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Pushing Beyond Your Comfort Zone
3 Lessons Learned from Hosting a Retreat with No Experience
Hey! Justin here, and welcome to Just Go Grind, a newsletter sharing the lessons, tactics, and stories of world-class founders! I’m switching it up today, sharing a few lessons from the founder retreat I recently hosted.
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📅 Upcoming Events
I host events to connect founders, operators, and investors every week. Here are the next ones in LA and SF:
September 7th - LA Startup Community Basketball
September 10th - LA Startup Community Coffee Meetup
October 7th - SF #TechWeek Event (Coming soon 👀 )
October 14th - Pitch and Run LA: Run Club for Startup Community LA #TechWeek
October 15th - LA #TechWeek Coffee Meetup
October 16th - LA #TechWeek (Coming soon 👀 )
All #TechWeek events will be posted in their respective calendars below:
🙏 Thank You
Before we dive in, I must give a massive shoutout to the sponsors who made the retreat last weekend possible.
Jeff Swearingen, who gave a phenomenal talk at the retreat on Saturday sharing the ins and outs of building and selling his company for $600M+, was involved in the retreat early on and I’m so grateful for his support.
Parker, the financial stack for scaling your e-commerce brand faster and more profitably, sponsored two attendees who had a great time getting to know the other founders.
Parker went through Y Combinator in 2019, has raised $150M+, and is a game-changer for e-commerce brands.
Tom Dorwart of Omaha Phoenix Capital, a founder-led investment & advisory group focusing on consumer-facing companies, and Dorwart Law, a firm whose main focus is estate planning, generously paid for one of the meals for the weekend.
Josh Womack of Womack Capital Partners, a fund focused on investing in the smallest and most misunderstood companies in the public markets, and Womack Financial, an independent and boutique investment management firm, investing across public and private markets, also paid for one of the meals this weekend, keeping our founders fed.
Thank you so much to all the sponsors! Please support them by checking out their businesses and mentioning how you found them.
Pushing Beyond Your Comfort Zone
Last weekend, I hosted a retreat in Santa Barbara for early-stage founders.
My main goal?
Help them build meaningful relationships.
It started with a friend’s text on June 7th.
I announced my new project, Village Lane, a vetted community for early-stage startup founders, a week before.
In a text exchange, my friend mentioned:
“Might be worth launching the community with a big retreat-style event, rather than the other way around.”
A week later, I was deep in the planning process.
I didn’t realize the retreat would require so much work, that I’d get my mom’s help with logistics, or that a founder who sold his company for $600M+ would be involved.
But I thought it could be impactful.
Two months later, I was still finalizing attendees and sponsors days before the retreat.
No matter.
It all came together beautifully.
We had an incredible group spend an amazing weekend at a boutique hotel I rented out completely a few blocks from downtown Santa Barbara.
From this experience, I wanted to share three quick lessons.
Just do the damn thing.
Life is filled with people talking about what they want to do but never actually doing it.
Peter Thiel has a great lesson about this:
Don’t waste time talking about what you plan to think about; instead, work through it immediately. Intellectual laziness can easily sneak up on you. If you are sitting there talking about problems you plan to solve later, there’s a good chance you are being inefficient.
Invest in building deep relationships.
We all know this is important, but knowing it and acting on it are two separate things.
You don’t get this from a 30-minute Zoom call.
During the retreat, there was a level of authenticity not displayed in daily life, tears were shed, and struggles were shared.
What does that do?
It helps you build a deeper relationship with someone.
All attendees chose to spend an extended period in an environment with like-minded people.
That extended time together does more than an extended string of coffee meetings every few months, one where you’re only ever “catching up.”
I feel closer to each attendee, and I’ve heard they scheduled additional calls with each other after the retreat.
That’s part of the magic of a retreat.
Increase your surface area of luck
I stole this idea from Sam Altman, but it’s a lesson that the entire retreat experience solidified in my mind.
Deciding to host this retreat has increased my luck and that of others.
Deciding to go forward with the retreat was just the beginning for me.
Yes, hosting the retreat brought together incredible people, but the ripple effects of that weekend can impact my entire career moving forward.
A long-term view shows how useful increasing your luck surface area can be.
Sure, I’ve already benefited short-term.
But long term?
Who knows how luck will find me as a result of the retreat?
I love that idea.
Maybe it’s the optimist in me.
But hosting that retreat will make my life better.
I’m forever grateful for that.
📚 Recent Founder Deep Dives
In the past year and a half, I’ve written dozens of deep dives on world-class founders, sharing how they built their companies. These typically take 20-30 hours to research and write. The most recent ones are below:
💰 Raising Money for Your Startup?
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If you’re raising, reply to this email and let me know what you’re building!
Best,
Justin
Founder of Just Go Grind and Village Lane
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