StrictlyVC’s INSIDER Series: Silicon Valley’s Best-Kept Secret

The StrictlyVC Insider Series has quietly become one of the top tech events in the Bay Area. Event series producer and moderator Connie Loizos, known for her must-read daily VC newsletter StrictlyVC, also serves as Silicon Valley Editor for TechCrunch, a division of AOL. Notwithstanding her high-profile institutional affiliations, the event itself is unusually warm and hospitable. Think U2 playing late-night in a Los Angeles club that seats only 125 people.

Credit: StrictlyVC Flickr

StrictlyVC events always sell out weeks, even months, in advance; to date Connie has only held two per year.  ”We keep it small and intimate, that’s the key,” explained one of Connie’s colleagues, who helps organize the events.

There’s something special that happens when Silicon Valley icons speak informally to such a small group of people. It relaxes the conversation and gives the audience a sense of participating in the talks. Last Wednesday’s event was no exception.The lineup included a typically impressive range of founders and VCs, from the CEO of a LinkedIn challenger to the founder of a little known billion-dollar pharma startup. After Connie’s opening remarks, the first guests onstage were Aileen Lee, founder of Cowboy Ventures, and Amy Chang, co-founder and CEO of the professional database site Accompany. In what she jokingly called a “two-Asian-women show,” Lee questioned Chang about her background, Accompany’s founding concept, and the company’s technical challenges and rapid growth.

Aileen Lee (left) on stage with Amy Chang (right) | Credit: StrictlyVC Flickr

Accompany solves a narrow but pervasive problem faced by professionals, that of walking into an important meeting feeling clueless about the person with whom you are meeting. Chang spoke of being in that situation herself and wishing she had a folder of relevant information she could review in time for the meeting. Although LinkedIn profiles provide some of that information, Accompany offers its subscribers a broader range of data, ranging from up-to-the-minute news items to recent activities and social media threads, packaging it into a tailored “dossier.” Accompany’s stated goal of creating the world’s second-largest professional database after LinkedIn may be a bit ambitious for a three-year-old startup, but the audience seemed impressed by both Chang herself, who had previously built Google Analytics from scratch, and the fact that Accompany had already raised $40 million in venture capital.

Next up was Bradley Tusk, founder and CEO of Tusk Holdings, the surprise “break-out” guest of the night. Tusk’s background isn’t typical in Silicon Valley; he spent most of his career in politics, most notably as Michael Bloomberg’s campaign manager. His first significant interaction with the tech industry came when he was asked to help Uber fight the taxi driver backlash in New York City. At the time, Uber did not have sufficient cash to pay a consultant of Tusk’s stature, so he agreed to take his fee in equity.

Bradley Tusk interviewed by Connie Loizos | Credit: StrictlyVC Flickr

Lucky call! It’s been estimated that he ultimately walked away with $100 million in equity from that deal. The experience prompted Tusk to take on other high tech clients for equity, including FanDuel and Tesla, that are also aiming to navigate highly regulated or politically sensitive markets. Tusk clearly relishes his unique ability to move between politics, technology, and investing, and he had outspoken, occasionally brash, opinions about all of them. In addition to discussing his work as a political-strategist-turned-VC, Tusk collegially bantered with Connie about everything from the missteps of the Trump administration to his assertions of liberal bias on the part of the New York Times. Tusk is clearly positioning himself and his holding company as the go-to fixer for tech companies: Silicon Valley’s no-bullshit guide through the unfamiliar landscape of politics.

The second surprise guest of the night was Vivek Ramaswamy, founder of Roivant Sciences. Like celebrity-turned-pariah Theranos CEO Elizabeth Holmes, Ramaswamy is a millennial biotech entrepreneur. In contrast to the high-profile Holmes, however, Ramaswamy has quietly raised more than $1 billion for Roivant and has already taken one of its pharma entities, Axovant Sciences, public.

Vivek Ramaswamy interviewed by Connie Loizos | Credit: StrictlyVC Flickr

Ramaswamy was interviewed onstage by Connie herself, and spoke knowledgeably about a wide range of subjects: from the failures of the existing process for testing and bringing new pharmacological products to market to the economic case for focusing on drugs that solve rare conditions ignored by established pharma companies. Ramaswamy exhibited a poise unusual among 31-year-olds, and he demonstrated a unique ability to take extremely complex pharmaceutical issues and distill them down to clear terms any business person could understand. Whether or not his company becomes the next Berkshire Hathaway, as Connie suggested it might in her introduction, Ramaswamy is clearly taking on an audacious set of endeavors that, if successful on the scale that he envisions, could change the economics of bringing new drugs to market.

Emily Weiss interviewed by Eric Liew on stage | Credit: StrictlyVC Flickr

Another founder at the Insiders’ Series was Emily Weiss, founder of Glossier, the no-frill cosmetics and skincare brand that has developed something of a cult following among millennial women. Weiss was interviewed by Eric Liew, general partner of Institutional Venture Partners, the VC firm that co-led Glossier’s $24 million Series B. Weiss, who started a blog called “Into the Gloss” because she was frustrated by the lack of beauty product-centric media, expanded into products with the aim of starting a “beauty brand you want to be friends with.” Glossier communicates with customers directly via blog and Instagram, to the extent of foregoing a typical company funding announcement and sharing it instead with users in its newsletter.

The last talk of the night was a wide-ranging professional and personal conversation between Brad Feld of Foundry Group and Semil Shah, founder of Haystack.The co-founder of Techstars and several renowned VC firms, Feld spoke about his early startup career, his experience in venture capital, and the cyclical nature of high tech investing, including his up-close-and-personal experience with the 2000 dot com 1.0 crash. 

Brad Feld interviewed by Semil Shah on stage | Credit: StrictlyVC Flickr

Disheartened at the prospect of facing yet another day of bad news and rejection, Feld recounted how his trusted mentor had pointed out, “Well, they can’t kill you and they can’t eat you,” which gave him just enough of a nudge to make it through another day. Feld also spoke candidly about his introversion and struggles with depression, which he has written about in his widely read blog, “Feld Thoughts.” When asked what he was most proud of during his career, Feld said he took the greatest pride in the relationships he had cultivated with his business partners and close associates over the course of many years. Like Bradley Tusk, Feld was outspoken and extremely funny — but he also communicated in a way that echoed and underlined the intimate feel of the entire evening.