Jason Kirby: Welcome back to the show, everyone. Today we have Wen-Wen Lam with us, former founder of NexTravel and current partner at Gradient Ventures. Welcome to the show.

Wen-Wen Lam: Hi, nice to see everyone.

Jason Kirby: I’m grateful to have you on the show. Our preliminary discussion was already super interesting. To kick things off: tell us about your background, what led you to founding NexTravel, what happened there, and how that led you into VC.

Wen-Wen Lam: I’ve basically always been in tech. Right out of college, when everyone was doing banking or consulting, I wanted to work at a social network—specifically MySpace. I applied to all the networks (not Facebook—great call in 2005!). Through LinkedIn I got a job at LinkedIn, started in product, and they immediately handed me LinkedIn for Groups. I was effectively a PM right out of school and part of the initial sales motion that brought in the first dollars for premium and recruiter offerings.

Wen-Wen Lam: After that I went to USC for business school, worked at a few startups, and then with the MySpace founders at Slingshot Labs. Later, Singaporean investors recruited me to co-found a Southeast Asia startup—basically an Airbnb clone. We had $1M to start (a lot then, pre-seed today). It didn’t work out—the founding team was cobbled together—but it set the stage for NexTravel.

Wen-Wen Lam: I love travel and initially started on the consumer side—everything after flights and hotels. Like many, we pivoted. My LinkedIn experience made selling to businesses natural, and we needed something people would pay for. We moved to corporate travel and started getting customers even before launch—Birchbox shared their pain points; we partnered with a company called YAC. There was clearly demand.

Jason Kirby: So you went from LinkedIn to several startups, then founded NexTravel. How big did you get? Did you raise money, and what was that journey like?

Wen-Wen Lam: We didn’t raise much but got pretty big. Pre‑pandemic we were around $100M in top-line bookings—roughly $7–8M revenue with travel margins being thin. A key unlock was partnering early with Expensify, which meant we didn’t need to spend heavily on customer acquisition.

Wen-Wen Lam: Post-pivot, I applied to YC on a whim—friends pushed me, I knew Justin Kan. Interview slates included Sam Altman, Jessica Livingston, then Justin, Garry, and Kat. Justin called me and said, “You’re an idiot if you don’t do this,” and hung up. Joining YC was our best decision.

Wen-Wen Lam: Early on, licensing slowed us—we had to wait for an agency to issue tickets—so we built product with batchmates while we waited. We co-built around Platzi (big LATAM education company) who traveled constantly. That led to a best‑in‑class SMB product. We discovered even 20–30 person firms needed corporate travel tools: central cards, no fronting expenses, clearer finance controls.

Wen-Wen Lam: Soon after YC, Expensify reached out wanting to compete with Concur, and we partnered. Even as a small company we served names like Lyft and Twilio while they scaled—lots of “fake it till you make it.”

Jason Kirby: Incredible ramp—pivot to monetization and real customers. What happened when COVID hit?

Wen-Wen Lam: It was brutal. Because of Expensify, we’d raised far less than competitors like TripActions (now Navan) and TravelPerk (who ultimately acquired us). We’d raised about $4.5M over four years. Pre‑COVID we were already having acquisition conversations with large public companies.

Wen-Wen Lam: When COVID hit, we went from ~$10M in monthly bookings to basically zero, then ~$500k a few months later. I did a small layoff first—hoping travel would rebound quickly—but the second wave made it clear we needed to sell. I built a comprehensive buyer list and ran a full process.

Wen-Wen Lam: TravelPerk wasn’t even on my first list (European HQ), but as the process unfolded, they leaned in. My pitch to their CEO Avi was: “This is the time to roll up travel agencies. You’re great at raising money; use the acquisition as a wedge.” They bought us, expanded into the U.S., and rapidly raised at higher valuations. The lesson: train yourself to look for opportunity in downturns—even if it means someone else executes the roll‑up you envisioned.

Wen-Wen Lam: Psychologically, my mindset was: this has to get done. Maybe I make little; investors will get something; but the job is to create a positive outcome. That framework helps founders I coach who are selling now.

Jason Kirby: Let’s unpack “running a process.” How did you learn what to do and execute it?

Wen-Wen Lam: A friend, Pete Van Dorin, told me to read The Magic Box Paradigm—and to follow the process. I recommend it to every founder contemplating a sale. There are different paths: a strategic sale (positioned around tech, team, revenue, or roadmap leverage) and a distressed sale. For a strategic sale, map why buyers would want you and cultivate those reasons early (talk to product leaders; build what big orgs can’t get done).

Wen-Wen Lam: If you must sell, set a firm timeline. Bucket every possible buyer: needs AI/eng talent, needs ops capability, wants your product, etc. Then pitch each with a tailored narrative. Your initial goal is one LOI—it catalyzes others, especially competitors. I’ve seen AcqHires turn into $10–20M outcomes once a rival fears losing the team.

Jason Kirby: 100%—we did something similar at LiquidSky after a deal collapsed. Commit to selling; don’t sit for 12 months. There’s also founder opportunity cost.

Wen-Wen Lam: Exactly. And remember: many first-time founders hit big on company #2. Getting a deal across the line is incredibly hard—data rooms, diligence, stress. But it demonstrates perseverance and execution under pressure.

Jason Kirby: Moving to VC: how did that happen, and what do you focus on?

Wen-Wen Lam: I accidentally became a VC. My first investor (now a partner at Gradient) called me in the middle of our process. After we closed, I joined Gradient in 2021 and had to learn the craft beyond angel “YOLO” investing—ICs, process, portfolio work. One thing that helped: at NexTravel we used ML extensively in customer support—we were ~50% more efficient than typical agencies with higher NPS, so I had practical AI experience.

Wen-Wen Lam: At Gradient, we focus on infrastructure, future of work, and consumer. I gravitate to consumer. Infra is crowded and commoditizing; future-of-work tools often aren’t defensible when they all sit on the same base models. In consumer, brand + product + social graph still matter—and big companies often don’t win natively (think YouTube’s origin).

Wen-Wen Lam: My current themes: (1) chatbots; (2) creator economy; (3) social. On chatbots: younger users increasingly prefer them—even for therapy-like use. Trust & safety is critical. Corporate chatbots are mixed; consumer engagement is real (e.g., Character AI).

Wen-Wen Lam: Creator economy is my favorite: AI lets anyone make novels, scripts, short videos, animations. I recently announced an investment in Jars—tools for manipulating animated characters and generating funny, vice‑style content with strong trust & safety. I also cold‑source when something intrigues me (e.g., Infinity AI). Sometimes the best deal in the room is the friend of the founder pitching.

Jason Kirby: Any closing thoughts for founders?

Wen-Wen Lam: If you’re struggling to find PMF, consider building to get bought—solve something specific that a bigger company can’t ship quickly. If you need to sell, set a date and run the process. And don’t underestimate what you’ll do on your second company.

Jason Kirby: Wen-Wen, this was awesome—thanks for sharing your journey from operator to investor.

Wen-Wen Lam: Thanks for having me!