Image Credits: Bryce Durbin

Dan Lewis, co-founder and CEO of digital freight company Convoy, didn't start his company because of his passion for trucking. Not at first.

The executive has a background in strategy and management consulting and went on to work in product development for top tech companies. When he was struck by the urge to start a company, he researched the money-attracting industries of the world, and then used AngelList to see how many companies were trying to disrupt those industries.

Thousands of companies were found in his search, working in industries such as telecommunications, fashion, video games and food. Billions of dollars were going into trucking each year, but fewer than 30 startups showed an interest in the field.

I saw a huge opportunity and few people were interested in it.

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Lewis and Grant Goodale co-founded Convoy in 2015, and since then have brought on a number of high-profile investors. The company secured its Series B from the Continuity Fund after a couple of years after it was founded.

Convoy's valuation increased to $3.8 billion after it secured a $260 million Series E led by T. Rowe Price. The company has raised almost $1 billion to scale its platform, which connects the fragmented network of shippers, carriers and brokers across the United States.

Speed is a big feature of building a startup, and it’s also a big feature of not getting diluted, because you can show immense progress and then raise at a higher valuation based on that. Dan Lewis, co-founder and CEO of Convoy

We sat down with Lewis to talk about the importance of being customer-obsessed when starting a company, why compensation packages in the early days can help you avoid diluting your company too much in future fundraises, and how to set boundaries on the compromises you will make as a founder.

The following interview has been edited for clarity and brevity and is part of an ongoing series that focuses on founders in the transportation sector.

The investment in your Series B was notable because Convoy was not in the Continuity Fund. What made Convoy stand out?

The Continuity Fund was geared toward early growth-stage companies, so they didn't feel like they needed to stay in a particular lane. When we met, I think the breakthrough was just the story. People don't realize how fragmented the trucking industry is. This was viewed as a major disruptive play by YC.

We were excited to work with them because they're an incubator and they're designed to help founders succeed. They had many unique programs that helped us grow and be successful.

A good way to decide on a direction for a startup was to compare industries with lots of money against companies that are trying to disrupt them. Is that still a good method?

I think it's a good method. It would be interesting to pull a list of industries and find out how much money is spent in them, and then see how many companies are going after them. The newest, most innovative companies can be found on AngelList.

The article I wrote before I started the company was published by Forbes. The answer was to come up with a startup idea. I wrote an extensive theory. I was going to start my own company and I wanted to eat my own dog food. I used my own process and it works, so I can say it is credible.