7 Marketing Secrets from 500 Startups Demo Days

Have Fun, Get Deals Done – The Future of Marketing is the Brand Experience

Pitching to top Silicon Valley investors like Tim Draper is nerve-racking. It helps when he’s dressed in a superhero costume.

From Valentine’s Day-Themed (Batch 19) to Summer of Love-Themed (Batch 20), 500 Startups Demo Day is more than a pitch day, it’s a festival where everyone has fun and gets deals done.

Here’s a look back at lessons we’ve learned from the last 7 Demo Days, and how 500 Startups stumbled upon creating the unique pitch day in Silicon Valley.

1. Listen to Your Audience

Back in the day, 500 Startups Demo Day was pretty basic (see Batch 8):

500 Startups Founding Partner, Dave McClure, speaking at 500 Batch 8 Demo Day (back when the most colorful thing at Demo Day was Dave’s language).

During Batch 13 Demo Day, things got a little bit more interesting.

It all started when I bought Dave a unicorn hoodie for his birthday, which happened to coincide with the Batch 13 Preview Day (an invite-only sneak peek to Demo Day). To our surprise, many investors and founders in the audience loved Dave’s unexpected fashion statement, talking and tweeting about it.

Dave noted the audience engagement and decided to wear the unicorn costume again on Demo Day. He also encouraged Founding Partner Christine Tsai, a former ballerina, to wear a rainbow tutu. Again, the response was extremely positive at Demo Day. Silicon Valley Business Journal even dedicated an article to Unicorn theme.

The lightbulb turned on, and we saw the potential marketing value in bringing creativity to our Demo Days. But it wasn’t a mere fluke — we listened to the audience feedback, saw the marketing value, and applied it.


2. Turn Challenges into Creative Advantage

When planning for Batch 14 Demo Day, we found out the only day the venue was available was the day before Halloween. We were not happy. Typically we tried to plan our events around major holidays, like Halloween, assuming people would be busy attending their own company parties. We were worried about not having enough investors attend our event, but we couldn’t change the date. So we decided to exploit the timing instead. Thus, Demo-Ween was born.

In our past Demo Days, we always focused on the pitches, not wanting to take away from the big day of our batch companies. However, the thematic timing forced us to look at the Demo Days from a different angle. We decided to make Demo Days more entertaining. We added the Halloween theme to our Demo Day, aka “Demo-ween” — presenting the content in a new form. The new form of Demo Day allowed startups and investors to dress up, have fun, and get deals done together.

As a result, the Demo-ween not only helped us maintain the previous demo day attendance, it also attracted more international investors than ever before (50% increase). By presenting the content in a more engaging format, we turned a challenge into our competitive advantage.

The first Demo-ween was so successful, we decided to make it an annual theme. 

3. Use Product-Launches to Rejuvenate Your Brand

In 2016, we started adding speciality tracks to our seed program, starting with a Fintech track in the Batch 16 program.

In order to highlight our new Fintech focus, we made the Batch 16 Demo Day poker themed. In order to create an authentic experience, the 500 events team hired a top poker player to give attendees poker lessons and play blackjack. Founding Partners Dave McClure and Christine Tsai also dressed up for the poker theme.

Partly in thanks to a successful Fintech-Themed Demo Day, we saw a 23% increase in Fintech applications to the following batch.

4. Embrace Company Culture

During the Batch 17 program in June 2016, the 500 team and batch companies attended the San Francisco Pride Parade. Pride inspired us to redefine the meaning of “unicorn” at 500. In tech, a unicorn company means a billion dollar company valuation. We decided that being a unicorn also brings about a sense of love and unity. We are not only about making profits and increasing portfolio company valuations but also about celebrating people and culture.

The momentum of the Pride Month continued into our Demo Day planning process. We wanted to use the upcoming Demo Day as a platform to promote 500’s company value of embracing diversity and inclusion. We chose the theme “Beauty & the Geek” based on our B17 tracks Fashion & B2B and decided to break down gender stereotypes by having Dave dress up as the “Beauty” and Christine the “Geek”.

After Demo Day, Microsoft offered to sponsor our efforts to advocate diversity in tech by supporting our Unity and Inclusion Summits. Our open and embracing culture has attracted a very diverse group of companies. In our latest batch, Batch 20, 36% of our batch companies were international (from 10 different countries), 20.5% of companies had at least one female founder, and 25% of companies had a black / Latinx founder.


5. Make It About Your People

At the end of the Batch 17 Demo Day, a flash mob of the 500 team appeared from the audience and started dancing on stage with Dave. The big screen started playing videos of venture capital investors and founders of successful 500 portfolio companies around the world wishing Dave a happy birthday. The B17 Demo Day happened to be Dave’s 50th birthday and our 500 family planned a surprise for Dave.

The Demo Day birthday surprise is just one example of the many things that we would do simply because we care about people. We build the 500 brand by connecting with people on a personal level.

6. Create Positive Emotion

From the previous Demo Days, we began to see that themes created a supportive environment for founders and investors to develop relationships. For Batch 19, we chose a Valentine’s Day theme because we wanted to bring more emotion into the experience.

