Planning a trip to a college campus, concert or Northwest landmark? Portland startup HitchPiggy is betting the ride you need may already be headed out on the road.
The company’s new marketplace allows drivers to post trips they’re already planning and connect with passengers heading the same way. Unlike on-demand services such as Uber or Lyft, HitchPiggy is focusing on regional travel, allowing drivers to choose who rides with them and what passengers contribute toward the trip.
Founder Skylar Windham says the idea has been percolating in his head for years, sparked from experiences traveling through Europe. Only recently, AI-powered coding tools allowed him to build the platform he always imagined.
The bootstrapped startup is small, with a little more than 100 registered users signing up for Pacific Northwest trips since its launch on June 1. No rides have been completed through the platform just yet, but Windham is looking to grow college ridership this fall through a partnership with the Portland State Business Accelerator.
Arsh Haque, director of the Portland State Business Accelerator, said he loves startup ideas like HitchPiggy that are hatched from international experiences.
“I got to firsthand experience a solution like HitchPiggy abroad, have always wanted it in the U.S., and think Skylar has the raw talent to bring it here,” said Haque.
Windham — a therapist and sailboat instructor by training — believes the service is on the right course as it tackles the complex challenge of matching drivers and riders. In fact, Windham’s background as a certified counselor and sailor is proving to be a useful in getting HitchPiggy on the road.
Counseling has honed listening skills, while sailing has taught adaptability.
“When you’re trying to reach a destination and the conditions change, you have to stay calm and adjust your course without losing sight of where you’re going,” Windham tells GeekWire. “That applies to building a startup too.” Let’s meet our latest Startup Spotlight company: HitchPiggy.
In 50 words or less, give us your elevator pitch.
HitchPiggy is like Airbnb for the empty seats in your car. It helps drivers already traveling between cities connect with passengers heading the same way, making travel more affordable and putting existing empty seats to better use.
What problem are you obsessed with solving?
There are already thousands of empty seats traveling between cities every day. I want to help drivers and passengers fill them instead of letting them go to waste.
What surprised you after talking to customers?
I’ve been pleasantly surprised by how encouraging and helpful people have been. Even when there’s been a hiccup, users have been patient and supportive. I think HitchPiggy naturally attracts community-minded people who genuinely want to help each other.
How has AI changed the way you build your company?
I first tried building this idea in 2016 by hiring engineers overseas, but getting the product right was difficult. Eventually, I put the project on the back burner. Today’s AI tools gave me the ability to finally build the platform I had envisioned, despite having no coding background.
What’s one thing people misunderstand about your startup?
Many people assume HitchPiggy is like Uber or Lyft. It isn’t. It’s a community-based rideshare platform for intercity travel, not local, on-demand rides.
Another common misconception is that the idea itself is unusually risky. In reality, people have been sharing rides for years through Craigslist, Facebook groups, and word of mouth. HitchPiggy makes that process more transparent and easier to use. It won’t be for everyone, and that’s okay. But for people who already like the idea of sharing rides, I think it’s a much better option than what has existed before.
What about safety?
Like any platform that connects people online, there is some inherent risk, and HitchPiggy can’t eliminate that entirely. What the platform can do is help people feel more informed and comfortable before deciding to ride together. Users can see details about who they may be traveling with, the vehicle, pickup location, route, timing, cost, and other important trip information. They can also message each other beforehand and ask any questions they need.
What’s the toughest decision you’ve made in the past year?
The toughest decision I’ve made was deciding not to pursue investors, at least not yet. There’s a lot of pressure in the startup world to raise money and grow as quickly as possible, but I wanted to build HitchPiggy differently. I’d rather grow steadily and learn from real users before trying to scale. It hasn’t been the fastest path, but it has felt like the right one.
What’s the one piece of advice you give to other entrepreneurs?
Have thick skin. Most feedback will be positive, but there will always be people who are quick to tell you why your idea won’t work. Anything worth building comes with challenges. Focus on what’s possible instead of everything that could go wrong. If entrepreneurs listened too closely to every critic, very little would ever get built.
We’ll know our company has made it when…
It’s a household name and people naturally check HitchPiggy before looking for a bus or train ticket whenever they’re traveling between cities.
