Endeavor talks with Valerio Chiaronzi and Graziano Cavallo (Co-founders hlpy)
Welcome back to Endeavor Talks With…!
This time we’re excited to sit down with Valerio Chiaronzi (Co-founder & CEO) and Graziano Cavallo (Co-founder & Managing Director Italy) of hlpy, the company transforming the world of vehicle assistance through a cutting-edge digital platform and real-time support.
hlpy delivers seamless roadside help, repair, and maintenance services — fully digitalized, from emergency interventions to EV charging and full-service repairs — boosting efficiency for both drivers and business clients, while optimizing the entire supply chain.
Happy reading!
First, Tell us about yourself. Who are you?
Valerio: I come from a sociology and humanities background but moved early into new media and startups in the 2000s, including one that went public. After time at British Telecom and consulting, I spent 14 years at Europ Assistance, focusing on vehicle assistance, and later became Deputy General Manager at AmTrust. But entrepreneurship was always on my mind -and in 2020, together with Graziano, we launched a challenger in the mobility space.
Graziano: I have a business background from Bocconi and started at Ducati, then joined Europ Assistance in 2004, where I worked alongside Valerio for years, eventually leading marketing. After a jump into hospitality with NH Hotel Group, I reconnected with Valerio at AmTrust. By 2020, we were ready to turn our long-time idea into an entrepreneurial venture.
After more than ten years in senior management, when did you realize it was the right moment to launch your own entrepreneurial project?
Valerio: Covid was a big catalyst -it pushed us to rethink the industry and gave us the drive to act on the experience we’d built over the years. We saw a clear market need to modernize and reinvent a space still tied to old models, and that gave us the confidence to start designing and building the company.
Graziano: For me, it was also a personal turning point -reflecting on whether corporate life was still the right path. Those long lockdown nights working on the project made it clear this wasn’t just a good idea on paper, but something that could truly work. That realization pushed us to take the leap.
You went international right from the start – why make that choice so early on?
Valerio: That question really gets to the heart of our market -roadside assistance and vehicle services -which is all about volume. It’s not just about margins; volume gives you leverage with rescue networks and makes you relevant to business partners. Many of them, like rental, leasing, OEMs, insurers, run international tenders and expect partners to operate across markets. For us, going abroad was never really up for debate -from day one, we knew scale was essential. As soon as we saw the model worked in Italy, we expanded, launching in France almost immediately.
You recently entered the German market through an acquisition. What were the main challenges you faced?
Valerio: Germany is a key market for automotive, but its structure made organic growth slower than what we’d experienced in France or Spain. So when the opportunity for M&A came up, it felt like the right move. We found a good fit with MySchleppApp -they were also at a crossroads -and that alignment helped accelerate the deal. It was intense: a full year of work, alongside a funding round, so we learned a lot -from investor management to integration planning.
Graziano: For me, the cultural aspect was key. From day one, we built a relationship of mutual trust with the German team, which made a big difference throughout the ups and downs of the deal. What helped was being clear from the start: they would fully join the hlpi project -brand, tech, everything. That transparency, combined with genuine alignment, made the integration smoother and more meaningful in the long run.
In your view, what defines a successful entrepreneur today?
Graziano: For me, success comes from staying true to your original vision. Sure, it takes courage -but less than people think when your idea is strong and genuine. The real challenge is discipline: not getting distracted by tempting side opportunities that pull you off course. Success often comes down to doing what you set out to do, just 5% better than your competitors.
Valerio: I’d add the human side: the energy and mindset. As an entrepreneur, you have to know how to reinvent yourself every day -no two days or challenges are the same. It’s not about handling exceptions; it’s about making constant reinvention your routine. That internal drive and self-renewal become essential, because at the end of the day, no one else can generate that momentum for you.
What’s your relationship with mistakes? How do you approach error and learning?
Valerio: Coming from 20 years in corporate gave us a big advantage: we’d already made -and learned from -many of the mistakes young founders face. We carry those scars, but we earned them earlier, inside big companies. Some mistakes are universal, whether you’re in a corporate or a startup, but thanks to that experience, we can avoid a lot of the typical early-stage pitfalls and bring a stronger managerial foundation, even in how we work with investors.
It’s often said that for a founder, the company becomes like a family. Do you feel that’s true?
Valerio: Absolutely -the time and mental space you dedicate are huge. And the truth is, the company doesn’t just stay at the office; it comes home too. It becomes part of your family conversations, with your partner, your kids. I see Graziano more than my wife! (laugh)
Graziano: Sure, entrepreneurship gives you some flexibility to balance things, but it also means you’re carrying the company with you everywhere. Honestly, I’d probably do it even earlier if I could -though, like having kids, it definitely takes a serious energy boost.
And is it all worth it? Do you ever wonder if it would’ve been easier to just stay in a corporate role?
Graziano: I wouldn’t go back -this is the best job you can have. Everything you build, day by day, comes from your own vision and effort, directly or through the people you bring on board. Even if you reach the top in a corporate, leading thousands of employees, you’re still steering something you didn’t create. In a startup, every detail -even down to the glass you buy -is something you built. That ownership, that personal spark, is what makes it all worth it.
You became Endeavor Entrepreneurs this year. What has your experience with Endeavor been like so far?
Valerio: The journey with Endeavor was long and demanding –it took time and effort -but the payoff has been incredible. It marked a real turning point for us. We gained a clearer sense of our potential and the value of what we’d built so far, and found real inspiration and support for what’s ahead. The quality of insight we’ve received -from technical to managerial to strategic -has been outstanding.
Graziano: Endeavor is truly the best when it comes to scale-up entrepreneurs, and I fully agree: what we’ve gained is priceless. We’ve just returned from a three-day Endeavor Outlier Retreat in Lisbon with some of the most successful founders in the global network. The way they share their knowledge -including mistakes -with honesty and generosity is something you rarely find. It’s an experience that’s hard to replicate.