We dressed up our founders as Cupid (Christine) and the Queen of Hearts (Dave) and decorated the stage with all shades of pink and hearts. Investors could give batch companies Valentine cards that said, “I have my eyes on you!”.


7. Leverage Culture & History

Our Batch 20 program was based in San Francisco around the same time as the city’s 50th anniversary of the “Summer of Love” – the 1967 summer event that drew nearly 100,000 young people to the city’s Haight-Ashbury neighborhood. Starting from early spring 2017, streets in San Francisco were decorated with the “Summer of Love” theme. We decided to do the same theme for our Demo Day to pay tribute to the city’s history.

With flowers, rainbow-colored lighting and our emcee in a Grateful Dead bear costume, this Demo Day brought a sense of nostalgia to the city many 500 Startups team members call home.


Our Demo Days are instrumental in building the 500 brand. We strive to create an organic ecosystem of investors, founders, and corporate partners by providing meaningful and engaging content to our audience.

If your goal is to stand out from the crowd and flaunt your unique brand to the world, don’t forget to incorporate these 7 Marketing Lessons from 500 Startups Demo Days:

  1. Listen to the Audience: Gather feedback from your audience, catch the opportunity, and act on it
  2. Reframe the Challenge: Look at the problem from another perspective and turn challenges into advantages
  3. Inspire with your products: Rejuvenate your brand with new products
  4. Embrace Company Culture: Integrate the company values and culture to create a powerful marketing message
  5. Focus on People: Build a people-centric ecosystem to organically grow your business
  6. Engage your audience with Emotions: Create Positive emotions to Drive Connection and Awareness
  7. Integrate Art into Business: Leverage the power of culture and history in your marketing

500 Batch 22 begins July 24th, 2017 in San Francisco.

Click Here to apply for our the Batch 22 Seed Program.

More from Yiying Lu: 


Yiying Lu is award-winning bilingual (English & Chinese) artist and designer. Born in Shanghai China, Educated in Sydney Australia & London UK, now based in San Francisco, Silicon Valley, she currently is a Design Lecturer at the NYU Shanghai Program on Creativity & Innovation. She is also an individual creative consultant who provides talks & workshops for global startups and corporate innovation teams on design thinking, entrepreneurship & creativity. Her projects have been featured in many publications, including The New York Times, Forbes, NBC News, TIME, CNN, BBC, San Francisco Chronicle, TechCrunch, Mashable, and The Huffington Post. She was named a “Top 10 Emerging Leader in Innovation” in the Microsoft Next 100 series. For more from Yiying, you can follow her on TwitterLinkedin and Medium.


4 Realizations From My Day In Prison

Yesterday, I battled torrential rain and excruciating traffic in a 2.5 hour drive up to Vacaville. Needless to say, I wasn’t in the best mood when I finally arrived at my destination — Solano State Prison. However, the grumpiness melted away immediately when I was greeted by one of the guards.

He was the polar opposite of what I would expect from someone guarding the entrance of a prison — cordial, friendly, and mild mannered. With a warm smile on his face, he asked me if the drive was okay, which bridge I took. Then, after directing me to the right parking lot and where to go, he bid me a kind farewell.

Not at all what I expected. It was just one of many surprises in store for the day.

It was my first time in prison. I was there to volunteer with Defy Ventures, along with 500 teammates Tara Graham, Brian Wang, and Aerin Lim. While I didn’t feel particularly scared about going to prison, I had no idea what to expect.

Was Defy really as amazing as I had heard from my colleague Andrea Barrica ?
Would I end up feeling unsafe in any way?
Would we have real impact on the EITs? (Entrepreneurs-In-Training — the inmates participating in the Defy program)

I was blown away by the experience and found myself surprised many times. I’d like to share a few thoughts below.

The irony is that none of these things are legitimate surprises or brand new information. Rather, they all seem like common sense. However, you don’treally get it until you’ve seen it for yourself.

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1. Inmates and Volunteers Aren’t That Different.

In fact, we are shockingly similar. The morning kicked off with a series of ice breakers led by Catherine Hoke (Defy Founder & CEO). One of them was an exercise where a line was taped down in the middle of the room. EITs and volunteers stood on opposite sides of the line. Catherine would then read aloud statements, and people on either side would step to the line if it applied to them.

They ranged from light-hearted (“I like hip-hop”, “I like country music”)….

…to a little more personal (“I graduated from a 4-year college”, “I dropped out of high school”)…

…to really personal (“I lost one of my parents before the age of 18”, “I grew up in a neighborhood where gunshots were heard regularly”, “I’ve committed a violent offense whether or not I was caught”)…

…to introspective (“I feel like I constantly judge myself”, “There are things in life that I haven’t yet forgiven myself for”).

At one point, I teared up because I realized many things about myself, but also because I saw emotion and pain seep into the eyes of both the EITs and my fellow volunteers.

It was particularly moving to see when EITs and volunteers both stepped to the line after a statement was read. Seems that in some cases, volunteers had the fortune of not getting caught and had the support network to keep them from going down the wrong path. Not surprisingly, most of the inmates didn’t.

