Keith Bender is a Partner at Pear VC, a venture capital firm that specializes in investments in seed and pre-seed startups. Of all the things he dreaded, Keith never wanted to become just another “excellent sheep.” The term came from the title of a book by a Yale professor about how the brightest minds from top universities were all flocking into the same industries of consulting or investment banking, becoming in effect uncritical automatons without the ability to think independently. The book had a profound effect on Keith. He had landed a summer internship at the prestigious Boston Consulting Group and had signed the firm’s offer to join the ranks of the consultant class after college. There he was, twenty-something-years old, another kid from Harvard going into consulting. The thought of becoming just another “excellent sheep” perplexed him, and Keith vowed to carve out his own path one day. He began spending time at Harvard’s Innovation Lab, which sparked his interest in the early-stage tech ecosystem. While he would go on to work at BCG for three years after college, he returned to Harvard--the second time to get his MBA--as an opportunity for self-reinvention. He envisioned two potential paths--either becoming an entrepreneur or an early-stage investor--and began surrounding himself with similarly inclined classmates. He interned at Bessemer Venture Partners and kicked around a few startup ideas. After his MBA, he ended up joining Pear VC as a principal, making partner earlier this year.
Keith had one of those classic, American childhoods. He grew up in the sun-baked state of Arizona, where the local kids spent each summer darting from pool to pool to escape the crippling heat. He nurtured a fondness for cars and craved the earnest prose of Great American novelists like John Steinbeck. Keith also played on the baseball team, sometimes on second base though most often as an outfielder. Playing outfield suited him. He was an introspective kid by nature and liked to stand there in the far end of the field, alone with his thoughts, waiting for some chance ball to fly toward his direction and interrupt his ruminations on questions ranging from the mundane to the existential. Nowadays, living in the Bay Area, he relishes the simple things: going on hikes with his wife, reading good fiction, and spending time with family and close friends. When asked where he saw himself in the future, Keith says that he hopes to remain in early-stage investing and continue supporting founders in their entrepreneurial ambitions. While his future remains unwritten, one thing’s for sure: Keith is far from being just another “excellent sheep.”
Sam: Could you share some insights into how you began your career and your path into venture capital?
Keith: After graduating, I started work in consulting at the Boston Consulting Group (BCG). I had interned there in college, and the honest answer is that about halfway through college I realized I wasn’t going to have an epiphany on what I wanted to do with my life by the end of school. I saw a lot of really smart people going into consulting, and I thought the role would give me a broader exposure to how businesses work and fill in some of the gaps of my education. The thing that was weighing on me at the time was discourse around a book written by this Yale professor called Excellent Sheep, which was about how all these well-educated students were running off into the same couple of fields--investment banking and consulting--and losing the ability to think independently. I had to reckon with this question – was I mindlessly following a well trodden path? Professors I admired most advised that l take a longer view of things and reflect on all of the possible worthwhile exits such a path enabled. For me, one clear area of interest was the early-stage entrepreneurial ecosystem. I was spending a lot more time at Harvard’s Innovation Lab, which had launched a new Venture Incubation Program. Through that program I worked on a few startup ideas, and I applied to business school my senior year out of an eagerness for an opportunity to return to a platform so supportive of entrepreneurial exploration.
I realized quickly at the start of my MBA that the first steps of researching startup ideas are similar for investor and founder journeys. Moreover, there was no predetermined path to either of those roles – that getting into either was generally an exercise in immersion. You don’t apply to become a founder, and frankly most investor roles don’t come through a straightforward application, either. I tried everything I could do to increase my exposure to these two fields by meeting with entrepreneurially-inclined classmates. For my summer internship, I worked at Bessemer Venture Partners with Kent Bennett, who today remains a mentor and friend. In my second year, I was kicking around a couple of startup ideas that had sprung from some of the research I had done over the summer at Bessemer, trying to figure out whether I should go the entrepreneurial path or formally enter into early-stage investing. I ended up joining Pear VC, which turned out to be a perfect fit on a number of dimensions. I started off as a principal in 2020 and was promoted to partner earlier this year.
Sam: What keeps you excited about your job as a venture capitalist?
Keith: I get the most energy out of working with the founders of our portfolio companies. I find the uncontained ambition of the founders I work with inspiring. They’re the type of people who look for every opportunity to improve themselves and their company. In working with founders, you get in these patterns where something in the world happens or you see a certain news headline and you immediately want to be in a room working through the ensuing opportunities with them. I work with one of our companies in the live events ticketing space, and every time Taylor Swift breaks the internet – or at least early internet-era ticketing platforms – we end up wanting to talk for hours about lessons and opportunities.
Sam: What would be the biggest learnings that you would take away from the last few years of your career?
Keith: In the early days of my venture investing career, I found myself falling into a couple of common traps that many newcomers face. First off, it was all too easy to be reactive and respond to every pitch that came my way. Working at a firm that has such extensive reach as Pear means you can be inundated with enthusiastic entrepreneurs eager to discuss their startups. Don't get me wrong – it was great to step into a flood of opportunities, but I quickly realized that I needed to be more selective in my approach.
The second challenge was the desire to make an investment as soon as possible. When you're new, it's natural to get attached to the first few promising companies you come across. Now, instead of rushing into deals headlong and trying to blitz-diligence them through an investment process, I try to focus. If I find a sector or problem that genuinely interests me, I start pulling on those threads, diving deeper into research, and hunting down every other company tackling the same challenge. By doing so, you gain expertise around specific business models, industries, and problem-solving approaches.
Of course, it's tempting to get swept up in excitement for the first opportunity that comes your way, and then the next, and the next. But by taking the time to truly understand a specific problem space, you can make more informed decisions and increase your chances of success as a venture investor.
Sam: What do you view as the hard part of being a VC?
Keith: Venture capital is an industry that seems to look in on itself a whole lot. The number of newsletters or Twitter influencers in venture capital relative to the number of people actually practicing in the industry is probably the highest of any field. It’s not just that everyone has an opinion – everyone has an opinion and is convinced that shouting it from the rooftops is part of the job.
It’s tempting to just get drawn into that dialogue. There’s also this pressure to constantly package yourself for public consumption. That’s the weird thing for me. Creating a strong social media presence probably helps with deal flow, but it’s still unclear whether all these efforts across social media translates with being a really good investor in terms of identifying promising companies and supporting them. Any time you’re tailoring your latest 27-part Twitter thread is time you’re not spending with your founders or familiarizing yourself with a new investment opportunity. That’s one of the weird dynamics of venture capital.
The other hard part of early-stage VC: every day, you can wake up to news that makes you feel like you’re terrible at your job. You see that X peer firm invested in Y awesome-looking company, and you scour your records to ask if you should have or could have met the founder. Obviously, we try to mitigate the number of times we feel that way by seeing as many companies as possible, but it’s still a gut-wrenching thing to feel like you missed out on an opportunity. Studying misses matters so that you can improve, but FOMO can be taxing and impede focus on specific opportunity sets.
Sam: Where do you see yourself in a decade or two decades from now?
Keith: Hopefully in one and two decades I’m still investing in and supporting early-stage founders. And, of course, hopefully the founders I’m working with now have happily IPO’d, spent sufficient time on beaches, and are back at it again working with us as repeat founders – and also as LPs in our fund!