- Deal Lift
- Posts
- From Friend-Trips to Full-Blown Travel Brand: The WeRoad Founder Playbook
From Friend-Trips to Full-Blown Travel Brand: The WeRoad Founder Playbook
How Paolo De Nadai, Erika De Santi & Fabio Bin transformed their own travel frustrations into a community-first, adventure-travel business hitting €100 M in revenue and scaling fast across Europe
👋 Hey Deal Lift Readers
If you’ve been thinking: “There’s too much travel tech already,” then this story of WeRoad might flip your mindset. Founded by three friends who hated trying to organize trips with other grown-ups, WeRoad has gone from small group adventures to a major travel tech business that hit €100 million revenue in 2024.
In this issue I’m pulling apart the founder story, the tactics, the growth levers — so you can steal what applies. Expect some emojis, some flair, and a lot of value. Let’s go.
Find customers on Roku this holiday season
Now through the end of the year is prime streaming time on Roku, with viewers spending 3.5 hours each day streaming content and shopping online. Roku Ads Manager simplifies campaign setup, lets you segment audiences, and provides real-time reporting. And, you can test creative variants and run shoppable ads to drive purchases directly on-screen.
Bonus: we’re gifting you $5K in ad credits when you spend your first $5K on Roku Ads Manager. Just sign up and use code GET5K. Terms apply.
🧠 The Spark: Frustrated Travelers Build Their Own Solution
Meet the founders:
Paolo De Nadai
Erika De Santi
Fabio Bin

They loved travel. But as they got older? Trying to coordinate trips with friends who had new jobs, relationships, homes — it was complicated. They tried group tours for solo travelers, but found them off-brand: lacked authenticity, social connection, the “right crowd”.
So they asked: What if we built a travel company for people like us — curated trips, social by design, matching moods not just destination? That insight became WeRoad.
Key play: Realizing your own pain is probably shared. Build for it.
🏗️ Execution Timeline: Launch → Crisis → Scale
Year | Milestone | Impact |
|---|---|---|
2018 | WeRoad launches. Seed funding ~$2.34 M in July. | Kitchen-table startup, relatable founders. |
2020 | COVID hits. Travel stops. Community raises €750K through gift-cards in 3 days to keep team on payroll. | Crisis = authenticity & trust. |
2021 | October: Raise €13.5 M (equity + convertible + debt) including €4 M from crowd-investing. | Capital for expansion. |
2022 | April: Hire Andrea D'Amico (ex-Booking.com) as CEO to scale internationally. | Professionalisation + growth ops. |
2023 | November: Secure €18 M Series B. | Growth engine engaged. |
2024 | Launch weRoad.com international platform. End year with €100 M revenue (≈ 70% growth). | Proof of scale + product-market fit in travel. |
2025 | Launch “WeMeet” in-person community events in 30+ European cities; aim to lead adventure travel in Europe. | Community → brand → scale. |
🔍 Why WeRoad Works: Four Key Levers
1. Community First
WeRoad didn’t build a travel agency—they built a tribe. Solo travelers, small groups, shared vibes. 600+ trip coordinators, mood-based matching, peer community. Unlike commoditised tours.
2. Audience-Focused Design
They targeted Millennials & Gen Z solo-travelers who still crave connection. Their trips are curated by age‐group & interest (“adrenaline”, “culture”, “chill”). That segmentation leads to better NPS, higher referrals.
3. Tech-Enabled, Not Tech-Overboard
They resisted making a “Tinder for travel” with algorithmic matching. Instead: personal coordinators + community chats + human-first tech. That balance kept authenticity.
4. Crisis Reinforces Brand
When COVID shut travel globally, WeRoad didn’t hide. They were transparent, asked their community for help via gift-cards, raised in 3 days. That built brand trust that now fuels referrals and retention.
📊 Tactical Breakdown: What Operators Should Steal
Define your “mood” segment: Instead of generic product, slice by user-state (e.g., “I just got divorced and want connection”, “I’m 30 and free and want adrenaline”, etc.).
Create lead with community: Before 100 M revenue hit, WeRoad had a community of travelers and coordinators. That organic growth matters more than paid ads.
Use crises as bonding moments: Community loyalty is built when you’re real during turbulence.
Human-first tech: People don’t always want full automation—especially with experience products.
Expand when ready: WeRoad launched globally after they nailed the core model in Italy & Spain. Don’t scale too early.
🧩 Additional Insights Worth Noting
WeRoad raised €13.5 M in Oct 2021 including €4 M via crowd-investing from ~100 customers. That means community-investors = brand ambassadors.
They currently operate across major European cities, with presence in Italy, Spain, UK and more.
Their business model includes: tours direct to traveler + merchandise + sponsorships + community meets. That diversified revenue helps weather travel seasonality.
In 2024, the revenue figure of €100 M indicates travel market now tolerates niche, community-driven operators—not just big tour brands.
🎯 Final Thoughts: Why This Story Matters to You
If you’re building a business in 2025: maybe you’re in experience, services, community, travel—or something seemingly crowded. WeRoad’s playbook says:
Find the social gap in your market. People want connection, not just product.
Build community before scale.
Be transparent when things break. Real brand = real human story.
Design for mood, not just demographics.
Use tech to enable, not replace, human relatability.
✅ Deal Lift Takeaways
Title: The WeRoad Growth Framework: Community → Experience → Scale
Key Moves to Apply:
Own the mood-match (segment by state of mind).
Launch with human-first model (coordinators, community).
Make your crisis-response part of brand building.
Diversify your revenue streams within your vertical.
Raise growth capital only after core model is proven.
Crash Expert: “This Looks Like 1929” → 70,000 Hedging Here
Mark Spitznagel, who made $1B in a single day during the 2015 flash crash, warns markets are mimicking 1929. Yeah, just another oracle spouting gloom and doom, right?
Vanguard and Goldman Sachs forecast just 5% and 3% annual S&P returns respectively for the next decade (2024-2034).
Bonds? Not much better.
Enough warning signals—what’s something investors can actually do to diversify this week?
Almost no one knows this, but postwar and contemporary art appreciated 11.2% annually with near-zero correlation to equities from 1995–2024, according to Masterworks Data.
And sure… billionaires like Bezos and Gates can make headlines at auction, but what about the rest of us?
Masterworks makes it possible to invest in legendary artworks by Banksy, Basquiat, Picasso, and more – without spending millions.
23 exits. Net annualized returns like 17.6%, 17.8%, and 21.5%. $1.2 billion invested.
Shares in new offerings can sell quickly but…
*Past performance is not indicative of future returns. Important Reg A disclosures: masterworks.com/cd.
If you liked this issue, I can send you the “WeRoad Playbook PDF”—10 slides you can use for your startup growth deck, including community growth checklist, mood-segmentation map, revenue stream matrix. Just reply “Send PDF” and I’ll drop it in your inbox.
Thanks for reading Deal Lift.
Here’s to building brands that scale by meaningfully connecting people.
— Deal Lift


