Masterclass: Inside the Deal—Why We Said Yes to Circle

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  Speaker 1:
  Hey everyone, thanks for joining us for this VC masterclass Inside Circle’s Blockbuster IPO. Let me first advance the slide and give you a little bit from our lawyers. As with most things here—

   On the disclosures page, we’ve got to pause to remind everybody we’re speaking today about Alumni Ventures and our views on the associated venture investing landscape. The presentation is for informational purposes only. It is not an offer to buy or sell securities, which are only made pursuant to the formal offering documents to the fund. Thanks so much, and you can read these in more detail—

   At avfunds.com/disclosures. Alright, let me do a quick introduction of myself.

   Hi, I’m Chris Sklarin, Managing Partner at Alumni Ventures. I’ve been with Alumni Ventures since about 2017 and have been a venture investor since about 2002–2003 when I got out of business school. Prior to that, I was a software engineer and sales engineer for a bunch of companies after MIT in the late eighties and through the nineties. I saw several IPOs. The company I worked for was bought three times. One of the companies was ranked Inc. 500 number one, which was all very exciting on the entrepreneurial side.

  Then I went off to get an MBA at Berkeley, came back east, and started up with a seed fund. I was with them for several years, then joined a couple other venture firms, a healthcare accelerator, and most recently was a later-stage venture investor before I joined Alumni Ventures here in Boston in 2017. So happy to be here today and talking about—

   This interesting investment in Circle: what Circle is, why we invested—

   How we got in, and a little bit about the post-IPO journey here and the validation. That’s what we’ll go through today.

  Quickly, just about Alumni Ventures to get you level set: Alumni Ventures was founded 11 years ago in 2014, and we offer individuals an opportunity to own smart, simple venture capital portfolios. It’s really the only and best way I’ve seen for individuals to get into the venture market.

  Today, we’ve raised over $1.4 billion from 11,000+ individual investors and have invested capital in 1,600+ current and historical portfolio companies. Alumni Ventures is one of the most active venture firms globally and one of the largest domestic venture firms for individuals.

  We are comprised of about 120 people, 40 or so of whom are investment professionals located in our Manchester Venture headquarters and offices for the venture investor folks—

   In Boston, New York, Chicago, and Menlo Park. Accomplishments to date: we started—

   Off with just a couple of very small alumni funds. After Dartmouth, we added MIT, Harvard, and Yale as the next cohort, and we’ve since grown this to over 20 alumni funds.

  We also have funds for focused areas like health tech, a women’s fund, or a seed fund. I think we’re now the leading venture firm for individuals in the world.

  We have a large, very engaged community in entrepreneurship, a great team, a top content brand, and we’re always publishing blogs and videos. I think we’re a very robust sourcing engine.

  We put out this report, the Apex 50, which you can go to our website and check out. It highlights 50 standout companies from the over 1,600 portfolio companies we’ve invested in. These are the ones for this year that we really feel are outstanding contributors to making the world a better place and, hopefully, will bring us tremendous returns down the— road.

   Part of the hallmark of our model is that we’re always a co-investor. This is just a quick sampling of investors we’ve invested alongside. Some names you may be very familiar with.

  We also invest alongside very interesting sector funds that may be expert in particular areas you may not have heard of. This gives you a good idea of some of the companies we’ve invested alongside. But we really have many, many co-investors and work very hard to do a good job of finding great companies and understanding why they’re partnering with those great investors—making these marriages happen.

  Then we can hopefully put in 5, 10, maybe 20% of a venture round.  So—

   Let me jump to Circle here. Circle is a very, very interesting company. It was founded in October 2013 by Jeremy Allaire and Sean Neville. They’re a really interesting company, aiming to build the digital pipes for cryptocurrency.

  Right after we invested—in 2018 or so—they introduced the US Dollar Coin (USDC), which has become a leading stablecoin in the marketplace. It’s used for payments, trading, and serves as core infrastructure in blockchain finance.

