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What does a VC want to see in a cap table?

I'm looking for some objective insight into a cap table issue that's come up for our company as we look to raise a bridge seed round before our series A. We're a real estate fintech company in the investing space, our product is launched and in good shape (though always improving), we've started building some momentum but are still pre-proven traction. We're pivoting the direction of the business a bit and the bridge seed round should help us prove traction on that concept relatively quickly if all goes well.
Our company received initial funding from the key executives of a mid-sized real estate company (less than $1m) in the form of a convertible note at a $6m cap. In addition, the same group of investors received vesting common equity in the company (40% total) with the idea being that our business would be a true joint venture with them. We would use their large contact list (40,000) to find initial investments and, more importantly, initial investors and the sweat equity partners would work 1-2 days per week on our company and that amount would grow over time. In addition to their cash investment in the company, they also contributed some existing tech IP that they had started building before we came together. Since launching we have frequently used our partnership with this larger, more established company for PR purposes.
Fast forward about 9 months to present day. Despite best intentions the initial investors haven't been able to contribute to the day to day work of the company in a meaningful way. The initially contributed IP is largely irrelevant once we got into real, full time product development. The contact list provided us with an initial base of users (about half of the total we've acquired in our few months of business) but hasn't catapulted us to the significant headstart on the customer side that any of us anticipated. We continue to mention our partnership with this company on our site and PR materials but, as we broaden our marketing outreach for new customers, the affiliation becomes less powerful (they are pretty well known within the industry but not outside it).
We heard from one of our initial employees who has substantial venture experience that outside investors will see this situation and want to "fire" these initial investors so their common equity doesn't vest. We discussed restructuring the cap table so that these investors no longer have vesting common equity. To partially compensate them for this loss our idea was to lower the valuation cap on our note from $6m to $4m, increasing the value of their actual cash investment. The initial investors were reluctant to restructure without evidence that this would be a real issue for outside investors.
Recently we've been engaged in fruitful discussions with a very experienced angel investor (100+ companies). He loves our team and the new direction for our business but is ready to walk away from the opportunity because he thinks the current cap table situation won't work in the long term, either for raising additional money for the company or for healthy management and operations.
It would be really helpful to get feedback on how common his view is going to be and how much of a hindrance to raising outside investor capital our current structure will be. Our initial investors, fairly, want additional opinions before any kind of significant restructuring.
Our company received initial funding from the key executives of a mid-sized real estate company (less than $1m) in the form of a convertible note at a $6m cap. In addition, the same group of investors received vesting common equity in the company (40% total) with the idea being that our business would be a true joint venture with them. We would use their large contact list (40,000) to find initial investments and, more importantly, initial investors and the sweat equity partners would work 1-2 days per week on our company and that amount would grow over time. In addition to their cash investment in the company, they also contributed some existing tech IP that they had started building before we came together. Since launching we have frequently used our partnership with this larger, more established company for PR purposes.
Fast forward about 9 months to present day. Despite best intentions the initial investors haven't been able to contribute to the day to day work of the company in a meaningful way. The initially contributed IP is largely irrelevant once we got into real, full time product development. The contact list provided us with an initial base of users (about half of the total we've acquired in our few months of business) but hasn't catapulted us to the significant headstart on the customer side that any of us anticipated. We continue to mention our partnership with this company on our site and PR materials but, as we broaden our marketing outreach for new customers, the affiliation becomes less powerful (they are pretty well known within the industry but not outside it).
We heard from one of our initial employees who has substantial venture experience that outside investors will see this situation and want to "fire" these initial investors so their common equity doesn't vest. We discussed restructuring the cap table so that these investors no longer have vesting common equity. To partially compensate them for this loss our idea was to lower the valuation cap on our note from $6m to $4m, increasing the value of their actual cash investment. The initial investors were reluctant to restructure without evidence that this would be a real issue for outside investors.
Recently we've been engaged in fruitful discussions with a very experienced angel investor (100+ companies). He loves our team and the new direction for our business but is ready to walk away from the opportunity because he thinks the current cap table situation won't work in the long term, either for raising additional money for the company or for healthy management and operations.
It would be really helpful to get feedback on how common his view is going to be and how much of a hindrance to raising outside investor capital our current structure will be. Our initial investors, fairly, want additional opinions before any kind of significant restructuring.
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