Inside Summit Recap: A Conversation with KJ Sidberry
To kick off Inside Summit, Madison and Claudia were joined by Google Ventures’ KJ Sidberry. Whether you’re founder, funder, or operator in the space, KJ shared valuable insights across the board.
Panelist Profile: KJ Sidberry
Listen on Apple Podcasts or Spotify
Current Company/Fund: Google Ventures
Hometown: Stamford, CT / New York, NY
Key Quotes from our Conversation:
- “Some cringe is helpful”
- “[Synthesis] should be the superpower of all VCs”
Female Hero: His high-school math teacher. “One of the first people outside of my family who challenged me to do more, and gave me a sense of confidence that I was capable of doing more”.
At a Glance:
- KJ’s Background and Frameworks for Decision Making
- For founders
- For funders
- Industry Insights & Thesis
KJ’s Background & Frameworks for Decision Making
Childhood
Born and raised on the East Coast, Sidberry grew up splitting time between Connecticut and New York City. With parents who worked in entrepreneurship and education, Sidberry’s upbringing exposed him to “two ends of the spectrum”, not only in terms of location but also career and opportunity. He credits this early experience to fostering a broadened understanding of what was possible in his own life and career.
Rejection is Redirection
Sidberry shared that his childhood dream was to be a graphic novelist. However, when he got to Harvard University, he was rejected from his preferred major in graphic design. This rejection, albeit minor, redirected him toward a degree in neurobiology and computer science, and put him on a path into consulting right after school. Sidberry recalls feeling that there were a few set paths which he could take after school, and pursuing consulting would give him not only a business acumen, but an exposure to “where things were happening”. Perhaps most crucially, the job brought him to San Francisco, where he was exposed to the world of venture capital for the first time. Just six months after this initial exposure, Sidberry found himself at the first pivot point in his career, and joined Forerunner Ventures.
Frameworks for Career Pivot
When considering the pivot points in his career, Sidberry shared his decision-making framework.
Pivot 1: Consulting to VC
When moving from consulting to venture capital, Sidberry distilled his decision into three key priorities.
1/ Find an organization that challenged the homogeneity he had grown accustomed to in the consulting world.
2/ Find opportunities to partner with founders at the earliest stages, versus when the companies have hit the fortune 500
3/ Take on a role which allows him to “tap into the psychology of people”.
On the third point, Sidberry referenced Maslow’s Hierarchy of Needs, a five-tier model illustrating the basic needs of human beings in their order of importance (though this order can be subjective). Sidberry uses frameworks like these, as well as his own experience, to connect with founders at the human level. He saw the role of a VC as one with the opportunity to explore this connection more deeply, and drive outcomes as a result.
Ultimately, Sidberry notes that his decision to join Forerunner Ventures was “remarkably easy”. With all-star Kirsten Green at the helm, Forerunner’s remarkable reputation as a leader in consumer investing and an impressive [all-female!] team, Sidberry considers himself lucky to have begun his VC career there.
Pivot 2: FV to GV
At the next juncture, Sidberry’s list of priorities was much shorter. He wanted to be closer to family, which meant returning to NY. Taking the opportunity to join Google Ventures allowed him to continue his career growth, explore a new team and firm, and be present in the lives of his younger brothers.
II. For Founders
Advice when Pitching
A key challenge for founders is raising money. Convincing investors to share their conviction, often with just a brief pitch and a few slides, is no small task. A pre-existing, genuine relationship is the ideal tablescape for building a strong investor-founder partnership. Sidberry emphasizes this before offering any pitching advice. However, even with deep connections, pushing forward can feel awkward, especially for founders. Sidberry believes this discomfort is healthy, strengthening the dynamic between founder and funder. In short, he encourages founders to push forward, noting that “some cringe is helpful.”
Framework for Successful Pitch [Green Flags]
However, without that relationship of trust and good-will, there are still a number of stand-out qualities that founders can convey when making a first impression. When asked what traits catch his attention during a pitch, Sidberry gave three:
1/ Magnetism.
2/ Deep curiosity.
3/ Founder-market fit.
Key tip when pitching: The most common pitch mechanism is still slides, but Sidberry points out that internal communication within firms is done via memo. If founders can go the extra step to pitch in a memo-format, they remove a lift off of investor’s plates. Not only will you communicate your pitch, but you’ll be doing your potential partners a favor.
III. For Funders
Framework for Passing on a Founder
From an investor’s perspective, developing instincts for when to pass on an opportunity/founder takes practice. In many ways, understanding when and why to pass can be just as difficult as deciding to move ahead with partnership. The key trait that causes Sidberry to hesitate when meeting a founder?
