Reilly details a sector-specific then-and-now look back from his more than two decades of transportation experience, shares how the venture asset class has shifted in light of the momentum in this sector and what this has meant for sector-focused VC firms, outlines why building ecosystem and collaboration across startups, investors, universities, regulators, etc. is needed for the next decade of transportation innovation to thrive, and finally shares lessons learned from investing in transportation business models that may combine both hardware and software components.