  The story here, in summary, is a journey from Bitcoin startup to FinTech powerhouse. Founded in 2013, their early mission was enabling Bitcoin payments. They operated a crypto exchange platform and, right around the same time we invested, launched USDC in 2018. They aimed to become a stablecoin infrastructure leader, and we’ll talk about this journey.

  They’re now the world’s second-largest stablecoin. At the time of this report, it had $56+ billion in circulation. In June 2025, Circle raised $1.1 billion during its New York Stock Exchange debut, reaching a valuation of $6.9 billion. We’ll get into more details as we move through the presentation.

   About how this all happened as we go through the presentation—so, Circle: what sets—

   Circle apart is infrastructure, not hype. We were really excited about Circle when evaluating them. They created USDC, now the world’s second-largest stablecoin with 27% market share as of their IPO on June 5.

  They’re not trying to disrupt banks with a fancy app. Instead, they’ve built something far more fundamental: digital pipes for digital dollars.

  From the outset, they had a compliance-first DNA and received a BitLicense in 2015, embedding regulatory trust into the foundation of the company early on. Their mission from day one was enabling digital transactions, and it’s always been independent of any specific token or platform.

  Around 2017, as crypto hype was surging, we launched our first blockchain fund. That fund led our investment into Circle in 2018, alongside Goldman Sachs and General Catalyst.

  The 2018 market crash created a rare value point in crypto infrastructure and digital finance because companies were still being built but at better valuations. While others ran for the hills, we saw long-term potential and decided to invest in Circle and other crypto companies.

  Jeremy Allaire, the founder, had already taken two companies public: Allaire Corp (IPO 1999) and Brightcove (IPO 2012). An experienced entrepreneur with both public and private market growth experience was a big draw.

  We also had a strong network in Boston, which gave us the opportunity to get a small allocation alongside Goldman and General Catalyst. Having those co-investors de-risked the opportunity for us, as did backing a proven founder.

  Jeremy often said he wanted to build a lasting internet technology platform—a digital infrastructure company for the long term. That was exciting, and obviously, he—

   Was aiming for a big outcome. So, Circle’s journey to IPO—

   From our 2018 investment to now, seven years later in 2025:

  • They launched USDC with Coinbase.

  • From day one, they prioritized compliance and institutional partnerships.

  • This focus drove significant growth in USDC circulation, especially with rising institutional demand.

  • They secured key partnerships, including Visa.

  • They maintained trust through rigorous regulatory engagement, even during volatile crypto markets.

  Notable moments included:

  • Successfully navigating the SVB crisis in 2023.

  • 2024 financials showed $1.68 billion in revenue and $156 million in net income.

  • In June 2025, their IPO priced at $31/share, opened at $69, and peaked at $298.

  Even though the price has since come down from that peak, it’s still far above the IPO pricing.

   So pretty substantial growth since then. Let’s talk about our diligence process, the risks—

   And how this fits into our fund.

  Key in our analysis was targeting companies in emerging technology. In crypto and finance, infrastructure providers often capture more stable, long-term value than consumer-facing apps.

  Circle wasn’t just an app disrupting banking—it was providing the digital pipes carrying transactions. This infrastructure play meant less churn and less competition for user attention.

  We also valued their proactive regulatory engagement. They decided to be regulation-first and upfront about compliance, which builds trust with companies joining them.

  Big institutions could more readily adopt USDC because Circle focused so heavily on compliance.

  Backing Jeremy and his proven team was another strong point—he’d already taken two companies public.

  And remember, this was during “crypto winter.” We were contrarian but disciplined, investing in crypto infrastructure at a time when many fled the space. We passed on many opportunities that year but decided—
  Yes, we’re going to go in and get some money to work. So how do we find similar opportunities?

  
  This wasn’t just one investment. Alumni Ventures has 1,600+ portfolio companies, and Circle is one of them.