“A lack of paranoia.”
Sidberry emphasized how challenging it is to start a company, noting that founders who can’t recognize their own blind spots or identify gaps in their product or company raise concern due to a lack of awareness. In the course of building a company, countless challenges and problems will inevitably arise. Having foresight and a sense of urgency around the potential gaps and challenges demonstrates awareness and drive to succeed. While Sidberry doesn’t expect founders to have all the answers, if nothing keeps them awake at night, this may signal a lack of drive.
How to be a good board member?
Investor-founder partnerships can often take shape in the form of board membership. A seat on the board of a company, particularly in the early stages, is a crucial responsibility. That said, the value of a board can easily be diluted if not conducted with intention. Sidberry’s main advice for a successful board meeting?
Speak Less.
A VC’s superpower as a board member is the ability to synthesize and contextualize problems based on their seasoned exposure. Sidberry notes that in his own experience, the most profound impact has been driven by VCs who are able to offer this perspective without hogging airtime. In fact, Sidberry believes that board members should push to be kept in the loop frequently, leaned on heavily, and intolerant of surprises. Board meetings should feel like “strategy meetings, not catch ups”, Sidberry quipped.
“If I am finding out at the board meeting, it might be too late to help.”
Creating a dynamic of transparency and true partnership allows founders to lean on their board, and the ensuing board meeting to be a meaningful strategic exercise. VCs can help foster this dynamic by setting the tone upfront when taking a board seat.
IV. Industry Experience, Insights & Thesis
Deal Experience
Looking back on the industry since he entered VC in 2017, Sidberry recalls a time when check sizes were smaller, Series A rounds were less than $10M, and the characterization of the market was fundamentally different to the landscape of 2024.
He fondly recalls his first deal at Forerunner Ventures, which was a MedSpa company called Alchemy43. While he himself was not a customer, it was this experience of learning what it means to be a consumer brand, specifically for a new category, against which he benchmarked all his deals thereafter. Whereas in 2017 MedSpa may have seemed niche, there was in fact a community of consumers who were engaging with these products, and to understand them was an exercise in consumer behavior.
Fast forward to 2024, and Sidberry finds the throughline between his first deal and his latest, which remains undisclosed. He teased a partnership with a company at the center of AI and content distribution, specifically in the gaming space. This deal aligns with a thesis around “small communities that aren’t actually that small”. Investors look for deals and opportunities with a large TAM. However, whether it be MedSpa in 2017 or comics and gaming in 2024, there is a metric of these markets that goes unmeasured when calculating opportunity: the strength of connectivity. Sidberry’s thesis around these smaller, seemingly niche markets, is that their “connective tissue” is just that — a muscle to be flexed, and soon that muscle grows. What he saw in MedSpa he can see in this newer market, understanding that consumers that appear “fringe” are the ones to be watched.
Listeners will note another common thread with this deal in Sidberry’s passion for graphic novels This motif, one of many, underscores the ways in which each experience, no matter how early, has colored Sidberrys’ impressive career as an investor.
Zooming Out: How the Market Has Changed Since 2017
With more than 8 years of industry experience, Sidberry has been witness to the challenges and triumphs of the VC ecosystem since 2017. Sidberry noted that the current struggle to raise a fund is not unlike the struggle which founders face when raising a round. Sidberry predicts that the current stagnation in the VC market will, in time, cultivate a welcomed refresh of the ecosystem.
More specifically, Sidberry noted that with fewer resources flowing through the system, the level of competition, discipline (and their resulting outcomes) rises. After all, economic downturns have, historically, led to paradigm shifting technologies and the emergence of once-in-a-lifetime companies. The most recent example being the economic crisis of 2008, the aftermath of which ushered in the advent of social media.
Sidberry recalls that when he joined the industry in 2017, social media was at the tail-end of being considered “novel”. Companies like Instagram (2010), Snapchat (2011), Music.ly (now known as TikTok) (2016) were finding ways to add value by offering a level of connectivity that was completely new to the market.
So what will be the emerging technology that earmarks the challenging VC market of 2024? The answer here is obvious — Artificial Intelligence (AI). Even in the strapped market, applications of AI have seen massive amounts of funding, garnering over 20% of all venture funding in 2024, according to Crunchbase News. The development of AI will not only revolutionize industries as we know them, but will also shape the future of VC funding as we’ve seen in historically similar cycles of 2001 and 2008.
