San Francisco, Stanford Business School, and Silicon Valley: A Journey with Endeavor’s Entrepreneurial Program

Last year, I wrote about my experiences at Harvard Business School, as a part of the Endeavor Program. This summer, I had a chance to re-engage with Endeavor (Jobsity has been a part of this program since late 2017) in the heart of Silicon Valley: in San Francisco and on the campus of Stanford University. The experience, much like the one I had last year at Harvard, was transformational. Today, I want to share some of what I learned, and some of my reactions to this incredible opportunity.

“The coldest winter I ever saw was the summer I spent in San Francisco” - Mark Twain

Our first stop this summer was the City of San Francisco, a place like no other when it comes to misty mountain views, and networking. As they say “80% of success is showing up,” but in San Francisco, the percentage might be higher. As part of Endeavor, I was privileged to attend talks by two of the Valley’s biggest hitters: Phil Libin, co-founder and CEO of Evernote, and Simon Rothman, a partner at VC firm Greylock.

Both were impassioned and knowledgeable speakers, and learning in their presence was an honor. But more than that proximity was the lessons I learned about what it means to be at the center of tech entrepreneurship: how the interconnected ecosystem of San Francisco and Silicon Valley depends upon VC, CEOs, and entrepreneurs alike deciding to stay open, to listen, and to connect. One casual conversation I witnessed between a friend and a stranger at a mixer ended with my friend directly pitching a top VC. That’s not just San Francisco’s magic, it’s a lesson we can all take back to our home contexts.

Inside the conference room, San Francisco feels like a place where people are changing the world (and it is!). But outside, it’s a city that is facing challenges—and this contrast I had not anticipated. Homeless is an issue, and the division between the “haves” and “have nots” is quite visible. According to HUD & SF Department of Homelessness and Supportive Housing, “In 2019, San Francisco reported 8,011 homeless people met the federal definition of homeless, an increase of 17 percent from 2017. When looking at San Francisco's expanded definition, the city's 2019 total homeless population is 9,784, the highest in the Bay Area.”

I left the talks feeling hopeful and inspired, but also couldn’t help but feel that some of the most immediate challenges are right there just outside the boardrooms of San Francisco. Overall, my heart was filled with hope for a changing world, and a hope that that change will begin to be shared with everyone.

From Contrast to Campus

The next day we traveled to Palo Alto to begin the program in earnest on the campus of Stanford University. This was a complete “180” from San Francisco, in almost every way.

To say the least, Palo Alto is different. It embodies the full California experience: small towns, great schools, an affluent lifestyle. Immediately, I felt like I didn’t want to stay for a few days of learning, but for a lifetime of study.

And then there’s the Stanford campus in the middle of it all: the most beautiful campus I’ve ever seen. The weather was temperate, there were bikes everywhere, it felt safe and comfortable. But not only that: every fiber of the environment embraces the concept of study. Just being there, I felt the desire to pick up a book and become a student again. Maybe that’s not everyone’s reaction, but for me it was very inspiring!

According to campus lore, one of the founders asked for all the roofs on campus to be made with Spanish tile so that upon her death she could see it from heaven. Now, you can literally see Stanford from a satellite: it’s a universal emblem of studiousness and intellectual expansion.

“Stories don’t motivate, they coordinate”

On Monday we began the program. It started slow. The early part of the week was focused on the tech-entrepreneurial environment, and on providing tools to help us navigate interactions with Venture Capitalists.

We learned about customer advisory boards: something we could bring to our businesses to help ensure that we’re responding to the needs of our customers most effectively, and to help us scale in specific response to those needs. We also learned about the power of storytelling in business.

The questions we were taught to ask were: can you tell a story about your company in a way that inspires? Can you truly translate your thinking and your values into your company story?

We also learned to conform this narrative to story structure: to align it with platform, person, place, tilt, motion, events, climax, and the new reality. We learned what might seem obvious, but what we can’t afford to forget: that unless the story of your company is the story of you or your company changing, then this isn’t really a story, it’s just an anecdote. And anecdotes don’t move people.

Finally, we learned a lesson about how to use stories with your team: that we tell stories in business not to motivate, but to coordinate. Like, BP getting their entire worldwide company on board to “slam the clam” (i.e. beat Shell) the most compelling stories will get your whole team on the same page in regards to a big mission, vision, or goal. Or better yet, all three.

It’s not just the ‘where’, but also the ‘who’

The Endeavor program is known for its immersive curriculum. But that’s only half of what makes it such a powerful experience. The other half are the peers you’re put in contact with. Your cohort. Your impressive, international peers.

One night over beers, I had this conversation with one new friend: What is the difference between an entrepreneur and a person who decides to start a business?

For him, the job of a business owner is to make his business work. But the job of an entrepreneur is to develop a life based on generating business, and businesses. The difference? In one, the goal is linear: to stay afloat, to grow your project, to earn a living. For the other, it’s exponential. A true entrepreneur’s life should be spent building not one business, but a formula for creating business, and then testing, tweaking, and retesting that formula again and again and again.

This got me thinking about my work as more than just a job: but as my life’s purpose.

With another peer, I spoke about the differences between the way Jobsity was born, and the way his Brazliian business took off. Ours was a bootstrapped business: we were never given any funding! But his took in tens of millions very early on. This difference didn’t make us feel tension, however. He was able to appreciate how hard it was for us to start without funding, and I was able to appreciate how hard it was for him to start by receiving funding.

