Startup Killer #2: Challenging Everything

Startups, almost by definition, emerge as a reaction to a perceived gap or problem within a given industry. They are often referred to as disruptors and this is by no accident. Either they challenge the way that things have been done prior, or they challenge the fact that something should not exist. Issues arise, however, as one digs deeper into the industry at hand.

As a startup leader, inevitably, you uncover other issues that are tangential to your core problem. Even important issues. And maybe you add that problem to your list of problems that your startup is solving for. And then another. And another. And another. And eventually, your startup is, at least in your mind, “redefining an entire industry”.

The issue with challenging everything is that it’s an exercise in futility. This approach of “challenging everything” often results in drastically reduced execution. As a startup, you have to pick what your core consists of; what one thing about your given industry are you challenging? This is a very tricky thing.

One of the most memorable lessons from my time at Addepar was this: startups don’t fail because of starvation. Sure, they may run out of money, but that’s often a symptom rather than a root cause. More often then not, startups die of indigestion: they bite off more than they can chew. They try to swallow too much and end up choking on their own decisions. It’s a (very visual) lesson that has stuck with me.

Startups rarely die of starvation; they often die of indigestion.

For some, including us at Exeq, our core focus has a lot of different touch points. It may seem from the outside looking in that we’re taking too much (financial management, loyalty, payments, promotions, etc) on to our plates. The reality is that we’re taking on one thing at a time, and that each item is a smaller part of the singular belief that exists at our core: we believe that both consumers and merchants want to be directly connected via data.

Now as we speak to consumers and merchants alike, we’ve discovered areas ripe for innovation, ranging from gift cards to inventory management to financial tooling for parents with older children. But these items are not in our wheelhouse, because they are not a part of our core challenge. They are simply tangential. While those things are important, it would be a mistake for us to pursue those items. Do we have opinions about those things? Yes. Do we think that someone should do something about the problems in those areas? Yes. Do we think it should be us? Nope.

As startups, we have to be extraordinarily disciplined in how we approach our respective industries. We have to be focused on what’s on our respective plates instead of biting off more than we can chew.

Startup Killer #1: Hype-Driven Everything

I think a natural side effect of being a leader is also being a voracious information consumer. Leaders are readers. We attend conferences, listen to countless podcasts, subscribe to tens (hundreds!) of blogs, and are constantly in conversations with other people we respect. We analyze trends in the industry, both the industries that our startups serve, and the industry of technology companies itself. But if you’re anything like me, you’re both guilty of it…and you recognize that there’s a significant problem with this approach.

If we’re not careful, then every new article, every new post can become a new wind that blows against the sails of your startup. The latest and greatest items found in industry trends become the enemy of the startup’s number one priority: focused execution. All of a sudden, you begin shoving “technologies” into your stack even when they don’t belong. You begin adding marketing strategies based on the blog posts of some brilliant marketer living in Portland, Oregon who works remotely for some big shot agency with a name that would double for a consignment shop. You introduce new concepts to your leadership team that you’ve read from a Forbes article about (insert tech leader here).

And all of a sudden, you’re an iced tea company with Bitcoin in your name.

From a design & technology perspective, just think of the trends that have come and gone. Rounded edges. Gradients. Countless Javascript libraries (remember mootools? script.aculo.us? prototype?). There are a lot of examples there. But the same is true even on the business side: trends exist, and they often cause us to introduce new things to our groups when it’s simply not necessary….and most often it’s a distraction from the things that do matter.

This introduction of new items is only the misdemeanor-level crime that can be committed here. Worse yet, you begin changing strategies, technologies, or company culture, ripping out things that are unique to your company that have grown from within and proven themselves worthy of keeping for at least a season. Within a short period of time, for very little reason, you’ve now given at least a particular group within your startup organizational whiplash, if not the entire team. All because you consumed the latest book. The latest magazine article. The latest blog post. The latest podcast episode. And are seeking to ride a wave.

And if we’re honest with ourselves, all of this is usually done to impress some third party (investors, the press, friends/family) that doesn’t directly impact the bottom line of the company.

Now. What I’m not saying is that these third parties don’t matter at all. Of course they do. I’m also not saying that we as leaders shouldn’t pay attention to trends in our industry. Or what’s happening in tech in general. Or that we should cease consuming external information in general. I’m saying avoid the hype. This hype-driven everything model of leading is simply unhealthy.

The number one way to avoid the hype? Have a clear, concise mission & vision for your company…and your own life as a leader. Write it down. One that’s fairly stable. One where a sudden swing in trendiness won’t cause doubt. Then, weigh every new trend against that mission & vision. Seems simple. But it’s not. Because some trends will seem like no-brainers at the time, but will only falter with time.

Startup Killers

In my observation, startups fail way before they run out of money. Running out of money is just the period of a long run-on sentence in a company’s history. Aside from this financial ending, there are a lot of items that kill startups: many out of the hands of founders, employees, and investors. Timing, market dynamics, and regulatory environment changes are just a couple of these killers outside of our control.

However, there are quite a few cultural items that will destroy your company from the inside out…items that are almost entirely in our control. I’ve seen a couple of these items creep into teams I’ve led during my career, and I thought I’d write about them here as a precaution to anyone reading.

In no particular order, here’s the list, along with a link to the detailed post as they’re written.

  1. Hype-Driven Everything.
  2. Challenging Everything.
  3. Challenging Nothing.
  4. Leading by Comparison.
  5. Not Iterating.
  6. Acting in Self-Preservation.
  7. Acting With Self-Entitlement.
  8. Organizational ADHD
  9. Pretending to Be Something You’re Not (or Not Yet)
  10. Prioritizing Intelligence Over Wisdom.

Hello World!

I’ve blogged off & on for years, and it’s been quite a while since I’ve spun one up. That said, I’ve a lot of different thoughts in my head that I’d love to get out. If you’re interested in any of them, feel free to add this to your favorite feed reader of choice.  For a bit about what you’re getting yourself into, check out the following:

About Me

I’m the father of 3 daughters. I’m a Christian most of the time. I’m a startup CEO. I love my country dearly. I’m cynical about most things, but also an avowed futurist. Wizards > Prophets. Borderline sociopath, over-the-border narcissist. Closet introvert. I love baths. I can clap with one hand. I love reading and the Nintendo Switch. Cigars are great. I travel a ton and eat even more. I often leave awful first impressions and great thirtieth impressions. Upper millennial living in New York; lower class Southerner.

What I’ll Write About

I’m a firm believer that startup CEOs should work and execute a lot more than they write and philosophize. That said, writing is a huge part of my thought process. It’s a way for to gain clarity on some things I’m thinking through and working on. Considering that, I’ll write on a little.bit of everything, but primarily startup dynamics, leadership lessons, and fintech/commerce-tech. Sprinkled throughout will be cultural notes on what I’ve been reading or listening to. Occasionally I’ll throw some travel notes or life notes in as well. Hope you enjoy!