📈 This LP has 62x & 33x Valuation Markups w/ under 10 total investments 📈    

Who are Syndicate LP’s and how do they think about allocating capital into SPV’s?

Today, we are excited to present our inaugural interview with one of our Limited Partners (LPs) exclusively for LMI readers. The objective of this interview is to showcase our LPs and provide them with an opportunity to delve deeper into their identities and investment philosophies as angel investors/LPs in syndicates.

Not many people have a portfolio of under 10 companies with valuation markups of 62x and 33x. This goes against the LP strategy that we would follow and recommend, BUT if you got it, flaunt it (and try to repeat it)!

Let’s share more on this LP…

LP Profile:

Our first LP spotlight is Connor Sentz, an LP of Riverside Ventures who has invested in over 6 deals and has managed to pick 2 outsized (unrealized) winners.

Connor is a Regional Account Director working at the Series C startup Obsidian Security, which is focused on the emerging SaaS Security market.

Connor believes that in the context of early-stage startup investing, the paramount aspect of any deal lies in the leadership team. The team's expertise, track record, and network are crucial determining factors, alongside gaining insights into the involvement of other venture capitalists in the transaction, among other pertinent aspects.

Connor’s Net Worth: Okay, we’re not going to get that detailed, we’ll stop there :)

Check out our interview with Connor below:

What do you do for work and what company do you work at?

Connor: Currently a Regional Account Director working at a Series C startup Obsidian Security, focused on an emerging SaaS Security market.

Where do you currently reside?

Connor: Brand new resident of Charleston, SC after spending 4.5 years in NYC and 6 years in San Francisco.

How long have you been investing in venture capital & VC syndicates?

Connor: My first exposure to venture was at my first company as an employee, Okta, where we were granted ISO's and went through multiple funding rounds led by Sequoia & Andreessen Horowitz. This allowed me to meet Ben Horowitz and Pat Grady which jump started my interest in VC’s. My first seed investment was in 2018 stemming from the capital gained from Okta's IPO in 2017.

What excites you about investing in the venture capital asset class?

Connor: The opportunity! So many market movers are being introduced at such a rapid rate, across all verticals, and it's great to meet with leaders who are identifying disruptors to industries that have already been 'defined'. This is where the value of an SPV comes into play - we would never have access or the ability to invest in these leaders without an SPV.

How many SPV’s/early-stage companies have you invested in?

Connor: I've personally invested in 6+. A couple have failed, and a couple have been (on paper) major successes but it’s still relatively early.

What is most important to you when reviewing deal memo’s and deciding where to invest?

Connor: Leadership team/founders above all in my option. Additionally, I’m particularly interested in natural market growth - social, product disruption, niche markets - that haven't been addressed or can take a % of a total addressable market from the legacy players.

Have you invested in any big winners so far?

Connor: Yep! Loverboy & Pair Eyewear are both marked up significantly, over 30x & 62x from entry valuation.

What made you excited to invest in Pair Eyewear?

Connor: I accessed the opportunity and the founders Nathan & Sophia just weeks before their launch on Shark Tank. They already had some sustainable revenue and were focused on a very specific target audience - kids. After the premier on SharkTank, I was banking on the influx of revenue from the show which would open eyes to the likes of Warby Parker, Luxottica, etc who weren't making competitive products for children, making Pair an acquisition target from the jump. 6-14 year old kids need on average 3 pairs of glasses, face challenges at school, and are lacking an identity - with licensing deals w/ Marvel, Harry Potter, MLB/NBA, Pair was addressing their target market better than any of their competitors. What was unexpected about the success of the company was Covid/TikTok, which coupled with the success of Shark Tank, propelled them to pivot to keep up with demand, and now the majority of Pair's revenue comes from adults, creating a much larger market cap and a larger buying audience who can afford their subscription model.

What made you excited to invest in Loverboy?

Connor: Loverboy was creating a seltzer drink that was based on tea. White Claw/Truly owned the initial market and BudLight/Corona were late adopters - similar to Juul vs large tobacco manufacturing companies Altria/Phillip Morris that never addressed the vaping market until it matured, and had to 'buy in' for $13billion - no one was addressing the taste of Tea. Loverboy’s branding and target audience jumped out at me. Having watched Summer House, market viewership was declining and the show needed to mature. Bravo, to deviate from 'drama fatigue', wanted to introduce Loverboy as an integral part of the season for the founder, Kyle (and Carl). On average, 500k people a week watch Summer House on Bravo - With a very specific target audience, being women. Loverboy caters to the majority of the audience watching the show, which I view as free marketing, and recently has done a great job of capturing shelf space in major retailers.

How many deals do you look to invest in per year?

Connor: Depending on the market, about 3 per year.

What makes you interested to back a syndicate and also a particular deal?

Connor: Trust. Knowing that everyone is in it together - I win, you win, we win. Deal flow and opportunities. Just because you're giving me an opportunity via Riverside Ventures, doesn't mean it’s the right fit for me. Access to thought leaders & founders who know their vision and market better than we ever will. Where they fit, how they differentiate, etc is key. I don't expect SPV's to find the next TikTok/Salesforce, I expect them to find the markets that TikTok/Salesforce aren't focused on to capture market share and have an exit strategy for their initial investors.

When it comes to what deals get me most excited, I care most about the team’s leadership/founders. Their background, knowledge, and connections are super important. Seeing what other VC’s are in the deal is very important to me as well among other items.

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✍️ Written by Alex and Zachary