Deepak Chhugani

The through-line

Deepak Chhugani's recurring subject is reinvention: of himself, from banking analyst to founder, and of the company, which he describes as having had "constantly been moments to reinvent" through COVID, the 2021 funding craze, a three-year freight recession, and now the arrival of AI [1]. He treats the destination as stable and the route as negotiable. Nuvocargo began with a pitch he now finds dated ("we want to be something like flexport but for US Mexico") and has become, in his framing, the partner to North American shippers with cross-border supply chains, carrying managed transportation and customs brokerage products on a software stack rebuilt from scratch eighteen months ago for the age of AI [1][2][4].

The second thread is what he actually values out of the experience. Asked how it feels to have built a company valued north of $250 million, he redirects to the learning curve: "a lot of it is about the journey and the growth that you personally get" [1]. He is explicit that what he considers business experience arrived "very very fast like in a matter of two or three years since starting the company," and that his ongoing ambition is to keep the curve equally steep [1].

On growing up assuming you would start something

He was born in Kenya to Indian parents and grew up in Ecuador, where his father ran a logistics business [1][3][7]. He reads entrepreneurship there as a default setting rather than a calling: "when you grow up in Latin America or even in India in emerging markets, I think a lot of the people that are successful are business owners. So, it was almost like a default where you assume, hey, if you're ambitious, you're going to try to start your own business" [1]. As a child that meant studying whatever family businesses were nearby, "whether it was a small landscaping business around or an import export business" [1]. His multicultural background, and the immigrant experience in Ecuador specifically, is a story he has returned to repeatedly [3][5][7].

On what investment banking gave him, and what it hid

He is unsentimental about the hours and clear about the residue. Landing an analyst seat at Bank of America Merrill Lynch without an Ivy League degree felt like "an opportunity to play in the big league so to speak for the first time" [1][3]. On the current startup fashion for 996, he notes that a nine-to-nine, six-day week "would have been your best week of the year in investment banking," since the reality was arriving at 9:30 and staying until 2 a.m. seven days a week, and he refuses to romanticise it: "I don't think anyone is proud of that looking back if you really went through it, being sleepd deprived uh and uh you know, not working at your best" [1]. What survived is the reason for the hours rather than the hours themselves, the "intense attention to detail" of sending decks to CEOs of multi-billion dollar companies at twenty-one, which builds "this muscle of quadruple checking everything maybe to a point that's OCD and is not healthy" alongside a durable work ethic and the composure to judge "what should I say, what should I not say being in this room" [1]. He is candid that he was, by his own account, "the most mediocre analyst from that whole class" because the deadlines and tasks often did not make sense to him [1].

The limitation he names is analytical distance. Modelling a retail sector or an energy deal, or pitching a government on an airport RFP in Mexico City, "doesn't let you understand what it's like to actually run a business. You you you think too much in spreadsheets and high level and you don't get the nuances of what each business is about" [1].

On mentors and earning people's time

He credits his exit from finance largely to proximity to people a few years ahead. Friends of friends introduced him to venture-backed founders, including Sebastián Castro and Karim Atiyeh, who "were kind enough to encourage me to really quit and do things" [1]. That pattern became a policy: "people who know me will know that I'll obsessively try to reach out to people who are a few steps ahead of me. Every one of our funding rounds, we added entrepreneurs that had done it before" [1]. He tells people in their early twenties that they underestimate this: "you don't even realize but the mentors around you play a big role" [1]. The counterpart to that is a bluntness about entitlement, and his position that nobody owes you anything, not even twenty minutes of their time, and that access has to be earned [8].

On getting into Y Combinator, and on quitting without a plan

He quit with his first-year banking bonus and no technology background, and picked an idea afterwards, an approach he flags as reckless even though it worked: "I don't recommend that approach, but it it ended up working out in the end" [1]. Once he had an idea he "really got obsessed with Y Combinator," consuming every piece of content the firm had published and interviewing as many alumni in New York as he could before applying with recommendations in hand [1][10]. He notes what made the acceptance improbable: YC "didn't really fund single non- tech founders," and he was the first person from Ecuador they funded [1]. He still names it as "probably one of the most important moments for me in my life" [1].

