Konrad Waliszewski gave 250,000 customers his number. Then he listened.

Giving your personal phone number to 250,000 customers is an unusual way to preserve a quiet evening. Konrad Waliszewski did it anyway. The early users of his travel business could reach the founder himself, which made feedback remarkably easy to deliver and, presumably, rather difficult to postpone. He came away with something more useful than reassurance: evidence that travelers were changing how they searched.

People were using social media to discover places and decide where to go. Listening to them helped push his company toward social commerce. A business that began with self-guided city tours would eventually let travelers find hotel deals through Instagram. The distance between those products looks large on a pitch deck. In Waliszewski’s account, customers supplied the directions.

“I never imagined how important active listening would be,” he said. The word active matters here. He described paying attention to context and to things people left unsaid, while loosening his attachment to the answer he wanted. A founder’s phone can become a tiny referendum on his assumptions. Waliszewski had invited an electorate roughly the size of a city.

A passport before a business plan

His relationship with travel began long before there was a product to sell. Born near Detroit and raised in Nashville, he grew up as the son of Polish immigrants. His parents had been imprisoned for their involvement in Poland’s Solidarity movement and came to the United States as political refugees. Freedom of movement carried a family history.

Childhood summers took him back to Poland. By eight, he was making the international journey alone. An airport could be a passage between the places his family belonged, rather than merely the lobby for a holiday. He has described wanting to pass that curiosity and sense of possibility to his own children.

The adult itinerary became lengthy: San Francisco, Chicago, Washington, Poland, Egypt, and stretches without a fixed base. His travel writing grew around the belief that a career and an interesting life abroad could occupy the same calendar. There was practical experience behind the argument. He had worked in investment banking, consulting and startup operations while continuing to travel.

Chicago provided the weather report

One of his turning points arrived in a Chicago blizzard. He had finished three large projects and sent them off from his office. Looking at the snow after closing his computer, he wondered why work conducted with a laptop and phone required him to remain in that particular weather. Chicago had made a persuasive case for a change of address.

The incident became part of his account of choosing a more mobile working life. It also supplied a practical question: if the work could travel, how much of the existing arrangement was necessary? That question would recur in his business. Familiar ways of doing things deserved examination, especially when the person using them had quietly developed different habits.

He brought conventional financial experience to that inquiry. At GCA Savvian in San Francisco, he worked on technology mergers, acquisitions and financing. Consulting followed, including assignments for private equity firms and public companies. Those jobs involved the machinery behind businesses: transactions, strategic plans, restructurings and the work required to launch something new.

At conference-calling startup Speek, he served as chief operating officer. His responsibilities included operations, business development and fundraising, and he helped with the company’s acquisition by Jive Communications. When Speek was acquired in 2015, there was room for a project closer to his own suitcase. TripScout launched that August.

A local guide in your pocket

Waliszewski and co-founder Andy Acs built TripScout around a recognizable inconvenience. A traveler could spend hours piecing together places to visit, then arrive with a disconnected collection of tabs, tips and maps. The early app packaged local knowledge into self-guided city tours, combining audio with maps that worked offline. History, culture and food were part of the walk.

In an August 2015 interview, Waliszewski put the team at six people. Washington and Philadelphia were early destinations. Users could download the app and buy guides inside it. The company also directed part of its proceeds toward local charities. Its size was modest enough for a founder to discuss the next handful of cities rather than the next continent’s market share.

He had personally wanted this kind of tool on his travels. His explanation for entering a crowded market was correspondingly plain: make somebody’s trip substantially better. He noticed that travel was moving toward mobile devices and more local, specific experiences. A guide’s usefulness would depend on what it helped someone do once they reached the street.

By early 2016, audio guides cost $4.99 and the catalogue was expanding. Waliszewski personally vetted local guides and temporarily based himself in Egypt to help cover nearby regions. For Washington, he was the guide himself. The business had the pleasingly literal quality of a founder walking through his own product.

