Meet the Investor: The man with the ‘dull machete’ leading project44’s growth

At the age of 33, Duboe not only is laying the path for the real-time visibility company, he was also behind the initial seed round that eventually led to the explosive growth we see from project44 today.

In an interview with FreightWaves, Duboe described his venture capital (VC) journey, from his high school educator who made economics and business digestible to the college relationships he developed that granted his first VC experience to the Friday phone call to project44 CEO Jett McCandless that led to his leadership role.

Questions and answers were edited for clarity and length.

FREIGHTWAVES: Between your Harvard economics degree and over a decade of experience in VC, on paper you seem to be bred for this industry. Where did your interest in business and VC stem from?

DUBOE: “It’s funny because all of my siblings ended up going into business and venture capital, but we certainly didn’t talk about business at the dinner table or anything like that. … My dad became a doctor and my mother was a nurse, so most of those [dinner] conversations were most likely about sports or medical terminology. 

“I actually had a really great economics teacher my senior year of high school in 2006. His name was Mr. [James] Kollar and he was a former options trader. What I really liked about his teaching style was his ability to use a lot of real-world examples throughout the course. He helped me understand economics in theory, but what I really enjoyed was the practice of those theories.

“The economist who interviewed me for Harvard admissions described it quite well. On any given day, if you pick up a newspaper, economics helps you translate what is happening from a macroeconomic perspective into how that is going to impact your day-to-day life.

“Once I got to Harvard, I was able to gain exposure to and an understanding of the entrepreneurial journey—whether it was through professors, alumni or classmates. I found their different backgrounds and stories to be fascinating and it provided some clarity into entrepreneurship. Understanding how and why people started companies was previously opaque to me. 

“Then, during a lacrosse clinic that I was coaching at during my sophomore year at Harvard, I met an entrepreneur who had brought his kids to the clinic. I told him I was really interested in private equity because it allowed you to work with entrepreneurs and learn more about different types of businesses.

“He introduced me to Tom Jennings, managing director of Summit Partners, and when I became a junior I asked him for an internship.”

FREIGHTWAVES: Was Summit Partners your first experience working in investment?

DUBOE: “Well at that point, Tom said, ‘We don’t really do internships, you should go work on Wall Street and come back to us next fall and interview with us.’

“I stayed in touch with Tom like every month until I eventually got the job at Summit. In the meantime, I worked at Credit Suisse for my summer internship. I didn’t find the work to be that interesting, analyzing how companies worked and doing a bunch of financial analysis and market making for those companies. I was more interested in the stories of the entrepreneurs themselves and finding ways to invest in the entrepreneurs directly.

“What is most interesting to me is understanding the entrepreneurial stories and their vision and seeing if there are ways that I can either learn from them or find ways to be helpful to their cause.”

FREIGHTWAVES: Once you started at Summit Partners in 2010, what was your day-to-day work life like?

DUBOE: “My job was to cold call entrepreneurs. Summit was the original growth equity firm that sourced their investments through associates cold calling entrepreneurs.

“Those calls consisted of both buying and selling because the entrepreneurs running successful companies didn’t necessarily need capital. So my job became a mix of describing Summit’s value proposition to these entrepreneurs while at the same time assessing the validity of the business model of the company and whether or not it would be an interesting portfolio company.

“We were not provided with leads. You had to come up with your own ideas, learn about industries that were interesting and research publications to find companies to call. There wasn’t a FreightWaves profiling all of these interesting companies, so I found myself looking up trade shows and reading obscure technology publications trying to find interesting software companies to invest in.

“I probably made 10,000 calls, was able to have good conversations with 5,000 of those entrepreneurs and ended up pitching a deal to maybe a hundred of them in total. I only closed four investments in three years, so there is an enormous amount of outreach needed for just a couple investment opportunities.

“Through all of that work, I got to know all of these entrepreneurs, their backgrounds and growth stories. Traditionally, Summit would get involved with bootstrapped companies that had not raised capital before and then would go in and help them with market expansion and all things critical to scaling companies.”

FREIGHTWAVES: Do you feel like investing in the bootstrappers had better outcomes and has it changed over time?

DUBOE: “It has definitely changed. Back in 2010 [at Summit], investing in companies that didn’t necessarily need capital presented better opportunities because there was more opportunity to help these entrepreneurs and create more leverage in their business.

“Today, there is so much financing available that even serial entrepreneurs are raising capital early and often. I think ultimately, nowadays it’s about finding the right set of investors that can be helpful to your business and actually understand the challenges that occur at each stage of the business life cycle.”

