From Burritos to Umbrellas: The Story Behind Monoline

Monoline didn’t start as a pitch deck or a sudden flash of inspiration.

It started with four people, years of shared experiences, a couple failed experiments (including a late-night burrito business), and a growing frustration with how personal umbrella insurance had been left behind.

This is the short version of how Monoline got started.

(For the full story, you can listen to the podcast episode embedded below.)

Four Founders, One Shared Mindset

Before Monoline, each founder was building something different, but all were learning the same lesson: real progress starts by listening to the people you’re building for.

Ben Phillips and Jerod Blakestad both built their careers in insurance, where they developed a shared respect for the work happening closest to the customer. Ben entered the industry during college, and quickly learned that his passion was building, not navigating corporate hierarchy. Jerod spent nearly his entire career in personal lines, developing deep empathy for the complexity and responsibility of serving individuals and families.

Their paths eventually converged in the brokerage world at Blakestad Private Client, and later at OpenTrack, a specialty insurance company for race cars. Those experiences solidified their commitment to listening first and building solutions rooted in real-world needs, an approach that would later carry over to Monoline. 

Greg Blasko and Carson Kipfer met their freshman year of college and quickly discovered they had complementary strengths. Greg’s superpowers were technology and systems, while Carson’s were centered on design and user experience. Together they co-founded SportsEngine, a SaaS platform built to help youth sports organizations manage websites, communication, and operations. What started as a small business turned into a popular platform adopted by youth sports teams nationwide and was eventually acquired by NBCUniversal.

SportsEngine taught them how to scale thoughtfully, validate product-market fit early, and listen relentlessly to users—lessons that would later shape Monoline’s DNA.

OpenTrack: The Dress Rehearsal

The four co-founders officially joined forces during the creation of OpenTrack.

Ben and Jerod quickly realized that without purpose-built technology, OpenTrack couldn’t scale. Paper processes, spreadsheets, and manual payments simply wouldn’t work. A chance introduction led to deeper collaboration, and soon Greg and Carson joined to build the tech that OpenTrack needed to grow.

What emerged wasn’t just a successful company but a proven founding team.

Each founder brought a distinct “superpower”:

• Ben: Strategy, operations, and leadership
  
  
• Jerod: Sales, distribution, and agency relationships
  
  
• Carson: Design and user experience
  
  
• Greg: Technology and platform architecture
  
  

They also set a rule that still holds true today:

Only build businesses with people you genuinely like and respect.

Why Umbrella? Why Monoline?

After OpenTrack, the question wasn’t what to build next, it was where they could make the biggest impact.

Personal umbrella insurance, despite being critically important, had become unnecessarily complex:

• Long turnaround times
• Friction-heavy workflows
• Limited capacity
• Technology that didn’t help at the desk level

Account executives were spending days (or weeks) placing relatively small policies, often earning minimal commission for outsized effort. The math didn’t work and everyone felt it.

So the founders did what they’d learned to do best: they asked agents directly.

Through a customer council of account executives, admins, and agency leaders of all sizes, the message was clear and consistent:

Start with umbrella. Make it simple. Give us our time back.

Monoline was built from that feedback—iteratively, collaboratively, and sometimes by throwing out early ideas that didn’t work.

Those early insights shaped everything:

• A streamlined quoting and binding experience
• Downloadable policies from day one
• Disciplined underwriting
• Real humans behind the platform

Monoline’s philosophy is simple: technology should amplify people, not replace them.

The Takeaway

Monoline isn’t just an insurance company. It’s the culmination of decades of experience, multiple successful ventures, and a deep respect for the people who place business every day.

It’s proof that when you combine strong relationships, thoughtful technology, and a genuine desire to help, you can build something that truly stands apart.

And this is just the beginning.