Zero to $80M in 4 years with John Andrew Entwistle of Wander

Hey, Justin here, and welcome to Just Go Grind, a newsletter sharing the lessons, tactics, and stories of world-class founders! Premium subscribers get full access to this newsletter, exclusive events, event discounts, and more.

John Andrew Entwistle is the founder of Wander, a company rewriting the narrative of travel through elegance, technology, and intentional design.

He built his first company at the age of 13. And by the time he was 16, he built Coder.com—an idea born in high school, later backed by Silicon Valley's most storied venture firms.

At 23 he was already a CEO and had raised over 50 million dollars. But he got a different vision, something he was more passionate and excited about, and went all in to build Wander.

Now, at only 27, John Andrew is one of Forbes’ 30 under 30 and has grown Wander into one of the defining forces in the American travel landscape.

Listen to John Andrew’s interview on YouTube, Spotify, or Apple Podcasts.

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• Success in startups requires strategy, not just passion. John Andrew emphasizes that starting a company is a major life commitment, which inevitably comes with a high likelihood of failure. Founders must be deeply thoughtful, strategic, and deliberate in choosing their idea and executing on it. To wing it may be thrilling, but it isn't a reliable path to success.

• No one is coming to save you. Sounds ominous, but it’s actually a good thing. A recurring theme is radical responsibility: the mindset of "no one is coming to save us" instills a strong sense of agency, pushing founders to act decisively and build their company proactively without waiting for external help or validation.

• Work backwards. John Andrew created a "pre-mortem" document to anticipate failure points and systematically test Wander’s business model before building. He even tested real customer demand early by charging users for early access—generating hundreds of thousands in revenue pre-launch—highlighting the value of testing market fit before scaling.

• Start Unscalable to Validate the Vision. In the early days, John Andrew personally drove around to scout homes and oversaw cleaning, tech integration, and customer experience. This scrappy, hands-on approach let them validate that customers would actually pay for the product, even before scaling.

• Extreme Customer Experience First, Then Scale. Wander launched with a highly luxurious, tech-integrated offering (e.g., app-controlled homes, Teslas in garages, concierge services) to set a bold standard and validate demand. Over time, they refined and scaled back the experience while preserving customer delight and maintaining a high NPS.

• Branding as a Foundational Strategy. The Wander brand was designed deliberately to evoke emotion and aspiration. To John Andrew, a strong brand is a promise to the customer, and that everything from the name, logo, and even magical touches like moving backgrounds on the website should reflect that.

• Wander OS and Scaling with Software + AI. To scale such a capital and labor-intensive business, they built Wander OS—a software system to coordinate logistics like cleaning and guest communications. Now 100% of tasks are run through the system, with 60% handled autonomously via AI, enabling unusually high margins (70%+) and fast growth.

• Fundraising Is Milestone-Driven and Intensely Demanding. Each funding stage—pre-seed to Series C—requires founders to hit increasingly complex proof points, from product development and early revenue to scalable unit economics and growth. Wander is currently at Series B, which John Andrew describes as the most grueling, demanding both execution and speed, often at the cost of sleep and personal bandwidth.

• Scale Requires Growth, But Don’t Underestimate User Activation. John Andrew encourages founders to switch focus from just acquiring users to activating them, which is so much more powerful. Wander’s journey involved scaling its property supply through REITs and now turning attention to converting its large user base through personalized outreach and data-driven engagement, not just ads.

Listen to John Andrew’s interview on YouTube, Spotify, or Apple Podcasts.

00:00 What’s coming in the episode…

00:52 Introduction

02:49 John Andrew’s beginnings

04:08 Early lessons as a founder

08:19 The start of Wonder

16:35 The story behind Coder.com 

20:00 Wander’s early days

25:08 Building Wander’s brand

30:40 First customers and feedback

36:29 Locations and international expansion

42:03 John Andrew’s purpose

46:04 Funding Wander

50:51 Where is Wander today?

55:12 Focusing on user activation

1:02:41 What’s next for Wander?

I’m starting something new.

It’s a free local newsletter called The LA Grind.

It’ll include curated events and standout stories from LA’s founders, builders, and investors.

In the next week or two I’ll send out the first edition.

Sign up for free here if interested.

Best,
Justin

Founder of Just Go Grind

P.S. Hiring? Check out the team at Athyna