The Two-Letter Word That Will Kill Your Startup

As a young entrepreneur, I remember calculating the market opportunity for multiple startup ideas using some formulation of the following “back-of-the-envelope” math:

The market has X-many-millions of people. So, if I only capture Y-tiny-percent of that market, I’m going to have Z-ridiculous-amount of money.

Luckily, I advanced beyond that kind of flawed thinking fairly quickly. However, one element of it persists in my work and the work of some of the most sophisticated and successful entrepreneurs I know. It’s a phenomenon I like to call the “if-conditional.”

Here are some versions of the “if-conditional” I guarantee you’ve heard. More than likely, you’ve personally used them:

  • “If we can close X% of the leads we’ve got coming into the pipeline…”
  • “If only X% of our website visitors click our ads…”
  • “If we can just get picked up by a couple of media outlets…”
  • “If just one of our videos goes viral…”
  • “If we get just one investor to commit…”

Do you see the pattern? It’s a pattern entrepreneurs deploy when strategizing or planning future steps. We’re often forced to make decisions without having all the data we need, so we make assumptions about some of the data, and those assumptions take the form of the above conditionals.

The challenge of the “if-conditional” is that it usually oversimplifies an incredibly complex task. Let me parse the examples above to show what I mean:

Example 1: “If we can close X% of the leads we’ve got coming into the pipeline…”

The act of “closing leads” in a sales pipeline isn’t something that magically happens. Depending on the product, a typical sales process can take anywhere from two to twenty meetings including qualifications, demos, proposals, negotiations, trainings, trials, contracts, and any number of other process-specific requirements.

In other words, “closing” even a single lead requires multiple people and dozens of hours of work. Doing that hundreds of times costs… well… a lot more.

Example 2: “If only X% of our website visitors click our ads…”

People don’t randomly click things on websites. Even your 90-year-old grandma who you think randomly clicks things on websites isn’t actually randomly clicking. Visitors to websites click things because UX developers, web designers, and optimization experts spend their careers studying website usage and creating designs that complement and control our actions

If you’re getting enough traffic to your website where some small percentage of clicks will result in significant ad revenue, I guarantee someone on your team is knowledgeable enough about user interfaces to be angry at you for thinking that getting clicks is easy.

Example 3: “If we can just get picked up by a couple of media outlets…”

Anyone who thinks getting press coverage is easy has never actually tried getting press coverage in their life. It’s a herculean undertaking with no guarantee of success.

Example 4: “If just one of our videos goes viral…”

HAHAHAHAHAHAHAHAHAHAHAHAHAHA

Example 5: “If we get just one of investor to commit…”

You might have better luck getting something to “go viral.”

The point is, when making assumptions about the progress of your company, the word “if” is unassuming but extremely dangerous. Yes, it’s only two letters, but those two letters often obfuscate tasks that are enormously complex, difficult, time consuming, expensive, and perhaps impossible.

Since entrepreneurs tend to be optimistic (in the sense that they’re good at imagining scenarios leading to positive outcomes), their optimism allows them to overlook the complexity of the tasks neatly summarized by their “if conditionals.” Unfortunately, those conditionals represent the overwhelming bulk of the work. When you minimize that work, you don’t allocate enough time and resources to get everything done, and the result is usually failure.

If you want to avoid the trap of the “if conditional,” here’s my simple trick. Anytime I make a statement using some form of the phrase, “If we do X, then Y will happen,” I immediately stop and force myself to re-say the same exact statement while replacing my original “if conditional” with the following phrase:

“If we can do something that takes 12 months and costs us a million dollars.”

By properly accounting for an additional 12 month, million dollar process when devising a strategy, I guarantee you’ll have a much better chance of success. Best of all, if the process doesn’t take you 12 months and one million dollars, you’ll have lots of extra resources to devote to the next project that starts with an “if.”

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I teach in Duke University’s Innovation & Entrepreneurship program and founded RocketBolt. I write about startups, pedagogy, entrepreneurship, engineering, and poetry. They’re all related, I promise.

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  • Asked my #learningtofail students to sell a @jollyrancher for $100 today. For the first time ever, everyone #failed.
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In related news, I heard a report from a campus tour guide that dozens of prospective students and their families were continuously being solicited to buy absurdly expensive candy during their campus visits.
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What a strange coincidence. Must have been someone else selling candy today, too...😒
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  • Finally had a freshman discover the Duke-sponsored free lunch opportunity.
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I forgot to ask Julia about the most important thing she’s learned in my class, but she’s taking another one with me next semester, so I feel like that’s a good sign she’s not just using me to get free food ☺️
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  • The end-of-semester FLUNCH parade continues... this time with Thomas, one of my soon-to-be-graduating seniors in the @dukeinnovation capstone who’s heading off to work @txinstruments.
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When asked to share the most important thing I’ve taught him about #entrepreneurship, Thomas had trouble coming up with an answer. Sounds about right 🤔
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  • “When you go into a company, whatever you decide to do, you want to be closest to the money. That’s the safest place to be in every business.” - @cleithe, VP of Sales for @adwerxre, who I conned into speaking to both my @dukeinnovation capstone classes.
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  • Doing a little FLUNCH with @adam_kershner,  Ben Lee, and Adam’s freshman roommate who was just there for the free lunch ☺️
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Adam says the most important thing I taught him was: “How to think differently and approach problems in an unorthodox way, and how that approach to problem solving is one of the most valuable lessons from Duke.”
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Honestly, I don’t think I taught him that. I think he already knew it when he showed up as a freshman in my very first class @dukeuniversity. Now he’s a graduating senior in my @dukeinnovation capstone, and it’s been a privilege to watch his Duke journey. I’m sure he’s going to do great things, and I look forward to following his post-college journey via Instagram.
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  • Here’s the final viral #meme  video created by my @dukeinnovation #learningtofail class: #piggybackchallenge
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Would you randomly take a ride on a stranger’s back? 😁
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Spent an hour discussing how I&E can help support Duke’s new #esports initiative, then spent an hour with @clairecatenaccio talking about launching a new I&E course connected with the #classics department.
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Watch all the way through. Totally worth it 😂
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  • Viral #meme number two from my @dukeinnovation #learningtofail class: #forkflipchallenge
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They seem to be liberally interpreting my “nothing dangerous” rule... 😒
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  • In today’s @dukeinnovation #learningtofail class, I challenged my students to create #viral memes.
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They’ve got one week to get as many people as they can to watch, recreate, and post their own versions.
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Who wants to help them out? Here’s the first meme: #smoothpickupchallenge
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  • A bumblebee 🐝 has fallen in love with my motion-activated security camera. It would be adorable if it didn’t keep making me think a burglar was breaking into my house 😒
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