On killing an idea and pivoting

The pivot is the episode he returns to most [3][5][7][10]. The original recruiting-adjacent business was rejected by every VC after demo day, so he raised $1.2 million from 41 angel investors "with small checks and really like grinding through these phone calls," from people "who trusted a first-time founder very young with this nent idea" [1]. Six or seven months later, at twenty-five and having burned only three or four hundred thousand dollars, he decided it was not working, and used YC partners including Dalton Caldwell as a sounding board [1]. His test for the adjacent ideas was ambition rather than viability: "None of them were exciting to me. None of them felt interesting. None of them felt like the kind of thing that could be big" [1]. That standard came from watching his own batch, which included Substack and Replit, companies that "were not obvious winners back then, but they just went on to be so big" [1]. He let all eight employees go and spent three months methodically researching ideas [1].

The restart was bought rather than built from zero. An introduction led him to Josh Wolf of Cargo Sprint, who sold him his freight forwarder, "which let us kick everything off, you know, having traction quickly, studying workflows, and being really aggressive in that all of 2019 to get it off the ground with with a lot of urgency the way you learn in YC" [1].

On evolving the company and buying capability

The through-line held while the tactics moved. Nuvocargo stayed focused on US-Mexico cross-border trade [3][5][6][7], then expanded into the US market via the acquisition of Merge Transportation, with the team "building all these functionalities to get us to the cutting edge of the US market as well" [1]. The stated ambition today is broader than the corridor: to be the partner to North American shippers, ideally those with cross-border supply chains into Mexico and Canada, "but even if they don't" [1]. The company's own summary of itself has moved from a technology-enabled logistics company to an AI-enabled one, and the shift to being AI-native is now the thing he is asked to explain [1][2][4]. Funding tracked that expansion in stages, a $12M round, a $20.5M round, a $36.5M Series B, and more than $75M raised in total [4][6][9][11].

On what AI actually does in freight

His examples are specific and operational rather than general. He points to border visibility tools, tariff management features, and a control tower for transportation that surfaces freight cost and SKU-level visibility [1]. The platform underneath, Nuvo US, was a full rebuild of the software stack undertaken eighteen months ago explicitly for the age of AI [1].

On the hype cycles in supply chain software

He warns founders that sentiment in the space swings hard and fast. In six years he watched "huge excitement the first two or three years we started with everything under the sun getting funded," followed by "two years of everyone hating anything that had uh logistics operational" attached to it [1]. He also rejects the founding myth that made the sector look easy: the narrative that incumbents "are still using fax machines, you just write some code and, you know, you'll have a unicorn" collapses on contact with the intricacy of each step of the supply chain [1]. On his own authority to say so, he is careful. He used to open by disclaiming expertise, and now allows only that "when you do a startup for more than six years in the space" you become somewhat of an expert, "I don't know if I am a full expert yet" [1].

On the emotional reality of the job

He argues the outside view is systematically wrong: "the crazier it looks from the outside. Uh the the probably 10x is it's probably 10x as crazy as you think on the inside. Even when things are going well, the highs are high, the lows are low" [1]. Freight amplifies it, because the business combines operations, software and macro exposure to things like US-Mexico tariffs, on top of cycles [1]. His account of his own motivation in his twenties, handed $75 million of capital, is fear-shaped: "a a lot of what you think about is, uh, you know, am I going to screw it up?" [1]. The maturity he claims is not calm so much as calibration, "learning to be a little more level-headed in both the highs and the lows because they are going to continue to be quite crazy" [1]. And he notes that founders rarely stop to register progress at all: "You actually almost never think about that, right? you're always thinking about the next 10 fires or 10 challenges" [1].

Takeaways

• Growing up in an emerging market made entrepreneurship a default expectation rather than a leap: "if you're ambitious, you're going to try to start your own business" [1].
• Investment banking's lasting gift was detail discipline and composure with senior people at twenty-one; its blind spot is that spreadsheets never teach you how a business actually runs [1].
• He quit finance and chose a startup idea afterwards, an order of operations he explicitly does not recommend despite it working out [1].
• Getting into Y Combinator came from saturation research: consuming every piece of YC content and interviewing as many alumni as possible before applying, as a single non-technical founder and the first from Ecuador they funded [1][10].
• He killed the first company six to seven months after demo day, having raised $1.2M from 41 angels, let all eight employees go, and spent three months researching before restarting [1].
• Nuvocargo got traction by acquiring an existing freight forwarder from Josh Wolf of Cargo Sprint, then later bought Merge Transportation to expand into the US market [1].
• The AI work is concrete: border visibility, tariff management, and a control tower giving freight cost and SKU-level visibility, on a stack rebuilt from scratch eighteen months ago [1][2][4].
• Ignore the "they still use fax machines" story about logistics; every step of the supply chain carries real intricacy, and sector sentiment swung from funding everything to hating anything operational within six years [1].
• Build a bench of operators a few steps ahead of you, and add experienced entrepreneurs at every funding round [1].