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Opening the Black Box: Syndicate Investing by the Numbers

Syndicate investing has primarily operated behind closed doors, with limited transparency around lots of the metrics that tell a larger story and are unique to syndicates Today, we're changing that. In this unprecedented deep dive, we're pulling back the curtain on some of our syndicate volume, sharing granular data that investors rarely get to see: our deal volume, average check sizes, LP participation numbers, valuation trends across funding rounds, and the performance metrics that drive our syndicate investment decisions. Whether you're a seasoned angel investor or considering your first syndicate allocation, these insights will provide a clear-eyed view of how active modern syndicates actually operate in today's complex funding landscape.

The analysis shared in this post is based on investment data from Riverside Ventures Syndicate covering the period from January 1,2025 to April 18, 2025.

Since the beginning of 2025, Riverside Ventures has completed 29 investments in a variety of startups, an aggressive investment pace averaging nearly 10 deals per month. 

In this post, we'll be analyzing Riverside Ventures' syndicate deployment details. Our analysis will unpack the numbers behind this syndicate and include things typically not shared such as:

• total investment volume across all deals

• typical SPV investment sizes 

• LP participation patterns per SPV

• the valuation spectrum of portfolio companies

• investment stage distribution from pre-seed to growth rounds

• and additional insights that illuminate Riverside Ventures' unique position in today's competitive venture landscape.

 Total Capital Deployment

Thus far, in 2025, the syndicate has deployed (actually wired) a total of $11,586,628.93 across these 29 investments in just over three months, slightly ahead of pace to what 2024 shaped up to be for the syndicate. 

Investment Stage Focus

The first four months of 2025 demonstrate a balanced private market investment landscape, with equal emphasis on both early-stage and late-stage funding. 

• Early-stage (Pre-Seed, Seed, Seed+) = 37.9% of total funding activity.

• Late-stage investments (Series C, D, F, Pre-IPO, Other) = 37.9% of total funding activity.

• Mid-stage investments (Series A, A+, B) make up the remaining 24.1% of total funding activity. 

The data shows Seed rounds dominating the early-stage category with 9 investments, while Pre-IPO and Series C funding leads the late-stage segment with 4 investments each.

**With 4-5 YCW25 investments, that may skew more seed deals that would not be reflective of other quarters hence the “seed domination” in 2025 to date.  

Monthly analysis reveals a potential shift in investor focus, with January showing the highest investment activity (11 deals) with emphasis on early-stage deals (6 investments), while April demonstrates a clear preference for later-stage rounds with 4 out of 5 investments in the late-stage category. 

This suggests investors may be becoming more conservative, prioritizing established companies closer to liquidity events (or at least perhaps how I, the syndicate lead, perceive LPs at present). Notable late-stage investments include a Series D round and multiple Pre-IPO investments, indicating continued interest in AI and cryptocurrency sectors despite broader market uncertainties.

Investment Sizing Strategy

The average investment size metrics provide valuable insight into Riverside's deployment strategy. 

• Total Deployment (Jan 1 to April 18) = $11.59M

• # of Deals = 29

• Average size SPV = $399,539

With a total deployment of $11.59M across 29 deals, the simple average investment comes to approximately $399,539 per deal. This check size positions us as active participants in early rounds without taking overly concentrated positions in any single company. That said, this is the norm for syndicates as we are not deploying from a pool of capital like a fund, so concentration is not something that is thought about in a comparable way to venture funds. 

Valuation Trends

The valuations of companies invested in thus far show extreme variation, ranging from as low as $10 million (pre-launch company) to $58 billion. The median valuation is approximately $450 million, significantly lower than the average of approximately $5.4 billion, indicating the distribution is heavily skewed by a few extremely high valuations. 

My guess is that many folks assume our check size ( avg. $400k per deal) is best suited for seed deals and therefore syndicates are more likely to be heavily concentrated there, however it highlights the appetite and ability to get into later stage opportunities as the median valuation is approx $450M.

The top three valuations (all AI companies) are $58B, $39.5B, and $5.8B - highlighting the premium currently placed on artificial intelligence startups… and where LPs typically invest larger commitments.

Early-stage companies appear to cluster around the $20-50 million range, with 4 startups all valued at exactly $20 million, suggesting this might be a common entry-point valuation for seed stage companies. 

Limited Partner (LP) Participation

The average number of LPs across all deals is 26.5, with substantial variation in LP participation. The largest LP participation seen since the start of 2025 was 85 LPs, followed by 66 LPs, and another with 61 LPs in one deal, and then the next with 49 LPs in a deal. These high-participation deals suggest significant investor interest and potentially larger funding rounds and later-stage companies. On the other end of the spectrum, the 3 deals with least LP participation have just 7, 8 and 8 LPs respectively. This wide range (from 7 to 85 LPs) indicates varied investor appetites across different startups, with most companies falling in the 15-30 LP range.

Conclusion

Our 29 investments totaling over $11.5M suggest a deliberate strategy focused on building a diversified portfolio across multiple sectors and stages that allows for LPs to make investment decisions on building their own private market/venture capital portfolio.

As the year progresses, it will be interesting to observe whether this pace of investment continues or if we shift more toward later stage or alternative directions.This level of activity from a single syndicate also reflects a broader ecosystem trend: while large institutional rounds may still be challenging to close, networks of individual investors are helping play a small role in funding promising early-stage companies, potentially reshaping the venture landscape for years to come.

This analysis is based on investment data from Riverside Ventures Syndicate covering the period from January 1 to April 18, 2025.

If you enjoyed this article feel free to view our prior articles on adjacent topics 

• Bridge Rounds; A VC’s Dream or Nightmare?

• The Challenges of Relying on Public Comparables for Valuing Your Startup

• Why Revenue ≠ Revenue! How to See Past the Blanket Revenue Multiples Put on Companies

Last Money in is Powered by Sydecar

Sydecar empowers syndicate leads to manage their investments more effectively. Organize, manage, and engage your investor network effortlessly with Sydecar’s management and communication tools. Their platform also automates banking, compliance, contracts, tax, and reporting, freeing up syndicate leads to focus on securing deals and strengthening investor relations. Elevate your syndicate operations with Sydecar.

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✍️ Written by Zachary and Alex