Your Business Is Dying Because You Just Suck at It (Seriously)

Don’t hate the player or the game; play the right game instead.

A fellow entrepreneur friend recently spoke some words of wisdom that made me recoil with shame. I was so embarrassed that I almost buried my secret and refrained from writing this article…but I figure I can’t be the only entrepreneur who’s ever dealt with this, so in case it helps someone else out there, I’m going to share my shameful confession.

Before I get into the confession bit, I’m going to paraphrase a few of the tenets this fellow founder spouted:

• If you adopt ridiculously high standards (for yourself, your business, your product, your marketing, and everything in between), you’ll likely be supremely successful
• Those who love (or at least strongly like) what they’re doing (the journey) will always outshine those who are only in it for the end goal with respect to lasting success
• The person who can suffer through discomfort the longest will likely win in the long run

In retrospect, those statements are fairly commonsensical and likely along the lines of platitudes we’ve all heard (and agreed with) before. Nonetheless, if I honestly ask myself whether I approach every single one of my ventures with an affirmative nod toward all of those perspectives (along with a dozen other secrets to success), I have to say no.

One of the curses of knowledge is that knowing what one “should” do — from a logical, “acing the multiple-choice quiz” point of view — can influence or override what a person wants and chooses to do. In turn, making the logical, or seemingly business-minded, “correct” decision can actually lead to unintentional sabotage that goes undetected (while wreaking havoc below the surface) for many months or years to come.

If you feel that (or fear that) any of your ventures are falling short of their potential — or that your entrepreneurial success is falling short of yours — these are the questions to unpack.

Are your standards high enough? (or “just enough”?)

I used to think most entrepreneurs — myself included — were a notorious breed of customer-pleasing perfectionists with sky-high standards and no tolerance for anything less than their best (in all respects). While I’d love to tell you that’s proven true, the reality is that it hasn’t, and sometimes that’s for understandable, even logical, mathematically sound reasons.

A few of those reasons?

• If you spend forever perfecting your product/service/offering, you’ll never get it out to market, and thus, never launch, grow, or succeed.
• There’s a point of financial diminishing returns in which you’d have to spend more money to further improve the customer experience than the customer is willing to pay, and thus, you’d create a perpetually unprofitable offering.
• If it’s your second, third, or fourth+ venture, you may no longer be enamored with creating an unparalleled customer experience (and making the best product or service ever), so your focus may be more on creating one that is just good enough that customers will be satisfied and you’ll turn a profit.

I recently found myself admitting that the quality for one of my pre-launch ventures falls very short of my best. It’s good, and it may be on par with much of the competition, but it isn’t “blow them out of the water” or “blow my customers’ minds” good. That realization cut me like a knife because I know exactly why, what I’d have to do to right the ship, and why I’m not sure I want to do that…

The simple reason why this pre-launch venture doesn’t live up to those top 1% standards is because I don’t love or enjoy it enough to have put in that extra time, resources, and effort. It’s not a good or admirable or acceptable reason; it’s just the truth. For those wondering why in the world I’d move forward with a venture I don’t love or enjoy, have no fear: I’ll get to that a few sections down, as it’s a key saboteur.

I now have three options:

1. Scrap the whole thing
2. Spend the time, effort, and resources to get it up to snuff
3. Plan to launch as is, well aware that it’s nowhere near my best work or capabilities

Option 3 is a horrible one, but if I lean into the sunk cost fallacy, it kind of makes sense: I’ve already put this much time, resources, and effort into it, so I might as well give it that one final push out the door.

Here’s the problem, though: Launching a business is not a one-time, short-lived push-out-the-door type experience. Instead, it’s a long-term journey of feedback, tweaking, iterations, and ongoing improvement. The problem with that choice (which morphs into option 2) is that I’m not sure if I’m able or willing to take it on for this particular venture, given the other priorities and businesses on my plate.

Option 1, of course, is the most defeating, as it requires willingly, boldly, and undeniably giving up and admitting this venture was a mistake I failed and chose to walk away from before it had a chance to fly.

If you want to avoid a catch-22 like the one I’m in, I’d regularly ask yourself — from day 1 to day 100 and beyond — whether you’re actually building a great product, service, or business, or whether you’re settling for just good enough.

Sometimes good enough can suffice, depending on your goal, but you should never be surprised why you didn’t build the industry-leading company, raise funding, or rake in $100M+ profit if your business wasn’t built with top 1% level standards.

Only so many companies can be #1 (in their industry, geography, niche, etc.). Whether you want to be #1 or #1,000, I can’t see a world where approaching your venture with less than top-notch standards makes any sense.

The key here isn’t to be eternally hard on yourself. Instead, it’s to realize when you aren’t being hard enough on yourself, your venture, your product, or your service, and assess why that is. That answer may tell you everything you need to know about your next move, and it may not be the expected or most admirable one, but it may be the right choice for you.

Are you unnecessarily playing in hard mode?

I’ve recently had this conversation with a few founders, and I’ve come to the realization that far too many entrepreneurs out there think it’s somehow better or admirable to play the game in hard mode. By playing on “hard mode”, I’m referring to the idea that founders should happily, willingly choose a difficult path and then struggle to overcome it.

