Keith shares how he started the company in high school, the unconventional story of meeting his co-founder, and why solving operational complexity—not just building software—became the real unlock. From navigating illegal hardware deployments in the early days to scaling a fast-growing company, this conversation dives into product-market fit, fundraising, leadership evolution, and the massive opportunity hiding inside a $30B “cost center” waiting to be transformed.

Chapters

0:00 Intro

0:17 The Origin Story Behind BusRight

0:59 Identifying the School Transportation Problem

3:03 The Moment That Sparked the Idea

4:27 Building Entrepreneurial Resilience

6:58 Why School Buses Are a $30B Market

9:21 The Bearded Dragon That Led to a Co-Founder

12:20 Early Vision and Illegal Tablets on Buses

14:58 Finding Product-Market Fit

16:04 The Metric That Matters Most

17:15 What Keeps a CEO Up at Night

21:02 Fundraising and Choosing the Right Investors

23:59 Evaluating 11 Term Sheets

26:26 The Long-Term Vision for BusRight

28:13 Advice to His Younger Self

Connect with Keith Corso at https://www.linkedin.com/in/keith-corso/

Learn more about BusRight at https://www.busright.com/

Connect with Steve Greenfield at https://www.linkedin.com/in/stevegreenfield416/

Learn more about Automotive Ventures at https://www.automotiveventures.com

Jim Roche, Founder and CEO of WarrCloud, breaks down how a $28 billion industry is still being managed with manual processes, paper trails, and outdated workflows that quietly erode dealership margins every single day.

As a portfolio company of Steve Greenfield's Automotive Ventures, Roche shares how a simple observation: stacks of paperwork representing “uncashed checks,” turned into a category-defining company. They dive into the economics of warranty reimbursement, why the problem went unsolved for decades, and how AI is reshaping back-office operations. Along the way, Roche reveals hard-earned lessons from building multiple companies, scaling WarrCloud, and the mindset required to win in a complex, high-friction industry.

Takeaways:

0:00 Intro

0:44 The “Stack of Uncashed Checks”

1:55 Founding WarrCloud and the 7-Year Build

2:39 The $28 Billion Warranty Opportunity

3:55 WarrCloud’s ROI for Dealers

5:32 Why No One Solved This Earlier

6:56 How AI Is Transforming Dealership Operations

9:07 Jim Roche’s Entrepreneurial Journey

10:00 Leadership Principles That Drive Success

12:01 What He Would Do Differently

12:55 The Big Business Model Pivot

14:06 Metrics That Matter Most

16:13 The Power of Mentorship

17:52 Choosing the Right Investors

20:34 Vision for the Next 5 Years

22:25 Advice to His 18-Year-Old Self

23:25 A Different Path: Aviation

Connect with Jim Roche at https://www.linkedin.com/in/jimkroche/

Learn more about WarrCloud at https://www.warrcloud.com

Nikhil shares the journey from DARPA self-driving experiments to building a fast-scaling ADAS calibration network, revealing how operational speed, precision, and network effects are becoming the real competitive advantages in automotive services. He also offers a candid look at navigating uncertainty, choosing the right go-to-market model, and why the biggest opportunities often emerge after you launch—not before.

Timestamped Takeaways

0:00 Intro

0:19 Nikhil’s Background and Early Self-Driving Work

1:03 Building a Mapping Startup for Autonomous Vehicles

5:34 Why Kinetic Focused on ADAS Calibration

7:59 Early Assumptions vs Market Reality

10:50 Discovering the Collision Repair Opportunity

11:27 Navigating the “Fog of War” as a Founder

15:15 What Nikhil Would Do Differently

17:14 The Future of Autonomous Vehicles and ADAS

20:48 The #1 Metric That Drives Kinetic

22:49 Scaling a Network-Driven Business

24:50 Fundraising Strategy and Investor Selection

30:08 Advice to His Younger Self

31:32 Lessons for Entrepreneurs

33:21 Bold Predictions on Robotics and Autonomy

Connect with Nikhil Naikal at https://www.linkedin.com/in/nnaikal/

Learn more about Kinetic at https://www.kinetic.auto/

In this first episode of Greenfield, Automotive Ventures General Partner Steve Greenfield and Venture Principle Justin Charbonneau unpack the unlikely path that led to building one of the most active seed-stage investment firms in mobility. From quitting stable corporate jobs and surviving failed startups to launching a venture fund in the middle of the COVID shutdown, they share the real story behind how Automotive Ventures came together.

Along the way, they break down how venture capital actually works, why most startups fail, what red flags they look for when evaluating founders, and why the best entrepreneurs don’t need capital—they choose their investors. After reviewing thousands of startups and investing in more than 55 companies across three funds, Steve and Justin reveal the mindset, pattern recognition, and founder traits that drive the biggest outcomes in mobility.

Takeaways:

0:00 Intro

0:40 Justin on the long road to entrepreneurship

4:31 The coffee meeting that triggered a resignation

5:46 Telling his parents after quitting in week one

8:20 Running out of runway and finding startup life

10:20 Building a startup in the wine industry

13:33 What failed founders learn that others miss

15:55 Winding down a startup in March 2020

18:15 From angel network research to launching a fund

21:34 Steve’s own founder journey and corporate reset

27:57 The $5,000 angel bet that changed everything

36:08 The karma bank and how Automotive Ventures helps founders

45:32 Red flags, return math, and why stage matters

Connect with Steve Greenfield at https://www.linkedin.com/in/stevegreenfield416/

Connect with Justin Charbonneau at https://www.linkedin.com/in/justincharbonneau/

Learn more about Automotive Ventures at https://www.automotiveventures.com

Hosted by Steve Greenfield, General Partner of Automotive Ventures, the show offers a clear, disciplined perspective on the technologies, retail innovations, and market forces reshaping how people and goods move.

Each week, Steve brings a mix of conversations and analysis. Some episodes feature mobility founders, dealers, OEM leaders, or investors—people building at the intersection of technology, transportation, and automotive retail. Other episodes dive into the signals Steve and his team at Automotive Ventures are seeing across thousands of startups each year: where capital is flowing, which trends actually matter, and how value will shift over the next decade.

From EVs and autonomy to dealership technology, robotics, energy, and industrial mobility, Greenfield goes beyond headlines to translate noise into insight—helping you understand where opportunity is emerging and how to position yourself early.

New episodes every Tuesday.

Subscribe to stay sharp on what’s next in mobility.