  We’re diversified across sector, stage, and geography. We focus on long-term, durable businesses—not hype-driven cycles—and back founders who can execute through various market phases.

  Important attributes: we’re always a co-investor. We don’t write term sheets or set pricing. Sometimes we turn deals down after investment meetings.

  Generally, we rely on the diligence of the lead venture firm we’re co-investing alongside. We talk to management about why they chose that firm, and we talk to that firm about why they chose the management team, doing our own diligence to get our small allocation to work.

  Venture has many moving pieces, but we’re often thesis-driven in our sourcing. I look at deals across the MIT ecosystem. My colleagues cover other alumni ecosystems. We also monitor different technology markets, always watching for dislocations that can—
  Create good entry points for us as investors. So a little bit now onto how we find the—
  Next big opportunity. Circle was a great one and hopefully it continues to do well, but the next opportunity could be in any number of different emerging areas. We’ve listed a few here:

  • AI infrastructure: Building core tools that power the next generation of applications. Everyone is using AI more and more since that last ChatGPT moment a couple of years ago. We’ll continue to prioritize compliance, scalability, and enterprise readiness. The regulatory landscape is a parallel to what we saw with Circle.

  • Proven teams: We’ll continue to look for teams with deep domain experience—people who’ve been there and done that before in entrepreneurship and are now moving into the AI space.

  • Quantum computing: Both hardware and software infrastructure plays are of interest. We’re looking for long-term intellectual property with regulatory moats and strong partnerships with major strategic and government players. Quantum computing will be one of the big enabling technologies—not necessarily this year or next, but in 3, 5, or 10 years, it will play a huge role in our computing landscape.

  • Climate tech solutions: We’re looking hard at climate tech. There are many investment theses in and around this space. Both our regular alumni funds and focus funds like our Deep Tech Fund have climate tech as a central thesis. They address moats like regulatory, institutional sustainability, and policy mandates.

  Again, we seek results-driven business models with experienced teams who understand how to navigate complex regulatory frameworks shaping climate tech.
  Now, what are the risks and future outlook?
  While Circle’s IPO represents a significant milestone, be aware of ongoing risks in the market. Digital assets are still in flux, particularly for Circle.

  There are potential headwinds and tailwinds that could help or hurt the company. Recently, we’ve seen government actions cause Circle’s stock to shoot up or drop down. Hopefully, the price remains high when we exit our lockup at the end of the year.

  There’s also rising competition. Traditional institutions are entering the stablecoin space, and Circle must compete with these large players.

  Technology shifts present another challenge. Blockchain infrastructure is still evolving, and Circle must adapt as needed.

  Finally, market volatility: public market appetite for crypto and crypto-adjacent companies may fluctuate. We manage this risk, and once we’re through the lockup period, we’ll sell our position and return cash to our investors.

  Despite these risks, as the slide says, Circle’s market debut proves that regulated crypto firms can scale and thrive within the traditional—

  
  Financial framework that’s out there. So in conclusion—

  
  The power of being patient and disciplined with our capital: Circle was not a speculation play. It was infrastructure with regulatory foresight.

  We entered this deal to benefit from their building of digital pipes. Our conviction was rooted in Jeremy Allaire’s leadership and focus on compliance, combined with good market timing.

  I believe the next decade will reward investors who apply this disciplined approach to emerging sectors, like the ones listed earlier. We’ll keep looking for founders building the pipes for whatever—
  Tomorrow’s tech economy brings. So, we’d like to be your venture partner.
  Let me jump ahead to information about our funds and investor profiles.

  We have a range of investors who invest with us—most of them individuals. We’ve broken them into five groups: tech enthusiasts or venture-curious individuals, legacy builders, trophy hunters, or asset allocators. You choose which bucket you fall into.

  We have products that appeal to everyone. There are two ways to build your portfolio:

  • Join a fund: We have many funds available. Visit av.vc/funds to see all options.

