The two best cap table management software providers right now are Carta and Shareworks (formerly known as CapShare, now owned by Morgan Stanley). Shareworks used to have a free version, but now it starts at $3 per month. Carta is more expensive, starting at $2800.00 per year, but it is a good solution.
For many reasons, it’s very important for a young company to keep careful track of equity ownership and stock options. Most importantly, it’s very likely that the majority of your employees (and founders!) are working hard to try to make their ownership and options worth something - so you owe it to them to keep careful track of each and every share. Your cap table matters, so pick a good software vendor to help you get it right and keep it straight.
How startups initially set up their ownership split between founders is a question that we get a lot! Here are some important things to think about as you set up your capitalization table.
Tips for setting up your cap table
Founders should always take common stock, everyone on the management team should get common stock. You don’t want to have one of the founders having preferred and a liquidation preference over everyone. That’s just weird, it can lead to misaligned incentives down the road and VCs will probably not like it.
The second thing is you really need to have is a vesting period on everyone’s shares. What this does is that it protects the founders that end up staying with the company for many years from some of the other founders who might leave after a year or two. By having a vesting period, (typically it’s a four-year or a five-year vesting period) where your ownership vests, if it’s a five-year vesting period you vest 20% of your stock every year and usually there’s a one-year cliff, so you vest 20% after the first year and then you do the rest of it on a monthly basis.
But what that does is if someone decides they need to leave because they don’t believe in the vision anymore, they can leave and their remaining unvested equity can be used in the stock option pool to attract other senior-level, really strong talent to help the company be successful. What you don’t want is to have everyone vest everything on day one and then one of the two founders decides they’re going to go live in Hawaii and take off and not actually do any work for the startup and not advance the cause. Because then a big piece of your cap table is owned by someone who isn’t helping the business.
So vesting periods are really, really important. It’s very friendly to the founders that are gonna stay there, it’s also something that VCs want. When they invest in a company, they’re really investing in the founders; there may be some great technology, maybe it’s a great vision, but venture capitalists know that the founders and the executive team are the ones that are going to make it happen and bring the company to success. So they want to make sure the founders are emotionally and financially vested in the company.
Now there’s another thing that gets discussed, it’s kind of a tough topic, but sometimes you do not want equal ownership between the founders. Not everyone should have the same percent of the cap table. Now this is the case when one of the founders is going to make a more significant contribution than the others. A typical founding pair might be one kind of business or sales or strategy person and a technical founder. That’s kind of the combo we see quite a bit at Kruze Consulting, but maybe the technical person was recruited late to the idea and they weren’t the person that really took the germ of the idea and really built it out. Or maybe everyone knows that the CEO’s is going to do a lot of product stuff while also raising money and doing a lot more work or may be a lot more important to the company’s future.
It’s much, much better to have that conversation early in the startup. You don’t want a lot of resentment building over the years where someone feels like they didn’t get their fair share or someone feels like maybe the cap table being equally split wasn’t the right amount because they’re doing so much more. This is a really tough conversation to have, we really recommend having it on day one or day two instead of day 365, where tensions could be much higher. Do it right away, before you and your co founders really start working on the project.
Feel free to lean on your angel investors for advice here or even your CFO firm like Kruze. We have helped hundreds of companies manage their cap tables (using software of course!) and see this a lot - our basic advice is to align the ownership amounts with the expected contribution amounts.
The vesting period and these ownership splits are really all about doing the right thing for the company and making sure everybody is aligned. These honest conversations between founders really sets the stage for you to have many more honest conversations down the road. There’s is going to be a lot of tough stuff that comes up over the years and having just this first one around the ownership split will really help you and be beneficial going forward.
We have one other pro tip for all the founders out there. This isn’t about the ownership split but instead is for your taxes - file your 83b filing with the IRS within 30 days of founding the company and buying your founder shares, it is so important. Make sure that it is certified mail, keep that receipt for the rest of your life. You do not want to screw up the 83b. This happens occasionally, it is really hard to reverse. The 83b basically gives you a really low cost basis and you can get capital gains on all your appreciation after that. It should save you a ton in taxes.
So have the tough conversation with the ownership split, have the tough conversation around the vesting period, and then after you have that conversation shake hands, hug, and then fill out that 83b form and walk over to the post office and mail it together.
Once you go beyond the founders, it’s time to get a cap table management software to help you keep careful track of everyone’s ownership and vesting. Again, Carta and Shareworks are the two biggest players in the space.
No discussion about cap table management would be complete without going over what a vesting period is. For a typical stock option plan, a vesting period is the amount of months/years that a startup employee must stay employed at that startup in order to be allowed to exercise their stock options.
A vesting period or schedule prevents a startup employee from leaving the company early-on and taking a large piece of the company’s equity, leaving no room on the capitalization table or options pool to hire another employee.
In Silicon Valley, the typical vesting schedule is over four years, with a one year cliff. More notes on stock vesting:
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