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Meet the investor: Robert Kaplan

March 5, 2021

What investing areas do you focus on at B Capital Group?

At B Capital, I invest primarily in horizontal software with a specific focus across consumer enablement and workflow automation. Before working in venture capital, I ran a growth team at a high-growth consumer marketplace startup. While working between marketing, product, and analytics, I became incredibly interested in how advancements in areas like natural language processing, ML/AI, and commerce infrastructure can help “humanize” digital interactions with customers (whether they be individuals or other businesses). Digital relationships between businesses and their customers will only increase in importance over the next decade and not just in the US, but globally. The tools and platforms enabling these relationships will be transformative in providing better access to goods, personalization, and customer service while streamlining business operations and encouraging entrepreneurship.

What’s something that you always look for in a pitch?

Investors generally look for a few key elements: founding team ability, early traction, market size and dynamics, etc. As an early growth stage investor, there are two additional areas that I am very focused on.

First is proof or sightline towards making the jump from “product-market fit” to “growth-market fit.” To me, product-market fit is when a company has an early subset of customers using their product, proving that there is a use case. Growth market fit is proof that a significantly broader market has a desire for that product, whether horizontal or vertical. Getting 10–20 customers or pilots can indicate strong early traction, but the product still may be niche or built for that contingent. Scaling to 500 customers is a completely different animal. How do you win your next 100 customers?

The second is understanding the company’s economic moat. How can your business increase its moat or advantage versus competitors as it gains additional scale? I like to hear founders talk through their product today versus their 5-year vision, how they achieve growth-market fit, and what economic moats come into play as they grow. This generally requires a strong product vision where a company builds a platform rather than a point solution, and the founder executes something fundamentally different from the market as opposed to a copycat solution.

What do you look for in a founder or executive team?

Vision, strong knowledge of the market, the ability to attract great talent, and the wherewithal to allow hired talent to execute, are a few key characteristics I look for in a founder and executive team. The funnel of founding teams I see gets smaller from left to right. Many founding teams have large and bold visions, but fewer have deep knowledge and connections in the market or industry they want to disrupt. Still fewer effectively sell their vision to top talent and convince them to get on board and join their mission. Even when they do attract that talent, one of the biggest hiccups an executive team faces while scaling is trusting the talent they bring in. The best founding teams should understand their weaknesses and allow the individuals they hire to fill these gaps. Micromanagement can not only interrupt a company’s ability and speed of execution, but also kill a team’s ability to attract the best people.

What attracted you to work at B Capital?

In my previous operating experience, I led a growth team and helped with international expansion at a startup that was scaling from Seed to Series C. The experience left me with two fundamental thoughts around scaling. First, the leap from product-market fit to growth-market fit is incredibly difficult — it should only be done when a company has developed a way to scale sustainably. Having experience leading a growth team through this phase, I feel that I bring knowledge and expertise to founders making a similar leap. The second is that technology does not adhere to borders. Seeing technology adoption in EMEA and Southeast Asia, they are, in many ways, ahead of the US. Any leading technology company should be thinking through a fully global strategy.

I was attracted to B Capital because the vision here aligned with my beliefs on technology and where I can best support founders. I’m interested in the opportunity to not just provide capital but support our founders with a full platform of resources to help them make the leap to growth-market fit and develop a global vision. I believe this is the real differentiator for our fund.

If you weren’t in this career, what would you be doing?

I grew up in Greensboro, North Carolina, which is the heart of college basketball fanaticism. Given that playing the NBA probably isn’t in the cards (if any team is looking for an undersized point guard with limited shooting range and athleticism, hit me up), I would love to be a college basketball color commentator. I find college basketball fascinating — the players are younger and far less skilled on average, meaning there is much more importance on the strategic elements of the game as well as more visible growth in the team and individual performances throughout the season. I would love to provide live analysis on the strategies implemented while sitting in some of the best sports environments in the world. That, and coming up with my own catchphrases would be a dream come true.

What’s something many people may not know about you?

I am a film buff and originally planned on studying film in college but decided to pivot after getting direct feedback on my first short film — sometimes a love for consuming something doesn’t translate into the ability to make it.

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