The 7 Deadly Sins of a Bootstrap Startup

My advice to college grads is this: There's never a better time to start up than when you're starting out. You've got your entire adult life ahead of you. You've got fire in the belly, little overhead and few responsibilities. Conditions are ripe. A special opportunity has been laid at your feet. I say take it. 

But first, learn from my mistakes. I've built three self-funded startups: one failed, one was acquired, and the other I now passively operate. All in all, I've been around entrepreneurship and startups for ten years and this is my post on the pitfalls I've experienced first-hand, my 7 Deadly Sins of a Bootstrap Startup.

1) Getting validation for your startup by those who have a vested interest in your happiness

It's always easiest and safest to ask a friend or family member what they think about your startup idea. And it's just as easy (and safe) for them to tell you they think it's the next Facebook.

It's hard to get honest feedback from those we're closest to because they don't want to burst our bubble. They want to see us happy and that's understandable, but they can't be the people we get our validation from.

Instead, go get validation from someone (like a real potential customer) that has no personal connection to you. Zero. Zip. Zilch. Someone who has no emotional stake in you or what you're up to helps guarantee more productive feedback. Family is great for support, but I say go find some real potential customers and see what they think.

2) Overemphasizing "Launch Day" 

I've been bitten by the launch bug and boy does it sting. On my third startup, Jon and I had poured tens of thousands of dollars into building and getting to "Launch Day." Everything was set. Our open-for-business email was ready to send, our pithy ads were prepared, Facebook posts and tweets were cued up, and our Google AdWords campaign was itching to go live. The big day finally came.

We launched and... 

Everybody came! Not quite.
Everybody cared! Wrong again.
And everybody purchased! Ha!

Our first day of sales... $10

This is where you get the opportunity - if you stick with it - to form the invaluable character trait called perseverance. We kept plugging away, day after day, tweaking our system, talking to customers, strategic partners and just being consistent. 

Our sales after the first year of business... $246,281.57

Again, don't overemphasize Launch Day. And don't waste time trying to get everything just right. Nobody's looking that hard. Think in terms of "Launch Year" or "Launch Quarter".

3) Unwilling to do the hard things daily

This is a sin of omission rather than commission. As a founder, you must be willing to do the hard, painful things that often bring about startup success. You can't live in the land of easy, reactionary work. You must, as John Maxwell puts it, "Get comfortable with being uncomfortable." 

The "hard things" are those objectives that have the highest return for you business. It's where the majority of your time should be devoted. It may be hunting for a connection to a potential strategic partner, or it could be writing a series of blog posts that will earn you the attention of potential customers. The "hard things" will look different for each founder. Just make sure you identify them for yourself and then tackle one each and every day.

4. Founder pride 

We all know what comes before the fall. That's why you have to steer clear from pride at all costs.

Here are a few ways you know that pride has its hooks in you:

• When you elevate your contribution over others

• If you get offended easily

• If you see little value in the feedback of others

• If you hold grudges

• If you fight for your ideas "to the death"

All of these smack as having an overinflated ego. I've been there and it's miserable.

A way we're not letting pride creep in at our startup is by practicing organizational health as described in Patrick Lencioni's The Five Dysfunctions of a Team. Organizational health promotes healthy conflict resolution on an ongoing basis. The idea is simple. If you don't confront it, you won't cure it. So regular periods of conflict resolution will help you stay healthy with the members of your team. 

5. Failure to assemble the tribe

Companies that neglect their tribe, fall into the trap of focusing all their energies on their product. And they do all their work in secret. Once they're ready to launch, they come out of their cave and shout from their social networks, "Come look at our shiny product! Look what we made! Look! Look!" This is marketing to the crowd. It's unthoughtful and lacks creativity.

Startups that get it right begin assembling their tribe the moment they decide to begin building their product. They get the tribe in on the features, in on the design, in on the specs, in on the development. Over time, they win the hearts of those future customers because they committed themselves to both the product and the people who will use it.

You can easily get focused on the product and forget about the tribe for which the product is made. Smart startups assemble the tribe.

6. When the Maguyver mentality goes missing

Maguyver had a knack for putting to use whatever was at hand. Wasn't the guy always able to make something useful out of what was laying around?

Your chances of startup success increase when you learn how to get the most out of what you have. It's a copout to say, "We can't be successful until we have 'this' or until we get 'that', or until we hire 'this position' or until we get 'that round of investment closed.'" As I've said elsewhere, these are all excuses masquerading as explanations.

Field Marshal Helmuth von Moltke famously said, "No plan survives the first contact with the enemy." That is terrific advice for waging war and starting a company. And that's why the Maguyer mentality is so important.

The Field Marshal has a lesser known quote that, in my opinion, is more poignant, "Strategy is a system of expedients." In other words, scrap your business plan as soon as the world begins telling you something different. Forget what's optimum and actively plan for and carry out contingencies. Don't wait for the stars to align, rather, pick the best possible scenario under the current circumstances and go to work. 

7. When you build a product that doesn't solve anything for YOU

The great thing about being an entrepreneur is the belief inside that you really can change things. You believe that things can get better with a little ingenuity and hard work. 

The world needs entrepreneurs to face down uncertainty and help solve society's problems. But, we as entrepreneurs, must make sure that we're solving problems not just for society's sake, but for our own. 

When we tackle a problem in our own life...

• We're highly attuned to the needs of our customers (because we are one)

• We're strongly aware of the market dynamics: We know what's missing, we know our competitors, we know where our tribe hangs out, we know what they believe, and we know how to reach them.

• More than just money or blind success is driving us. Our deepest desire (hopefully) is to see the problem solved.

I've heard of people surfing sites looking for the hottest startup ideas or businesses with the biggest profit margins, or lowest startup costs. Building a product with these types of motivations driving you, in my opinion, won't be enough to sustain you.

You need to have the vision of your own problem solved. You need to imagine what your life will be like when your product exists. 


There you have it, my 7 Deadly Sins of a Bootstrap Startup. If you have any questions about any of the seven, just find me on twitter. And, if this post was at all helpful, would you consider sharing it through one of your social networks? There's a little button right over there. ---->