tina Seelig, STVP’s executive director and a professor of the practice at the school. “Knowing that masters students are at Stanford for only a year or two, the program quickly exposes them to entrepreneurial thought leaders and connects them with internship and job opportunities in technology ventures.”

The DFJ Fellowship also borrows elements of STVP’s Accel Innovation Scholars program, a yearlong experience for Ph.D. students who are interested in exploring entrepreneurial opportunities in their research. Anaïs Saint-Jude, who helped develop the AIS program in her role as manager of student engagement at STVP, says, “We’re excited to collaborate with DFJ to round out STVP’s fellowship programs, where we now offer high-touch entrepreneurship education programming for undergraduates, masters and Ph.D. students.”

The DFJ Fellowship teaching team will work closely with the students throughout their three-quarter experience, from the articulation of their entrepreneurial aspirations at the outset to the hosting of informal gatherings and workshops at the end to discuss the group’s experiences.

To apply, visit the DFJ Entrepreneurial Leaders Fellowship page.

This month, we decided to turn to our own faculty and staff for their favorite eCorner video clip from the past school year. With so many to choose from, it was interesting to discover that all the picks contained profound observations on the importance of emotional connections and focusing on what really matters in life.

There is no more basic a need than clean drinking water, and yet, diseases from unsafe water and a lack of sanitation kill more people every year than all forms of violence — including war. That’s why Scott Harrison founded the nonprofit charity: water, which has funded over 13,000 water projects in 22 countries since 2006.

Here, Harrison explains how leveraging the strengths of technological tools such as web-based templates, Google Maps and Twitter have allowed his organization to emotionally engage supporters in a way that few nonprofits have traditionally done.

For Matthew Rabinowitz, technological fixes are all well and good. But the most important thing for an entrepreneur to focus on first is a problem that needs to be solved, not some technology invented in the vacuum of a research institution.

Rabinowitz can certainly appreciate this academic lure. He completed his undergraduate, master’s and doctoral degrees at Stanford, receiving the university’s highest student honors in engineering and physics. While completing his dissertation, he co-founded an intelligent online merchandizing company, Panop.com, which later sold for $100 million.

Then in 2003, when a family member had a child born with a genetic disease who later died, Rabinowitz began to see entrepreneurship as a way to address more fundamental problems. Drawing on expertise from his seemingly unrelated background, Rabinowitz embarked on a journey with the goal of ensuring that other families need not experience similar pain wrought by the inability to have a healthy child.

He brought together a team of experts in medicine, engineering, statistics and genetics – and along with his own skills in optimization, signal processing, informatics and entrepreneurship — he founded Natera.

For entrepreneurial thought leadership, you might not think to turn to a Hollywood legend. But during Heidi Roizen’s talk at Stanford last spring, the operating partner at venture capital firm DFJ did just that — evoking the wisdom of longtime entertainer Shirley MacLaine.

Roizen, who teaches a management science and engineering course at Stanford titled “The Spirit of Entrepreneurship,” credited MacLaine with coming up with a so-called “20-40-60 rule,” which sounds like it might relate to ownership splits or stocks.

What the rule actually captures is a far more important insight that is both empowering and liberating for anyone, whether you’re an entrepreneur or not: “At 20, you are constantly worrying about what other people think of you,” Roizen explains. “At 40, you wake up and you say, ‘I’m not going to give a damn what other people think of me anymore.’”

Completing the thought, Roizen then finishes by saying, “At 60, you come to realize that no one is actually thinking of you.”

The course MS&E 178, called “The Spirit of Entrepreneurship,” allows students to get up close and have candid conversations with accomplished startup founders, venture capitalists and other thought leaders from around the country. These practitioners discuss their failures and triumphs and the lessons they now live by — sharing their experiences and insights in a way that is unique even at Stanford.

In other words, students get to be in a room with some of today’s most passionate players in the entrepreneurial ecosystem and ask them how they got to where they are, and what challenges they faced along the way. The course, offered in Stanford’s Department of Management Science & Engineering, is open to undergraduates and graduate students from across the university and has featured iconic figures such as Melinda Gates and Jack Dorsey.

Why call it “The Spirit of Entrepreneurship”? It depends on which instructor you ask. Silicon Valley veterans Heidi Roizen, Ravi Belani and Toby Corey take turns teaching the course each quarter and bring unique perspectives. But they all agree that, fundamentally, the course strives to capture and convey the essence of entrepreneurship through the real-life stories of innovators across the space.

For those students with a sincere curiosity about entrepreneurship, and a willingness to participate — and shape — class discussions, the course can literally redefine how they see the world.

