500 Global Founders Retreat

Q. How did you attend the 500 Global Founders Retreat if you’re not a 500 portfolio company?

Originally, this program started as a workshop for 500’s portfolio companies. However, in this recent event, companies recommended by organizations such as Smilegate Investment, Asan Nanum Foundation, and the Global Startup Academy were also invited to participate. We got our spot thanks to a recommendation from Smilegate Investment. Before going, at an orientation from 500, someone said something that really stuck with me:

“During your time here, we’ll consider you part of our portfolio and do our best to help you. We hope everyone can hang out, not just as investors and startups. You can completely let go—go ahead and dye your hair pink if you want.”

In the current tough investment scene, I’d never heard such welcoming words from someone who isn’t even our own investor.

Q. Roughly, what did the overall program look like?

From November 5 to 14, it ran for ten days. There was a weekend in between, but the weekend was left free (Day OFF) so participants could catch up on work or rest. On the other days, sessions ran from morning till evening. I don’t know if it was intentional, but the program felt like it was split into two major themes: In the first week, sessions mostly focused on explosive startup growth, while the second week covered wellness for creating a sustainable startup. Initially, I wasn’t sure whether the second week’s material would be relevant to me, but by the end, I realized that if only one of those two themes had been covered, the core values of the program wouldn’t have come through. The second week turned out to be extremely valuable.

Q. Were accommodation or flights covered?

No, each company had to book and pay for its own lodging and airfare. That meant everyone flew in on different flights and stayed in different places. In our case, a founder we knew generously lent us a house, so we didn’t have to worry about accommodations. Most sessions were held near Palo Alto, while our lodging was in San Francisco, so we spent two hours commuting by rental car every day (infinite thanks to our best driver, Youngbeom!). We did consider Uber, but it was too expensive, so we decided to rent a car. In the beginning, the thought of commuting for so long made me nervous. But as they say, life can be unexpected in a good way: we used the large SUV we rented to carpool with other founders who lived nearby and ended up forming strong friendships during our daily rides. Meeting them turned out to be one of our biggest strokes of luck on this trip.

Q. Can you share more about the daily schedule?

Day 0 (Nov 4): Arrived in San Francisco.

Day 1 (Nov 5): Session with Sol Eun, founder of Vertical Bar (previously exited a YC startup). After that, there were 1:1 “Deep Dive” sessions with each company. The most memorable moment was talking to our session lead, Sean, who asked probing questions that highlighted how to communicate so that people on the other side would genuinely want to listen and respond. Even though our company has been incorporated for four years, it felt like we were learning all over again how to talk about who we are and what we do from scratch.

Day 2 (Nov 6): In the morning, Andrew and Kris from Darwinian Ventures talked about B2B sales and digital marketing. Their practical advice was good, but two quotes stood out for me:

“If you don’t define yourself, others will do it for you.”
“Every choice you make in life either builds trust or breaks it.”

The most memorable part of the day was the Founders Forum in the late afternoon. Initially, I didn’t know what it would involve. We split into three groups, drew personal “life graphs,” and shared our life stories. I wondered how honest everyone could be in a business-like setting, but thanks to a rule of “whatever is said here, stays here,” everyone spoke quite frankly, and others listened quietly. This session turned us from mere acquaintances on a business trip into genuine friends, open with one another.

Day 3 (Nov 7): In the morning, Peter from 500 Korea (founder of Querypie, YC W20) explained how to analyze the broader startup market, highlighting common mistakes many startups make. Then came a session from Jina Kim, who handled CS/X at companies like Amazon and Apple, and a session from Kyong Han on the mindset and attributes of successful startups. After lunch, we heard from Chuck (ex-U.S. Navy special forces and now a founder) and from Marcelo, cofounder of Remote. That evening, there was a Winter Mixture networking party by 500 Japan, which we didn’t attend.

Day 4 (Nov 8): In the morning, we visited the headquarters of Carta (sort of like Korea’s QuotaBook). In the afternoon, we joined a networking event at Google’s San Francisco office.

Day 5 (Nov 9): Day OFF. We’d been surviving on 2-3 hours of sleep for four days, so we finally caught up on rest.

Day 6 (Nov 10): Day OFF. Had a lunch coffee chat with Se-young Lee, CEO of WRTN.

Day 7 (Nov 11, Veterans Day): Went hiking in Huddart Park. Afterwards, the 500 Korea team invited us to their Airbnb, where we shared dinner and wine.

Day 8 (Nov 12): Visited Notion’s HQ for a session. Surprisingly, the office was in a warehouse-like area that gave off a vibe akin to a renovated warehouse-cafe in Seoul’s Seongsu district. (Short Notion video) Then we headed to Stripe, had lunch at the Stripe cafeteria (Tuesday is taco day—really fresh and tasty). We had time to tour the office before the next session. Stripe’s office was one of the most creative workspaces I’ve seen. (Short Stripe office video)

Day 9 (Nov 13): For two days, sessions were held in a stunning three-story cabin in the Woodsides forest. The first session was “Start Up Yourself” by Miru Kim, who worked at Apple, MS, and Meta, and recently launched a wellness coaching startup. In the afternoon, there was a Final Graduation IR Pitch Contest with Silicon Valley investors, and among many strong contenders, we (Walla) placed 2nd!

Day 10 (Nov 14): From morning until evening, we attended sessions led by coach Jenny Huang on mental training and emotional resilience. That evening, everything wrapped up with a Farewell Dinner.

Q. What did you gain from this experience?

This retreat was literally a chance to “retreat”—to step back and reflect on how far we’ve come. During entrepreneurship, what you need most and seldom find is the space to pause and see the bigger picture. In the startup world, we’re typically convinced we must have unwavering faith in our product and constantly try to persuade customers and investors. Many startup workshops support that mindset by telling you “You’re doing great! Keep pushing forward!”—which provides a needed boost of courage. But here, it was different. Instead of reassuring us, they asked, “Are you really on the right path? Maybe it’s time to rethink from the very beginning.” They even taught us to breathe, to pitch our product from scratch, to reintroduce our company—stuff we thought we already knew well. Doubt can eat away at you, but this type of guiding push, rooted in trust, helped us rediscover what we’d been missing and come back to deliver two or three times our normal performance.

Q. Any final words?

It’s not a one-size-fits-all program for every sector and every stage. However, for my cofounder and me, each 10-minute break between sessions sparked a flood of new insights that led us to excitedly imagine our future. Despite the extreme schedule and lack of sleep, the sessions left a lasting impression. Spending time with people other than our own team let me rediscover my personal strengths, warmth, and an endless capacity for gleaning insights. If you’ve read this far, I hope you’ll find the same kind of luck at your next retreat.