The holiday starts months before departure

The product’s scope widened. By April 2019, TripScout had raised a $2.1 million seed round led by Corazon Capital, including an earlier pre-seed investment rolled into the total. The plans included a stronger recommendation engine, a larger marketing team and more ways to use the service. Accommodation was already on the list of possible additions.

The underlying problem had also expanded. A traveler might want inspiration months before departure, an itinerary a few weeks out, and a recommendation around the corner after arriving. A tool limited to the days of the trip could miss most of that relationship. TripScout was moving toward giving people reasons to return between journeys.

Fundraising supplied its own itinerary. Waliszewski has recalled 219 meetings before finding a group of early believers. He kept count. The precise total gives the story some useful friction: a founder with travel experience and an actual product still had to repeat the argument until someone agreed to finance it. The meeting after the disappointing meeting was part of the job.

“My parents taught me to value freedom and mobility, and I never took it for granted.”

Konrad Waliszewski

By May 2021, the company’s podcast biography described a remote team spread across seven countries and four American states. Its Instagram network then had more than eight million followers. Remote work had become a company practice as well as a personal preference. The founder’s early question about where a laptop could function now had several national answers.

One word in a direct message

In June 2022, the hotel-booking proposition arrived with an almost absurdly short instruction: message “hotel.” A traveler could send that word to one of TripScout’s Instagram accounts and receive access to a private booking link. Partnerships with hotel inventory providers supplied the rooms. The travel pictures and the transaction were moving closer together.

At that point, the company said its network had more than 30 million followers across over 100 Instagram feeds. It had also raised roughly $10.3 million. Those were figures for that moment, rather than a count of hotel customers. A person watching a video and a person paying for a room occupy different columns in the business.

The commercial idea was to make the audience useful when a viewer became ready to book. Private rates gave people a reason to move from looking to checking availability. The approach also put the company in a different position from a startup buying search advertisements against established booking businesses. It had been building places where travelers already spent time.

In 2024, Waliszewski announced a partnership with Hopper to support a new booking platform. He described combining @hotel’s social reach with Hopper’s technology and hotel contracts. Attention alone could take the business only so far: travelers still needed prices, availability and a booking process that worked when they wanted to leave.

Somebody still has to answer

The human conversation remained part of the offer. A DM Concierge service described in February 2024 provided personalized recommendations, while the company’s Traveler Care team offered assistance across messaging and other channels. Finding a hotel for a family with particular requirements can require more than an attractive room photograph and a search filter.

Waliszewski’s public advice on social platforms has a similarly practical streak. He says his team tries new platforms early, stays curious and waits for evidence before committing heavily. That is a useful distinction in a business constantly offered new places to post. The experiment can be quick; the investment should have a reason.

His ambitions now extend beyond selling accommodation. In a tenth-anniversary announcement, he introduced The Explore Network, bringing destination marketing, @hotel, consumer brands and entertainment under an umbrella. The announcement described relationships with more than 50 destinations and an audience approaching 100 million followers across its brands. These are the company’s reported network figures, rather than a measure of unique travelers.

The responsibility behind the feed

A publishing network also has obligations to the people making its images. In September 2026, Tripscout’s copyright dispute with creator Asa Steinars remained headed toward a jury after a federal judge granted parts of each side’s summary judgment motions. The dispute concerned the company’s reposting of her work. Questions including damages and willfulness remained for trial; the ruling did not establish personal liability for Waliszewski.

That unfinished case belongs alongside the growth story. A company built around discovery depends on relationships with creators as well as travelers. The scale of its distribution makes permission and internal oversight consequential. It adds a harder operational question to the early promise of helping people find something worth seeing.

Waliszewski’s career keeps returning to the space between a plan and the person trying to use it. The child traveling to Poland became the operator traveling with a laptop, then the founder trying to put a useful local voice on a phone. Eventually, he put his own number there too. For a business that wants people to go somewhere, being reachable was an unusually revealing place to begin.