$50M Wander Series B & Dinner Wisdom with David Phillips
“Candidly speaking, Wander is my soul, but as a company”
John Andrew and the Wander team just closed a $50M Series B, co-led by Fifth Wall and QED Investors.
Another big win for solo founders — congrats, John Andrew and team!
What’s Wander?
Think Airbnb-style vacation homes with the consistent quality and reliability of a luxury hotel chain.
Want the full story? (All published last week)
- Not Boring — “Wander: Deeper Dive” with Packy McCormick
- “There are about 300,000 homes that are Wander-worthy. Globally, that represents about $35 billion of GMV.”
- Sourcery Podcast — “How Wander Raised $50M to Reinvent Luxury Travel” with Molly O’Shea
- “Tomorrow is a lazy man's today. If you want to live a fulfilling life, you can't delay things — you should try and get it done now.”
- TBPN Interview — John Andrew’s founder journey
“Test-drive” contributors instead of giving away half the company on day one.
Solo Founder Playbook — David Phillips Edition
David Phillips is a three-time founder and YC alum who discovered the cost of co-founder misalignment. In his previous startups, he experienced the full spectrum of co-founder breakups — from being fired, to parting ways amicably, to making the tough call to let a co-founder go. Determined to build on his own terms, David launched Fondo to put bookkeeping, taxes, and tax credits on autopilot.
David joined us for dinner at the SFP house and shared some amazing insights with the cohort. Below are the three biggest lessons, expanded with the back story that makes each one stick:
1. Own the vision first—then add support on your terms.
David stressed that being a solo founder let him move fast and dodge 50/50 deadlocks. He built early traction alone, then “test-drove” helpers for significant (but not co-founder) equity instead of giving away half the company.
Why it matters:
- One clear tiebreaker. Decisions don’t stall when there’s only one final say.
- Equity stays flexible. You can reward contributors without locking into a co-founder split.
- Momentum attracts talent. Once the idea shows signs of life, it’s easier to recruit believers — even on deferred pay.
2. Lead with real value, then earn the right to pitch.
Early on, David offered to file Delaware franchise taxes for free. Roughly 10 out of the first 100 grateful founders converted to paying bookkeeping customers.
Why it matters:
- Hair-on-fire problem first. Filing late triggers a $500 penalty — easy to grasp and urgent to fix.
- Instant trust. Delivering a concrete, time-sensitive win shows competence faster than any sales deck.
- Built-in social proof. Every public “thank-you” comment on YC’s Bookface acted like a mini-testimonial, seeding the next wave of sign-ups.
3. Retention is growth — because word-of-mouth has a CAC of $0.
David measures success by user love — delighted customers bring in the next ones for free.
Why it matters:
- Metric that compounds. Every 5-star founder tweet about Fondo became a warm intro pipeline the marketing budget could never buy.
- Investor signal. Low churn + high NPS told VCs the business could scale without marketing burn.
- Focus filter. When resources were thin, David prioritized features that kept existing clients longer over flashy new lead magnets.
Thanks again, David, for being part of Solo Founders and sharing your experiences with the Program and this newsletter!
While this isn’t a sponsored post, we’re still happy to include a little Fondo promo 🙂 — if you need help with tax deadlines, bookkeeping, or want cash back from the IRS in tax credits, check out Fondo. They’re used by great companies like PostHog and ElevenLabs.
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— Julian, Kieran, and the SFP team
