The Unplanned Startup

“You have an unplanned startup?” said one of my good friends, a long-time mentor. “I’ve heard of an unplanned pregnancy, but I’ve never heard of an unplanned startup.” And this makes total sense. When it comes to creating a startup, your passions don’t just get out of control some dark evening, parked out of view, on the back seat of your parents’ car. It’s a deliberate sort of thing. There are legal forms to fill out and documents to file and fees to pay. Multiple people are involved. So, yeah, calling a startup “unplanned” does sound a little weird.

But once in awhile, you stumble upon an idea that is so obvious, it’s one of those “why didn’t I think of that” kind of moments. Except I did think of it. Actually, it’s a ridiculously complicated (and yet so easy-to-use) piece of truly magical technology that only a few dozen developers in the world are talented enough to build. I’m certainly not one of them. However, the guy who became my co-founder, a developer who can build it, read my pretentiously named infosec manifesto. He is one of the most brilliant people I know, and said “Wow, that’s interesting. Why don’t we stop talking about this and just build it?” And so we started building it. It sort of happened. While it’s too early to say for sure, our solution might just actually work. And it’s fair to say that if it does, it’s going to change the way — in many enterprises — that information security works.

Timing is everything in bringing products to market, and in information security, there has been no better time than the present. 2015 was the year of the data breach, and in 2016, there’s a massive business opportunity as companies start to do something about it. For our product, and by our estimate, the opportunity reaches up to 95% of the Fortune 500 and most governments at the federal, state and local levels. Ours is a technology that solves a massive, real and urgent problem. We have created intellectual property we can protect. Our solution can truly corner the market. And it’s an an area of technology that we actually know something about, have some credibility in, and can raise money in.

Solve a massive, painful problem. Check. Have the right team. Check. Don’t be too early or too late to market. Check. Fundable. Check. For the first time in my life, I raised outside money. Our investors saw the opportunity as clearly as we do, looked past all of the challenges of my involvement with Cuddli, and offered us a term sheet almost immediately. We swallowed hard and signed.

Fuck. “Now what?” That’s the question I asked myself and my co-founders (at both companies) while staring at the term sheet and deciding whether we should really do this. When you take someone else’s money, it’s not a marathon series of code sprint hack weekends working on a fun research project anymore, it’s a real and serious commitment. A baby is on the way and doesn’t much care about the one you already have.

That’s how you end up with an unplanned startup. Well, it’s how I did anyway. As it turns out, this can be a massive problem if you already have a startup, particularly one that is growing rapidly. I’m also the founder of Cuddli, an adorable bunny-themed geek dating app. We have finally hit our stride, have begun attracting the attention of the press around the world having been reviewed by two major Spanish newspapers and CNet just in the last couple of weeks (without any outreach by us, they just discovered us), and by the time you read this, we may have already released our long-awaited iOS version to complement our existing Android product. Our community is growing rapidly and after two years of eating Costco free samples for lunch (we have never raised outside capital) it’s finally starting to look like we might experience some success.

As it turns out, having two co-founders is making all the difference. Lots of formulaic advice dispensed to new startups says to have only one co-founder. Actually, this is pretty good advice; it’s hard enough to get two people on the same page, let alone three. In our case, we do have three founders: myself (I run IT, the business side of the company, and am head of product), Pinguino Kolb (our creative director and events coordinator), and Steve Tauber (our director of development). I was very fortunate to bring together a winning team with Cuddli. Both of my co-founders are extraordinarily talented, and we’ve all grown a lot in the last two years of building and shipping multiple Cuddli releases. It’s to the point where we can finish each other’s sentences. We built our company on a foundation of values we all share, and at this point, we’re mostly focused on growth.

Don’t get me wrong. By shifting my full-time involvement, I leave considerable slack to pick up. But it’s less than you might think. After all, my background is managing data centers and building enterprise software. It’s not in consumer, definitely not the dating industry, and the closest personal connection I have to the entertainment industry is throwing raves in China. As CEO, I have failed to raise money — and this is one of the core competencies of a CEO! I’m not nearly as plugged into the world of comics and pop culture as my co-founder Pinguino, nor do I have the deep entertainment industry connections that she does. I’m not as relentlessly focused on the metrics that drive user success as my co-founder Steve, focusing instead on the big picture. At times, I feel like I came up with an idea, brought together an unbelievably talented team, and then mostly got out of the way while they went out and changed the world.

And Cuddli is changing the world. Already, we’re making an incredible difference in the lives of our community. People tell us about having given up hope of ever finding someone compatible, and then they discovered Cuddli. In fact — and this still completely blows my mind — our Cuddli Ambassadors give us their time for free to help us grow, just because they love our product so much. In the dating industry, I can honestly say that I have never seen anything like this.

Having developed a brand people love, a marketing formula that works and a niche in which we can grow, our new marketing team is doing a phenomenal job at user acquisition (bearing in mind that we have no money). But more importantly than any of us, our users are starting to drive our product decisions more than my own decisions as head of product. After all, every time that we listen closely to our users and make their experience better, we seem to end up with more users and better reviews. We have enough users now to have multiple instances of the same feedback and to priority rank requests and ideas. Building a product and acquiring a user is a start — you still have to earn repeat engagement every day.

“You can’t ride two horses with one ass”

We know we have created something incredibly special. We’ll do everything we can to make it grow. But I may not be the best person to lead that growth. Right now, we’re not sure. Over the next few months, you’ll see my co-founders become a more public face of Cuddli. I’ll maintain my founder title, will still be involved, and will remain chairman of the board. After all, I invested my life’s savings into Cuddli, and I care deeply and personally about the product and team. But I also recognize that you can’t ride two horses with one ass. So we’re figuring it out, together. We’re an incredibly strong team, have worked through bigger challenges before and have come out stronger, so I’m confident we will get it right. And I’ll end up with enough time — full time — to build and grow my new company.

What’s the new company? For now, we’re saying very little in public, and are currently in stealth mode. We are, however, backed by the top accelerator in the field of information security. Once we announce it, we think it’s likely that our seed round will fill up fast. If you are an early stage investor in this space, please feel free to reach out. We are not raising yet, but would like to get to know you now.