“If you want to take a class that’s going to completely change the way you look at your career and your education — both in and outside of the classroom — then you want to take this course,” said Wade Morgan, a political science major who took the course as a junior in Spring 2014. “This is one of those classes that can really just fundamentally change who you are as a person, for the better.”

Each week, the instructor sends students a set of questions about the upcoming speaker. As part of their grade, each student must then write a thoughtful blog post in response to one of the questions. More importantly, the regular assignments prepare students to come up with meaningful queries for the Wednesday class.

The biggest percentage of a student’s grade (40 percent) is based on participation. The course’s impact depends largely on the quality of the in-class discussions — and whether the questions and comments extract the profound and personal insights of these uniquely accomplished professionals.

“I really believe that the student coming out of ‘The Spirit of Entrepreneurship’ is going to know if starting a company is really for them,” said Roizen, a Silicon Valley native who has spent her career as an entrepreneur, investor and now operating partner at the venture-capital firm DFJ. “And it’s really going to help that student also understand, as they leave Stanford, do they want be involved in a small company? Do they want to be involved in a large company? If a large company, how do they bring entrepreneurial thinking to it?”

The course’s guest speakers are the featured presenters in the weekly Entrepreneurial Thought Leaders Seminar, the popular series followed around the world via Stanford’s ECorner. Recently, the class has welcomed venture capitalist Tim Draper, tech sage Tim O’Reilly, Endeavor CEO and Co-Founder Linda Rottenberg and Khan Academy Founder Sal Khan.

“Something that really struck me was the degree of authenticity that these very successful and influential entrepreneurs had — and they all had really nuanced stories,” said undergraduate student Stephany Yong, a symbolic systems major who also took the course last spring. “This class definitely opened my eyes to how much entrepreneurship is a lot more than just startups. It’s about that mindset.”

Beyond a mindset, entrepreneurship is “multidimensional,” according to Toby Corey, MS&E 178’s spring quarter instructor. As he likes to put it, “entrepreneurship is a universe wide and a universe deep.” And he should know. Like Roizen, Corey has worked in all facets of tech: starting out as a software test engineer and project manager at a large company, Corey later served as a vice president at Novell.

His biggest entrepreneurial splash was co-founding and leading a web-development firm in 1995 that grew from two people to more than 5,000 employees over the course of four years. When USWeb went public, it was the largest company of its kind — with $1 billion in annualized revenues.

“There’s no greater opportunity to learn than literally sitting down and being able to ask a question,” Corey said, “and then having that successful entrepreneur answer you.”

Fall quarter instructor Ravi Belani said, back when he was an undergraduate at Stanford, there were few Indians in venture capital. He nonetheless dove into the valley’s startup scene as a venture capitalist, stressing that students now have the benefit of seeing people they can relate to because “The Spirit of Entrepreneurship” features such a diverse array of speakers.

“Seeing someone who you can reflect upon, a person who was just like you, and seeing that they’ve changed the world, can be incredibly expansive in terms of what you know is possible,” said Belani, who now runs the tech-venture accelerator Alchemist.

Stanford alumna Aditi Maliwal took MS&E 178 her senior year as a psychology major. She previously spent a summer working on Deutsch Bank’s technology-investment team. The experience set the trajectory of her career after Stanford. But at the time, it also limited her ability to understand the entrepreneurial side of the many tech companies she encountered.

Maliwal wanted to learn how these companies built themselves and know their growth strategies. Taking the course allowed her to understand startups from the perspectives of engineers and business professionals alike, which then fueled her as she continued along her career path in venture capital and freed her to see it as no less entrepreneurial than that of a startup founder.

“I will be entrepreneurial in the path that I take and continue on in venture capital,” said Maliwal, who now works at the firm Crosslink Capital. “The best part about taking this class is that it allowed you to expand the definition of what entrepreneurship is.”

That’s exactly what the course’s instructors and creators want to hear. MS&E 178 was developed by the Stanford Technology Ventures Program, the entrepreneurship center in the university’s School of Engineering. And one of STVP’s main goals is to bring the entrepreneurial mindset to every student at Stanford.

“It’s about going after something even if you don’t have the physical resources to do it; and your currency, then, is your spirit. That’s why we call it ‘The Spirit of Entrepreneurship,’” said Belani, who considers entrepreneurship no less than one’s “highest calling” in life.

“It’s about cultivating what’s unique within you to change the world,” Belani explained. “All human beings are inherently creative, inherently innovative and need to be entrepreneurs in whatever facet makes sense within the context of their life.”