Bootstrapping 101 - Diematic Behavior

Some animals have a defense mechanism called Diematic Behavior. It is a natural defense meant to bluff a predator into believing something untrue about the creature in question.

A critical tactic employed by most startups is the act of making oneself “look bigger”. For example, this frilled lizard looks a lot more formidable when agitated into this state:

For bootstrapped startups this is especially important. You will be by yourself, or at best it will be you and one or two more co-founders. Odds are that every company you are trying to market and sell to is bigger than you. In fact, it’s probable that whomever you sell to is very unlikely to buy from you given your size regardless of how much value your product has.

Before we dive in, also understand that the advice given here is out the window if you get asked a direct question about your size. In those cases you should be ready to answer honestly with a canned response, something you’ve rehearsed and speaks to the positive benefits of being an early stage startup. Let’s touch on that again towards the end.


It sounds simple, but get used to saying “we” with respect to your team and company. Even if you’re by yourself, it’s important to never speak in terms of “I” or “me”. This is best illustrated though some example scenarios that happen on almost every prospecting call:

  • Question: How does support work?
    • Wrong: You’ll have access to me, the founder whenever you need something!
    • Better: Every customer has a dedicated customer success person. In your case I’ll be handling the onboarding because I’d like to learn more about what issues our typical customers run into during this process.
  • Question: How long have you been around?
    • Wrong: We just formed the company six weeks ago.
    • Better: We’ve spent quite a long time in stealth mode prototyping and testing with various early adopters. Only recently did we decide to make the product generally available. We’ve also been building software in this space at other companies for many years.

Don’t hate the player

As a bootstrapper, you are first and foremost a marketer even if your strength is more technical. Skillfully wording things to paint yourself in the best possible light is a tactic even the largest corporations in the world employ.

Getting into this game means sometimes bending reality for survival. Your competition is damn sure going to do it.

Ever see a soft drink ad on TV showing the most amazing things being achieved by simply drinking liquid? The subconscious suggestion here is anything is possible by cracking open a bottle of sugar water.

At best it’s bending reality to a ridiculous level. At worst it’s a flat out lie. Point being, getting into this game means sometimes bending reality for survival. Your competition is damn sure going to do it.

Let me see what I can do

All of us have egos, and from my experience the ego gets even more inflated when combined with a job/role/title in a professional work environment.

To make matters worse, vendors play the part of the dog in the kick the dog metaphor. This general rule has applied to every vendor situation I’ve encountered.

It’s easy to turn this into a positive scenario for a seller. The more inflated the ego, the easier to take advantage. Think of it as ego jujitsu, using your opponents strength and weight for leverage against them.

Customers love to feel taken care of, and generally feel they’ve earned some special/custom treatment. They know you need them for your business to succeed and they will expect their pound of flesh.

Price (and assumed discounts) are the most common way this manifests itself. Here is a typical back-and-forth towards the end of the sales cycle:

The goal is to remove the binary choice of “buy” vs “don’t buy”. Replace that with “buy package A” or “buy package B”.

Customer: $500 a month is out of our budget for this year.

Vendor: If you can get approval for an annual contract we can knock 10% off and get you to $450.

Customer: The most we could do is $400/month, and we can only commit to a three month pilot.

Vendor: That’s going to be tough - I haven’t been authorized to go that low. Let me speak to my boss and see what I can do for you.

This tactic serves multiple purposes. First, it gives you a chance to actually think about what kind of deal you’re willing to offer. Second, it lets you put the ball back in their court with choices. This is key to feeding that ego and putting the customer in charge. The goal is to remove the binary choice of “buy” vs “don’t buy”. Replace that with “buy package A” or “buy package B”.

At this point take the time to figure out what the final offer looks like. Maybe a 3 month pilot at $400/month is good enough - or maybe it’s worth your time to offer $350/month if they sign an annual contract. If you find two options you can live with, put the decision in their hands.

Back to our goal

The primary objective is obviously to close the deal. To the point of this post, however, this interaction also supports an overarching strategic objective - to apply Diematic Behavior and give the perception of a larger organization.

It’s ironic that we are generally apprehensive of bureaucracies or large organizations that hold things up, but most buyers are doubly scared of investing in an early stage startup + product. It’s a tricky balance but sometimes necessary.

In this case we’ve given the appearance of a larger organization with more than one stakeholder making compromises on behalf of our customer. They feel taken care of, that we’ve gone “above and beyond” to help them with their budget concerns and getting them a great deal. They can go to their boss and proclaim victory, their ego satiated.

Full circle

In the early days when I was still solo I spent an inordinate amount of time on a deal with RingCentral. I had done multiple demos over the course of 6-8 months and it wasn’t until they hired Josh Hill, famous for his Marketing Rockstar Guides that any real progress was made. I had two demo calls with Josh and a few months later they closed.

Almost two years after that we were hosting a customer event at Marketo’s annual conference. Josh showed up and we finally met in person. I introduced myself and the first words out of his mouth were “oh, hey, you are the sales guy I talked to back when we bought Siftrock.” He was surprised to learn I was actually a founder. In his mind I was a cog in a bigger machine, and that perception was key in closing the deal.

Coming clean

There will be customers who straight up ask “how big is your company?” Trust is a big deal, and in these cases it’s best to be as transparent as possible. You should have a canned response ready. Here is mine from the early days when I was still solo:

Believe it or not it’s just me working on this daily right now. I’ve been fortunate to have worked in many technical and executive roles at other startups and decided to try the bootstrap route. I have a great network of advisors and outside help, and am planning to build a team organically when the time is right. Fixed costs are very low and I’ve invested enough personal capital to run independently for several years. I believe in this product and am targeting early adopters who value a personal relationship with the founder and the benefits that come along with it, not the least of which is helping decide on major pieces of functionality that will bring you immediate value.

The bottom line from here: your product better have a ton of value / solve a critical pain or the customer will have a tough time making the required leap of faith.