  • Invest deal-by-deal: Select individual companies you’d like to invest in. We’ll share diligence materials, review deals one by one, and you can decide for each.

  Many investors do both: they join one or more funds and supplement with syndication deals. This approach offers diversification more quickly since funds have 25+ companies each.
  So, ready for next steps? I think we’re going to pause—
  Here and take some questions. I’ll scroll through the web portal to look for questions.

  You can scan the link on the left-hand side of the screen to view fund materials and join a fund. You can also join the AV syndicate by scanning the link above that.

  If you’d like to talk to Dan, Stacy, or Darren, our senior partners, you can schedule a call using the QR code in the upper right corner of the screen. They’ll discuss your fund and syndication options.

  If you’re already an investor with us, Stephanie or Hillary can be your first call. They can review your portfolio, discuss performance, and help with any administrative questions or tasks you have.

  I’m just going to scroll down here and find some Q&A. Here’s a good first question:

  Question: Can you share more about Alumni Ventures’ process for exiting a public company like Circle?

  Answer: Yeah, sure. That’s a great question. The company went public in June, and our stock is typically tied up in a 180-day lockup period. So think of June through about December 5th. Sometimes lockups can end a little earlier, depending on restrictions tied to announcements. It could potentially end by the end of November, but essentially, by the end of the year, we should be able to sell that stock.

  Once that happens, our routine exit committee will figure out how we want to sell it. We’ll probably sell it in public markets over a period of two to four weeks, with the help of a broker to ensure it’s done in an orderly fashion. That helps us turn the stock into cash and send that cash back to investors. Typically, if we get the cash back in Q4, we return it within about 45 days after Q1 starts the next quarter.

  Question: How do the mechanics work to receive funds back for an investment like Circle if I invest through an IRA?

  Answer: That’s a great question. If you’ve invested in an IRA with us through one of our partners, your IRA is “for the benefit of” you as the investor. Any investment proceeds we return from that IRA investment will go back into that IRA. You can then reinvest it in a new Alumni Ventures fund or in something else your provider offers.

  You can’t personally benefit from IRA funds until you retire, per IRS rules. So any proceeds must stay in the IRA for future investments. If you invested with cash, the investment proceeds would return to you as cash.

  
  That’s an IRS rule—you just can’t benefit from that IRA until you retire.

  Question: How do you get allocation in oversubscribed rounds led by top VCs?

  Answer: Great question. We work really hard—like any sales process—with management teams and co-investment partners to prove our value. It’s not necessarily about the size of our check, but about our network and expertise.

  For example, the Castor fund I manage for MIT alums has 30,000+ alumni in its network. Across Alumni Ventures, we have an expert network of 5,000–10,000 people. These connections help management teams understand the value we bring, which helps us gain access to deals.

  Our checks can range from a few hundred thousand to a few million dollars, and sometimes we do syndications to bring in larger amounts. But really, management teams love that they can give back to their alma mater, investing alongside alumni investors.

  Question: Do you have internal sector specialists, or are all AV investors more generalists?

  Answer: That’s another great question. Our funds are often generalist funds, but we also have sector-specific funds. Our investors are very T-shaped, meaning they have broad capabilities plus deep expertise in a specific area.

  For example:

  • One investor might have deep expertise in behavioral and consumer behavior.

  • Another could specialize in deep tech, including nuclear or other advanced tech.

  • Others might focus heavily on AI and computing infrastructure.

  Each investment team usually has three or four individuals with deep experience. We also leverage our expert network to bring in additional diligence and support for companies—for example, on market panels or pitch practice sessions.

  So, it’s a mix: generalist funds with investors and experts who have strong, specialized knowledge. On the focus fund side, healthcare funds are heavily healthcare-focused, women’s funds are centered on women-led companies, and so on.

  If you visit av.vc/funds, you can explore all our funds and see the diversity of our offerings.

  Thank you all very much for attending the webinar. We’re really pleased we could talk about Circle’s IPO and the broader venture landscape.