My Experience at Draper University: What I Learned From Billionaire VC Tim Draper

In the Summer of 2021, at the age of 20, I had the privilege of attending the most prestigious pre-accelerator program in Silicon Valley: Draper University. As I flew out from Boston for the 5-week Hero Training program, I had no idea that it would be the most transformative experience of my life. The Hero Training program was built on the premise that startup entrepreneurs can, with the right tools and knowledge, accomplish “heroic” feats. Draper University had an impressive track record of helping entrepreneurs do just that. At the time that I attended the program, they had already trained thousands of “heroes,” with one of those graduates already going on to create a billion-dollar company. While most educational institutions boast job placement rates, Draper University instead provides the metric that their average graduate creates 5 jobs.

Draper University was founded by one of Silicon Valley’s greatest venture capitalists of all time: Tim Draper. For decades, Draper has backed blockbuster success after blockbuster success with his portfolio companies including Tesla, SpaceX, Twitch.TV, Robinhood, Coinbase, Hotmail, Skype, Solar City, Twitter, DocuSign, Baidu, AngelList, and Ancestry.com. Draper was successful in globally scaling his venture capital business, a feat previously deemed impossible by prominent VCs, with the Draper Venture Network now spread across over 70 countries. Tim Draper is also known for having purchased all 30,000 bitcoins that were seized from the Silk Road in 2014, at an average price of $258 per bitcoin. Notably, Draper was one of the first investors in Theranos, having known the company’s founder and CEO Elizabeth Holmes since she was a young child. Interestingly, he believes that Theranos never committed fraud, but instead was hit with a massive media slandering orchestrated by healthcare incumbents who were afraid of the disruption Theranos might bring if it completed research and development and got its product out to market. Tim Draper also founded BizWorld, a nonprofit organization that teaches children the basics of business, entrepreneurship, and finance. BizWorld has reached hundreds of thousands of students through over 8,000 educators across 100+ countries.

Draper University was created with the intention of filling the need for a school that taught entrepreneurship without traditional academic methodologies; the university would become the epitome of experiential learning and build its material off Draper’s decades of experience working with some of the world’s most successful entrepreneurs. Being one of the youngest people at the program, I went through recurring waves of imposter syndrome. Of course, I was not qualified to be among the many outstanding entrepreneurs at the program who were much further along in their careers than I was. Some of my fellow entrepreneurs included a woman who was a member of the Argentinian Congress, one of the youngest Tesla employees ever, multiple Olympic athletes, and many self-made millionaires. However, I soon came to find that the skills and knowledge I had learned from the Rines Angel Fund (another high-impact experiential learning program out of the University of New Hampshire) gave me a unique value-add to the program and to its entrepreneurs who were still hunting for angel and VC financing.

On the second day of the program, it was announced that the next morning we would be pitching our ideas for the first time, to Tim Draper. They would be one minute pitches with no slide deck (typical practice in Silicon Valley). This is when I first became aware of the stark differences between the investment atmosphere I was accustomed to in New England and that of the Valley. In New England, pitching a company requires the utmost professionalism and preparation. You need a pitch deck at least 15 slides long, supplementary materials to back up your claims, and entrepreneurs predominantly dress business professional. In Silicon Valley, pitching is treated as more of an art than a science. The pitch is often quite informal (some entrepreneurs pitched at our Demo Day in shorts and sandals) and frequently lacks a pitch deck altogether. The due diligence process in Silicon Valley is also rumored to be less intensive, particularly at the earlier stages of investment when investors are betting more on the founder and the idea than on any numbers the company has to show.

Due to the many complications posed by COVID-19, I had never pitched my idea in-person before, so my first in-person pitch was to one of the most legendary venture capitalists of all time. Despite my feeling of unpreparedness, I found it hard not to enjoy myself that day. As soon as Tim entered the room wearing his signature bitcoin tie, it was as though you could feel his energy and optimism permeating through every inch of the building. He had us do push-ups and jumping jacks periodically throughout the pitch event to keep us on our toes, and he announced our names like an excited sportscaster after a winning touchdown. One by one, we pitched our companies for one minute, and then in true Draper University fashion, we had to dance (or sing) off the stage. As we walked off stage, we were also assigned teams that we would participate in various activities with throughout the program. I was assigned to Team Phoenix and throughout the program, my team members and I went from mere collaborators to lifelong friends.

