In this episode of Culturally Sound, Chandler Cutler sits down with Kristina Fahl to unpack how a daily school run problem became an InsurTech mission. After more than fifteen years in large financial institutions, Kristina left a stable career to launch a student transportation company. She scaled fast, hit the wall on commercial auto insurance economics, then joined venture backed teams to learn how risk is structured at scale. Today at Shuttlebee she is unlocking trapped supply in student transportation by equipping small operators with tools, training, and embedded insurance so they can deliver big fleet standards safely and reliably.

The conversation is candid about imposter syndrome, learning in public, and turning setbacks into operating advantages. Kristina explains how she moved from purely tactical problem solving to strategy and people first leadership, why feedback loops and community make or break momentum, and how preparedness reduces anxiety when safety and compliance are on the line.

Guest Bio

Kristina Fahl is the founder and CEO of Shuttlebee, an InsurTech platform that merges predictive dispatch, compliance automation, and embedded commercial auto insurance to expand safe and reliable student transportation. Previously she led operations at Bus.com, scaling logistics across North America, managing vendor compliance, and leading end to end RFPs for institutional clients. Her inspiration for Shuttlebee came from running an award winning student transportation company where she saw strong small operators priced out of insurance. Kristina is a graduate of RevTech Labs Accelerator Cohort 22 and Scout InsurTech’s Recognized Leader program. Her mission is to make student transportation safer, smarter, and more accessible.

Episode Breakdown

• From Corporate Comfort to Startup Chaos (00:00 – 02:15)

Why Kristina walked away from 15 years in financial services, the school drop off problem that sparked her first venture, and the hard lesson of insurance costs that forced a shutdown.

• Finding Her Footing in Transportation (02:15 – 03:25)

Joining venture backed startups, leading operations at Bus.com, and stepping into insurance and regulatory work that would shape Shuttlebee.

• Confidence, Rage, and Imposter Syndrome (03:25 – 06:25)

The reality of building in a male dominated industry, the power of frustration as fuel, and why imposter syndrome never fully disappears.

• Failing Forward and Listening Hard (06:25 – 09:14)

Reframing failure as essential to growth, learning to see blind spots, and surrounding herself with people unafraid to tell her the truth.

• Momentum and Venture Backing (10:03 – 11:26)

How Shuttlebee shifted from a grind uphill to a venture backed company with growing speed, thanks to the right team, board, and advisors.

• Measuring Leadership in Real Time (12:41 – 15:37)

Why reviews should hold no surprises, the practice of writing letters to her future self, and how intentional check-ins build stronger teams.

• The Limits of Optimism (25:22 – 26:31)

Believing in people’s potential vs seeing where they are today, and how optimism without balance can lead to tough leadership calls.

• The Power of Community and Asking for Help (27:58 – 30:29)

Why networking felt intimidating at first, and how mentors and peers turned into the biggest accelerators of growth.

• Preparedness Over Anxiety (32:59 – 37:06)

Her morning and evening routines, the difference between aspirational and realistic habits, and how maximizing what can be controlled allows her to sleep.

• Defining Success by Joy (37:50 – 39:48)

Why joy, challenging company, and day-to-day wins matter more than a rigid ten-year plan.

Summary

Kristina Fahl’s story is a blueprint for resilient operating in a regulated industry. She turned a personal logistics problem into a company, learned the limits of unit economics, and returned with an InsurTech platform that gives small operators the safety, compliance, and insurance backbone of a big fleet. The episode delivers practical lessons on reframing failure, building candid feedback loops, using community as a force multiplier, and measuring leadership by how fast the people around you grow.

Relevant Links

🔗 Connect with Kristina Fahl on LinkedIn: linkedin.com/in/kristinagfahl

🔗 Listen to more episodes of Culturally Sound: corethos.com/culturally-sound