Every entrepreneur I know falls somewhere on the spectrum between paranoid to full-blown “the world is conspiring against me” paranoid. This is no surprise because only the paranoid survive. It creeps up everywhere: will a competitor lap me? Will a key employee leave? Will I lose that partnership? I just pitched an investor, are they going to share information with people I don’t want them to? A strategic is trying to acquire us, are they just fishing for information so they can directly compete? The list is infinite. No matter how well things are going, there is always something suspect in the air.

One area where paranoia always crept in for me was when investors asked whether I thought another company was competitive. When building GroupMe and Fundera my answer always defaulted to “Yes, of course.” At GroupMe if someone wanted to invest in a group-buying company, we’d block it because we had “Group” in our name and one day we might converge. If someone wanted to invest in a SMB insurance marketplace, we’d be insulted because we wanted to be the Everything Store for SMB financial products at some point in the next 5-100 years. My feeling was that investors made their bet on us, and anything even remotely adjacent or tangentially related was a blatant affront and off-limits. If they asked, I’d block it. 

Now that I’m on the other side of the table, I think about this a lot. 

When starting Fundera, I actively sought to work with investors who knew about our space. We were building a marketplace/brokerage for SMB loans, and we were relatively new to this world. If an investor had previous exposure to SMB lending it was a plus. Two of our first investors, First Round and Khosla Ventures, had invested in OnDeck Capital, a direct lender that would become an important partner and customer of ours. This was a positive signal to me - they believed in the space. Another one of our investors, QED, had invested in another SMB lender that became an early partner and customer of ours. In no way did I view this as a conflict, it was a positive differentiator. 

But once we had an investor’s money, something changed for me. Whenever they’d try to make a new investment in a direct lending company (similar to the aforementioned ones), I’d attempt to block it, claiming it was competitive. This was irrational behavior. If it didn’t matter before, why would it matter now? I remember when one investor told me he made an investment in a direct lender without asking for my permission beforehand, I was absolutely livid. All I could see was red when he explained their new investment. (The company ended up becoming another important paying customer of ours, and the founder became a friend of mine whose next company I invested in.)

Reflecting on this, it seems hypocritical to feel this way and I’ve tried to piece together why that was the case. When the investment in Fundera (which actually felt like an investment in “me”) followed an investment in a direct lender, I felt validated, as if the investor made a previous mistake and was course-correcting by supporting us. But when the opposite happened, I felt betrayed, like the investor believed they made a mistake and we weren’t good enough. My feelings were real, but my assumptions were wrong. This was not an indictment of me as a person or a loss of belief in the potential of the company itself. It was an action reflective of a growing conviction in the space and a desire to deepen its financial investment in a theme they believed to be important. This was not supporting a competitor, it was strengthening a complement.

I think this will always be a sensitive topic and a tricky area to navigate. Some investors can be very helpful if they have exposure to a space and know the relevant players and industry dynamics. It’s easy to try to present making investments in an adjacent company as a logical and potentially beneficial thing to an entrepreneur, but investors should be empathetic and recognize that entrepreneurs have real feelings and are inherently paranoid about this. I don’t think investors should ask for permission, but they should always ask a Founder's opinion and factor it into their decision-making. At the end of the day, they’re only left with their reputation. For entrepreneurs, it’s important to internalize that these investment decisions are not a critique of them as a person or their business (unless the VC deliberately invests in a direct competitor, then they are asking to be written off). In fact, these actions can be a way of doubling down on your future. It’s hard to separate feelings and perception from intent. These situational dynamics are important and can get messy very quickly. There’s no substitute for putting yourself in the other person’s shoes.