Hard mode can be choosing a difficult venture. It can be choosing an industry or product or service that taps into a founder’s weaknesses, rather than their strengths. It can refer to choosing a business so out of their depth and far from their realm of expertise, when they had much “easier” (for them) options readily at their fingertips.

Sure, it might sound more impressive to cure cancer than to sell digital services or monetize media. That said, if you’re starting from ground zero in the medical space (and thus, really starting at a negative 500 compared to your competitors), while you could hop into a digital services or media venture and hit the ground running due to your vast experience, you’re voluntarily choosing the harder path. Not only are you choosing the harder path, but you’re significantly lowering your likelihood of and increasing your expected time horizon to any modicum of material success.

When I first started my entrepreneurial journey after leaving Wall Street, I sabotaged myself from day one by attempting to play a game on hard mode when I was a fetus-level beginner. I chose to solo-found a tech company back before I even knew how to build a website or an app.

After that one failed (and a few others, if I’m fully transparent), I went back to the drawing board and started resurrecting my legacy skills, leaning into my strengths to build businesses that would be objectively easier for me. Were they? Yes. And no, they may not have sounded as impressive as that fancy user-generated-content, revenue-sharing, user-voting sweepstakes-social network hybrid (I know, I way overcomplicated that), but here’s what they did do:

• Generate revenue! (within a few weeks or months, not years)
• Get profitable
• Scale quickly and predictably
• Beat out the competition because they were actually high-quality — since I had access to the skills, knowledge, connections, and resources to make them so

In other words, once I stopped punching above my weight for the prestige factor and instead started prioritizing profits and my genius zones, my businesses started succeeding.

The beauty of avoiding “hard mode” is that as your likelihood of success increases (and your expected time horizon to that success decreases), your ability to later dabble in, venture into, or invest in those more impressive “hard mode” problems (like curing cancer) becomes a more viable reality. Financial success is only selfish if you use it selfishly.

Are you playing the wrong game altogether?

There’s playing a game that’s above your weight class (but one that you’re incredibly passionate about), and then there’s playing the wrong game altogether. Unfortunately, the best-intentioned startup advice — including some that I’ve doled out over the years — can lead smart, capable people to choose the wrong game because logic told them it was right.

In case you were wondering why I would have ever put a second or a dollar into that venture that I may scrap altogether, you’d have to understand the decision my entrepreneurial mind weighted. It went something like this:

• I could start a somewhat boring business that’s synergistic with other companies I own (and thus likely to enhance their value and vice versa)

or

• I could venture in a brand-new direction, allowing myself to explore a less practical, less relevant, more passion-focused venture

Being the more logically-minded, finance-steeped founder I am, I opted for the former (“the sensible shoe”), when I was really itching to try my hand at the latter (an almost frivolous, guilty pleasure “fun” business).

Yes, it was practical. Yes, it was synergistic. Yes, it makes a lot of business sense for someone building a valuable portfolio of companies. But no, it didn’t — and doesn’t — light me up. No, I don’t really want to spend the time, money, resources, or effort to go the extra mile. It’s not because I’m lazy, ignorant, cheap, or a bad founder; it’s because I’m just not that into this venture.

The hardest thing about that excuse is that it sounds kind of superficial and lame. Many founders before me have built businesses around random industries and problems they weren’t in love with and have profited handsomely. Why can’t I just stay the course and do the same?

Here’s why: I’ve built the practical business. In fact, I’ve spent years and the majority of my entrepreneurial career building the more practical, synergistic, logical businesses. At this point, I’m getting a little burnt out of stifling what I want to do for what I should do, and that is the death of a venture right there.

If you’re going to be an active CEO, you can’t resent the business you’re building and growing. If you do, you’re better off scrapping it, selling it, or handing the reins over to someone else who cares enough to do it justice. With respect to my involvement in this particular venture, I just may not be that person right now or anymore, and knowing and admitting that may be the first step toward where I need to go.

Sometimes “try, try again” isn’t enough

We’ve all heard the adage “If at first you don’t succeed, try, try again”, and while it comes from a good place, it isn’t always the bulletproof solution to the failure at hand. You can try as hard and as many times as you want, but you’re unlikely to get as far or as fast as someone who inherently enjoys the journey.

Likewise, if you’re pursuing things you’re not innately good at, or leaning into your weaknesses and shortcomings rather than your strengths, you’re making success that much harder to attain and farther from your reach.

Lastly, are you trying to exponentially overdeliver and exceed customers’ expectations or to do just enough to get by and avoid a complaint or refund request? If you’re honest with yourself, you’ll know exactly how high — or low — your standards are, and that alone should shed great light on why your business is or isn’t where you’d like it to be.

If you want to succeed faster, easier, with a higher likelihood of long-term growth, profits, fulfillment, and a sky-high net promoter score, simply lean into a venture (or industry) that lights you up and plays into your strengths and competitive advantage, and do nothing less than your best work. If you do that, you’ll make the journey enjoyable enough that the destination may reveal itself sooner than you expect, and the results may exceed even your highest expectations.