Later that day, we got to take part in BizWorld’s 6-week program over the course of a mere 4 hours. Throughout the whole experience, Tim’s booming voice could be heard as he spoke to us about our ideas for how we could change the world using only children’s arts and crafts as our means of production. Within those 4 hours, we went through the entire production process all the way through to marketing & sales, and created income statements, cash flow statements, and balance sheets. I imagined thousands of elementary-aged children going through these activities and couldn’t help but smile at the thought.

Once the BizWorld programming was over, Tim took us outside to stand by the pool. He gave us what sounded like a well-rehearsed speech about the difference that entrepreneurs make in the world and how one goes about becoming a great entrepreneur (what he calls a “Startup Hero”). Near the end of the speech, he starts taking off his shoes and says: “So, what do you do once you have everything in place? … YOU JUMP IN!” He immediately leaps into the small pool in full suit and tie, followed by all 80 of my cohort’s entrepreneurs enthusiastically launching themselves into the water behind him. A handful of these entrepreneurs could not swim, so Tim spent the rest of his time with us that day teaching swimming lessons. 

At the outset, I thought that day would be long and stressful, though valuable. Instead, it was perhaps the most fun I had had in years. After the day’s programming ended, I realized that my face ached from the constant smiles and laughter. This was a common theme at Draper University. Tim always said he had never seen a great company that got there without having lots of fun along the way. The importance of fun, not just when running a company but when living life in general, has stuck with me ever since that day.

That Friday, we participated in a 48-hour Hackathon challenge. Our task over that time period was to design a company centered around artificial intelligence and/or decentralization, complete with a working product, a website, and a pitch to be delivered Sunday morning. The first prize was a free skydiving session, so there was obviously a high degree of competition. My team came up with the idea to create an NFT platform on which valuable identification documents (license, passport, social security card, etc.) could be stored. If fully integrated into government services, this platform could save citizens the cost of being issued physical documents and the time of waiting for them to come in the mail. Most importantly, however, it would provide a more secure way of using identification documents. Physical documents are easily lost, stolen, or destroyed. In contrast, the blockchain is far more secure. The importance of this issue was demonstrated to me when I went on a road trip with another Draper University graduate after the program ended and experienced this problem first-hand after some of her documents were stolen out of our rental car.

Over the weekend, we labored and created a beautiful pitch deck, website, and some code for a prototype. While we did not win the Hackathon that Sunday, I did end up joining the winning team on their skydiving trip near the end of the program (paying for the privilege, of course). Our Hackathon idea is now being developed by some of my team members into a real company. It wasn’t the only idea generated in that Hackathon to go on to become a real company, either. Like many other exercises at Draper University, the Hackathon taught me how easy it was to make incredible progress on a company in a matter of mere days or hours - especially when you have a highly motivated, qualified team. Day after day, the Hero Training program withered away my preconceived notions about what running a startup was like.

After the Hackathon ended, we started to prepare for “Survival Week,” the program’s trademark character-building exercise featuring Navy Seals and Special Forces as our supervisors and guides. Prior to starting the Hero Training program, all of the entrepreneurs signed the most comprehensive liability waiver imaginable. This waiver absolved Draper University from liability for just about any way you could imagine dying in Northern California. The Survival Week staff jokingly bragged that although they had the waiver just in case, no one had ever died during Survival Week.

I am under NDA so I cannot say exactly what happened once Survival Week began, which is unfortunate because it was one of the best parts of the program. However, I can say what Draper University has already publicized, which is that we walked 78 miles over 4 days. The things we did during Survival Week were high-risk high-reward just like entrepreneurship.

After arriving back from Survival Week, they gave us two much-needed days of rest. This unforgettable adventure will stick with me forever, just like the grass and burrs in the fibers of my socks from our many treks. Once we were sufficiently rested, the program kicked off a week filled with top-tier CEO and venture capitalist guest speakers. Some of the most notable include Andy Yang (CEO of Indiegogo), Phil Libin (Founder of Evernote), Derek Andersen (Founder of Startup Grind), and Andy Tang (CEO of Draper University & Partner at Draper Associates and Draper Dragon). Derek Andersen was one of the most inspiring founders I have ever met. His entire talk focused on encapsulating one’s values in one’s business and the way that having a giving mindset helped him build meaningful relationships, both in business and in life. 

Andersen also told us the story of how his company came about. When Andersen was new to entrepreneurship, he kept having “bad ideas” (his words), but he never stopped trying to get them adopted and trying to get them funded. In the process of trying to get his ideas adopted and funded, he hosted several startup events that were huge hits with their attendees. One person said to Andersen, “I don’t know about your business ideas, but these events you are putting on are great. Maybe you should focus on that.” Suddenly, Andersen realized that his knack for building communities would be a better business model to pursue. Today, Startup Grind has scaled to connect two million entrepreneurs across 600 cities and 125 countries. Perseverance is the key to success in entrepreneurship.

