One of the most challenging situations in startup/venture capital land is the broken syndicate. It is not a topic that is talked about much, but it is fairly common, particularly for companies that succeed in building a business but falter at achieving escape velocity.
A syndicate is a group of investors that come together to support a startup financially. They tend to be built over time. Some investors get involved with a company in its seed round. Others get involved in a company in the Series A round. And some get involved in the Series B round.
By the time a startup has raised three or four rounds of venture capital, it is likely to have built a syndicate of between three and five venture capital firms and other investors (corporate, strategic, individuals, family offices, etc).
The idea is that the syndicate supports the company financially until it no longer needs capital. That can happen via a sale of the company, an IPO, or achieving profitable operations.
And that is typically what happens in the best situations, when the company executes well and finds that happy financial chart that goes up and to the right with a steepening slope. In companies like that, the syndicate almost always sticks together, and more investors clamor to get into it.
And then there is the company that never really figures out how to build a business. In those situations, everyone around the table, including the founders, figure out how to wind things down, either through a sale of the business, an acquihire, or a wind down. This happens all the time and is generally not a particularly painful process.
But there is a middle ground, where the team figures out how to build a business with customers, revenue, and lots of employees, but then it stumbles and revenues flatten and losses pile up and more capital is needed, often a lot more than the existing syndicate is prepared for. This is when there are management changes, founders depart, and there is a lot of drama.
And holding a syndicate together during the "stumble" is very hard. Some investors are managing huge funds and need exits that will provide hundreds of millions to their fund. When they see that a company will not do that, they often move on. Some investors have small funds and don't have the capacity to fund a company round after round. Corporate and strategic investors can lose interest when a company stumbles and they no longer believe the business is strategic to them.
Those are the "rational" reasons that syndicates break.
But there are other reasons. There is a fair bit of churn inside venture capital firms right now. Younger partners leave to start their own firms, or are asked to leave because they are not producing the expected returns. When a partner who leads an investment inside a venture capital firm leaves, the investment is often "orphaned," and the other partners will pretend to support it but they really don't want to and don't.
Even more upsetting is when a venture capital firm finds another company in the same sector that it likes more, then loses interest in your company and stops supporting it.
All of these things happen to companies who stumble and they happen way more frequently than anyone talks about. It really doesn't benefit anyone to go public with these situations, so they tend to be worked out quietly.
Often broken syndicates lead to early exits, when the founder(s) and remaining investors realize they are screwed and decide to find a home for the business before they run out of gas. Many times these exits are disappointing outcomes relative to the opportunity and they can make for fantastic acquisitions.
Another thing that happens with broken syndicates is recapitalization. This is when the remaining investors reset the valuation in order to bring in new capital, either from their funds or, ideally, from fresh sources of capital. The losers in this situation are the early investors, founders, and investors who walked away.
And sometimes the business shuts down, leaving people scratching their heads. Why did that company, which had lots of customers, revenues, and employees suddenly close shop? Well, the answer is often that their syndicate broke and they could not put it back together.
At USV, we have worked through these stumbles and broken syndicates many times over the years. We often find ourselves in the position of trying to put Humpty Dumpty back together again. We have managed to do that many times. But we don't manage to do it every time.
It is incredibly difficult work, probably the hardest work we do in the venture capital business. And we often are asked why we bother.
We have found that we can make excellent returns when we stick to our conviction around an opportunity and work to restructure the team, the operations, and the syndicate (and the valuation). We also have found that we are rewarded reputationally in the market as investors who are supportive when times get tough. And we believe that it is our job to support companies and the founders who create them.
We wish everyone in venture capital land saw things the way we do, but they do not. And that is the reality of the world we operate in.
Founders need to understand all of this when they put their syndicates together. You should ask around about the investors who want to put money in your company. Look for companies that have stumbled. Get to the people who know what happened in those situations and ask about how their investors behaved. That will tell you a lot.
The bottom line is that syndicates are fragile things. They break. And putting them back together is hard. So figure how to build one that is strong and will stay strong. The best way to do that is to under-promise and over-deliver on the business plan. But you can also do yourself a lot of good by finding resilient investors and getting them into your cap table, so do that too.