FREIGHTWAVES: What led you to founding Chicago Ventures in 2013?

DUBOE: “At Chicago Ventures, our mission was to invest in underrepresented geographies and companies that traditionally didn’t have access to early-stage capital. We made it a point to invest in seed-stage companies and startups.

“The Midwest is so diverse in talent and industry, so we thought, ‘How can we connect these early-stage businesses into various segments of the economy that exist in the Midwest that others did not have access to?’”

FREIGHTWAVES: Once you were settled in at Chicago Ventures, how did you end up meeting Jett McCandless, founder and CEO of project44?

DUBOE: “I remember it perfectly. It was a Friday afternoon and I read an article in Crain’s about Jett. It spoke on his background, his journey as a scrappy entrepreneur and he had this unique perspective around application programming interfaces (APIs), the infrastructure of logistics and how he planned on evolving the industry. 

“His thoughts mimicked my thoughts on the infrastructure of other industries driven by APIs as a service type of businesses like Stripe or Twilio. Jett had the same idea but for transportation and logistics. 

“What intrigued me was this deep founder-market fit, the fact that you could see this trend coming and there was virtually no digitization happening yet in an $8 trillion industry.

“On that alone, I cold called Jett on that Friday. I downloaded every article that I could find on project44 and their website. They said I almost crashed their website because I was trying to find everything possible to actually make a sales deck for Jett.

“When we were trying to earn the opportunity to invest in project44, I built a sales deck for Jett to explain to him why Chicago Ventures would be a strong partner. I tried to describe Jett’s vision and in some ways did so better than they could at the time because we had seen these businesses become successful in other industries. There was immediate alignment between us, so we wrote the first term sheet for project44’s Series A.

“Until then, Jett had funded the business himself for several years, which was also super impressive that he was investing a lot of his own capital in the company early on and we were fortunate enough to be invited into the business at that time. Little did I know that the business was nearly bankrupt by the time we invested.

“Despite the company’s capital position, Jett pursued not only the best Chicago investor he could find, but also wanted to partner with an established world-class software-as-a-service investor. We thought Emergence Capital was one of the best software-as-a-service firms out there for early-stage companies, so over time we convinced them that project44 could be a really impactful business opportunity and we ended up co-leading the round with Emergence Capital.”

FREIGHTWAVES: How did you end up transitioning from Chicago Ventures to becoming the chief growth officer of project44?

DUBOE: “Stuart Larkins [co-founder and general partner of Chicago Ventures] always felt that I should gain operating experience. I told Jett that I wanted to join project44 and I was lucky to have the position available to me. I joined the team in 2017, before we raised our Series B with about 20 to 25 employees. 

“I think my role, first and foremost, is to be as helpful of a business partner to Jett as I can possibly be. Jett has so much on his plate and my job as an executive is to work on the projects that are most important to him and the things that will add the most value to the company.

“Jett told me my job was to take a dull machete and chop through the jungle and lay a path for people to come in after me and really scale our efforts. That may mean capital raising for M&A, that may be working on the largest enterprise deals, that may mean closing on key executive talent and preparing us for an IPO.

“There are no two days that are the same, it’s just doing the thing that provides the most value to the business at that given time.”

FREIGHTWAVES: While your overall career is still young, with the level of experiences that you have had, are there any mistakes or lessons learned that you would want to share with young investors and entrepreneurs?

DUBOE: “Frankly, I think certain venture capitalists tend to overstate how much value they actually bring to bear. It’s really about the entrepreneur. It’s all about understanding where their mindset is and what resources can be most useful to them.

“I think some of the mistakes that venture capitalists make is they come in with a preconceived notion of how markets should play out or will play out. Ultimately if there is a true founder-market fit, an entrepreneur is going to perceive a problem or a solution to that problem much differently than myself.

“When you are investing in the seed stage, it’s all about the entrepreneur. Investors can be extremely helpful with helping recognize the market opportunities that are available and steer the entrepreneur into those opportunities, including access to customers. Landing those first 10 to 20 customers is really critical when you talk about B2B software.

“Personally, I think the most important lesson I have learned is take as many meetings as you can. Don’t be arrogant or closed off to a new meeting. Yes, the introductions should come from a trusted source, but many times the meetings I regret the most are the ones that I did not take.

“Also, investment opportunities come in all shapes and forms, you never know where an entrepreneur is going to come from and their unique insight and background can be very important. 

“Diversity and inclusion should be prerequisites when it comes to investing. There is no rule to who is going to build the next multibillion dollar company, so being able to really listen and seek understanding of people’s backgrounds and perspectives is absolutely critical.”

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