Why I haven't raised any funds so far

The story of Intercom raising a $23M series B round, bringing their total capital raised up to $30M, was in my inbox this morning.

Eoghan, Intercom’s founder and CEO, and I have a little bit of history. In early 2011, shortly after I’d left my family in Denmark to pursue a new life in the US, Eoghan and I were both renting a room near Alamo Square Park in San Francisco. He was working on Intercom (which wasn’t named Intercom at the time), while I was working on Simplero (which wasn’t named Simplero, either, at the time).

Since then, Eoghan has grown Intercom to a team of 47 and made some pretty impressive hires, while Simplero is essentially a one-man operation (I have a part-time supporter and have a full-time developer starting next month, but most of it is on me). Simplero is bootstrapped, financed off of revenues, money made through other sources, and a line of credit.

I’ve thought about raising funds many times, but always ended up not doing it. I have lots of “great” arguments - wanting to “keep control”, scary stories about founders being kicked out, 37signals-envy, “fundraising takes a lot of time and effort that is taken away from focusing on product”, and on and on. But they’re mostly excuses, not reasons.

The real reason has been my strained relationship with authority. I’ve always had a difficult relationship with my father. Felt like I was wrong, unwanted, in the way, and that there was no level relationship - either he had it his way and I suffered, or I severed the connection and did it my way.

But recently, that has changed. My dad has volunteered to step in and support me financially in my application for an E-2 visa, and in that process, we’ve completely healed our relationship. We’ve been able to have conversations where I can ask him for input and advice, while we both recognize and respect that the final decision lies with me.

The healing of that relationship with the primary authority in my life has suddenly opened up the possibility of acquiring investors. I can see now that they can actually be allies and partners, not adversaries. Yes, they have the money, they will have board seats, but both parties need each other, and both parties can respect each other, as we’re playing our different roles.

I also read Nick Bilton’s story about Twitter, and even though founders were kicked out, it didn’t scare me. Twitter turned out all right in the end. It seems like the investors actually cared about what Twitter could become, in their eyes, and not just pure dollars and cents. That would be a fear of mine, that it’s all about taking shortcuts to an IPO and then sell, rather than build a solid company for the long haul.

So I’m open to funding. But what makes me hesitate?

I’m afraid. And given the fear, it’s much easier to just keep doing what I know well, which essentially boils down to writing more code and answer more customer support tickets.

What am I afraid of? Many things, most of which is bullshit. Here’s a list:

  • I’m afraid of losing control
  • Afraid of being pressured by people (employees, investors) wanting things (decisions!) from me
  • Afraid of being overwhelmed
  • Afraid of being squeezed out by the momentum of what I create because I cannot keep up
  • Afraid of fucking it up
  • Afraid of letting my customers down because I fuck it up
  • Afraid of wasting the money I get
  • Afraid of being rejected
  • Afraid my vision as good as I think it is
  • Afraid of feeling stupid and being the person who doesn’t get it, because the other people in the room are smarter
  • Afraid of being betrayed by someone I let into my business
  • Afraid of having to grow up and be more responsible
  • Afraid of hiring stupid people, or just people I don’t enjoy working with
  • Afraid others aren’t going to pull their weight, do their part
  • Afraid I won’t like the new life style it will entail
  • Afraid of making it too easy for myself if I can just get the money instead of having to make each dime
  • Afraid of having fun
  • Afraid of the flow
  • Afraid of losing what I have
  • Afraid life won’t take care of me
I also have a story that I should be able to do this on my own - after all, I know marketing, and in the info marketing business, you can make a lot of money quickly, if you do it right and have the right relationships. Ah, the “should”s.
Feeling into it more, there are several of these that have merit.
  • Afraid of losing what I have, and afraid of the flow are two sides of the same coin, and very active.
  • The feeling that I can’t trust life to take care of me, that I’ve worked so hard to build up what I have, and I need to hold on it - it’s also related to the one above, and very active.
  • I have historically not been good at hiring and managing people, which is why I’m still running a tiny shop.
  • The fear of pressure and overwhelm is very active in my daily life, and something that’s holding me back in many ways, as is the lack of trust that others are doing their part. Again, they’re clearly related.  
I know when there’s something I really want, but I’m really good at coming up with excuses, it’s because there’s some unconscious fear. This really hit home a few years ago when there was a conference I really wanted to go to. The excuse was that my son was just a few months old, and I couldn’t leave my wife alone with both kids. Someone I met with bust that excuse really good.
That got me curious. What is the real reason I’m afraid of going?
I sat down, and wrote out as many reasons not to go, I could think of. I already know enough. I need to make something with what I know instead of learning more. I don’t have the money. My wife can’t be alone with the kids. I can’t remember them all. But I do remember the last one, that came out as number nine or ten, as a complete surprise: I’m afraid I’m going to feel all alone and socially awkward. That one had so much punch, I could feel it in my stomach. I just knew this was the real reason I didn’t want to go.
That allowed me to make the conscious decision to go, even though I might feel socially awkward and alone. And so I went. And I did feel alone and awkward. And I survived. It was okay.
I’m not sure I’ve found “that one” here just yet, but the fear of flow feels the closest.
So: If there’s something you know you want, probably, maybe, but you’re also hesitating, try this: List all the reasons you’re holding back, all the reasons not to, and just keep going until you cannot think of anything else. And then add one more. And then another. Until you feel it in your gut. Until you know you’ve found that deep-seated, irrational fear.
Then you can make a conscious decision and move forward.


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