The tail end of the Hero Training program was just as challenging and exciting as the first. Much of it centered around Demo Day: the day we pitched our ideas to Tim Draper and about 120 angels and early-stage venture capitalists. Two days before Demo Day, we were treated to a day-long leadership training session with Gina Kloes, an accomplished Tony Robbins acolyte with contagious energy and enthusiasm, and Juan Acosta, a startup entrepreneur with a winning mindset. There, we learned an incredible thought framework to set ourselves up for success.

First, one must focus only on what they can control. Losing sight of what is controllable is a common pitfall that drags entrepreneurs into burnout and time wasting. The three major controllable areas in business that are critical to success are strategy, the stories you tell yourself about yourself, and state of mind, they said. Most entrepreneurs and investors behave as though strategy is 100% of what decides the winners and losers in business. According to Gina and Juan, it is a mere 20%. The entrepreneurs that succeed in business have a positive state of mind that leads to stories they tell themselves that evoke confidence, conviction in their visions, and determination to succeed. I thought back to Derek Andersen’s story and I knew that Gina and Juan must be right. It is easy to look at a story like Andersen’s and say that he succeeded because he didn’t give up, but why didn’t he give up? Positive mindset. Tim Draper and Andy Tang frequently said that many of their best portfolio companies were C ideas, but were run by entrepreneurs with A-plus mindsets and drive. Later that day, we engaged in an hour-long meditation session. The key to taking control over one’s mindset is mindfulness and self-awareness, a skill best refined through meditation.

How did all of this relate to leadership? We learned a lot about leading others during Survival Week, but after you have those skills and knowledge, what differentiates the best leaders is the ability to lead oneself. Leading by example and bringing all of one’s energy, excitement, and passion to work everyday creates a fun and dynamic work culture, encourages positivity and therefore motivation, and sets the tone for how the company will treat its stakeholders.

After leadership training was over, Demo Day was upon us. We each got to pitch for two minutes (with a slide deck) to a room full of investors. It was nerve racking, but Tim Draper kept our energy and optimism up with his trademark jumping jacks, push ups, and intermittent dance parties. Unfortunately, the investors I invited did not necessarily enjoy watching my cohort engaging in these uplifting activities. However, the event would not have been the same if we had been sitting in our chairs for the entire eight hour event. Maybe these techniques could be transferred to other events that could use an energy boost.

My co-founder Daisy and I delivered our pitch. There were technical issues for some of the other pitches but luckily, ours went smoothly. Daisy was a whiz at answering questions from Draper and a few other investors. I breathed a huge sigh of relief. We were not awarded “Top Ten Most Investable” that night, but I was incredibly proud of our performance and several of my fellow entrepreneurs told me they were surprised we did not make the top ten. The next day, I received a handful of emails from interested investors. Our hard work had paid off.

Following Demo Day, it felt like the program was over, but it wasn’t. The Draper University staff had a few more events and challenges up their sleeves to keep us engaged for the remaining week of the Hero Training program. The first of these activities was a Silicon Valley tour in which we visited the campuses for Netflix, Google, Apple, Facebook, and Andreessen Horowitz. We were not necessarily allowed to be in these places, so we were frequently accompanied on our tour by unsettled security guards.

Earlier that day, we had breakfast with Tim Draper’s father, who is largely credited with making the venture capital industry what it is today. Bill Draper was also, at different points in his career, president and chairman of the Export-Import Bank of the United States and second in command at the United Nations. Even the restaurant we ate at, Buck’s of Woodside, had a rich history to it. The restaurant was frequented by Silicon Valley legends, with a seat reserved solely for Bill Gates. I sat at the table where PayPal was founded. Across the room were the tables where Tesla, Hotmail, and Netscape were founded. The food was fantastic too.

Later that week, we were issued our last great challenge. We would have 24 hours to go into the city of San Francisco and get a full-time job. Bonus points were given for weird or high-paying jobs. There was another catch. Due to the job shortage in the city, we were asked to not only find a job but work that job on the day we got it. I got a job selling bus tickets for San Francisco tours. It was a lot more difficult to sell the tickets than I thought it would be, but I did make a handful of sales. After experiencing almost constant rejection for a few hours, I gained a lot of respect for people who had to make cold sales day in and day out. The best of my fellow ticket salesmen did exactly what they taught us in leadership training; they kept a relentlessly positive mindset and didn’t let the constant rejection inherent to the job bring them down. 