We were both aligned on one essential truth: the important thing is to plan how to run your company, not only on how to get funds. In other words: Don’t plan for the wedding, plan for the marriage.

In the end, we were gifted a unique opportunity: to learn from each other even though we run businesses in different industries, thousands of miles away, and had such different professional beginnings.

Because of our time at Endeavor, we were able to learn, grow, and study together, because of—not in spite of—our differences. That’s the secret magic of Endeavor.

“What is more important: people, market, client, or service?”

Because Endeavor is focused on giving early traction companies the tools to scale and expand, a central focus of our time at Stanford was to learn how to navigate the world of Venture Capital. This included a real-time pitch to a VC in front of all 50 of us. It was an incredible exercise: we got to feel the fear and the nerves, to see the small movements and emotions, and to share the realities of the successes and stumbles of the unique interaction from just a few feet away.

Because of this, we spent a great deal of time talking about trust. That if you don’t trust your employees, they won’t trust you. And if they don’t trust you, it’s doubtful your clients or customers will trust the company at all. Which is not even to speak of VC’s trusting your vision.

Take, for example, the airlines: these days, no one trusts an airline. Whether you get a good deal or not, you always feel like they’re ripping you off. If your business gets close to that, you’ll have a lot of work to do to turn such distrust around. Using customer surveys and other tools, it’s better to build an ecosystem of trust from day one.

At another point, we were asked: “What is more important: people, market, client, or service?”

Most of us assumed it was people. We were wrong.

The most important factor when a business is looking to scale is the market. Then comes your team. If you want to launch a scalable business anywhere in the world, you have to know that the market is there to meet it. Only then can you use your entrepreneurial talents—and your superlative team, and the trust they engender—to start scaling.

Your brain is a machine: fine tune it

Another important topic we explored was decision-making.

First, we investigated the brain chemicals which determine excitement and boredom, concentration and stress, and how they influence decisions affecting your bottom line.

When you’re leading a team, it’s important you know how your lifestyle influences how you feel, and how you feel influences how to make choices at work. Don’t underestimate the power of serotonin and cortisol (hormones that mitigate boredom and stress) and dopamine (which gives you confidence and excitement) in influencing your ability to think clearly and act with purpose.

It sounds simple: try to make important decisions in the morning after a good night’s sleep. Don’t raise your serotonin and cortisol first thing: don’t wake and check email. Think about how those chemicals influence your life—because they do, whether you’re aware of it or not.

What is the problem you are trying to solve?

After engaging in thought about how our internal chemistry influences our leadership, we began to investigate the external chemistry we, as company leaders, experience as we navigate our work.

We did a hiring exercise: everyone was given specific feedback about two candidates and then told to make a zero sum choice—which person was better for the job?

Based on the specific set of data each of us received, we all made different “informed” choices. Yet when we all saw all the data, it became clear that only one candidate was the right fit. At all. The lesson? All information is not created equal.

You might choose one side of a debate because that side is getting more positive feedback. When in fact, the feedback from the other side is getting—while less in quantity, is better in quality. The balance of ‘how much’ positive and negative information you have depends both on who you ask, and what their agenda is.

The takeaway? Pay attention to the intrinsic correlation between the information provided by each person involved in the decision, and by what interests they bring to the table.

Another tip: do a pre-mortem. Before you decide, imagine the worst case scenario. This will help you uncover hidden information about the decision you’re about to make, and to separate it from the people involved.

Also, don’t shy away from asking these questions: what is the problem we are trying to solve?

California Dreamin’

Toward the end of my time at Stanford, we had a chance to see the new Tarantino film, “Once Upon a Time in Hollywood.” The film, unrelated to any concrete lessons presented in the Endeavor curriculum, got me feeling the specialness and power of being where I was, and learning what I was privileged to learn from the people I was learning with.

When the song “California Dreamin’” came on, with Puerto Rican musician Jose Feliciano’s strummed Spanish guitar, I felt connected both to my own Spanish-speaking culture, and also rooted in the magic and power of the dreams that seem to take flight in California.

I can’t help but feel that with the brain trust, the ecosystem, and the relationships blooming in that temperate State, that everything in our world is going in the right direction.

Yes, there’s something very special how the Valley has already changed the world, peoples’ lives, and my life specifically. Yes, it’s capitalistic and for profit, but it’s also beautiful: to see people doing amazing things that are having such a powerful effect on everyone alive, to have the chance to be a part of it, and to bring some of that learning to my network and my peers, in Ecuador, in Latin America, and everywhere online.

It was beautiful and inspiring to be a part of it and to have a chance to learn from it, and I feel more connected to my purpose than ever.

So join me in saying: “California Dreamin’—dream on!”

A few phrases from lectures and discussions that have stayed with me:

• Time is the killer of all deals
• Your finance guy should know how to do two things well: 1: Say No; 2: No surprises
• If you are at a crossroads in your life and need to make a decision, usually the right choice is the hard one
• Take risks; take two steps more risk than you can handle
• You are going to be the first one to know if something is wrong in your company and the last one to believe it
• If you build a polished prototype, others will see flaws. If you build a rough prototype, others will see potential.
• Excellence is an organization full of people who don't need policing
• Stories don’t motivate, they coordinate

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