2. Inmates Aren’t Criminals.

This may be a controversial statement. But yesterday’s visit reminded me that an overwhelming majority of inmates are people who weren’t given the same kind of opportunity as the volunteers. When you grow up in poverty, suffer from abuse, live in a violent neighborhood, come from a broken home, lack positive role models, are told you’ll never amount to anything, etc, the challenges are enormous. It brings a whole new meaning to #firstworldproblems.

In 1:1 conversations with EITs, I was surprised that I felt a little embarrassed of my upbringing. More specifically, I was embarrassed because I felt like I’ve taken it for granted.

For example, one of the statements from the line exercise was “I lost my innocence at the age of [X]”. (Catherine kept ratcheting down the age to see who stayed on the line) One EIT told me he lost his innocence at the age of 5, when he was almost beaten to death by a grandparent. All my “hardships” suddenly paled in comparison. In fact, I had a tough time even answering the question of “I knew I lost my innocence when…” because none of my experiences seemed relevant.

Catherine hates pity. And I hope that’s not how this comes off. Rather, it’s to emphasize another thing she said. Inmates aren’t criminals. Inmates are people who committed crimes. They don’t want to be remembered for the worst thing they ever did in their life.

Granted, crimes aren’t necessarily something to be condoned or downplayed. Many of the inmates were convicted of murder. I’ve lost a relative to murder in an armed robbery. However, when you begin to understand the life circumstances and cards that the inmates were dealt in life, it allows you to be more compassionate and open your mind to the idea that they did a bad thing — but they’re not bad people.

The EITs didn’t want pity, nor did they want handouts. They wanted to be treated like peers and get brutally honest feedback. As the day went on, the EITs seemed less and less like inmates, and more and more like colleagues. There were no barriers separating us. We sat side by side. We shook hands. We laughed and danced together.

Inmates are sons, fathers, brothers, cousins, nephews, and friends. Like any human being, they’re not perfect.

3. Racial Inequality Is REAL.

You don’t need to visit a prison to know that racial inequality exists. There’s enough talk about it, especially in Silicon Valley, to know that there’s a diversity problem.

However, it’s a different story when you visit a prison. When you see what I saw, you’ll know it in your heart.

This too may be a charged topic. But I’ll say my piece. There is something fundamentally wrong when the overwhelming majority of the inmate population is Black and Hispanic. Again, this was something that I was aware of. Most people are. But when I saw it for myself in person (both at the Defy event and when walking on the prison grounds to/from the prison entrance), I was floored.

This isn’t limited to Solano. Almost 60% of the U.S. incarcerated population is comprised of Black and Latino prisoners. The US makes up 5% of the world population, yet holds 25% of the world’s prisoners.

As a society, we’re failing. In so many ways. Such high incarceration rates of underrepresented minorities ultimately means we’re missing out on great potential from Black and Latino communities. Yes, there’s immense talent brewing even within the most impoverished neighborhoods. Talent is universal, but opportunity is not. Never was this more clear than when I interacted with the EITs yesterday.

How do we solve this? Unfortunately the solution(s) is as multi-faceted and complex as the problem. But as my favorite quote goes, An ounce of action is worth a ton of theory. It’s encouraging to see groups like Defy actually DOING something to enact change.

4. Transformation Requires Relentless Optimism & Gratitude.

As I mentioned earlier, the day began with a few ice breakers. For example, giving each other bear hugs, repeating affirmations, performing the Chicken Dance, etc. I’ll admit I thought a few were a little corny. But looking around the room, I was amazed at how engaged the EITs were and how much respect they had for Catherine and Defy. No one was rolling their eyes or slouching in a corner. Even with small exercises, they were present.

They were eager to hear feedback on their personal statements, resumes, mock interviews, and their business proposals, and the ones I coached took the feedback to heart.

But what struck me more than their optimism? Their gratitude.

The EITs expressed so much thanks to the volunteers. I can’t tell you how many of them approached me and shook my hand, thanking me for spending the day with them — even ones I hadn’t interacted with 1:1.

Change is not easy. Defy is not an easy program to complete. But I witnessed a group of men who possessed so much optimism and gratitude that it put me to shame. Many of them already have changed, and Defy is helping them get that second chance in life. Catherine is like no other when it comes to relentless optimism and gratitude.


Volunteering one day with Defy doesn’t make me a saint. I don’t know whether I actually helped anyone in the long run. But I’m hopeful that such small acts (by a lot of individuals) ultimately have a real impact on the lives of these EITs, and in turn begins to address the complex problems that currently exist in our society. Never underestimate small acts of kindness — aka microcompassions.

For me, the entire experience was especially meaningful because I have personal connections to a couple people who are incarcerated. By helping the EITs, I felt that in some roundabout way, I was helping them. And I hope that someday, I’ll see them again on the outside.

Many thanks to the Defy team, the staff at Solano State Prison, and most of all the Defy EITs for having us yesterday.

Catherine Hoke, Founder & CEO of Defy Ventures with Defy EITs channeling tigers.

Special thanks to Andrea Barrica, Mark Saldaña, Tara Graham, Brian Wang,Aerin Lim, and Monique Woodard for reviewing this post.