After selling bus tickets for a few hours, I spent the rest of the day enjoying the city, knowing it would be one of my last days in California. My cohort later reconvened in a large park at the heart of the city, where I heard that another entrepreneur got two jobs: one paying a $70,000 salary and another from Wells Fargo paying $180,000 per year. The Draper staff revealed that they gave us this challenge to show us how easy it would be to get a job if we were running low on money and needed a job fast to keep our startup alive. Some of the other entrepreneurs learned that they could also make a fortune in the corporate world if they wanted to. Once again, I was humbled by my peers.

A few days after this challenge was over, we attended our graduation ceremony. Andy Tang gave an inspiring speech to kick off the event. He shared that he came into the United States as an immigrant from Taiwan at a young age. His family was poor and he went to college solely on Pell Grants. “Now, I pay more than my tuition was every year in taxes,” he said, “I guess the government understood return on investment.” We laughed.

We were each given masks and capes, a reference to the hero analogy the program was based off of. Each cape had our “superhero” names on the back of it. Every team had one member give a heartwarming speech about their time at Draper University (I was lucky enough to give my team’s speech). We were all on the verge of tears, knowing that soon we would all be scattered across the globe and the close bonds we developed would become permanently long-distance. After each team delivered their speeches, we hopped down a line of three trampolines into a huge pile of bean bags. It was a fitting end to an unparalleled personal and professional journey.

This experience offered many valuable insights. Firstly, it demonstrated the true merit of experiential learning - a concept I was already passionate about. The UNH Rines Angel Fund is another great example of experiential learning put to practice and it was undoubtedly because of my time at the Rines Fund that I was able to succeed at Draper University. The amount I learned about entrepreneurship at Draper University was completely disproportionate to the amount of time I was there and it was all from doing, not watching a lecture and taking notes. Whether entrepreneurship is in actuality more of an art than a science, I believe something is lost when business is treated as purely a science with objective right and wrong answers. Granted, there are and always will be objective, quantitative components of business that need to be understood and given due attention. However, it is through creativity and a willingness to fail and fail again until achieving success, that the most difficult problems can be matched with breakthrough business solutions. Sometimes, it is more useful to imagine what the future could be like than focus on how markets have perpetuated in the past. That is the premise of futurism, a topic rarely discussed in traditional academia. Futurist thinkers have nonetheless been incredibly influential throughout history (think of the Founding Fathers, Thomas Edison, Steve Jobs, and many more).

The craziest ideas are the ones that have the biggest impact if they succeed. Tim Draper always said: “If you are having an easy time fundraising for your company, you’re probably not pushing the envelope enough. Truly disruptive companies should seem crazy to most investors.” This was his biggest piece of advice to our Top Ten Most Investable companies at Demo Day, who were obviously well-liked by investors. The futurist mentality pays in the venture capital business. Many of the companies backed by Draper were trying to do things deemed virtually impossible at the time. Commercial spaceflight, autonomous electric cars, free email, and mass market cryptocurrency investing would have been rapidly denied capital at their time of emergence if every investor governed their decisions based on what happened in the past. Instead, companies doing these “impossible” things became Tim Draper’s biggest hits, because he saw their potential to change the world.

Truly disruptive companies do not fit into their markets neatly, either. Instead, they disrupt them by fundamentally changing the game. Airbnb is nothing like hotels, motels, or anything else in the hospitality industry. Yet today, they hold massive market share, grew the hospitality market, and went public at over $100 billion. Learning about how to spot disruptive potential has forever changed how I will evaluate startup investments.

The lessons I learned at Draper University are best represented by the Hero’s Oath, a pledge written by Tim Draper that we read together every morning at Draper University:

• I will promote freedom at all costs.

• I will do everything in my power to drive, build, and pursue progress and change.

• My brand, my network, and my reputation are paramount.

• I will set positive examples for others to emulate.

• I will instill good habits in myself. I will take care of myself.

• I will fail and fail again until I succeed.

• I will explore the world with gusto and enthusiasm.

• I will treat people well.

• I will make short-term sacrifices for long term success.

• I will pursue fairness, openness, health and fun with all that I encounter. Mostly fun.

• I will keep my word.

• I will try my best to make reparations for my digressions.

My hope is that in the future every entrepreneur will have access to experiential learning opportunities, such as those provided by Draper University and the Rines Angel Fund, and that the entire entrepreneurial ecosystem can wholeheartedly embrace both the art and the science of entrepreneurship.