It was one of those Kansas fall days that reminds you why it’s worth stepping away from the desk — mostly sunny, calm, and the trees in Corporate Woods were in full, fiery color. The kind of day that makes good conversation feel even better.
After a great phone conversation last week, I finally had the chance to meet Ashish (Ash) Vaja, COO at Dream Assurance, in person. We met at his office in Overland Park, and what followed was one of the most insightful, genuine discussions I’ve had in a long time.
Ash is one of those people who doesn’t just talk to you — he talks with you. Within minutes, it was clear he wasn’t there to sell anything. He was there to understand. To listen. To share what he’s learned from years of helping carriers navigate one of the toughest parts of this business — insurance.
“We tell you what you need to hear, not just what you want to hear.” — Ash Vaja, COO, Dream Assurance
That’s Dream Assurance in a nutshell. They care about carriers — whether they’re insured through Dream or not — because they know knowledge and honesty are the best protection a company can have.
At one point, I asked Ash what he sees most often when trucking companies start to struggle. He didn’t hesitate.
He didn’t say it to scare anyone — he said it to prepare them. The truth is, most carriers don’t fail because they lack effort. They fail because they weren’t informed soon enough.
We talked about the “driver shortage” — a phrase that gets thrown around a lot in this industry. Ash smiled and said, “It’s not a shortage of drivers; it’s a shortage of qualified drivers.”
He’s right. The challenge isn’t finding people willing to drive; it’s finding the ones who share your values, take safety seriously, and help your company grow the right way. Dream’s consultative approach extends even to hiring strategies — helping carriers think beyond just filling seats.
Ash said something that really hit home: “Everything you do tells a story.”
When insurance underwriters look at your business, they’re not just reading paperwork — they’re reading you. Safety documentation, driver policies, maintenance logs — it all tells a story about how your business operates.
That’s why I built tools like the Enhanced Packet Builder — to help carriers tell their story clearly, confidently, and professionally. Because perception matters. When your presentation matches your professionalism, insurance partners take notice.
We also talked about how tools like telematics and cameras are changing the way carriers and insurers connect.
Telematics can help show a company’s safety culture in real numbers. Cameras protect both the driver and the carrier by showing the truth when it matters most.
As technology grows, tools like F-R8Cal will help bring that same transparency to the business side — giving both carriers and insurers a shared understanding of performance, cost, and reliability. That kind of visibility builds trust, and trust builds better partnerships.
Our conversation turned toward one of my favorite topics — direct shipper relationships.
Ash confirmed what I’ve been telling carriers for years: having direct shipper clients doesn’t just improve revenue; it strengthens your entire business. Carriers who have consistent freight tend to see better driver retention, safer operations, more predictable maintenance, and yes — lower insurance premiums.
It’s a win for everyone. FR8Connect and Dream share that same belief: when a carrier earns a shipper’s trust, everyone wins — including insurers.
Together, these steps make a carrier not just insurable — but dependable, respected, and built to last.
By the end of our visit, it didn’t feel like a meeting between business professionals — it felt like a genuine exchange between people who care about the same mission.
Ash and his team are approachable, transparent, and truly committed to helping carriers — whether they’re existing clients or just looking for guidance. That’s rare.
If you’re a carrier and you’ve got questions, give them a call. They’ll listen, they’ll share, and they’ll help you find your footing. Not because it’s their job — but because it’s who they are.